Location: Osprey
Do Not Show Listings
172 SEA ANCHOR DR, OSPREY, FL 34229
$895,000157 Days on yellowkey MLS ID: A4671745
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2283 Built: 1977Monthly Fee: $204 Tax: $8,870 (2024)Community: Southbay Yacht & Racquet ClubSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,870
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2024
Middle School: Laurel Nokomis Middle
Remarks: Amazing home with many improvements ideally located in a sought-after marina community. This beautifully updated 3-bedroom 3 bath residence has been thoughtfully enhanced for comfort, style and easy living. It's tucked inside a lively marina community where every day feels like vacation. This home features modern updates throughout. Newly remodeled kitchen, new master bath, luxury vinyl flooring, saltwater pool and newer cage, den, in home gym, new tile roof, new AC, hurricane impact windows and doors as well as an easy low maintenance open floorplan. Enjoy boating, fishing, biking, pickleball, tennis, bocci ball, kayak storage, jet ski pads and boat slips. Spend evenings sitting by the community pool looking out over the marina watching amazing sunsets. Walk, bike our take a golf cart to nearby shopping, restaurants and tiki bars. A definite value in an amazing community!
Listing is courtesy of: GOLF & BAY PROPERTIES LLC (941-539-8400)
Listing Agent: Sharon Lewis (941-966-5400)
1337 COPPERWOOD DR, OSPREY, FL 34229
$550,000200 Days on yellowkey MLS ID: A4666722
REDUCED by $19,000 (3.3%) on 04/02/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2172 Built: 2004Monthly Fee: $397 Tax: $4,420 (2025)Community: Willowbend Phase 3Spa: NoSingle Family
Taxes:$4,420
Tax Year: 2025
Remarks: This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings, architectural details like arches and insets, sconce lighting, crown molding, tray ceilings and shutters. The layout promotes a refined atmosphere where the subtle color palette, which is newly painted, fosters a seamless transition between indoor and outdoor spaces, ideal for enjoying Florida's unique climate. Stylish den at front of the home while the living and dining areas flow into a spacious family room adjacent to the open kitchen. The kitchen is functional and stylish, equipped with solid wood cabinets, granite, ample storage options and a breakfast room with tranquil pool views. Natural gas cooking for the chef of the residence. A practical entry from the garage leads to a large laundry room that includes additional storage. The owner’s suite is a retreat, featuring dual closets, a separate linen closet, a luxurious walk-in shower, glass brick accents, dual sinks with separate vanities and a relaxing soaker tub. Convenient direct pool access as well. Guests will appreciate the two-bedroom suite with its dedicated hallway and bath, which allows for privacy from the owner’s suite. The community boasts low fees that cover ground maintenance, irrigation, access to the pool and spa, gym facilities, pickleball courts, and high-speed internet and DirecTV streaming. Families will benefit from the nearby top-rated Pine View School, while the Intracoastal Waterway, beautiful beaches, Legacy Trail, shopping, dining, grocery stores, coffee shops and vibrant tiki bars are all just minutes away. New water heater in 2025, Interior freshly painted in 2025, storm shutters on lanai in 2020 and accordion storm shutter on front door.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Todd Currey (941-402-6000)
14041 BELLAGIO WAY #214, OSPREY, FL 34229
$700,0004 Days on yellowkey MLS ID: A4689731
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1799 Built: 2006Monthly Fee: $1,248 Tax: $6,254 (2025)Community: Villas At Bellagio Harbor VillageSpa: NoCondo
Taxes:$6,254
Elementary School: None
High School: None
Middle School: None
Remarks: Waterfront Sanctuary-Boater's Paradise at the Osprey Harbor Village- 3 Bedrooms | 2 Bathrooms | Direct Intracoastal Frontage Rare opportunity for direct Intracoastal living at Villas at Osprey Harbor Village (formerly Bellagio Harbor Village). This 3 bedroom, 2 bath residence offers approximately 1,862 sq. ft. of light filled living space with views of the canal, Little Sarasota Bay and Intracoastal Waterway. The open concept design features 9’5” tray ceilings, impact windows and doors, and solid wood cabinetry, granite countertops, kitchen island, and kitchen island bar—ideal for entertaining, anchored by a neutral, airy palette with timeless finishes. The split bedroom layout provides privacy, with a spacious primary suite featuring a spa style bath, separate tub and shower, and direct access to an oversized 270 sq. ft. waterfront balcony from the bedroom. Each window is a curated lens, framing the hues of the Bay and the sculptural silhouettes of architectural lines of Mediterranean inspired Villas. Days here are defined by the rhythmic play of light reflecting across the water and the silent flight of ospreys, eagles, and pelicans—a true haven for the bird watcher seeking a quiet refuge. Whether you are hosting a sunset gathering on your private balcony or entertaining your guests at the community terrace, the club room or embarking on a day of boat excursion to the newly opened Midnight Pass, the lifestyle here is one of effortless coastal elegance. Community amenities include a deep water harbor marina with wet and dry slips, resort pool, clubhouse, fitness center, hot tubs, kayak storage, and launch. Centrally located between Sarasota and Venice, and minutes from Venice, Nokomis, Siesta Key, and Casey Key, Oscar Scherer State Park, Spanish Point, Legacy Trail, and cultural and retail amenities of Sarasota. With new metal roof, exterior and interior paint completed in 2025, this property stands as a resilient sanctuary of enduring value. For the resident who values privacy, prestige, and the restorative power of nature, this is the definitive Osprey address. Schedule your private tour today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Veronica Lee (609-651-0305)
4271 EXPEDITION WAY #103, OSPREY, FL 34229
$290,0008 Days on yellowkey MLS ID: A4689541
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1135 Built: 2017 Tax: $3,507 (2025)Community: Bay Street VillageCondo
Taxes:$3,507
Remarks: One or more photo(s) has been virtually staged. Live where everyday life feels simple, connected, and close to everything you love. Located in the gated community of Bay Street Village in Osprey, this beautifully maintained second-floor condo offers the perfect blend of comfort, convenience, and a relaxed Florida lifestyle. Just minutes from Nokomis Beach, Siesta Key, the Legacy Trail, Oscar Scherer State Park, and an abundance of shopping and dining options, everything you need is right at your fingertips. This 2-bedroom, 2-bathroom condo welcomes you with a private entry and interior stairway leading to a bright and open main living space. Positioned on the second floor, the home enjoys added privacy along with elevated views and an abundance of natural light. The layout lives effortlessly, with high ceilings and neutral finishes creating an inviting and airy feel throughout. An attached garage with direct interior access adds everyday ease and practicality. The kitchen is both functional and stylish, featuring granite countertops, stainless steel appliances, a large island with seating, and a walk-in pantry. It opens seamlessly to the dining and living areas, making it easy to host, relax, or simply enjoy day-to-day living without feeling closed off. The spacious primary suite offers a comfortable retreat with a large walk-in closet and an en-suite bathroom complete with dual sinks and a walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Enjoy your morning coffee or unwind in the evening on the screened lanai, where you can take in the Florida breeze and peaceful surroundings from your elevated position. Whether you're heading out to the beach, meeting friends for dinner, or enjoying the nearby parks and trails, this location makes it all feel effortless. Bay Street Village enhances the lifestyle even further with resort-style amenities including a community pool, fitness center, scenic ponds, and beautifully landscaped grounds, all within a gated and well-maintained setting. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
313 LOOKOUT POINT DR, OSPREY, FL 34229
$5,999,99911 Days on yellowkey MLS ID: A4688995
Bed: 4 Bath: 4.5 Gar: 5 Liv Area Sq Ft: 5337 Built: 2016Monthly Fee: $219 Tax: $20,559 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$20,559
Remarks: Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Club—one of Sarasota’s most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up to 55 feet, and direct access to the Intracoastal Waterway and Gulf of Mexico, this is a setting designed for those who expect seamless access to life on the water. Privately situated on a homesite surrounded by water on two sides, the property offers a rare level of exposure and presence. From your outdoor living spaces, the backdrop is ever-changing—boats moving through the marina, dolphins just beyond your dock, and unobstructed sunsets that define the end of each day. Inside, the residence is a study in craftsmanship and comfort, where rich wood detailing carries throughout—from the staircase to the ceilings in the main living areas and extending into the outdoor spaces—creating a warm, architectural continuity rarely seen. Walls of impact-rated windows and doors bring in natural light while offering peace of mind, while expansive sliders pocket away completely—creating a perfect expression of Florida living with seamless indoor-outdoor flow and unobstructed sunset views across the bay. The kitchen is both striking and highly functional, appointed with Wolf and Miele appliances, dual Sub-Zero refrigerators, a warming drawer, two sinks, and a concealed pantry, all complemented by generous storage and oversized closets throughout the home. A fireplace anchors the main living space, adding warmth and ambiance. Designed for real life as beautifully as it is for entertaining, the home also features a thoughtfully designed mudroom off the garage entry, creating an organized and functional transition into the home. Outdoor living is equally elevated and designed for year-round enjoyment. Electronic roll-down screens allow you to fully enjoy the outdoor kitchen, complete with a propane grill and hood, sink, and composite cabinetry. Just beyond, a propane-fed fire pit creates the perfect setting for evenings by the pool. The separate air-conditioned poolside cabana offers stunning bayfront views and is equipped with its own refrigerator and ice maker—ideal for entertaining or creating a private retreat for guests. The floor plan is thoughtfully designed, offering 4 bedrooms, 4.5 baths, a private office, upstairs lounge, and expansive laundry room—balancing everyday livability with elevated design. For collectors and enthusiasts, the 5-car garage with 9,000 lb lift provides exceptional capacity, while the 110-foot private dock with jet ski lift delivers a level of waterfront utility that is increasingly rare. Southbay Yacht & Racquet Club offers a curated lifestyle with a private marina, clubhouse, fitness center, heated pool, tennis and pickleball courts, and walking trails—all within minutes of Casey Key, where pristine beaches, waterfront dining, and relaxed coastal elegance define the surrounding area. This is a property that stands apart. Compare it to anything else on the market and the value is clear. Priced to sell, with a motivated seller.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Natalie Gutwein (941-993-2660)
5100 JESSIE HARBOR DR #403, OSPREY, FL 34229
$679,900108 Days on yellowkey MLS ID: A4676382
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2143 Built: 2004Monthly Fee: $1,027 Tax: $5,647 (2025)Community: Blackburn Harbor ResidencesCondo
Taxes:$5,647
Remarks: This meticulously maintained, waterfront residence is in an amenity-rich, gated community. Offering over 2,000 square feet of casual luxury, the well-designed living space includes two bedrooms, two baths and features a welcoming foyer, a breakfast area, and a separate room ideal for a den or home office. The upgraded appointments throughout are numerous and include top-of-the-line KitchenAid appliances, custom cabinet pullouts and the kitchen’s showstopper is the exquisite stone counter surfaces, which wow and make everyday cooking, or your gourmet meal preparation, a joy. Plantation shutters and remote-controlled blinds grace many of the windows. The views from your primary retreat vie for your attention thanks to the shimmering intracoastal front and center. Generous in size, the main retreat delights with a walk-in shower, large soaking tub, double vanities, a separate makeup area, private water closet and dual walk-in closets. The second bath features a recently installed walk-in tub, designed for enhanced comfort, ease and safety. Enjoy expansive water views from your fourth-floor balcony, where nesting birds, jumping fish and dazzling sunsets create a stunning backdrop for your daily pleasure. The inside laundry room and your two assigned parking spaces are under the building and out of the elements, adding to the opportunity. The lifestyle amenities in this friendly community include recently resurfaced tennis and pickleball courts, a heated swimming pool, a clubhouse with fitness area, kayak storage and launch, and fishing. Boat slips are available on a first-come basis for an additional fee. Enjoy a waterfront picnic under the gazebo, complete with grills, a walking path and pretty greenspace areas. Ideally close to shopping, dining, the crystal sand beaches and famed Oscar Scherer State Park, which offers biking, birdwatching, geocaching and over 15 miles of scenic hiking trails, and a natural lake for swimming, and the best part is the proximity, just across the street. Come be enchanted, as this slice of Florida paradise is one you won’t want to miss.
Listing Agent: Cindy Migone (941-812-7438)
583 PINE RANCH EAST RD, OSPREY, FL 34229
$569,000166 Days on yellowkey MLS ID: A4670669
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2203 Built: 1996Monthly Fee: $23 Tax: $4,537 (2024)Community: Bay Oaks EstatesSpa: YesSingle Family
Taxes:$4,537
Remarks: Beautifully updated 4BR/2BA pool home in the sought-after Bay Oaks Estates community of Osprey. This single-story residence's backyard borders the Legacy Trail and includes a private gate for direct trail access. Inside, high ceilings and natural light complement luxury vinyl plank flooring, fresh paint, new doors, baseboards, and fixtures. The kitchen features quartz countertops, marble backsplash, recessed lighting, an undermount sink, and newer Whirlpool appliances. A split floor plan provides privacy with spacious bedrooms, including a primary suite with lanai access, two closets (one walk-in), and a spa-like bath with soaking tub, walk-in shower, and dual quartz vanities. The screened lanai overlooks an inviting pool and spa with a private, tree-lined backdrop. Other highlights include a dedicated laundry room, 2-car garage with new door and opener, newer roof, A/C, and water heater. All improvements and system updates completed in 2020. Last year, the pool was resurfaced and the waterline tile replaced. Additional upgrades include new pool equipment, a saltwater system, and a heater. Low HOA and no CDD. Conveniently located near top-rated schools, Oscar Scherer State Park, shopping, dining, and world-class beaches including Siesta Key, Nokomis, and Venice.
Listing is courtesy of: GALLERY PROPERTIES INTERNATION (941-957-0833)
Listing Agent: William Fortner (941-915-4045)
745 FORDINGBRIDGE WAY, OSPREY, FL 34229
$640,00040 Days on yellowkey MLS ID: N6143319
REDUCED by $10,000 (1.5%) on 04/17/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1893 Built: 2002Monthly Fee: $120 Tax: $4,308 (2025)Community: Rivendell WoodlandsSpa: NoSingle Family
Taxes:$4,308
Middle School: Sarasota Middle
Remarks: Welcome to this beautiful home in the sought-after Rivendell community. The curb appeal is evident as you drive up to this home, from the landscape and the paver driveway to the beautiful front door. As you step inside the wide foyer, your view extends out through the sliders leading out to the pool and lanai. This well-maintained updated residence combines a bright, inviting interior designed for everyday living and entertaining. Neutral colored tiles extend throughout the kitchen, breakfast nook, dining and living areas. The kitchen is to the left of the dining and living area and offers generous counter space for all your preparation and cooking needs. The primary bedroom suite is spacious with sliders to the lanai and a large walk-in closet with a deluxe custom organizer. The ensuite bathroom has both a tub and a walk-in shower with a long vanity with two sinks and a makeup area in the middle. The remaining bedrooms and bathroom are on the other side of the house offering privacy for daily life or entertaining. Enjoy outdoor living at its finest with your private, heated pool and a backyard that offers desirable privacy — perfect for relaxing or hosting guests year-round. Recent major upgrades provide peace of mind, including a new Novatik metal roof (2025) along with new fascia, soffits, and gutters. The home also features an updated HVAC system (2023) and impact windows and doors everywhere with a motorized Kevlar hurricane shutter for the lanai. Rivendell is a beautiful 400-acre community with parks, trails, and a community pool located in Osprey. It is in close proximity to Pine View School. It is between charming Venice and vibrant Sarasota, so you'll enjoy a rich array of shopping, dining, and cultural experiences. Within a few miles, you can be at the world-famous Siesta Key Beach to swim or relax on the beach. Or head south a few miles to the more secluded Nokomis Beach and North Jetty Beach. This location truly offers easy access to the best of coastal living. For outdoor enthusiasts, Legacy Trail Osprey Junction Trailhead is nearby as is Oscar Scherer State Park. Explore the natural beauty of the region at your own pace while biking or walking, taking in the lush scenery and tranquil surroundings. Don’t miss the opportunity to own this thoughtfully upgraded home in one of Osprey’s most popular communities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-485-5421)
Listing Agent: Janet Oberholtzer (484-798-7824)
759 FORDINGBRIDGE WAY, OSPREY, FL 34229
$727,0001 Day on yellowkey MLS ID: O6399774
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2950 Built: 2002Monthly Fee: $55 Tax: $7,129 (2025)Community: Rivendell WoodlandsSingle Family
Taxes:$7,129
Remarks: Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layout, this residence boasts elegant finishes and ample natural light throughout. The modern kitchen is equipped with top-of-the-line appliances and give plenty of storage space. Enjoy the serene outdoor area with a beautifully landscaped yard, appropriate for relaxation and entertainment. Situated in a desirable neighborhood, this property provides easy access to Pineview Gifted School. Don't miss this exceptional opportunity to own this beautiful marvelous 4 bedrooms with a dent and 3 and 1/2 baths opportunity. The circle pool is beautiful and you can see it in Dinnig Room. The master bedroom is spacious with the beautiful marble Venetian team. There are 2 medium room next door. The washer and dryer are new in the laundry room. All the bathrooms are newly installed marble and high luxury tiles. The floor is beautiful with fancy travertine tiles for the whole downstairs floor and the upstairs are high end luxury plank vinyl all new floors and bathrooms
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
402 MACEWEN DR, OSPREY, FL 34229
$1,750,0004 Days on yellowkey MLS ID: A4690018
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3565 Built: 1999Monthly Fee: $142 Tax: $13,762 (2025)Community: OaksSingle Family
Taxes:$13,762
Remarks: Tucked behind the private gates of The Oaks Club side, in one of Sarasota’s most prestigious and sought-after country club enclaves, this exquisite residence captures the essence of refined Florida living. Ideally situated just moments from the clubhouse and overlooking the manicured fairways of the Eagle Course, the home offers a rare blend of privacy, scale, and serene golf course vistas that stretch endlessly from the expansive screened lanai. Spanning over 3,500 square feet, this beautifully appointed single level home features three generously sized bedrooms, a dedicated office, and three-and-a-half baths, all thoughtfully designed to balance sophistication with everyday comfort. From the moment you enter, a sense of understated elegance unfolds—gracious formal living spaces anchored by a statement fireplace, soaring tray ceilings, intricate crown molding, and an abundance of natural light that enhances every architectural detail. The primary suite serves as a true retreat, offering impressive proportions, a substantial walk-in closet, and a spa-inspired bath designed for relaxation. Additional living spaces flow effortlessly, including a well-equipped laundry room with custom built-in workspace, ideal for modern living. Every inch of the home reflects careful attention to detail, from the finishes to the functional layout. Outdoors, the residence truly shines. The screened lanai becomes a private sanctuary, complete with a sparkling pool and spa, perfectly positioned to capture sweeping views of the 4th hole. Whether entertaining guests or enjoying quiet evenings, this space delivers an elevated indoor-outdoor lifestyle synonymous with luxury coastal living. Enhancing both comfort and peace of mind, the home is equipped with a whole-house generator, and Security Camera's outside and the oversized three-car side entrance garage and circular paver driveway provide both convenience and impressive curb appeal. Quick notes to take away: Roof - 2023 / A/C (both units) - 2024 Ownership within The Oaks grants access to an unparalleled private club experience. Residents enjoy two championship 18-hole golf courses, impeccably maintained HAR-TRU tennis courts, newly introduced pickleball facilities, and a state-of-the-art Wellness and Fitness Center exceeding 7,500 square feet. Complemented by an exceptional culinary program and a vibrant calendar of curated social events, The Oaks offers a lifestyle defined by elegance, activity, and connection. Club membership is required, within this distinguished Sarasota community.
Listing Agent: Steven Kepecz, Pa (941-376-6411)
4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229
$329,90043 Days on yellowkey MLS ID: N6143250
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1528 Built: 2018 Tax: $3,781 (2025)Community: Bay Street VillageCondo
Taxes:$3,781
Remarks: 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.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Tim Weller (941-221-0155)
32 SIESTA CIR W, OSPREY, FL 34229
$69,0004 Days on yellowkey MLS ID: A4690063
0 Days Off yellowkey (back on 4/16/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 480 Built: 1968Monthly Fee: $215 Tax: $555 (2025)Community: ArborsMobile Home
Taxes:$555
Remarks: Charming and affordable 1-bedroom, 1-bath mobile home in desirable Osprey, FL! Situated on a spacious corner lot, this cozy residence offers great potential with a price that reflects the opportunity to update and make it your own. The open living room flows seamlessly into the kitchen, with space for a small dining table—perfect for casual living. The primary bedroom features a convenient built-in desk or makeup area, adding both function and charm. Durable metal siding and roofing provide peace of mind, while the extra-wide carport offers ample covered parking, complemented by additional public parking along the side lot. Enjoy Florida living outdoors with tropical palm trees welcoming you home, a large screened lanai for relaxing or entertaining, and a handy storage shed. Washer and dryer are included for added convenience. A great opportunity to own in a prime location with plenty of potential—don’t miss it! Located in the desirable Arbors community in Osprey, this home is part of an active, friendly neighborhood featuring a clubhouse, swimming pool, shuffleboard courts, outdoor fitness area and a full calendar of social activities. Ideally situated between Sarasota and Venice, you’ll have easy access to boutique stye shopping, multiple dining options, theaters, performing arts venues, and stunning Gulf beaches. Everything you love about the Florida lifestyle just minutes away. This is relaxed, low-maintenance living in a welcoming community.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Karen Geiger (941-928-8889)
522 LUMINARY BLVD, OSPREY, FL 34229
$647,00071 Days on yellowkey MLS ID: A4676528
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2320 Built: 2005Monthly Fee: $420 Tax: $4,456 (2025)Community: Willowbend Ph 3Spa: NoSingle Family
Taxes:$4,456
Remarks: This exquisite three-bedroom, three-bath-plus-den, Lee Wetherington built home exemplifies intelligent design and beauty in the community of Willowbend. This Ashley floor plan is thoughtfully oriented to the south, allowing for abundant natural light and stunning lakefront views. The residence features inviting curb appeal with a paver-accented driveway and walkway, leading to an impressive custom double-door entry. Inside, high-end upgrades and recent enhancements contribute to the home's timeless character. The sophisticated interior showcases clean lines, intricate tray ceilings and tile flooring throughout main living areas. Crown molding and impressive lighting fixtures add elegance to the space. The gourmet kitchen is a chef's dream, featuring solid wood cabinetry, Corian countertops and new stainless appliances in January 2026 with gas cooking. Even the laundry room is aesthetically pleasing. The split floor plan affords two guest bedrooms conveniently behind a pocket door, sharing a bath, providing privacy to family and guests alike. The den/study includes a built-in office with a sizeable desk overlooking the lake. The family room boasts a wall of sliding glass doors with an adjacent corner pocket slider that opens wide, seamlessly transitioning to the tranquil outdoor living space. The extended lanai features two covered areas, ideal for relaxation, while the custom pond with waterfall add to the ambience and enjoyment of the tropical surroundings. Water views from most rooms in the home! A well-appointed dinette offers picturesque views of the waterfall and lake through a large aquarium window as well. The luxurious owner’s suite includes dual walk-in closets, dual sinks, a walk-in shower and a tub for ultimate comfort. The home is equipped with high-speed internet and streaming television, with yard maintenance and access to community amenities such as a pool, spa, fitness center, pickleball court and playground all included in the low HOA fees. Convenient to beautiful gulf beaches, Oscar Scherer State Park, Legacy Trail, Pine View School and waterfront dining, this residence offers an unparalleled lifestyle.
353 S SHORE DR, OSPREY, FL 34229
$1,200,00017 Days on yellowkey MLS ID: A4688006
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 1968Monthly Fee: $10 Tax: $3,904 (2025)Community: Sorrento Shores Rep Of 2Spa: NoSingle Family
Taxes:$3,904
Remarks: Welcome to Sorrento Shores—where location, lifestyle, and waterfront living come together beautifully. Perfectly positioned on a generous .36-acre canal-front lot, this 3-bedroom, 2-bath pool home offers direct access to the Intracoastal Waterway just a few homes down the canal. A true boater’s dream, your private dock provides quick and easy access to some of the area’s most beloved waterfront destinations. Cruise north to Casey Key Fish House, or the newly reopened Midnight Pass. You could also head south toward Venice to enjoy Pop's Sunset Grill and Pelican Alley. Spend your days at Snake Island, or venture through the jetties to the open waters of the Gulf of Mexico —where the possibilities for exploration are endless. Inside, the home features a spacious and flexible floorplan with a kitchen, dining room, living room, and den, along with an indoor laundry room. Two of the three bedrooms are private ensuites, offering ideal comfort for guests or multi-generational living. The home is being offered turnkey (with select personal exclusions), making it move-in ready for immediate enjoyment or seasonal use. Step outside to your impressive 27x40 enclosed lanai with pool, creating an expansive outdoor living space perfect for entertaining or unwinding in your own private tropical setting. In addition to the 2-car garage, a large storage shed provides added convenience, and there is dedicated space to park your boat trailer right on the property—no off-site storage needed. Major updates provide peace of mind: New roof -July2025, 3rd nail installed in rafters-July 2025, Pool Heater (Electric)-December 2025, New Pool Cage (Picture frame)- January 2025, Primary bath remodeled- August 2025, Guest Bath (partial remodel)-August 2025, Interior painted-September 2025, Popcorn ceiling removed and ceiling painted-August 2025. New Septic System-2024 Sewer pipes lined-2023/2024 New water heater-2024 A/C (2018) Sorrento Shores is a hidden gem offering a voluntary HOA of just $125/year and no CDD fees, delivering a relaxed coastal lifestyle without the burden of high community costs. Whether you’re searching for a winter retreat, full-time residence, or investment opportunity, this property stands out with its rare combination of quick Intracoastal access, expansive lot size, private dock, and prime location.
Listing Agent: Phyllis Coviello (941-408-3265)
4284 EXPEDITION WAY #NA, OSPREY, FL 34229
$339,90064 Days on yellowkey MLS ID: A4681835
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1430 Built: 2017 Tax: $2,934 (2025)Community: Bay Street VillageCondo
Taxes:$2,934
Remarks: Welcome to Bay Street Village, a gated, maintenance-free community in Osprey between Sarasota and Venice. The tile roofs and paver driveway provide Florida charm. This move-in-ready 3-bed, 2-bath condo features an open layout, IMPACT glass, and a private screened balcony with a pond view. The kitchen offers a large granite counter with seating and a newer refrigerator. The primary suite includes a walk-in closet and an en-suite bath with dual sinks and a step-in shower. A split floorplan adds privacy, and the attached one-car garage provides extra storage. Community amenities include a heated pool, fitness center, and clubhouse. Bay Street Park is directly across the street and is walkable—includes a dog park for your furry friend. Water is included in the monthly fee. Conveniently located near Nokomis Beach, Oscar Scherer State Park, The Legacy Trail, Publix, restaurants, shopping, and both US-41 and I-75, this condo offers easy, low-maintenance Florida living in a central coastal location in a very nice community.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Grace Bonaccorso (941-580-1362)
244 WOODLAND DR #244, OSPREY, FL 34229
$200,000184 Days on yellowkey MLS ID: A4667419
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1980 Tax: $2,685 (2025)Community: Pine Run IiiCondo
Taxes:$2,685
Remarks: Turnkey-Furnished & Best Value in Pine Run Now Offered at $200,000 (Recently Reduced $25,000). Move right in and start enjoying the Florida lifestyle with this beautifully updated 2-bedroom, 2-bath condo offering 1,325 square feet of bright, open living. Featuring vaulted ceilings and an airy layout, this residence feels spacious and inviting from the moment you walk in. The kitchen showcases stainless steel appliances, a sleek glass backsplash, and a sunlit breakfast nook perfect for everyday living or entertaining. The primary suite offers direct access to the screened lanai, creating a seamless indoor-outdoor flow with peaceful views of lush, private greenery. Being sold turnkey-furnished, this is a true move-in-ready opportunity just bring your suitcase. Located in the highly sought-after Pine Run community, residents enjoy resort-style amenities including two heated pools, tennis and pickleball courts, a fitness center, clubhouse, and over 20 acres of scenic walking trails. All just minutes from Nokomis Beach, Casey Key, dining, and shopping. Low-maintenance, turnkey living at an unbeatable price, ideal for full-time, seasonal, or investment use.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
250 HIDDEN BAY DR #301, OSPREY, FL 34229
$725,00086 Days on yellowkey MLS ID: A4679278
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2168 Built: 2017 Tax: $7,792 (2025)Community: Edgewater At Hidden BaySpa: YesCondo
Taxes:$7,792
Remarks: Enjoy sweeping water views and stunning sunsets over Little Sarasota Bay from this spacious third-floor corner residence in the gated waterfront community of Edgewater at Hidden Bay. Built in 2017 and moved into in Jan 2018, this three-bedroom plus den, 2.5-bath condominium offers nearly 2,200 square feet of living space with easy elevator access and one assigned parking space in the building. The attractive open floor plan features soaring ceilings, impact-rated windows and sliding doors, easy maintenance tile plank flooring and abundant natural light throughout. The kitchen includes granite countertops, solid wood cabinetry, stainless steel appliances and custom storage with pullout drawers. The living area offers a built-in dry bar with wine refrigerator and opens to a large, screened-in terrace with privacy-screens and expansive bay views. The primary suite includes dual walk-in closets and a luxurious bath with dual quartz vanities, decorative tile flooring, makeup vanity and walk-in shower. Additional features include a private den/office, in-unit laundry room, two full baths and a powder room, AC from 2023. Edgewater at Hidden Bay is a gated, resort-style community set on 14 acres along Little Sarasota Bay and the Intracoastal Waterway, directly across from Casey Key. Community amenities include a waterfront clubhouse with kitchen and quartz bar, heated pool and spa, fitness center, library, tiki hut with grilling stations, pickleball and tennis courts, kayak launch, fishing pier, dog play area, and an elevated boardwalk through mangroves and palm-lined grounds. Hidden Bay is conveniently in Osprey just south of Sarasota, near area beaches, shopping and dining, and only minutes from Venice.
Listing Agent: Per Nordstrom, Pa (941-228-1080)
447 N SHORE DR, OSPREY, FL 34229
$515,35044 Days on yellowkey MLS ID: A4684009
REDUCED by $19,550 (3.7%) on 04/02/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1874 Built: 1964 Tax: $4,243 (2025)Community: Sorrento ShoresSingle Family
Taxes:$4,243
Remarks: Classic and cool, this Sorrento Shores beauty blends true Old Florida charm with all the modern updates you actually want, perfectly positioned West of the Trail near the sparkling Intracoastal Waterway. What’s been at the top of your list — move-in ready, a spacious lot, no flood zone, boat/RV parking, optional low HOA, no CDD fees, community marina access, an A+ school district, or quick access to beaches and dining? The good news? You don’t have to choose. This home truly checks every box. Inside and out, everything has been thoughtfully renovated since 2022, including a new roof (2023 w 25yr warranty), septic, central air, impact windows and doors (with the exception of the Florida room), updated electrical panel, irrigation equipment, soffits, water heater, impact garage door, pavers, and beautifully redesigned kitchen and baths. Luxury vinyl plank flooring runs throughout, complemented by fresh paint and abundant natural light. The split floor plan provides privacy, while the open living spaces make everyday living and entertaining effortless. The kitchen is both functional and inviting, featuring shaker cabinetry, quartzite countertops, stainless steel appliances, a generous island, and a charming coffee bar that flows seamlessly into the family room and dinette. One of the standout features is the 336-square-foot air-conditioned sunroom with pocket sliders — incredible flex space for a home office, gym, playroom, or second living area — all overlooking the expansive backyard. The screened lanai and paver patio create easy indoor-outdoor living year-round. The only real decision left? Whether you’ll sip coffee on the welcoming front porch as neighbors pass by or unwind in your private backyard oasis listening to the whispering waves. Sorrento Shores is just minutes from Nokomis Beach (4 miles) and Venice Beach (6.5 miles), close to Oscar Scherer State Park and the Legacy Trail (1.5 miles), near the renowned Pine View School (2.9 miles), with convenient access to I-75, historic City of Venice (5.5 miles) and vibrant downtown Sarasota (12 miles). Here, functional updates, classic charm, location and lifestyle all come together — schedule your showing today!
Listing Agent: Lauren Sisco (904-652-9387)
61 BAYHEAD LN, OSPREY, FL 34229
$1,185,0003 Days on yellowkey MLS ID: A4685559
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3180 Built: 1993Monthly Fee: $458 Tax: $4,573 (2025)Community: OaksSpa: YesSingle Family
Taxes:$4,573
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: Thoughtfully Built MAINTENANCE-FREE Court Yard Life Style Home in Bishops Court in the Oaks Preserve Neighborhood. This Rare Unique Home Design Features: 3 Extra Large Bedrooms, 3 Full Baths, Oversized Main Floor Master Suite w/Sitting Room and Door to Private Back Patio, plus a Wall of Sliders Looking out to the Court Yard Pool Area, Tall Ceilings, Large Walk-in Closet w/Built-ins, Brand New Carpeting plus a 5-Piece Master Bath w/Soaking Tub; Formal Living and Dining Room are Open w/Tall Ceilings, Slider to Pool plus a Den/Library Room off the Living Room and Solid Wood Plank Flooring throughout; Open Kitchen w/Granite Counters and Breakfast Room w/Slider to Pool joined by a Family Room w/Fire Place and Solid Wood Plank Flooring; Pool Bath w/French Door, Main Floor Laundry Room w/Sink, Fabulous Upstairs Suite perfect for Guests or Extended Family w/Bonus Room, 2 Guest Bed Rooms w/Jack and Jill Bath; Extensive Crown Molding, Plantation Shutters thoughout, (2026) New Interior Paint, Central Vac, Large Side Load 2 Car Garage w/Storage, Newly Resurfaced Pool and Spa in the Screened-in Court Yard Entertaining Area, Court Yard Entry Gate, (2025) Brand New Designer Flat Tile Roof, (2026) Painted Pool Deck, (2026) Brand New Paver Driveway. WITH A FEW SIMPLE TOUCHES YOU CAN MAKE THIS HOME ABSOLUTELY FABULOUS! Have VISITORS Coming? NO PROBLEM. THIS HOME MAKES THE PERFECT ENTERTAINING OR SEASONAL FLOOR PLAN OFFERING A PRIVATE UPSTAIRS GUEST SUITE! Neighborhood Community Features: Local Community Pool, 24-Hour Secured Guard Gate, Lush Florida Landscaping and Irrigation are all included in the Maintenance Free Living. The OAKS GOLF & COUNTRY CLUB IS ONE OF SARASOTA'S PREMIER EQUITY "Creme de la Creme" GOLF COMMUNITIES! This amazing COUNTRY CLUB Features: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World Golfing (One of America’s Healthiest Clubs), Three Restaurants, Ballroom, Two 18-Hole Championship GOLF Courses, Award-Winning RACQUET Program w/12 HAR-TRU Hydro-Grid TENNIS COURTS, 4 PICKLE-BALL Courts, CROQUET, State of the Art FITNESS Center, Junior Olympic Heated Pool, Bocce Ball and Basketball Court, Playground Area plus so much more! Located just Minutes to the Top Rated Pine View School, Legacy Bike Trail, Florida's Best Coastal Beaches, Restaurants, Shopping and Costco. THE OAKS CLUB EQUITY MEMBERSHIP IS REQUIRED w/NO WAIT-LIST for SOCIAL or GOLF Memberships. Buyer Bonus: Seller is offering $40,000 towards Buyer's Equity Club Membership!!! ***Most Furnishings are Available Under a Separate Contract.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Anne Thomas, Pa (941-993-7700)
166 EDGEWOOD DR, OSPREY, FL 34229
$167,00017 Days on yellowkey MLS ID: A4687852
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 959 Built: 1977Monthly Fee: $215 Tax: $919 (2025)Community: ArborsManufactured Home
Taxes:$919
Remarks: Welcome to easy Florida living in The Arbors of Osprey! This charming 2-bedroom, 2-bath manufactured home offers comfort, updates, and plenty of space to relax and entertain. Step inside to a spacious living room filled with natural light, perfect for gathering with family and friends. The updated kitchen features warm wood cabinetry and a brand-new refrigerator (2025), making meal prep both stylish and functional. A separate dining area with a built-in buffet adds character and convenient storage. The primary suite provides a peaceful retreat with an ensuite bath, while the guest bedroom includes a desirable walk-in closet for added storage. Enjoy year-round sunshine in the light and bright Florida room, or unwind on the large screened lanai—ideal for enjoying Florida’s beautiful weather. Additional highlights include a storage shed with laundry, plywood underlayment replaced in 2014, and durable luxury vinyl flooring throughout. Major updates offer peace of mind with a new roof (2025), AC system (2023) and carport (2025). Located in the pet section of the community, this home is part of an active, friendly neighborhood featuring a clubhouse, swimming pool, shuffleboard courts, and a full calendar of social activities. Ideally situated between Sarasota and Venice, you’ll have easy access to boutique stye shopping, multiple dining options, theaters, performing arts venues, and stunning Gulf beaches. Everything you love about the Florida lifestyle just minutes away. This is relaxed, low-maintenance living in a welcoming community. Come see why so many love calling The Arbors home!
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