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$365,000
2 Beds 2 Baths Bay Street Village & Towncenter Land Condo SubDv. 34229 Zip Code
This well-maintained first-floor condominium offers an ideal opportunity for full-time living or a seasonal Florida retreat. Featuring the desirable Osprey floor plan, this open-concept residence includes two bedrooms, two bathrooms both with granite vanity tops, and a bonus room/office. The unit is conveniently located on the first floor with no stairs and provides easy access to the community’s heated resort-style pool, fitness center, and clubhouse. The kitchen is appointed with 42-inch cabinetry and granite countertops. The primary bathroom features a tiled walk-in shower and dual vanity. Additional highlights include a screened lanai, Huge 2.5-car garage, and two-car driveway, offering ample parking and storage. The condominium has been meticulously maintained and is move-in ready. Located in the gated, maintenance-free community of Bay Street Village, the property is ideally situated between Sarasota and Venice, with convenient access to dining, shopping, the Legacy Trail, Pine View School, and nearby beaches including Siesta Key, Nokomis, Casey Key, and Venice Beach. Additional features include concrete block construction, impact-resistant windows and doors, tile roof, and paver driveway. Water and sewer are included in the HOA fee, and there is no CDD fee. Furniture is available under a separate contract between buyer and seller.

4235 Expedition Way Unit 102, Osprey

$1,001,000
3 Beds 3 Baths Bayside SubDv. 34229 Zip Code
Discover coastal-inspired living at its finest in this exquisite lakefront home nestled within **Bayside**, an exclusive Taylor Morrison-built community of just 49 meticulously landscaped, maintenance-free residences. As you step inside, your eyes are immediately drawn through the expansive great room to breathtaking water views that capture the essence of waterfront living. The great room offers generous space for both elegant entertaining and relaxed everyday enjoyment, enhanced by tray ceilings and elegant crown molding—among the many thoughtful upgrades found throughout the home. The gourmet kitchen is a standout, featuring quartz countertops, a large closet pantry, premium GE Monogram appliances, an LG refrigerator, and a spacious island with counter seating and dual sided cabinets. This space overlooks the lanai and pool, creating a seamless indoor-outdoor flow. Outside, the lanai is truly exceptional—an entertainer’s dream with a fully equipped outdoor kitchen, a cozy gas fireplace, both covered and open seating areas, and a sparkling saltwater pool and spa with gas heater. All of this is beautifully framed by a brand-new 2025 panoramic screen enclosure, offering sweeping views of the lake and abundant wildlife. The primary suite is a private retreat with stunning lake views with a luxurious bath featuring a spacious walk-in shower and a full wall vanity with dual sinks. The expansive walk-in closet includes custom built-ins for maximum storage and organization. A thoughtful split-bedroom plan ensures privacy, with Bedroom 2 offering an ensuite bath, Bedroom 3 conveniently located near the main bath, and a spacious den/office providing flexible living options. Additional practical features include a well-appointed laundry room with ample cabinetry and a garage equipped with its own split HVAC system. Bayside residents enjoy exclusive access to a private waterfront park overlooking the Intracoastal Waterway, with panoramic views of Casey Key and spectacular sunsets. This open space includes a day dock, kayak and paddleboard launch, fire pit, and generous lawn area—perfect for relaxing or gathering with friends. Located west of the trail with direct water access, this rare combination of lifestyle and location is nearly impossible to find. Homes like this don’t last long. Don’t let this one get away!

3936 Waypoint Avenue, Osprey

$1,385,000
3 Beds 3 Baths Oaks SubDv. 34229 Zip Code
Meticulously maintained and updated with care, this 3 bedroom, 3 bath + den/study home in The Oaks Clubside offers beautiful views. A mixture between clean modern lines and cottage chic this house feels cozy. Yet it has an open floor plan, soaring ceilings and every room in the house is light and bright. The formal living room opens to the large lanai and pool with Southern exposure. The view over the lake to the Eagle #6 is simply gorgeous! It is one of the most stunning views in the neighborhood. There is plenty of room to host friends and loved ones. Serve a meal in the formal dining room, have a causal lunch in the kitchen nook or at the breakfast bar, or dine al fresco under the large, covered area overlooking the pool. From the luxurious master suite to the guest bedrooms, this home is beautifully appointed and showcases the finest of details and improvements, including a new roof, impact windows and doors and pretty, updated landscaping. The Oaks, Sarasota’s premier golf and country club, offers two championship golf courses, HAR-TRU tennis courts, pickleball, croquet, and a state-of-the-art WellFit Center.

434 Macewen Drive, Osprey

$925,000
4 Beds 3 Baths Rivendell SubDv. 34229 Zip Code
BEAUTIFUL INSIDE and exceptionally well maintained, this Rivendell home offers the kind of upgrades, efficiency, and outdoor living that are becoming increasingly hard to find. This Luxurious home is situated on a large beautifully landscaped, lake front lot with a Southeast Exposure overlooking Oscar Scherer State park! The interior layout is spacious and functional, featuring tile flooring throughout the main living areas and carpet in the bedrooms for comfort. A dedicated front office connects directly to the primary suite, creating a flexible space ideal for working from home, a sitting room, or even a private retreat. High ceilings and an open flow between the living spaces enhance the overall feel, while the home’s condition reflects true pride of ownership. Step outside and the property truly separates itself. The heated pool has been resurfaced with Pebble Tec and features a solar heating system that was just replaced in 2024, providing year-round enjoyment with energy efficiency. The outdoor space is further enhanced with hurricane roll-down protection, an outdoor stereo system, and a removable baby safety fence—offering both entertainment and peace of mind. Major updates have already been handled, including a BRAND NEW ROOF in 2025 with a transferable 20-year warranty and TWO NEW A/C systems installed in 2025. The home also benefits from an irrigation well, helping maintain the lush landscaping while keeping water costs zero. Total electric costs have remained under $2,400 annually for the entire property, showcasing impressive efficiency for a home of this size. Additional features include a mini-split A/C system in the garage paired with an insulated garage door—perfect for a workshop, gym, or climate-controlled space—as well as a large safe that conveys with the sale. Rivendell residents enjoy a well-rounded lifestyle with low HOA fees that include a heated community pool, playground, and scenic recreational trails—all with no CDD fees. The community offers a rare private path directly to Pine View School  and borders Oscar Scherer State Park along with over 200 acres of preserved land, creating a unique blend of convenience and natural surroundings.  The home is near both Siesta and Nokomis Beaches, Costco, and loads of shopping and restaurants. Home is situated less than a mile from the Legacy Bike Trail. Minutes to the distinguished Pine View School, the #1 rated public gifted college-prep school in Florida. This is a rare opportunity to own a move-in-ready home where the major expenses have already been taken care of—offering a combination of condition, upgrades, and outdoor lifestyle that is hard to match. Book your private showing now to see this property for yourself!

1016 Scherer Way, Osprey

$2,100,000
4 Beds 4 Baths Oaks SubDv. 34229 Zip Code
Under contract-accepting backup offers. **IMPRESSIVE GOLF COURSE ESTATE IN THE HIGHLY SOUGHT-AFTER OAKS COUNTRY CLUB** Situated on an oversized 0.59-acre lot, this exceptional, meticulously-maintained residence features many upgrades and offers breathtaking garden and golf course views in a private, serene setting. Impressive curb appeal and beautifully manicured landscaping welcome you into a beautifully appointed home featuring 4 BEDROOMS plus a STUDY/DEN, 3 FULL and 1 HALF BATHS. Inside, you’ll find high ceilings, elegant crown molding, a cozy fireplace, plantation shutters, custom built-ins, and rich hardwood flooring throughout. The spacious kitchen is designed for both functionality and style, showcasing granite countertops and black stainless KitchenAid appliances. The expansive primary suite is a true retreat, complete with multiple walk-in closets, dual vanities, a soaking tub, and a custom-tiled shower. Enjoy Florida living at its finest on the screened lanai, featuring a heated pool and spa, travertine marble pool deck, and a large covered entertaining area—all overlooking tranquil golf course and garden views for ultimate privacy. Additional highlights include a 3-car garage and thoughtfully designed indoor-outdoor living spaces perfect for entertaining or relaxing. 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**

448 E Macewen Drive, Osprey

$710,000
5 Beds 3 Baths Talon Preserve On Palmer Ranch SubDv. 34275 Zip Code
Virtually Staged. Welcome to your slice of the Florida coastal lifestyle at 6304 Winding Pin Drive in beautiful Nokomis. This is a rare opportunity to own a spacious 5-bedroom, 3-bathroom home at an exceptional price point—perfectly blending comfort, style, and resort-inspired living. Most importantly, enjoy low HOA's, NO CDD fees, and a place you can truly entertain. Step inside and discover a thoughtfully designed layout ideal for both everyday living and entertaining. The home sits on a premium preserve lot, offering peaceful sounds of nature, while allowing natural light to pour into the home. Out back, your private oasis awaits—a sparkling saltwater pool and spa overlooking a serene pond view, creating the perfect backdrop for morning coffee or sunset relaxation. Enjoy the benefits of a home that comes with a flat tile roof that is built to withstand any hurricane thrown its way. All appliances and HVAC are 2022. Located in the highly sought-after Talon Preserve community, you’ll experience true resort-style living every day. Residents enjoy access to a vibrant clubhouse with a full-service bar and restaurant, along with a wide array of amenities, including pickleball and tennis courts, bocce ball, a state-of-the-art fitness center, and even an arcade room for added fun. The community is designed for an active, social lifestyle, with walkable streets surrounded by lush natural beauty. Whether you're hosting poolside gatherings, enjoying the nearby Gulf beaches, or taking advantage of the incredible neighborhood amenities, this home offers the perfect blend of coastal charm and modern convenience. Live where others vacation—schedule your private showing today.

6304 Winding Pine Drive, Nokomis

$1,600,000
3 Beds 3 Baths Oaks SubDv. 34229 Zip Code
Experience the charm of this original Bo MacEwen–designed home in The Oaks Clubside. Ideally located on a quiet cul-de-sac, in the Saint James Park enclave, this 3 bedroom residence with 2.5 baths, overlooks the opening hole of the Heron Course. Clean, bright and beautifully updated and maintained, this home has an open floor plan and features high, coffered ceilings, crown molding, French doors and gleaming mahogany floors. Extensively improved, the home has been repainted inside and out, with refurbished flooring throughout (including the garage), new carpeting, a newly renovated laundry room, new pool equipment with a saltwater system, a new driveway, updated fencing, and refreshed landscaping. The open kitchen has been updated and offers quartz countertops, Sub-Zero refrigeration, a wine fridge, beverage drawers, custom cabinetry, walk-in pantry and an island that serves as a breakfast bar. The great room opens to the lanai with pool, spa, and golf views. The split plan provides privacy with a remodeled master suite featuring a spa-like bath and custom walk-in closet. The south side includes an en suite guest room and a third bedroom/office with lanai access and golf views. Additional features include a 2-car garage with epoxy floor and storage, plantation shutters, a newer roof (2020), hurricane shades and new Pella bay windows. Saint James Park offers easy access to all of The Oaks Club’s offerings: tennis. Pickleball courts, croquet lawn, a state-of-the are WellFit Center, and golf facilities. Members enjoy a wide variety of dining options and a robust social calendar.

228 Saint James Park, Osprey

$508,000
3 Beds 2 Baths Talon Preserve On Palmer Ranch SubDv. 34275 Zip Code
Brand new listing in the highly sought-after community of Talon Preserve on Palmer Ranch — priced to sell fast! Skip the wait and move right into this upgraded, move-in-ready Hallmark plan. This 3-bedroom, 2-bath home includes over $70,000 in upgrades and backs to a protected preserve with no rear neighbors and unobstructed views. Set on a quiet non-thru street within close proximity to the amenity center, this home offers both privacy and convenience. Inside, 22-inch diagonal tile flooring runs throughout with upgraded Sherwin Williams paint and an open great room layout designed for everyday living and entertaining. The kitchen features 42-inch solid wood cabinets, quartz countertops, marble backsplash, upgraded appliances, and a natural gas cooktop. The primary suite includes a tray ceiling, walk-in closet, dual sinks, upgraded vanity, and frameless glass walk-in shower. Additional upgrades include a custom laundry and butler’s pantry area with washer and dryer, updated lighting and hardware throughout, extended garage with 4-foot expansion and epoxy flooring, upgraded interior doors, smart home features, and a tankless water heater. The covered lanai with electric screens opens to a paver patio with seating wall and built-in grill station with quartz counters—ideal for outdoor dining, relaxing evenings, and enjoying the preserve views year-round. Not located in a flood zone. Low HOA. No CDD. Zoned for A-rated schools. Talon Preserve offers a true resort-style lifestyle with a heated pool, spa, full-service restaurant and bar, clubhouse, fitness center, arcade, pickleball, tennis, bocce, dog park, and direct access to the Legacy Trail. Minutes to beaches, Oscar Scherer State Park, golf, Sarasota Memorial Hospital, and the dining and culture of downtown Sarasota and Venice. Move-in ready. No construction delays. Start living the Florida lifestyle immediately.

6295 Crested Eagle Lane, Nokomis

$1,495,000
4 Beds 4 Baths Oaks SubDv. 34229 Zip Code
Located on a quiet cul-de-sac within the gates of The Oaks Clubside, this custom-built residence at 554 Dove Pointe offers privacy, space, and the refined lifestyle of one of Sarasota County’s most established country club communities. Set on a beautifully landscaped homesite covering more than a half-acre, the property enjoys exceptional curb appeal with a circular drive, mature trees, and a fully fenced backyard—an ideal setting for pets, outdoor play, or peaceful evenings surrounded by nature. Spanning 3,500+ square feet of interior living space, the thoughtfully designed floor plan includes four bedrooms, three-and-a-half baths, and a dedicated study/den, creating flexible space for everyday living, guests, or working from home. The home has been carefully maintained and enhanced with a new roof completed in 2025, providing peace of mind for years to come. A welcoming foyer leads into the main living areas where high ceilings, crown molding, and expansive sightlines create an inviting atmosphere. The living/dining room is anchored by a gas fireplace and wet bar, while walls of sliding glass doors and French doors open to the outdoor living spaces, blending interior comfort with Florida’s year-round indoor-outdoor lifestyle. The chef’s kitchen serves as the center of the home, offering solid wood cabinetry, granite countertops and backsplash, stainless steel appliances, a walk-in pantry, and an expansive island with breakfast bar seating. The space flows seamlessly into the family room and breakfast nook, creating a comfortable gathering area for casual meals and conversation. The primary suite is privately situated and features terrace access, a spacious walk-in closet, and an en-suite bath designed for relaxation with dual vanities, soaking tub, and a walk-in shower. Three additional guest bedrooms are arranged in a split configuration, two featuring en-suite baths and walk-in closets, ensuring privacy and comfort for visitors. Outdoor living is designed for both relaxation and entertaining. The screened lanai and pavered pool deck surround a private swimming pool with raised spa and summer kitchen, creating an inviting setting for gatherings or quiet afternoons at home. Beyond the pool area, the fenced backyard offers an expansive lawn ideal for pets or outdoor enjoyment. Residents of The Oaks Country Club enjoy a gated setting spanning more than 1,000 acres along Little Sarasota Bay. The required membership provides access to an exceptional collection of amenities including two championship 18-hole golf courses, 12 Har-Tru tennis courts, croquet lawns, a fitness center, heated community pool, and multiple dining venues. Ideally located in Osprey between Sarasota and Venice, this home places residents just minutes from the Gulf beaches of Casey Key and Siesta Key, waterfront dining, and everyday conveniences. Nearby cultural destinations such as Selby Gardens, Sarasota Opera House, and The Bay Park anchor Sarasota’s renowned Cultural Coast, while marinas, nature preserves, and scenic trails offer endless opportunities to enjoy the area’s outdoor lifestyle. This property presents a rare opportunity to enjoy private, pet-friendly living on a spacious cul-de-sac homesite within one of Sarasota’s premier golf and country club communities.

554 Dove Pointe, Osprey

$375,000
3 Beds 3 Baths Towns-End Shores SubDv. 34229 Zip Code
Virtually Staged. Perfectly positioned west of the Trail in the desirable coastal community of Towns-End Shores, this versatile property offers an exceptional opportunity to enjoy the Florida lifestyle while generating income. This home provides both peace of mind and outstanding value in one of Sarasota County’s most sought-after areas. Designed with flexibility in mind, the property features a unique two-level layout that allows you to live upstairs while renting the lower-level in-law suite, currently producing $1,500 per month on a month-to-month lease. The private suite includes its own entrance, bedroom, bathroom, kitchen, and living area, creating an ideal setup for rental income, guests, or multigenerational living. Upstairs, the two bedroom and two bathroom primary residence offers an open and inviting layout filled with natural light. The kitchen features granite countertops, solid wood cabinetry, and a functional layout that flows easily into the living and dining areas. Crown molding, tray ceilings, wood flooring, and thoughtful design elements add character and comfort throughout the home. Recent updates provide valuable peace of mind, including a new air conditioning system and water heater installed in 2024, while the air-conditioned garage adds versatility for storage, hobbies, or a workshop. Plus, NEW ROOF 2026 with 10 year warranty! NO FLOOD ZONE — meaning flood insurance is not required. Outdoor living is just as appealing. Residents enjoy low HOA dues and access to the sunny community pool, along with the rare convenience of a private kayak launch, allowing you to explore nearby waterways and mangroves with ease. The location truly sets this property apart. Bike to the beach, explore nearby Oscar Scherer State Park, or access the Legacy Trail just minutes away for miles of scenic biking and walking. You are also conveniently located near South Bay and the beautiful beaches of Casey Key, along with local dining, shopping, and coastal attractions. Whether you are seeking a primary residence with income potential, a coastal retreat, or an investment property in a prime west-of-the-trail location, this home delivers flexibility, lifestyle, and value all in one. Schedule your private showing today and experience the possibilities this unique property offers.

1795 Highland Road, Osprey

$318,000
3 Beds 2 Baths Bay Street Village & Towncenter Land Condo SubDv. 34229 Zip Code
Under contract-accepting backup offers. Virtually Staged. Spectacular water views from most windows in this immaculate, lightly used 3BR/2BA condo, built in 2018 and located in the gated community of Bay Street Villages. The popular Ibis floor plan offers an open-concept kitchen, dining, and great room with designer finishes, including white 42” cabinetry, light granite countertops, custom backsplash and stainless-steel appliances. Enjoy peaceful pond views with birds and wildlife from the screened lanai. Quality construction and peace of mind are provided by hurricane-impact windows and doors, concrete block construction, tile roof, and a paver driveway. The primary suite features plantation shutters, a custom ceiling fan with light, custom closet system, linen closet, lighted 10× makeup mirror, and a bidet-ready outlet. The second and third bedrooms also include custom ceiling fans and 2" blinds. The dining area is accented by a custom light fixture and accordion blinds on the balcony sliding doors. The balcony is enhanced with a tropical palm-leaf ceiling fan and outdoor curtains for added shade and comfort. The great room is fitted with plantation shutters for added elegance. A spacious laundry room includes a washer and dryer. Added features-Ring Doorbell, Keyless Entry on Front Door as well as an Exterior Garage door keypad. The monthly condo fee includes water, sewer, exterior and grounds maintenance, gated entry, heated resort-style pool, cabana, fitness center, and club room. No CDD fees. Ideally located near Nokomis Beach, Casey Key, Siesta Key Beach, the Legacy Trail, Sarasota and Venice dining and shopping, Oscar Scherer Park, and A-rated Pine View School. Maintenance-free Florida living at its best.

4304 Expedition Way Way Unit 105, Osprey

$2,995,000
3 Beds 4 Baths Bayside SubDv. 34229 Zip Code
Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the Bay and Intracoastal Waterway greet you upon entry, while the dramatic great room features a striking cupola with soaring 22-foot ceilings, wraparound windows, architectural beams, and detailed millwork that beautifully frame the waterfront setting. Pocketing impact sliders seamlessly open the living space to an expansive covered lanai where breathtaking sunsets, dolphins, and gentle coastal breezes create an unforgettable everyday backdrop. The open chef’s kitchen is designed for both entertaining and daily living, offering high end stainless appliances, a gas cooktop with pot filler, wine cooler, abundant cabinetry, and an oversized quartz island. Outdoor living shines with wood-paneled ceilings, crema pro leathered marble flooring, a gas fire pit, and a fully equipped outdoor kitchen with grill and beverage refrigerator. The solar and heat pump-heated saltwater lap pool and spa, outdoor shower, and private dock with lift complete the ultimate waterfront retreat. The primary suite enjoys beautiful water views and features a sitting area, double tray ceiling, dual custom walk-in closets, and a luxurious bath with double vanities and walk-in shower. Two additional en-suite bedrooms, a den or office, and a powder room provide comfort and flexibility. Wood-look tile flooring runs throughout, complemented by impact windows and doors, a smart-enabled security system, whole-home generator, and water conditioning system. Located just minutes from Casey Key, Nokomis Beach, Oscar Scherer State Park, and the Legacy Trail, this home offers effortless access to beaches, boating, dining, and recreation. An extraordinary waterfront residence where luxury, comfort, and coastal beauty come together, offering the lifestyle you’ve always imagined.

14401 Masthead 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.

480 Oriskany Court, Osprey

$2,260,000
Casey Key SubDv. 34275 Zip Code
Set along one of the most coveted stretches of Casey Key, 4001 Casey Key Road presents a rare opportunity to secure nearly half an acre of direct Gulf-front property in Nokomis. Boasting approximately 99 feet of frontage on the Gulf of Mexico and spanning roughly 0.47 acres (20,381 square feet), this expansive homesite offers unobstructed water views, direct beach access, and everyday sunsets over the Gulf. Casey Key is treasured for its quiet, residential character, free from high-rise development, while still offering convenient access to the mainland. Just minutes away are the shops and dining of Venice Island, waterfront restaurants in Nokomis, and easy connectivity via U.S. 41 and I-75. Sarasota’s cultural amenities, golf courses, marinas, and private aviation options are all within a short drive, making this an exceptional blend of seclusion and accessibility. Create your dream Gulf-front estate, with full Gulf views, direct water access, and a premier address on one of Southwest Florida’s most prestigious barrier islands, 4001 Casey Key Road is ready for its next chapter.

4001 Casey Key Road, Nokomis

$570,000
3 Beds 3 Baths Webbs W D Add To Village Of Osprey SubDv. 34229 Zip Code
Location, location, location. Nestled west of the Trail in the heart of Osprey, this beautifully updated three-bedroom, two-bath home with a den offers a rare opportunity just moments from Sarasota Bay. Set on a spacious, private lot framed by mature oak trees and lush tropical landscaping, the property features no HOA or CDD restrictions. Inside, the home offers an open-concept layout with durable, stylish flooring throughout. The updated kitchen includes granite countertops, solid wood cabinetry, and stainless steel appliances, opening comfortably to the main living areas. Both bathrooms have been tastefully refreshed with quality finishes, creating a truly move-in-ready space. Enjoy the Florida lifestyle with close proximity to the Main Street fishing pier and Spanish Point Marina. Nearby attractions include Oscar Scherer State Park, Bay Preserve at Osprey, and Historic Spanish Point, with convenient access to Casey Key, Nokomis Beach, and world-famous Siesta Key beach. Pine View School for the Gifted is also located nearby. The expansive backyard offers ample space for outdoor living, entertaining, or future customization. Whether you’re seeking a primary residence, vacation home, or investment opportunity, this property delivers location, flexibility, and coastal charm. Come experience relaxed coastal living just moments from the bay, with nearby water access for kayaking or canoeing — a peaceful Osprey retreat that’s ready to welcome you home.

51 Webb Street, Osprey

$690,000
3 Beds 3 Baths Blackburn Harbor SubDv. 34229 Zip Code
BETTER HURRY, LOOK AT THE PRICE! Waterfront living and a true boater’s lifestyle await in this meticulously maintained end-unit residence located in the gated, amenity-rich community of Blackburn Harbor in Osprey. This beautifully upgraded condo offers sweeping Intracoastal water views with Gulf glimpses, abundant natural light, and exceptional privacy within an exclusive boutique building of only 15 residences. BEING SOLD WITH FURNITURE except for a couple of personal items. The spacious floor plan features over 2,600 square feet of well-designed living space with 3 bedrooms, 3 baths, and flexible areas ideal for a den, office, or entertaining. A welcoming foyer, breakfast area, and expansive living room all showcase stunning, eye-level water views, while the large lanai is perfectly positioned for sunsets, birdlife, dolphins, and passing boats along the Intracoastal Waterway. The chef’s kitchen is both functional and elegant, featuring exquisite granite countertops, custom cabinetry with soft-close pullouts, and ample workspace for everyday living and entertaining. Interior upgrades include tile flooring, plantation shutters, remote-controlled blinds, higher ceilings, a built-in bar, and generous closet space throughout. The primary suite serves as a private waterfront retreat with beautiful Intracoastal views, custom closets, and a spa-style bath with a walk-in shower, soaking tub, dual vanities, makeup area, and private water closet. Guest baths are thoughtfully designed for comfort and convenience. Boating enthusiasts will appreciate water access and protected dockage, with boat slips available on a first-come, first-serve basis and currently no waiting list, accommodating vessels up to approximately 39 feet. With no bridge access and only minutes to open water and the Gulf, this location is ideal for cruisers and avid boaters seeking quick, easy Intracoastal and Gulf access. Additional features include two assigned parking spaces, one in the under-building garage and one covered carport, private unit storage, EV charging capability, an interior laundry room with sink and cabinetry, newer washer and dryer, newer hot water heater, impact-rated sliders, and a new 2025 roof with no upcoming assessments. Residents enjoy resort-style amenities including a heated pool, tennis and pickleball courts, clubhouse with fitness area, kayak storage and launch, fishing, waterfront gazebo with grills, walking paths, and lush greenspace. Located directly across from Oscar Scherer State Park and near the Legacy Trail, the community offers easy access to biking, hiking, kayaking, and outdoor recreation. Perfectly positioned between Sarasota and Venice, this prime Osprey location is approximately 15 minutes to Downtown Sarasota, about 10 minutes to Historic Venice Island, and just minutes to Nokomis Beach, Venice Beach, Casey Key, and Siesta Key. Close to hospitals, medical facilities, marinas, golf, dining, and shopping, this residence offers the ideal blend of waterfront luxury, boating convenience, and low-maintenance coastal living.

6100 Jessie Harbor Drive Unit 203, Osprey

$631,000
3 Beds 3 Baths Rivendell SubDv. 34229 Zip Code
Located within The Woodlands at Rivendell, this meticulously maintained single-family residence offers a sophisticated balance of comfort, functionality, and tranquil natural surroundings. Backing to a serene lake and protected preserve, the home enjoys exceptional privacy and peaceful water views. Designed with an open, split-bedroom floor plan, the residence features three bedrooms, two full baths, a dedicated office, and an additional pool bath—well suited for both everyday living and gracious entertaining. The owner’s suite serves as a private retreat, highlighted by a tray ceiling, two walk-in closets, and a spa-inspired bath with dual vanities, a soaking tub, Roman shower, and private water closet. Two well-appointed guest bedrooms are thoughtfully positioned to provide comfort and privacy for family and guests alike. At the heart of the home, the expansive kitchen is appointed with 42-inch cabinetry, a generous breakfast bar, and a separate breakfast area, seamlessly connecting to the main living space and the formal dining room. The layout encourages both relaxed gatherings and more formal occasions. Outdoor living is equally impressive, featuring a 36-foot pool and an expansive 60-foot screened lanai—an ideal setting for entertaining or simply enjoying the picturesque lake and preserve backdrop. Additional highlights include a three-car side-entry garage, a 2024 tile roof, a 2023 HVAC system, and whole home hurricane protection, offering both convenience and long-term peace of mind. Ideally situated near Casey Key Beach, the Legacy Trail, and the highly regarded Pine View School, this residence presents an exceptional opportunity to enjoy refined Florida living within one of the area’s most desirable communities.

659 Rivendell Boulevard, 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

$1,050,000
3 Beds 3 Baths Talon Preserve On Palmer Ranch SubDv. 34275 Zip Code
Welcome to the epitome of resort-style living in the exclusive gated community of Talon Preserve on Palmer Ranch. This exquisite home, built in 2021, offers a perfect blend of luxury, comfort, and modern convenience, ensuring every day feels like a vacation. From the moment you arrive, the lush landscaping, Mediterranean tile roof, and elegant entryway set the stage for the beauty that lies within. Spanning over 2,483 square feet, this meticulously maintained, like-new home boasts 3 bedrooms, an office, and 3 bathrooms. The open-concept layout features luxury vinyl plank flooring, creating a seamless flow from room to room. French doors at the front of the home reveal a versatile flex space currently used as a home office, along with an oversized guest bedroom complete with its own ensuite—ideal for a private guest retreat. The heart of the home is the chef-inspired kitchen, adorned with quartz countertops and barstool seating space. Equipped with stainless steel appliances, a vent hood, built-in double oven, gas cooktop, and a walk-in pantry, the kitchen is a culinary enthusiast's dream. Coffered ceilings add a touch of elegance to the adjacent living room, enhancing the home's wonderful charm. The owner's suite is a serene haven, featuring tray ceiling detailing, a luxurious ensuite bathroom with a dual-sink quartz vanity, a spacious walk-in shower, and a massive walk-in closet. Practical upgrades include a spacious laundry room with cabinetry and a utility sink, offering convenience and functionality. Step outside through double pocketing sliding glass doors to your personal oasis—overlooking the pool and a peaceful water view. The newly re-screened pool cage, heated saltwater pool, and surrounding pavers create an ideal setting for entertaining or unwinding. Roll-down electric sun shades on the lanai, along with sun screens on the two rear windows and front door adds comfort and versatility. This home is designed with safety and efficiency in mind, featuring impact windows and a whole-house generator for peace of mind during a storm. Energy-efficient upgrades include a mini-split air conditioning system 3-car garage with epoxy-coated flooring—perfect for a home gym, workshop, or climate-controlled storage. Both garage doors are fully insulated, and after-market blown-in insulation enhances comfort and reduces utility costs. The garage also includes an electric car charging station for your car. The lanai is prepped for your custom outdoor kitchen, with gas, water, and electric lines already in place. With no flood zone concerns, no CDD fees, and a reasonable HOA, this home represents an unbeatable value in one of Sarasota's most sought-after communities. Living in Talon Preserve offers more than just a beautiful home; it's an active lifestyle. Enjoy the amenity center with a beach-entry heated pool featuring a rock waterfall, lap lanes, splash pad, spa, an 18,000-square-foot clubhouse with an on-site bar and restaurant, state-of-the-art gym, arcade, dog park, tennis courts, bocce ball, and eight pickleball courts. Nature lovers will relish proximity to Legacy Trail and Oscar Scherer State Park, while beachgoers are less than 10 miles from Siesta Key and Nokomis Beach. Conveniently located near golf courses, shopping, and the vibrant arts and dining scenes of Sarasota and Venice, this is Florida living at its finest.

14545 Eagle Branch Drive, Nokomis

$164,000
1 Beds 2 Baths Pine Run SubDv. 34229 Zip Code
One or more photo(s) has been virtually staged. Welcome to Pine Run in Osprey! Half-way between Sarasota and Venice, convenient to both with ample shopping and dining close by. Your 1 bedroom one and a half bath oasis is nestled on 20+ acres of lush native Florida landscape. This popular ground floor unit features large glass sliders and your own private courtyard in the front of the unit where you can enjoy your morning coffee and a screen enclosed covered rear porch where you can enjoy your evening with a beautiful sunset glow. New interior paint and baseboards surround neutral tile floors in the main living areas. The popcorn ceiling was removed for you. Inside laundry closet and a deeded carport are also part of the package. Bring your animals to this pet friendly home! Located less than 1/2 mile from the Gulf, this 147-unit community supports your activities with a busy social calendar and many shared amenities to choose from each day. It features two pools, 3 tennis courts, 3 pickle ball courts as well as a Club House with fitness and library. There is a kayak storage area for paddle adventures, and the Blackburn Point Park is 1/4 mile away where you can launch and enjoy the Intracoastal waterway. Nokomis Beach and Oscar Scherer State Park are both a short drive away, or you can take a bicycle on the Legacy Bike Trail to downtown Sarasota or downtown Venice. The Florida lifestyle awaits!

200 Woodland Drive, Osprey

$335,000
2 Beds 2 Baths Lake Vista SubDv. 34229 Zip Code
In the lush and serene grounds of this private and peaceful community is a best-kept secret with a name that says it all. Within Hidden Bay, this condominium gem resides in a spot on the community lake with a stunning view and soothing sound of waterfalls from your own enclosed lanai. Fully furnished with mostly all new furniture in the owners’ suite, including a new king-size mattress, living room, guest bedroom and the office/den, this turnkey treasure is move-in ready! Loaded with many new upgrades which include new kitchen appliances such as refrigerator, microwave and dishwasher (2025), new laminate flooring in both bedrooms (2025), a new water heater (2024), new faucets and toilets (2025), new air conditioner (2020), all new screens (2025), all new slider wheels (2025) and interior painted (2025). The home offers two bedrooms, two baths and an office/den, a one- car detached garage and an etched glass front door. The flooring consists of new laminate in both bedrooms, laminate in the office/den and ceramic tile throughout the rest of the home. Beautiful lake views can be seen from the living room, kitchen and owner’s suite. The owner’s suite bath has dual vanities, a soaking tub and a walk-in shower while the guest bath has a soaking tub. This unique waterfront community exudes an awesome Florida lifestyle that boasts many amenities with a newly renovated heated pool and spa, a clubhouse with a full kitchen, a tiki bar, game rooms, a library, a fitness center, a large sundeck, grilling stations, two lit pickleball courts, tennis, a kayak launch, a dog park, a car wash area and a 500-yard elevated boardwalk that winds through mangroves and palms offering scenic sunset watching. And coming soon is a 150-foot fishing pier all for your enjoyment. HOA fees include exterior maintenance, water, sewer, trash and basic cable. Centrally located between Sarasota and Venice, Hidden Bay is on Little Sarasota Bay in Osprey, an ideal location just minutes from the award-winning beaches of Siesta Key and Venice Beach, Sarasota with its many cultural venues, golfing and a variety of casual and fine dining restaurants. Make this special home your own piece of paradise!

291 Hidden Bay Drive Unit 102, Osprey

$565,000
3 Beds 2 Baths Rivendell The Woodlands SubDv. 34229 Zip Code
Set on a quiet cul-de-sac in The Woodlands at Rivendell, this furnished and thoughtfully maintained residence offers a peaceful setting surrounded by mature landscaping and wooded views. The extended foyer welcomes you into an open great-room layout spanning nearly 2,200 square feet, where high tray ceilings, plantation shutters, and hardwood flooring create a cohesive flow throughout the main living areas. The great room features floating shelves, an electric fireplace, and walls of glass sliders that open to a serene, screen-enclosed pavered patio overlooking private natural surroundings—ideal for morning coffee or evening relaxation. The gourmet kitchen was completely updated in 2022 and includes quartz countertops, a center island with seating, tile backsplash, walk-in pantry, and stainless-steel appliances, seamlessly connecting to the dining and living spaces. The primary suite is privately positioned and offers a sitting area, direct patio access, dual closets, and a renovated en-suite bath. Two additional guest bedrooms share a full bathroom, while a dedicated office or study provides flexibility for remote work or hobbies. A well-appointed laundry room with built-in cabinetry completes the interior layout. Recent enhancements include a newer air-conditioning system and storm protection throughout, featuring shutters on all openings, a roll-down shutter at the front entry, and a hurricane screen for the patio. Rivendell is a deed-restricted community spanning approximately 400 acres of preserves, ponds, and walking paths. Residents enjoy a community pool, playground, parks, gazebo, and sidewalks that connect the neighborhood. Just beyond the gates, Oscar Scherer State Park and the Legacy Trail offer miles of outdoor recreation, while nearby golf courses, shopping, dining, and Sarasota’s white-sand beaches provide endless lifestyle options. This well-located home combines natural surroundings, modern updates, and access to some of Sarasota County’s most desirable amenities—an inviting opportunity in a celebrated community.

767 Fordingbridge Way, Osprey

$10,600,000
4 Beds 5 Baths Casey Key SubDv. 34275 Zip Code
Set along one of Casey Key’s most coveted stretches, 3210 Casey Key Road presents a rare Gulf-to-Bay estate where water defines nearly every moment of daily life. Enjoy your private beach with rare, grandfathered cabana and your private bay frontage with dock and irreplaceable covered boat lift. Spanning almost 5,400 square feet under air across three-plus levels, this 2018-built residence offers four bedrooms, four full baths, a powder bath, multiple living and bonus spaces and, last but not least, an indoor half basketball court, all framed by impact-rated glass and serviced by a three-stop elevator. Arrival begins through a lushly landscaped circular motor court leading to a coastal-inspired façade and a covered entry accented by wood inlay ceilings. Inside, engineered wood floors, crown molding, and curated architectural details introduce interiors that balance sophistication with warmth. The dining room captures Gulf views through an oversized window, while the library doubles as a refined retreat with beamed ceilings, built-ins, a fireplace, and French doors opening to a Gulf-facing terrace. At the heart of the home, the great room unfolds around a stone-clad fireplace and opens through Euro-wall glass doors to expansive outdoor living. The chef’s kitchen is both beautiful and highly functional, anchored by two oversized islands and finished with quartz countertops, tile backsplash, custom cabinetry, and a premier appliance suite including Wolf, Sub-Zero, Miele, and Vent-A-Hood. A walk-in pantry with additional prep space, a light-filled breakfast nook overlooking the bay, and a well-appointed laundry room complete the main living level. Two private primary suites on the main floor offer exceptional flexibility, each opening to terraces with pool and Intracoastal views. One features a steam shower and tailored walk-in closet, while the other is styled as a spa retreat with chandelier-lit marble finishes, a freestanding soaking tub, and a custom-designed dressing room. Upstairs, a lounge-style bonus room with wet bar and Gulf views creates an ideal gathering space, accompanied by two guest suites, both enjoying tranquil Intracoastal outlooks. The expansive lower level introduces remarkable versatility, with bonus living areas including a dedicated craft room and extensive storage rarely found in coastal homes. An indoor half-court basketball court makes this amenity driven property even more interesting. Outside, the estate truly comes into its own. A heated saltwater infinity-edge pool and spa anchor the backyard, complemented by an outdoor kitchen, pergola with gas firepit, outdoor shower, and pass-through bar for effortless entertaining. A Trex boardwalk leads to the dock and rare and irreplaceable covered 8,000 pound boat lift, offering direct Gulf-to-Bay boating with no fixed bridges. On the beach side, a grandfathered cabana is the perfect venue for enjoying specular everyday sunsets. Situated on approximately 0.82 acres, the property provides both scale and privacy, framed by mature landscaping and sweeping water views on both sides. Set on the serene barrier island of Casey Key, this Gulf-to-Bay estate offers effortless access to boating, beach, and the dining and cultural scenes of Venice and Sarasota. More than a home, 3210 Casey Key Road is a refined coastal retreat where sophisticated interiors, resort-style amenities, and exceptional waterfront living come together.

3210 Casey Key Road, Nokomis

$745,000
3 Beds 2 Baths Bellacina By Casey Key SubDv. 34275 Zip Code
** ABSOLUTELY STUNNING LAKE VIEWS IN A LIKE-NEW HOME! ** Nestled on a quiet cul-de-sac with the finest lake views in the community, this home offers an unrivaled lifestyle, combining contemporary elegance with modern convenience. It's so much more than just a great home in a fantastic neighborhood; it's designed with forever-home in mind and has tons of little touches that make it feel like home from day one. ** HOME FEATURES: * GOURMET KITCHEN * Roll-outs, Soft-Close Cabinets, and High End Stainless Steel Appliances * Produce Sink* Electric Vehicle Charging Station * COFFERED CEILINGS with CROWN MOLDING * ENORMOUS PRIMARY WALK-IN CLOSET * Electric Blinds * OUTDOOR KITCHEN with BUILT-IN GRILL, SINK, and REFRIGERATOR * Big, Open Office * PANORAMIC SCREEN PANEL OVERLOOKING THE **SPECTACULAR** LAKE WITH SUNSET VIEWS ** COMMUNITY INFORMATION: Nestled in a vibrant gated community, residents enjoy access to top-notch amenities including tennis courts, a dog park, a playground, a clubhouse with gym facilities, and a community pool. Social activities abound, fostering a sense of belonging and camaraderie among neighbors. And the best part? The LIFESTYLE - you're just minutes from downtown Venice, I-75, or the very best Gulf beaches!

15117 Vivaldi Drive, Nokomis

$2,300,000
4 Beds 6 Baths Oaks SubDv. 34229 Zip Code
This beautiful custom designed home will captivate you from the moment you  enter the front door. Located in the extremely sought after Oaks Country Club, this recently renovated home is sure to impress with picturesque views of the golf course. Privacy and entertaining are at the top of the list for this tastefully remodeled home, offering 4 bedrooms and 5 ½ baths. Marble and wood floors are in the main living areas. You are certain to have plenty of room for visiting family and friends, with a living room, fireplace, and family room all overlooking large pool area, lush landscaping, and golf course. The kitchen is waiting for your culinary skills, with stunning Quartz countertops, an island, a Thermador gas range, complete stainless appliances including double ovens with a warming drawer, extensive wood cabinetry, wine refrigeration and dining space for six. The dining room seats 12 comfortably, has handsome wood floors, and plenty of light. Two full size closet pantries offer plenty of storage space for kitchenware. The study/den has extensive built in shelving for your book collection. hurricane impact sliding doors lead you to the immense lanai, with a completely outfitted outdoor kitchen and fireplace, and multiple seating areas for dining al fresco. The generous pool and spa, all newly surfaced, are sure to complete your lifestyle. The first floor has an extremely spacious owner’s suite complete with a sitting area and three custom designed walk in closets. Also, an exercise or bonus room completes the owner’s wing. The generous bath has a walk in shower, jetted Jacuzzi, and separate vanity areas. An en suite guest bedroom is on the first floor as well. The elevator or stairs take you to the second level where you will find two en suite guest rooms complete with a cozy sitting area. This home is ready for its new owners with newer air conditioning systems, pool equipment, epoxy flooring in the 3 car garage and professional landscaping. The Oaks Country Club is a Platinum Club of America, and Emerald Club, offering two 18 hole golf courses, tennis, pickleball, croquet, fitness center, dining, and an extremely active social calendar. No need to look further, this is the one! Membership is required. Conveniently located to beautiful beaches, the Legacy

896 Macewen Drive, Osprey

$1,300,000
3 Beds 4 Baths Oaks SubDv. 34229 Zip Code
METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE VIEWS. Located in Flood Zone “X” (no flood insurance required), the home is tucked behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. The home offers 3 En Suite Bedrooms, 3 Full and 1 Half Baths. The Updated Kitchen features Quartz countertops, custom hardwood cabinetry, and premium appliances, including Sub-Zero and Wolf. A cozy family room with a wood-burning fireplace provides an inviting gathering space, while impressive Brazilian cherry hardwood flooring enhances the living and dining areas. The spacious primary suite includes a walk-in closet and a luxurious bath with dual vanities, a custom-tiled shower, and a soaking tub. Outdoor living is highlighted by a large screened and covered entertaining area, along with a stunning open-air pool overlooking the tranquil preserve. Additional features include a circular driveway and a peaceful, private setting. RECENT UPDATES include Hurricane IMPACT Windows (2019), HVAC (2021), ROOF (2014), Flooring (2020), 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**

25 Sugar Mill Drive, Osprey

$362,500
2 Beds 2 Baths Bay Street Village & Towncenter Land Condo SubDv. 34229 Zip Code
The only available home in the community with a 2 Car Garage! Welcome to Bay Street Village, a charming, beach-close, gated community in sought-after Osprey. This rarely available First-Floor residence features an oversized two-car garage with exceptional space for vehicles, bikes, kayaks, and all your Florida adventure gear. Ideally situated on a quiet cul-de-sac with peaceful pond views, this light-filled, move-in-ready home offers tranquil water vistas from both the interior and the screened lanai. The open-concept floor plan flows effortlessly, creating a comfortable and inviting living space. The owner’s suite enjoys serene pond views, while the guest bedroom is thoughtfully positioned on the opposite side of the home, adjacent to a well-appointed full bath. A stylish office/den with double-door entry provides flexible space for working from home or accommodating overnight guests. The kitchen features, stainless appliances, granite countertops along with an island with seating, and a walk-in pantry. Built with solid concrete block construction, this home includes impact windows for added peace of mind and a new (Oct 2025) HVAC system. Additional highlights include water and sewer included in the low HOA fee, no CDD fees, and a pet-friendly community. Bay Street Village offers resort-style amenities, including a heated pool, fitness room, and clubhouse—all just a short walk from your front door. Ideally located between Sarasota and Venice, you’ll enjoy easy access to shopping, dining, theater, fishing piers, kayak launches, and the Legacy Bike Trail. World-famous beaches and resorts, including Siesta Key, are just minutes away. This is a rare opportunity to own a beautiful, affordable Florida lifestyle retreat.

124 Revolution Way, Osprey

$535,000
2 Beds 2 Baths Baypointe Vista SubDv. 34229 Zip Code
Stunning, unobstructed views of the Intracoastal Waterway, Little Sarasota Bay, and the Gulf await from this beautiful Penthouse residence in Baypoint Vista, Osprey. Located within Hidden Bay, a gated and amenity rich community, this exceptional condo features 2 Bedrooms, 2 Bathrooms plus a versatile Den, an open floor plan, high ceilings, recessed lighting, a spacious kitchen, morning room, IMPACT WINDOWS AND SLIDERS, and a 2 Car Garage. The oversized primary suite is a private retreat with breath taking water views, complete with two walk-in closets, a linen closet, and a spa-like bathroom featuring a jetted soaking tub, walk-in shower, double vanity with makeup counter, and a private water closet. The second bedroom includes its own walk-in closet and en-suite bathroom, providing comfort and privacy for guests. Convenient inside utility room equipped with washer, dryer, and a separate wash basin for added functionality. Hidden Bay is a gated resort style community with a heated resort-style pool with waterfalls and lagoon style pond, hot tub, Clubhouse with library, gourmet kitchen for entertaining, fitness center, tennis and pickleball courts, fishing pier, kayak launch & storage, tiki bar, BBQ grills, Dog park, Scenic boardwalk and nature trails leading to the private pier on the bay, and an active social calendar. HOA fees cover cable, internet, water and sewer. Ideally located between Sarasota and Venice, this prime location is close to Oscar Scherer State Park, award-winning beaches - Venice Beach, Siesta Key and Nokomis, shopping, dining, medical facilities, and airports. Experience upscale waterfront living at its finest!

242 Hidden Bay Drive Unit 603, Osprey

$669,000
4 Beds 3 Baths Park Trace Estates SubDv. 34229 Zip Code
One or more photo(s) has been virtually staged. Welcome to 146 Willow Bend Way, a custom-built residence by Vision Homes in the sought-after community of Park Trace Estates. Nestled on a large lot with a pod view, this residence combines generous living spaces with a split floor plan suited for both family and guests. Featuring four bedrooms, three full baths, a den with French doors and tree car garage, the home offers flexibility for work, school, or relaxation. The open-concept layout includes formal living and dining rooms along with a spacious family room that flows into the cook’s kitchen. Highlights include a nook with an aquarium window overlooking the pool perfect for morning coffee, gas stove, real wood cabinetry, stainless steel appliances, a breakfast bar and neutral tile flooring throughout the home. Tray ceilings enhance the expansive feel, while the three-car garage and circular paver driveway provide plenty of parking and storage options. The large primary bedroom features an en-suite bathroom with a large walk in shower, garden tub and a vanity seating area. Two large walk-in closets with ample storage and a sliding door gives access to the heated pool. The split floor-plan offers privacy and the fourth bedroom with an en-suite bathroom is ideal for guests. Step outside to a screened lanai overlooking the pool and peaceful pond—a perfect setting for family get togethers or unwinding by the heated pool and spa. Osprey, herons, spoonbills and eagles are frequent visitors to the shoreline, adding a natural backdrop to everyday living. Upgrades include a new tile roof with a transferable warranty, new HVAC system, new water heater, new irrigation pump, new gas tank, hurricane-impact windows plus shutters for the sliders, and a new sink and disposal. Conveniently located near the Legacy Trail, minutes from beaches, marinas, restaurants, shopping and the acclaimed Pine View School and Oscar Scherer State Park. Easy access to both U.S. 41 and I-75 puts everything within reach, while the home remains tucked among preserved green space for added privacy and calm. Experience comfort, convenience and the best of Florida living in Park Trace Estates—schedule your visit today.

146 Willow Bend Way, Osprey

$565,000
3 Beds 2 Baths Southbay Yacht & Racquet Club SubDv. 34229 Zip Code
Price was dropped $50,000 on 5/7! Survey and pool quote are available! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining room to the left and hallway to the family room, kitchen, and dinette straight ahead. The entire interior has been professionally painted in 2025, and there is tons of natural light that flows through the many windows of this home. The kitchen is open to the family room and dinette for easy entertaining. There is also a HUGE bonus room toward the back of the home. Next to the family room is entrance to the hallway leading to the two guest bedrooms and guest bathroom. On the opposite side of the home, past the dining room is the spacious primary suite with generous walk-in closet and ensuite bath. The laundry room is located near the family room. Entrance to the attached 2 car garage is near the foyer. Roof was replaced in 2022 & AC was installed in 2016. The entire house has also been replumbed! Southbay Yacht & Racquet Club is an active lifestyle community with many social, boating, and sports activities. The clubhouse has recently been renovated and features a community pool, fitness center, ballroom, two kitchens, card room, game room, and an elevator! Additional amenities include 3 tennis courts, 4 pickle ball courts, basketball, playground, bocce, shuffleboard, and miles of walking trails and green space. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf.  The community is welcoming and lively—perfect for families and those who enjoy an active, coastal lifestyle. This community is in the perfect location with several warm gulf beaches, Downtown Venice & Downtown Sarasota close by. The famous Casey Key Fish House and Tiki Bar are just a golf cart ride away! Oscar Scherer State Park is across Tamiami Trail and Pine View (#1 school in the state) is about 5 minutes away. This home is ready for you to start living the elevated Southbay lifestyle! **The street behind this house (Blackburn Point Rd.) is a fairly quiet two lane Rd. That's the road you can take your golf cart to Casey Key Fish House & Tiki Bar!**As of Jan 2026, there is marina space available immediately (no wait list) and fees range between $169-$705 per quarter depending on what size you require.This is subject to change.**This listing went pending in March. When the buyers couldn't secure their financing, it went back on market. No inspections have been done.**

186 Windward Drive, Osprey