The Oaks Real Estate, Homes, Condos for Sale in Osprey/Nokomis, FL - Ed Grabowski

5 Beds ⋅ 8 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the sought-after, gated community of The Oaks, in Osprey, adjacent to stunning Sarasota, known for the arts. Bordering the Heron Course on the eighth fairway, this iconic two-story estate boasts incredible opportunity for limitless potential. The entire interior is freshly painted, to enhance vision of stateliness. With five bedrooms, 7.5 baths and a sprawling layout, this magnificent property is an exceptional backdrop, just waiting for your personal touch. Arrive in style via the elegant front circular driveway or utilize the private rear driveway leading to a rare four-car garage. Inside, the home is masterfully designed for grand entertaining and everyday comfort, with a sweeping curved stairway at the entrance, setting the stage to an exquisite residence. The first floor features a formal living room and a sun-drenched family room complete with a fireplace, custom built-ins and multiple French doors, leading to the outdoor bliss. A screened lanai lays the foundation for Florida living at its finest, showcasing an enormous 33-by-46-foot sparkling heated pool and spa, expansive patio and an outdoor kitchen. The expansive open kitchen is a chef's dream, flowing seamlessly into a casual breakfast nook. For formal affairs, the large dining room offers custom cabinetry and an adjacent wet bar. The main-floor primary retreat is a sanctuary, featuring a dedicated sitting area and luxurious dual en-suite baths. There is more closet space than a clothes diva could possibly desire. The first floor is completed by a handsome office/library with built-ins, a powder room and a guest bedroom. Upstairs, you will find three additional en-suite bedrooms, one of which benefits from private back-staircase access, ideal for an au pair, in-laws or VIP guests. With every bedroom featuring its private bath, privacy is guaranteed for all. Outdoors, the walled double lot provides a private tropical oasis, all with tranquil, serene views. On a practical note, roof was replaced in 2019, with hurricane shutters, for peace of mind. Two 18-hole championship golf courses, 12 Har-Tru tennis courts (four lighted), croquet and pickleball courts, a state-of-the art fitness center, fine and casual dining options and a calendar of social events, The Oaks is Sarasota’s leading golf and country club.

916 Macewen Drive, Osprey

$1,649,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting. A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout. The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer. Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community. Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

75 Osprey Point Drive, Osprey

$4,790,000

4 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.

101 Osprey Point Drive, Osprey

$1,289,000

3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac within The Oaks Preserve. The property is framed by lush conservation views and mature oak canopies and blends classic architectural character with thoughtfully curated updates. Professional lawn care and irrigation are covered by the monthly fees. Designed for both everyday comfort and effortless entertaining, the residence offers 3 bedrooms, 3.5 baths, multiple indoor and outdoor gathering spaces, and a seamless connection to its tranquil natural surroundings. Inside, refined architectural elements, including crown molding, hardwood flooring, custom millwork, vaulted ceilings, plantation shutters, and two fireplaces, create a warm yet elevated aesthetic throughout. The great room opens effortlessly to the screened Florida room and private outdoor living spaces, while the dining room’s built-in serving bar and wine chiller complement the beautifully updated kitchen featuring custom white cabinetry, granite countertops, stainless steel appliances, an oversized island, and curated designer lighting. A Sonos sound system extends throughout the residence. The primary suite serves as a retreat with vaulted ceilings, a bay window sitting area, outdoor access, and a fully renovated spa-inspired bath completed in 2023. Dramatic marble-look tile, a frameless glass shower, dual vanities, and a freestanding soaking tub positioned beneath a skylight create a serene, resort-like experience. Additional baths have also been extensively renovated with elevated finishes and designer fixtures, while the updated laundry room introduces custom storage, shiplap detailing, and functional built-ins with a refined coastal aesthetic. Upstairs, a spacious bonus room with a fireplace opens directly to a newly renovated second-story deck. With a full bathroom, the second floor is an exceptional flex space ideal for guests, recreation, or private lounging among the treetops. Outdoor living is equally compelling, centered around a seven-foot-deep heated pool and spa surrounded by brick pavers, tropical landscaping, and serene preserve views with no rear neighbors. Recent improvements include a new pool heater, filtration system, pump and motor, new lanai screening and aluminum framing, exterior paint completed in 2025, new air conditioning for the main floor, and a new second-story flat roof with a warranty. Located within the gated community of Bishops Court inside The Oaks Preserve, residents enjoy 24 hour guarded gates, maintenance-free living alongside access to one of the region’s premier private club lifestyles, featuring two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a state-of-the-art fitness center, fine and casual dining, and an active social calendar. Golf or Social Membership is required with homeownership. The Oaks Club has been awarded the Platinum Clubs of America, Distinguished Emerald Residential Country Club, and Audubon International Certified designations. Located between Sarasota and Venice, Osprey is known for its natural beauty, waterfront lifestyle, and easy access to everyday conveniences. Residents are just moments from Siesta Key, downtown Sarasota’s dining and cultural attractions, marinas, shopping, Legacy Trail, and the renowned Pine View School, creating an ideal setting for both year-round living and seasonal enjoyment.

156 Bishops Court Road, Osprey

$1,950,000

5 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed floor plan with expansive living areas, soaring ceilings, and an abundance of natural light. At the heart of the home is a completely renovated chef’s kitchen, featuring high-end finishes, premium appliances, custom cabinetry, and a seamless flow into the main living and entertaining spaces, perfect for both everyday living and hosting guests in style. Each of the five spacious bedrooms offers comfort and privacy, while the six bathrooms provide ample convenience for family and guests. Recent updates include a brand-new roof, and renovated kitchen, offering peace of mind and long-term value for the next owner. Outdoor living is equally impressive, with tranquil surroundings that capture the essence of Florida living, ideal for relaxing, entertaining, or simply enjoying the natural beauty that defines The Oaks Bayside. Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility. Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.

97 Sugar Mill Drive, Osprey

$285,000

1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.

51 Mac Ewen Drive Unit 14, Osprey

$235,000

1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

51 Macewen Drive Unit 5, Osprey

$1,325,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

SELLERS SAY SELL! BEST PRICED 4 BED IN THE OAKS - MAJOR UPDATES ALLOW IMMEDIATE MOVE IN - NO REMODELING NEEDED! FRESH STYLE....FRESH PRICE! Behind the gates of The Oaks - Bayside, this beautifully redesigned estate presents a rare opportunity to enjoy refined country club living at a compelling new value. Updated and thoughtfully improved with designer transitional style - 140 Sugar Mill Drive offers ultimate privacy with lush landscaping, elegant interiors and resort living. Thoughtfully created for refined entertaining and everyday comfort, you'll enjoy 4 bedrooms and 4 full baths - all on one level - within a bright, open floor plan with custom architectural details throughout. The impressive chef’s kitchen is both stylish and functional, featuring Silestone countertops, premium Sub-Zero and Wolf appliances, an expansive island with seating and a striking bar—perfect for hosting gatherings or enjoying relaxed mornings at home. Separate dining and living spaces allow room for dedicated entertaining - making any occasion a treat! The private primary suite is "magazine worthy" - a sublime but peaceful retreat complete with a tremendous walk-in closet, custom built-ins and a beautifully appointed bath showcasing dual vanities, quartz countertops and a seamless walk-in glass shower. The home is truly a split plan - offering privacy with three additional suites - perfect for guests, a study or exercise/hobby room. The home takes every advantage of space and storage - and you'll be the envy of the neighborhood with the "thought of everything" laundry room and spacious garage. Step outside to exceptional outdoor living - designed for year-round Florida enjoyment. The expansive screened lanai features a heated pool and spa, elegant travertine pool deck, turfed yard with putting-green surface (only home in the Oaks) and new remote-controlled hurricane screens. Surrounded by mature, lush landscaping and a privacy wall, you'll feel the design intent for ultimate seclusion and relaxation. The home not only looks beautiful - it's been maintained to provide peace of mind with a newer roof (2021); impact-rated windows & doors (2021); 2 new HVAC units with UV purification (2021); motorized exterior hurricane shutters (2025); air conditioned garage and hurricane doors; 500 gallon propane tank (2022); electrical service panel (2021); rear yard golf turf (2025) and fresh interior & exterior paint. The Oaks - Bayside is a gated neighborhood with a private day dock on Little Sarasota Bay - perfect for launching kayaks or simply enjoying the sunset. The Oaks is one of the region’s most prestigious 24-hour guard-gated country club communities, residents enjoy an extraordinary lifestyle that includes: two championship 18-hole golf courses; three dining options and ballroom; tennis with 12 Har-Tru Hydro-Grid tennis courts; four pickleball courts; croquet lawns; fitness center and Junior Olympic heated pool; bocce, basketball, playground and extensive social opportunities. Perfectly located west of the trail in Osprey, you're just minutes from Sarasota's outstanding dining and cultural offerings, gorgeous beaches, Legacy Trail and Pine View School for the Gifted. A wonderful opportunity to enjoy Florida's ideal county club lifestyle! (Club membership is required with no waitlist at the current time.)

140 Sugar Mill Drive, Osprey

$1,500,000

3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Welcome to 480 Oriskany Court...Tucked away on a quiet street within the prestigious Oaks Club in Osprey, Fl; This elegant residence overlooks the fairway of the Heron 14. This home sits on a Premium golf course lot with additional privacy view across the street . Designed by Toll Brothers, this one story, 3200 sq. Ft. home with 3 bedroom ( plus office ) offers gracious entertaining and comfortable everyday living. A well-appointed kitchen with newer appliances opens seamlessly to a family room for hosting family and friends. Step outside to your private oasis and serene backyard, a perfect place to read or host your Book Club. A new roof and pool cage(2023) have been added. This home has a 3-car garage with an electric car charger. Living in the Oaks Club means enjoying two Championship golf courses, 12 har-tu tennis courts, 4 pickleball courts, gorgeous croquet lawns and a State of the art fitness center with an outdoor heated pool. Membership is required for home ownership. In this premier Golf and Country Club. Enjoy the vibrancy of downtown Sarasota for culture, arts, dining, and shopping. Just a short distance to the world-renowned Siesta Beach and the Gulf coast of Florida. Stop by to learn about the active social calendar - a place to make wonderful memories. Seller will provide credit allowance for $40,000.00 at closing for impact windows upgrade. Also, this listing window display shows 1,599,000 not current price $1,500,000.

480 Oriskany Court, Osprey

$2,300,000

4 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Located in the prestigious gated community of The Oaks Golf & Country Club in Osprey (Sarasota area), this elegant single-story residence at 530 N Mac Ewen Drive offers resort-style living with championship golf just steps away. Spanning 4,346 square feet under air and 5,837 square feet under roof on an oversized lot, the home features 4 bedrooms, 5 full bathrooms, 1 half bathroom, and a 3-car garage with built-in cabinets and the bonus of a car lift allowing for 4 cars in total. Presented fully furnished and turnkey, this meticulously maintained home is move-in ready and showcases exceptional craftsmanship throughout. Italian granite flows through the interiors, complemented by designer lighting and a whole-house water softener/filtration system. The custom handcrafted kitchen is a chef’s dream, complete with a hidden pantry, soft-close drawers and doors, spice drawers, double oven, and premium Viking Pro appliances. A custom built-in wet bar with ice machine and pull-outs adds convenience for entertaining, while a panoramic electric fireplace anchors the living spaces. A built-in sound system throughout the home and custom closets in every bedroom (including a Therma Sol steam shower in the primary suite) enhance daily comfort. Additional practical luxuries include a bolted-in safe. Step outside to an expansive lanai and backyard oasis featuring a custom-designed pool and hot tub with fire feature, plus a fully equipped outdoor kitchen—perfect for al fresco dining and year-round enjoyment. Industrial-grade landscape lighting (valued at $40K) beautifully illuminates the mature, oversized lot. Residents of The Oaks enjoy 24/7 gated security and world-class amenities including two 18-hole championship golf courses, tennis courts, pickleball, a state-of-the-art fitness center, and vibrant social events. This turnkey luxury home in one of Sarasota County’s most sought-after private communities is an exceptional opportunity for discerning buyers seeking refined coastal Florida living. Roof is 2017 (Tile) and A/C is newer (2023)

530 N Mac Ewen Drive, Osprey

$2,189,000

5 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

This exquisite 5 bedroom, 5.5 bath residence in The Oaks Clubside has undergone extensive structural, mechanical, and aesthetic upgrades over the past three years, significantly enhancing storm resilience, energy efficiency, outdoor living, and overall day-to-day living. Spacious and well planned, it offers room for loved ones, visiting guests, and live-in help or in-laws. The master suite is incredible, with his and hers bathrooms. Each side has its own vanity and toilet and provides access to the shared glass shower. Additionally, there is an office with pool view, making this area a true owner’s sanctuary. The upstairs areas are split. On one side, there are 3 bedrooms, one en suite. The other two bedrooms share a bathroom. Here you will find a deck with one of the four retractable awnings installed in 2024. On the other side, over the 3 car garage, and completely separate, you will find studio apartment. The huge, rescreened pool area has been updated with a built-in grill, new pool equipment and three retractable awnings and the pool was resurfaced and retiled. This home is a rare find, offering unparalleled upgrades and enhancements that make it a perfect blend of luxury and functionality. There are too many to describe here, but a complete list of upgrades is available. Don't miss the opportunity to own this exceptional home!

370 Sugar Mill Drive, Osprey

$1,700,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Accepting Backup Offers. Perfectly positioned on the 9th hole tee box within the Oaks community, this meticulously appointed estate offers a rare opportunity for a premier Sarasota golf course lifestyle. Designed for the discerning enthusiast, the property features panoramic fairway views and western exposure for breathtaking sunsets. The interior is defined by soaring vaulted ceilings, refined crown molding, & finishes throughout. The heart of the home is a curated chef’s kitchen featuring a bespoke butcher block island, professional-grade Viking double ovens, and sleek quartz countertops. High-end functionality includes dual KitchenAid dishwashers and custom cabinetry. The primary living spaces flow seamlessly to a wet bar and wood-burning fireplace, ideal for post-round entertaining. An extraordinary floating staircase of hand-built Hungarian wood leads to a versatile upper level with a private balcony overlooking the course. The primary suite serves as a sanctuary, entered through exquisite hand-carved doors imported from Turkey. This retreat features French doors leading to a private courtyard, custom walk-in closets, and a whirlpool jacuzzi tub. Outdoor living is centered around the pool and an expansive lanai with a fully equipped summer kitchen. Notable infrastructure includes a 3-car garage, three AC units, and clear hurricane shutters. This residence offers an elevated Sarasota lifestyle with immediate proximity to world-class golf and the exclusive amenities of the Oaks community. Please note membership of The Oaks is required.

401 Walls Way, Osprey

$699,000

The Oaks SubDv. ⋅ 34229 Zip Code

Exceptional opportunity to build your dream estate in The Oaks, one of South Sarasota’s most prestigious gated golf and country club communities. Situated on a rare cul-de-sac lot, this generous parcel offers privacy, mature landscaping, and an ideal canvas for a custom residence. Enjoy convenient access to world-class amenities including championship golf, tennis and pickleball facilities, a WellFit fitness center, swimming, croquet, dining venues, and an active year-round social calendar (club membership required). The Oaks’ prime location places you minutes from the renowned beaches of Siesta Key, upscale shopping, fine dining, cultural venues, and the vibrant lifestyle of downtown Sarasota. Don’t miss this rare opportunity to build in one of the Gulf Coast’s most coveted addresses. Lot size approximately 0.55 acres. Membership in The Oaks Club mandatory with homeownership. Buyer to verify all information.

410 Blue Garden Lane, Osprey

$2,189,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

**EXPERIENCE TIMELESS ELEGANCE AND EXCEPTIONAL CRAFTSMANSHIP** in this impeccably maintained Arthur Rutenberg custom residence, perfectly positioned on a private 0.61-acre homesite overlooking the Heron Golf Course with tranquil water views in the prestigious, 24-hour gated Oaks Club community. Nestled beneath a gorgeous oak canopy and enhanced by professional exterior landscape lighting, this remarkable 4,012-square-foot home offers the utmost in Florida living. Designed to maximize natural light, soaring 12-foot ceilings, expansive windows, and seamless indoor-outdoor living, the home was affectionately known by its previous owners as "The House of Light." From the dramatic circular driveway and lighted entrance columns to the elegant coffered ceilings, crown molding, and inviting gas fireplace, every detail reflects the quality and sophistication synonymous with Arthur Rutenberg. The thoughtfully designed floor plan features 4 Bedrooms plus Private Study/Den, 3 Full and 1 Falf Baths, centered around a spacious gourmet kitchen with new granite countertops, premium Sub-Zero and Wolf stainless steel appliances, and an open flow into the comfortable family room—ideal for both everyday living and entertaining. The luxurious primary suite offers a spa-inspired bath with dual vanities, a custom tiled walk-in shower, and a relaxing soaking tub. An oversized three-car garage provides abundant storage, a workbench, and an additional refrigerator. The expansive screened lanai is the true centerpiece of the home, offering the ultimate Florida lifestyle with generous covered entertaining space, multiple dining areas, and a stunning pool highlighted by a dramatic four-foot tiled waterfall feature. A fully equipped outdoor kitchen includes granite countertops, an Alfresco grill, refrigerator, and bar seating, creating the perfect setting for year-round entertaining. Meticulously updated throughout the years, significant improvements include hurricane-impact windows and doors (2020), roof (2019), pool cage/aluminum structure (2018), and numerous additional enhancements that preserve the home's exceptional quality and value. The Oaks Club is a member-owned private golf community with more than 40 years of excellence and is the only private residential golf club in the Sarasota, Bradenton, and Fort Myers region recognized by both Platinum Clubs of America and Distinguished Emerald Clubs of the World. Residents enjoy a magnificent 30,000-square-foot clubhouse, three exceptional dining venues, two championship 18-hole golf courses, outstanding golf instruction, a premier racquet program with 12 Har-Tru HydroGrid tennis courts and pickleball courts, croquet, bocce, basketball, a Junior Olympic swimming pool, and a newly expanded state-of-the-art wellness, fitness, and spa facility. Recognized as "The Healthiest Club" and an Audubon Society-certified community, The Oaks also welcomes families and offers an unmatched lifestyle. Ideally located in one of Sarasota County's most sought-after communities, this exceptional home is just minutes from world-renowned beaches, top-rated schools, fine dining, shopping, and Sarasota's vibrant arts and cultural attractions, making it a rare opportunity to enjoy luxury living in a truly prime location. **Enjoy Viewing the 3D Virtual Tour and Aerial Video*

433 E Macewen Drive, Osprey

$1,450,000

3 Beds ⋅ 5 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

OWNER SAYS SELL! No Reasonable offer refused on this home that is already the lowest price per Square foot on the market! COMPLETELY UPDATED IS NOT AN EXAGGERATION! This Bo MacEwen–designed 3-bedroom, 4.5-bath home has been updated from top (RE-TILED ROOF) to bottom, with new luxury flooring surfaces throughout and over $650,000 in renovations. No expense was spared in creating a refined, sophisticated residence that still feels warm and inviting. This home truly shows like new, and a full upgrade list is available upon request. Inside, the spacious layout includes a formal dining room, formal living room, and a cozy den with gas fireplace. Crown molding, tray ceilings, plantation shutters, and custom built-ins elevate the elegance throughout. Multiple sets of French doors open to the very private pool area, filling the home with natural light and enhancing indoor–outdoor living. The chef’s kitchen has been refreshed and features a six-burner Viking gas range with grill, Viking hood, Sub-Zero refrigerator/freezer, butler’s pantry, breakfast bar, and dining nook. The primary suite boasts two walk-in closets and a recent down-to-the-studs, resort-level bathroom remodel—one that would make even the Ritz envious. One guest suite occupies the west wing, while a spacious second-level suite adds comfort and flexibility. Significant structural upgrades include NEW low-E hurricane-impact windows and skylights, roll-down hurricane shutters (front and rear), and a whole-house generator for added peace of mind. Exterior enhancements include a NEW paver driveway and pool deck, extensive landscape lighting, and a very private pool area with new built-in grill and bar. Located in one of the Gulf Coast’s premier country club communities, The Oaks offers two championship golf courses, HAR-TRU tennis courts, pickleball, croquet, and a state-of-the-art WellFit Center. Club membership is required with homeownership.

76 Osprey Point Drive, Osprey

$1,285,000

4 Beds ⋅ 3 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Although built in the 20th century, this home looks as authentic as the French manor house it was modeled after. The façade features a soft, light-colored stucco exterior accented by rustic stonework, creating a warm and inviting presence. Gracefully arched windows and classic dormers enhance the wooden shingle roof, which is crowned by two stately chimneys that add to the home's old-world charm. A gently curved brick-bordered walkway leads through a beautifully landscaped front yard, where manicured shrubs and vibrant flowering plants frame the path to the entrance. Bathed in sunlight under a clear blue sky, the entire scene feels like a serene countryside retreat—refined, welcoming, and effortlessly picturesque. In the main house, you’ll find high ceilings throughout, two bathrooms, three bedrooms, a formal dining room, and a large, dedicated office. Separate from the main home is a large, one-bedroom casita with a vaulted ceiling, full bath, kitchenette, and room for a workspace. The huge, fully-screened, 1,000 SF courtyard is beautiful with a vaulted pool cage, pool with built-in waterfall and a spa, and both sunny and shady areas perfect for morning coffee, lunch, or evening cocktails. This home has everything to serve your needs, including those of multigenerational living and visiting guests. Step inside this courtyard style home and you will be greeted by a lovingly maintained, spacious, open floor plan interior. The high ceilings, skylights, and doors surrounding the courtyard ensure that every inch of the home is filled with light. The kitchen features a wide expanse of countertops including two sinks, a range with an ultra-quiet external fan range hood, and a dishwasher. Surrounded by maple cabinetry and including a built-in microwave and refrigerator, this space will bring the joy of cooking to a chef of any level. The master suite is huge and features two walk-in closets, and an incredible bathroom with clerestory windows, dual sinks in the main area of the bathroom and one in the water closet, a jetted tub and a separate walk-in shower. The two guest bedrooms within the main part of the house are good sized, and there is a large laundry room with a utility sink and new washer and dryer. Add to this all the practical features of A NEWER ROOF, IMPACT EXTERIOR FACING WINDOWS, RECENTLY REDONE POOL SURFACE AND EQUPIMENT, AND A 2 CAR GARAGE WITH TONS OF STORAGE SPACE, and you have everything you need to live an incredible lifestyle in The Oaks Bayside. Membership in The Oaks Club, Sarasota’s premier golf and country club, is mandatory with homeownership.

137 Osprey Point Drive, Osprey

$2,399,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, airy ambiance, while large windows frame stunning lake views, offering the perfect backdrop for the sparkling pool and expansive spa, complete with tranquil water features. With disappearing sliders throughout, the home can let the air and light flow easily from outside to in. Enjoy breathtaking sunsets from your private oasis or stroll a kayak or paddleboard to the nearby boat launch for effortless access to Sarasota Bay and the Gulf, thanks to the newly reopened Midnight Pass. Situated on a secluded .40-acre lot, this property offers a serene retreat, featuring a Zen garden surrounded by lush landscaping. Residents of The Oaks enjoy world-class amenities, including championship golf, fine dining, tennis, fitness, and swimming. At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance.

49 Osprey Point Drive, Osprey

$3,650,000

4 Beds ⋅ 7 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Nestled within the exclusive gated community of the Oaks Club in Osprey, Florida. This singular estate represents a masterful confluence of architectural refinement and modern luxury, encompassing nearly 7000 ft.² of conditioned living space, the residence has undergone an extraordinary transformation – reflecting an investment exceeding $1.5 million – to achieve a standard of craftsmanship seldom encountered in contemporary homes. The grand foyer reimagined with architectural restraint and elegance, opens to a series of impeccably curated, living spaces defined by scale, light and material integrity. The entire home has been freshly repainted, presenting a pristine, harmonious aesthetic that enhances the interplay of color, texture and light throughout. The kitchen rebuilt from its foundation up is a tour de force of design and function-anchored by bespoke ultra-custom cabinetry, expansive, quartz surfaces, and a suite of professional grade Thermador appliances. These include three wall, ovens a speed-cook microwave, an induction cooktop, dual dishwashers, two wine coolers, a U-line beverage refrigerator, and an impressive new side by side Thermador refrigerator and freezer. Every culinary and social experience is elevated by thoughtful details such as Newport Brass fixtures, elegant chandeliers, and an exceptional walk-in pantry that unite beauty and practical design. The primary suite embodies serene granuer, featuring a newly constructed bath with custom cabinetry, a sculptural freestanding tub, and dual shower-all finished in large format, porcelain tile. A remarkable walk-in closet includes a concealed storage and safe room, melding security with sophistication. Two additional bedroom suites have been fully redesigned with its own private bath, while a refined powder room enriches the main entry corridor. Throughout the home, state- of-the-art technology complements the elegant aesthetic, a newly installed security system with outdoor surveillance cameras, ensures peace of mind, while a Sonos sound system, integrates premium audio, seamlessly across living areas for both entertainment and ambience. Additional appointments include new hardwood flooring, freshly refinished and painted garage spaces with an epoxy-coated floor, and a large air-conditioned storage room with supplementary washer, dryer hook ups. The outdoor domain has been equally vitalized, showcasing, a newly remodeled pool, upgraded mechanical systems, and beautifully landscaped grounds that frame the home with natural grace and meticulous attention to detail. Residing within the Oaks Club, homeowners enjoy the exclusivity of one of Sarasota County’s, most distinguished country club communities renowned for its championship golf courses, fine dining, tennis and social amenities. This one-of-a-kind Eagle Watch Lane estate stands as a testament to discerning design, meticulous, stewardship, and enduring architectural grace.

691 Eagle Watch Lane, Osprey

$1,500,000

3 Beds ⋅ 5 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

**BEAUTIFULLY UPDATED COUNTRY CLUB ESTATE with Ideal Southern Exposure and WATER VIEW** is located in the COVETED, OAKS BAYSIDE Country Club Neighborhood on Little Sarasota Bay. Enjoy the Private and Tranquil, Lake-front setting of this Meticulously Maintained, Timeless residence with Stunning Architectural Detail as designed by Famed Architect, Bo MacEwen, who also designed the breathtaking Oaks Clubhouse. Featuring 3 EN SUITE BEDROOMS, 4 FULL and 1 HALF BATHS, this Open and Split Floorplan offers generous gathering areas. The recently renovated, Light and Bright Country French Kitchen is a chef’s delight, featuring a large island with counter seating, premium stainless steel appliances, stone counters, hardwood cabinets, ample storage including walk-in and closet pantries, etc. The Spacious Primary Bedroom suite features a lovely wall of windows with beautiful lake view, multiple walk-in closets, dual vanities, custom-tiled shower and soaking tub. Custom details include crown moldings, wainscoting, hardwood, tile and engineered hardwood flooring, many built-in features, fireplace etc. French doors from most rooms lead to the screened lanai which overlooks an expansive lake in a serene setting. The Oversized 2-Car Garage features EV Charging and adjacent workshop/storage. Architectural POOL Design is available. THE OAKS-BAYSIDE is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World - where amenities include two, 18-hole championship GOLF courses, award-winning TENNIS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL. The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

325 Osprey Point Drive, Osprey

$1,850,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Set an appointment to experience this thoughtfully designed Arthur Rutenberg home, where craftsmanship and details are truly on display. Upon entering through the double door entrance, the quality and attention to detail are immediately evident. Situated on a 1/2 acre + "premium" golf course lot strategically positioned on the Heron Course (hole 5). This residence blends timeless design with modern comfort across 4,192 square feet of living space. The kitchen features an impressive island range, high-end finishes, and quality appliances, perfect for everyday living or entertaining. Enjoy the expansive outdoor living area complete with an outdoor kitchen, pool & paver deck with ample undercover space, and impact-rated hurricane windows providing peace of mind and energy efficiency. With 4 generous sized bedrooms, 3.5 baths, and a large study. In this home, every space feels intentional, inviting, and connected to its surroundings with easy access to local conveniences. The Oaks is an amenity rich community. It has something for everyone - golf, tennis, pickleball, pool, fitness facility, dining, bar service, and many social opportunities.

453 E Macewen Drive, Osprey

$1,750,000

4 Beds ⋅ 5 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

**STUNNING GOLF COURSE ESTATE with WATER and GOLF COURSE VIEW in the Highly Sought-After OAKS COUNTRY CLUB Community** with Ideal Southern-Exposure and View across the 15TH Green of the interior, HERON GOLF COURSE. With its delightful curb appeal and gorgeously manicured landscape, this residence offers 4 EN SUITE BEDROOMS + Study/Den, 4 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Plantation Shutters, Gas Fireplace, Spacious Kitchen with New QUARTZ Counters and Stainless Steel appliances including premium brands such as SUBZERO and FISHER PAYKEL, 3-Car Garage, and much more! An Expansive Primary Bedroom Suite features multiple walk-in closets, dual vanities, soaking tub and custom-tiled shower. Ultimate enjoyment of the outdoors is made possible with an expansive screened lanai featuring a Heated Pool & Spa, Outdoor Kitchen and ample entertaining space in a private and serene setting. Recent UPDATES include NEW ROOF (JULY, 2023), QUARTZ COUNTERS, INTERIOR PAINT, LANDSCAPING AND OUTDOOR LIGHTING, NEW HOT WATER TANK, etc. The Oaks is a distinguished, 24hr guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership.

627 N Macewen Drive, Osprey

$789,000

3 Beds ⋅ 2 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Looking for a home you can truly fall in love with? Your search ends here. This thoughtfully updated, impeccably maintained 3 bedroom, 2 bath residence in The Oaks Preserve offers the perfect blend of comfort, style, and privacy. And you can BUY WITH CONFIDENCE — THE PROACTIVE SELLERS HAVE COMPLETED INSPECTIONS IN ADVANCE TO SHARE WITH BUYERS, GIVING YOU CLARITY FROM THE START. No guessing…what you see, and what you don’t see, is what you get! From the moment you arrive at the pavered driveway, the pride of ownership is unmistakable. Double leaded-glass front doors open to a light-filled interior designed for effortless Florida living. Just off the entry, a dedicated home office features plantation shutters and a ceiling fan. The formal dining room showcases a decorative ceiling and a beautiful built-in buffet with glass-front cabinetry. The open kitchen features new granite countertops, stainless appliances, a breakfast bar, chef’s desk, and built-in wine and beverage cooler. The adjoining breakfast nook with an aquarium window, overlooks the sparkling pool and spa. The master suite is exceptionally spacious, offering a sitting area with built-in window seat and large walk-in closets with glass-front storage. The updated en suite bathroom has granite countertops, dual sinks, a soaking tub, separate shower, and marble accents. Two well-sized guest bedrooms provide generous closet space, and the updated guest bath includes granite and marble finishes. The air conditioned 2-car garage with epoxy flooring offers abundant storage. This home backs to a lush, tropical preserve, ensuring privacy for the pool and spa. The lanai features two distinct areas: a large, covered space with outdoor kitchen and ceiling fan for shaded dining, and a sun-splashed pool and spa area under a screened enclosure. You can also enjoy the nearby Bishopscourt community pool. With mandatory membership, this home offers access to all of the amenities being a member of The Oaks has to offer. There is currently no waiting list for either Golf or Sports/Social membership

21 Bayhead Lane, Osprey

$2,625,000

4 Beds ⋅ 7 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Welcome to your dream home, a sanctuary of elegance and comfort nestled on an exclusive, private street with only nine residences and no neighbors across the way—just the tranquility of a natural preserve. This remarkable property in The Oaks Clubside, with 4 bedrooms, 5 full bathrooms, and 2 half baths, boasts impact windows and doors throughout, providing peace of mind and a quiet, secure environment. Step inside to discover an open floor plan adorned with a blend of rich wood and luxurious travertine floors. Each of the large bedrooms is an en suite retreat, offering privacy and comfort for residents and guests alike. On the first floor you will find a huge master suite, with his-and-her closets, and a luxurious master bathroom that has two separate vanities, a walk-in shower and soaking tub. The two additional bedrooms are generously sized. The open kitchen features cherry wood cabinets, a granite island and high end stainless steel appliances. The breakfast nook is flooded with natural light and offers a lovely view over the pool. The second story has a fourth en-suite bedroom, and balcony overlooking the golf course and lake. And, for those who love to entertain, the game and media room is designed for fun gatherings of friends. The heart of the home extends outdoors, where you will find an impressive outdoor kitchen area perfect for grilling and dining alfresco. Enjoy a beautiful, long view of the Heron #14 and the serene lake beyond—a panoramic scene that will take your breath away every day. This home is loaded with thoughtful additions, including three new exterior ceiling fans for comfort on warm days, custom office closet shelving and a secure dog run fence for your furry friends. The garage boasts a durable epoxy floor and hurricane-rated doors. Additional upgrades abound with 4 new AC units with UV lights for optimal air quality, a new roof, two-stage pool pump and new irrigation pump, new tankless Navian water heater to name a few. You absolutely must see this home to appreciate all it has to offer. Membership in The Oaks Club, Sarasota’s premier golf and country club is required with home ownership.

478 Oriskany Court, Osprey

$2,395,000

3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, and much more! An Expansive Primary Bedroom Suite features a Bonus Room, Walk-In Closet, dual vanities, soaking tub and custom-tiled shower. Enjoy OUTDOOR LIVING at its FINEST in an Expansive, Screened Lanai with PEBBLETEC Pool & Spa and Outdoor Kitchen in a serene setting. ROOF (2015). THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **Please Enjoy Viewing the 3D VIRTUAL TOUR**

852 Macewen Drive, Osprey

$799,000

3 Beds ⋅ 2 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered driveway, and hurricane-rated patio and bedroom doors. All living areas have wood floors or Italian porcelain tile. The kitchen features a gas stove, Waterworks faucet, quartz countertops, modern stainless appliances, and solid wood cabinetry. The breakfast nook adjacent to the kitchen has aquarium glass windows offering a view of the pool and foliage. The family room glass doors stack behind the wall, providing views of the pool and preserve, and they are hurricane-rated. The owner's suite includes two walk-in closets, a linen closet and space for a sitting area or office. Hurricane-rated glass doors overlook the pool. There is a separate study/office/bedroom with built-in wood cabinetry and space and wiring for a media room. The guest suite has an ensuite bath updated with Quartz counters and a vessel sink. Enjoy the utmost in outdoor living with a stunning, PebbleTec POOL with Travertine deck while there is ample space for a spa or additional seating within the spacious screened lanai. Connections for an outdoor kitchen are also available. A beautiful new pavered driveway adds that special curb appeal. In addition to the metal, roll down hurricane shutters, there is an electric hurricane protective screen spanning the lanai area to protect outdoor furniture. The extra deep two car garage affords additional storage options. A collection of unique bougainvillea and crepe myrtle rounds out the gardens. This lot is located outside the FEMA flood zone Bishops Court in The Oaks Preserve is a 24-hour guard-gated community with walking and biking paths. Additionally, there is a year-round heated community pool nearby. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **PLEASE ENJOY VIEWING the 3D VIRTUAL TOUR**

13 Bayhead Lane, Osprey

$1,600,000

5 Beds ⋅ 8 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Situated on a double lot behind the secure gates of The Oaks, this two story 5 bedroom home, with 7.5 bathrooms, boasts fantastic potential and excellent bones. The only thing it needs is for you to put your personal touch on it and make it your own. As you pull up to this home, using the front circular driveway, or the back driveway with access to the 4 CAR GARAGE, you will immediately be taken with its classic lines. With its spacious layout and thoughtful design, this property is a hidden gem for those who love to entertain. With so much space, and every bedroom having its own en-suite bathroom, there is room for your loved ones and to host visiting guests, preserving privacy for all. Downstairs you will find a formal living room and an expansive family room with fireplace, built-in shelving, ceiling fan and numerous doors filled with natural light. The large open kitchen has everything the home chef could possibly need to create incredible edibles. Casual meals can be taken in the adjoining breakfast nook, or you can serve a formal feast in the large dining room with built-in cabinetry and a wet bar just outside. The master suite is huge featuring a dedicated sitting area, and his-and-hers master bathrooms. Completing the first floor is a guest bedroom a large office or library with built-ins and a powder room. Upstairs you will find 3 more en-suite bedrooms. One of which is off the back stairway and would make a great guest suite or private room for live-in help. Outdoors, the landscaped double lots, surrounded by a low wall, provides a tropical sanctuary. Here you will find an enormous, screened lanai, that is an entertainer's paradise. A sparkling pool, spa, expansive patio, and an outdoor kitchen set the stage for al fresco living at its finest. Whether enjoying serene sunsets or hosting vibrant soirées, this home will help you create unforgettable memories with friends and family. Membership in The Oaks Club is required with homeownership. With two distinctly unique 18-hole championship golf courses, 12 HAR-TRU tennis courts (4 lighted), croquet and pickle ball courts, a state-of-the art fitness center, fine and casual dining options, and a wealth of social events, The Oaks is truly Sarasota’s premier golf and country club.

916 Macewen Drive, Osprey

$1,325,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Welcome to timeless elegance and modern comfort in The Oaks Clubside. This stunning 4-bedroom plus den/office, 3.5-bath home, built in 2014 by Todd Johnson Homes, blends country modern style with refined sophistication. Situated on an oversized .64-acre corner lot, this courtyard-style residence is designed for effortless Florida living. Step through grand double wood doors into an inviting space where soaring ceilings, an open floor plan, and abundant natural light create an airy, welcoming ambiance. The home features tile and hardwood floors, hurricane impact windows and doors, a spacious 3-car garage, and thoughtful architectural details throughout.The gourmet kitchen is a chef’s dream, offering stainless steel appliances, a breakfast bar, and a cozy eat-in nook that opens seamlessly to the family room—complete with a fireplace for added charm. A private casita with its own entrance and full bath offers incredible flexibility—ideal for hosting guests, a home office, or a personal studio retreat. Nestled on a serene lakeside lot, the outdoor living spaces are equally impressive. Enjoy peaceful water views from the privacy of your courtyard pool and spa. Relax under the expansive covered patio or soak up the sunshine from the open-air seating area as you unwind in the tranquility of your surroundings. More than just a home, this is a lifestyle. Ownership includes mandatory membership in The Oaks Club, Sarasota’s premier golf and country club. Enjoy two championship golf courses, a top-tier tennis program, state-of-the-art WellFit center, fine dining, and a vibrant calendar of social and recreational activities—all in the heart of South Sarasota.

402 Walls Way, Osprey

$1,405,000

3 Beds ⋅ 5 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

One or more photo(s) has been virtually staged. It is rare to find such an incredible combination of privacy and spectacular views as you will find in this 3 bedroom, 4.5 bath home. Located on a quiet dead-end street in The Oaks Bayside, the traditional design marries beauty with functionality. Step inside and you will be greeted by light-filled space with classic motif. Large windows flood the entire home with natural light. As you explore the interior you will find everything you need to live an incredible, luxury lifestyle. The formal living room features French doors to the lanai, a gas fireplace and built ins. The view from this room is lovely. The kitchen, with tons of neutral cabinetry and miles of counterspace, opens to breakfast area with large windows and a door to the exterior. There is also a full, formal dining room. The master suite is a sanctuary of tranquility, featuring a spacious bedroom, walk-in closet, and an en-suite bathroom with a soaking tub and separate shower. All of the other bathrooms are en-suite as well, and there is a full pool bath, and the guest bath . A dedicated home office provides a quiet retreat for study or work and there is a large laundry room with a window, utility sink, counters and a huge amount of storage space. The outdoor living area is just as incredible, with a large Travertine lanai, a spa, and a pool with new Pebble Tech pool surface, and the pièce de résistance, NEW CLEARVIEW SCREENS, offering drop-dead gorgeous views looking down the lake. The lanai also has KEVLAR HURRICANE AUTOMATIC ROLL DOWNS. Add to this A NEW ROOF, IMPACT WINDOWS AND DOORS, NEW HVAC. This luxury home is more than just a residence; it’s a harmonious blend of beauty, comfort, and functionality, waiting for you to come, add your unique style and make it your own. The Oaks Bayside is located on the west side of Tamiami Trail, on the banks of Little Sarasota Bay. Surrounded by Historic Spanish Point and conservation land, it enjoys a tranquil, natural setting. There is a community dock for use by residents; fish, launch a kayak or just sit quietly and watch the daily show of glorious color put on by the evening sunsets. The Oaks Club has two golf courses, a driving range, 12 HAR TRU tennis courts (4 lighted), 4 pickleball courts, croquet court, a WellFit center, and 3 onsite restaurants. Club membership is required with homeownership.

282 Shell Midden Court, Osprey

$950,000

3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Divine is in the details of this lovely 3 bedroom, 3 ½ bath professionally redesigned home in the Oaks Preserve. No need to be concerned with remodeling, as this home underwent a complete renovation in 2023. This exceptional property meets the demands of today’s discriminating buyer, with a spacious chef’s gourmet kitchen featuring top of the line stainless appliances, a large prep island, quartz countertops throughout, and an open concept for ease in entertaining. The family/gathering room is large enough for dual seating areas, and has a panoramic view overlooking the lanai, and a serene vista of the lovely oaks and lake with a fountain. The separate dining room has French doors, and is a sizeable space for a large table. The living room has beautiful views of the outdoors allowing natural light. The Owners’ suite also has direct access to the lanai, and the Owner’s bath is a spa-like oasis with a free standing soaking tub, separate shower and large dual vanities with quartz counters. Two guest bedrooms have en suite baths and are private for visiting family and friends. Custom finishes include 24x24 porcelain floors that span the residence, plantation shutters, custom recessed lighting, tons of built-in storage cabinetry with pull out drawers, solid wood doors, new paver driveway, new roof, and an epoxy finished floor in the two-car garage with additional storage. The lanai is perfect for al fresco dining with room for a large table and an additional seating area. No need to worry about maintaining a pool, as the neighborhood pool is steps from the home. Residents walk and bike the neighborhood, and there are social gatherings frequently at the pool house. The Oaks Country Club is one of the finest in southwest Florida, offering two 18 hole championship golf courses, 12 HarTru tennis courts, pickleball, a regulation croquet lawn, a variety of dining options from casual to gourmet, men’s and women’s clubs, and an abundance of social activities throughout the year. Membership is required, either social or golf, and The Oaks is centrally located, minutes to downtown Sarasota, the beaches, arts and shopping. This home is a must see.

32 Bayhead Lane, Osprey

$1,850,000

5 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

This stunning 5 bedroom, 4 bath residence, custom built by Wetherington, epitomizes refined living and sophisticated elegance. Nestled in The Oaks Clubside, it enjoys an incredible private setting, with no house or neighbors on one side. This home is large and spacious, with timeless design elements, creating an exquisite sanctuary. As you enter through the double leaded glass front doors, the open formal dining area is on your right. In front of you, the elegant formal dining room with fireplace, and a lovely view out to the pool. As you explore, you will be impressed by all the details you find throughout, tray and coffered ceilings, built-ins, unique ceiling fans and lighting fixtures, plantation shutters and tile work. The kitchen earns a chef’s kiss. Here you will find everything the home gourmet needs to create stunning meals with enough space to enjoy them with guests at the adjourning eat-in area. There are two master suites, connected by a spectacular bathroom, reminiscent of space you would find in a five-star hotel. The walk-in closet is huge with built-in features. The interior of this home is so inviting you may not want to leave. However, once you step outside your breath will be taken away. You will find an amazing addition to the inside, a fabulous outdoor family room, complete with fireplace and kitchen area. Covered, this is the perfect spot to enjoy some shade on a sunny afternoon, or to cozy up on a cool Florida evening. Completing the outdoor space is a pool and spa surrounded by a pavered deck large enough for you to lay out and bath in the sun! Outside of the lanai, lush vegetation surrounds the back of the house, affording you the utmost privacy. The words MUST SEE were never more accurate. To see this home is to fall in love with it. The Oaks Club, Sarasota’s premier golf and country club, has two 18-hole championship golf courses, 12 HAR-TRU tennis courts maintained to tournament standards, 4 of which are lighted, bocce and pickle ball courts, a junior Olympic community pool, and a wide variety of dining, recreational and social offerings. Membership is required with homeownership.

855 Macewen Drive, Osprey

$1,400,000

3 Beds ⋅ 3 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Beautiful lakefront 3 bedroom, 3 bath home in The Oaks Clubside with view of the Eagle 3. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options. Membership is required with homeownership. INITIATION FEES GOING UP ON 2/1/2025. BUY NOW BEFORE THE INCREASE!

378 Macewen Drive, Osprey

$2,100,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Bathed in natural light, with highly sought after southern lanai exposure, is this stunning and meticulously maintained custom built John Cannon home in The Oaks Clubside. With 4 bedrooms, and 3 full and one half bathrooms, there is room for loved ones and guests, making it ideal for grand entertaining or peaceful and serene poolside relaxation. Enter through the elegant custom etched glass front doors into the bright and airy marbled floored foyer. This gleaming expanse of marble highlights a glamourous formal dining room and a formal living room with fireplace. The chef’s kitchen boasts exotic granite, custom cherry cabinets, Thermador appliances, reverse osmosis water system, and multiple pantries for ample storage. The extraordinarily spacious and tranquil master suite features French doors leading onto the sun-lit lanai. The master suite offers dual custom California closets with a bonus custom floor-to-ceiling wardrobe room. The luxurious spa-like master bath has his and hers private water closets, a free standing bathtub, his and hers sinks, and a vanity area all with marble counter tops. The large, upgraded laundry room features custom cabinets with granite countertops and an additional free-standing refrigerator and freezer. Experience the relaxing ambiance of the outdoor lanai with a cozy firepit, lighted water bowls, whole house surround sound, and a saltwater pool providing perfect tranquility. The lush tropical landscaping, with vibrant flower beds overflowing with blooms, creates a welcoming, idyllic tropical setting. Add to the abundant touches and lovely aesthetics, such as elegant chandeliers throughout the home, practical and useful features like a Control 4 wired smart home system, WHOLE HOUSE 20KW GENERATOR, a 3-car garage with custom cabinets, overhead storage and finished flooring, and hurricane protection shutters, and you know you have found the perfect place to live the country club lifestyle on Florida’s gorgeous Gulf Coast. You will delight in this graceful, inviting home. Membership in The Oaks, Sarasota’s finest golf and country club, is required with homeownership. With two distinctly unique 18-hole championship golf courses, 12 HAR-TRU tennis courts (4 lighted), croquet and pickle ball courts, a state-of-the art fitness center, fine and casual dining options, and a wealth for social events, The Oaks is truly Sarasota’s premier golf and country club.

703 Macewen Drive, Osprey

$1,280,000

3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

**BEAUTIFULLY RENOVATED, GOLF COURSE ESTATE, IDEALLY LOCATED** in the Coveted “Saint James Park” Cul De Sac neighborhood, offers Close Proximity to The Oaks Country Club and Amenities. Overlooking the Eagle Golf Course and Boasting 3 EN SUITE BEDROOMS with Private Balconies (including Two Primary Bedrooms, 1st and 2nd Floors) and 3 FULL and 1 HALF BATHS, this charming residence is priced BELOW APPRAISAL and features a NEW KITCHEN with built-in Wine and Coffee Bar, impressive Marble and Newer Hardwood Flooring, HURRICANE IMPACT Windows and Sliding Doors, Two NEW HVAC units (2023), NEW ROOF (2020) and So Much More! Detailed Feature & Upgrade List is available upon request. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR**

219 Saint James Park, Osprey

$1,595,000

3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious Kitchen with Granite Counters and Stainless Steel appliances, 2-Car Garage w/ Circular Driveway, and much more! An Expansive Primary Bedroom Suite features multiple walk-in closets and an Updated Primary Bathroom with dual vanities, soaking tub, custom-tiled shower and private outdoor shower. Ultimate enjoyment of the outdoors is made possible with an expansive screened lanai featuring a Large 45ft Pebble-Tec Pool & Spa, Outdoor Kitchen space (without appliances) and an abundant covered seating area. Recent UPDATES include Freshly Painted Interior (2024), NEW POOL CAGE (2023), NEW ROOF (2018), HVAC (2018), Pool Pump, etc. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

909 Macewen Drive, Osprey

$2,400,000

5 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

WELCOME HOME - NO STORM DAMAGE AT THIS PROPERTY (ELEVATION / OVERALL BUILD) ~ THE OAKS COUNTRY CLUB - SARASOTA, FL. THIS HOME @ #425, BOASTS BEAUTIFUL GOLF COURSE AND SELECT WATER VIEWS THROUGHOUT. A 27,000 SF +/- PRIVATE LOT. ONE CAN LOOK DIRECTLY AT THE PAR 3 - 4TH HOLE (THE OAKS HERON COURSE). MATURE STUNNING LANDSCAPING SURROUNDS THE PROPERTY. THE HOUSE OFFERS A TOTAL OF 5,100 SQUARE FEET OF RANCH-STYLE LIVING, 5 BEDROOMS, 5 BATHROOMS WITH AN ADDITIONAL 1/2 BATHROOM. A SEPARATE GUEST SUITE WITH LIVING AREA AND SEPARATE ENTRANCE IS INCLUDED, PERFECT FOR VISITORS, GUESTS, OR A SECOND OFFICE SUITE. SOME OF THE UPDATED FEATURES INCLUDE BUT ARE NOT LIMITED TO AN OPEN FLOOR PLAN, UPDATED GOURMET KITCHEN, GAS FIREPLACE (MASTER / LIVING), ALL EN SUITE BEDROOMS, SLIDING POCKET DOORS, COFFEE BAR, SOAKER TUB, MARBLE FLOORS, GLASS SHOWERS, GRANITE COUNTERS, OUTDOOR BAR AND KITCHEN, SPACIOUS MASTER SUITE, UPSTAIRS BONUS ROOM WITH BATH AND TERRACE OVERLOOKING THE GOLF COURSE AND WATER. THERE IS ALSO A SEPARATE PRIVATE OFFICE/DEN AREA, AN EXPANSIVE POOL AREA - COVERED AND OPEN, AND RECENTLY UPDATED HURRICANE WINDOWS AND DOORS, INCLUDING A STUNNING CUSTOM-MADE CAST IRON FRONT ENTRANCE FLOOR-TO-CEILING DOOR. THE ROOF SYSTEM HAS BEEN UPDATED, THREE NEW A/C SYSTEMS, NEW POOL PUMP, WATER BOOSTER FOR EVEN PRESSURE THROUGHOUT, MEDIA ROOM WITH 85” SMART TV WITH SONOS, NEW SAMSUNG WASHER / DRYER SYSTEM, 240 VOLT CAR CHARGING, UPDATED OUTDOOR KITCHEN WITH FRIDGE, OUTDOOR LIGHTING, NEW POOL CAGE, WATER SOFTENING SYSTEM, DOUGLAS BLINDS WITH REMOTE, AND A NEW POOL HEATER WITH A PHONE APP; THE PROPERTY IS VERY CLOSE TO THE CLUBHOUSE AND ALL THE FIRST-CLASS AMENITIES, INCLUDING GOLF, TENNIS, FITNESS, RESTAURANTS, POOL, COMMON AREAS, CROQUET, AND SOCIAL EVENTS. THE OWNER HAS UPDATED ALL THE HOME AND PROPERTY INSPECTIONS TO INCLUDE BUT NOT LIMITED TO 4-POINT AND WIND MITIGATION REPORTS FOR INSURANCE. THE OAKS CLUB HAS BEEN AWARDED THE PLATINUM CLUB OF AMERICA DESIGNATION. OUTSIDE THE PRIVATE GATES, THERE IS ACCESS TO ALL THAT THE SARASOTA AREA HAS TO DELIVER, INCLUDING SIESTA KEY BEACH, DOWNTOWN ARTS, UTC SHOPPING AREA, LIDO BEACH, NOKOMIS BEACH, AND THE SARASOTA HOSPITAL SYSTEM. THERE ARE ALSO LEADING PUBLIC AND OTHER SCHOOL OPTIONS, SUCH AS PINE VIEW SCHOOL (#1 IN FLORIDA / #18 NATIONALLY) AND OUT OF DOOR ACADEMY. PLEASE REFER TO THE UPDATED VIRTUAL PROPERTY TOUR AND HD PHOTOS. WE LOOK FORWARD TO YOUR VISIT! NOTE: THE OAKS CLUB MEMBERSHIP IS REQUIRED - PLEASE REFER TO CLUB DOCUMENTS FOR DETAILS.

425 E Macewen Drive, Osprey

$717,500

3 Beds ⋅ 3 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Classic Spanish Mediterranean 3 BR, 3 BA home in The Oaks Bayside. Club membership is required with homeownership.

519 Fernwalk Lane, Osprey

$1,850,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Welcome to your dream home in The Oaks Clubside. Incredible curb appeal will be your first impression of this 4 bedroom (plus office) home with 3 full and one half baths. With a pavered walkway, circular driveway, and lovely landscaping you are beckoned to enter and explore all this Rutenberg built Carlisle model has to offer. Walk through the double doors with leaded glass and you will immediately be impressed by how obviously special this home is. Tastefully updated and impeccably maintained, every detail is designed to delight. The formal living room is a study in elegance. The open kitchen is perfectly designed. It has new appliances, a wide expanse of counter space, beautiful cabinetry, unique ceiling with lighting and a center island cooktop. Opening on one side to the den with fireplace and built-ins, it has a small breakfast bar and a breakfast nook with an amazing view out to the pool area. With a formal dining room, wet bar and butler’s pantry, this home allows you to engage in all manners of entertaining, from causal meals to exquisite formal dinner parties. The master suite is huge, with a sitting area, doors to the lanai and an ultra large and luxurious bathroom. The office with built-ins, guest bedrooms and beautifully updated baths are all spacious; this house truly lives large. Step out back and your delight with this home will be doubled. Extensively renovated, this space is truly made for Florida living. The large, covered areas provide room for dining al fresco, or just sitting and visiting with friends in the shade. There is also plenty of room to bask in the sun on the huge pool deck, and the gorgeous pool and spa beckons you to splash away a tropical afternoon. Situated on the 5th hole of the Heron, the views from here are pretty in the daytime and gorgeous as the sun sets. If you are looking for an immaculate home that is ready for you to move in and begin living an enviable country club lifestyle, you have found it! The Oaks Club, Sarasota’s premiere golf and country club, has two championship golf courses, tennis and pickleball courts, a Junior Olympic community pool, a state-of the-art wellness center, and a wide variety of recreational and social activities. Located in south Sarasota, the community is minutes from nationally ranked Pine View School, and close to the Legacy Bike Trail, world renowned area beaches and all the shopping, dining and cultural offerings of downtown Sarasota.

451 Mac Ewen Dr, Osprey

$1,200,000

4 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

You won’t find a home like this elegant 4 bedroom, 5.5 bath beauty every day. Situated on a beautiful lot in The Oaks Clubside, it offers privacy and stunning views overlooking the lake out to the #7 of the Heron Course. The quiet street ends in a cul-de-sac. Inside you will find a spacious floor plan that is anything but cookie-cutter. This home has a 4th bedroom above the garage, perfect as a private quarter for live-in help or as a guest suite, or even a child’s wing. Add to this a 500 sq ft air-conditioned multi-use studio off the garage! The floor plan is open and spacious. All the main rooms downstairs open directly onto the lanai. The kitchen has a light filled eat-in area, and there is a separate dining room for larger, more formal meals. The family/TV room directly off the kitchen features a fireplace and oversized windows, making this a comfortable, cozy gathering space both day and night. The large master suite has room for a sitting area, and a bathroom with water closet, soaking tub and separate shower. Walk out to the lanai and you will find an ample covered area with ceiling fans, huge inground pool and spa, and those to die for views. Don’t miss the opportunity to own this one-of-kind offering and become a member of Sarasota’s premier golf and country club. Membership is required with homeownership. INITIATION FEES GOING UP ON 2/1/2025. BUY NOW BEFORE THE INCREASE! The Oaks has two 18-hole championship golf courses, 12 HAR-TRU tennis courts maintained to tournament standards, 5 of which are lighted, bocce and lighted pickleball courts, a club pool, and a wide variety of dining. NEW ROOF 2022.

639 Eagle Watch Lane, Osprey

$2,900,000

5 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Situated at the end of a cul-de-sac behind the gates of The Oaks, this 4 bedroom home w/1 bedroom guest house has 2 offices, four full and two half baths, exudes warmth and charm. Beautifully set on a 26,000 ft2 verdant lot, the rich vegetation gives the home a feeling of calm, tropical privacy. Meticulously maintained and beautifully updated, this home is perfect for every-day-living, and entertaining. The center island kitchen features quartz countertops. Plan your meals at the built in chef’s desk or work on your laptop as your loved ones sit at the breakfast bar at the start of a busy day. Or enjoy your first cup of coffee in the breakfast nook, with large aquarium windows, and look out on the lovely pool with pavered deck, and the lush landscaping beyond. The family room, just off the kitchen, has pocket sliders to the poolside covered terrace. The formal living with fireplace, and dining room, also open to the terrace. The spacious and luxurious master suite, and two guest suites are located on the first floor. Upstairs you will find a large bonus room, with private terrace, that has the potential to be used in any number of ways. Will it be your library, study, studio, or used as another bedroom suite? The possibilities are endless. The one bedroom guest cottage has a private entrance, living room and kitchenette and views of the two lakes. A covered outdoor kitchen completes this lovely home. The recently installed back fence gives you peace of mind for your children and pets. Membership in The Oaks, Sarasota’s premier golf and country club, is required with home ownership. Featuring two championship golf courses, lighted pickleball courts, 12 HAR-TRU tennis courts (5 lighted), a state-of-the-art fitness center, croquet lawn, and a vast array of dining and social options, the Oaks is situated close to the gorgeous local beaches, and all the shopping, cultural and recreational offerings of Downtown Sarasota.

388 Bunker Hill, Osprey

$1,590,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

One or more photo(s) has been virtually staged. Located behind the gates of The Oaks, on a quiet cul-de-sac, this 4 bedroom home with 2 full and 2 half baths, is situated on a lovely lot with Southern exposure. Enter through the front door and you will be welcomed to a great floor plan that is ideal for entertaining as well as the quiet enjoyment of those residing in this spacious home. The kitchen is huge and offers a large eat-in area, tons of cabinets, a built-in chef’s desk and large windows that flood the area with light. The master suite is oversized and has room for a sitting area, a door to the lanai and pool and big walk-in closets. There are three additional bedrooms. The split floor plan allows for room and privacy for your loved ones and guests. With a formal living room and dining room, and a den with fireplace there are so many places to gather with friends. Outside the screened lanai is a wonderful extension of the house. With a fountain, pool and spa it celebrates the tropics in design, and yet offers a good deal of covered areas to enjoy the shade. The views from here, down the length of the #2 Heron, are phenomenal. The Oaks, Sarasota's finest golf and country club, has two distinctly unique 18-hole championship golf courses, 12 HAR-TRU tennis courts (4 lighted), new pickle ball courts, a state-of-the art fitness center, fine and casual dining options, and a wealth of recreational activities and social events. Membership is required with homeownership.

935 Blue Heron Overlook, Osprey

$2,400,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Big views across the lake to 12th fairway of the Heron golf course adorn this Rutenberg built home. This home features 4 bedroom plus office with large rooms volume ceilings and crown molding throughout. Executive office is complimented with built-in cabinetry and hardwood flooring. The Master suite boasts a large bath with new glass shower door, 2 walk-in closets and large sitting area overlooking the lanai and pool area. The Oaks, Sarasota's premier golf and country club, features two 18-hole championship golf courses, 12 HAR-TRU tennis courts maintained to tournament standards, 4 of which are lighted, bocce and pickle ball courts, a junior Olympic community pool, and a wide variety of dining, recreational and social offerings. Membership is required with homeownership.

406 Walls Way, Osprey

$1,775,000

4 Beds ⋅ 5 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

This 4 bedroom, 4.5 bath home in The Oaks Bayside has been continuously updated and redecorated over the past several years, making it a pristine, elegant showcase. This is the perfect home for the refined country club lifestyle you seek to live. As you enter the new paver circular driveway, with three car side entry garage, it is evident how special this house is. Ideally situated on a private lot that backs to the Eagle Preserve, the front exterior immediately attracts you and draws you in. As soon as you enter you will be impressed with the decorated interior, from custom paint to new wood floors everything is carefully crafted to combine elegance and warmth. A 2020 redecoration/upgrade project, at a cost of just under $200,000, includes new lighting fixtures and new ceiling fans (inside and out), the addition of wainscoting in the foyer, dining room and powder room, custom drapes, Gracie wallpaper in the foyer and NEW SECURITY SYSTEM, POOL GATES, SCOTSMAN ICE MAKER AND WINE COOLER, as well as an audio-visual upgrade to include speakers in the living room and porch and surround sound in the living room. Large windows and glass doors, two fireplaces and custom lighting keep the interior light and bright, day and night. And speaking of night, stepping out onto the paver patio at twilight is truly a lovely experience. The open-air pool WITH NEW HEATER and spa looks out onto gorgeous grounds WITH COMPLETELY NEW LANDSCAPING, accented by beautiful NEW exterior lighting. Sit and enjoy a perfect Florida evening, as the sunset paints the sky in the west. Back inside you will be thrilled by everything you see, including a master suite with walk-in closet and new carpet, marble steam shower w/6 heads, wood vanities with granite counters, and the relaxing view of the private walled garden from the master bathtub. There is so much more to love about this house, including rebuilt chimneys, new insulation in the house and garage, whole house water filtration system and a new roof in 2019, you absolutely must explore it and see all the ways this is the personification of your dream home on Florida’s gorgeous Gulf Coast. The Bayside of The Oaks has a community dock, gazebo and reflecting pool. Clubside you will find two championship golf courses, 12 HAR-TRU tennis courts (4 lighted), pickleball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and a wide variety of dining and social options. Club membership is required with homeownership.

165 Sugar Mill Drive, Osprey

$3,915,000

4 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

**EXQUISITELY DESIGNED ESTATE BOASTS MODERN & CONTEMPORARY ELEGANCE** This FULLY UPDATED Residence features a MAIN HOUSE with 3Beds/4.5Baths plus GUEST HOUSE (1Bed/1Bath, Kitchen/Laundry, Living area) and is situated on an Oversized, Private and Serene DOUBLE LOT in the SECURE, OAKS BAYSIDE Country Club Neighborhood on Little Sarasota Bay. Finishes of the highest quality abound and include Custom Iron entry and interior doors, Italian Murano sconces and chandeliers, architectural recessed lighting, Marble and Porcelain Flooring, Iron and Glass custom Wine Cellar, Glass enclosed “Spirits” Showcase, luxury appointments and fixtures throughout and is a MUST SEE! The GOURMET KITCHEN is impressively equipped with top brands including SUBZERO, WOLF, 2 ASKO dishwashers, “Waterstone” gantry faucets, work-station sinks, custom range hood, MIELE Coffee Station, etc. In total, there are 2 kitchens and 3 laundry facilities. The Stunning OUTDOOR ENTERTAINING area features a spacious screened lanai with Gorgeous, Saltwater, Heated, Pebbletec 64ft Lap Pool and Spa, Marble deck, OUTDOOR KITCHEN with Twin Eagles Grill, 2 refrigerators, covered gathering area with fireplace, air-conditioned Pool Bath with Aromatherapy Steam Shower (New in 2024), storage room and Additional Open Air Patio with FIRE PIT. Extensive Home Automation (Control4: sound, lighting, etc.) and Mechanical system installations were thoughtfully executed and include a Generator, water treatment and purification systems, robust Wi-Fi throughout, Vivent video monitored security system, Air-Conditioned Garage with EV charging, resin coated floors and utility sink, etc. Impressive grounds with new landscaping, hardscaping & lighting. Newer ROOF, HVAC, Hurricane Impact Rated Windows and Doors. THE OAKS-BAYSIDE is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World - where amenities include two, 18-hole championship GOLF courses, award-winning TENNIS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL. The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

601 Fernwalk Lane, Osprey

$1,900,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Please view the 3D MATTERPORT TOUR by clicking the VIRTUAL TOUR link. Welcome to the epitome of luxury living behind the secure gates of The Oaks Bayside, where elegance meets tranquility in this meticulously crafted residence. Boasting over 4,100 square feet of exquisite living space, this fully updated home exudes sophistication and comfort at every turn. Step into a world of refined living as you are greeted by the newly pavered driveway and lush landscaping, setting the stage for the grandeur that awaits within. With a NEW ROOF and HVAC systems ensuring peace of mind, this home is truly move-in ready, offering the convenience of turnkey furnished living. Inside, the spacious floor plan unfolds to reveal a wealth of amenities, including a large office/den, family room with an eye-catching floor to ceiling fireplace. Soaring 14-foot ceilings accentuate the sense of luxury while numerous windows provide the home with natural light, creating a bright and inviting atmosphere. Entertain in style in the spacious open kitchen, featuring stainless steel appliances including a Viking refrigerator, KitchenAid double wall oven, induction cooktop, breakfast bar and center island , sure to delight even the most discerning chef. Adjacent to the kitchen, a formal dining room awaits, adorned with a gorgeous chandelier, providing the perfect setting for elegant gatherings and memorable meals. Retreat to the expansive primary suite, complete with a luxurious bath and separate soaking tub, offering a serene sanctuary for relaxation. With a split floor plan, three additional guest bedrooms provide privacy and comfort, including one en-suite bedroom for added convenience. Outside, a screened lanai beckons you to enjoy the Florida lifestyle, overlooking the large covered area, heated pool, and spa, surrounded by manicured landscaping for the ultimate in outdoor living. As a resident of The Oaks, you'll enjoy access to a distinguished country club lifestyle, including two golf courses, state-of-the-art pickle-ball and tennis courts, a WellFit Center, aquatics complex, and a vibrant social calendar. With three onsite restaurants, every dining experience is a culinary delight. The Oaks Club, one of the areas most exclusive private country club communities is located minutes from the nationally acclaimed Pine View School for the Gifted, the Legacy Trail, Casey Key, Siesta Key and all that living in Sarasota has to offer. Experience luxury living at its finest in The Oaks Bayside. Schedule your private tour today and discover the unparalleled beauty and amenities that await! Membership to The Oaks Club is required , ensuring exclusive access to the finest amenities and services. Bedroom Closet Type: Walk-in Closet (Primary Bedroom).

284 Sugar Mill Drive, Osprey

$850,000

The Oaks SubDv. ⋅ 34229 Zip Code

The Oaks Preserve - Located behind the gates of the Oaks Club, the best priced and largest development site of this stunning community. Build your dream custom home on this stunning 3.12 acres lot or build a couple homes and enjoy the privacy and convenience this lot offers. Aggressively reduced to sell. Best priced lot available in all of The Oaks. Seller performed Environmental Survey - April 2023. Surrounded by estuaries, natural preserves, and Sarasota Bay, The Oaks Preserve is a vibrant neighborhood of spacious single-family homes and award-winning villas. The Oaks Club is a private, member-owned club situated on over a thousand acres just south of downtown Sarasota. Every amenity is here — private 36 holes of championship golf , 12 Har-Tru tennis courts, croquet, pickle ball courts, fitness, wellness and three world class dining venues that would be the envy of any luxury resort. Membership to the Oaks Club is required. Aerial video available upon request. HOA and Club Fees to be confirmed. More information available upon request.

N Point Road, Osprey

$775,000

3 Beds ⋅ 3 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

**INCREDIBLE WATER AND GOLF COURSE VIEWS** from this ELEGANT, TRADITIONAL ESTATE in the Popular SAINT JAMES PARK, Cul De Sac neighborhood in The Oaks Country Club. Ideally Located near the Clubhouse and Campus of World Class Amenities, this Distinctive LIGHT AND BRIGHT floorplan offers 3-BEDS, 2 FULL plus 1 HALF BATHS, 2-Car Garage and features unique architectural details throughout including beautiful crown moldings, French doors, High Ceilings, marble and hardwood floors, etc. The updated kitchen features white solid wood cabinets, granite counters and newer stainless steel appliances while the Spacious 1st Floor Owners’ Suite features a brilliantly Updated Master Bath. Two oversized guest rooms are located on the second floor with a shared full bath. Enjoy the impressive golf course and water views from the tranquil screened lanai amidst a mature and beautifully landscape lot of over a quarter acre with a desirable Southeastern Exposure overlooking the Interior HERON Golf Course. THE OAKS is a distinguished country club community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World - where amenities include two, 18-hole championship GOLF courses, award-winning TENNIS program with 12 Har-Tru Hydro-Grid tennis courts, 4 Pickleball Courts, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL. The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and available.

226 Saint James Park, Osprey

$1,400,000

3 Beds ⋅ 3 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

This 3 bedroom, 3 bath residence in Meridian at The Oaks Preserve is an end unit on the 6th floor, membership in THE Oaks Club is required with homeownership.

3603 N Point Road Unit 603, Osprey

$1,200,000

3 Beds ⋅ 3 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

**BEAUTIFULLY RENOVATED, 1-STORY HOME ON OVERSIZED CORNER LOT WITH GOLF COURSE VIEW** Located on a quiet street behind the gates of the highly sought after Oaks-Clubside neighborhood, this 3 Bed PLUS Office (with separate entrance), 2.5 Bath home was completely UPDATED in 2020/2021 and features an open, split floorplan and high ceilings. Upgrades include: The impressive NEW KITCHEN with a large quartz topped island, solid wood cabinets and stainless steel appliances; NEW BATHS including a marble master bath with soaking tub; spacious NEW LANAI with private POOL; NEW ROOF; NEW HURRICANE IMPACT WINDOWS and NEW GARAGE DOOR; FRESHLY PAINTED interior and exterior and NEW TILE FLOORING throughout. This home is situated on an expansive CORNER LOT of nearly 2/3 acres with CIRCULAR DRIVEWAY and overlooks the 14th Hole of the interior, Heron Golf Course. THE OAKS is a distinguished country club community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World - where amenities include two, 18-hole championship GOLF courses, award-winning TENNIS program with 12 Har-Tru Hydro-Grid tennis courts, 4 PICKLEBALL Courts, CROQUET court, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL and MAGNIFICENTLY UPDATED CLUBHOUSE! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and includes IMMEDIATE GOLF ACCESS. **MUST SEE**

651 Oriskany Court, Osprey

$1,335,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

One or more photo(s) has been virtually staged. Located behind the gates of The Oaks, on a quiet cul-sac, this 4 bedroom home with 2 full and 2 half baths, is situated on a lovely lot with Southern exposure. The care that has been taken to lovingly maintain it is evident inside and out. It has a new roof, newer HVACs, has been re-piped and both the interior and exterior have been recently repainted. Enter through the front door and you will be welcomed to a great floor plan that is ideal for entertaining as well as the quiet enjoyment of those residing in this spacious home. The kitchen is huge and offers a large eat-in area, tons of cabinets, a built-in chef’s desk and large windows that flood the area with light. The master suite is oversized and has room for a sitting area, a door to the lanai and pool and big walk-in closets. There are three additional bedrooms. One of which is currently being used as an office. The split floor plan allows for room and privacy for your loved ones and guests. With a formal living room and dining room, and a den with fireplace there are so many places to gather with friends. And should you be a bibliophile, you will be delighted with the bonus of a cozy library/reading room. Outside the screened lanai is a wonderful extension of the house. With a fountain, pool and spa it celebrates the tropics in design, and yet offers a good deal of covered areas to enjoy the shade. The views from here, down the length of the #2 Heron, are phenomenal. The Oaks, Sarasota's finest golf and country club, has two distinctly unique 18-hole championship golf courses, 12 HAR-TRU tennis courts (4 lighted), new pickle ball courts, a state-of-the art fitness center, fine and casual dining options, and a wealth of recreational activities and social events. Membership is required with homeownership.

935 Blue Heron Overlook, Osprey

$1,410,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

If you are seeking a home that offers you an abundance of living space, and an incredible lot with a ton of privacy, look no more. You have found it in this John Cannon custom-built home in The Oaks Clubside. With 4 bedrooms and 4 bathrooms, an office, and a 2nd floor bonus room, you will find everything you need to live a comfortable lifestyle with your loved ones, and room to entertain guests. As you enter through the double front doors, you will get a view of the pool at the end of the formal living room. Featuring a fireplace, this is the perfect setting for a cozy night on a cool Florida evening. The entrance way is flanked by two lovely rooms. The formal dining room on one side, and an office is on the other. Both rooms have large windows, making them bright and cheery. The center island kitchen features stainless steel appliances including a new LG refrigerator, a Whirlpool oven and stove top, granite countertops, and lots of cabinets for storage. With a breakfast bar and dining nook, the options for meals, from formal to casual, are limitless. The master suite is huge, and has doors to the pool area, and a bathroom with dual sinks, a soaking tub and walk-in-shower. The additional bedrooms on the main floor are good sized. Upstairs you will find a large bonus room with a balcony. The versatility of this area makes it the perfect space for anything you can imagine. Outside you will find the lanai with pool and spa, which offers incredible privacy. It is 82 feet from the back to the edge of the property. Surrounded by local flora, it offers a tranquil setting. The covered areas allow for room to dine al fresco in the shade, and there is a wet bar with a small refrigerator. Add to this a large laundry room with a new washer, a 3-car attached garage, A NEW ROOF in 2022, and too many other features to mention, and you know you must see this house and make it your own! The Oaks Club, Sarasota’s premiere golf and country club, has two champion 18-hole golf courses, twelve HAR-TRU tennis courts (4 lighted), four new pickleball courts, an over 7,500 square foot state-of-the-art WellFit Center, an award-winning culinary team, and robust activities and social calendars. Club membership is required with homeownership.

853 Macewen Drive, Osprey

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