Displaying: For Sale
Location: Osprey
Property Type(s): Single Family
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Osprey - 76 properties found
1527 BUOY LN, OSPREY, FL 34229
$1,165,00077 Days on yellowkey MLS ID: A4688266
REDUCED by $34,000 (2.8%) on 06/23/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2830 Built: 1989Monthly Fee: $204 Tax: $8,555 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,555
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Venice Area Middle
Remarks: Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2026 AC unit, 2024 tile roof, 2023 driveway, cabinets, lighting, appliances, tile and carpet are just the beginning. 2023 pool and spa led lighting, Pentair controller, saltwater conversion, and owned 250 gallon propane. Dry bar with ice maker, wine fridge, and beverage fridge. Large covered outdoor living space overlooking the large lanai with tv, private tanning area, and room to entertain. A split bedroom design, game room with space for billiards table, and separate dining area, and great room surround the private courtyard layout designed to entertain. Ample storage throughout including an air conditioned, secure 12x7 storeroom. Southbay Yacht and Racquet Club offers a clubhouse, tennis, pickleball, basketball, shuffleboard, playground, and low fee, exclusive dockage for residents in the deep water marina. Frequent community activities provide opportunities for an active social atmosphere from cruises to sports.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Matthew Lewis (651-746-4100)
353 S SHORE DR, OSPREY, FL 34229
$999,00083 Days on yellowkey MLS ID: A4688006
REDUCED by $26,000 (2.5%) on 06/09/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 1968Monthly Fee: $11 Tax: $3,904 (2025)Community: Sorrento Shores Rep Of 2Spa: NoSingle Family
Taxes:$3,904
Middle School: Laurel Nokomis Middle
Remarks: Calling all WATER enthusiasts! BOATERS DREAM IN SORRENTO SHORES! Just FOUR houses from the Intracoastal Waterway with NO bridges to the Gulf, this beautifully updated waterfront pool home delivers the lifestyle buyers come to Florida searching for. Welcome to Sorrento Shores — a hidden gem perfectly positioned between Venice Island and Siesta Key, where every day feels like a vacation. Situated on an oversized canal-front lot, this move-in ready 3-bedroom, 2-bath home offers quick deep-water access to the Intracoastal and Gulf beyond. Bring your boat, your paddleboards, your fishing gear, and start living the coastal lifestyle immediately. This home is Offered TURNKEY (minus select personal items), has a Private dock with quick open-water access, a 27x40 screened lanai with resurfaced pool for plenty of lazy pool days, and sits on an Oversized .36-acre lot. No need to store your boat trailer off site, there is ample parking for your boat trailer right on your own property. No CDD fees + voluntary HOA only $130/year And the Big-Ticket items have been taken care of: NEW ROOF 2025, NEW SEPTIC SYSTEM 2024, NEW POOL CAGE 2025 SEWER PIPES RELINED 2023-2024, IMPACT WINDOWS 2018, NEW POOL HEATER 2025, NEW WATER HEATER 2024 Newer A/C 2018 Updated baths + fresh interior finishes 2025 Cruise by boat to Casey Key Fish House, Pops Sunset Grill, Snake Island, Midnight Pass, Venice waterfront restaurants, and the Gulf of Mexico — all from your own backyard. This is not just a home… It’s the waterfront lifestyle buyers dream about!
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Phyllis Coviello (941-408-3265)
472 PARK TRACE BLVD, OSPREY, FL 34229
$599,000144 Days on yellowkey MLS ID: A4680326
REDUCED by $10,000 (1.6%) on 06/23/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2217 Built: 2002Monthly Fee: $58 Tax: $5,925 (2025)Community: Park Trace EstatesSingle Family
Taxes:$5,925
Remarks: Located in the highly desired Park Trace Estates, this beautifully maintained 4-bedroom pool home sits on a premium corner lot and is truly move-in ready. Recent upgrades include a NEW TILE ROOF and IMPACT WINDOWS, offering peace of mind and energy efficiency. The entire house has a LEAFHOME WATER FILTRATION SYSTEM, ensuring clean, high-quality water throughout. The spacious layout is perfect for both everyday living and entertaining, with seamless indoor-outdoor flow to the private SALT WATER POOL. Enjoy mature landscaping on the large corner lot providing added space and privacy, with plenty of room to enjoy the beautiful surroundings. Park Trace Estates has low HOA fees, and is in a prime location close to top-rated schools, shopping, restaurants, Legacy Trail, Oscar Scherer State Park, and Gulf Coast beaches.
Listing is courtesy of: SUNDANCE REAL ESTATE SERVICES (941-780-6710)
Listing Agent: Damon Zuchelli (941-448-5686)
347 BAYSHORE DR, OSPREY, FL 34229
$739,00042 Days on yellowkey MLS ID: A4693374
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2216 Built: 2013 Tax: $879 (2025)Community: Bay Acres - ResubSingle Family
Taxes:$879
Elementary School: None
High School: None
Middle School: None
Remarks: This custom built home is located in the Osprey subdivision Bay Acres, an established neighborhood along Little Sarasota Bay between Sarasota and Venice. It's location allows easy access to I-75, top rated schools to include the magnet school Pine View , and Nokomis and Siesta Beaches, and all amenities of both cities. This home includes over 4000 sq ft of total space that includes a 2 plus car garage with over 1400 sqft of space- part of the garage having a large open area previously used as a hobby room that can be converted to an area to meet your needs. The interior of the home has many nice features including a very nice large kitchen , dining room with tray ceilings, floors are gorgeous-real hardwood and wide planked. This well built home has impact windows, a metal roof, a large covered porch and fenced yard. Thsi small waterfront community will allow you to keep your Boat/Trailer or RV on your property. Bay Acres also has some boat slips and Kayak storage for a small fee. You can be out in Gulf waters in minutes. Around the corner is Blackburn Point Boat Ramp, and many waterfront restaurants. Come see why this friendly neighborhood and home can make your dreams a reality.
Listing is courtesy of: COLDWELL BANKER REALTY (941-739-6777)
Listing Agent: Sharon Sprow (813-817-9931)
816 SHADOW BAY WAY, OSPREY, FL 34229
$655,00042 Days on yellowkey MLS ID: A4690226
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2251 Built: 1998Monthly Fee: $120 Tax: $4,453 (2025)Community: RivendellSpa: NoSingle Family
Taxes:$4,453
Remarks: Set within Rivendell's 400 acres of lakes, preserves, and open spaces, this Osprey pool home checks the boxes buyers rarely find together: a quiet, established neighborhood, a long list of owner-completed upgrades, and no CDD fees. If you're looking for a move-in-ready foundation you can personalize over time, this one deserves a look. Major upgrades include: • NEW ROOF and GARAGE DOOR (2023) • NEW A/C (2021) • New dishwasher and garbage disposal (2020) • New pool pump (2017) • Irrigation well deepened (2016) • New pool cage (2015) • Replumbed (2012) Additional features include a portable generator that conveys with the sale. Inside, high ceilings and abundant natural light create an airy atmosphere throughout. Granite countertops in the kitchen and all bathrooms. The split floor plan separates the primary suite from guest bedrooms, while the main living areas open through sliding glass doors to the covered lanai and private pool, an ideal setup for entertaining or everyday Florida living. The generous 3-car garage adds flexibility for storage, hobbies, or workspace. Rivendell is known for its scenic preserve setting, walking trails, heated community pool, and peaceful park-like atmosphere. Residents enjoy convenient access to the Legacy Trail, Oscar Scherer State Park, Nokomis Beach, Siesta Key Beach, shopping, dining, and everyday conveniences along US-41. Approximately 1 mile from Pine View School, consistently ranked among the top public schools in the nation. Low HOA fees, no CDD fees, and a location close to beaches, nature, and everyday conveniences make this a rare find in one of Osprey's most established communities.
Listing Agent: Katrin Pfitzenreiter (917-543-8560)
433 E MACEWEN DR, OSPREY, FL 34229
$2,189,000175 Days on yellowkey MLS ID: A4676505
REDUCED by $61,000 (2.7%) on 06/23/2026
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.
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
25 SUGAR MILL DR, OSPREY, FL 34229
$1,489,000152 Days on yellowkey MLS ID: A4678423
0 Days Off yellowkey (back on 6/22/2026)
REDUCED by $61,000 (3.9%) on 06/04/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3066 Built: 1998Monthly Fee: $483 Tax: $7,845 (2025)Community: OaksSpa: NoSingle Family
Taxes:$7,845
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE VIEWS. Located in Flood Zone “X” (no flood insurance required), the home is tucked behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. The home offers 3 En Suite Bedrooms, 3 Full and 1 Half Baths. The Updated Kitchen features Quartz countertops, custom hardwood cabinetry, and premium appliances, including Sub-Zero and Wolf. A cozy family room with a wood-burning fireplace provides an inviting gathering space, while impressive Brazilian cherry hardwood flooring enhances the living and dining areas. The spacious primary suite includes a walk-in closet and a luxurious bath with dual vanities, a custom-tiled shower, and a soaking tub. Outdoor living is highlighted by a large screened and covered entertaining area, along with a stunning open-air pool overlooking the tranquil preserve. Additional features include a circular driveway and a peaceful, private setting. RECENT UPDATES include Hurricane IMPACT Windows (2019), HVAC (2021), ROOF (2014), Flooring (2020), Etc. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**
401 WALLS WAY, OSPREY, FL 34229
$1,775,000144 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
Remarks: Under contract-accepting backup offers. 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)
4424 CONCHFISH LN, OSPREY, FL 34229
$585,00034 Days on yellowkey MLS ID: A4691622
REDUCED by $30,000 (4.9%) on 06/07/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2370 Built: 2017Monthly Fee: $125 Tax: $4,467 (2026)Community: Palms/Casey KeySpa: YesSingle Family
Taxes:$4,467
Tax Year: 2026
Remarks: Situated in the highly sought-after community of Palms at Casey Key, this beautifully maintained 2017-built home offers the perfect blend of comfort, style, and location. With low HOA fees and no CDD fees, this property delivers exceptional value in one of Osprey’s most desirable areas. From the moment you arrive, the paver driveway and lush tropical landscaping create a warm and welcoming first impression. Inside, the home opens to a bright and airy great room where tray ceilings and expansive triple-panel sliding glass doors allow natural light to pour in, creating an effortless connection between indoor and outdoor living. Designed with both everyday living and entertaining in mind, the kitchen serves as the heart of the home with a large center island offering ample seating, white cabinetry, stainless steel appliances, and a spacious corner pantry for additional storage. The thoughtfully designed split-bedroom floor plan offers privacy and comfort, while the owner’s suite feels like a relaxing retreat with tray ceilings, a large walk-in closet, dual vanities, and a walk-in glass shower. Step outside to your private patio overlooking the in-ground spa — the perfect place to unwind after a beach day, enjoy a quiet evening under the stars, or cool off during warm Florida afternoons. Location is everything, and this home truly delivers. Ideally situated just minutes from nationally ranked Pine View School, less than a mile from the Casey Key boat launch and waterfront tiki bar, and only about 15 minutes to both Nokomis Beach and Siesta Key Beach, you’ll enjoy easy access to some of the area’s best boating, dining, shopping, golf, parks, and coastal lifestyle amenities. Whether you're looking for a full-time residence or the perfect Florida retreat, this home offers the lifestyle so many buyers are searching for.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Ashley Wallace (941-302-2586)
1474 LANDVIEW LN, OSPREY, FL 34229
$1,475,00010 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 at 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)
314 S SHORE DR, OSPREY, FL 34229
$1,495,00029 Days on yellowkey MLS ID: TB8510971
REDUCED by $154,000 (9.3%) on 06/01/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3853 Built: 1981Monthly Fee: $15 Tax: $8,819 (2025)Community: Sorrento Shores Unit 1Spa: NoSingle Family
Taxes:$8,819
Remarks: Rare Gulf-access waterfront opportunity in desirable Sorrento Shores in Osprey. This spacious residence is set on a generous 0.54-acre waterfront lot with a private dock, screened pool, outdoor kitchen/grill area, paver patio, mature landscaping, and peaceful canal views. The home offers 3 bedrooms, 3 full baths, 3,853 sq ft, and a large flex room currently used as a studio with possible 4th bedroom potential. The open ranch-style layout includes comfortable living, dining, and entertaining spaces filled with natural light. The updated kitchen and bar area feature Viking Professional double ovens, a Viking Professional gas stove, Sub-Zero refrigerator, newer dishwasher, and microwave. Additional spaces include a private office with built-in cabinetry, large flex room, and an air-conditioned tackle/hobby/storage room with an additional Sub-Zero refrigerator. Major system updates noted by seller include a newer roof, full-house generator, impact windows and doors, two AC systems, new central vacuum system, tankless water heater, fireplace, and propane service for the grill, stove, dryer, fireplace, tankless water heater, and full house generator. Located near Casey Key, Nokomis Beach, Venice, Sarasota, marinas, dining, shopping, golf, parks, and coastal amenities.
Listing is courtesy of: HOMECOIN.COM (888-400-2513)
Listing Agent: Jonathan Minerick (888-400-2513)
180 LOOKOUT POINT DR, OSPREY, FL 34229
$2,199,900220 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)
113 BURNEY RD, OSPREY, FL 34229
$999,50061 Days on yellowkey MLS ID: A4690672
0 Days Off yellowkey (back on 6/20/2026)
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: Under contract-accepting backup offers. **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**
97 SUGAR MILL DR, OSPREY, FL 34229
$1,950,00053 Days on yellowkey MLS ID: A4691789
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4885 Built: 1990Monthly Fee: $483 Tax: $16,651 (2025)Community: OaksSingle Family
Taxes:$16,651
Remarks: Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed floor plan with expansive living areas, soaring ceilings, and an abundance of natural light. At the heart of the home is a completely renovated chef’s kitchen, featuring high-end finishes, premium appliances, custom cabinetry, and a seamless flow into the main living and entertaining spaces, perfect for both everyday living and hosting guests in style. Each of the five spacious bedrooms offers comfort and privacy, while the six bathrooms provide ample convenience for family and guests. Recent updates include a brand-new roof, and renovated kitchen, offering peace of mind and long-term value for the next owner. Outdoor living is equally impressive, with tranquil surroundings that capture the essence of Florida living, ideal for relaxing, entertaining, or simply enjoying the natural beauty that defines The Oaks Bayside. Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility. Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.
Listing is courtesy of: PALM PARADISE REALTY GROUP (239-955-7256)
Listing Agent: Maria Domenech (978-204-3219)
730 FORDINGBRIDGE WAY, OSPREY, FL 34229
$710,0004 Days on yellowkey 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
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)
619 OAK RIVER CT, OSPREY, FL 34229
$609,90040 Days on yellowkey MLS ID: A4692331
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2047 Built: 1997Monthly Fee: $25 Tax: $5,484 (2025)Community: Bay Oaks EstatesSpa: NoSingle Family
Taxes:$5,484
Remarks: Virtually Staged. Back on the market due to buyer financing. Move-in ready Bay Oaks pool home featuring a beautifully renovated kitchen, stunning spa-inspired primary bath, updated flooring, and a huge private fenced backyard. Situated on an oversized 0.38-acre corner lot, this home offers the perfect combination of modern updates, privacy, and outdoor living. Welcome to this thoughtfully renovated pool home in sought-after Bay Oaks Estates, perfectly positioned on an oversized 0.38-acre corner lot in the heart of Osprey. Featuring 3 bedrooms plus a dedicated office, 10-foot ceilings, a huge fenced backyard, and extensive modern updates throughout, this move-in-ready residence offers a rare blend of style, comfort, and effortless indoor-outdoor living. One of the home’s standout features is the oversized fenced backyard, offering a rare combination of space, privacy, and flexibility. The screened lanai, private pool, and expansive outdoor area create the perfect setting for entertaining and year-round enjoyment. Framed by mature landscaping and a newer concrete tile roof (2021), the home creates a welcoming first impression from the moment you arrive. A large driveway and covered parking area provide abundant convenience. New flooring throughout (2025), brand new electrical panel, updated lighting, fresh interior paint, and carefully selected finishes create a clean, cohesive modern aesthetic rarely found in the neighborhood. Inside — 10-foot ceilings, abundant natural light, and a thoughtfully designed layout create an elevated sense of space and openness. Smart-home features include an ecobee thermostat, keypad entry, and a Samsung all-in-one smart washer and dryer. At the center of the home, the fully remodeled kitchen combines style and function with granite countertops, white shaker cabinetry, stainless steel appliances, modern finishes, and an expansive breakfast bar that opens seamlessly to the main living areas. The spacious primary suite serves as a true retreat with two walk-in closets and a beautifully remodeled bath featuring quartz countertops, dual vanities, a freestanding soaking tub, and a frameless glass walk-in shower. Perfectly positioned between The Oaks Club and Stoneybrook Golf & Country Club, Bay Oaks offers the feel of luxury golf-course living without the fees. Families will especially appreciate being just 3 miles from Pine View School, consistently ranked among the top public schools in the nation. Just 6 miles from Siesta Key and 4 miles from Casey Key, this prime Osprey location places you near marinas, golf courses, the Legacy Trail, shopping, dining, and Sarasota’s coastal lifestyle.
Listing is courtesy of: FISHMAN GROUP REALTY LLC (763-443-1761)
Listing Agent: Ross Fishman (763-443-1761)
557 CRANE PRAIRIE WAY, OSPREY, FL 34229
$599,00011 Days on yellowkey MLS ID: A4696823
0 Days Off yellowkey (back on 6/19/2026)
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: Under contract-accepting backup offers. 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)
14401 MASTHEAD DR, OSPREY, FL 34229
$2,995,000110 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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Mackenzie Longueuil (941-961-4023)
4428 CONCHFISH LN, OSPREY, FL 34229
$548,000370 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)
408 PARK TRACE BLVD, OSPREY, FL 34229
$595,000110 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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