Osprey Pool Homes for Sale

52 homes with a private pool for sale in Osprey, median asking price $1,593,000, mostly $699,000 – $4,501,000. Osprey (ZIP 34229). Nokomis has its own page. As of Oct 9, 2026.

366 CREEK COURT, OSPREY
Active

$1,049,000

366 CREEK COURT

OSPREY, FL 34229

4 bed
3 bath
2,775 sqft

MLS# A4708943 · Listing courtesy of KELLER WILLIAMS ON THE WATER S

422 BLUE GARDEN LANE, OSPREY
Active

$1,445,000

422 BLUE GARDEN LANE

OSPREY, FL 34229

3 bed
4 bath
3,872 sqft

MLS# A4707058 · Listing courtesy of COLDWELL BANKER REALTY

275 LOOKOUT POINT DRIVE, OSPREY
Active

$4,590,000

275 LOOKOUT POINT DRIVE

OSPREY, FL 34229

5 bed
5 bath
5,279 sqft

MLS# A4707430 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

256 TURQUOISE LANE, OSPREY
Pending

$995,000

256 TURQUOISE LANE

OSPREY, FL 34229

3 bed
2 bath
2,351 sqft

MLS# A4707269 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

155 SEA ANCHOR DRIVE, OSPREY
Pending

$895,000

155 SEA ANCHOR DRIVE

OSPREY, FL 34229

3 bed
3 bath
2,683 sqft

MLS# A4707489 · Listing courtesy of PAT WILLIAMS REALTY, LLC

1104 MALLARD MARSH DRIVE, OSPREY
Active Under Contract

$799,000

1104 MALLARD MARSH DRIVE

OSPREY, FL 34229

3 bed
3 bath
2,678 sqft

MLS# A4697695 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

650 OAKS CREEK COURT, OSPREY
Active

$3,700,000

650 OAKS CREEK COURT

OSPREY, FL 34229

4 bed
4 bath
4,314 sqft

MLS# A4707301 · Listing courtesy of COLDWELL BANKER REALTY

256 SUGAR MILL, OSPREY
Active

$1,399,000

256 SUGAR MILL

OSPREY, FL 34229

3 bed
3 bath
2,695 sqft

MLS# A4707187 · Listing courtesy of KIMBERLITE WEST REALTY LLC

324 OSPREY POINT DRIVE, OSPREY
Active

$3,700,000

324 OSPREY POINT DRIVE

OSPREY, FL 34229

5 bed
5 bath
6,234 sqft

MLS# A4706333 · Listing courtesy of COLDWELL BANKER REALTY

130 WILLOW BEND WAY, OSPREY
Pending

$669,900

130 WILLOW BEND WAY

OSPREY, FL 34229

4 bed
3 bath
2,683 sqft

MLS# TB8548160 · Listing courtesy of RE/MAX ALLIANCE GROUP

700 SHADOW BAY WAY, OSPREY
Active

$655,000

700 SHADOW BAY WAY

OSPREY, FL 34229

3 bed
3 bath
2,792 sqft

MLS# O6442446 · Listing courtesy of KARA MONEY LLC

662 FERNWALK LANE, OSPREY
Pending

$2,800,000

662 FERNWALK LANE

OSPREY, FL 34229

4 bed
4 bath
4,188 sqft

MLS# A4706319 · Listing courtesy of COLDWELL BANKER REALTY

402 MACEWEN DRIVE, OSPREY
Active

$1,590,000

402 MACEWEN DRIVE

OSPREY, FL 34229

3 bed
4 bath
3,565 sqft

MLS# A4706228 · Listing courtesy of COLDWELL BANKER REALTY

141 SUGAR MILL DRIVE, OSPREY
Active

$1,700,000

141 SUGAR MILL DRIVE

OSPREY, FL 34229

3 bed
3 bath
3,118 sqft

MLS# A4705716 · Listing courtesy of COLDWELL BANKER REALTY

362 MACEWEN DRIVE, OSPREY
Pending

$2,175,000

362 MACEWEN DRIVE

OSPREY, FL 34229

4 bed
4 bath
4,117 sqft

MLS# A4705572 · Listing courtesy of COLDWELL BANKER REALTY

1417 LANDVIEW LANE, OSPREY
Active

$1,399,000

1417 LANDVIEW LANE

OSPREY, FL 34229

4 bed
4 bath
3,255 sqft

MLS# A4705553 · Listing courtesy of PAT WILLIAMS REALTY, LLC

453 SHORE DRIVE, OSPREY
Active Under Contract

$499,999

453 SHORE DRIVE

OSPREY, FL 34229

3 bed
3 bath
2,422 sqft

MLS# O6439571 · Listing courtesy of RE/MAX PRIME PROPERTIES

1328 THORNAPPLE DRIVE, OSPREY
Active

$749,900

1328 THORNAPPLE DRIVE

OSPREY, FL 34229

3 bed
2 bath
2,174 sqft

MLS# A4705435 · Listing courtesy of RIVER HILLS PROPERTIES, LLC B

794 LYTHAM CIRCLE, OSPREY
Pending

$2,600,000

794 LYTHAM CIRCLE

OSPREY, FL 34229

4 bed
4 bath
4,450 sqft

MLS# A4705432 · Listing courtesy of COLDWELL BANKER REALTY

112 OSPREY POINT DRIVE, OSPREY
Active Under Contract

$6,449,000

112 OSPREY POINT DRIVE

OSPREY, FL 34229

6 bed
6 bath
8,621 sqft

MLS# A4702047 · Listing courtesy of DOUGLAS ELLIMAN

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

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

More in Osprey

Pool Homes for Sale nearby

Questions about Osprey Pool Homes for Sale

How many homes with a private pool are for sale in Osprey?

52 homes with a private pool 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 with a private pool in Osprey?

The median asking price is $1,593,000; most are listed between $699,000 and $4,501,000. 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 with a private pool?

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, 3:15 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