Homes for Sale in Osprey, FL

By Jon Brooks, Co-Founder, Momentum Realty · Updated September 25, 2026

73 homes are for sale in Osprey, FL as of 2026-09-25, with 14 more under contract. The median list price is $700,000 ($307/sq ft), most homes list between $290K to $2M, and the median listing has been on the market 92 days. That is 34 houses, 31 condos and 4 townhouses. 15 homes came on the market this week.

Newest homes for sale in Osprey

The most recently listed homes in Osprey, newest first, with photos. Each card opens the full listing with every photo, the community’s sales history and a tour request. Homes marked New listed in the last seven days.

$1.29M New

3 bd · 2 ba · 2,850 sq ft · built 1992

17 BAYHEAD LANE, 34229

Osprey

Listing courtesy of COLDWELL BANKER REALTY

$750,000 New

3 bd · 3 ba · 2,594 sq ft · built 2000

385 N POINT ROAD #301, 34229

Meridian at The Oaks Preserve

Listing courtesy of COLDWELL BANKER REALTY

$700,000 New

3 bd · 3 ba · 2,680 sq ft · built 2007

3621 NORTH POINT ROAD #403, 34229

Osprey

Listing courtesy of COLDWELL BANKER REALTY

$669,900 New

4 bd · 3 ba · 2,683 sq ft · built 2001

130 WILLOW BEND WAY, 34229

Osprey

Listing courtesy of RE/MAX ALLIANCE GROUP

$655,000 New

3 bd · 2.5 ba · 2,792 sq ft · built 2002

700 SHADOW BAY WAY, 34229

Rivendell

Listing courtesy of KARA MONEY LLC

$529,000 New

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

583 PINE RANCH EAST ROAD, 34229

Osprey

Listing courtesy of GALLERY PROPERTIES INTERNATIONAL

$299,990 New

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

4296 EXPEDITION WAY #104, 34229

Osprey

Listing courtesy of EXP REALTY LLC

$165,000 New

2 bd · 2 ba · 924 sq ft · built 2001

23 SIESTA CIRCLE, 34229

Osprey

Listing courtesy of COLDWELL BANKER SARASOTA CENT.

$1.70M New

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

141 SUGAR MILL DRIVE, 34229

Osprey

Listing courtesy of COLDWELL BANKER REALTY

$540,000 New

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

1140 BEACHCOMBER COURT #11, 34229

Osprey

Listing courtesy of LISTWITHFREEDOM.COM

$9.75M 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

$319,000 New

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

1819 HIGHLAND ROAD, 34229

Osprey

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, 34229

Osprey

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

$255,000 New

2 bd · 2 ba · 1,223 sq ft · built 1979

109 WOODLAND PLACE, 34229

Osprey

Listing courtesy of PREFERRED SHORE LLC

$1.15M New

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

210 PATTERSON AVENUE, 34229

Osprey

Listing courtesy of REALTY ONE GROUP MVP

$1.10M

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

296 PINE RANCH TRAIL, 34229

Osprey

Listing courtesy of BEYOND REALTY LLC

$1.10M

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

907 EAGLE ISLE COURT, 34229

Osprey

Listing courtesy of CENTURY 21 ROSEBAY

$649,000

3 bd · 2 ba · 2,084 sq ft · built 2003

586 OAK BAY DRIVE, 34229

Osprey

Listing courtesy of WHITE SANDS REALTY GROUP FL

$1.40M

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

$985,000

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

409 N POINT ROAD #803, 34229

Meridian at The Oaks Preserve

Listing courtesy of GENEROUS PROPERTY

$749,900

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

1328 THORNAPPLE DRIVE, 34229

Osprey

Listing courtesy of RIVER HILLS PROPERTIES, LLC B

$585,000

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

2046 CORDES STREET, 34229

Osprey

Listing courtesy of MICHAEL SAUNDERS & COMPANY

$1.50M

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

226 SAINT JAMES PARK, 34229

The Oaks

Listing courtesy of KELLER WILLIAMS ON THE WATER S

$235,000

1 bd · 1 ba · 595 sq ft · built 1990

51 MACEWEN DRIVE #5, 34229

Osprey

Listing courtesy of 342 REAL ESTATE

Osprey homes for sale by price

Every active listing in Osprey grouped by price, with the newest listings in each band. The median is $700,000; the busiest band is $500K – $750K.

Under $200K: 3 homes

• $165,000 · 2 bd / 2 ba / 924 sq ft · 23 SIESTA CIRCLE
• $185,000 · 2 bd / 2 ba / 1,199 sq ft · 320 TROPIC DRIVE
• $104,900 · 2 bd / 2 ba / 864 sq ft · 348 TROPIC DRIVE

$200K – $300K: 8 homes

• $299,990 · 2 bd / 2 ba / 1,135 sq ft · 4296 EXPEDITION WAY #104
• $255,000 · 2 bd / 2 ba / 1,223 sq ft · 109 WOODLAND PLACE
• $235,000 · 1 bd / 1 ba / 595 sq ft · 51 MACEWEN DRIVE #5
• $299,950 · 2 bd / 2 ba / 1,593 sq ft · 108 VILLA DRIVE #108

$300K – $400K: 5 homes

• $319,000 · 2 bd / 2.5 ba / 1,240 sq ft · 1819 HIGHLAND ROAD
• $395,000 · 2 bd / 2 ba / 1,255 sq ft · 7204 JESSIE HARBOR DRIVE #7204
• $399,000 · 2 bd / 2 ba / 1,346 sq ft · 329 BAY VISTA AVENUE
• $317,000 · 3 bd / 2 ba / 1,430 sq ft · 4213 EXPEDITION WAY #107

$400K – $500K: 4 homes

• $480,000 · 3 bd / 2.5 ba / 2,006 sq ft · 2309 JESSIE HARBOR DRIVE #2402
• $419,000 · 3 bd / 2 ba / 1,760 sq ft · 524 SARABAY ROAD (Bay Acres)
• $409,900 · 2 bd / 2 ba / 1,725 sq ft · 1811 HIGHLAND ROAD
• $459,900 · 3 bd / 3 ba / 2,594 sq ft · 401 N POINT ROAD #301 (Meridian at The Oaks Preserve)

$500K – $750K: 22 homes

• $529,000 · 4 bd / 2 ba / 2,203 sq ft · 583 PINE RANCH EAST ROAD
• $655,000 · 3 bd / 2.5 ba / 2,792 sq ft · 700 SHADOW BAY WAY (Rivendell)
• $669,900 · 4 bd / 3 ba / 2,683 sq ft · 130 WILLOW BEND WAY
• $700,000 · 3 bd / 3 ba / 2,680 sq ft · 3621 NORTH POINT ROAD #403

$750K – $1M: 9 homes

• $750,000 · 3 bd / 3 ba / 2,594 sq ft · 385 N POINT ROAD #301 (Meridian at The Oaks Preserve)
• $775,000 · 3 bd / 2.5 ba / 1,950 sq ft · 260 HIDDEN BAY DRIVE #402
• $985,000 · 3 bd / 3 ba / 2,203 sq ft · 409 N POINT ROAD #803 (Meridian at The Oaks Preserve)
• $795,000 · 3 bd / 3 ba / 2,778 sq ft · 401 N POINT ROAD #504

$1M and up: 22 homes

• $1.29M · 3 bd / 2 ba / 2,850 sq ft · 17 BAYHEAD LANE
• $1.70M · 3 bd / 3 ba / 3,118 sq ft · 141 SUGAR MILL DRIVE
• $9.75M · 5 bd / 7 ba / 8,050 sq ft · 1216 N CASEY KEY ROAD (Casey Key)
• $1.15M · 3 bd / 1.5 ba / 2,084 sq ft · 210 PATTERSON AVENUE

Every home for sale in Osprey right now (73)

All 73 active Osprey listings with a detail page, newest first, refreshed twice a day from the MLS.

• $1.29M · 3 bd / 2 ba / 2,850 sq ft · 17 BAYHEAD LANE
• $750,000 · 3 bd / 3 ba / 2,594 sq ft · 385 N POINT ROAD #301 (Meridian at The Oaks Preserve)
• $700,000 · 3 bd / 3 ba / 2,680 sq ft · 3621 NORTH POINT ROAD #403
• $669,900 · 4 bd / 3 ba / 2,683 sq ft · 130 WILLOW BEND WAY
• $655,000 · 3 bd / 2.5 ba / 2,792 sq ft · 700 SHADOW BAY WAY (Rivendell)
• $529,000 · 4 bd / 2 ba / 2,203 sq ft · 583 PINE RANCH EAST ROAD
• $299,990 · 2 bd / 2 ba / 1,135 sq ft · 4296 EXPEDITION WAY #104
• $165,000 · 2 bd / 2 ba / 924 sq ft · 23 SIESTA CIRCLE
• $1.70M · 3 bd / 3 ba / 3,118 sq ft · 141 SUGAR MILL DRIVE
• $540,000 · 3 bd / 2.5 ba / 2,040 sq ft · 1140 BEACHCOMBER COURT #11
• $9.75M · 5 bd / 7 ba / 8,050 sq ft · 1216 N CASEY KEY ROAD (Casey Key)
• $319,000 · 2 bd / 2.5 ba / 1,240 sq ft · 1819 HIGHLAND ROAD
• $775,000 · 3 bd / 2.5 ba / 1,950 sq ft · 260 HIDDEN BAY DRIVE #402
• $255,000 · 2 bd / 2 ba / 1,223 sq ft · 109 WOODLAND PLACE
• $1.15M · 3 bd / 1.5 ba / 2,084 sq ft · 210 PATTERSON AVENUE
• $1.10M · 5 bd / 3.5 ba / 3,354 sq ft · 296 PINE RANCH TRAIL
• $1.10M · 4 bd / 3 ba / 3,984 sq ft · 907 EAGLE ISLE COURT
• $649,000 · 3 bd / 2 ba / 2,084 sq ft · 586 OAK BAY DRIVE
• $1.40M · 4 bd / 4 ba / 3,255 sq ft · 1417 LANDVIEW LANE (Southbay Yacht & Racquet Club)
• $985,000 · 3 bd / 3 ba / 2,203 sq ft · 409 N POINT ROAD #803 (Meridian at The Oaks Preserve)
• $749,900 · 3 bd / 2 ba / 2,174 sq ft · 1328 THORNAPPLE DRIVE
• $585,000 · 3 bd / 2 ba / 1,705 sq ft · 2046 CORDES STREET
• $1.50M · 3 bd / 2.5 ba / 2,591 sq ft · 226 SAINT JAMES PARK (The Oaks)
• $235,000 · 1 bd / 1 ba / 595 sq ft · 51 MACEWEN DRIVE #5
• $299,950 · 2 bd / 2 ba / 1,593 sq ft · 108 VILLA DRIVE #108
• $2.10M · 4 bd / 3.5 ba / 4,578 sq ft · 154 LOOKOUT POINT DRIVE (Southbay Yacht & Racquet Club)
• $695,000 · 3 bd / 3 ba / 2,837 sq ft · 264 WOODS POINT ROAD #264
• $599,000 · 2 bd / 2 ba / 2,143 sq ft · 5100 JESSIE HARBOR DRIVE #404
• $395,000 · 2 bd / 2 ba / 1,255 sq ft · 7204 JESSIE HARBOR DRIVE #7204
• $399,000 · 2 bd / 2 ba / 1,346 sq ft · 329 BAY VISTA AVENUE
• $317,000 · 3 bd / 2 ba / 1,430 sq ft · 4213 EXPEDITION WAY #107
• $480,000 · 3 bd / 2.5 ba / 2,006 sq ft · 2309 JESSIE HARBOR DRIVE #2402
• $795,000 · 3 bd / 3 ba / 2,778 sq ft · 401 N POINT ROAD #504
• $215,000 · 2 bd / 2 ba / 1,325 sq ft · 110 WOODLAND PLACE #110
• $185,000 · 2 bd / 2 ba / 1,199 sq ft · 320 TROPIC DRIVE
• $760,000 · 3 bd / 2 ba / 2,474 sq ft · 1495 LANDVIEW LANE
• $1.69M · 3 bd / 2 ba / 2,411 sq ft · 206 FOUR KNOT LANE (Southbay Yacht & Racquet Club)
• $249,900 · 2 bd / 2 ba / 1,325 sq ft · 116 WOODLAND PLACE #116
• $719,000 · 3 bd / 2 ba / 1,937 sq ft · 280 HIDDEN BAY DRIVE #302
• $700,000 · 4 bd / 3.5 ba / 2,950 sq ft · 759 FORDINGBRIDGE WAY
• $699,000 · 2 bd / 2 ba / 2,143 sq ft · 5100 JESSIE HARBOR DRIVE #304
• $318,000 · 3 bd / 2 ba / 1,528 sq ft · 4304 EXPEDITION WAY WAY #105
• $798,000 · 3 bd / 3.5 ba / 3,771 sq ft · 6100 JESSIE HARBOR DRIVE #202
• $999,900 · 3 bd / 3 ba / 2,187 sq ft · 14021 BELLAGIO WAY #404
• $749,000 · 3 bd / 3 ba / 2,583 sq ft · 678 FAITH AVENUE
• $560,000 · 3 bd / 3 ba / 2,594 sq ft · 409 NORTH POINT ROAD #401 (Meridian at The Oaks Preserve)
• $510,000 · 3 bd / 2 ba / 2,004 sq ft · 4429 CONCHFISH LANE
• $6.00M · 4 bd / 4.5 ba / 5,337 sq ft · 313 LOOKOUT POINT DRIVE (Southbay Yacht & Racquet Club)
• $2.85M · 3 bd / 3.5 ba / 2,665 sq ft · 14401 MASTHEAD DRIVE
• $1.17M · 3 bd / 2.5 ba / 2,830 sq ft · 1527 BUOY LANE (Southbay Yacht & Racquet Club)
• $700,000 · 3 bd / 2 ba / 1,799 sq ft · 14041 BELLAGIO WAY #214
• $299,000 · 2 bd / 2 ba / 1,135 sq ft · 4226 FRONTIER LANE #103
• $419,000 · 3 bd / 2 ba / 1,760 sq ft · 524 SARABAY ROAD (Bay Acres)
• $525,000 · 3 bd / 3 ba / 2,680 sq ft · 3621 N POINT ROAD #301 (Meridian at The Oaks Preserve)
• $1.25M · 3 bd / 3 ba / 2,594 sq ft · 409 N POINT ROAD #601 (Meridian at The Oaks Preserve)
• $2.00M · 3 bd / 3 ba / 3,029 sq ft · 401 N POINT ROAD #1001 (Meridian at The Oaks Preserve)
• $1.75M · 3 bd / 2 ba / 1,977 sq ft · 18 N CASEY KEY ROAD (Casey Key)
• $1.10M · 3 bd / 3 ba / 2,778 sq ft · 385 N POINT ROAD #304 (Meridian at The Oaks Preserve)
• $700,000 · 2 bd / 2 ba / 1,932 sq ft · 242 HIDDEN BAY DRIVE #602
• $409,900 · 2 bd / 2 ba / 1,725 sq ft · 1811 HIGHLAND ROAD
• $104,900 · 2 bd / 2 ba / 864 sq ft · 348 TROPIC DRIVE
• $1.95M · 4 bd / 5.5 ba / 4,346 sq ft · 538 DOVE POINTE DRIVE
• $815,000 · 3 bd / 2 ba / 2,188 sq ft · 599 PINE RANCH EAST ROAD
• $6.47M · 5 bd / 5.5 ba / 4,096 sq ft · 121 N CASEY KEY ROAD (Casey Key)
• $289,900 · 2 bd / 2 ba / 1,165 sq ft · 1801 HIGHLAND ROAD
• $789,000 · 3 bd / 2 ba / 2,246 sq ft · 21 BAYHEAD LANE
• $2.70M · 6 bd / 6.5 ba / 6,246 sq ft · 236 SAINT JAMES PARK (The Oaks)
• $2.40M · 3 bd / 3.5 ba / 4,519 sq ft · 852 MACEWEN DRIVE (The Oaks)
• $649,000 · 3 bd / 2 ba / 2,058 sq ft · 110 PINE AVENUE
• $615,000 · 3 bd / 3 ba / 2,055 sq ft · 385 N POINT ROAD #402 (Meridian at The Oaks Preserve)
• $459,900 · 3 bd / 3 ba / 2,594 sq ft · 401 N POINT ROAD #301 (Meridian at The Oaks Preserve)
• $1.59M · 3 bd / 3.5 ba / 4,241 sq ft · 909 MACEWEN DRIVE (The Oaks)
• $599,000 · 3 bd / 3 ba / 2,055 sq ft · 409 N POINT ROAD #502 (Meridian at The Oaks Preserve)

Homes for sale in Osprey by ZIP code

Where the inventory is: active listings and the median asking price by ZIP. ZIPs link to their housing scorecard.

Osprey communities with the most homes for sale

The Osprey neighborhoods and subdivisions with active listings, the median asking price in each, and what homes there actually sold for over the last 12 months. Community names open the community guide with live inventory, sales history, HOA and schools.

What is for sale in Osprey: property types

• Single-family houses: 34
• Condos: 31
• Townhouses: 4
• Manufactured homes: 3
• Villas: 1

Another 6 listings in Osprey are land, commercial or other non-residential property and are not counted above.

Browse by type: Condos for sale in Osprey (31).

What a home in Osprey costs to own

Take the median $700,000 listing with 20% down at today’s 6.95% 30-year rate: principal and interest run about $3,707/month. Sarasota County’s typical millage of 13.48 puts property tax near $8,761/year after the $50,000 homestead exemption — and that is the reset bill a buyer pays, not the seller’s capped one. Citizens’ average premium in Sarasota County is about $2,126/year; newer roofs and inland addresses usually quote below it. All in, plan on roughly $4,614/month plus any HOA or CDD assessment.

Explore Osprey

• All homes for sale in Sarasota County, FL
• What is my house worth in Osprey? Home values, $/sq ft and days to contract
• 4-bedroom homes for sale in Osprey
• Homes under $300K in Osprey
• Homes from $300K to $500K in Osprey
• Osprey pool homes for sale
• Osprey waterfront homes for sale
• Osprey golf course homes for sale
• Gated communities in Osprey
• Luxury homes for sale in Osprey
• New listings this week in Osprey
• What $500K buys in Sarasota County
• Osprey market intelligence: prices, supply and trends
• Moving to Osprey: the data guide
• Sarasota County property tax guide
• Sarasota County down payment assistance limits
• First-time home buyer guide for Florida
• Search every Osprey community
• Best places to live in Florida: every city ranked by the numbers
• All Florida cities and counties

Homes for sale near Osprey

• Homes for sale in Sarasota, FL — 2397 listings
• Homes for sale in North Port, FL — 917 listings
• Homes for sale in Venice, FL — 889 listings
• Homes for sale in Nokomis, FL — 254 listings
• Homes for sale in Longboat Key, FL — 228 listings
• Homes for sale in North Venice, FL — 25 listings

Recently off market in Osprey

Homes in Osprey that left the market most recently, with their last list price and a public-record page for each address. Off-market pages keep the community, tax and sales-history context after a listing closes or expires.

• 570 Blackburn Point Road #22 · last listed $145,000 · off market Sep 25, 2026
• 212 Washington Avenue · last listed $420,000 · off market Sep 24, 2026
• 1361 New Forest Lane · last listed $525,000 · off market Sep 23, 2026
• 1211 Lost Creek Court · last listed $829,000 · off market Sep 23, 2026
• 89 Navigation Circle · last listed $320,000 · off market Sep 22, 2026
• 780 Sarabay Road #16 · last listed $425,000 · off market Sep 22, 2026
• 4271 Expedition Way #103 · last listed $260,000 · off market Sep 22, 2026
• 347 Bayshore Drive · last listed $675,000 · off market Sep 19, 2026
• 480 Blackburn Point Road #6 · last listed $269,000 · off market Sep 17, 2026
• 700 Faith Avenue · last listed $1,200,000 · off market Sep 16, 2026
• 184 Explorer Drive · last listed $284,900 · off market Sep 16, 2026
• 742 Harms Drive · last listed $499,900 · off market Sep 15, 2026

Common questions

Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Osprey as of 2026-09-25 and refresh as homes list and sell. Listings courtesy of Stellar MLS as distributed by MLS GRID. The data relating to real estate for sale on this page comes in part from the Internet Data Exchange (IDX) program of the MLS(s) named above; listings held by brokerages other than Momentum Realty are marked with the listing brokerage’s name. Information is deemed reliable but not guaranteed. Estimates are not guarantees. Equal Housing Opportunity.