Luxury Homes for Sale in Osprey, FL

By Jon Brooks, Co-Founder, Momentum Realty · Updated September 16, 2026

The luxury market in Osprey starts at $1,030,000 — about 1.5× the city’s median asking price. This page is every active listing at that level, refreshed nightly from the MLS, with what has actually closed, where the inventory sits and how long it takes to sell. For the wider picture see luxury communities in Sarasota County.

20 luxury homes are for sale in Osprey, FL at $1,030,000 and up — median asking $1,735,000, the top listing at $9,750,000, $506 per square foot. 24 homes closed above $1,030,000 in the last 12 months at a median of $1,700,000. 20% of the luxury inventory is waterfront. Median days on market: 114.

Newest luxury listings in Osprey

$2,199,999 New

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

154 Lookout Point Drive, 34229

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, 34229

Listing courtesy of COLDWELL BANKER REALTY

$9,750,000 New

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

1216 N Casey Key Road, 34229

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, 34229

Southbay Yacht & Racquet Club

Listing courtesy of PAT WILLIAMS REALTY, LLC

$1,900,000 New

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

916 Macewen Drive, 34229

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, 34229

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, 34229

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, 34229

Listing courtesy of BEYOND REALTY LLC

$1,100,000

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

907 Eagle Isle Court, 34229

Listing courtesy of CENTURY 21 ROSEBAY

$1,770,000

3 bd · 2 ba · 2,411 sq ft · built 1991

206 Four Knot Lane, 34229

Southbay Yacht & Racquet Club

Listing courtesy of REALTY ONE GROUP MVP

$5,999,999

4 bd · 4.5 ba · 5,337 sq ft · built 2016

313 Lookout Point Drive, 34229

Southbay Yacht & Racquet Club

Listing courtesy of MICHAEL SAUNDERS & COMPANY

$1,250,000

3 bd · 3 ba · 2,594 sq ft · built 2004

409 N Point Road #601, 34229

Meridian At The Oaks Preserve

Listing courtesy of GENEROUS PROPERTY

$1,995,000

3 bd · 3 ba · 3,029 sq ft · built 2003

401 N Point Road #1001, 34229

Meridian At The Oaks Preserve

Listing courtesy of GENEROUS PROPERTY

$1,100,000

3 bd · 3 ba · 2,778 sq ft · built 2000

385 N Point Road #304, 34229

Meridian At The Oaks Preserve

Listing courtesy of GENEROUS PROPERTY

$6,475,000

5 bd · 5.5 ba · 4,096 sq ft · built 1969

121 N Casey Key Road, 34229

Casey Key

Listing courtesy of DOUGLAS ELLIMAN

$1,950,000

4 bd · 5.5 ba · 4,346 sq ft · built 2002

538 Dove Pointe Drive, 34229

Listing courtesy of GENEROUS PROPERTY

$2,700,000

6 bd · 6.5 ba · 6,246 sq ft · built 1986

236 Saint James Park, 34229

Oaks 2 Ph 2

Listing courtesy of MICHAEL SAUNDERS & COMPANY

$2,395,000

3 bd · 3.5 ba · 4,519 sq ft · built 1992

852 Macewen Drive, 34229

Oaks 2 Ph 2

Listing courtesy of GENEROUS PROPERTY

$1,595,000

3 bd · 3.5 ba · 4,241 sq ft · built 1991

909 Macewen Drive, 34229

Oaks 2 Ph 2

Listing courtesy of GENEROUS PROPERTY

The most expensive homes for sale in Osprey

Where the luxury inventory is

Luxury inventory by price

How to read this

Luxury is defined here as asking prices at or above $1,030,000. Counts, medians and closings come from active and closed MLS listings as of September 16, 2026; closings are the trailing 12 months. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 74 homes for sale in Osprey and what $1M buys across Sarasota County.