Refine Search
Sort by
33 Bishops Court Road Unit 118, Osprey
$679,000
2 Beds ⋅ 3 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
**EXPERIENCE EFFORTLESS LIVING in this BEAUTIFULLY UPDATED TOWNHOUSE with SERENE WATER VIEWS** Located behind the Secure Gates of The Oaks Preserve, Golf & Country Club neighborhood, this delightful residence features 2 En Suite Bedrooms on the 2nd Floor, 2 Full and 1 Half Baths, and offers a refined yet relaxed lifestyle surrounded by mature oak canopies and tranquil lake views. The main living area entails an inviting great room that opens to serene water views framed by palms and natural greenery while the European-style kitchen is thoughtfully designed with premium SubZero, Wolf and Bosch appliances, modern wood cabinetry, polished granite countertops, and durable ceramic tile flooring—ideal for both everyday living and entertaining. Architectural details add warmth and character throughout, including hand-plastered walls with art niches, graceful archways, plantation shutters, and sisal carpeting. Just off the entry foyer, you’ll find a convenient powder room and a separate laundry room. A private brick balcony provides ample space for outdoor dining or relaxing while enjoying the peaceful surroundings. The primary suite overlooks the lake and includes two walk-in closets and a spacious bathroom featuring dual vanities, walk-in shower, jacuzzi tub and appointed with upscale finishes. The guest suite is equally comfortable, complete with built-in shelving and ample storage. 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 lighted), 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.

33 Bishops Court Road Unit 118, Osprey

700 Shadow Bay Way, Osprey
$655,000
3 Beds ⋅ 3 Baths ⋅ Rivendell SubDv. ⋅ 34229 Zip Code
Welcome to 700 Shadow Bay Way, an impressive 3-bedroom, 2.5-bath pool home with a den, 3-car garage and more than 2,500 square feet of living space in the highly desirable Woodlands at Rivendell. Set on an oversized corner lot, this spacious home offers a bright, open and functional floor plan with high ceilings, crown molding, a generous great room and a separate dining area ideal for both everyday living and entertaining. The den provides valuable additional space for a home office, library or possible fourth bedroom. The spacious eat-in kitchen offers abundant cabinetry and counter space, a breakfast bar, walk-in pantry and an open connection to the main living areas. The private primary suite includes direct access to the lanai, two walk-in closets and an ensuite bath with dual vanities, soaking tub and separate shower. Step outside to an expansive screened lanai surrounding the pool and spa, with a covered seating area and plenty of room to relax or entertain. Additional highlights include a split-bedroom layout, inside laundry, brick-paver driveway and walkway, mature landscaping and an attached 3-car garage. Rivendell is known for its tree-lined streets, lakes and natural surroundings, with a convenient Osprey location near Pine View School, Oscar Scherer State Park, shopping, dining, Gulf beaches, Venice and Sarasota. A wonderful opportunity to enjoy generous living space, a private pool and the Florida lifestyle in one of Osprey's established communities.

700 Shadow Bay Way, Osprey

110 Pine Avenue, Osprey
$649,000
3 Beds ⋅ 2 Baths ⋅ Osprey Avenue Sub SubDv. ⋅ 34229 Zip Code
Heart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your RV and all your toys. Lots of room for storage. Enjoy sunsets, steps to fishing pier, kayak launch, Spanish Pointe, Oscar Scherer State Park, and Pine View School. No restrictions. Move-in ready enjoying the Florida lifestyle! For outdoor enthusiasts, this location is unbeatable. Launch your kayak or paddleboard from a few steps away into Sarasota Bay, explore Mid night pass, Siesta Beach, nearby Bay Preserve at Osprey and Historic Spanish Point, close to Oscar Scherer State Park, Casey Key, Nokomis Beach. The large backyard offers plenty of space for entertaining, playing, or simply soaking in Florida’s year-round sunshine. Whether you're looking for a family home, a. vacation retreat, or a profitable rental property

110 Pine Avenue, Osprey

1036 Oak Meadow Lane, Osprey
$630,000
4 Beds ⋅ 2 Baths ⋅ Rivendell SubDv. ⋅ 34229 Zip Code
Completely renovated St. Charles floor plan in the highly desirable Woodlands community of Rivendell. You must see to believe the upgrades! Just half a block to the community pool and less than five minutes to the renowned Pine View School for the intellectually gifted.Enjoy stunning brand-new granite countertops in the kitchen and bathrooms, plus beautiful ceramic tile flooring throughout the entire home for easy durability and maintenance. Gain total peace of mind with a new tile roof installed in 2023 and a new air conditioning system from 2024, making this home truly move-in ready. Located just minutes from world-famous Gulf beaches, shopping, and entertainment, this property features low HOA fees and an unbeatable location.

1036 Oak Meadow Lane, Osprey

3603 N Point Road Unit 202, Osprey
$629,400
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Virtually Staged. EXCEPTIONALLY SPACIOUS CORNER CONDO – NEARLY 3,200 SF – NO WAITLIST FOR GOLF MEMBERSHIP! Ideally situated behind the gates of the highly sought-after Oaks Preserve, this elegant and beautifully appointed corner residence offers an impressive combination of space, privacy, and resort-style living. The nearly 3,200 SF open floorplan features 3 en-suite bedrooms and 3 baths, providing exceptional comfort and flexibility. Light and bright throughout, the residence showcases crown molding, engineered hardwood flooring, and an expansive kitchen with granite countertops and stainless-steel appliances. Enjoy the serene, private preserve setting from multiple screened balconies, enhanced by convenient remote-controlled automatic hurricane shutters. Additional features include 2 assigned parking spaces, including 1 under-building space, plus climate-controlled storage. A rare opportunity to enjoy substantial living space, privacy, and the exceptional lifestyle of The Oaks! This NEWEST Tower (built in 2007) in the Meridian Condo Complex features Hurricane Impact Windows and Doors and is conveniently located next door to the condo residents’ private Amenity Center featuring Heated Pool & Spa, Fitness Room and outdoor grill in addition to The Oaks Club’s main campus of amenities. 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, 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. **A MUST SEE**

3603 N Point Road Unit 202, Osprey

250 Hidden Bay Drive Unit 302, Osprey
$625,000
3 Beds ⋅ 2 Baths ⋅ Edgewater/Hidden Bay Ph 1 Bldg SubDv. ⋅ 34229 Zip Code
LOCATION, LOCATION, LOCATION! Experience waterfront living in this beautifully upgraded luxury condominium, ideally located in a gated, resort-style community nestled between US 41 and Little Sarasota Bay. The residence features 3 bedrooms, a den, and 2 full bathrooms. With no building or walkway directly behind the unit, the property also offers a peaceful sense of privacy. Step inside to an open-concept layout where the kitchen, dining, and living areas flow seamlessly together. High ceilings, elegant tray ceilings with crown molding, and hurricane-impact windows and sliding glass doors fill the home with natural light while creating a beautiful connection to the outdoors. Both the living area and primary suite open to an oversized screened balcony—an exceptional outdoor living space offering panoramic views of the bay, Casey Key, the Gulf, and surrounding preserves. Enjoy watching boats and wildlife while taking in spectacular sunsets from your own private outdoor retreat. The well-appointed kitchen features an expansive area of granite countertops, stainless steel appliances, and ample cabinetry. The spacious primary suite offers two walk-in closets and a large en-suite bathroom with dual split vanities. The second en-suite bedroom features a generous walk-in closet and a convenient pocket door providing access to the second bathroom. A full-size laundry room located inside the unit adds everyday convenience. Designed for easy living, the residence offers elevator access, two parking spaces including one assigned space, and a private storage room beneath the building. The condominium fee includes building and flood insurance, reserves, internet, cable TV, exterior maintenance, pest control, and water, providing convenient, low-maintenance ownership. The gated community offers a resort-style setting with a heated pool and spa, expansive sundeck, grilling area, pickleball and tennis courts, kayak storage and launch, and a scenic boardwalk through the mangroves leading to a fishing pier. The clubhouse features a catering kitchen, library, fitness room, and additional gathering spaces. The location is hard to beat, conveniently positioned between Sarasota and Venice, with approximately 6.5 miles to Siesta Key and Nokomis Beach, less than one mile to Bay Street Park and Osprey Dog Park, approximately 2 miles to the Legacy Trail Osprey Junction and Casey Key, and approximately 3 miles to Oscar Scherer State Park. An array of restaurants, shopping, marinas, golf, and medical services are also conveniently nearby. Whether you're looking for a full-time residence, vacation home, investment property, or a convenient lock-and-leave lifestyle, this waterfront condominium brings together privacy, exceptional water views, extensive upgrades, resort-style amenities, and a highly desirable location. Come experience the views and discover the possibilities this property offers.

250 Hidden Bay Drive Unit 302, Osprey

385 N Point Road Unit 402, Osprey
$615,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
**BEAUTIFULLY UPDATED CONDO with MARVELOUS VIEW** features 3-BEDS and 3-FULL BATH, Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Impressively Renovated interior which boasts Engineered Hardwood and designer Wood Plank Tile flooring, Plantation Shutters, a well-equipped Kitchen with granite counter seating area, white cabinetry and Stainless-Steel appliances including Bosch etc. The Owner’s Bedroom Suite features a Walk-in Closet, Dual Vanities, Soaking Tub and Stunning, Custom Tiled Shower. The Spacious, Screened Balcony features lovely new tile flooring and automated Hurricane Shutters, offering a PRIVATE and serene setting where you can view wonderful wildlife and Gorgeous Sunsets! This residence offers a single, covered parking space and a climate-controlled storage unit. Meridian Condo residents enjoy private amenities including Heated Pool & Spa, Fitness and Outdoor Grill in addition to The Oaks Club’s main campus of amenities. 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.

385 N Point Road Unit 402, Osprey

458 N Shore Drive, Osprey
$600,000
Sorrento Shores SubDv. ⋅ 34229 Zip Code
Discover the perfect canvas for your dream home with this exceptional vacant lot located in the desirable Sorrento Shores community in Osprey, Florida. Spanning 0.34 acres, this spacious lot offers ample room for creative design and construction. Featuring a generous 100-foot frontage and dimensions that allow for multiple building possibilities, this property is ideal for those looking to build a custom residence in a serene setting. Conveniently situated between US 41 and the Intracoastal Waterway, you'll enjoy the best of both worlds: easy access to local amenities while being surrounded by Florida's natural beauty. The RSF1 zoning permits single-family residential homes, making it an excellent opportunity for families or individuals seeking to establish themselves in a peaceful neighborhood. Embrace the lifestyle you've always wanted in Osprey, where you can enjoy boating, fishing, nearby beaches and a welcoming community. Don't miss the chance to invest in this prime piece of real estate; schedule a visit today and start envisioning your future in Sorrento Shores. Permit-ready plans available separately. Owner-agent.

458 N Shore Drive, Osprey

5100 Jessie Harbor Drive Unit 404, Osprey
$599,000
2 Beds ⋅ 2 Baths ⋅ Blackburn Harbor SubDv. ⋅ 34229 Zip Code
Sweeping water views, beautiful updates and an enviable waterfront lifestyle come together in this exceptional fourth-floor residence at Blackburn Harbor. Docking available on the premises for a very reasonable quarterly fee. Set along South Creek with direct access via canal to the Intracoastal Waterway and the Gulf, this spacious 2-bedroom, 2-bath home with a versatile den captures the essence of coastal Florida living, from spectacular sunsets and gentle sea breezes to easy access for kayaking and boating. Thoughtfully renovated, the residence offers a fresh, modern feel with laminate wood flooring throughout, plantation-style window shutters, updated lighting and new vertical drapery on the sliding doors. The open living and dining areas flow seamlessly to the spacious screened lanai, where expansive water views create a beautiful setting for morning coffee, afternoon relaxation or sunset entertaining. The updated kitchen features quartz countertops and backsplash, stainless-steel appliances replaced in 2022, a new faucet and disposal, and thoughtfully added cabinet drawers for enhanced storage and functionality. Both bathrooms were beautifully updated in 2022 with new cabinetry, sinks, granite countertops, backsplashes, faucets, mirrors and fresh paint. The spacious primary suite enjoys tranquil water views, three closets—including two walk-ins—and a generous ensuite bath. The guest bedroom features a walk-in closet and convenient access to the second bath, creating a comfortable private suite for guests. The den adds valuable flexibility as a home office, reading room or occasional third bedroom. Additional improvements include a new HVAC system in 2023, water heater, washer and dryer in 2022, and a new metal community roof installed in 2025. HOA fees include water, sewer, cable and Wi-Fi, leaving electric as the primary utility expense. Blackburn Harbor is an inviting gated waterfront community surrounded by lush tropical grounds and an active social atmosphere. Residents enjoy a heated pool, fitness center, tennis, pickleball, shuffleboard, clubhouse, walking paths, waterside gathering areas, grills and a kayak launch. Boat dockage is available for approximately $252 per month, offering the rare opportunity to keep your boat close to home and enjoy the waterways at your leisure. Located minutes from Nokomis Beach, the Legacy Trail, Oscar Scherer State Park, shopping and dining, this is a wonderful opportunity to enjoy the best of the Sarasota-area waterfront lifestyle—with the updates already done and nothing left to do but settle in and enjoy.

5100 Jessie Harbor Drive Unit 404, Osprey

143 Osprey Point Drive, Osprey
$575,000
Oaks SubDv. ⋅ 34229 Zip Code
One of the last available homesites in The Oaks Bayside. Almost 1/2 acre, at 17,647-square-feet, this exceptional lot presents a rare opportunity to build a custom luxury residence in one of Sarasota's most established and prestigious gated communities. Located behind the 24-hour staffed gates of The Oaks Bayside, this desirable homesite is ready to be transformed into the home you've always envisioned. Bring your own builder and architect and create a residence tailored to your lifestyle, surrounded by majestic oak trees, winding streets, and distinctive estate homes. The Oaks Bayside is renowned for its peaceful Old Florida charm, mature landscaping, and prime location along Little Sarasota Bay. This sought-after neighborhood offers a unique blend of privacy, natural beauty, and convenience, just minutes from the beaches of Casey Key, downtown Sarasota, and the area's finest shopping, dining, and cultural attractions. Ownership includes membership in The Oaks Club, one of Florida's most respected private club communities, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, croquet, a state-of-the-art WellFit Center, Junior Olympic heated swimming pool, bocce, basketball, playground facilities, multiple dining venues, and a vibrant year-round social calendar. Club membership is required, and there is currently NO WAITING LIST for either Golf or Sports/Social membership.

143 Osprey Point Drive, Osprey

409 N Point Road Unit 502, Osprey
$575,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
**GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The coveted lifestyle of The Oaks Country Club with the convenience and amenities of maintenance-free condominium living come together at this Gorgeous Meridian 5th floor residence. Upon exiting the elevator into the private foyer, step inside and enjoy the breathtaking panoramic preserve, bay and Gulf of Mexico views! The dramatic step ceiling defines the foyer space while leading into the expansive dining room, living room and open kitchen featuring Granite countertops and Stainless Steel appliances. Both the primary bedroom suite and living room open to the balcony extending the sweeping views and providing ample outdoor living space. Premium features include Crown Moldings, High Ceilings, Luxury Vinyl Plank flooring, recently Painted Interior, etc. Owner’s Bedroom Suite features Walk-in Closet, Custom Tiled Shower, Soaking Tub and Dual Vanities, a 2nd En Suite Bedroom with walk-in closet, etc. NEW HVAC (Sept., 2024); Hurricane Impact Windows & Doors PLUS Hurricane Shutters across Balcony. This residence also offers a single covered parking space directly outside of lobby door and a climate-controlled storage unit. Meridian Condo residents enjoy private amenities including Heated Pool & Spa, Fitness and Outdoor Grill in addition to The Oaks Club’s main campus of amenities. 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.

409 N Point Road Unit 502, Osprey

2046 Cordes Street, Osprey
$565,000
3 Beds ⋅ 2 Baths ⋅ Cordes Cove SubDv. ⋅ 34229 Zip Code
Virtually Staged. Nature Lovers Paradise! Tucked along a tranquil creek with direct water access to the Gulf of Mexico, this elevated 1,705 sq ft home sits on almost a 12,000 sq ft lot offering the perfect blend of coastal adventure and peaceful natural surroundings. Launch your paddle craft right from the yard and paddle out to open water, or cast a line from your private fishing dock. The fishing here is easy and the setting couldn't be more scenic. The home offers 3 bedrooms and 2 baths, with the primary suite privately situated on the entire second floor featuring a spacious walk-in closet and abundant storage. Downstairs, heart pine flooring flows through the living area, warmed by a cozy wood-burning fireplace on cooler evenings. A screened wraparound porch on the first level extends your living space outdoors, ideal for morning coffee or evening breezes off the creek. This home is ready for your personal touch and is an incredible opportunity to update and build instant equity in a location that can't be replicated. The elevated design offers peace of mind along with sweeping views of the creek and surrounding woods. Outside, the yard is a true nature lover's dream--idyllic and alive with birdsong, from herons to osprey, all just steps from your door.

2046 Cordes Street, Osprey

Osprey
$562,900
Phase 2 Of Bay Street SubDv. ⋅ 34229 Zip Code
Why lease when you can own your own commercial space? This exceptional 1,204± square foot ground-floor commercial condominium offers an outstanding opportunity for medical, dental, wellness, legal, financial services, insurance, real estate, boutique retail, café, or professional office users in one of Osprey's most desirable mixed-use developments. Currently operating as a charming café/bistro, the suite features an open and inviting layout with abundant natural light, attractive storefront windows, a private restroom, and excellent visibility. The existing improvements can easily be adapted to accommodate a wide variety of commercial uses. Built in 2008, the space is located within a Class A building in Bay Street Village & Town Center. Positioned directly on highly traveled US Highway 41 (Tamiami Trail), this property is perfectly situated to benefit from the exciting new Margaritaville Hotel, coming directly across the street, bringing increased tourism, traffic, and business activity to the area. Bay Street Village offers a vibrant, walkable environment surrounded by professional offices, retail shops, restaurants, and residential communities. The property enjoys excellent accessibility with close proximity to Interstate 75, Casey Key beaches, Sarasota, and Venice, making it an ideal location to serve clients throughout South Sarasota County. The property features approximately 1,204 square feet of ground-floor space with outstanding frontage and visibility on US Highway 41. Additional amenities include approximately 70 shared parking spaces, monument and storefront signage opportunities, 24-hour access, fiber optic internet, wheelchair accessibility, an attractive courtyard setting, and neighboring professional businesses, including Osprey Dental. Added Value: The owner is a licensed general contractor and is willing to assist the new owner with interior renovations, build-outs, or improvements at a discounted rate. This unique offering can substantially reduce renovation costs while allowing the space to be customized quickly and efficiently to meet your business needs. Whether you're looking to establish your business in a premier location or invest in a quality commercial property with long-term upside, this is a rare opportunity to own instead of lease in one of the area's fastest-growing commercial corridors. Added Value: The owner is a licensed general contractor and is willing to assist the new owner with interior renovations, build-outs, or improvements at a discounted rate. This unique offering can substantially reduce renovation costs while allowing the space to be customized quickly and efficiently to meet your business needs.

Osprey

409 North Point Road Unit 401, Osprey
$560,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Nestled at treetop level, in Meridian behind the gates of The Oaks Preserve, you will find this elegant residence waiting for you to make it your own. With a spacious master suite, two guest bedrooms (one en suite) and a den, this condo lives large, with room for comfortable, gracious living. Beautifully appointed, every special touch you would want can be found here, Italian ceramic tile, crown molding, ceiling fans and custom lighting. The expansive kitchen features granite countertops and stainless-steel appliances and has a cozy breakfast nook. Practical concerns are addressed by things like electric hurricane shutters in addition to impact windows and doors, and a large laundry room. Meridian residents have use of their own pool, spa and workout room. And can take advantage of all the Oaks Club has to offer, two championship golf courses, a world-class tennis facility, a state-of-the art wellness center and a wide variety of club amenities, including dining options and social offerings. There is currently no waiting list for either Golf or Sports/Social membership.

409 North Point Road Unit 401, Osprey

1346 Thornapple Drive, Osprey
$540,000
3 Beds ⋅ 2 Baths ⋅ Willow Bend SubDv. ⋅ 34229 Zip Code
Welcome to Willowbend, where quiet meandering streets of manicured lawns live, and so can you! Well respected Builder, Lee Wetheringon built sturdy homes and this one will not disappoint! Every bell and whistle upgrade! Open your double stained glass front door to the foyer. Views of a peaceful lake and enormous great room greet you! Double tray ceiling has optional lighting feature and adds layers to the already extra, high quality custom built-ins. Taller doors grace the rooms throughout... Dining room is spacious enough for a large dining table. Convenient custom built-in sideboard for seasonal storage or serving pieces! Great room is 'just that', it's big! Sliding doors open to caged lanai and lakeside views. Kitchen is expansive and has a broom closet and pantry! Southern exposure and extremely high ceilings keep this house light and bright. Breakfast area has 3 panels of aquarium glass windows. Take a peek! But wait, there's much more! The master suite is substantial! More than spacious, it offers a peaceful sitting area also overlooking the lake and lanai. There are two walk-in closets! Double sinks in the master bath, along with a garden tub and water closet. Once again, light and bright! The 3rd bedroom, (has a closet), has been turned into an office! Get a lot of work done here! State of art custom cabinetry! Lovely... Bedroom #2 has its own wing with a full bath. This home has gas in place for the water heater, laundry, etc. The laundry room features a gas Fisher-Paykel laundry set and deep sink! Garage also has lots of storage! Community pool and small clubhouse close by! HOA provides all lawn services, to include care of shrubbery. Conveniently located close to both Sarasota and Venice. Willowbend is a short distance to Nokomis Beach, the wonderful waterfront restaurants off Blackburn Point and Laurel Road, Legacy Bike Trail and Historic Marie Selby Spanish Point! Costco is close and so will be the Trader Joes and Whole Market, both of which are being built! This home is special...

1346 Thornapple Drive, Osprey

1140 Beachcomber Court Unit 11, Osprey
$540,000
3 Beds ⋅ 3 Baths ⋅ Blackburn Point Marina Village SubDv. ⋅ 34229 Zip Code
Virtually Staged. Welcome to Blackburn Point Marina Village, an intimate gated waterfront community of just 19 residences near Sarasota and Casey Key. This beautifully upgraded townhome delivers a relaxed coastal lifestyle with low-maintenance living—without the waterfront price tag. A bright, open floor plan features 9-foot ceilings, plantation shutters, ceiling fans, and new luxury vinyl flooring installed in 2025. The enclosed sunroom adds versatile living space for relaxing, entertaining, or enjoying the Florida sunshine. The gourmet kitchen is designed for both everyday living and entertaining, with granite countertops, Craft Maid cabinetry, a KitchenAid gas range, LG refrigerator (2023), and wine refrigerator. Enjoy peace of mind with a new roof (2025), water filtration and softener system (2024), tankless water heater, motorized hurricane shutters, epoxy-finished garage floor, and a LiftMaster garage door with camera (2025). The first-floor primary suite provides a private retreat, complete with dual vanities, a soaking tub, and a walk-in shower. Ideally located near Casey Key Marina, Blackburn Point Park, and Casey Key Fish House & Tiki Bar, this home puts boating, waterfront dining, and outdoor recreation close at hand. Community amenities and water and gas service are included, making this an exceptional opportunity to enjoy the Sarasota coastal lifestyle. One or more photo(s) was virtually staged.

1140 Beachcomber Court Unit 11, Osprey

3621 N Point Road Unit 301, Osprey
$525,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Ready to live a stress-free luxury condo lifestyle? There is no place better to do it than this 3 bedroom, 3 bath residence in Meridian at The Oaks Preserve. Nestled among the treetops, this end unit has a split floor plan and absolutely breathtaking sunset views over the Preserve and out to Little Sarasota Bay. Natural light floods the interior, highlighting the beauty of the hand-rubbed walnut floors. The kitchen with high-end stainless-steel appliances including a subzero refrigerator, has a breakfast bar, room for a café table and overlooks the dining room. The master bedroom has two large walk-in closets, a spacious en suite bathroom with separate shower and soaker tub. A sliding door to the screened balcony allows you to enjoy your morning coffee as the soothing sounds of awaking nature surround you. The additional 2 en suite bedrooms allow for room and privacy for guests and your loved ones. This well maintained unit has many other features, a large laundry room with utility sink and a good number of cabinets for storage, electric hurricane shutters, ceiling fans, plantation shutters and more. The Meridian residents-only pool, spa and workout room are just steps away. The Oaks, Sarasota’s finest golf and country club, has 2 championship 18-hole golf courses, 12 HAR TRU tennis courts (4 lighted), 4 pickleball courts, a Wellfit Center, 3 onsite restaurants, and a wide variety of social and recreational activities. The location, in the heart of Osprey, is superb. Just a short drive to almost anything you would want or need while living a maintenance-free lifestyle on Florida’s beautiful Gulf Coast. There is currently no waiting list for either Golf or Sports/Social membership.

3621 N Point Road Unit 301, Osprey

4428 Conchfish Lane, Osprey
$525,000
4 Beds ⋅ 2 Baths ⋅ Palms/Casey Key SubDv. ⋅ 34229 Zip Code
Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into the kitchen, and you'll find elegant quartz countertops, upgraded 42" Timberlake latte cabinets, a stylish backsplash, a large walk-in pantry, and stainless-steel appliances. The master retreat offers a tranquil area with a spacious bedroom. Plantation shutters and 18x18 tiles complemented by hard floors throughout the entire house. The residence has hurricane shutters, Low-E windows, and a generator hook-up. A large 26x10 covered lanai provides space for relaxing and entertaining. The Palms at Casey Key is a lovely neighborhood with low HOA fees that offers a sense of privacy. Imagine the ease of having your boat just minutes away at the nearby Casey Key Boat Launch, ready whenever you are. They say location is everything, and this home truly delivers on that promise. Ideally situated, it offers immediate access to everyday conveniences: restaurants, grocery stores, and a quick connection to I-75. Dog lovers will appreciate the brand-new dog park nearby, perfect for playtime and socializing. Just under a mile from your front door, the Casey Key Boat Launch and the lively Tiki Bar invite you to unwind and enjoy days by the water. Families will love the close proximity to the prestigious Pine View School, renowned for academic excellence and ranked as the number one high school in Florida, the second-highest elementary school in the US, and the third-highest middle school in the US. Beyond the neighborhood, you'll find easy access to Siesta Key Beach, top-tier golf courses, vibrant cultural attractions, and exciting entertainment options. With low HOA fees and no CDD fees, this home offers the freedom to live your dream Florida lifestyle, without the rising costs of new construction. Move-in ready and like-new, this residence is a perfect blend of character and delightful charm. Store your boat, enjoy the community, and embrace life with ease and comfort. Don’t miss your chance to claim your own piece of paradise!

4428 Conchfish Lane, Osprey

4429 Conchfish Lane, Osprey
$499,999
3 Beds ⋅ 2 Baths ⋅ Casey Key SubDv. ⋅ 34229 Zip Code
Virtually Staged. MOTIVATED SELLER- SPACIOUS 2,000+ SQ FT HOME, UPDATED BEDROOM FLOORING, PRIVATE BACKYARD, COVERED LANAI & 2-CAR GARAGE in The Palms of Casey Key, offering a comfortable layout designed for both everyday living and entertaining. The inviting interior features UPDATED FLOORING THROUGHOUT THE BEDROOMS & CLOSETS with durable tile in the main living areas for easy maintenance. A spacious great room provides plenty of room to gather, while the private primary suite is tucked away at the rear and features DUAL SINKS, SOAKING TUB, WALK-IN SHOWER & GENEROUS CLOSET SPACE. Step outside to the COVERED LANAI & PRIVATE BACKYARD, perfect for enjoying your morning coffee or hosting friends and family. Additional highlights include a 2-CAR GARAGE and a well-maintained community with HOA oversight and nearby amenities. Located JUST STEPS FROM PINE VIEW SCHOOL with easy access to US-41 and I-75, this home puts TOP-RATED SCHOOLS, BEACHES, MARINAS, DINING & SHOPPING within minutes.

4429 Conchfish Lane, Osprey

2309 Jessie Harbor Drive Unit 2402, Osprey
$480,000
3 Beds ⋅ 3 Baths ⋅ Blackburn Harbor Waterfront Villas SubDv. ⋅ 34229 Zip Code
West-Facing Canal Views in Gated Blackburn Harbor. This second-floor, 3-bedroom, 2.5-bath condo in Blackburn Harbor Waterfront Villas puts you directly on the canal with west-facing views that make sunsets a daily event worth watching. At 2,006 square feet, the layout is spacious and light-filled — vaulted ceilings in the living, dining, primary suite and kitchen areas, two sets of sliding glass doors opening to a screened lanai over the water, and side windows that keep natural light moving through the unit all day. Canal views extend from the main living and dining areas into the primary suite, giving the heart of the home a constant connection to the water. The primary suite features a private slider to the lanai, dual closets, and an ensuite bath with dual sinks, a jetted garden tub, and a walk-in shower. The second bedroom is a spacious ensuite with a walk-in closet. The third bedroom, with its French doors, works equally well as a guest room, home office, or flex space. The kitchen and ensuite baths feature solid wood cabinetry and granite countertops. Updated stainless steel appliances complete the kitchen. Major systems: A/C (2016), water heater (2021). Blackburn Harbor is a gated, 11-acre waterfront community with a heated pool, tennis and pickleball courts, BBQ gazebo, kayak storage and launch, and a boat dock rental program (subject to availability), with easy access to the Intracoastal Waterway and the Gulf of Mexico just beyond. No trailering, no storage hassles — just head out on the water and return to the convenience of your own dock. HOA: $980/month. Pets welcome up to 40 lbs. Minutes from Nokomis Beach, The Legacy Trail, Downtown Venice, Oscar Scherer State Park, Sarasota Memorial Hospital Venice Campus, nationally acclaimed Pine View School, and the dining and shopping along US-41 — centrally located between Sarasota and Venice. Minutes away from I-75 and the 681 connector. A rare opportunity to live, entertain, and boat from the same address. Schedule your private showing today.

2309 Jessie Harbor Drive Unit 2402, Osprey

401 N Point Road Unit 301, Osprey
$459,900
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Virtually Staged. Short Sale. Enter through the secure foyer and take the private elevator to the third floor where you will find this charming 3 bedroom, 3 bath residence. Situated at treetop level, overlooking the preserve and surrounding lush foliage, the interior is open and neutral, with lots of natural light. This unit is waiting for you to come and put your decorating touches on it and make it uniquely your own. Check out the virtually staged photos to help you imagine what you could do with this great floor plan. This condo offers space for year-round living, or to use as a welcoming winter retreat, with room for family and friends to visit. Wouldn’t it be lovely to sit on the private terrace and listen to the birds sing as the sun sets on another perfect day? The unit has a one car under building parking space. It is a short walk to the Meridian residents-only fitness room, spa and heated pool. The Oaks Club has two championship golf courses, 12 HAR TRU tennis courts (4 lighted), croquet and pickleball courts, a state-of-the art fitness center, junior Olympic community pool, and offers a wide variety of dining and recreational options, and social activities. When you open the door to your new home here, you have opened the door to the best in Gulf Coast country club living. Membership in The Oaks Club is required with homeownership. There is currently no waiting list for either Golf or Sports/Social membership.

401 N Point Road Unit 301, Osprey

7303 Jessie Harbor Drive Unit 7303, Osprey
$449,000
3 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code
Welcome to luxury coastal living in this exceptional 3rd-floor penthouse condo nestled in the secluded, resort-style waterfront community of Heron House in Osprey. Offering 1,883 sq. ft. of beautifully light-filled, fully furnished living space, this impressive 3-bedroom, 2-bathroom residence features high-end finishes, warm hardwood floors, plantation shutters, a decorative wood-burning fireplace, and a built-in wet bar perfect for entertaining. The gourmet kitchen is equipped with rich wood cabinetry, granite countertops, stainless steel appliances, and a cozy eat-in breakfast area. Unwind in the expansive primary suite boasting two walk-in closets, a spa-like bath with double vanities, a deep soaking tub, and a separate shower. Step outside onto multiple private balconies to take in tranquil views of lush tropical greenery and calm canal waters—an idyllic setting for outdoor dining or evening cocktails. Located directly on Jessie Harbor with bridge-free, direct access to the Intracoastal Waterway and the Gulf, this gated community offers extraordinary waterfront amenities, including a kayak launch, boat slips (available on a first-come, first-served basis), and frequent visits from local wildlife like otters and dolphins. Residents enjoy a highly active, beautifully maintained HOA complete with a newly installed entrance security gate, heated pool, water aerobics, tennis and pickleball courts, shuffleboard, clubhouse, fitness center, walking trails, locked storage, bike storage, and two assigned covered parking spaces under the building with elevator access. Situated just 10 minutes from Venice Beach, Nokomis Beach, and Casey Key, 20 minutes from world-famous Siesta Key, and minutes from I-75, Oscar Scherer State Park, the Legacy Trail, and Sarasota’s vibrant cultural hub, this hidden gem combines peaceful privacy with unbeatable access to Florida’s finest coastal living.

7303 Jessie Harbor Drive Unit 7303, Osprey

524 Sarabay Road, Osprey
$419,000
3 Beds ⋅ 2 Baths ⋅ Bay Acres Sub SubDv. ⋅ 34229 Zip Code
Location, Location. In the Heart of Osprey, centrally located in the highly sought-after well-established Bay Acres Community. Lowest priced home west of the Taril. These 3 bedrooms 2 bath ranch home is West of 41 within 10-minute commutes to downtown Sarasota and downtown Venice, Florida. Across the street from Walmart with bus transportation to Sarasota and Venice. You can walk to Walmart, the post office and two Tiki bars. You can launch your kayak from the private waterfront park on a protected bay with dockage for boats up to 22 feet. There is a waiting list for the dockage. Bay Acres is a non-deed-restricted neighborhood. You can park your RV or commercial vehicles on your property. Major updates include new roof, 3 years old, exterior paint 3 years, New HVAC this year, a Water treatment system recently installed and a rescreened lanai. Some interior updates have been done, but most need personal touches. This house has a new neighbor owned fence at the back of the lot and no fence at either side. The lot is large enough for a pool.

524 Sarabay Road, Osprey

418 S Tamiami Trail Unit E3, Osprey
$415,000
Osprey Executive Park SubDv. ⋅ 34229 Zip Code
Studio E3 at Osprey Executive Park is a fully renovated executive suite built for businesses that take their image seriously. Step into the reception area and you're greeted by a stone accent wall and fireplace a combination that feels warm without losing its polish. Designer tile runs throughout the suite, tying the space together and setting the tone before a single meeting starts. The layout includes three private offices and a generous conference room, each fronted with glass doors that keep the space feeling open while still giving your team the privacy they need. It's a floor plan that works equally well for client meetings, team collaboration, or quiet, focused work. The kitchen is where the suite really shows its quality soft-close wood cabinetry, marble countertops, and a stone backsplash that wouldn't look out of place in a high-end home. Even the restroom carries the same attention to detail, with a full-length vanity and finishes to match the rest of the space. Two separate storage rooms round things out, giving you somewhere to keep files, supplies, and equipment without cluttering the work areas. This isn't just office space it's a setting that tells clients something about who you are before you say a word.

418 S Tamiami Trail Unit E3, Osprey

1811 Highland Road, Osprey
$409,900
2 Beds ⋅ 2 Baths ⋅ Towns-End Shores SubDv. ⋅ 34229 Zip Code
PRIVATE NEIGHBORHOOD - Fully Furnished 2 Bedroom Townhouse in the Casey Key area, QUAINT, SPACIOUS 2-CAR Tandem GARAGE + Carport, modern, high ceilings, kitchen upgrades, screened balcony, 2 beds + den; 2 baths; living area and kitchen open plan; community pool Conveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches. Walking distance to Casey Key Mainland (Chef Rolfs), private community Shoreland Park & Oscar Scherer State Park. Minutes away from COSTCO, Publix, Target, Richard's, YMCA Potter Park, waterfront dining (Casey Key Fish House & Tiki bar - waterfront , Spanish Point restaurant & Tiki Bar. The townhouse is close to Laurel Rd and Sarasota Memorial Hospital. Property is managed by owner. Timely response to accommodate your needs. Summary of amenities: PARKING: 2-CAR TANDEM GARAGE HOA PRIVATE COMMUNITY 1 BLOCK FROM INTERCOASTAL SCREENED BALCONY CEILING FANS VAULTED CEILING CENTRAL AIR UPGRADED TALL CABINETS GRANITE COUNTERTOP STAINLESS STEEL APPLIANCES CONVECTION RANGE/OVEN/AIRFRYER MICROWAVE DISHWASHER IN-SINK DISPOSAL SMART REFRIGERATOR DINING ROOM & FAMILY ROOM MASTER BEDROOM WITH WALK-IN CLOSET MASTER BATH GUEST BEDROOM ADDITIONAL STORAGE IN LOWER FLOOR OR GARAGE AIR CONDITIONING WASHER/DRYER SPRINKLER SYSTEM COMMUNITY SWIMMING POOL WITH LOUNGE CHAIRS + USE OF CASEY KEY MAINLAND POOL WALK/BIKE TO TOP RATED PINEVIEW SCHOOL, WALLMART, POST OFFICE, LEGACY BIKE TRAIL CLOSE TO SIESTA KEY, NOKOMIS BEACH, VENICE BEACH, OSCAR SCHERER STATE PARK HUGE FURNISHED BONUS ROOM ON FIRST FLOOR OUTDOOR GRILL Turn-key ready!

1811 Highland Road, Osprey

3976 Destination Drive Unit 102, Osprey
$409,000
Phase 2 Of Bay Street SubDv. ⋅ 34229 Zip Code
ANOTHER REDUCTION! Seller is ready to make a deal! EXCEPTIONAL OPPORTUNITY to OWN & GROW YOUR BUSINESS in OSPREY'S MARGARITTVILLE DEVELOPMENT DISCTRICT! An UP-SCALE WATERFRONT WALKING COMMUNITY POISED TO BE A MAJOR DESTINATION IN SOUTH SARASOTA COUNTY! First-floor retail-office condominium in the highly regarded Bay Street Commercial Condominium, located in Osprey’s Bayfront Village—one of Sarasota County’s fastest-growing waterfront walking communities. This turn-key, beautifully built-out space is designed to accommodate a wide range of professional uses, including medical, professional services, retail, and boutique office operations. Perfectly positioned for long-term success, the property is set to benefit from significant foot traffic, with approximately 252 luxury multifamily apartment residences currently developed directly behind the town center. The location is further enhanced by close proximity to affluent communities such as The Oaks and nearby luxury bayfront estates, all just minutes away. Inside, the meticulously designed layout features soaring ceilings that create a refined sense of openness and sophistication. No expense was spared in the high-end build-out, with substantial investment dedicated to crafting a luxurious, private, and highly functional professional environment. The thoughtfully designed floor plan includes six private offices, two conference rooms, a bright, professionally appointed lobby with a welcoming reception area, two well-appointed bathrooms, and a convenient kitchenette. Each office is constructed with soundproofed walls and solid hardwood doors, ensuring privacy, comfort, and quiet productivity. Upscale lighting, premium flooring, and modern finishes elevate the space throughout, reinforcing its contemporary, high-end appeal. A rear door provides direct access to ample employee parking, offering convenience and ease for staff. The property also features a charming front porch that may serve as a welcoming seating area with potted plants, a coffee table, and comfortable seating, creating a warm and inviting, home-like first impression for clients, patients, or guests. Ideal for medical, professional, or boutique office use, this property presents a rare opportunity to establish or expand your business within a high-end commercial complex poised for continued growth and long-term value. See attached Feature Lists for additional details about the community and Unit 201.

3976 Destination Drive Unit 102, Osprey

7204 Jessie Harbor Drive Unit 7204, Osprey
$395,000
2 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code
**BEAUTIFULLY UPDATED WATERFRONT CONDO WEST OF THE TRAIL! BRING YOUR BOAT & KAYAK FOR DIRECT ACCESS TO THE INTRACOASTAL WATERWAY AND GULF OF MEXICO.** Unlike many Blackburn Harbor residences, this thoughtfully renovated 2-bedroom, 2-bath, second-floor condo is move-in ready, allowing the next owner to immediately enjoy the coveted waterfront lifestyle without the time or expense of major updates. The fully renovated interior showcases an impressive kitchen with quartz countertops, solid wood cabinetry, stainless steel appliances, and CoreTec luxury vinyl flooring throughout (except the guest bedroom). The spacious owner's suite features custom built-in closets and cabinetry, complemented by an elegantly updated en-suite bath. Multiple sliding glass doors open to an expansive screened balcony, where peaceful Florida nature views create the perfect setting to relax and unwind. Located within the secure, gated community of Blackburn Harbor, residents enjoy an exceptional waterfront lifestyle with boat docks (subject to availability), kayak launch and storage, direct Intracoastal access, a community pool, tennis and pickleball courts, fitness center, clubhouse, gazebo with BBQ area, and abundant natural surroundings. Private covered parking and ground-level storage are also included. Ideally situated in Osprey between Sarasota and Venice, Blackburn Harbor is just minutes from nationally ranked Pine View School, the Legacy Trail, Gulf beaches, shopping, dining, and everything the Gulf Coast lifestyle has to offer. RECENT COMMUNITY IMPROVEMENTS INCLUDE: Asphalt paving, irrigation, walkways, walkway lighting, and upgraded lighting for the tennis and pickleball courts.

7204 Jessie Harbor Drive Unit 7204, Osprey

436 S Tamiami Trail Unit C4, Osprey
$350,000
Osprey Executive Park SubDv. ⋅ 34229 Zip Code
Open to discussing concessions with reasonable terms. Office condo located in Osprey, FL, directly on U.S. Route 41 (Tamiami Trail), positioned between Sarasota and Venice. The location provides straightforward access to major roadways, regional airports, and surrounding commercial centers, supporting day-to-day operations and client accessibility. Osprey is part of Sarasota County, an area with consistent business activity and continued growth across professional services, healthcare, and small business sectors. The setting offers a balance of accessibility and a quieter environment compared to higher-density markets. Key Features Reception / waiting area Multiple cubicle workspaces Two private offices Conference room suitable for team or client meetings Kitchenette / break area In-suite restroom Ample on-site parking Quarterly HOA dues: $1215. This space is well-suited for businesses seeking a functional layout in a central Gulf Coast location with strong regional access.

436 S Tamiami Trail Unit C4, Osprey

1819 Highland Road, Osprey
$319,000
2 Beds ⋅ 3 Baths ⋅ Towns-End Shores SubDv. ⋅ 34229 Zip Code
This beautifully appointed 2-bedroom, 2-bath townhome offers a wonderful blend of comfort, privacy, and Florida living in "The Osprey", a community of just 12 residences. The open-concept floor plan features high ceilings, generous living spaces, and large windows that fill the home with an abundance of natural light. The spacious owner’s retreat provides a peaceful setting for relaxation, while the second bedroom offers flexibility for guests, an office, or additional living space. Located in flood zone X, the oversized garage offers the perfect opportunity to add to your living space or provides an abundance of storage. The private outdoor spaces are a true highlight of the home. The beautifully landscaped yard and garden create a peaceful retreat, while the private terrace provides an ideal setting for al fresco dining and entertaining. A mature specimen lemon tree serves as the star of the garden, providing fresh lemons for lemonade, cooking, or homemade limoncello. Residents also enjoy access to the community pool, adding to the relaxed, resort-like feel of the property. The location is equally appealing. Situated in Osprey, the property is conveniently located near the beaches of Casey Key, local shops, restaurants, and a variety of recreational amenities directly across the street from Oscar Scherer State Park, home to over 17 miles of trails and nearly 1400 acres of natural habitats, launch a kayak, or simply take in the peaceful surroundings along the water. The nearby Casey Key Resort offers the opportunity to enjoy its pool, facilities, and restaurant for the day, providing an additional resort-style experience close to home. Downtown Sarasota and downtown Venice are also easily accessible, offering an outstanding selection of dining, shopping, cultural attractions, and entertainment. With its private outdoor spaces, community pool, beautiful natural light, and convenient location, this exceptional townhome offers a refined yet relaxed approach to coastal Florida living. Whether enjoyed as a full-time residence or a seasonal retreat, this home offers an exceptional opportunity to embrace the Florida lifestyle.

1819 Highland Road, Osprey