Osprey, FL Real Estate & Homes For Sale

134 homes

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NEW - 23 HRS AGO
3D VIEW
$1,475,000
4 Beds
3 Baths
3,246 sqft
1474 Landview Ln,
Osprey, FL 34229
PAT WILLIAMS REALTY, LLC
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NEW - 1 DAY AGO
3D VIEW
$540,000
4 Beds
2 Baths
2,399 sqft
523 Oak Bay Dr,
Osprey, FL 34229
KELLER WILLIAMS ON THE WATER S
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NEW - 1 DAY AGO
3D VIEW
$225,000
2 Beds
2 Baths
1,325 sqft
110 Woodland Pl #110,
Osprey, FL 34229
COLDWELL BANKER REALTY
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NEW - 1 DAY AGO
3D VIEW
$880,000
3 Beds
3 Baths
2,778 sqft
401 N Point Rd #504,
Osprey, FL 34229
MICHAEL SAUNDERS & COMPANY
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NEW - 2 DAYS AGO
3D VIEW
$599,000
3 Beds
2 Baths
2,172 sqft
557 Crane Prairie Way,
Osprey, FL 34229
COLDWELL BANKER REALTY
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NEW
OPEN SUN, 2-4PM
$999,000
3 Beds
2 Baths
2,086 sqft
14041 Bellagio Way #318,
Osprey, FL 34229
COLDWELL BANKER REALTY
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NEW - 2 DAYS AGO
0.41 ACRES
$575,000
143 Osprey Point Dr,
Osprey, FL 34229
COLDWELL BANKER REALTY
NEW - 2 DAYS AGO
3D VIEW
$269,900
2 Beds
2 Baths
1,325 sqft
116 Woodland Pl #116,
Osprey, FL 34229
PAT WILLIAMS REALTY, LLC
NEW - 2 DAYS AGO
3D VIEW
0.76 ACRES
$1,649,000
4 Beds
4 Baths
4,001 sqft
75 Osprey Point Dr,
Osprey, FL 34229
COLDWELL BANKER REALTY
3D VIEW
0.64 ACRES
$1,495,000
3 Beds
3.5 Baths
2,913 sqft
360 N Point Rd,
Osprey, FL 34229
COLDWELL BANKER REALTY
0.59 ACRES
$695,000
216 Osprey Point Dr #24,
Osprey, FL 34229
PREMIER SOTHEBY'S INTERNATIONAL REALTY
3D VIEW
0.27 ACRES
$579,000
3 Beds
2 Baths
2,182 sqft
1367 Thornapple Dr,
Osprey, FL 34229
PREMIER SOTHEBY'S INTERNATIONAL REALTY
3D VIEW
$299,990
2 Beds
2 Baths
1,135 sqft
4296 Expedition Way #104,
Osprey, FL 34229
EXP REALTY LLC
0.44 ACRES
$2,995,000
3 Beds
3.5 Baths
2,665 sqft
14401 Masthead Dr,
Osprey, FL 34229
MICHAEL SAUNDERS & COMPANY
3D VIEW
0.93 ACRES
$4,790,000
4 Beds
5.5 Baths
5,087 sqft
101 Osprey Point Dr,
Osprey, FL 34229
DOUGLAS ELLIMAN
3D VIEW
0.32 ACRES
$1,050,000
3 Beds
2 Baths
2,255 sqft
292 Turquoise Ln,
Osprey, FL 34229
COLDWELL BANKER REALTY
OPEN SUN, 1-4PM
3D VIEW
0.54 ACRES
$1,495,000
4 Beds
3 Baths
3,853 sqft
314 S Shore Dr,
Osprey, FL 34229
HOMECOIN.COM
AUCTION
0.48 ACRES
Est. $1,255,300
3 Beds
3 Baths
3,679 sqft
133 Osprey Point Dr,
Osprey, FL 34229
3D VIEW
$345,000
2 Beds
2 Baths
1,449 sqft
89 Navigation Cir,
Osprey, FL 34229
KW COASTAL LIVING II
3D VIEW
$749,000
3 Beds
2 Baths
2,034 sqft
103 Bishops Court Rd,
Osprey, FL 34229
GENEROUS PROPERTY
3D VIEW
$585,000
4 Beds
3 Baths
2,370 sqft
4424 Conchfish Ln,
Osprey, FL 34229
COLDWELL BANKER REALTY
0.34 ACRES
$739,000
3 Beds
2.5 Baths
2,216 sqft
347 Bayshore Dr,
Osprey, FL 34229
COLDWELL BANKER REALTY
3D VIEW
$195,000
2 Beds
2 Baths
1,199 sqft
320 Tropic Dr,
Osprey, FL 34229
RE/MAX PALM
3D VIEW
0.3 ACRES
$999,000
3 Beds
3 Baths
2,486 sqft
204 Windward Dr,
Osprey, FL 34229
GOLF & BAY PROPERTIES LLC
NEW CONSTRUCTION
3D VIEW
$749,000
3 Beds
2 Baths
1,937 sqft
280 Hidden Bay Dr #302,
Osprey, FL 34229
BERKSHIRE HATHAWAY HOMESERVICE
3D VIEW
$269,000
2 Beds
2 Baths
1,379 sqft
754 Pine Run Dr #754,
Osprey, FL 34229
CALL IT CLOSED INTL REALTY
3D VIEW
0.45 ACRES
$1,289,000
3 Beds
3.5 Baths
3,112 sqft
156 Bishops Court Rd,
Osprey, FL 34229
DOUGLAS ELLIMAN
3D VIEW
$275,000
1 Bed
1 Bath
623 sqft
51 Mac Ewen Dr #12,
Osprey, FL 34229
COLDWELL BANKER REALTY
3D VIEW
0.37 ACRES
$3,295,000
3 Beds
4.5 Baths
2,572 sqft
135 Tina Island Dr,
Osprey, FL 34229
GENEROUS PROPERTY
FOR SALE BY OWNER
$429,000
3 Beds
3 Baths
1,581 sqft
4288 Expedition Way,
Osprey, FL 34229
3D VIEW
30.5 ACRES
$294,900
2 Beds
2 Baths
1,244 sqft
184 Explorer Dr,
Osprey, FL 34229
DALTON WADE INC
3D VIEW
$850,000
3 Beds
3.5 Baths
3,771 sqft
6100 Jessie Harbor Dr #202,
Osprey, FL 34229
CORCORAN DWELLINGS REALTY
OPEN SAT, 1-4PM
3D VIEW
0.4 ACRES
$1,950,000
5 Beds
5.5 Baths
4,885 sqft
97 Sugar Mill Dr,
Osprey, FL 34229
PALM PARADISE REALTY GROUP
3D VIEW
$535,000
3 Beds
2 Baths
2,004 sqft
4429 Conchfish Ln,
Osprey, FL 34229
EXP REALTY, LLC
3D VIEW
$1,175,000
3 Beds
3 Baths
2,187 sqft
14021 Bellagio Way #404,
Osprey, FL 34229
PREMIER SOTHEBYS INTL REALTY
$75,000
Glenwood Ave #182,
Osprey, FL 34229
COLDWELL BANKER REALTY
$75,000
Glenwood Ave #181,
Osprey, FL 34229
COLDWELL BANKER REALTY
3D VIEW
$550,000
3 Beds
2 Baths
2,074 sqft
1361 New Forest Ln,
Osprey, FL 34229
NEXTHOME EXCELLENCE
0.53 ACRES
$999,500
3 Beds
2.5 Baths
2,502 sqft
113 Burney Rd,
Osprey, FL 34229
GENEROUS PROPERTY
OPEN SUN, 12:30-3PM
3D VIEW
$735,000
2 Beds
2 Baths
2,143 sqft
5100 Jessie Harbor Dr #304,
Osprey, FL 34229
COLDWELL BANKER REALTY

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 $655,882

Month	Median home value
June 2025	$691k
July 2025	$683k
August 2025	$674k
September 2025	$667k
October 2025	$663k
November 2025	$660k
December 2025	$658k
January 2026	$658k
February 2026	$659k
March 2026	$659k
April 2026	$658k
May 2026	$656k

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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 10 new listings in Osprey, FL and 134 homes for sale.

Home Size	Home Value*
2 bedrooms (24 homes)	$321,391
3 bedrooms (61 homes)	$681,190
4 bedrooms (22 homes)	$926,539

*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. "
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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 "
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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
6y 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
6y ago
"Neighborhood is pet friendly. Wide road we walking dogs. Only problem noticed now is daily construction vehicles speeding in neighborhood."
1
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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
7y ago
"Neighborhood is beautiful love the area close to everything and beaches and shopping . Local restaurant "
1
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Michelle C.
Resident
7y 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."
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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
11y ago
"Centrally located, minutes to beaches and shopping"
1
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bookwoman39
11y 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. "
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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. "
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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

134 homes

Osprey, FL Real Estate Trends

Affordability of Living in Osprey, FL

Average Home Value in Osprey, FL, by Home Size

What Locals Say about Osprey

Nearby Real Estate

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