Location: Osprey
Do Not Show Listings
7204 JESSIE HARBOR DR #7204, OSPREY, FL 34229
$395,00043 Days on yellowkey MLS ID: A4697473
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1255 Built: 1985 Tax: $3,281 (2025)Community: Heron HouseSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,281
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: **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.
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
260 HIDDEN BAY DR #402, OSPREY, FL 34229
$775,000Listed 07/31/2026 10:50AM MLS ID: A4701000
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1950 Built: 2019 Tax: $7,780 (2025)Community: Edgewater/Hidden Bay Bldg B PhSpa: NoCondo
Taxes:$7,780
Remarks: Semi-furnished three-bedroom, 2.5-bath unit with elevator access. This fourth-floor residence offers beautiful panoramic intracoastal water views. Centrally between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay, a gated, 12- acre resort-style community on the water's edge of Little Sarasota Bay in Osprey. The building is designed in the architectural style of Key West. Enjoy breathtaking sunsets from your private screened-in balcony as you look out across the bay to the barrier island of Casey Key. Inside the unit, you'll find a spacious living room and dining room featuring an open floor plan. The gourmet kitchen offers KitchenAid stainless steel appliances, quartz countertops, white shaker-style cabinetry, counter seating and plenty of storage cabinets. The primary bedroom is expansive with large walk-in closets, closet organization system and direct access to the outside balcony. Both guest bedrooms have dual purpose, as they both have built-in Murphy beds, desk workstations, plantation shutters and walk-in closets. If you're looking for a condominium with extra space for a den/office/sewing room/craft room or TV media room, this is the one that offers it all. More great features are impact-resistant windows and doors, a large laundry room with built-in cabinetry, a full-size washer and dryer, and utility sink. One assigned parking space with a large storage unit with roll down door for all your extra gear. The location is walkable to many restaurants, shopping and the post office. Bike the Legacy Trail or head to the beach that's just a few miles away. There's so much to do just minutes away.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Thomas Netzel (941-539-0633)
701 PINE RUN DR #701, OSPREY, FL 34229
$172,00013 Days on yellowkey MLS ID: A4700416
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 586 Built: 1973 Tax: $1,648 (2025)Community: Pine Run ICondo
Taxes:$1,648
Remarks: Rare Treehouse Condo Available in Pine Run! Thinking of making the move to Florida? This charming one-bedroom condominium is the perfect place to start. Or just want a tiny house for ease of living? This is it! Bright and airy, the home features soaring cathedral ceilings and abundant natural light from both the east and west. The spacious living room opens through sliding glass doors to a balcony, creating a seamless indoor-outdoor living experience. Master bedroom with en-suite bath, vaulted ceiling and another balcony! The updated kitchen boasts beautiful butcher block countertops and you’ll enjoy peace of mind that comes with a NEW TANKLESS HOT WATER HEATER. Pine Run is a vibrant, amenity-rich community offering tennis and pickleball courts, two swimming pools, a clubhouse with a fitness room and over 20 acres of mature trees, lush landscaping and a scenic pond with water feature. Ideally located between Sarasota and Venice, you’ll be just minutes from the beautiful beaches of Siesta Key and Nokomis Beach. Shopping, dining and everyday conveniences along with the Intracoastal Waterway and one of the area’s favorite waterfront restaurants, Casey Key Fish House & Tiki Bar are all just a walk away! Come take a look - your new lifestyle is waiting - make it your own!
Listing is courtesy of: PAT WILLIAMS REALTY, LLC (941-289-6231)
Listing Agent: Pat Williams (941-289-6231)
2309 JESSIE HARBOR DR #2402, OSPREY, FL 34229
$497,00030 Days on yellowkey MLS ID: A4698434
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2006 Built: 2006 Tax: $5,978 (2025)Community: Blackburn Harbor Waterfront VillasSpa: NoCondo
Taxes:$5,978
Middle School: Sarasota Middle
Remarks: 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.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Christine Pope (941-685-5565)
14021 BELLAGIO WAY #309, OSPREY, FL 34229
$899,995176 Days on yellowkey MLS ID: A4681589
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2199 Built: 2006Monthly Fee: $1,585 Tax: $9,062 (2024)Community: Villas/Harbor VillageSpa: YesCondo
Taxes:$9,062
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Enjoy breathtaking sunset views overlooking the intercostal waterway in this boater's paradise, complete with an on-site marina. Discover coastal living in this beautifully updated 3-bedroom, 2.5-bath residence located in Bellagio Harbor Village. Ideally positioned between Sarasota Big Pass and the Venice Jetty, and just minutes from Midnight Pass and the Gulf of Mexico, this home offers easy access to pristine beaches, fine dining, and boutique shopping. Walkable to local restaurants and boat docks, the community is both conveniently located and peacefully serene. Offering 2,199 square feet of thoughtfully designed living space, this residence has been enhanced for comfort and style. Updates include new lighting throughout, featuring four coastal ceiling fans and elegant Caprice chandeliers. The spacious primary suite and two additional bedrooms feature new cordless blinds and window treatments, creating private and tranquil retreats. Bathrooms have been refreshed with new toilets, fresh paint, and an updated vanity in the powder room. The well-appointed kitchen showcases shaker-style cabinetry and enjoys stunning Intracoastal and sunset views. Step onto the private lanai and enjoy seamless indoor-outdoor living with direct access to the pool area. Newly installed retractable screens provide shade and privacy when desired while preserving expansive water views. Outdoor enthusiasts will appreciate the on-site kayak storage and launch area, perfect for exploring the surrounding waterways. Located in southwest Osprey, this exceptional residence offers both a beautiful home and a vibrant waterfront community. Residents enjoy access to a resort-style pool, hot tub, sauna, and open-concept gathering spaces—creating a lifestyle where every day feels like a vacation.
Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)
Listing Agent: Tristin Hopler (941-735-3520)
5100 JESSIE HARBOR DR #304, OSPREY, FL 34229
$725,000101 Days on yellowkey MLS ID: A4690942
REDUCED by $10,000 (1.4%) on 06/16/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2143 Built: 2004 Tax: $6,004 (2025)Community: Blackburn Harbor ResidencesCondo
Taxes:$6,004
Remarks: Experience effortless coastal living in this stunning third-floor FURNISHED waterfront residence, perfectly positioned for boaters and kayakers in protected waters just off Blackburn Bay and minutes from the Intracoastal Waterway and Gulf. Watch dolphins, manatees, otters, and breathtaking sunsets from your private balcony. Your water views continue inside, flowing through the living room, dining area, kitchen, and primary suite. This spacious, designer-furnished home showcases quartz surfaces, tile and luxury vinyl flooring, a primary suite with balcony access, oversized shower, jacuzzi tub, and three closets. This unit includes a beautifully appointed second bedroom and a versatile den that is currently used as a 3rd bedroom. There is ample storage inside and out- including a first-floor storage unit ideal for all your water toys. Use the community kayak launch for access to Blackburn Harbor and Oscar Scherer State Park. Enjoy the rare opportunity to keep your boat in your backyard with dockage currently available. Your home is set within an 11-acre gated community featuring walking trails, tennis and pickleball courts, a resort-style pool, waterside grill, clubhouse, and fitness center, all just minutes from Nokomis Beach, the Legacy Trail, and vibrant dining and shopping—this is truly the ultimate Florida waterfront lifestyle you’ve been waiting for.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Suki Scollo (941-587-2289)
4271 EXPEDITION WAY #103, OSPREY, FL 34229
$260,000113 Days on yellowkey MLS ID: A4689541
REDUCED by $5,000 (1.9%) on 07/22/2026
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)
4226 FRONTIER LN #103, OSPREY, FL 34229
$299,000116 Days on yellowkey MLS ID: A4687965
REDUCED by $20,000 (6.3%) on 05/16/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1135 Built: 2018Monthly Fee: $475 Tax: $3,542 (2025)Community: Bay Street VillageCondo
Taxes:$3,542
Remarks: Coastal convenience meets effortless living, just minutes from Siesta Key, America’s #1 beach. Welcome to 4226 Frontier Lane, a beautifully maintained 2-bedroom, 2-bath walk-up condo in the gated community of Bay Street Village, offering exceptional value and an easy Florida lifestyle. Built for peace of mind with hurricane impact windows concrete-block construction. A private ground-level garage provides added convenience and storage. Upstairs, the bright, open-concept floor plan is filled with natural light, creating an inviting space for both everyday living and entertaining. The well-appointed kitchen features 42" cabinetry, granite countertops, stainless steel appliances, and a spacious walk-in pantry, seamlessly flowing into the dining and living areas. Step out onto your large, screened-in lanai to enjoy peaceful mornings or evening cocktails. The generously sized primary suite offers a walk-in closet and an ensuite bath with dual vanities and a tiled walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Ideally located in Osprey, between Sarasota and Venice, you’ll enjoy a quiet, tucked-away setting with shopping, dining, and daily conveniences just minutes away. Bay Street Village residents enjoy resort-style amenities including a heated pool, fitness center, and clubhouse. With reasonable HOA fees covering exterior maintenance, roof, water, sewer, and gated access (and no flood insurance required) this is truly low-maintenance ownership at its best. Perfect as a full-time residence, seasonal escape, or investment opportunity this is Florida living, simplified.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Kate Kwiecinski (412-477-9720)
6100 JESSIE HARBOR DR #202, OSPREY, FL 34229
$850,00090 Days on yellowkey MLS ID: A4690969
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 3771 Built: 2005Monthly Fee: $1,101 Tax: $8,698 (2025)Community: Blackburn Harbor ResidencesCondo
Taxes:$8,698
Remarks: Virtually Staged. Experience elevated coastal living in this beautifully appointed waterfront residence, ideally located within the sought-after Blackburn Harbor community in Sarasota County. Situated on the second floor (building with elevator), this elegant and spacious 3BR + den / 3BA condominium offers over 3,700 SF of a harmonious blend of style and comfort, complemented by serene water views. The open-concept layout features expansive living and dining spaces bathed in natural light, perfect for both everyday living and effortless entertaining. Sliding glass doors lead to a generous wrap-around lanai, creating a seamless indoor-outdoor setting to relax and enjoy tranquil water views, refreshing coastal breezes and spectacular sunsets. The gourmet kitchen is as functional as it is inviting, showcasing rich wood cabinetry, granite countertops, stainless steel appliances, a center island for culinary enthusiasts, and a cozy dinette. A convenient breakfast bar opens to the main living area, ideal for casual dining and social gatherings. The primary suite serves as a peaceful retreat, complete with ample closet space and a well-appointed en-suite bath. Each additional bedroom features its own en-suite bathroom and walk-in closets, offering comfort and privacy for guests or versatility for a home office. Residents of Blackburn Harbor enjoy an array of resort-style amenities, including a heated pool, fitness center, clubhouse, tennis and pickleball courts, kayak storage and launch, and a gazebo with grilling areas. Boating enthusiasts will appreciate the protected deep-water dockage with power and water, and direct access to the Intracoastal Waterway with no bridges. Surrounded by natural beauty, the community provides a front-row seat to Florida’s coastal wildlife, including dolphins and manatees. Just across the street, Oscar Scherer State Park offers scenic trails and outdoor recreation, while nearby waterways invite kayaking adventures to local favorites like Casey Key. Perfectly positioned between Venice (10 minutes) and Sarasota (25 minutes), this location offers convenient access to shopping, dining, and cultural attractions, as well as world-renowned Gulf beaches, including Siesta Key Beach just 15 minutes away. Whether you’re seeking a seasonal escape or a year-round residence, this exceptional property captures the essence of Florida waterfront living.
Listing is courtesy of: CORCORAN DWELLINGS REALTY (941-200-4663)
Listing Agent: Angelic Tassos (917-450-0316)
754 PINE RUN DR #754, OSPREY, FL 34229
$259,00082 Days on yellowkey MLS ID: A4693150
REDUCED by $10,000 (3.7%) on 06/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1379 Built: 1973Monthly Fee: $917 Tax: $3,176 (2025)Community: Pine Run ISpa: NoCondo
Taxes:$3,176
Remarks: Virtually Staged. Rarely available and truly one-of-a-kind, this beautifully updated ground-floor 2-bedroom, 2-bath residence offers an exceptional combination of privacy, architectural character, and an unbeatable location. Designed around a stunning private open-air atrium, the home features 8-foot glass doors on three sides, flooding the interior with natural light and creating a seamless indoor-outdoor connection rarely found in condominium living. The thoughtfully designed floorplan delivers a tranquil, nature-inspired experience—particularly from the south bedroom wing, where walls of glass frame peaceful wooded views, offering a remarkable sense of serenity and privacy. Beautifully modernized for today’s lifestyle, the kitchen and living spaces have been opened into a sophisticated great-room design, ideal for entertaining and everyday comfort. Timeless Saltillo Mexican tile flooring runs throughout, adding warmth, texture, and character. Additional conveniences include covered carport parking, a large private storage closet, and tasteful updates that make this residence completely move-in ready. Residents enjoy an impressive collection of resort-style amenities, including two heated pools—one dramatically overlooking a wildlife-filled lagoon—along with two cedar saunas, a fitness center, a Florida-style clubhouse, scenic walking trails, BBQ gas grills, an outdoor gas fireplace, kayak storage, and tennis and pickleball courts. Perfectly positioned for an active coastal lifestyle, this premier location places you just minutes from Nokomis Beach, Oscar Scherer State Park, multiple kayak launches, a public boat ramp, and the Legacy Trail, offering miles of biking and recreation connecting Venice and Sarasota. Nearby favorites include Casey Key Fish House, Historic Spanish Point, waterfront dining, medical facilities, and endless local conveniences. Everyday living couldn’t be easier—walk to Publix, CVS, Ace Hardware, shops, restaurants, fitness centers, Walmart, and the Post Office, or enjoy quick access to everything the area has to offer without needing a car. Families will appreciate proximity to the highly acclaimed Pine View School for the Gifted—the only standalone public gifted school in Florida and consistently ranked among the state’s best. Combining exceptional privacy, thoughtful design, resort-style amenities, and unmatched convenience, this is a rare opportunity to own a distinctive, beautifully updated home in one of the area’s most desirable locations—perfect for those seeking the ideal balance of nature, accessibility, and modern coastal living.
Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)
Listing Agent: Sasha Volosevych (971-703-0307)
385 N POINT RD #402, OSPREY, FL 34229
$615,000553 Days on yellowkey MLS ID: A4635708
REDUCED by $45,000 (6.8%) on 07/27/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2055 Built: 2000Monthly Fee: $400 Tax: $5,877 (2024)Community: Meridian At The Oaks PreserveSpa: NoCondo
Taxes:$5,877
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: **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.
401 N POINT RD #1001, OSPREY, FL 34229
$1,995,000181 Days on yellowkey MLS ID: A4679998
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3029 Built: 2003Monthly Fee: $400 Tax: $10,201 (2025)Community: Meridian At The Oaks PreserveSpa: YesCondo
Taxes:$10,201
Elementary School: Pine View School
High School: Pine View School
Middle School: Pine View School
Remarks: **Rarely available 10th-floor penthouse corner residence offering 3,029 square feet with sweeping Gulf and Bay views.** Ideally situated behind the secure gates of the highly sought-after Preserve neighborhood within The Oaks Country Club, this exceptional condo features 3 Bedrooms plus Den, 3 Full Baths, Private 2-Car Garage, and climate-controlled storage. The open-concept floor plan is designed to maximize the breathtaking vistas, with panoramic views from the great room, dining area, kitchen, owner’s suite, and expansive balcony. Interior highlights include 10ft ceilings, crown molding, engineered hardwood and tile flooring throughout, and plantation shutters. The well-appointed kitchen offers newer Cambria quartz countertops (2022), solid wood cabinetry, counter seating, and newer stainless-steel appliances (2023). The spacious primary suite features walk-in closets and a luxurious bath with dual vanities, a custom-tiled shower, and a soaking tub. Residents enjoy private amenities including a heated pool and spa, fitness center, and outdoor grilling area, along with full access to The Oaks Club’s renowned lifestyle amenities. Meridian Tower #3 also features a new roof (2025). THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **Please Enjoy Viewing the 3D VIRTUAL TOUR**
4213 EXPEDITION WAY #107, OSPREY, FL 34229
$320,00030 Days on yellowkey MLS ID: A4698337
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1430 Built: 2016Monthly Fee: $475 Tax: $3,428 (2025)Community: Bay Street VillageCondo
Taxes:$3,428
Remarks: "Location, Location, Location" The luxury Florida lifestyle you’ve been dreaming. Welcome to this beautifully appointed 3-bed, 2-bath walk-up condo in a highly desirable location in a pet-friendly gated community. Built for peace of mind, the community features solid concrete block construction and hurricane-impact windows for added safety and durability. The attached ground-level garage beneath the residence offers convenience when arriving or heading out. The open-concept layout floor plan, soaring ceilings, and split-bedroom layout create perfect privacy. Stunning chef’s kitchen, granite countertops, stainless steel appliances, and a center island with seating, walk-in pantry, and upgraded fixtures. The primary suite features a walk-in closet, a spa, a double vanity, and a walk-in shower. Two other bedrooms on the opposite side, along with a second full bathroom, gives comfort and privacy for families or guests. Relax on the screened-in lanai overlooking beautiful water views for morning coffee or evening cocktails. The Tesla charger installed in the garage is a bonus. The community is located in a prime location with quick access to US-41, I-75, Siesta Key Beach, and Nokomis Beach, Bay Street Park with its playground and dog park, and walking distance to renowned Pine View School, Walmart, and the Legacy Trail. Bay Street Village resort-style amenities include a heated pool, fitness center, and clubhouse. The monthly condo fee covering exterior maintenance, roof, water, sewer, and two gated entrances… Don’t miss this rare opportunity – call the listing agent now to schedule a private viewing.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Yunfei Liu (941-928-8573)
108 WOODLAND PL #108, OSPREY, FL 34229
$285,00022 Days on yellowkey MLS ID: A4699279
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1316 Built: 1979 Tax: $3,100 (2025)Community: Pine Run IiCondo
Taxes:$3,100
Remarks: Bring your furniture and move right in to this popular Pine Run neighborhood. No need to worry about remodeling this condo! New coastal look ceramic tile throughout the entire home! New kitchen and appliances, new guest bathroom, new doors throughout, new light fixtures, and newly painted. Wow! First floor condo offers more outdoor living space. The patio off the main entry offers privacy and has access from the dinette area. A spacious center atrium feels like a peaceful retreat. The main covered lanai off the living room and dining room is screened in with a door to the back yard. Each bedroom has it’s own small patio with privacy fence. Kitchen is nicely equipped with washer and dryer in the dinette closet area. The hallway has large almost floor to ceiling windows looking onto the center atrium for a very open feel. Pine Run is an active community nestled between mature landscaping and trees, with many activities including pickleball, tennis, kayak storage and two swimming pools! Launch your kayaks in the Blackburn Point Park and boat launch just down the road. Pine Run is conveniently located near shopping, restaurants, major roads and Casey Key Fish House and Tiki Bar. Sarasota is about 13 miles away, Venice about 7 miles. Area beaches are close at hand with Nokomis Beach just 5 miles and Siesta Key Beach is 9 miles. You are in the heart of paradise! Come see for yourself!
14041 BELLAGIO WAY #318, OSPREY, FL 34229
$949,00051 Days on yellowkey MLS ID: A4696101
0 Days Off yellowkey (back on 7/26/2026)
REDUCED by $50,000 (5.0%) on 07/07/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2086 Built: 2006Monthly Fee: $1,512 Tax: $7,362 (2025)Community: Villas At Bellagio Harbor VillageSpa: YesCondo
Taxes:$7,362
Remarks: Under contract-accepting backup offers. Virtually Staged. Under contract- accepting back up offers. Newly priced at $949,000. Boaters, sunset lovers, and buyers seeking a true Gulf Coast lifestyle will appreciate this spacious waterfront condominium in The Villas at Bellagio Harbor Village, complete with a 37 foot wet slip included in the sale. This 3 bedroom plus den, 2 bath residence offers 2,086 square feet of living space, plus large lanai, private elevator entry, and beautiful west facing views over the water and marina. The open floor plan features a generous great room, covered lanai, large kitchen with newly painted cabinetry, interior laundry room, and two assigned under building parking spaces that are next to each other. Water views are spectacular from entry, great room, kitchen and primary bedroom. Doors leading to lanai in great room, kitchen and primary bedroom. Residents of The Villas at Bellagio Harbor Village enjoy resort style amenities including a heated waterfront pool and spa, fitness center, clubhouse, sauna, kayak launch, gated entry, elevator access, and a marina setting. Roofs were replaced in 2025. The community is ideally located near Blackburn Point, Casey Key, Oscar Scherer State Park, waterfront dining, shopping, beaches, Sarasota, Venice, and all that Osprey has to offer. Whether you are looking for a full time residence, seasonal retreat, or waterfront getaway with boating access, this condo delivers a rare combination of space, views, amenities, and an included wet slip in a beautiful coastal setting.
Listing is courtesy of: COLDWELL BANKER REALTY (941-487-1492)
Listing Agent: Margot Leonard (941-387-5050)
120 WOODLAND PL #120, OSPREY, FL 34229
$299,00021 Days on yellowkey MLS ID: D6148025
0 Days Off yellowkey (back on 7/16/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1979 Tax: $2,712 (2025)Community: Pine Run IiSpa: NoCondo
Taxes:$2,712
Remarks: Under contract-accepting backup offers. Over $80,000 in upgrades and designer renovations by renowned Murray Homes, a symbol of luxury in Sarasota. The team included an architect, designer, and contractors to transform this Pine Run end-unit, second-floor condo into a stunning modern coastal retreat. Featuring a completely reimagined light and bright open floor plan and custom kitchen with quartz countertops, custom cabinetry, floating shelves, designer tile backsplash, stainless appliances, and workstation sink, this move-in-ready home also offers luxury wide-plank flooring throughout, beautifully updated bathrooms, newer HVAC, fresh interior paint, contemporary lighting, new trim, doors, hardware, and window treatments, new ceiling fans, new stackable washer and dryer. Primary bedroom is ensuite with a walk-in closet and both bedrooms enjoy a private balcony. The spacious screened lanai is private and overlooks lush tropical landscaping, creating the perfect setting to relax and enjoy Florida living. There is an abundance of storage closets and attic space. Covered end-unit parking with storage and guest parking. Walk to shopping and waterfront bars and restaurants. Ideally located just minutes by bike to Nokomis Beach, Casey Key, Oscar Sherer State Park, and the Legacy Trail, Pine Run offers resort-style amenities including two pools, tennis and pickleball courts, kayak storage and launch, a clubhouse, and gym. Luxury, location, and lifestyle—all in one exceptional, and updated-to-like-new condo ready for you to call home.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Kim Kruysman (941-441-6628)
14041 BELLAGIO WAY #214, OSPREY, FL 34229
$700,000109 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
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)
2251 JESSIE HARBOR DR #2101, OSPREY, FL 34229
$359,00029 Days on yellowkey MLS ID: A4698891
0 Days Off yellowkey (back on 7/20/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1400 Built: 2006 Tax: $4,920 (2025)Community: Blackburn Harbor Waterfront ViCondo
Taxes:$4,920
Remarks: Under contract-accepting backup offers. INCREDIBLE VIEWS!....INCREDIBLE LOCATION!...You Will be Wowed by the LONG WATER & SUNSET VIEWS in this Bright and Spacious (2) Bedroom (2) Bath Corner Unit with PRIVATE GARAGE located in Blackburn Harbor Waterfront Villas, a PET FRIENDLY Gated 11 acre Waterfront Resort-Style Community with: HeatedPool; Fitness Center; Kayak Storage & Launch; BBQ Gazebo; Dog Park; Walking Trails; Pickleball/Tennis and****BOAT SLIPS****for easy "no bridges" access to Intracoastal & Gulf......Abundance of Storage; Ideal Split Bedroom Floor Plan; TILE THROUGHOUT & Expansive Screened Lanai---providing the Ultimate Indoor/Outdoor Living and PERFECT for Morning Coffees, Enjoying Your Favorite Podcast and of course, SUNSET COCKTAILS!....Blackburn Harbor is Conveniently Located to EVERYTHING: Shopping; Dining; Recreation; the New Sarasota Memorial Hospital; Legacy Bike Trail and just minutes to MULTIPLE BEACHES, including TOP RATED SIESTA KEY!....Ideal as Year-Round; Vacation or Investment Property!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Mike Martino (773-619-8593)
401 N POINT RD #301, OSPREY, FL 34229
$459,900868 Days on yellowkey MLS ID: A4603773
REDUCED by $15,100 (3.2%) on 07/20/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2594 Built: 2003Monthly Fee: $367 Tax: $6,783 (2023)Community: Meridian At The Oaks PreserveCondo
Taxes:$6,783
Tax Year: 2023
Remarks: 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.
Listing Agent: Steve Abbe (941-400-3969)
4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229
$318,000148 Days on yellowkey MLS ID: N6143250
0 Days Off yellowkey (back on 7/15/2026)
REDUCED by $10,000 (3.0%) on 06/22/2026
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: Under contract-accepting backup offers. Virtually Staged. Spectacular water views from most windows in this immaculate, lightly used 3BR/2BA condo, built in 2018 and located in the gated community of Bay Street Villages. The popular Ibis floor plan offers an open-concept kitchen, dining, and great room with designer finishes, including white 42” cabinetry, light granite countertops, custom backsplash and stainless-steel appliances. Enjoy peaceful pond views with birds and wildlife from the screened lanai. Quality construction and peace of mind are provided by hurricane-impact windows and doors, concrete block construction, tile roof, and a paver driveway. The primary suite features plantation shutters, a custom ceiling fan with light, custom closet system, linen closet, lighted 10× makeup mirror, and a bidet-ready outlet. The second and third bedrooms also include custom ceiling fans and 2" blinds. The dining area is accented by a custom light fixture and accordion blinds on the balcony sliding doors. The balcony is enhanced with a tropical palm-leaf ceiling fan and outdoor curtains for added shade and comfort. The great room is fitted with plantation shutters for added elegance. A spacious laundry room includes a washer and dryer. Added features-Ring Doorbell, Keyless Entry on Front Door as well as an Exterior Garage door keypad. The monthly condo fee includes water, sewer, exterior and grounds maintenance, gated entry, heated resort-style pool, cabana, fitness center, and club room. No CDD fees. Ideally located near Nokomis Beach, Casey Key, Siesta Key Beach, the Legacy Trail, Sarasota and Venice dining and shopping, Oscar Scherer Park, and A-rated Pine View School. Maintenance-free Florida living at its best.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Tim Weller (941-221-0155)
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