Homes for Sale in Osprey, FL 34229

Every active MLS listing in Osprey’s 34229 ZIP code, refreshed nightly, with the price bands, the property mix and the communities that have the most homes for sale. For the whole city see homes for sale in Osprey, FL (74 listings); for the ZIP’s values, taxes and growth see the 34229 housing scorecard.

71 homes are for sale in ZIP 34229 (Osprey, FL) right now, from $165,900 to $1,950,000 for the middle 80%, at a median asking price of $629,000 and $315 per square foot. The typical listing is 2,188 sq ft, built 2002; 15 came on the market in the last 7 days and 1% are new construction.

Newest homes for sale in 34229

$2,199,999 New

4 bd · 3.5 ba · 4,578 sq ft · built 1979

154 Lookout Point Drive

Southbay Yacht & Racquet Club

Listing courtesy of FLAT FEE MLS REALTY

$1,700,000 New

3 bd · 3 ba · 3,118 sq ft · built 2016

141 Sugar Mill Drive

Listing courtesy of COLDWELL BANKER REALTY

$529,000 New

4 bd · 2 ba · 2,203 sq ft · built 1996

583 Pine Ranch East Road

Listing courtesy of GALLERY PROPERTIES INTERNATIONAL

$299,990 New

2 bd · 2 ba · 1,135 sq ft · built 2017

4296 Expedition Way #104

Listing courtesy of EXP REALTY LLC

$99,500 New

570 Blackburn Point Road #36

Listing courtesy of BRIGHT REALTY

$540,000 New

3 bd · 2.5 ba · 2,040 sq ft · built 2005

1140 Beachcomber Court #11

Listing courtesy of LISTWITHFREEDOM.COM

$9,750,000 New

5 bd · 7 ba · 8,050 sq ft · built 1999

1216 N Casey Key Road

Casey Key

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

$1,399,000 New

4 bd · 4 ba · 3,255 sq ft · built 2014

1417 Landview Lane

Southbay Yacht & Racquet Club

Listing courtesy of PAT WILLIAMS REALTY, LLC

$319,000 New

2 bd · 2.5 ba · 1,240 sq ft · built 1998

1819 Highland Road

Listing courtesy of MICHAEL SAUNDERS & COMPANY

$775,000 New

3 bd · 2.5 ba · 1,950 sq ft · built 2019

260 Hidden Bay Drive #402

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

$749,900 New

3 bd · 2 ba · 2,174 sq ft · built 2003

1328 Thornapple Drive

Listing courtesy of RIVER HILLS PROPERTIES, LLC B

$1,900,000 New

5 bd · 7.5 ba · 5,986 sq ft · built 1991

916 Macewen Drive

Oaks 2 Ph 2

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

$1,495,000 New

3 bd · 2.5 ba · 2,591 sq ft · built 1988

226 Saint James Park

Oaks 2 Ph 2

Listing courtesy of KELLER WILLIAMS ON THE WATER S

$1,150,000 New

3 bd · 1.5 ba · 2,084 sq ft · built 1950

210 Patterson Avenue

Listing courtesy of REALTY ONE GROUP MVP

$1,100,000

5 bd · 3.5 ba · 3,354 sq ft · built 1995

296 Pine Ranch Trail

Listing courtesy of BEYOND REALTY LLC

$1,100,000

4 bd · 3 ba · 3,984 sq ft · built 2003

907 Eagle Isle Court

Listing courtesy of CENTURY 21 ROSEBAY

$585,000

3 bd · 2 ba · 1,705 sq ft · built 1998

2046 Cordes Street

Listing courtesy of MICHAEL SAUNDERS & COMPANY

$985,000

3 bd · 3 ba · 2,203 sq ft · built 2004

409 N Point Road #803

Meridian At The Oaks Preserve

Listing courtesy of GENEROUS PROPERTY

$599,000

2 bd · 2 ba · 2,143 sq ft · built 2004

5100 Jessie Harbor Drive #404

Listing courtesy of MICHAEL SAUNDERS & COMPANY

$695,000

3 bd · 3 ba · 2,837 sq ft · built 1992

264 Woods Point Road #264

Listing courtesy of MICHAEL SAUNDERS & COMPANY

$235,000

1 bd · 1 ba · 595 sq ft · built 1990

51 Macewen Drive #5

Listing courtesy of 342 REAL ESTATE

$299,950

2 bd · 2 ba · 1,593 sq ft · built 1976

108 Villa Drive #108

Listing courtesy of LOKATION

$395,000

2 bd · 2 ba · 1,255 sq ft · built 1985

7204 Jessie Harbor Drive #7204

Listing courtesy of GENEROUS PROPERTY

$165,900

1 bd · 1 ba · 586 sq ft · built 1973

701 Pine Run Drive #701

Listing courtesy of PAT WILLIAMS REALTY, LLC

$317,000

3 bd · 2 ba · 1,430 sq ft · built 2016

4213 Expedition Way #107

Listing courtesy of DALTON WADE INC

$89,000

· built 2006

570 Blackburn Point Road #23

Listing courtesy of MICHAEL SAUNDERS & COMPANY

$399,000

2 bd · 2 ba · 1,346 sq ft · built 1963

329 Bay Vista Avenue

Bay Acres

Listing courtesy of THE SHORELINE FL REALTY LLC

$425,000

2 bd · 2 ba · 1,574 sq ft · built 1981

780 Sarabay Road #16

Listing courtesy of RMS ELITE PROPERTIES

$480,000

3 bd · 2.5 ba · 2,006 sq ft · built 2006

2309 Jessie Harbor Drive #2402

Listing courtesy of MICHAEL SAUNDERS & COMPANY

$760,000

3 bd · 2 ba · 2,474 sq ft · built 1988

1495 Landview Lane

Southbay Yacht & Racquet Club

Listing courtesy of PAT WILLIAMS REALTY, LLC

Homes for sale in 34229 by price

Communities in 34229 with the most homes for sale

• Meridian At The Oaks Preserve · 12 for sale · median $622,000
• Southbay Yacht & Racquet Club · 5 for sale · median $1,770,000
• Oaks 2 Ph 2 · 5 for sale · median $1,900,000
• Bay Acres · 2 for sale · median $409,000
• Casey Key · 2 for sale · median $8,112,500
• Park Trace Estates · 1 for sale · median $824,900

How to read this

Counts and medians are from active MLS listings with a 34229 mailing ZIP as of September 16, 2026; property mix Single-family 41%, Condo 41%, Townhouse 6%. Prices are asking prices. Listings are shown with the courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also homes for sale in Sarasota County. More: Osprey condos, luxury homes in Osprey, new listings this week in Osprey.