Osprey Pool Homes for Sale · Page 2

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.

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

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

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

280 HIDDEN BAY DRIVE #302, OSPREY
Active

$719,000

280 HIDDEN BAY DRIVE #302

OSPREY, FL 34229

3 bed
2 bath
1,937 sqft

MLS# A4690813 · Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICE

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

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

759 FORDINGBRIDGE WAY, OSPREY
Active

$700,000

759 FORDINGBRIDGE WAY

OSPREY, FL 34229

4 bed
4 bath
2,950 sqft

MLS# O6399774 · Listing courtesy of BEYCOME OF FLORIDA LLC

1527 BUOY LANE, OSPREY
Active

$1,100,000

1527 BUOY LANE

OSPREY, FL 34229

3 bed
3 bath
2,830 sqft

MLS# A4688266 · Listing courtesy of BRIGHT REALTY

313 LOOKOUT POINT DRIVE, OSPREY
Active

$5,299,999

313 LOOKOUT POINT DRIVE

OSPREY, FL 34229

4 bed
5 bath
5,337 sqft

MLS# A4688995 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

14401 MASTHEAD DRIVE, OSPREY
Active Under Contract

$2,850,000

14401 MASTHEAD DRIVE

OSPREY, FL 34229

3 bed
4 bath
2,665 sqft

MLS# A4684834 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

49 OSPREY POINT DRIVE, OSPREY
Active

$2,399,000

49 OSPREY POINT DRIVE

OSPREY, FL 34229

4 bed
4 bath
3,953 sqft

MLS# A4671762 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

538 DOVE POINTE DRIVE, OSPREY
Active Under Contract

$1,950,000

538 DOVE POINTE DRIVE

OSPREY, FL 34229

4 bed
6 bath
4,346 sqft

MLS# A4669491 · Listing courtesy of GENEROUS PROPERTY

18 CASEY KEY ROAD, OSPREY
Active

$1,750,000

18 CASEY KEY ROAD

OSPREY, FL 34229

3 bed
2 bath
1,977 sqft

MLS# A4669083 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

121 CASEY KEY ROAD, OSPREY
Active

$6,100,000

121 CASEY KEY ROAD

OSPREY, FL 34229

4 bed
6 bath
4,096 sqft

MLS# A4667263 · Listing courtesy of DOUGLAS ELLIMAN

21 BAYHEAD LANE, OSPREY
Active

$789,000

21 BAYHEAD LANE

OSPREY, FL 34229

3 bed
2 bath
2,246 sqft

MLS# A4664085 · Listing courtesy of COLDWELL BANKER REALTY

599 PINE RANCH EAST ROAD, OSPREY
Active

$815,000

599 PINE RANCH EAST ROAD

OSPREY, FL 34229

3 bed
2 bath
2,188 sqft

MLS# A4660895 · Listing courtesy of GENEROUS PROPERTY

852 MACEWEN DRIVE, OSPREY
Active

$2,395,000

852 MACEWEN DRIVE

OSPREY, FL 34229

3 bed
4 bath
4,519 sqft

MLS# A4659276 · Listing courtesy of GENEROUS PROPERTY

110 PINE AVENUE, OSPREY
Active

$649,000

110 PINE AVENUE

OSPREY, FL 34229

3 bed
2 bath
2,058 sqft

MLS# A4646339 · Listing courtesy of BRIGHT REALTY

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, 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