Location: Osprey
Do Not Show Listings
401 N POINT RD #504, OSPREY, FL 34229
$880,0007 Days on yellowkey MLS ID: A4696459
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2778 Built: 2003Monthly Fee: $400 Tax: $8,767 (2025)Community: Meridian At The Oaks PreserveSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,767
Elementary School: Gulf Gate Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: INCREDIBLE OPPORTUNITY AND A MUST SEE AT THE MERIDIAN AT THE OAKS - GREAT PRICE, BAY VIEW, UPDATED KITCHEN, PRIVATE 2 CAR GARAGE AND MORE! Beautifully updated and thoughtfully designed, this exceptional 5th floor residence in The Meridian at The Oaks Preserve offers tranquil water and preserve views, a fantastic floor plan, and the rare convenience of a private 2-car garage just steps to the elevator lobby. The expansive split-bedroom floor plan includes 3 bedrooms, 3 full baths, and a private den/study/office that can easily function as a 4th bedroom, providing exceptional flexibility for both everyday living and visiting guests. Filled with natural light, the spacious great room and dining areas flow seamlessly to the generous terrace with upgraded ceramic tile, where peaceful water and preserve views create a serene backdrop for relaxing or entertaining. The custom kitchen, redesigned in 2023, is both elegant and functional, featuring soapstone countertops, Bosch appliances, roll-out cabinetry, Everpure water filtration, a tray ceiling, and detailed crown molding. The primary suite is a private retreat, offering picturesque water views, a custom-designed walk-in closet, and a beautifully appointed bath with Italian tile, dual vanities, and stunning stone countertops. Custom built-ins, upgraded closet systems, and a thoughtfully designed laundry room further enhance the home's comfort and functionality. Residents of The Meridian enjoy lushly landscaped grounds, winding pathways, a community pool and spa, fitness center, and outdoor grilling area. Membership in The Oaks Club is required, providing access to one of Sarasota's most distinguished private club lifestyles, including two championship golf courses, 12 Har-Tru tennis courts, pickleball, croquet, a state-of-the-art wellness center, resort-style pool, multiple dining venues, a vibrant social calendar, and an elegant clubhouse. Ideally located near Historic Spanish Point, Pine View School, Siesta Key Beach, and downtown Sarasota, this exceptional residence offers a rare combination of luxury, privacy, natural beauty, and resort-inspired living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lenore Treiman (941-356-9642)
7204 JESSIE HARBOR DR #7204, OSPREY, FL 34229
$395,000Listed 06/19/2026 9:35AM 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
Taxes:$3,281
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Middle School: Laurel Nokomis Middle
Remarks: **BEAUTIFULLY UPDATED CONDO, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO** Featuring 2 Beds and 2 Full Baths, this FULLY RENOVATED, 2ND FLOOR unit features an Impressive Kitchen with quartz counters, stainless steel appliances, new solid wood cabinets while the Spacious Owner’s Suite boasts custom built-in cabinets/closets and an equally Elegant Bath. CoreTec Vinyl Flooring throughout (except guest bedroom). Enjoy the serene and natural surroundings from your elevated, sprawling and screened balcony which is accessible from multiple rooms via sliding doors. This Secure and Gated Community offers the ultimate Florida Lifestyle! Amenities include Community Pool, Tennis and Pickleball Courts, Clubhouse with Fitness Center, Boat Dock (subject to availability), Kayak launch and storage, Gazebo with BBQ, etc. Private covered parking and storage are located on the ground level within the building. Blackburn Harbor is ideally situated in Osprey between Sarasota and Venice and is just minutes minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer! **RECENTLY COMPLETED PROJECTS INCLUDE: ASPHALT PAVING, IRRIGATION, WALKWAYS, WALKWAY LIGHTING, LIGHTING at TENNIS AND PICKLEBALL COURTS, etc.
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
754 PINE RUN DR #754, OSPREY, FL 34229
$259,00039 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: 1973 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)
1474 LANDVIEW LN, OSPREY, FL 34229
$1,475,0006 Days on yellowkey MLS ID: A4696853
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3246 Built: 1977Monthly Fee: $219 Tax: $9,834 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$9,834
Remarks: Elevated luxury throughout this Southbay beauty! Step inside this one of a kind two story home and you will feel like you are a top resort! You will enter the foyer overlooking the living room and dining room area, just perfect for entertaining highlighting a built-in buffet with wine cooler. Open the sliding glass doors ahead and enter the exquisite out door living area, heated salt water pool, spa, outdoor kitchen and dining area, all adding up to the feeling of relaxed elegance. The kitchen is a dream! Top of the line Thermador appliances including a smooth induction top stove, built in oven and microwave and for the ultimate in extravagance - a built in Thermador coffee maker. Quartzite counter tops, over sized island, custom pantry, sliding glass doors to exterior help complete this gathering spot. Located on the first floor is the spacious master suite with triple sliding doors looking onto the lanai area. Master bath with tub and an oversized window looking onto a private zen garden. The spacious second bedroom currently used as an office features corner windows and has a full luxury guest bath right out side its door. The oversized family room with vaulted ceiling and wood beam accents will be a great family retreat with a built in new state of the art fireplace and TV. Unique pebbled wallpaper adorns one wall to help maintain the resort feel. First floor laundry with built in cabinets is also on the first level. Upstairs you will find two nice sized bedrooms plus a full bath with double bowl sinks. The upstairs bonus room is a fun hideaway for a play room, office, or workout room, featuring glass French doors. Plenty of storage in this home with several attic accesses. Other important features include plantation shutters through-out, one new A/C unit in 2025, attic TAP insulation installed 2025, stackable washer and dryer 2024, new GAF coating on TPO flat roof (lanai), interior painted 2024, extensive landscaping 2025 including addition of a side private patio, and lanai wood ceiling 2025 and new hurricane rated glass in double front door. All the beautiful furnishings and decor items in the home are negotiable as well. So many more details you will just have to come and see for yourself. The Southbay Yacht and Racquet Club is a vibrant community with many amenities, activities and offers it’s own marina to residents. The marina dock fees are low and has space for most boat sizes. Also in the marina is a kayak launch and storage on site. The renovated clubhouse offers a fitness center, 99 person ballroom, livingroom, two kitchens, pool, bocce balls, tennis and pickleball. Centrally located between Sarasota and Venice, area beaches, restaurants and shopping. The local favorite restaurant, Casey Key Fish House & Tiki Bar is right down the road! Southbay is a fabulous place to live and play - and as they say, come and buy your boat a home!
Listing is courtesy of: PAT WILLIAMS REALTY, LLC (941-289-6231)
Listing Agent: Pat Williams (941-289-6231)
113 BURNEY RD, OSPREY, FL 34229
$999,50057 Days on yellowkey MLS ID: A4690672
Bed: 3 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2502 Built: 2020 Tax: $10,455 (2025)Community: Bel-AirSpa: YesSingle Family
Taxes:$10,455
Elementary School: Pine View School
High School: Pine View School
Middle School: Pine View School
Remarks: **DON’T WAIT TO BUILD!! NEWER, CUSTOM-BUILT HOME (2020) IS MOVE-IN READY AND PACKED WITH UPGRADES** Situated on a generous 0.52-acre lot near the end of a quiet cul-de-sac, the property offers a private backyard and NO HOA fees/restrictions. Bring Your Toys! Oversized circular driveway provides ample parking for a BOAT, RV, and additional vehicles. This Impressive Residence with 2502sf of heating living space, features 3 Bedrooms plus Study/Den, 2 Full and 1 Half Baths, and a 3-car tandem garage. The Light and Bright, Open Floor Plan is enhanced by tile flooring throughout, tray ceilings, Hurricane Impact Windows and Sliding Doors, plantation shutters, etc. The expansive kitchen is designed for both everyday living and entertaining, featuring a large island, hardwood cabinetry, and premium stainless-steel appliances including Thermador, Bosch, etc. The owner’s suite offers a large, divided walk-in closet and a luxurious en-suite bath with dual vanities and a custom-tiled shower. A spacious, screened lanai provides a beautiful view of the expansive, landscaped and private backyard while showcasing a Heated/Cooled, Saltwater Pool/Spa, along with a large, covered seating area and an Outdoor Kitchen BBQ, Quartzite countertop/sink —perfect for enjoying Florida’s outdoor lifestyle. The Ideally located with easy access to US-41 (Tamiami Trail), this home is just a short drive to world-renowned beaches including Nokomis Beach and #1 rated Siesta Beach, shopping, dining, cultural attractions, and the highly rated Pine View School. **Please Enjoy Viewing the 3D VIRTUAL TOUR**
730 FORDINGBRIDGE WAY, OSPREY, FL 34229
$710,000Listed 06/19/2026 8:38AM MLS ID: A4697358
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2182 Built: 2002Monthly Fee: $120 Tax: $6,488 (2025)Community: Rivendell WoodlandsSpa: YesSingle Family
Taxes:$6,488
Middle School: Sarasota Middle
Remarks: There’s a quiet kind of beauty in a home that just feels right the moment you walk in, where the light pours through the windows, the spaces flow effortlessly, and every detail invites you to slow down and stay awhile. Welcome to this thoughtfully designed 3-bedroom + den, 2-bath retreat tucked inside the beloved Woodlands at Rivendell. The kind of neighborhood where tree-lined streets and timeless charm set the tone for everyday living. Step inside and you’re greeted by an airy, open layout that feels both spacious and warm. The main living spaces are grounded by rich, hand-scraped engineered hardwood floors, while large sliding doors disappear into the walls, blurring the line between indoors and out in the most beautiful way. Out back, the home truly comes to life. The gas-heated, saltwater pool and spa, with its soft, cascading glass waterfall, creates a peaceful backdrop for everything from slow mornings to lively evenings with friends. The lanai has been freshly painted, giving the entire outdoor space a clean, refreshed feel that’s ready to be enjoyed year-round. The kitchen sits at the heart of the home, open, inviting, and designed for gathering. With an induction cooktop, stainless steel appliances, generous cabinetry, and a walk-in pantry, it’s as functional as it is welcoming. Tucked just off the main living area, the den offers a quiet place to work, read, or simply unwind, made even better by its natural light and calming views of the pool and pond. The split floor plan creates a sense of privacy, with two guest bedrooms positioned toward the front of the home and the primary suite set apart as its own retreat. Here, you’ll find two walk-in closets, soft natural light, and sliding doors that lead directly to the pool. The ensuite bath feels like a spa escape, complete with a soaking tub, walk-in shower, dual vanities, and a private water closet. And it’s not just beautiful, it’s been thoughtfully updated. In 2024, the home was refreshed with new interior paint, lanai floor paint, a portable generator, and new washer, dryer, and refrigerator. In 2025, a new HVAC air handler was installed, and in 2026, brand-new carpet was added to the bedrooms. Plantation shutters throughout add a timeless finishing touch, while every update has been made with care to ensure comfort and ease for years to come. Beyond the home, the location brings together the very best of Florida living, just minutes from Nokomis Beach, Siesta Key, downtown Sarasota, and Venice. With easy access to I-75 and US-41, and nestled alongside Oscar Scherer State Park and Pine View School, Rivendell offers both convenience and a sense of peaceful retreat. This is the kind of home that doesn’t just check the boxes, it tells a story. One of light, warmth, and living well every single day. Home is being offered partially furnished.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Christina Gaskill (941-539-0445)
433 E MACEWEN DR, OSPREY, FL 34229
$2,250,000171 Days on yellowkey MLS ID: A4676505
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4012 Built: 1998Monthly Fee: $142 Tax: $17,426 (2025)Community: OaksSpa: YesSingle Family
Taxes:$17,426
Remarks: An exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths situated on the interior Heron golf course on a 0.61 acre lot in the private Oaks Club community. It has golf course and water views and 24 hr gated security. This custom golf course home was built by esteemed builder Arthur Rutenberg. It represents Rutenberg at his very best - stylish elegance, superior craftsmanship designed to accommodate the seamless indoor-outdoor transfer so critical to Florida living. Most prominently the home features 12 foot high ceilings in most rooms, designed to maximize the home's grander, air flow and natural light. The previous owners called it "The House of Light”. The Rutenberg influence abounds in other stunning details starting with the lighted entrance posts, the dramatic circular driveway and the centrally located kitchen that seamlessly opens to a comfortable family/TV room. The home has magnificent coffered ceilings, distinctive crown molding and a gas fire place. Its oversized screened lanai encompasses substantial undercover space for family and guest dining. It is visually highlighted by a 4 foot high tile wall at the head of the pool with a waterfall feature. The kitchen is a cooks delight with new granite counters, stainless steel appliances, including SUBZERO and WOLF. The master bathroom has dual vanities and a large custom tiled shower and soaking tub. The oversized 3 car garage has amble storage capacity, a work table and a refrigerator. Mr. Rutenberg would be pleased to know that this meticulously crafted home has been skillfully updated over the years by all its owners. These improvements include - 1.) hurricane windows and doors (2020), 2.) Roof (2019), 3.) Cage - aluminum structure (2018) 4.) Screened under-cover outdoor grilling area - granite tops, refrigerator, seating for 4, Alfresco grill (20xx). The Oaks has been a member owned private residential golf club for over 40 years. It boosts many accolades, including being the only private residential golf club in the Sarasota/Bradenton/Fort Myers area recognized for high achievement by both Platinum Clubs of America and Distinguished Emerald Clubs of World. It has also been recognized as “The Healthiest Club" and is a certified Audubon Society award recipient. The club has a magnificent 30,000 square foot club house, three exquisite dinning venues, two 18 hole well maintained championship golf courses featuring excellent professional instruction, an outstanding racquets program with 12 har-tru Hydo Grid courts, 4 pickle ball counts, a vibrant croquet program with a regulation sized lawn, a state-of-the-art (newly expanded) wellness/fitness/spa facility, a junior olympic swimming pool, Bocce and a basketball court. Families with children are very welcome here. The Oaks Club’s ideal Sarasota County location places it minutes away from - Sarasota’s vibrant arts and cultural scene and great shopping. It also provides easy access to the expanded Sarasota airport, world class medical care and some of the most beautiful beaches in the world. There is no waitlist for membership.
557 CRANE PRAIRIE WAY, OSPREY, FL 34229
$599,0007 Days on yellowkey MLS ID: A4696823
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2172 Built: 2005Monthly Fee: $397 Tax: $3,953 (2025)Community: Willowbend Ph 4Single Family
Taxes:$3,953
Remarks: Welcome to this impeccably maintained, MAINTENANCE FREE home in the highly desirable Willowbend community, with tranquil LAKEVIEWS, exceptional amenities and an unbeatable LOCATION. Built by renowned Lee Wetherington and lovingly maintained by its original owner, this quality-constructed residence features a spacious open split-bedroom floor plan with 3 bedrooms plus den, 2 baths, and abundant storage throughout. The kitchen boasts natural wood cabinets with granite counters, a breakfast bar and newer stainless appliances with natural gas for cooking and a pantry for additional storage. The heart of the home opens to a stunning extended screened lanai surrounded by lush vegetation overlooking a private water view, where you can enjoy breathtaking sunrises and watch Florida's natural wildlife in a peaceful setting. Additional upgrades to this immaculate home include an EV charging station, whole-house carbon water filtration system, and natural gas service for the stove, dryer, and water heater. HOA fees provide outstanding value and include lawn maintenance, irrigation, high-speed internet, cable, and access to resort-style amenities including a community heated pool, fitness center, playground and pickleball courts. Ideally situated within a mile of Pine View School and just moments from Oscar Scherer State Park and the Legacy Trail, this home also offers quick access to Nokomis Beach, only two miles away. Trader Joe's, Whole Foods, shopping, dining, and everyday conveniences are all nearby, making this location truly second to none. Enjoy the perfect combination of comfort, convenience, low-maintenance living, and the Florida lifestyle in one of the area's most sought-after neighborhoods. Whether you're enjoying your morning coffee while watching the sunrise over the water, biking the nearby Legacy Trail, or spending the afternoon at Nokomis Beach, this exceptional home offers the very best of Florida living.
Listing Agent: Lori Lockhart, Pa (941-724-0595)
180 LOOKOUT POINT DR, OSPREY, FL 34229
$2,199,900216 Days on yellowkey MLS ID: A4672222
REDUCED by $50,000 (2.2%) on 06/03/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3236 Built: 1986Monthly Fee: $204 Tax: $8,750 (2024)Community: Southbay Yacht & Racquet ClubSpa: NoSingle Family
Taxes:$8,750
Tax Year: 2024
Remarks: Virtually Staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club with deep water marina and available boat slips, the opportunity to walk to your boat in a deep water marina with your home resting safely in Flood Zone X (where flood insurance is not even required by lenders) doesn't come along often. This is an extraordinary residence taken fully down to the studs and reimagined as a like-new, luxury smart home. Set on a .4-acre lot in Flood Zone X (no lender-required flood insurance), this never-lived-in five-bedroom, 3.5 bath, 3,236-square-foot home blends solid block construction with high-end design and cutting-edge technology. No detail was overlooked, including a standing seam metal roof, all new high-velocity impact windows, hurricane-rated garage doors and fully integrated Alexa features throughout. Wide-plank wood floors lead through a thoughtfully designed layout featuring custom built-ins including a kitchen desk, mudroom storage, dining room bar with wine refrigerator and living room shelving with glass doors. The kitchen is a showstopper with two large quartz islands, top-of-the-line Thermador appliances, a microwave drawer, concealed refrigerator, gas range with double ovens and a custom glass-door butler’s pantry. French doors at the entry feature Alexa-controlled electronic glass for your choice of instant privacy or transparent green views, while oversized sliders in the main living area fully retract for seamless indoor-outdoor living. The massive laundry room is a dream with two washers, two dryers, abundant storage and countertop space. Outside, enjoy a stunning new saltwater pool with cage, paver decking, and a state-of-the-art outdoor kitchen including storage and pullout drawer refrigerators, ideal for entertaining. The oversized garage offers excellent storage and the home’s elevation offers added peace of mind. Southbay is one of Sarasota County’s desirable waterfront communities with an updated clubhouse and fitness center overlooking the bay, complete with a ballroom, catering kitchen, meeting room and library. Community amenities also include a geothermal heated pool, children’s pool, tennis, pickleball, shuffleboard, basketball, kayak storage and a seven-acre deep-water marina accommodating boats up to 55 feet. Residents enjoy 20 acres of lush common grounds and five miles of walking trails, plus a vibrant calendar of social events. Near SR 681, with easy access to downtown Sarasota, Venice, beautiful beaches and A-rated schools including Laurel Nokomis, Sarasota Middle, Venice High, Pine View and the European Academy. This is a rare opportunity to own a turnkey, top-tier home in an unmatched boating community.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Katy Mcbrayer (941-400-2406)
401 N POINT RD #301, OSPREY, FL 34229
$475,000825 Days on yellowkey MLS ID: A4603773
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 is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
401 WALLS WAY, OSPREY, FL 34229
$1,775,000140 Days on yellowkey MLS ID: A4680312
1 Days Off yellowkey (back on 6/18/2026)
REDUCED by $25,000 (1.4%) on 05/31/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4387 Built: 1990Monthly Fee: $133 Tax: $16,158 (2025)Community: Oaks 2 Ph 1Single Family
Taxes:$16,158
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Perfectly positioned on the 9th hole tee box within the Oaks community, this meticulously appointed estate offers a rare opportunity for a premier Sarasota golf course lifestyle. Designed for the discerning enthusiast, the property features panoramic fairway views and western exposure for breathtaking sunsets. The interior is defined by soaring vaulted ceilings, refined crown molding, & finishes throughout. The heart of the home is a curated chef’s kitchen featuring a bespoke butcher block island, professional-grade Viking double ovens, and sleek quartz countertops. High-end functionality includes dual KitchenAid dishwashers and custom cabinetry. The primary living spaces flow seamlessly to a wet bar and wood-burning fireplace, ideal for post-round entertaining. An extraordinary floating staircase of hand-built Hungarian wood leads to a versatile upper level with a private balcony overlooking the course. The primary suite serves as a sanctuary, entered through exquisite hand-carved doors imported from Turkey. This retreat features French doors leading to a private courtyard, custom walk-in closets, and a whirlpool jacuzzi tub. Outdoor living is centered around the pool and an expansive lanai with a fully equipped summer kitchen. Notable infrastructure includes a 3-car garage, three AC units, and clear hurricane shutters. This residence offers an elevated Sarasota lifestyle with immediate proximity to world-class golf and the exclusive amenities of the Oaks community. Please note membership of The Oaks is required.
Listing is courtesy of: ENGEL + VOELKERS SARASOTA (941-388-9800)
Listing Agent: Andrea Stultz (941-929-6529)
1202 JESSIE HARBOR DR #1204, OSPREY, FL 34229
$599,00073 Days on yellowkey MLS ID: C7524397
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2006 Built: 2004Monthly Fee: $980 Tax: $6,502 (2025)Community: Blackburn Harbor Waterfront ViCondo
Taxes:$6,502
Remarks: Welcome home! This GULF ACCESS, WATERFRONT condo w/ AVAILABLE BOAT SLIPS BEHIND THE UNIT, in the highly sought-after Blackburn Harbor community is ready for its new owners. Offering over 2,000 SQFT, this beautifully updated 3 BED, 2.5 BATH residence with an ATTACHED 2 CAR GARAGE is ideally positioned as a SECOND-FLOOR, END UNIT at the END OF A CANAL—delivering unmatched PRIVACY, VAULTED ceilings, and MILLION DOLLAR WATER & SUNSET VIEWS that feel like a daily postcard. As an added bonus a NEW HVAC & HOT WATER HEATER were just installed! Lush tropical landscaping welcomes you to a private side entrance, while the building’s exclusive setting—just four units total—places you in one of the most desirable locations within the community. Perfectly situated at the edge of the MARINA, you are just STEPS from your BOAT, making it effortless to enjoy GULF ACCESS and endless days exploring nearby WATERWAYS, waterfront DINING, and hidden gems like Snake Island. Inside, this residence blends comfort and coastal elegance with a thoughtfully designed SPLIT FLOOR PLAN for ultimate privacy. The home features warm COASTAL decor, NEUTRAL PAINT, NEW KITCHEN APPLIANCES, GRANITE COUNTERTOPS, SOLID WOOD CABINETRY, custom light fixtures, and window treatments throughout. The open-concept living space flows seamlessly to a LARGE SCREENED LANAI overlooking the water, community park, and glowing SUNSET skies. FURNISHINGS ARE OPTIONAL. Set within a GATED, FINANCIALLY SOUND community spanning approximately 11 acres, residents enjoy an amenity-rich, resort-style lifestyle including a HEATED POOL, CLUBHOUSE, FITNESS ROOM, TENNIS & PICKLEBALL COURTS, KAYAK LAUNCH & STORAGE, BBQ GAZEBO, and scenic walking paths surrounded by lush Florida foliage. The vibrant social calendar offers something for everyone—water aerobics, monthly happy hours, bingo/game nights, pickleball club, book club, and more. Ideally located near US-41, this home offers convenient access to Nokomis Beach, Oscar Scherer State Park, the Legacy Trail, Downtown Venice, Downtown Sarasota, I-75, and Sarasota Memorial Hospital Venice Campus—placing the very best of Florida living right at your fingertips. Whether you're boating to the Gulf, enjoying sunset views from your lanai, or embracing the active waterfront lifestyle, this is truly the Florida Dream come to life. Schedule your private showing today! PLEASE CLICK ON THE VIDEO OF THE UNIT.
Listing is courtesy of: DOWNING FRYE REALTY, INC. (239-261-2244)
Listing Agent: Mackenzie Davis-Mahan (941-993-3272)
242 HIDDEN BAY DR #602, OSPREY, FL 34229
$700,000147 Days on yellowkey MLS ID: A4678883
REDUCED by $19,000 (2.6%) on 04/23/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1932 Built: 1999 Tax: $7,518 (2025)Community: Baypointe Vista 1Condo
Taxes:$7,518
Remarks: Penthouse Waterfront Residence | Enclosed Sunroom | Private Two-Car Garage | Optional Furnishings | Gated Bayfront Community This 6th-floor penthouse waterfront condominium at Hidden Bay offers unobstructed views of Little Sarasota Bay, the Intracoastal Waterway, and the Gulf beyond Casey Key. Designed to capture light and water views throughout the main living areas, the open floor plan features high ceilings, tall interior doors, and crown molding, creating a bright and welcoming coastal interior. The great room accommodates both living and dining areas and opens to an enclosed waterfront sunroom, an ideal space for morning coffee, sunset views, or quiet time overlooking the bay. The kitchen includes a counter-height breakfast bar, pantry storage, and an adjacent dining nook, offering both function and ease for everyday living or entertaining. A den provides flexible space for a home office or guest use. The primary suite features multiple closets and an en suite bath with dual vanities, a soaking tub, walk-in shower, water closet, and a dedicated makeup vanity area. A second bedroom includes an adjoining bath and walk-in closet. Luxury vinyl flooring has been added in the bedrooms and den. Laundry is located inside the residence. The condominium includes a private, fully enclosed two-car garage. Furnishings are included and may remain or be removed at the buyer’s preference. Hidden Bay is a gated waterfront community set along Little Sarasota Bay, offering a clubhouse with fitness center, heated pool and spa, tennis and pickleball courts, kayak storage and launch, and a boardwalk through mangroves leading to a fishing pier. Located west of US 41 in Osprey, Hidden Bay is conveniently positioned between Sarasota and Venice, with nearby access to shopping, dining, the Legacy Trail, and area beaches.
Listing is courtesy of: FIRST LIGHT REAL ESTATE (941-650-2256)
Listing Agent: Cathy Rustin (941-650-2256)
14401 MASTHEAD DR, OSPREY, FL 34229
$2,995,000106 Days on yellowkey MLS ID: A4684834
REDUCED by $155,000 (4.9%) on 06/12/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2665 Built: 2017Monthly Fee: $643 Tax: $874 (2025)Community: BaysideSpa: YesSingle Family
Taxes:$874
Remarks: Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the Bay and Intracoastal Waterway greet you upon entry, while the dramatic great room features a striking cupola with soaring 22-foot ceilings, wraparound windows, architectural beams, and detailed millwork that beautifully frame the waterfront setting. Pocketing impact sliders seamlessly open the living space to an expansive covered lanai where breathtaking sunsets, dolphins, and gentle coastal breezes create an unforgettable everyday backdrop. The open chef’s kitchen is designed for both entertaining and daily living, offering high end stainless appliances, a gas cooktop with pot filler, wine cooler, abundant cabinetry, and an oversized quartz island. Outdoor living shines with wood-paneled ceilings, crema pro leathered marble flooring, a gas fire pit, and a fully equipped outdoor kitchen with grill and beverage refrigerator. The solar and heat pump-heated saltwater lap pool and spa, outdoor shower, and private dock with lift complete the ultimate waterfront retreat. The primary suite enjoys beautiful water views and features a sitting area, double tray ceiling, dual custom walk-in closets, and a luxurious bath with double vanities and walk-in shower. Two additional en-suite bedrooms, a den or office, and a powder room provide comfort and flexibility. Wood-look tile flooring runs throughout, complemented by impact windows and doors, a smart-enabled security system, whole-home generator, and water conditioning system. Located just minutes from Casey Key, Nokomis Beach, Oscar Scherer State Park, and the Legacy Trail, this home offers effortless access to beaches, boating, dining, and recreation. An extraordinary waterfront residence where luxury, comfort, and coastal beauty come together, offering the lifestyle you’ve always imagined.
Listing Agent: Mackenzie Longueuil (941-961-4023)
89 NAVIGATION CIR, OSPREY, FL 34229
$345,00028 Days on yellowkey MLS ID: A4694435
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1449 Built: 2014 Tax: $3,931 (2025)Community: Bay Street VillageCondo
Taxes:$3,931
Remarks: Virtually Staged. Hidden within the gated community of Bay Street Village, this rarely available first-floor waterfront residence blends peaceful lakefront living with the convenience of Sarasota’s vibrant Gulf Coast lifestyle. From tranquil water views and warm Florida sunsets to nearby beaches, dining, shopping, and entertainment, this beautifully positioned condo creates the perfect balance of relaxation, comfort, and everyday convenience. From the moment you walk through the door, the tranquil pond views immediately draw your attention, creating a sense of calm that carries throughout the home. Imagine starting your mornings on the screened lanai with coffee in hand, overlooking the sparkling water feature while enjoying the warm Florida breeze and peaceful surroundings. With over 1,400 square feet of thoughtfully designed living space, this beautifully maintained 2-bedroom, 2-bathroom condo also features a versatile den, separate laundry room, and attached one-car garage. Rare first-floor units with water views and this level of convenience are highly desirable for full-time residents, seasonal owners, and investors alike. The open-concept floor plan was designed to maximize both comfort and entertaining. The kitchen showcases granite countertops, solid wood cabinetry, stainless steel appliances, stylish backsplash details, a spacious island, and breakfast bar seating that flows seamlessly into the bright and inviting living area. Crown molding, modern lighting, fresh neutral paint, and updated flooring throughout elevate the home with a clean and timeless feel. The spacious primary suite serves as a private retreat featuring peaceful water views, a large walk-in closet, linen closet, and an updated en-suite bathroom complete with dual sinks and a custom walk-in tile shower. A generously sized guest bedroom, beautiful guest bath, and flexible bonus room provide endless possibilities for guests, a home office, hobby space, or additional lounge area. Bay Street Village offers true maintenance-free living with resort-style amenities including a sparkling pool, fitness center, clubhouse, and beautifully maintained grounds. Centrally located between Sarasota and Venice, residents enjoy quick access to world-renowned Gulf beaches including, Nokomis Beach, and Venice Beach, along with downtown Sarasota, marinas, waterfront dining, shopping, golf, entertainment, Sarasota Bay, the Legacy Trail, and countless local restaurants and attractions. Located near the nationally recognized Pine View School and tucked away from the heavy tourist traffic while still remaining close to everything, this condo offers the perfect combination of convenience, comfort, and the relaxed coastal lifestyle that everyone dream about when moving to Florida. Whether you are searching for a primary residence, seasonal escape, or investment opportunity, this exceptional waterfront condo delivers location, lifestyle, and value all in one. Schedule your private showing today and experience firsthand why this hidden gem in Bay Street Village is the perfect place to call home.
Listing is courtesy of: KW COASTAL LIVING II (941-556-0500)
Listing Agent: Jozefina Wells (941-993-3051)
173 NAVIGATION CIR #107, OSPREY, FL 34229
$328,0004 Days on yellowkey MLS ID: N6144704
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1528 Built: 2015 Tax: $2,892 (2025)Community: Bay Street VillageCondo
Taxes:$2,892
Remarks: Immaculate and lightly lived-in 3BR/2BA condo in the gated community of Bay Street Village, offering beautiful water views with a fountain from the main living areas, the primary suite, and the screened lanai. The popular Ibis floor plan features an open-concept kitchen, dining, and great room with 42" upper cabinets, granite countertops, a custom tile backsplash, and stainless-steel appliances. The designer-level, fully customized laundry room includes soft-close custom cabinets, a laundry sink, a custom backsplash, and a stacking washer and dryer, providing exceptional storage and functionality. The primary suite offers a water view, a barn-door entry to the bath, a custom frameless glass shower enclosure with stone flooring, a linen closet, custom closet organizers, and a designer ceiling fan with light. Bedroom two also features custom closet organizers, while bedrooms two and three include custom ceiling fans. Ceiling fans are additionally installed in the great room and the lanai for enhanced comfort. Plantation shutters are installed in the entry foyer, primary bedroom, bedrooms 2 and 3, and the family room, adding style, privacy, and a cohesive look throughout the home. Additional upgrades include upgraded carpet on the stairs and in the primary bedroom, keyless front-door entry, keyless man-door entry, and an exterior garage door keypad. Quality construction provides peace of mind with hurricane-impact windows and doors, concrete block construction, a tile roof, and a paver driveway. The monthly condo fee covers water, sewer, exterior maintenance, landscaping, gated entry, a heated resort-style pool, cabana, fitness center, and clubhouse. No CDD fees. Ideally located near Nokomis Beach, Casey Key, Siesta Key, the Legacy Trail, Oscar Scherer Park, Sarasota and Venice shopping and dining, 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)
5100 JESSIE HARBOR DR #304, OSPREY, FL 34229
$725,00058 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 Agent: Suki Scollo (941-587-2289)
4428 CONCHFISH LN, OSPREY, FL 34229
$548,000366 Days on yellowkey MLS ID: A4656074
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1861 Built: 2018Monthly Fee: $147 Tax: $5,936 (2024)Community: Palms/Casey KeySpa: NoSingle Family
Taxes:$5,936
Remarks: 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!
Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)
Listing Agent: Mariana Georgieva (941-809-0416)
4271 EXPEDITION WAY #103, OSPREY, FL 34229
$270,00070 Days on yellowkey MLS ID: A4689541
REDUCED by $10,000 (3.6%) on 06/04/2026
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: 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. **SELLER FINANCING AVAILABLE** **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)
408 PARK TRACE BLVD, OSPREY, FL 34229
$595,000106 Days on yellowkey MLS ID: A4685004
2 Days Off yellowkey (back on 6/16/2026)
REDUCED by $20,000 (3.3%) on 06/01/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 2003Monthly Fee: $54 Tax: $4,652 (2025)Community: Park Trace EstatesSingle Family
Taxes:$4,652
Remarks: Under contract-accepting backup offers. Welcome to your own private oasis in Park Trace Estates, a stunning 3-bedroom, 3-bath single-family home overlooking water with unobstructed views of the Legacy Trail and Oscar Scherer State Park. Located in a desirable community minutes from Pine View School, healthcare, and beaches, this residence is perfectly designed for indoor-outdoor living. The heart of the home is a beautiful central courtyard with a heated saltwater pool with a FastLane system, around which the main living spaces are thoughtfully arranged. An en-suite guest bedroom with private courtyard access provides a secluded retreat perfect for visitors. The open-concept interior flows seamlessly from the kitchen, complete with a signature royal blue Hestan refrigerator, into an inviting living room ideal for entertaining. From there, step out to a screened patio overlooking the water to relax in total comfort. The spacious master suite features dual California Closets, a luxurious remodeled bathroom, and an adjoining room that serves as a private office or reading nook. Throughout the home, plantation shutters provide elegant light control and privacy. The property is finished with a side-entry two-car garage featuring custom California Closets storage and a Tesla charger. Positioned just steps from the pristine Legacy Trail for biking and recreation, this home provides the perfect combination of style and lifestyle. Home is available fully furnished. The home is exceptionally well-maintained, featuring a high-efficiency HVAC system (New AC 2017/Air Handler 2020) with a programmable thermostat, a central vacuum system, and an artistic hidden TV in the living room. Recent kitchen and laundry upgrades include a 2018 washer and dryer alongside newer appliances (2020–2022). The private courtyard is equally impressive, boasting a new pool screen (2022), new pool equipment (2024), and an Endless Pool Fastlane feature for a premium fitness experience. Property is located in Flood Zone X (flood insurance generally not required).
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Jennie Lascelle (941-504-0102)
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