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157 Properties

157 Properties Available In Osprey

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FL >Osprey >
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627 N MACEWEN DR, Osprey, FL 34229
1/23 23

$1,950,000

Pending

Single Family Home

4 Beds 5 Baths 3,857 SqFt

627 N MACEWEN DR, Osprey, FL 34229

Under contract-accepting backup offers. **STUNNING GOLF COURSE ESTATE with WATER and GOLF COURSE VIEW in the Highly Soug...

Listed by

Stellar MLS
1602 SOUTHBAY DR, Osprey, FL 34229
1/51 51

$995,000

Active

Single Family Home

4 Beds 4 Baths 2,980 SqFt

1602 SOUTHBAY DR, Osprey, FL 34229

Welcome to your slice of Florida paradise! Nestled on a spacious corner lot in the highly sought-after Southbay Yacht & ...

Listed by

Stellar MLS
571 PINE RANCH EAST RD, Osprey, FL 34229
1/87 87

$685,000

Active

Single Family Home

5 Beds 3 Baths 2,746 SqFt

571 PINE RANCH EAST RD, Osprey, FL 34229

One of the largest homes in Bay Oaks Estates, this 5-bed, 2.5-bath single-story pool retreat delivers the best of indoor...

Listed by

Stellar MLS
123 WINDWARD DR, Osprey, FL 34229
1/77 77

$850,000

Active

Single Family Home

3 Beds 2 Baths 1,894 SqFt

123 WINDWARD DR, Osprey, FL 34229

This immaculate and meticulously maintained 3-bedroom, 2-bath home in the sought-after Southbay Yacht & Racquet communit...

Listed by

Stellar MLS
708 ANNA HOPE LN, Osprey, FL 34229
1/31 31

$549,000

Pending

Single Family Home

3 Beds 2 Baths 2,133 SqFt

708 ANNA HOPE LN, Osprey, FL 34229

Under contract-accepting backup offers. Florida's perfect floor plan! Built in 2002, this home features soaring ceilings...

Listed by

Stellar MLS
447 OAK POINT RD, Osprey, FL 34229
3D

$545,000

Active

Single Family Home

4 Beds 3 Baths 2,688 SqFt

447 OAK POINT RD, Osprey, FL 34229

Prepare to be impressed as you enter this bright and spacious maintenance-free townhome with soaring ceilings, an abunda...

Listed by

Stellar MLS
140 SEA ANCHOR DR, Osprey, FL 34229
1/56 56

$4,900

Active

Single Family Home

3 Beds 3 Baths 2,981 SqFt

140 SEA ANCHOR DR, Osprey, FL 34229

PREVIEW BY APPOINTMENT ONLY. This 3 bed, 3 bath, plus office and heated POOL home is located in the beautiful Southbay Y...

Listed by

Stellar MLS
563 PINE RANCH EAST RD, Osprey, FL 34229
1/55 55

$675,000

Pending

Single Family Home

3 Beds 2 Baths 2,346 SqFt

563 PINE RANCH EAST RD, Osprey, FL 34229

Under contract-accepting backup offers. Step into your dream home in the sought-after Bay Oaks Estates where comfort, fu...

Listed by

Stellar MLS
135 TINA ISLAND DR, Osprey, FL 34229
1/32 32

$3,380,000

Active

Single Family Home

3 Beds 5 Baths 2,572 SqFt

135 TINA ISLAND DR, Osprey, FL 34229

Retreat to paradise in this stunning waterfront home, built new in 2011, in highly sought-after Sorrento Shores, Osprey....

Listed by

Stellar MLS
370 SUGAR MILL DR, Osprey, FL 34229
3D

$2,650,000

Active

Single Family Home

5 Beds 6 Baths 4,783 SqFt

370 SUGAR MILL DR, Osprey, FL 34229

**Meticulously maintained, architectural perfection, this bright, spectacular estate featuring incredibly spacious first...

Listed by

Stellar MLS
101 OSPREY POINT DR, Osprey, FL 34229
1/56 56

$5,000,000

Active

Single Family Home

4 Beds 6 Baths 5,087 SqFt

101 OSPREY POINT DR, Osprey, FL 34229

A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within th...

Listed by

Stellar MLS
2313 JESSIE HARBOR DR #2302, Osprey, FL 34229
1/41 41

$2,500

Active

Condo

2 Beds 2 Baths 1,391 SqFt

2313 JESSIE HARBOR DR #2302, Osprey, FL 34229

ANNUAL UNFURNISHED VILLA AVAILABLE FOR LEASE IN BLACKBURN HARBOR IN OSPREY! This beautiful 2BR 2BA villa has a large la...

Listed by

Stellar MLS
305 BAY VISTA AVE, Osprey, FL 34229
1/36 36

$2,500

Active

Single Family Home

2 Beds 2 Baths 1,069 SqFt

305 BAY VISTA AVE, Osprey, FL 34229

Welcome to this stunning two-bedroom, two-bathroom retreat, perfectly designed for relaxation and entertainment! <br> <b...

Listed by

Stellar MLS
422 BLUE GARDEN LN, Osprey, FL 34229
1/100 100

$1,750,000

Active

Single Family Home

3 Beds 4 Baths 3,872 SqFt

422 BLUE GARDEN LN, Osprey, FL 34229

A grand traditional residence, this 3-bedroom, 3.5-bath home is tucked into lush tropical landscaping on a quiet cul-de-...

Listed by

Stellar MLS
701 EAGLENOOK WAY, Osprey, FL 34229
1/65 65

$1,075,000

Active

Single Family Home

4 Beds 5 Baths 3,533 SqFt

701 EAGLENOOK WAY, Osprey, FL 34229

A truly rare opportunity to own a home on over 2 acres in Osprey, FL. Pine Ranch is a charming enclave of 36 properties ...

Listed by

Stellar MLS
4256 EXPEDITION WAY #107, Osprey, FL 34229
1/45 45

$2,250

Active

Condo

3 Beds 2 Baths 1,528 SqFt

4256 EXPEDITION WAY #107, Osprey, FL 34229

Welcome to Bay Street in Osprey! This 3-bedroom, 2-bath condominium offers the comfort of single-level living on the sec...

Listed by

Stellar MLS
508 MEADOW SWEET CIR, Osprey, FL 34229
1/76 76

$499,900

Active

Single Family Home

2 Beds 2 Baths 1,604 SqFt

508 MEADOW SWEET CIR, Osprey, FL 34229

The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home...

Listed by

Stellar MLS
264 SARATOGA CT, Osprey, FL 34229
3D

$2,300,000

Pending

Single Family Home

4 Beds 4 Baths 3,857 SqFt

264 SARATOGA CT, Osprey, FL 34229

Under contract-accepting backup offers. **BRILLIANTLY DESIGNED AND RENOVATED, CUSTOM GOLF COURSE ESTATE with SPECTACULAR...

Listed by

Stellar MLS
156 BISHOPSCOURT RD, Osprey, FL 34229
1/97 97

$1,385,000

Active

Single Family Home

3 Beds 4 Baths 3,112 SqFt

156 BISHOPSCOURT RD, Osprey, FL 34229

This stunning 3 bedroom, 3.5 bath home, designed by the renowned architect Frank Folsom Smith, stands out with its uniqu...

Listed by

Stellar MLS
1817 HIGHLAND RD, Osprey, FL 34229
1/9 9

$2,395

Active

Townhouse

2 Beds 2 Baths 1,145 SqFt

1817 HIGHLAND RD, Osprey, FL 34229

Lovely 2 bed/2 bth well maintained townhouse with a 2 car garage Set in a private enclave in the desirable West of Trai...

Listed by

Stellar MLS
304 PINE RUN DR #304, Osprey, FL 34229
1/34 34

$2,000

Active

Condo

2 Beds 2 Baths 1,729 SqFt

304 PINE RUN DR #304, Osprey, FL 34229

Stunning annual unfurnished 2 bed/2 bath ground floor condo located at Pine Run in Osprey, FL. Water, sewer/trash, lawn...

Listed by

Stellar MLS
133 OSPREY POINT DR, Osprey, FL 34229
1/99 99

$1,600,000

Pending

Single Family Home

3 Beds 3 Baths 3,679 SqFt

133 OSPREY POINT DR, Osprey, FL 34229

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Custon Home located in the exclu...

Listed by

Stellar MLS
111 WOODLAND PL, Osprey, FL 34229
1/94 94

$245,000

Active

Condo

2 Beds 2 Baths 1,316 SqFt

111 WOODLAND PL, Osprey, FL 34229

Hidden away in Osprey is the private oasis of Pine Run. You could not find a more natural setting and fantastic location...

Listed by

Stellar MLS
260 HIDDEN BAY DR #504, Osprey, FL 34229
1/53 53

$5,000

Active

Condo

2 Beds 3 Baths 1,950 SqFt

260 HIDDEN BAY DR #504, Osprey, FL 34229

Annual Turnkey Furnished Penthouse on the Bay! If you want mesmerizing views of intracoastal waterway, Little Sarasota B...

Listed by

Stellar MLS
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London Foster White Logo
London Foster (LondonFosterRealty.com)

Bobby Mahallati License ID: 0705018

+1(305) 766-7993 [email protected]

9001 SW 73rd Ct, Miami, FL, 33156, USA

ABOUT
London Foster is a technology based real estate firm. Our technology is a revolutionary cloud-based platform which empowers our associates to always be engaged.

London Foster provides everything our associates need to conduct their business at our office, remotely or mobile.

No matter where you are you will always be connected to our network with exclusive access, just like if you were at the office.

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London Foster White Logo
London Foster (LondonFosterRealty.com)

Bobby Mahallati License ID: 0705018

+1(305) 766-7993 [email protected]

9001 SW 73rd Ct, Miami, FL, 33156, USA

ABOUT
London Foster is a technology based real estate firm. Our technology is a revolutionary cloud-based platform which empowers our associates to always be engaged.

London Foster provides everything our associates need to conduct their business at our office, remotely or mobile.

No matter where you are you will always be connected to our network with exclusive access, just like if you were at the office.

    • Home
      Featured Areas
      1. Florida
      2. New York
      Contact
    • Sellers
      1. Sellers
      2. Home Valuation
      Team
    • Buyers
      1. Buyers
      2. Buy
      3. Calculator
      About
      1. About Me
      2. Testimonials

Get My App

Accessibility Statement

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.