MLS Listings for Sale in Osprey, FL

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NEW 11 HRS AGO

ABOUT THIS HOME
MLS Listings for Sale in Osprey, FL
Welcome to Bay Acres - a hidden coastal enclave West of the Trail where timeless Florida living meets everyday comfort. Situated on a generous corner lot with a circular driveway, this 3-bedroom, 3-bath single-family pool home offers a spacious and functional split floor plan designed for both privacy and connection. Step inside and immediately feel the openness of the main living area, where large double doors open wide to an oversized screened pool back yard oasis creating a seamless indoor/outdoor flow — perfect for relaxing evenings or effortless entertaining. Whether you’re hosting family gatherings or enjoying quiet mornings with coffee in the breeze, this expansive outdoo

$659,000

3 beds3 baths2,384 sq ft

315 Bayshore Dr, Osprey, FL 34229

Flexible floor plan • Natural light • Corner lot

NEW 20 HRS AGO

ABOUT THIS HOME
MLS Listings for Sale in Osprey, FL
Experience breathtaking views of the Bay and Gulf from this spacious 3 bedroom, 3 bath end unit, featuring a separate dining room and den. Completely updated and meticulously maintained, this unit is beautifully appointed and custom features abound. A private elevator takes you to a majestic foyer which opens to the great room. Facing west the views are gorgeous from sunrise to sunset. The kitchen is high-end and stocked with top-of-the-line appliances. The master suite has a large sitting area, walk-in closets, a luxurious bath and incredible views! Spacious and lavish, this unit lives large, with the feeling of a house. Yet you enjoy a luxury lifestyle of comfort and ease with all the con

$1,500,000

3 beds3 baths2,778 sq ft

385 N Point Rd #704, Osprey, FL 34229

Majestic foyer • Private elevator • Walk-in closets

ABOUT THIS HOME
MLS Listings for Sale in Osprey, FL
One or more photo(s) has been virtually staged. Upon passing the gated pillars of the winding driveway you come upon a hidden treasure. 2.5 Acres of beauty tucked away just off Tamiami and Bay in Osprey. This property backs up to the renowned Pine View school grades 2-12. One of the finest schools in the state and country. https://www. sarasotacountyschools.net/o/pineview/ page/pine-view-admissions. The peace and tranquility of the outdoor space is highlighted by a resort style swimming pool 40 x10 and attached 25x13 swim shelf with infinity edge, Bubblers, waterfalls, fire balls and 2400Sqft of entertainment area, including a 4 hole putting green, The totally remodeled home has NEW, NEW an

$1,300,000

4 beds3 baths2,474 sq ft

700 Faith Ave, Osprey, FL 34229

Bubblers • Waterfalls • Fire balls

ABOUT THIS HOME
MLS Listings for Sale in Osprey, FL
Nestled within the exclusive gated community of the Oaks Club in Osprey, Florida. This singular estate represents a masterful confluence of architectural refinement and modern luxury, encompassing nearly 7000 ft. ² of conditioned living space, the residence has undergone an extraordinary transformation – reflecting an investment exceeding $1.5 million – to achieve a standard of craftsmanship seldom encountered in contemporary homes. The grand foyer reimagined with architectural restraint and elegance, opens to a series of impeccably curated, living spaces defined by scale, light and material integrity. The entire home has been freshly repainted, presenting a pristine, harmo

$3,995,000

4 beds6 baths6,705 sq ft

691 Eagle Watch Ln, Osprey, FL 34229

Freestanding tub • Kitchen rebuilt • Bespoke cabinetry

ABOUT THIS HOME
MLS Listings for Sale in Osprey, FL
* * ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A . 83-ACRE CORNER LOT * * Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous . 83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home showcases timeless architecture with a thoughtful layout and extensive 2023–2025 updates throughout. From its striking curb appeal to its serene outdoor living spaces, every detail has been meticulously curated. Inside, the home offers 4 EN SUITE BEDROOMS, 5.5 BATHS, and a 3-CAR GARAGE

$2,300,000

4 beds5.5 baths4,346 sq ft

538 Dove Pointe Dr, Osprey, FL 34229

Gated community • Landscaped property • New hvac units

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

$849,900

3 beds2 baths2,103 sq ft

120 Candyce Dr, Osprey, FL 34229

Property at 218 Palm Air Dr, Osprey, FL 34229, 2 beds, 2 baths

$189,000

2 beds2 baths1,120 sq ft

218 Palm Air 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 325 Osprey Point Dr, Osprey, FL 34229, 3 beds, 4.5 baths

$1,690,000

3 beds4.5 baths3,905 sq ft

325 Osprey Point Dr, Osprey, FL 34229

Property at 392 Park Trace Blvd, Osprey, FL 34229, 4 beds, 3 baths

$939,000

4 beds3 baths2,802 sq ft

392 Park Trace Blvd, Osprey, FL 34229

Property at 453 E Macewen Dr, Osprey, FL 34229, 4 beds, 3.5 baths

$1,899,000

4 beds3.5 baths4,191 sq ft

453 E Macewen Dr, 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 133 Osprey Point Dr, Osprey, FL 34229, 3 beds, 3 baths

$1,550,000

3 beds3 baths3,679 sq ft

133 Osprey Point Dr, 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 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 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

$479,000

2 beds2 baths2,148 sq ft

32 Bay Ave, Osprey, FL 34229

Property at 2513 Bayshore Rd, Nokomis, FL 34275, 6 beds, 5 baths

$6,250,000

6 beds5 baths4,800 sq ft

2513 Bayshore Rd, Nokomis, FL 34275

Property at 225 Harbor House Dr, Osprey, FL 34229, 6 beds, 4 baths

$2,850,000

6 beds4 baths4,546 sq ft

225 Harbor House 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 18 N Casey Key Rd, Osprey, FL 34229, 3 beds, 2 baths

$2,350,000

3 beds2 baths1,977 sq ft

18 N Casey Key Rd, 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

Property at 600 Eagle Watch Ln, Osprey, FL 34229, 3 beds, 3 baths

$2,195,000

3 beds3 baths3,681 sq ft

600 Eagle Watch Ln, Osprey, FL 34229

Property at 854 Macewen Dr, Osprey, FL 34229, 4 beds, 5 baths

$3,950,000

4 beds5 baths9,081 sq ft

854 Macewen Dr, Osprey, FL 34229

Property at 1811 Highland Rd, Osprey, FL 34229, 2 beds, 2 baths

$443,000

2 beds2 baths1,725 sq ft

1811 Highland Rd, 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 140 N Casey Key Rd, Osprey, FL 34229, 3 beds, 3.5 baths

$2,500,000

3 beds3.5 baths2,473 sq ft

140 N Casey Key Rd, 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 701 Eaglenook Way, Osprey, FL 34229, 4 beds, 4.5 baths

$1,075,000

4 beds4.5 baths3,533 sq ft

701 Eaglenook Way, 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 447 Oak Point Rd, Osprey, FL 34229, 4 beds, 3 baths

$545,000

4 beds3 baths2,688 sq ft

447 Oak Point Rd, Osprey, FL 34229

Property at 244 Woodland Dr #244, Osprey, FL 34229, 2 beds, 2 baths

$225,000

2 beds2 baths1,325 sq ft

244 Woodland Dr #244, Osprey, FL 34229

Property at 121 N Casey Key Rd, Osprey, FL 34229, 4 beds, 5.5 baths

$7,100,000

4 beds5.5 baths4,096 sq ft

121 N Casey Key Rd, Osprey, FL 34229

Property at 851 Placid Lake Dr, Osprey, FL 34229, 5 beds, 4 baths

$760,000

5 beds4 baths3,395 sq ft

851 Placid Lake Dr, Osprey, FL 34229

Property at 33 Bishops Court Rd #118, Osprey, FL 34229, 2 beds, 2.5 baths

$695,000

2 beds2.5 baths1,890 sq ft

33 Bishops Court Rd #118, 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 17 Bayhead Ln, Osprey, FL 34229, 3 beds, 2 baths

$1,325,000

3 beds2 baths2,850 sq ft

17 Bayhead Ln, Osprey, FL 34229

Property at 85 Sugar Mill Dr, Osprey, FL 34229, 3 beds, 3 baths

$2,150,000

3 beds3 baths4,191 sq ft

85 Sugar Mill Dr, Osprey, FL 34229

Property at 471 Park Trace Blvd, Osprey, FL 34229, 4 beds, 3 baths

$699,000

4 beds3 baths2,267 sq ft

471 Park Trace Blvd, Osprey, FL 34229

Property at 1218 Yacht Harbor Dr, Osprey, FL 34229, 3 beds, 3 baths

$1,150,000

3 beds3 baths3,297 sq ft

1218 Yacht Harbor Dr, Osprey, FL 34229

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Based on information submitted to the MLS GRID as of Tue Nov 11 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.

MLS Listings for Sale in Osprey

There are currently 128 mls listings for sale in Osprey at a median listing price of $760K. 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 112 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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