Osprey Homes for Sale · Page 3

127 homes for sale in Osprey, median asking price $750,000, mostly $203,000 – $2,640,000. All residential listings: houses, condos, townhomes and villas. Osprey (ZIP 34229). Nokomis has its own page. As of Oct 9, 2026.

586 OAK BAY DRIVE, OSPREY
Active Under Contract

$649,000

586 OAK BAY DRIVE

OSPREY, FL 34229

3 bed
2 bath
2,084 sqft

MLS# A4703807 · Listing courtesy of WHITE SANDS REALTY GROUP FL

907 EAGLE ISLE COURT, OSPREY
Active Under Contract

$1,100,000

907 EAGLE ISLE COURT

OSPREY, FL 34229

4 bed
3 bath
3,984 sqft

MLS# A4703534 · Listing courtesy of CENTURY 21 ROSEBAY

1819 HIGHLAND ROAD, OSPREY
Active

$319,000

1819 HIGHLAND ROAD

OSPREY, FL 34229

2 bed
3 bath
1,240 sqft

MLS# A4703963 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

1140 BEACHCOMBER COURT #11, OSPREY
Active

$540,000

1140 BEACHCOMBER COURT #11

OSPREY, FL 34229

3 bed
3 bath
2,040 sqft

MLS# W7888943 · Listing courtesy of LISTWITHFREEDOM.COM

447 MACEWEN DRIVE, OSPREY
Pending

$2,750,000

447 MACEWEN DRIVE

OSPREY, FL 34229

4 bed
5 bath
5,323 sqft

MLS# A4703990 · Listing courtesy of COLDWELL BANKER REALTY

222 SAINT JAMES PARK, OSPREY
Pending

$1,800,000

222 SAINT JAMES PARK

OSPREY, FL 34229

3 bed
4 bath
3,665 sqft

MLS# A4703804 · Listing courtesy of COLDWELL BANKER REALTY

5100 JESSIE HARBOR DRIVE #404, OSPREY
Active

$599,000

5100 JESSIE HARBOR DRIVE #404

OSPREY, FL 34229

2 bed
2 bath
2,143 sqft

MLS# A4703484 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

409 POINT ROAD #803, OSPREY
Active

$985,000

409 POINT ROAD #803

OSPREY, FL 34229

3 bed
3 bath
2,203 sqft

MLS# A4703407 · Listing courtesy of GENEROUS PROPERTY

264 WOODS POINT ROAD #264, OSPREY
Active Under Contract

$695,000

264 WOODS POINT ROAD #264

OSPREY, FL 34229

3 bed
3 bath
2,837 sqft

MLS# A4703025 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

299 TURQUOISE LANE, OSPREY
Active

$699,000

299 TURQUOISE LANE

OSPREY, FL 34229

3 bed
2 bath
2,328 sqft

MLS# A4701662 · Listing courtesy of BRIGHT REALTY

260 HIDDEN BAY DRIVE #402, OSPREY
Active

$775,000

260 HIDDEN BAY DRIVE #402

OSPREY, FL 34229

3 bed
3 bath
1,950 sqft

MLS# A4701000 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

1036 OAK MEADOW LANE, OSPREY
Active

$630,000

1036 OAK MEADOW LANE

OSPREY, FL 34229

4 bed
2 bath
2,186 sqft

MLS# A4701532 · Listing courtesy of BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

701 PINE RUN DRIVE #701, OSPREY
Pending

$151,000

701 PINE RUN DRIVE #701

OSPREY, FL 34229

1 bed
1 bath
586 sqft

MLS# A4700416 · Listing courtesy of PAT WILLIAMS REALTY, LLC

547 MEADOW SWEET CIRCLE, OSPREY
Pending

$550,000

547 MEADOW SWEET CIRCLE

OSPREY, FL 34229

3 bed
2 bath
1,731 sqft

MLS# A4701316 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

570 BLACKBURN POINT ROAD #36, OSPREY
Active

$99,500

570 BLACKBURN POINT ROAD #36

OSPREY, FL 34229

0 bed
0 bath
0 sqft

MLS# A4700865 · Listing courtesy of BRIGHT REALTY

329 BAY VISTA AVENUE, OSPREY
Active Under Contract

$399,000

329 BAY VISTA AVENUE

OSPREY, FL 34229

2 bed
2 bath
1,346 sqft

MLS# A4699464 · Listing courtesy of THE SHORELINE FL REALTY LLC

Address available upon request, OSPREY
Active Under Contract

$824,900

Address available upon request

OSPREY, FL 34229

4 bed
3 bath
2,607 sqft

MLS# A4699089 · Listing courtesy of DALTON WADE INC

2309 JESSIE HARBOR DRIVE #2402, OSPREY
Active

$480,000

2309 JESSIE HARBOR DRIVE #2402

OSPREY, FL 34229

3 bed
3 bath
2,006 sqft

MLS# A4698434 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

1495 LANDVIEW LANE, OSPREY
Active Under Contract

$760,000

1495 LANDVIEW LANE

OSPREY, FL 34229

3 bed
2 bath
2,474 sqft

MLS# A4697993 · Listing courtesy of PAT WILLIAMS REALTY, LLC

206 FOUR KNOT LANE, OSPREY
Active

$1,690,000

206 FOUR KNOT LANE

OSPREY, FL 34229

3 bed
2 bath
2,411 sqft

MLS# A4695429 · Listing courtesy of REALTY ONE GROUP MVP

570 BLACKBURN POINT ROAD #23, OSPREY
Active

$89,000

570 BLACKBURN POINT ROAD #23

OSPREY, FL 34229

0 bed
0 bath
0 sqft

MLS# A4697977 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

7204 JESSIE HARBOR DRIVE #7204, OSPREY
Active

$395,000

7204 JESSIE HARBOR DRIVE #7204

OSPREY, FL 34229

2 bed
2 bath
1,255 sqft

MLS# A4697473 · Listing courtesy of GENEROUS PROPERTY

110 WOODLAND PLACE #110, OSPREY
Active Under Contract

$215,000

110 WOODLAND PLACE #110

OSPREY, FL 34229

2 bed
2 bath
1,325 sqft

MLS# A4696738 · Listing courtesy of COLDWELL BANKER REALTY

116 WOODLAND PLACE #116, OSPREY
Active

$249,900

116 WOODLAND PLACE #116

OSPREY, FL 34229

2 bed
2 bath
1,325 sqft

MLS# A4696616 · Listing courtesy of PAT WILLIAMS REALTY, LLC

More in Osprey

Homes for Sale nearby

Questions about Osprey Homes for Sale

How many homes are for sale in Osprey?

127 homes are listed on this site as of Oct 9, 2026, from Stellar MLS. The list updates every hour.

What is the median asking price of homes in Osprey?

The median asking price is $750,000; most are listed between $203,000 and $2,640,000. These are asking prices, not sale prices.

Can George help me buy in Osprey?

Yes. George Predescu, REALTOR® with Horizon Realty International, can set up showings for any listing here, including ones listed by other brokers. Call or text (941) 899-3045.

Want to see one of these homes?

George Predescu, REALTOR® with Horizon Realty International, can answer questions and set up showings.

Call (941) 899-3045Text GeorgeSend a message

Listings courtesy of Stellar MLS as distributed by MLS GRID

Based on information submitted to the MLS GRID as of Oct 9, 2026, 5:30 PM EDT. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some IDX listings have been excluded from this website. Full IDX / DMCA disclaimer