Single Story homes for sale & real estate in Osprey, FL

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OPEN SUN, 12PM TO 3PM

ABOUT THIS HOME
Single Story Home for sale in Osprey, FL:
Lovely turn-key furnished, 3BR/2BA and a pool half BA, 3 car garage home bordering Oscar Scherer State Park, providing privacy, lake views and peacefulness. The beautiful Stanford 2,534 SqFt model home affords you stunning views out all the wind impact windows. This home features a fabulous great room floor plan with vaulted trey ceilings, crown molding, tile on the diagonal with marble inlays and a built-in entertainment center and dining buffet. The gourmet kitchen is a chef’s dream with a large center island, built-in gas cooktop with vented hood, oven/microwave and a built-in desk and there is lots of storage space and looks out to the great room. The primary suite is stunning wi

$765,000

3 beds2.5 baths2,534 sq ft

640 Crane Prairie Way, Osprey, FL 34229

Soaking tub • Gourmet kitchen • Lighted tray ceiling

NEW 13 HRS AGO

ABOUT THIS HOME
Single Story Home for sale in Osprey, FL:
Waterfront villa offering MAINTENANCE-FREE LIVING just minutes to the ICW with no bridges! This 2BR/2BA home features a 2024 10,000 lb BOAT LIFT with water & electric, new Trex decking and epoxy concrete, HURRICANE IMPACT WINDOWS/DOORS, and a ROOF from 2019. Inside, enjoy a 2024 TOTAL KITCHEN REMODEL with quartz counters, backsplash, NEW GE appliances, and OPEN FLOOR PLAN. Additional upgrades include UV light in air ducts, re-piped plumbing, new Levelor blinds, and screened front/back lanais with custom lighting and pavers. Community amenities include pool, cabana, and boat docks. Conveniently located near beaches, Legacy Trail, golf, state park, and downtown Venice & Sarasota&m

$525,000

2 beds2 baths1,394 sq ft

119 Villa Dr, Osprey, FL 34229

Boat lift • Open floor plan • Garage

3D WALKTHROUGH

ABOUT THIS HOME
Single Story Home for sale in Osprey, FL:
* * STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood * * on Sarasota Bay waters… situated on TWO LOTS totaling over 3/4 acres, the Main House on Lot #1 features 3 Beds / 3 Baths while the separate Guest House on adjacent Lot #2 boasts 1 Bed / 1 Bath, kitchenette, laundry, etc. An oversized Pool adorns the private setting with lush landscape and water view. This former home of famed architect, Bo MacEwen, who also designed the breathtaking Oaks’ Clubhouse, boasts an impressive 253FT frontage along the highly sought-after Osprey Point Drive in the Bayside neighborhood often regarded as the “Park Avenue” of The Oaks Golf & Co

$1,975,000

4 beds4 baths4,001 sq ft

75 Osprey Point Dr, Osprey, FL 34229

Oversized pool • Nearby private dock • Private setting

OPEN SUN, 1PM TO 4PM3D WALKTHROUGH

ABOUT THIS HOME
Single Story Home for sale in Osprey, FL:
Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large private lot. Interior highlights include double primary bedrooms, tiled walk-in showers in both full bathrooms, an outdoor shower, a generous laundry room with cabinetry, a practical kitchen with pantry and hurricane rated windows. The paver lanai with automated hurricane screen and expansive paver deck surrounding the swimming pool with solar heat provide substantial outdoor living space.

$800,000

3 beds2.5 baths2,134 sq ft

102 Windward Dr, Osprey, FL 34229

Spacious great room • Large private lot • Cathedral ceiling

NEW 28 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Single Story Home for sale in Osprey, FL:
This is an outstanding Southbay residence and a fantastic opportunity to live in one of the best boating communities on the Southwest coast of Florida. This home has been updated with a gourmet custom kitchen, perfect for entertaining guests and hosting company. From the granite countertops to the gas cooktop, and custom cabinetry, it is a pleasure to cook in here! The dining room is spacious with plenty of room plus a built-in custom buffet. overlooking the expansive living room with a wood-burning fireplace. One special feature of this home is the designed media room, set up for a large screen TV, and sound specially wired throughout to achieve maximum viewing and listening pleasure. The

$895,000

3 beds2.5 baths2,676 sq ft

238 Lookout Point Dr, Osprey, FL 34229

Designed media room • Geo-thermal pool • Waterfront park

Property at 137 Osprey Point Dr, Osprey, FL 34229, 4 beds, 3 baths

$1,425,000

4 beds3 baths3,303 sq ft

137 Osprey Point Dr, Osprey, FL 34229

Property at 216 Palm Air Dr, Osprey, FL 34229, 2 beds, 2 baths

$164,000

2 beds2 baths1,055 sq ft

216 Palm Air Dr, Osprey, FL 34229

Property at 14041 Bellagio Way #218, Osprey, FL 34229, 3 beds, 2 baths

$1,150,000

3 beds2 baths2,374 sq ft

14041 Bellagio Way #218, Osprey, FL 34229

Property at 385 N Point Rd #503, Osprey, FL 34229, 3 beds, 3 baths

$690,000

3 beds3 baths2,203 sq ft

385 N Point Rd #503, Osprey, FL 34229

Property at 362 Pine Run Dr, Osprey, FL 34229, 2 beds, 2 baths

$235,000

2 beds2 baths1,224 sq ft

362 Pine Run Dr, Osprey, FL 34229

Property at 804 Shadow Bay Way, Osprey, FL 34229, 3 beds, 2 baths

$660,000

3 beds2 baths2,279 sq ft

804 Shadow Bay Way, Osprey, FL 34229

Property at 180 Lookout Point Dr, Osprey, FL 34229, 5 beds, 3.5 baths

$2,299,900

5 beds3.5 baths3,236 sq ft

180 Lookout Point Dr, Osprey, FL 34229

Property at 49 Osprey Point Dr, Osprey, FL 34229, 4 beds, 3.5 baths

$2,595,000

4 beds3.5 baths3,953 sq ft

49 Osprey Point Dr, Osprey, FL 34229

Property at 700 Faith Ave, Osprey, FL 34229, 4 beds, 3 baths

$1,300,000

4 beds3 baths2,474 sq ft

700 Faith Ave, Osprey, FL 34229

Property at 315 Bayshore Dr, Osprey, FL 34229, 3 beds, 3 baths

$659,000

3 beds3 baths2,384 sq ft

315 Bayshore Dr, Osprey, FL 34229

Property at 431 Yacht Harbor Dr, Osprey, FL 34229, 3 beds, 2.5 baths

$4,300,000

3 beds2.5 baths3,006 sq ft

431 Yacht Harbor Dr, Osprey, FL 34229

Property at 133 Osprey Point Dr, Osprey, FL 34229, 4 beds, 3 baths

$1,500,000

4 beds3 baths3,679 sq ft

133 Osprey Point Dr, Osprey, FL 34229

Property at 3936 Waypoint Ave, Osprey, FL 34229, 3 beds, 3 baths

$1,089,000

3 beds3 baths2,323 sq ft

3936 Waypoint Ave, Osprey, FL 34229

Property at 1337 Copperwood Dr, Osprey, FL 34229, 3 beds, 2 baths

$595,000

3 beds2 baths2,172 sq ft

1337 Copperwood Dr, Osprey, FL 34229

Property at 583 Pine Ranch East Rd, Osprey, FL 34229, 4 beds, 2 baths

$629,000

4 beds2 baths2,203 sq ft

583 Pine Ranch East Rd, Osprey, FL 34229

Property at 172 Sea Anchor Dr, Osprey, FL 34229, 3 beds, 3 baths

$936,000

3 beds3 baths2,283 sq ft

172 Sea Anchor Dr, Osprey, FL 34229

Property at 1036 Oak Meadow Ln, Osprey, FL 34229, 4 beds, 2 baths

$599,000

4 beds2 baths2,186 sq ft

1036 Oak Meadow Ln, Osprey, FL 34229

Property at 32 Bay Ave, Osprey, FL 34229, 2 beds, 2 baths

$463,000

2 beds2 baths2,148 sq ft

32 Bay Ave, Osprey, FL 34229

Property at 1486 Landview Ln, Osprey, FL 34229, 3 beds, 2 baths

$995,000

3 beds2 baths1,869 sq ft

1486 Landview Ln, Osprey, FL 34229

Property at 903 Tranquility Cir, Osprey, FL 34229, 3 beds, 3 baths

$879,000

3 beds3 baths2,622 sq ft

903 Tranquility Cir, Osprey, FL 34229

Property at 691 Eagle Watch Ln, Osprey, FL 34229, 4 beds, 6 baths

$3,995,000

4 beds6 baths6,705 sq ft

691 Eagle Watch Ln, Osprey, FL 34229

Property at 120 Candyce Dr, Osprey, FL 34229, 3 beds, 2 baths

$799,000

3 beds2 baths2,103 sq ft

120 Candyce Dr, Osprey, FL 34229

Property at 889 Macewen Dr, Osprey, FL 34229, 4 beds, 4 baths

$2,300,000

4 beds4 baths3,235 sq ft

889 Macewen Dr, Osprey, FL 34229

Property at 538 Dove Pointe Dr, Osprey, FL 34229, 4 beds, 5.5 baths

$2,300,000

4 beds5.5 baths4,346 sq ft

538 Dove Pointe Dr, Osprey, FL 34229

Property at 106 Villa Dr #106, Osprey, FL 34229, 2 beds, 2 baths

$249,900

2 beds2 baths1,578 sq ft

106 Villa Dr #106, Osprey, FL 34229

Property at 571 Pine Ranch East Rd, Osprey, FL 34229, 5 beds, 2.5 baths

$685,000

5 beds2.5 baths2,746 sq ft

571 Pine Ranch East Rd, Osprey, FL 34229

Property at 401 N Point Rd #603, Osprey, FL 34229, 3 beds, 3 baths

$699,000

3 beds3 baths2,203 sq ft

401 N Point Rd #603, Osprey, FL 34229

Property at 348 Tropic Dr, Osprey, FL 34229, 2 beds, 2 baths

$119,000

2 beds2 baths864 sq ft

348 Tropic Dr, Osprey, FL 34229

Property at 508 Meadow Sweet Cir, Osprey, FL 34229, 2 beds, 2 baths

$465,000

2 beds2 baths1,604 sq ft

508 Meadow Sweet Cir, Osprey, FL 34229

Property at 385 N Point Rd #704, Osprey, FL 34229, 3 beds, 3 baths

$1,500,000

3 beds3 baths2,778 sq ft

385 N Point Rd #704, Osprey, FL 34229

Property at 291 Hidden Bay Dr #101, Osprey, FL 34229, 2 beds, 2 baths

$400,000

2 beds2 baths1,599 sq ft

291 Hidden Bay Dr #101, Osprey, FL 34229

Property at 232 Woodland Dr, Osprey, FL 34229, 2 beds, 2 baths

$269,900

2 beds2 baths1,325 sq ft

232 Woodland Dr, Osprey, FL 34229

Property at 232 Hidden Bay Dr #504, Osprey, FL 34229, 3 beds, 3 baths

$599,000

3 beds3 baths2,000 sq ft

232 Hidden Bay Dr #504, Osprey, FL 34229

Property at 123 Windward Dr, Osprey, FL 34229, 3 beds, 2 baths

$850,000

3 beds2 baths1,894 sq ft

123 Windward Dr, Osprey, FL 34229

Property at 1602 Southbay Dr, Osprey, FL 34229, 4 beds, 3.5 baths

$995,000

4 beds3.5 baths2,980 sq ft

1602 Southbay Dr, Osprey, FL 34229

Property at 510 Latitude Ln, Osprey, FL 34229, 3 beds, 2 baths

$635,000

3 beds2 baths2,298 sq ft

510 Latitude Ln, Osprey, FL 34229

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Based on information submitted to the MLS GRID as of Sat Nov 22 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Single Story Homes for Sale in Osprey

There are currently 112 single story homes for sale in Osprey at a median listing price of $765K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Osprey stay on the market for 111 days. Popular neighborhoods include Southbay Yacht & Racquet Club, Rivendell, Palmer Ranch, Stoneybrook Golf & Country Club, and Oaks. This map is refreshed with the newest listings in Osprey every 15 minutes.

In the past month, 11 homes have been sold in Osprey. In addition to houses in Osprey, there were also 21 condos, 2 townhouses, and 1 multi-family unit for sale in Osprey last month. Find your dream home in Osprey using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Osprey are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Osprey. Our Osprey real estate stats and trends will give you more information about home buying and selling trends in Osprey. If you're looking to sell your home in the Osprey area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Osprey with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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