Homes for Sale in Osprey, FL
75 homes are for sale in Osprey, FL as of 2026-09-06, with 12 more under contract. The median list price is $675,000 ($305/sq ft), most homes list between $285K to $2M, and the median listing has been on the market 112 days. 13 homes came on the market this week and 47 sold in the last 12 months at a median of $550,000.
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.
Osprey homes for sale by price
Every active listing in Osprey grouped by price, with the newest listings in each band. The median is $675,000; the busiest band is $1M and up.
Under $200K: 3 homes
- $165,900 · 1 bd / 1 ba / 586 sq ft · 701 PINE RUN DRIVE #701
- $185,000 · 2 bd / 2 ba / 1,199 sq ft · 320 TROPIC DRIVE
- $109,900 · 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
- $235,000 · 1 bd / 1 ba / 595 sq ft · 51 MACEWEN DRIVE #5
- $215,000 · 2 bd / 2 ba / 1,325 sq ft · 110 WOODLAND PLACE #110
- $249,900 · 2 bd / 2 ba / 1,325 sq ft · 116 WOODLAND PLACE #116
$300K – $400K: 7 homes
- $319,000 · 2 bd / 2.5 ba / 1,240 sq ft · 1819 HIGHLAND ROAD
- $305,950 · 2 bd / 2 ba / 1,593 sq ft · 108 VILLA DRIVE #108
- $395,000 · 2 bd / 2 ba / 1,255 sq ft · 7204 JESSIE HARBOR DRIVE #7204
- $317,000 · 3 bd / 2 ba / 1,430 sq ft · 4213 EXPEDITION WAY #107
$400K – $500K: 6 homes
- $425,000 · 2 bd / 2 ba / 1,574 sq ft · 780 SARABAY ROAD #16
- $497,000 · 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
- $409,900 · 2 bd / 2 ba / 1,725 sq ft · 1811 HIGHLAND ROAD
$500K – $750K: 21 homes
- $529,000 · 4 bd / 2 ba / 2,203 sq ft · 583 PINE RANCH EAST ROAD
- $585,000 · 3 bd / 2 ba / 1,705 sq ft · 2046 CORDES STREET
- $599,000 · 2 bd / 2 ba / 2,143 sq ft · 5100 JESSIE HARBOR DRIVE #404
- $540,000 · 3 bd / 2.5 ba / 2,040 sq ft · 1140 BEACHCOMBER COURT #11
$750K – $1M: 8 homes
- $850,000 · 4 bd / 3 ba / 2,468 sq ft · 144 PARK TRACE BOULEVARD
- $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
- $760,000 · 3 bd / 2 ba / 2,474 sq ft · 1495 LANDVIEW LANE
$1M and up: 22 homes
- $1.15M · 3 bd / 1.5 ba / 2,084 sq ft · 210 PATTERSON AVENUE
- $2.20M · 4 bd / 3.5 ba / 4,578 sq ft · 154 LOOKOUT POINT DRIVE
- $1.50M · 3 bd / 2.5 ba / 2,591 sq ft · 226 SAINT JAMES PARK
- $9.75M · 5 bd / 7 ba / 8,050 sq ft · 1216 N CASEY KEY ROAD
What is for sale in Osprey: property types
- Single-family homes: 34
- Condos: 32
- Townhouses: 5
- Manufactured homes: 2
- Villas: 2
Another 8 listings in Osprey are land, commercial or other non-residential property and are not counted above.
Browse by type: Condos for sale in Osprey (32).
The Osprey housing market right now
Over the last 12 months 47 homes sold in Osprey at a median of $550,000 (+0.5% year over year), $271 per square foot. Sellers received 92% of list price and homes took a median 39 days to go under contract. With 75 homes for sale against that sales pace, months of supply is 19.1, a buyer’s market by the six-month rule. Cash buyers accounted for 46% of sales. New construction was 2% of sales.
Osprey home prices by year
Median sold price, closed sales, days on market and sale-to-list ratio by year, from Momentum’s MLS record.
| Year | Median sold price | Homes sold | Days on market | Sale-to-list |
|---|---|---|---|---|
| 2019 | $386,996 | 31 | 140 | 92% |
| 2021 | $644,687 | 16 | 5 | 99% |
| 2022 | $723,334 | 135 | 6 | 100% |
| 2023 | $793,264 | 34 | 19 | 93% |
| 2024 | $847,616 | 86 | 30 | 94% |
| 2025 | $844,961 | 85 | 53 | 93% |
| 2026 | $749,936 | 101 | 39 | 92% |
What a home in Osprey costs to own
Take the median $675,000 listing with 20% down at today’s 6.71% 30-year rate: principal and interest run about $3,488/month. Sarasota County’s typical millage of 13.48 puts property tax near $8,424/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 $4,367/month plus any HOA or CDD assessment.
Explore Osprey
- All homes for sale in Sarasota County, FL
- Osprey market intelligence: prices, supply and trends
- Sarasota County property tax guide
- Search every Osprey community
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Common questions
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Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Osprey as of 2026-09-06 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.