Osprey Homes for Sale · Page 5

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.

570 BLACKBURN POINT ROAD #26, OSPREY
Active

$36,000

570 BLACKBURN POINT ROAD #26

OSPREY, FL 34229

0 bed
0 bath
0 sqft

MLS# A4680901 · Listing courtesy of BRIGHT REALTY

14021 BELLAGIO WAY #309, OSPREY
Active

$879,000

14021 BELLAGIO WAY #309

OSPREY, FL 34229

3 bed
3 bath
2,199 sqft

MLS# A4681589 · Listing courtesy of COMPASS FLORIDA, LLC

3621 N POINT ROAD #301, OSPREY
Active

$525,000

3621 N POINT ROAD #301

OSPREY, FL 34229

3 bed
3 bath
2,680 sqft

MLS# A4681290 · Listing courtesy of COLDWELL BANKER REALTY

401 POINT ROAD #1001, OSPREY
Active

$1,995,000

401 POINT ROAD #1001

OSPREY, FL 34229

3 bed
3 bath
3,029 sqft

MLS# A4679998 · Listing courtesy of GENEROUS PROPERTY

242 HIDDEN BAY DRIVE #602, OSPREY
Active

$700,000

242 HIDDEN BAY DRIVE #602

OSPREY, FL 34229

2 bed
2 bath
1,932 sqft

MLS# A4678883 · Listing courtesy of FIRST LIGHT REAL ESTATE

385 N POINT ROAD #304, OSPREY
Active

$1,100,000

385 N POINT ROAD #304

OSPREY, FL 34229

3 bed
3 bath
2,778 sqft

MLS# A4678422 · Listing courtesy of GENEROUS PROPERTY

524 SARABAY ROAD, OSPREY
Active

$419,000

524 SARABAY ROAD

OSPREY, FL 34229

3 bed
2 bath
1,760 sqft

MLS# A4676179 · Listing courtesy of SUN N SAND REAL ESTATE LLC

570 BLACKBURN POINT ROAD #43, OSPREY
Active

$115,000

570 BLACKBURN POINT ROAD #43

OSPREY, FL 34229

0 bed
0 bath
0 sqft

MLS# A4672823 · Listing courtesy of BRIGHT REALTY

570 BLACKBURN POINT ROAD #13, OSPREY
Active

$109,000

570 BLACKBURN POINT ROAD #13

OSPREY, FL 34229

0 bed
0 bath
0 sqft

MLS# A4674344 · Listing courtesy of BRIGHT REALTY

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

1811 HIGHLAND ROAD, OSPREY
Active

$409,900

1811 HIGHLAND ROAD

OSPREY, FL 34229

2 bed
2 bath
1,725 sqft

MLS# TB8443161 · Listing courtesy of REALTY OF RIVERVIEW LLC

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

348 TROPIC DRIVE, OSPREY
Active

$104,900

348 TROPIC DRIVE

OSPREY, FL 34229

2 bed
2 bath
864 sqft

MLS# A4668240 · Listing courtesy of FINE PROPERTIES

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

1801 HIGHLAND ROAD, OSPREY
Active Under Contract

$289,900

1801 HIGHLAND ROAD

OSPREY, FL 34229

2 bed
2 bath
1,165 sqft

MLS# N6140508 · Listing courtesy of RE/MAX ALLIANCE GROUP

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

570 BLACKBURN POINT ROAD #11, OSPREY
Active

$39,500

570 BLACKBURN POINT ROAD #11

OSPREY, FL 34229

0 bed
0 bath
0 sqft

MLS# A4658755 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

4428 CONCHFISH LANE, OSPREY
Active

$525,000

4428 CONCHFISH LANE

OSPREY, FL 34229

4 bed
2 bath
1,861 sqft

MLS# A4656074 · Listing courtesy of HORIZON REALTY INTERNATIONAL

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

13 BAYHEAD LANE, OSPREY
Active

$769,000

13 BAYHEAD LANE

OSPREY, FL 34229

3 bed
2 bath
2,310 sqft

MLS# A4645829 · Listing courtesy of GENEROUS PROPERTY

236 SAINT JAMES PARK, OSPREY
Active

$2,700,000

236 SAINT JAMES PARK

OSPREY, FL 34229

6 bed
7 bath
6,246 sqft

MLS# A4644125 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

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