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Homes for Sale in Osprey
Sarasota County, Florida — Updated daily from Stellar MLS
133
Active Listings
$931,821
Avg. List Price
$55,000 – $6,475,000
Price Range
94
Avg. Days on Market
Latest Listings in Osprey
Showing 48 of 133 active homes for sale in Osprey, Sarasota County.
Active$685,000
730 FORDINGBRIDGE WAY
OSPREY, FL 34229
3 Bed2 Bath2,182 sq ft Sqft
Active$320,000
4213 EXPEDITION WAY
OSPREY, FL 34229
3 Bed2 Bath1,430 sq ft Sqft
Active$1,850,000
206 FOUR KNOT LANE
OSPREY, FL 34229
3 Bed2 Bath2,411 sq ft Sqft
Active$655,000
816 SHADOW BAY WAY
OSPREY, FL 34229
3 Bed3 Bath2,251 sq ft Sqft
Active$725,000
5100 JESSIE HARBOR DRIVE
OSPREY, FL 34229
2 Bed2 Bath2,143 sq ft Sqft
Active$1,475,000
1474 LANDVIEW LANE
OSPREY, FL 34229
4 Bed3 Bath3,246 sq ft Sqft
Active$799,900
1495 LANDVIEW LANE
OSPREY, FL 34229
3 Bed2 Bath2,474 sq ft Sqft
Active$359,000
2251 JESSIE HARBOR DRIVE
OSPREY, FL 34229
2 Bed2 Bath1,400 sq ft Sqft
Active$139,900
0 WESTVIEW DRIVE
OSPREY, FL 34229
0 Bath
Active$497,000
2309 JESSIE HARBOR DRIVE
OSPREY, FL 34229
3 Bed3 Bath2,006 sq ft Sqft
Active$609,900
619 OAK RIVER COURT
OSPREY, FL 34229
3 Bed2 Bath2,047 sq ft Sqft
Active$249,000
480 BLACKBURN POINT ROAD
OSPREY, FL 34229
0 Bath
Active$328,000
173 NAVIGATION CIRCLE
OSPREY, FL 34229
3 Bed2 Bath1,528 sq ft Sqft
Active$55,000
GLENWOOD AVENUE
OSPREY, FL 34229
0 Bath
Active$55,000
GLENWOOD AVENUE
OSPREY, FL 34229
0 Bath
Active$694,000
260 HIDDEN BAY DRIVE
OSPREY, FL 34229
2 Bed3 Bath1,950 sq ft Sqft
Active$489,000
786 SARABAY ROAD
OSPREY, FL 34229
2 Bed2 Bath1,555 sq ft Sqft
Active$2,199,900
180 LOOKOUT POINT DRIVE
OSPREY, FL 34229
5 Bed4 Bath3,236 sq ft Sqft
Active$850,000
6100 JESSIE HARBOR DRIVE
OSPREY, FL 34229
3 Bed4 Bath3,771 sq ft Sqft
Active$427,000
212 WASHINGTON AVENUE
OSPREY, FL 34229
3 Bed2 Bath1,478 sq ft Sqft
Active$289,900
1801 HIGHLAND ROAD
OSPREY, FL 34229
2 Bed2 Bath1,165 sq ft Sqft
Active$449,000
811 SARABAY ROAD
OSPREY, FL 34229
2 Bed1 Bath1,211 sq ft Sqft
Active$695,000
401 N POINT ROAD
OSPREY, FL 34229
3 Bed3 Bath2,778 sq ft Sqft
Active$175,000
14 OLD VENICE ROAD
OSPREY, FL 34229
0 Bath
Active$215,000
110 WOODLAND PLACE
OSPREY, FL 34229
2 Bed2 Bath1,325 sq ft Sqft
Active$739,000
347 BAYSHORE DRIVE
OSPREY, FL 34229
3 Bed3 Bath2,216 sq ft Sqft
Active$825,000
3820 PARROT BAY COURT
OSPREY, FL 34229
0 Bath
Active$98,000
570 BLACKBURN POINT ROAD
OSPREY, FL 34229
0 Bath
Active$1,495,000
422 BLUE GARDEN LANE
OSPREY, FL 34229
3 Bed4 Bath3,872 sq ft Sqft
Active$318,000
4304 EXPEDITION WAY WAY
OSPREY, FL 34229
3 Bed2 Bath1,528 sq ft Sqft
Active$425,000
764 SARABAY ROAD
OSPREY, FL 34229
2 Bed2 Bath1,392 sq ft Sqft
Active$1,395,000
3603 POINT ROAD
OSPREY, FL 34229
3 Bed3 Bath2,545 sq ft Sqft
Active$999,000
14041 BELLAGIO WAY
OSPREY, FL 34229
3 Bed2 Bath2,086 sq ft Sqft
Active$548,000
4428 CONCHFISH LANE
OSPREY, FL 34229
4 Bed2 Bath1,861 sq ft Sqft
Active$2,189,000
433 MACEWEN DRIVE
OSPREY, FL 34229
4 Bed4 Bath4,012 sq ft Sqft
Active$1,289,000
156 BISHOPS COURT ROAD
OSPREY, FL 34229
3 Bed4 Bath3,112 sq ft Sqft
Active$585,000
4424 CONCHFISH LANE
OSPREY, FL 34229
4 Bed3 Bath2,370 sq ft Sqft
Active$3,640,000
854 MACEWEN DRIVE
OSPREY, FL 34229
4 Bed6 Bath9,081 sq ft Sqft
Active$2,995,000
14401 MASTHEAD DRIVE
OSPREY, FL 34229
3 Bed4 Bath2,665 sq ft Sqft
Active$1,095,000
403 LONGBOW TRAIL
OSPREY, FL 34229
4 Bed3 Bath2,770 sq ft Sqft
Active$259,000
754 PINE RUN DRIVE
OSPREY, FL 34229
2 Bed2 Bath1,379 sq ft Sqft
Active$254,900
116 WOODLAND PLACE
OSPREY, FL 34229
2 Bed2 Bath1,325 sq ft Sqft
Active$320,000
89 NAVIGATION CIRCLE
OSPREY, FL 34229
2 Bed2 Bath1,449 sq ft Sqft
Active$449,000
429 PATTERSON AVENUE
OSPREY, FL 34229
3 Bed1 Bath1,173 sq ft Sqft
Active$269,000
SARABAY ROAD
OSPREY, FL 34229
0 Bath
Active$2,249,000
362 MACEWEN DRIVE
OSPREY, FL 34229
4 Bed4 Bath4,117 sq ft Sqft
Active$530,000
4429 CONCHFISH LANE
OSPREY, FL 34229
3 Bed2 Bath2,004 sq ft Sqft
Active$6,475,000
121 CASEY KEY ROAD
OSPREY, FL 34229
5 Bed6 Bath4,096 sq ft Sqft
Listing information provided by Stellar MLS. IDX information is for personal, non-commercial use only. Data is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal.
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About Osprey, Florida
Osprey is a sought-after community in Sarasota County, Florida, spanning ZIP codes 34229. Quiet bayfront community between Sarasota and Venice with nature preserves. From first-time buyers to seasoned investors, Osprey offers something for everyone.
Barrett Henry is a licensed Broker Associate with REMAX Collective and brings 23+ years of real estate experience to every transaction. As a local market expert, Barrett helps buyers and sellers in Osprey navigate pricing, negotiations, and inspections with confidence.
Ready to explore homes in Osprey? Call (813) 733-7907 or use the contact form below to get started. Barrett will send you a curated list of Osprey properties that match your criteria.
Recently Sold Homes in Osprey
See what homes recently sold for in Osprey to understand current market values.
Closed$11,500,000
1588 CASEY KEY ROAD
OSPREY, FL 34229
5 Bed8 Bath7,760 sq ft Sqft
Closed$10,500,000
1544 CASEY KEY ROAD
OSPREY, FL 34229
6 Bed8 Bath6,997 sq ft Sqft
Closed$9,500,000
1588 CASEY KEY ROAD
OSPREY, FL 34229
6 Bed8 Bath7,760 sq ft Sqft
Closed$10,000,000
712 CASEY KEY ROAD
OSPREY, FL 34229
8 Bed10 Bath13,553 sq ft Sqft
Closed$7,984,000
13 CASEY KEY ROAD
OSPREY, FL 34229
4 Bed6 Bath6,387 sq ft Sqft
Closed$8,250,000
SARABAY ROAD
OSPREY, FL 34229
0 Bath
Closed$3,500
DRIVE
OSPREY, FL 34229
3 Bed3 Bath2,360 sq ft Sqft
Closed$7,650,000
316 CASEY KEY ROAD
OSPREY, FL 34229
5 Bed7 Bath7,121 sq ft Sqft
Homes for Rent in Osprey
Showing 12 of 28 rental listings in Osprey, Sarasota County.
Active$4,500
919 SCHERER WAY
OSPREY, FL 34229
4 Bed3 Bath2,290 sq ft Sqft
Active$2,250
4219 FRONTIER WAY
OSPREY, FL 34229
2 Bed2 Bath1,244 sq ft Sqft
Active$5,500
6100 JESSIE HARBOR DRIVE
OSPREY, FL 34229
3 Bed4 Bath3,771 sq ft Sqft
Active$2,250
4304 EXPEDITION WAY WAY
OSPREY, FL 34229
3 Bed2 Bath1,528 sq ft Sqft
Active$4,850
260 HIDDEN BAY DRIVE
OSPREY, FL 34229
3 Bed3 Bath2,168 sq ft Sqft
Active$3,150
341 BAYSHORE DRIVE
OSPREY, FL 34229
3 Bed2 Bath1,897 sq ft Sqft
Active$4,500
124 TURQUOISE LANE
OSPREY, FL 34229
3 Bed2 Bath2,306 sq ft Sqft
Active$3,980
254 BURNEY RD
OSPREY, FL 34229
5 Bed5 Bath3,050 sq ft Sqft
Active$3,980
246 BURNEY RD
OSPREY, FL 34229
5 Bed5 Bath3,050 sq ft Sqft
Active$4,500
152 NAVIGATION CIRCLE
OSPREY, FL 34229
3 Bed2 Bath1,528 sq ft Sqft
Active$2,250
51 MAC EWEN DRIVE
OSPREY, FL 34229
1 Bed1 Bath595 sq ft Sqft
Active$2,150
184 EXPLORER DRIVE
OSPREY, FL 34229
2 Bed2 Bath1,135 sq ft Sqft
Frequently Asked Questions About Osprey
What is the average home price in Osprey, FL?
Home prices in Osprey vary by neighborhood, property type, and condition. Browse current active listings above for the most up-to-date pricing. Contact Barrett Henry at (813) 733-7907 for a personalized market analysis.
Is Osprey a good place to live?
Osprey is located in Sarasota County, Florida. Quiet bayfront community between Sarasota and Venice with nature preserves. With access to Tampa Bay's job market, beaches, and amenities, Osprey is a popular choice for families, retirees, and investors.
How do I buy a home in Osprey?
Start by getting pre-approved for a mortgage, then work with a local REALTOR® who knows the Osprey market. Barrett Henry and The NOW Team have 23+ years of experience helping buyers in Sarasota County. Call (813) 733-7907 to get started.
What ZIP codes are in Osprey?
Osprey covers ZIP codes 34229. Each ZIP code may include different neighborhoods and school zones.
Nearby Communities
Looking for homes in Osprey?
Barrett Henry, REALTOR® — 23+ years of real estate experience