Osprey, FL Real Estate & Homes For Sale

108 homes

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3D VIEW
$425,000
2 Beds
2 Baths
1,574 sqft
780 SARABAY ROAD #16,
Osprey, FL 34229
RMS ELITE PROPERTIES
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3D VIEW
0.36 ACRES
$1,047,000
3 Beds
2.5 Baths
2,134 sqft
102 WINDWARD DRIVE,
Osprey, FL 34229
FUTURE HOME REALTY INC
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1.04 ACRES
$149,900
Studio
570 BLACKBURN POINT ROAD #Siesta 25,
Osprey, FL 34229
BRIGHT REALTY
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3D VIEW
0.28 ACRES
$1,049,000
4 Beds
3 Baths
2,775 sqft
366 S CREEK COURT,
Osprey, FL 34229
KELLER WILLIAMS ON THE WATER S
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3D VIEW
$1,025,000
3 Beds
3 Baths
2,778 sqft
401 N POINT ROAD #404,
Osprey, FL 34229
COLDWELL BANKER REALTY
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3D VIEW
$465,000
2 Beds
2 Baths
1,404 sqft
120 VILLA DRIVE #120,
Osprey, FL 34229
MANGROVE REALTY ASSOCIATES
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3D VIEW
0.75 ACRES
$1,445,000
3 Beds
3.5 Baths
3,872 sqft
422 BLUE GARDEN LANE,
Osprey, FL 34229
COLDWELL BANKER REALTY
COMING SOON
3D VIEW
0.48 ACRES
$1,900,000
3 Beds
3.5 Baths
3,924 sqft
168 COASTAL HAMMOCK COURT,
Osprey, FL 34229
MICHAEL SAUNDERS & COMPANY
3D VIEW
$175,000
2 Beds
2 Baths
960 sqft
145 EDGEWOOD DRIVE,
Osprey, FL 34229
GENEROUS PROPERTY
3D VIEW
$159,900
1 Bed
1 Bath
586 sqft
717 PINE RUN DR. #717,
Osprey, FL 34229
PAT WILLIAMS REALTY, LLC
3D VIEW
$625,000
3 Beds
2 Baths
1,937 sqft
250 HIDDEN BAY DRIVE #302,
Osprey, FL 34229
COLDWELL BANKER REALTY
$1,200,000
3 Beds
3 Baths
2,203 sqft
401 N POINT ROAD #703,
Osprey, FL 34229
GENEROUS PROPERTY
3D VIEW
0.38 ACRES
$4,590,000
5 Beds
5 Baths
5,279 sqft
275 LOOKOUT POINT DRIVE,
Osprey, FL 34229
MICHAEL SAUNDERS & COMPANY
OPEN SUN, 12-3PM
3D VIEW
$630,000
4 Beds
2 Baths
2,186 sqft
1036 OAK MEADOW LANE,
Osprey, FL 34229
BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE
3D VIEW
$1,399,000
3 Beds
3 Baths
2,594 sqft
385 NORTH POINT ROAD #701,
Osprey, FL 34229
MICHAEL SAUNDERS & COMPANY
3D VIEW
0.66 ACRES
$3,700,000
4 Beds
4 Baths
4,314 sqft
650 OAKS CREEK COURT,
Osprey, FL 34229
COLDWELL BANKER REALTY
OPEN SUN, 1-3PM
3D VIEW
$449,000
3 Beds
2 Baths
1,883 sqft
7303 JESSIE HARBOR DRIVE #7303,
Osprey, FL 34229
COLDWELL BANKER REALTY
3D VIEW
$695,000
3 Beds
3 Baths
2,594 sqft
385 N POINT ROAD #401,
Osprey, FL 34229
COLDWELL BANKER REALTY
3D VIEW
$629,400
3 Beds
3 Baths
3,147 sqft
3603 N POINT ROAD #202,
Osprey, FL 34229
GENEROUS PROPERTY
3D VIEW
$879,000
3 Beds
2.5 Baths
2,199 sqft
14021 BELLAGIO WAY #309,
Osprey, FL 34229
COMPASS FLORIDA, LLC
3D VIEW
$540,000
3 Beds
2 Baths
2,248 sqft
1346 THORNAPPLE DRIVE,
Osprey, FL 34229
RE/MAX ALLIANCE GROUP
$679,000
2 Beds
2.5 Baths
1,890 sqft
33 BISHOPS COURT ROAD #118,
Osprey, FL 34229
GENEROUS PROPERTY
0.42 ACRES
$1,399,000
3 Beds
3 Baths
2,695 sqft
256 SUGAR MILL,
Osprey, FL 34229
KIMBERLITE WEST REALTY LLC
FOR SALE BY OWNER
$69,900
2 Beds
1 Bath
700 sqft
42 W Oak St #D9,
Osprey, FL 34229
3D VIEW
$165,000
2 Beds
2 Baths
924 sqft
23 SIESTA CIRCLE W,
Osprey, FL 34229
COLDWELL BANKER SARASOTA CENT.
3D VIEW
0.97 ACRES
$3,700,000
5 Beds
5 Baths
6,234 sqft
324 OSPREY POINT DRIVE,
Osprey, FL 34229
COLDWELL BANKER REALTY
3D VIEW
0.38 ACRES
$1,270,000
3 Beds
2 Baths
2,850 sqft
17 BAYHEAD LANE,
Osprey, FL 34229
COLDWELL BANKER REALTY
FORECLOSURE
BANK OWNED
3D VIEW
0.27 ACRES
$655,000
3 Beds
2.5 Baths
2,792 sqft
700 SHADOW BAY WAY,
Osprey, FL 34229
KARA MONEY LLC
3D VIEW
$244,900
2 Beds
2 Baths
1,223 sqft
109 WOODLAND PLACE,
Osprey, FL 34229
PREFERRED SHORE LLC
3D VIEW
0.41 ACRES
$1,700,000
3 Beds
3 Baths
3,118 sqft
141 SUGAR MILL DRIVE,
Osprey, FL 34229
COLDWELL BANKER REALTY
OPEN SUN, 1-3PM
3D VIEW
0.27 ACRES
$1,349,999
4 Beds
4 Baths
3,255 sqft
1417 LANDVIEW LANE,
Osprey, FL 34229
PAT WILLIAMS REALTY, LLC
$34,900
1 Bed
1 Bath
418 sqft
124 Happy Haven Dr #56,
Osprey, FL 34229
3D VIEW
$749,900
3 Beds
2 Baths
2,174 sqft
1328 THORNAPPLE DRIVE,
Osprey, FL 34229
RIVER HILLS PROPERTIES, LLC B
3D VIEW
0.41 ACRES
$797,000
3 Beds
2 Baths
2,623 sqft
200 MONTANA AVENUE,
Nokomis, FL 34275
MOMENTUM REALTY
3D VIEW
0.27 ACRES
$565,000
3 Beds
2 Baths
1,705 sqft
2046 CORDES STREET,
Osprey, FL 34229
MICHAEL SAUNDERS & COMPANY
0.41 ACRES
$950,000
3 Beds
1.5 Baths
2,084 sqft
210 PATTERSON AVENUE,
Osprey, FL 34229
REALTY ONE GROUP MVP
3D VIEW
1.1 ACRES
$9,750,000
5 Beds
7 Baths
8,050 sqft
1216 N CASEY KEY ROAD,
Osprey, FL 34229
PREMIER SOTHEBY'S INTERNATIONAL REALTY
3D VIEW
0.27 ACRES
$1,495,000
3 Beds
2.5 Baths
2,591 sqft
226 SAINT JAMES PARK,
Osprey, FL 34229
KELLER WILLIAMS ON THE WATER S
0.32 ACRES
$2,095,000
4 Beds
3.5 Baths
4,578 sqft
154 LOOKOUT POINT DRIVE,
Osprey, FL 34229
FLAT FEE MLS REALTY
3D VIEW
1.14 ACRES
$1,100,000
5 Beds
3.5 Baths
3,354 sqft
296 PINE RANCH TRAIL,
Osprey, FL 34229
BEYOND REALTY LLC
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Osprey, FL Real Estate Trends

Learn about the Osprey, FL housing market through trends and averages.

Affordability
Home Value
What Locals Say

Affordability of Living in Osprey, FL

The median home value is $661,421

Month	Median home value
October 2025	$664k
November 2025	$661k
December 2025	$659k
January 2026	$659k
February 2026	$660k
March 2026	$660k
April 2026	$659k
May 2026	$657k
June 2026	$655k
July 2026	$655k
August 2026	$658k
September 2026	$661k

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Trends and affordability stats are provided by third party data sources.

Average Home Value in Osprey, FL, by Home Size

Currently, there are 4 new listings in Osprey, FL and 108 homes for sale.

Home Size	Home Value*
2 bedrooms (16 homes)	$319,957
3 bedrooms (54 homes)	$686,118
4 bedrooms (11 homes)	$946,378

*Home value over the past month

What Locals Say about Osprey

Lindsey W.
Resident
6y ago
"It’s a quiet and low key suburb area of Sarasota county. It’s very accessible to I-75 and Nokomis beach and about a 25 minute drive to siesta key beach. "
4
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Mary V.
Resident
6y ago
"I am retired now but my commute to Stickney Point was only about 10 min and downtown was about 25 min during rush hour when there is no construction "
0
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Mary V.
Resident
6y ago
"Pineview School is very close, nice safe area for children. CVS and Publix are also close, as well as Historic Spanish Pointe. The beach is ten minutes or less."
3
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Bob T.
Resident
7y ago
"I don’t commute....retired. There are no sidewalks here and our street has a large amount of speeders making walking dangerous. Some neighbors park on the county right of way destroying our water flow/drainage which has caused flooding here. Many homes are unkept even though there is an active hoa."
14
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Bob T.
Resident
7y ago
"Neighborhood is pet friendly. Wide road we walking dogs. Only problem noticed now is daily construction vehicles speeding in neighborhood."
1
Flag
Larysathor
Visitor
7y ago
"Well, the Mother Nature taking its tall, water level raised over last ten years and a lot of beaches are washed out to nonexistence."
0
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Brenda F. D.
Resident
8y ago
"Neighborhood is beautiful love the area close to everything and beaches and shopping . Local restaurant "
1
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Michelle C.
Resident
8y ago
"I've lived in this neighborhood for twenty years +. My neighbors are the friendliest. We all look out for each other and lend a hand when needed. Can't think of anywhere else I'd want to live."
0
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nancybuscher
11y ago
"This quiet, beautifully landscaped, pet friendly subdivision is close to beaches, shopping, restaurants, cultural events in Sarasota and Venice, beside Oscar Scherer State Park for hickers & boaters, and has easy access to airports by way of US41 & I-75."
0
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info
12y ago
"Centrally located, minutes to beaches and shopping"
1
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bookwoman39
12y ago
"Wonderful community, close to Sarasota and all restaurants, cultural activities, etc. The condo development is a designated bird sanctuary. Nice pools, exercise room, community room. Good neighbors. What the development lacks is diversity. "
0
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trishmainey1111
12y ago
"Osprey Florida is one of the most beautiful, accessible communities in Florida. Ten minutes to the white sands beach and ten minutes to I-75. "
1
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Gail L.
12y ago
"I work here, belong to the club and have lived in the neighborhood for the last 12 years it is one of 5 golf communities I have belonged to and bar none my favorite due to the people that live here. They are multicultural, down to earth and just fabulous. This is a community that rates above the rest . it is very common for folks to move up and down in house sizes and styles as their lifestyles change. Give me a call as I'd love to show you around. "
0
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Browse Osprey, FL homes by type

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Osprey, FL Real Estate & Homes For Sale