Osprey Houses for Sale · Page 2

67 houses for sale in Osprey, median asking price $1,295,000, mostly $546,000 – $3,700,000. Single-family houses. Osprey (ZIP 34229). Nokomis has its own page. As of Oct 9, 2026.

1216 CASEY KEY ROAD, OSPREY
Active

$9,750,000

1216 CASEY KEY ROAD

OSPREY, FL 34229

5 bed
8 bath
8,050 sqft

MLS# A4704643 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

583 PINE RANCH EAST ROAD, OSPREY
Active Under Contract

$529,000

583 PINE RANCH EAST ROAD

OSPREY, FL 34229

4 bed
2 bath
2,203 sqft

MLS# A4704589 · Listing courtesy of GALLERY PROPERTIES INTERNATIONAL

226 SAINT JAMES PARK, OSPREY
Active

$1,495,000

226 SAINT JAMES PARK

OSPREY, FL 34229

3 bed
3 bath
2,591 sqft

MLS# A4704489 · Listing courtesy of KELLER WILLIAMS ON THE WATER S

154 LOOKOUT POINT DRIVE, OSPREY
Active

$2,095,000

154 LOOKOUT POINT DRIVE

OSPREY, FL 34229

4 bed
4 bath
4,578 sqft

MLS# TB8543439 · Listing courtesy of FLAT FEE MLS REALTY

296 PINE RANCH TRAIL, OSPREY
Active

$1,100,000

296 PINE RANCH TRAIL

OSPREY, FL 34229

5 bed
4 bath
3,354 sqft

MLS# A4704317 · Listing courtesy of BEYOND REALTY LLC

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

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

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

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

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

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

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

75 OSPREY POINT DRIVE, OSPREY
Active

$1,595,000

75 OSPREY POINT DRIVE

OSPREY, FL 34229

4 bed
4 bath
4,001 sqft

MLS# A4695145 · Listing courtesy of COLDWELL BANKER REALTY

360 N POINT ROAD, OSPREY
Active

$1,495,000

360 N POINT ROAD

OSPREY, FL 34229

3 bed
4 bath
2,913 sqft

MLS# A4695959 · Listing courtesy of COLDWELL BANKER REALTY

101 OSPREY POINT DRIVE, OSPREY
Active

$4,790,000

101 OSPREY POINT DRIVE

OSPREY, FL 34229

4 bed
6 bath
5,087 sqft

MLS# A4694716 · Listing courtesy of DOUGLAS ELLIMAN

103 BISHOPS COURT ROAD, OSPREY
Active

$699,000

103 BISHOPS COURT ROAD

OSPREY, FL 34229

3 bed
2 bath
2,034 sqft

MLS# A4694468 · Listing courtesy of GENEROUS PROPERTY

156 BISHOPS COURT ROAD, OSPREY
Active

$1,289,000

156 BISHOPS COURT ROAD

OSPREY, FL 34229

3 bed
4 bath
3,112 sqft

MLS# A4691664 · Listing courtesy of DOUGLAS ELLIMAN

135 TINA ISLAND DRIVE, OSPREY
Active

$3,295,000

135 TINA ISLAND DRIVE

OSPREY, FL 34229

3 bed
5 bath
2,572 sqft

MLS# A4692366 · Listing courtesy of GENEROUS PROPERTY

97 SUGAR MILL DRIVE, OSPREY
Active

$1,950,000

97 SUGAR MILL DRIVE

OSPREY, FL 34229

5 bed
6 bath
4,885 sqft

MLS# A4691789 · Listing courtesy of PALM PARADISE REALTY GROUP

4429 CONCHFISH LANE, OSPREY
Active

$499,999

4429 CONCHFISH LANE

OSPREY, FL 34229

3 bed
2 bath
2,004 sqft

MLS# A4689967 · Listing courtesy of EXP REALTY, LLC

More in Osprey

Houses for Sale nearby

Questions about Osprey Houses for Sale

How many houses are for sale in Osprey?

67 houses 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 houses in Osprey?

The median asking price is $1,295,000; most are listed between $546,000 and $3,700,000. 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 houses?

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, 4:30 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