Osprey Homes Under $500K

34 homes under $500K for sale in Osprey, median asking price $262,000, mostly $101,000 – $463,000. Homes with an asking price under $500,000. Osprey (ZIP 34229). Nokomis has its own page. As of Oct 9, 2026.

120 VILLA DRIVE #120, OSPREY
Active

$465,000

120 VILLA DRIVE #120

OSPREY, FL 34229

2 bed
2 bath
1,404 sqft

MLS# A4708477 · Listing courtesy of MANGROVE REALTY ASSOCIATES

145 EDGEWOOD DRIVE, OSPREY
Active

$175,000

145 EDGEWOOD DRIVE

OSPREY, FL 34229

2 bed
2 bath
960 sqft

MLS# A4707317 · Listing courtesy of GENEROUS PROPERTY

717 PINE RUN DR. #717, OSPREY
Active

$159,900

717 PINE RUN DR. #717

OSPREY, FL 34229

1 bed
1 bath
586 sqft

MLS# A4708286 · Listing courtesy of PAT WILLIAMS REALTY, LLC

7303 JESSIE HARBOR DRIVE #7303, OSPREY
Active

$449,000

7303 JESSIE HARBOR DRIVE #7303

OSPREY, FL 34229

3 bed
2 bath
1,883 sqft

MLS# A4706429 · Listing courtesy of COLDWELL BANKER REALTY

23 SIESTA CIRCLE, OSPREY
Active

$165,000

23 SIESTA CIRCLE

OSPREY, FL 34229

2 bed
2 bath
924 sqft

MLS# A4706691 · Listing courtesy of COLDWELL BANKER SARASOTA CENT.

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

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

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

1819 HIGHLAND ROAD, OSPREY
Active

$319,000

1819 HIGHLAND ROAD

OSPREY, FL 34229

2 bed
3 bath
1,240 sqft

MLS# A4703963 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

701 PINE RUN DRIVE #701, OSPREY
Pending

$151,000

701 PINE RUN DRIVE #701

OSPREY, FL 34229

1 bed
1 bath
586 sqft

MLS# A4700416 · Listing courtesy of PAT WILLIAMS REALTY, LLC

570 BLACKBURN POINT ROAD #36, OSPREY
Active

$99,500

570 BLACKBURN POINT ROAD #36

OSPREY, FL 34229

0 bed
0 bath
0 sqft

MLS# A4700865 · Listing courtesy of BRIGHT REALTY

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

2309 JESSIE HARBOR DRIVE #2402, OSPREY
Active

$480,000

2309 JESSIE HARBOR DRIVE #2402

OSPREY, FL 34229

3 bed
3 bath
2,006 sqft

MLS# A4698434 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

570 BLACKBURN POINT ROAD #23, OSPREY
Active

$89,000

570 BLACKBURN POINT ROAD #23

OSPREY, FL 34229

0 bed
0 bath
0 sqft

MLS# A4697977 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

7204 JESSIE HARBOR DRIVE #7204, OSPREY
Active

$395,000

7204 JESSIE HARBOR DRIVE #7204

OSPREY, FL 34229

2 bed
2 bath
1,255 sqft

MLS# A4697473 · Listing courtesy of GENEROUS PROPERTY

110 WOODLAND PLACE #110, OSPREY
Active Under Contract

$215,000

110 WOODLAND PLACE #110

OSPREY, FL 34229

2 bed
2 bath
1,325 sqft

MLS# A4696738 · Listing courtesy of COLDWELL BANKER REALTY

116 WOODLAND PLACE #116, OSPREY
Active

$249,900

116 WOODLAND PLACE #116

OSPREY, FL 34229

2 bed
2 bath
1,325 sqft

MLS# A4696616 · Listing courtesy of PAT WILLIAMS REALTY, LLC

4296 EXPEDITION WAY #104, OSPREY
Active

$289,000

4296 EXPEDITION WAY #104

OSPREY, FL 34229

2 bed
2 bath
1,135 sqft

MLS# A4694926 · Listing courtesy of EXP REALTY LLC

320 TROPIC DRIVE, OSPREY
Active

$185,000

320 TROPIC DRIVE

OSPREY, FL 34229

2 bed
2 bath
1,199 sqft

MLS# A4692490 · Listing courtesy of RE/MAX PALM

51 MACEWEN DRIVE #12, OSPREY
Active

$275,000

51 MACEWEN DRIVE #12

OSPREY, FL 34229

1 bed
1 bath
623 sqft

MLS# A4690540 · Listing courtesy of COLDWELL BANKER REALTY

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

51 MAC EWEN DRIVE #14, OSPREY
Active

$285,000

51 MAC EWEN DRIVE #14

OSPREY, FL 34229

1 bed
1 bath
595 sqft

MLS# A4690371 · Listing courtesy of COLDWELL BANKER REALTY

51 MACEWEN DRIVE #5, OSPREY
Active

$235,000

51 MACEWEN DRIVE #5

OSPREY, FL 34229

1 bed
1 bath
595 sqft

MLS# A4689838 · Listing courtesy of 342 REAL ESTATE

4226 FRONTIER LANE #103, OSPREY
Active Under Contract

$299,000

4226 FRONTIER LANE #103

OSPREY, FL 34229

2 bed
2 bath
1,135 sqft

MLS# A4687965 · Listing courtesy of COLDWELL BANKER REALTY

More in Osprey

Homes Under $500K nearby

Questions about Osprey Homes Under $500K

How many homes under $500K are for sale in Osprey?

34 homes under $500K 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 under $500K in Osprey?

The median asking price is $262,000; most are listed between $101,000 and $463,000. 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 under $500K?

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, 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