Osprey Homes for Sale · Page 2

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.

385 N POINT ROAD #301, OSPREY
Pending

$750,000

385 N POINT ROAD #301

OSPREY, FL 34229

3 bed
3 bath
2,594 sqft

MLS# A4706542 · Listing courtesy of COLDWELL BANKER REALTY

3621 N POINT ROAD #403, OSPREY
Active

$700,000

3621 N POINT ROAD #403

OSPREY, FL 34229

3 bed
3 bath
2,680 sqft

MLS# A4705730 · 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

109 WOODLAND PLACE, OSPREY
Active

$244,900

109 WOODLAND PLACE

OSPREY, FL 34229

2 bed
2 bath
1,223 sqft

MLS# A4705745 · Listing courtesy of PREFERRED SHORE 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

401 N POINT ROAD #303, OSPREY
Pending

$445,000

401 N POINT ROAD #303

OSPREY, FL 34229

3 bed
3 bath
2,203 sqft

MLS# A4706051 · 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

2046 CORDES STREET, OSPREY
Active

$565,000

2046 CORDES STREET

OSPREY, FL 34229

3 bed
2 bath
1,705 sqft

MLS# A4705136 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

401 N POINT ROAD #903, OSPREY
Pending

$1,250,000

401 N POINT ROAD #903

OSPREY, FL 34229

3 bed
3 bath
2,203 sqft

MLS# A4705080 · Listing courtesy of COLDWELL BANKER REALTY

210 PATTERSON AVENUE, OSPREY
Active

$950,000

210 PATTERSON AVENUE

OSPREY, FL 34229

3 bed
2 bath
2,084 sqft

MLS# A4704911 · Listing courtesy of REALTY ONE GROUP MVP

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

401 N POINT ROAD #701, OSPREY
Pending

$1,480,000

401 N POINT ROAD #701

OSPREY, FL 34229

3 bed
3 bath
2,594 sqft

MLS# A4704870 · Listing courtesy of COLDWELL BANKER REALTY

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

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.

Listings courtesy of Stellar MLS as distributed by MLS GRID

Based on information submitted to the MLS GRID as of Oct 9, 2026, 5:00 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