Displaying: For Sale
Location: Osprey
Property Type(s): Single Family
Living Area Square Feet: 2500 to 2999
Do Not Show Listings
Osprey - 18 properties found
919 TRANQUILITY CIRCLE CIR, OSPREY, FL 34229
$794,000106 Days on yellowkey MLS ID: A4678841
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2854 Built: 2001Monthly Fee: $158 Tax: $6,368 (2025)Community: North Creek EstsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,368
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: *BRAND NEW BARREL TILE ROOF (APRIL 2026)* WOW! AND A TOTAL OF 55,000 PRICE ADJUSTMENT! RARE OPPORTUNITY to own this stunning former John Cannon model home on peaceful Tranquility Circle . This pristine 4BR/3.5BA pool home is a kayaker and nature lover’s paradise on North Creek with direct access to Little Sarasota Bay via Kayak or Canoe offering abundant wildlife and serene water views. Enjoy your own "Selby Garden" like setting .So hard to find such a private lot with this level of privacy so close to everything. Enjoy an open, spacious split-plan layout with Four bedrooms, formal and casual living spaces, and an open kitchen with granite countertops, island, and gas range—perfect for entertaining. The great room and lanai seamlessly connect to the sparkling pool, creating a private retreat with creek views. The luxurious Primary suite is a true getaway, featuring bay windows, his-and-hers closets, Expansive Primary Bath with dual water closets, soaking tub, separate shower and dual vanities. Interior upgrades include tile flooring, crown molding, 8-foot doors, designer lighting, and ceiling fans. Recent and notable upgrades: pool resurfaced (2023), pool cage replaced/rescreened (2018), A/C units (2020 & 2024), water heaters (2022/2023), new gutters & guards, paver driveway and pool deck, rimless shower doors, new front door, new refrigerator, new flooring in all bedrooms and closets, upgraded drainage system, and more. Prime location near the Legacy Bike Trail, YMCA, Oscar Scherer Park, The Oaks, Palmer Ranch, Sarasota Square Mall, and minutes to Sarasota, Venice, and Gulf Coast beaches. A-rated schools, including top-ranked Pine View School, make this property ideal for families. A rare, meticulously maintained home with exceptional upgrades, This property must be seen to fully appreciate its value and beauty. * Please be sure to watch Virtual Tours also. The Matterport will immerse you within the property as if you were doing a walk through*.
Listing is courtesy of: TIDELINE REAL ESTATE BROKERS (941-587-1669)
Listing Agent: Ann Winger (941-228-2811)
408 YACHT HARBOR DR, OSPREY, FL 34229
$1,375,0007 Days on yellowkey MLS ID: A4691576
0 Days Off yellowkey (back on 4/28/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2624 Built: 1976Monthly Fee: $219 Tax: $9,482 (2025)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$9,482
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Renovated throughout, this stunning four-bedroom, four-bath residence is in one of the West Coast of Florida's premier marina communities, Southbay Yacht and Racquet Club. This sought-after waterfront community features a community-owned marina with 172 boat slips accommodating vessels up to 55 feet, all within a protected deep-water basin. Enjoy low quarterly HOA fees, $656, for a resort-style atmosphere. This home features a beautifully updated chef's kitchen with a gas cooktop, double ovens and a large island with ample seating. A spacious dining room and wet bar provide an ideal setting for gatherings, while the split bedroom floor plan offers privacy for family and guests. Recent upgrades include a newer roof, hurricane-rated windows, appliances and updated plumbing and electrical. Osprey is between Sarasota and Venice, just 20 minutes to the famous Siesta Key Beach. A quarter mile away, the Legacy Trail offers miles of scenic biking and walking paths, along with easy access to Oscar Scherer State Park. The area has an abundance of waterfront dining options and shopping just a walk or golf cart ride away. Osprey is home to Pine View School for the gifted, consistently ranked the number one school in Florida and among the top in the nation.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Thomas Netzel (941-539-0633)
14401 MASTHEAD DR, OSPREY, FL 34229
$3,150,00061 Days on yellowkey MLS ID: A4684834
REDUCED by $100,000 (3.1%) on 05/01/2026
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
Middle School: Sarasota Middle
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)
664 CRANE PRAIRIE WAY, OSPREY, FL 34229
$887,00074 Days on yellowkey MLS ID: A4681662
REDUCED by $10,000 (1.1%) on 04/08/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2870 Built: 2003Monthly Fee: $437 Tax: $5,460 (2025)Community: Willowbend Ph 2Spa: YesSingle Family
Taxes:$5,460
Remarks: It’s always about the view and the new tile roof December 2025. This stunning waterfront home in Willowbend, bordering community greenbelt with views to Oscar Scherer State Park, is a luxurious Lee Wetherington-built Paloma floorplan designed to the highest standards, offering spectacular views and seamless indoor-outdoor living. On one of the community’s most desirable lots, it features unobstructed shimmering views of a wide lake and the natural beauty of the park, creating an extraordinary backdrop for an exceptional lifestyle. The idyllic setting includes a sparkling heated pool and spa. Summer kitchen has sink and stainless beverage refrigerator with large bar entertaining area. The exterior boasts a three-car garage and a double-door that welcomes you into an inviting, spacious interior. The home’s open floor plan includes living/dining with views to the natural beauty, tile on diagonal, crown molding and vaulted ceilings. Handsome office/den to the front of residence. The gourmet kitchen is equipped with granite countertops, stainless steel appliances, including built-in gas range and custom hood. Large walk-in pantry with oversized adjacent laundry room that has an additional deep closet. Dinette area features an aquarium window to take in the natural beauty. Family room is spacious with a corner pocket door that opens wide to let in Florida’s finest weather. The primary suite offers bamboo wood floors, double-tray ceiling and sitting area with French doors. California-style walk-in closets and a luxurious bath with dual sinks, a tub, walk-in shower and separate toilet. Each guest bedroom is generous in size with full bath in between. Additionally, it is a bonus living space with wood floors overlooking the serene setting. Third bath serves as pool bath. On a practical note, new water heater in 2026 and pool pump in December 2025. An amazing lifestyle awaits, all overlooking serene waterfront views teeming with wildlife such as eagles, osprey, otters, turtles and deer. The home is ideally near downtown Venice, Sarasota, Siesta Key, Nokomis Beach and Legacy Trail, offering easy access to cultural attractions, shopping, dining and recreational activities. Short distance to nationally ranked Pine View School. The community’s low fees include internet, Direct TV streaming, yard maintenance, irrigation, pool and spa, gym and pickleball, making this a harmony of luxury, comfort and stunning beauty.
Listing Agent: Todd Currey (941-402-6000)
17 BAYHEAD LN, OSPREY, FL 34229
$1,295,000113 Days on yellowkey MLS ID: A4676710
REDUCED by $5,000 (0.4%) on 04/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2850 Built: 1992Monthly Fee: $458 Tax: $6,642 (2024)Community: Bishops Court At Oaks PreserveSingle Family
Taxes:$6,642
Elementary School: Gulf Gate Elementary
High School: Riverview High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: Impeccable is the only way to describe this charming, completely remodeled 3-bedroom, 2-bath residence that blends luxury with everyday comfort. No detail was overlooked in the renovation, resulting in a truly beautiful and thoughtfully designed home. The interior showcases high-end finishes throughout, including wood-look tile flooring, quartzite countertops, a stylish coffee bar, and a custom hood vent. The former Florida room has been transformed into a spacious family room, perfect for entertaining, while one of the three bedrooms is currently utilized as a home office. Outdoor living shines with a newly added side deck featuring a canopy for shaded dining, a swinging chair, grill space, and a relaxing hot tub. The home sits on the largest lot in the neighborhood, offering a generous yard and a picturesque pond view as the ultimate backdrop. Residents enjoy access to a community pool and clubhouse just a short walk away, with landscape maintenance included for truly low-maintenance living. This exceptional home is a prime location for the ultimate country club lifestyle. Membership in The Oaks Club is required. The Oaks Club, Sarasota’s premiere golf and country club, has two champion 18-hole golf courses, twelve HAR-TRU tennis courts (4 lighted), four pickleball courts, an over 7,500 square foot state-of-the-art WellFit Center, an award-winning culinary team, and robust activities and social calendars. Club membership is required with homeownership.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
759 FORDINGBRIDGE WAY, OSPREY, FL 34229
$727,00019 Days on yellowkey MLS ID: O6399774
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2950 Built: 2002Monthly Fee: $55 Tax: $7,129 (2025)Community: Rivendell WoodlandsSingle Family
Taxes:$7,129
Remarks: Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layout, this residence boasts elegant finishes and ample natural light throughout. The modern kitchen is equipped with top-of-the-line appliances and give plenty of storage space. Enjoy the serene outdoor area with a beautifully landscaped yard, appropriate for relaxation and entertainment. Situated in a desirable neighborhood, this property provides easy access to Pineview Gifted School. Don't miss this exceptional opportunity to own this beautiful marvelous 4 bedrooms with a dent and 3 and 1/2 baths opportunity. The circle pool is beautiful and you can see it in Dinnig Room. The master bedroom is spacious with the beautiful marble Venetian team. There are 2 medium room next door. The washer and dryer are new in the laundry room. All the bathrooms are newly installed marble and high luxury tiles. The floor is beautiful with fancy travertine tiles for the whole downstairs floor and the upstairs are high end luxury plank vinyl all new floors and bathrooms
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
104 PARK TRACE BLVD, OSPREY, FL 34229
$575,000148 Days on yellowkey MLS ID: A4674221
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2557 Built: 2002Monthly Fee: $58 Tax: $7,427 (2024)Community: Park Trace EstatesSpa: NoSingle Family
Taxes:$7,427
Remarks: Welcome to this elegant and spacious luxury pool home offering over 2,500 square feet of refined living in one of the most desirable communities along the Gulf Coast. With a freshly painted exterior, stunning hardwood floors throughout, and an exceptional layout designed for both comfort and style, this residence is move-in ready and perfectly suited for modern living. Boasting four bedrooms, including a private guest suite area, and three beautifully appointed baths, the home offers flexible space ideal for hosting family and friends. Expansive living areas flow seamlessly to the outdoor oasis, where a sparkling pool creates the perfect backdrop for relaxing or entertaining in the Florida sunshine. Just 10 miles south of downtown Sarasota and 6 miles north of Venice, Park Trace Estates provides the best of both worlds: tranquil suburban living with unbeatable convenience. Outdoor enthusiasts will love being only one block from the Legacy Trail, offering miles of scenic pathways for biking, running, and recreation. Nature and waterfront activities abound with Oscar Scherer State Park, Bay Street Park, Nokomis Beach, Siesta Key Beach, Gulf Harbor Marina, and Blackburn Point Park all within close reach. Families will appreciate access to top-rated schools, including the prestigious Pine View School, known for its exceptional academic programs. Offering a rare blend of luxury, comfort, and prime location, this Park Trace Estates home is a true Sarasota-area gem, ready to welcome you to the lifestyle you’ve been dreaming of.
Listing Agent: Lisa Morreale (941-400-9038)
403 LONGBOW TRL, OSPREY, FL 34229
$1,095,000169 Days on yellowkey MLS ID: A4672081
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2770 Built: 1978Monthly Fee: $42 Tax: $9,020 (2024)Community: Pine RanchSingle Family
Taxes:$9,020
Remarks: Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in one of Osprey's most desirable communities Pine Ranch. Located 15 minutes from Siesta Key and Nokomis Beach and is within a short distance from the nationally top-rated Pine View School, #1 High School in Florida and the natural beauty of the Legacy Trail. This charming home offers a perfect blend of comfort, style, and Florida living. Step inside to find a bright, open interior with plenty of natural light, spacious living area, and a seamless connection between indoor and outdoor living. A newly remodeled kitchen with ample cabinetry and a seamless flow for entertaining. The primary suite provides a peaceful retreat with generous closet space and an en-suite bath and balcony with stunning views. Additional bedrooms are well-sized, making this home ideal for guests or a growing household. Enjoy Florida living at its best with an inviting private backyard inground pool framed by mature landscaping perfect for relaxing, gardening, or creating your own outdoor oasis. The backyard showcases a picturesque large pond, with a deck, making it an ideal spot for relaxing evenings. Additionally, this property features an in-law suite with one bedroom and one bathroom, ideal for guests or extended family. Whether you're seeking a full-time residence or a seasonal getaway, this Osprey gem delivers comfort, location, and value. With its prime Osprey location, easy access to Sarasota and Venice, and the natural beauty of the Gulf Coast just minutes away, this home offers exceptional value and an unbeatable lifestyle. A wonderful opportunity to own in one of Sarasota County's most desirable communities don't miss your chance to make 403 Longbow Trail your next home.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Edward Bieker, Pa (941-525-6473)
678 FAITH AVE, OSPREY, FL 34229
$775,000145 Days on yellowkey MLS ID: A4674865
Bed: 3 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 2583 Built: 1995 Tax: $5,871 (2025)Community: Trinity AcresSingle Family
Taxes:$5,871
Elementary School: Pine View School
Middle School: Pine View School
Remarks: Private Key West–style retreat on 2.53 wooded acres in Osprey. Rarely does a property of this size become available in such a convenient location—just minutes from Pine View School, shopping, restaurants, and the Intracoastal Waterway—yet offering the privacy and space of a true country setting. This combination of acreage and accessibility makes the home exceptionally unique for the area. A generous 37x60 paver-brick patio surrounds the screened lap-style pool, now protected by a freshly updated pool cage. Multiple French doors open to wide second-floor decks overlooking the peaceful wooded backdrop. A recently added metal roof enhances durability, longevity, and value. Inside, the home features oak hardwood floors, vaulted tongue-and-groove cypress ceilings, and a striking wood-burning fireplace that add warmth and character throughout. The kitchen and baths retain their classic charm and present an excellent opportunity for updating to suit modern preferences. The flexible layout includes two potential primary suites and a first-floor bonus room with full bath that works well for guests or creative uses. The lower level remains plumbed for a second kitchen and laundry, offering an easy path for future installation or multigenerational living. With no deed restrictions and an expansive amount of usable land, this country estate in town offers endless potential—whether for hobbies, animals, enhancements, or simply enjoying the quiet beauty of its natural surroundings.
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Troy Sacco (941-445-3939)
113 BURNEY RD, OSPREY, FL 34229
$999,50012 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
High 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**
Listing Agent: Mark Lyda (941-586-2670)
312 YACHT HARBOR DR, OSPREY, FL 34229
$1,995,000214 Days on yellowkey MLS ID: A4667293
Bed: 3 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 2572 Built: 1978Monthly Fee: $219 Tax: $14,066 (2024)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$14,066
Remarks: One or more photo(s) has been virtually staged. Directly across the street from one of the most exceptional community-owned marinas on Florida’s west coast, this beautifully renovated waterfront residence offers remarkable views and an extraordinary boating lifestyle within Southbay Yacht and Racquet Club. Considered one of the finest private residential marinas in the region, Southbay’s seven-acre deep water boat basin accommodates kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet, with six feet of water at mean low tide and slips for 175 resident owned boats. Even more remarkable, Southbay’s HOA fees are only $218.87 per month and marina slips remain highly affordable, including both water and electric. With the marina quite literally in your front yard and the charming Southbay neighborhood stretching behind you, this fully renovated waterfront home sits on one of only two waterfront streets in the entire community and features three bedrooms, four full baths and a versatile flex space office/fourth bedroom, with many rooms capturing beautiful water views. Inside, the residence welcomes you with an elegant tray ceiling entry, porcelain plank tile flooring and expansive open living spaces filled with natural light from an abundance of impact-rated windows and sliding glass doors. The beautifully designed entertainment kitchen with breakfast area flows seamlessly into the spacious family and dining rooms, creating a refined yet relaxed setting for everyday living and hosting guests. The outdoor living space is equally impressive, showcasing a newly built custom pool and spa framed by a panoramic clear span pool cage, an expansive stone tiled sun deck and generous covered areas for outdoor dining and entertaining. The private primary suite enjoys double door access to the pool and spa and features a luxurious bath with a deep soaking tub, frameless glass shower, dual vanities, large format tile and two custom walk in closets with built in organization systems. Two guest suites each include private en suites, with one offering marina views and the other opening directly to the pool terrace, both with custom closets. This move in ready residence also includes a three car garage, brick paver driveway and mature tropical landscaping. Just steps away, the newly renovated Southbay Yacht and Racquet Club clubhouse overlooks the marina and features a 99 person ballroom with catering kitchen and dance floor, a community gathering room with piano and entertainment area, fitness center, card room, library and meeting room. Residents also enjoy a geothermal heated pool, youth pool, covered waterfront patios, three tennis courts, four pickleball courts, bocce ball, shuffleboard, basketball court, kayak storage, a waterfront park, 20 acres of common grounds and five miles of scenic sidewalks. Southbay is golf cart friendly and offers an active social calendar with weekly gatherings, seasonal events and a vibrant Power and Sail Club. This is a rare opportunity to enjoy marina views, waterfront living and one of the Gulf Coast’s most beloved boating communities. Be sure to request the 50 page digital property catalog and watch the property film for a complete look at this exceptional residence.
1602 SOUTHBAY DR, OSPREY, FL 34229
$974,900231 Days on yellowkey MLS ID: A4665288
1 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2980 Built: 1986Monthly Fee: $204 Tax: $9,955 (2024)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$9,955
Remarks: Welcome to your slice of Florida paradise! Nestled on a spacious corner lot in the highly sought-after Southbay Yacht & Racquet Club, this elegant residence captures the essence of the coastal lifestyle—enhanced by thoughtful recent updates including a new roof replaced in 2023, fresh interior paint, an updated kitchen, and a beautifully updated pool and jacuzzi. As you arrive, mature tropical landscaping and stately curb appeal immediately set the tone. Step inside to a generously sized home designed for both relaxation and entertaining. Open living areas, large windows, and high ceilings create an airy, welcoming atmosphere, while the refreshed interiors offer a clean, move-in-ready feel. The updated kitchen serves as the heart of the home, providing both style and functionality for everyday living and hosting guests. The interior flows seamlessly into the private outdoor oasis, where the recently updated pool and jacuzzi invite you to enjoy endless days under the Florida sun. Whether hosting friends for a casual barbecue, unwinding with a sunset soak, or enjoying your morning coffee poolside, this space perfectly embodies Florida’s indoor-outdoor lifestyle. Positioned on a corner lot, the home offers exceptional privacy, light, and space—ideal for family gatherings or a peaceful retreat. Spacious bedrooms provide comfort for both owners and guests. A washer and dryer convey with the sale, along with a brand-new pool table, adding both convenience and entertainment value. Life in Southbay Yacht & Racquet Club is more than just owning a home—it’s embracing a lifestyle. Enjoy access to the deep-water marina with Gulf access, tennis and pickleball courts, a vibrant social calendar, fitness amenities, and waterfront strolls. Just minutes away are the pristine beaches of Siesta Key and Nokomis, along with world-class dining and boutique shopping. Here, every day truly feels like vacation.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Thomas Kiessling (941-920-1678)
1471 SHOAL WAY, OSPREY, FL 34229
$1,499,00071 Days on yellowkey MLS ID: A4683702
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2798 Built: 1985Monthly Fee: $219 Tax: $6,036 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$6,036
Remarks: One or more photo(s) has been virtually staged. This exceptional residence truly checks every box. Designed by a renowned architect for his own family, 1471 Shoal Way is a masterclass in thoughtful design, quality craftsmanship, and effortless livability. Set on one of the largest lots in Southbay (just shy of half an acre) privacy was a guiding principle in the home’s design. Tucked at the end of a quiet cul-de-sac and overlooking an expansive green space, the property feels even more open and serene. No expense has been spared in the home’s extensive upgrades, evident the moment you step inside. Eight-inch wide white oak flooring, custom cabinetry, and high-level quartz countertops create a refined yet inviting aesthetic throughout. A striking, oversized fireplace crafted from natural coral stone anchors the living space and is beautifully framed by solid iron double doors—an architectural feature unique to this home. The layout is equally impressive, offering two distinct living areas, four bedrooms, and three baths, thoughtfully designed to maximize both functionality and flow. The oversized garage includes a workshop area and a climate controlled storage space! With every detail already complete, this home allows you to fully enjoy the idyllic waterfront lifestyle Southbay is known for—whether boating, playing pickleball or tennis, or simply relaxing poolside. Boating in Southbay is made easy with its marina located in the center of the development. Peace of mind comes standard with a metal roof designed to resemble barrel tile, hurricane-rated windows, and a location outside of the flood zone, offering both resilience and long-term value. Pack your bathing suit and bring your boat – live the Florida lifestyle to the fullest. Exclusions: mounted tv/screens, potted plants Pool heater conveys as is
Listing Agent: Lauren Doyle (941-993-9733)
1527 BUOY LN, OSPREY, FL 34229
$1,199,00028 Days on yellowkey MLS ID: A4688266
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
Taxes:$8,555
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)
571 PINE RANCH EAST RD, OSPREY, FL 34229
$650,000221 Days on yellowkey MLS ID: A4665938
2 Days Off yellowkey (back on 4/6/2026)
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2746 Built: 1995Monthly Fee: $25 Tax: $6,575 (2024)Community: Bay Oaks Estates Unit 1Spa: NoSingle Family
Taxes:$6,575
Remarks: Under contract-accepting backup offers. One of the largest homes in Bay Oaks Estates, with the second-largest floor plan in the community, this 5-bedroom, 2.5-bath single-story pool retreat delivers the best of indoor-outdoor Florida living with flexible spaces for guests, work, and play. Curb appeal pops with a brick paver circular drive, lush, well-established landscaping highlighted by a mature magnolia and fragrant gardenias, and a covered, columned entry with French double doors and an arched transom. Inside, high ceilings and an abundance of natural light set a welcoming tone. The formal living and dining rooms flow to the heart of the home – a well-appointed kitchen designed for everyday living and entertaining, featuring granite counters, tile backsplash, stainless appliances, a center island with raised breakfast bar, closet pantry, built-in desk and wine rack, recessed & pendant lighting, and a picturesque breakfast nook with wraparound windows. The kitchen opens to the spacious family room with a tray ceiling and mirrored media niche. A pocketing three-panel slider seamlessly extends the living space to the covered lanai and screened pool; additional sliders from the formal living room, the primary suite, and a secondary bedroom maintain the indoor–outdoor connection. Out back, the lanai enjoys a private, tranquil, tree-lined backdrop accented by a mature starfruit tree, overlooking a curved, free-form pool with twin arc fountain jets, a raised sun terrace for lounging, and generous space to relax or gather. A screen door leads to the lawn and a separate pergola patio with power – perfect for morning coffee or an evening grill. From the backyard you have direct access to the Legacy Trail, the popular paved, multi-use path linking Sarasota and Venice, for miles of biking and walking through nature. The private primary retreat offers lanai access, two closets (one walk-in), and a spa-like en-suite bath with a Jacuzzi jetted soaking tub framed by an arched window with plantation shutters, separate walk-in shower with wall body sprays, a long double vanity, and a private water closet. Thoughtful split-bedroom design places three secondary bedrooms and a full bath together in their own wing (one is oversized with lanai access that can flex as a game/media space), while a full 5th bedroom – currently used as an office – sits near the primary suite. An interior laundry room adds storage shelves, cabinets, and a utility sink. Major updates for peace of mind include: replumbed water lines, roof (2015), A/C (2019), new water heater (2024), new pool pump (2024), kitchen appliances (2021), washer and dryer (2023), polycarbonate storm panels, and irrigation. All in a well-kept, low-fee, pet-friendly Osprey community conveniently located just minutes from top-rated schools, including the prestigious Pine View School, and close to the Gulf beaches of world-renowned Siesta Key, Nokomis, and Venice, as well as Oscar Scherer State Park, and a variety of shopping, dining, entertainment, and everyday conveniences; the Gulf Coast lifestyle at its finest. Schedule your private showing today and fall in love with the lifestyle that 571 Pine Ranch East Rd has to offer.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Christiana Kopetzky (941-500-4143)
1016 SCHERER WAY, OSPREY, FL 34229
$950,00037 Days on yellowkey MLS ID: A4687161
0 Days Off yellowkey (back on 3/30/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2921 Built: 2003Monthly Fee: $115 Tax: $5,442 (2025)Community: Rivendell Unit 5 The WoodlandsSingle Family
Taxes:$5,442
Remarks: Under contract-accepting backup offers. BEAUTIFUL INSIDE and exceptionally well maintained, this Rivendell home offers the kind of upgrades, efficiency, and outdoor living that are becoming increasingly hard to find. This Luxurious home is situated on a large beautifully landscaped, lake front lot with a Southeast Exposure overlooking Oscar Scherer State park! The interior layout is spacious and functional, featuring tile flooring throughout the main living areas and carpet in the bedrooms for comfort. A dedicated front office connects directly to the primary suite, creating a flexible space ideal for working from home, a sitting room, or even a private retreat. High ceilings and an open flow between the living spaces enhance the overall feel, while the home’s condition reflects true pride of ownership. Step outside and the property truly separates itself. The heated pool has been resurfaced with Pebble Tec and features a solar heating system that was just replaced in 2024, providing year-round enjoyment with energy efficiency. The outdoor space is further enhanced with hurricane roll-down protection, an outdoor stereo system, and a removable baby safety fence—offering both entertainment and peace of mind. Major updates have already been handled, including a BRAND NEW ROOF in 2025 with a transferable 20-year warranty and TWO NEW A/C systems installed in 2025. The home also benefits from an irrigation well, helping maintain the lush landscaping while keeping water costs zero. Total electric costs have remained under $2,400 annually for the entire property, showcasing impressive efficiency for a home of this size. Additional features include a mini-split A/C system in the garage paired with an insulated garage door—perfect for a workshop, gym, or climate-controlled space—as well as a large safe that conveys with the sale. Rivendell residents enjoy a well-rounded lifestyle with low HOA fees that include a heated community pool, playground, and scenic recreational trails—all with no CDD fees. The community offers a rare private path directly to Pine View School and borders Oscar Scherer State Park along with over 200 acres of preserved land, creating a unique blend of convenience and natural surroundings. The home is near both Siesta and Nokomis Beaches, Costco, and loads of shopping and restaurants. Home is situated less than a mile from the Legacy Bike Trail. Minutes to the distinguished Pine View School, the #1 rated public gifted college-prep school in Florida. This is a rare opportunity to own a move-in-ready home where the major expenses have already been taken care of—offering a combination of condition, upgrades, and outdoor lifestyle that is hard to match. Book your private showing now to see this property for yourself!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
360 N POINT RD, OSPREY, FL 34229
$1,499,000 MLS ID: A4617671
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2913 Built: 2023Community: Oaks 3 Ph 1Single Family
Taxes:
Tax Year:
Remarks: **DON’T WAIT TO BUILD!** EXQUISITE, NEWLY-CONSTRUCTED and NEVER LIVED-IN, SPANISH MISSION STYLE home behind the Secure Gates of the COVETED, OAKS PRESERVE Country Club Neighborhood on Sarasota Bay waters offers superb attention to detail. This Custom-Built residence boasts 3 EN SUITE BEDROOMS + 3 FULL and 1 HALF BATHS and a desirable Open Floorplan concept. A well-equipped Chef’s Kitchen features a large island sitting area, Bosch appliances including 5-burner Gas range, wine storage, etc. while the adjacent great room and dining room are ideal for entertaining and showcase Vaulted and High Ceilings, a cozy fireplace and engineered hardwood floors. The Owner’s Bedroom Suite features a Large Walk-In Closet, Custom Tiled and Glass Enclosed Shower, free-standing soaker Tub, Dual Vanities, bidet and magnificent tile work. Enjoy the utmost Privacy with a Preserve view from the expansive Courtyard and backyard. Circular Driveway with Porte-Cochere + detached 2-car Garage. Hurricane Impact Windows & Doors; Constructed per the latest Hurricane standards. 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. One or more photo(s) has been virtually staged. **ENJOY THE 3D VIRTUAL TOUR**
1211 LOST CREEK CT, OSPREY, FL 34229
$829,000 MLS ID: A4680671
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2876 Built: 2002Community: Rivendell WoodlandsSingle Family
Remarks: Under contract-accepting backup offers. **BEAUTIFULLY UPDATED AND MOVE-IN READY, THIS SPACIOUS 4-BEDROOM + OFFICE/DEN HOME OFFERS NEARLY 2,900 SQUARE FEET** of thoughtfully designed living space with potential for a private in-law or multi-generational suite. Featuring 3 full baths and a coveted 3-car garage, this reconfigured floor plan provides flexibility, privacy, and comfort for today’s lifestyle. Situated on an ideal corner lot, the home enjoys peaceful water views from the rear and a lovely park view from the front. Major updates include a brand-new kitchen with granite countertops and stainless-steel appliances, fresh interior and exterior paint, and new flooring throughout, including luxury vinyl plank, etc. Plantation shutters add timeless charm and style. Newer ROOF (2021). Located in the highly sought-after community of Rivendell, known for its tree-lined streets, serene lakes, and natural preserves spanning 380 acres adjacent to Oscar Scherer State Park. This home is just minutes from nationally ranked Pine View School, Sarasota’s nationally ranked gifted school, as well as The Legacy Trail for miles of biking, walking, and skating. Enjoy the best of Florida living just 6 miles from Nokomis Beach and approximately 20 minutes to Siesta Key Beach. Rivendell is a deed-restricted community offering residents a community pool, playground, park, and gazebo. This exceptional home combines location, lifestyle, and luxury—schedule your private showing today!
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