Homes for Sale in Osprey, FL
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100 homes are for sale in Osprey, FL as of 2026-10-15, with 15 more under contract. The median list price is $734,450 ($348/sq ft), most homes list between $285K to $2.40M, and the median listing has been on the market 79 days. That is 53 houses, 37 condos and 5 townhouses. 21 homes came on the market this week.
| Location | Sarasota County, FL |
|---|---|
| ZIP codes with their own page | 1 |
| For sale right now | 100 active, 15 under contract |
| Asking prices | $734,450 median · $348 per sq ft · most homes $285K–$2.40M |
| Median days on market (active listings) | 79 |
| Property types for sale | 53 houses, 37 condos, 5 townhouses |
| New listings this week | 21 |
Listing counts and prices as of 2026-10-15; MLS data, refreshed nightly. Market figures describe homes, not residents. Cite as: Momentum Realty, “Osprey, FL key facts,” movewithmomentum.com/homes-for-sale/osprey-fl/, data as of 2026-10-15.
100
Homes for sale
$734,450
Median list price
$285K to $2.40M
Typical range
79
Median days on market
21
New this week
15
Under contract
$5,014
Est. monthly cost at median
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 $734,450; the busiest band is $1M and up.
Under $200K: 5 homes
- $165,000 · 2 bd / 2 ba / 924 sq ft · 23 SIESTA CIRCLE
- $175,000 · 2 bd / 2 ba / 960 sq ft · 145 EDGEWOOD DRIVE
- $159,900 · 1 bd / 1 ba / 586 sq ft · 717 PINE RUN DR. #717
- $185,000 · 2 bd / 2 ba / 1,199 sq ft · 320 TROPIC DRIVE
$200K – $300K: 9 homes
- $244,900 · 2 bd / 2 ba / 1,223 sq ft · 109 WOODLAND PLACE
- $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: 2 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
$400K – $500K: 9 homes
- $465,000 · 2 bd / 2 ba / 1,404 sq ft · 120 VILLA DRIVE #120
- $449,000 · 3 bd / 2 ba / 1,883 sq ft · 7303 JESSIE HARBOR DRIVE #7303
- $499,999 · 3 bd / 3 ba / 2,422 sq ft · 453 S SHORE DRIVE
- $425,000 · 2 bd / 2 ba / 1,574 sq ft · 780 SARABAY ROAD #16
$500K – $750K: 26 homes
- $540,000 · 3 bd / 2 ba / 2,248 sq ft · 1346 THORNAPPLE DRIVE
- $629,400 · 3 bd / 3 ba / 3,147 sq ft · 3603 N POINT ROAD #202 (Meridian at The Oaks Preserve)
- $655,000 · 3 bd / 2.5 ba / 2,792 sq ft · 700 SHADOW BAY WAY (Rivendell)
- $679,000 · 2 bd / 2.5 ba / 1,890 sq ft · 33 BISHOPS COURT ROAD #118
$750K – $1M: 12 homes
- $799,000 · 3 bd / 2.5 ba / 2,678 sq ft · 1104 MALLARD MARSH DRIVE
- $985,000 · 3 bd / 3 ba / 2,203 sq ft · 409 N POINT ROAD #803 (Meridian at The Oaks Preserve)
- $950,000 · 3 bd / 1.5 ba / 2,084 sq ft · 210 PATTERSON AVENUE
- $775,000 · 3 bd / 2.5 ba / 1,950 sq ft · 260 HIDDEN BAY DRIVE #402
$1M and up: 37 homes
- $1.40M · 3 bd / 3 ba / 2,695 sq ft · 256 SUGAR MILL
- $1.02M · 3 bd / 3 ba / 2,778 sq ft · 401 N POINT ROAD #404 (Meridian at The Oaks Preserve)
- $1.05M · 3 bd / 2.5 ba / 2,134 sq ft · 102 WINDWARD DRIVE (Southbay Yacht & Racquet Club)
- $1.05M · 4 bd / 3 ba / 2,775 sq ft · 366 S CREEK COURT
Every home for sale in Osprey right now (100)
All 100 active Osprey listings with a detail page, newest first, refreshed twice a day from the MLS.
- $1.40M · 3 bd / 3 ba / 2,695 sq ft · 256 SUGAR MILL
- $3.70M · 4 bd / 4 ba / 4,314 sq ft · 650 OAKS CREEK COURT (The Oaks)
- $1.20M · 3 bd / 3 ba / 2,203 sq ft · 401 N POINT ROAD #703 (Meridian at The Oaks Preserve)
- $1.05M · 4 bd / 3 ba / 2,775 sq ft · 366 S CREEK COURT
- $1.05M · 3 bd / 2.5 ba / 2,134 sq ft · 102 WINDWARD DRIVE (Southbay Yacht & Racquet Club)
- $1.02M · 3 bd / 3 ba / 2,778 sq ft · 401 N POINT ROAD #404 (Meridian at The Oaks Preserve)
- $695,000 · 3 bd / 3 ba / 2,594 sq ft · 385 N POINT ROAD #401 (Meridian at The Oaks Preserve)
- $679,000 · 2 bd / 2.5 ba / 1,890 sq ft · 33 BISHOPS COURT ROAD #118
- $655,000 · 3 bd / 2.5 ba / 2,792 sq ft · 700 SHADOW BAY WAY (Rivendell)
- $629,400 · 3 bd / 3 ba / 3,147 sq ft · 3603 N POINT ROAD #202 (Meridian at The Oaks Preserve)
- $540,000 · 3 bd / 2 ba / 2,248 sq ft · 1346 THORNAPPLE DRIVE
- $175,000 · 2 bd / 2 ba / 960 sq ft · 145 EDGEWOOD DRIVE
- $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)
- $1.45M · 3 bd / 3.5 ba / 3,872 sq ft · 422 BLUE GARDEN LANE
- $319,000 · 2 bd / 2.5 ba / 1,240 sq ft · 1819 HIGHLAND ROAD
- $799,000 · 3 bd / 2.5 ba / 2,678 sq ft · 1104 MALLARD MARSH DRIVE
- $159,900 · 1 bd / 1 ba / 586 sq ft · 717 PINE RUN DR. #717
- $465,000 · 2 bd / 2 ba / 1,404 sq ft · 120 VILLA DRIVE #120
- $1.10M · 5 bd / 3.5 ba / 3,354 sq ft · 296 PINE RANCH TRAIL
- $649,000 · 3 bd / 2 ba / 2,084 sq ft · 586 OAK BAY DRIVE
- $625,000 · 3 bd / 2 ba / 1,937 sq ft · 250 HIDDEN BAY DRIVE #302
- $4.59M · 5 bd / 5 ba / 5,279 sq ft · 275 LOOKOUT POINT DRIVE (Southbay Yacht & Racquet Club)
- $449,000 · 3 bd / 2 ba / 1,883 sq ft · 7303 JESSIE HARBOR DRIVE #7303
- $1.40M · 3 bd / 3 ba / 2,594 sq ft · 385 NORTH POINT ROAD #701 (Meridian at The Oaks Preserve)
- $985,000 · 3 bd / 3 ba / 2,203 sq ft · 409 N POINT ROAD #803 (Meridian at The Oaks Preserve)
- $499,999 · 3 bd / 3 ba / 2,422 sq ft · 453 S SHORE DRIVE
- $244,900 · 2 bd / 2 ba / 1,223 sq ft · 109 WOODLAND PLACE
- $3.70M · 5 bd / 5 ba / 6,234 sq ft · 324 OSPREY POINT DRIVE
- $1.27M · 3 bd / 2 ba / 2,850 sq ft · 17 BAYHEAD LANE
- $1.59M · 3 bd / 3.5 ba / 3,565 sq ft · 402 MACEWEN DRIVE
- $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
- $950,000 · 3 bd / 1.5 ba / 2,084 sq ft · 210 PATTERSON AVENUE
- $749,900 · 3 bd / 2 ba / 2,174 sq ft · 1328 THORNAPPLE DRIVE
- $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
- $529,000 · 4 bd / 2 ba / 2,203 sq ft · 583 PINE RANCH EAST ROAD
- $630,000 · 4 bd / 2 ba / 2,186 sq ft · 1036 OAK MEADOW LANE (Rivendell)
- $1.35M · 4 bd / 4 ba / 3,255 sq ft · 1417 LANDVIEW LANE (Southbay Yacht & Racquet Club)
- $565,000 · 3 bd / 2 ba / 1,705 sq ft · 2046 CORDES STREET
- $1.10M · 4 bd / 3 ba / 3,984 sq ft · 907 EAGLE ISLE COURT
- $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
- $699,000 · 3 bd / 2 ba / 2,328 sq ft · 299 TURQUOISE LANE
- $425,000 · 2 bd / 2 ba / 1,574 sq ft · 780 SARABAY ROAD #16
- $775,000 · 3 bd / 2.5 ba / 1,950 sq ft · 260 HIDDEN BAY DRIVE #402
- $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
- $1.50M · 3 bd / 3.5 ba / 2,913 sq ft · 360 N POINT ROAD
- $4.79M · 4 bd / 5.5 ba / 5,087 sq ft · 101 OSPREY POINT DRIVE
- $480,000 · 3 bd / 2.5 ba / 2,006 sq ft · 2309 JESSIE HARBOR DRIVE #2402
- $1.59M · 4 bd / 4 ba / 4,001 sq ft · 75 OSPREY POINT DRIVE
- $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
- $700,000 · 4 bd / 3.5 ba / 2,950 sq ft · 759 FORDINGBRIDGE WAY
- $289,000 · 2 bd / 2 ba / 1,135 sq ft · 4296 EXPEDITION WAY #104
- $275,000 · 1 bd / 1 ba / 623 sq ft · 51 MACEWEN DRIVE #12
- $699,000 · 2 bd / 2 ba / 2,143 sq ft · 5100 JESSIE HARBOR DRIVE #304
- $560,000 · 3 bd / 3 ba / 2,594 sq ft · 409 NORTH POINT ROAD #401 (Meridian at The Oaks Preserve)
- $285,000 · 1 bd / 1 ba / 595 sq ft · 51 MAC EWEN DRIVE #14
- $1.29M · 3 bd / 3.5 ba / 3,112 sq ft · 156 BISHOPS COURT ROAD
- $699,000 · 3 bd / 2 ba / 2,034 sq ft · 103 BISHOPS COURT ROAD
- $1.95M · 5 bd / 5.5 ba / 4,885 sq ft · 97 SUGAR MILL DRIVE
- $499,999 · 3 bd / 2 ba / 2,004 sq ft · 4429 CONCHFISH LANE
- $719,000 · 3 bd / 2 ba / 1,937 sq ft · 280 HIDDEN BAY DRIVE #302
- $2.85M · 3 bd / 3.5 ba / 2,665 sq ft · 14401 MASTHEAD DRIVE
- $798,000 · 3 bd / 3.5 ba / 3,771 sq ft · 6100 JESSIE HARBOR DRIVE #202
- $299,000 · 2 bd / 2 ba / 1,135 sq ft · 4226 FRONTIER LANE #103
- $999,900 · 3 bd / 3 ba / 2,187 sq ft · 14021 BELLAGIO WAY #404
- $700,000 · 3 bd / 2 ba / 1,799 sq ft · 14041 BELLAGIO WAY #214
- $1.10M · 3 bd / 2.5 ba / 2,830 sq ft · 1527 BUOY LANE (Southbay Yacht & Racquet Club)
- $879,000 · 3 bd / 2.5 ba / 2,199 sq ft · 14021 BELLAGIO WAY #309
- $5.30M · 4 bd / 4.5 ba / 5,337 sq ft · 313 LOOKOUT POINT DRIVE (Southbay Yacht & Racquet Club)
- $2.40M · 4 bd / 3.5 ba / 3,953 sq ft · 49 OSPREY POINT DRIVE
- $419,000 · 3 bd / 2 ba / 1,760 sq ft · 524 SARABAY ROAD (Bay Acres Resub)
- $525,000 · 3 bd / 3 ba / 2,680 sq ft · 3621 N POINT ROAD #301 (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
- $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
- $6.10M · 4 bd / 5.5 ba / 4,096 sq ft · 121 N CASEY KEY ROAD (Casey Key)
- $2.70M · 6 bd / 6.5 ba / 6,246 sq ft · 236 SAINT JAMES PARK (The Oaks)
- $649,000 · 3 bd / 2 ba / 2,058 sq ft · 110 PINE AVENUE
- $2.40M · 3 bd / 3.5 ba / 4,519 sq ft · 852 MACEWEN DRIVE (The Oaks)
- $769,000 · 3 bd / 2 ba / 2,310 sq ft · 13 BAYHEAD LANE
- $615,000 · 3 bd / 3 ba / 2,055 sq ft · 385 N POINT ROAD #402 (Meridian at The Oaks Preserve)
- $875,000 · 3 bd / 2 ba / 2,271 sq ft · 293 TURQUOISE LANE
- $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)
- $575,000 · 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.
| ZIP | Homes for sale | Median list price |
|---|---|---|
| 34229 | 100 | $734,450 |
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.
| Community | For sale | Median list | Median sold (12 mo) | Days on market |
|---|---|---|---|---|
| Meridian at The Oaks Preserve | 13 | $695,000 | — | — |
| Southbay Yacht & Racquet Club | 7 | $1.69M | — | — |
| The Oaks | 5 | $2.40M | — | — |
| Casey Key | 3 | $6.10M | — | — |
| Rivendell | 2 | $642,500 | — | — |
| Bay Acres Resub | 1 | $419,000 | — | — |
What is for sale in Osprey: property types
- Single-family houses: 53
- Condos: 37
- Townhouses: 5
- Manufactured homes: 4
- Villas: 1
Another 7 listings in Osprey are land, commercial or other non-residential property and are not counted above.
Browse by type: Condos for sale in Osprey (37).
What a home in Osprey costs to own
Take the median $734,450 listing with 20% down at today’s 7.40% 30-year rate: principal and interest run about $4,068/month. Sarasota County’s typical millage of 13.48 puts property tax near $9,225/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 $5,014/month plus any HOA or CDD assessment.
Explore Osprey
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Homes for sale near Osprey
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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.
- 854 Macewen Drive · last listed $3,670,000 · off market Oct 14, 2026
- 547 Meadow Sweet Circle · last listed $550,000 · off market Oct 14, 2026
- 112 Osprey Point Drive · last listed $6,449,000 · off market Oct 14, 2026
- 650 Crane Prairie Way · last listed $799,990 · off market Oct 13, 2026
- 570 Blackburn Point Road #38 · last listed $32,500 · off market Oct 13, 2026
- 57 Bishops Court Road #121 · last listed $655,000 · off market Oct 13, 2026
- 447 N Shore Drive · last listed $499,000 · off market Oct 13, 2026
- 329 Bay Vista Avenue · last listed $399,000 · off market Oct 13, 2026
- 211 Woodland Drive #211 · last listed $200,000 · off market Oct 13, 2026
- 107 Sorrento Drive · last listed $425,000 · off market Oct 13, 2026
- 916 Macewen Drive · last listed $1,900,000 · off market Oct 9, 2026
- 401 N Point Road #603 · last listed $629,000 · off market Oct 9, 2026
Common questions
How many homes are for sale in Osprey, FL?
As of 2026-10-15, Momentum's MLS record shows 100 residential homes actively listed for sale in Osprey and 15 under contract. 21 of them came on the market in the last 7 days.
What is the median home price in Osprey?
The median list price of homes for sale in Osprey is $734,450, about $348 per square foot for a typical 2,247-square-foot home. Ten percent of listings are under $285K and ten percent are above $2.40M.
How long do homes take to sell in Osprey?
Homes currently listed have been on the market a median of 79 days.
What does a $734,450 home in Osprey cost per month?
Roughly $5,014 a month with 20% down at 7.40%: principal and interest of $4,068, Sarasota County property tax of about $769/month after the $50,000 homestead exemption, and insurance near $177/month at the Citizens county average. HOA or CDD fees, where they apply, come on top.
Which Osprey neighborhoods have the most homes for sale?
The communities with the most active listings right now are Meridian at The Oaks Preserve (13), Southbay Yacht & Racquet Club (7), The Oaks (5), Casey Key (3), Rivendell (2). Each community page carries its own sales history, live inventory and schools.
How do I see a home for sale in Osprey?
Every listing on this page opens a full page with all photos, the community's data and a tour request. A Momentum agent who works Osprey can show any home here, whether it is our listing or another brokerage's, at no cost to a buyer. Call (904) 351-6461 or use the form below.
Where is Osprey, FL, and what county is it in?
Osprey is in Sarasota County, Florida. Homes for sale there today carry the ZIP codes 34229. Nearby cities in the same county with homes for sale: Sarasota, North Port, Venice, Nokomis, Longboat Key.
What ZIP codes are in Osprey, FL?
Listings in Osprey are currently in 1 ZIP code: 34229. The ZIP table above shows how many homes are for sale in each and the median asking price.
How many houses are for sale in Osprey, FL?
53 single-family houses are for sale in Osprey today, out of 100 total listings (37 condos, 5 townhouses). The property-type section above breaks the inventory down, and each card opens the full listing.
How do I buy a house in Osprey, FL?
Start with the numbers: 100 homes are for sale in Osprey today at a median asking price of $734,450, so a 20% down payment on the median home is about $146,890 and principal and interest run near $4,068/month at today's 7.40% 30-year rate. Get pre-approved first, sign a written buyer agreement with your agent (required before touring since August 2024), then search by price band, ZIP or community above. Our Florida buyer closing-cost calculator itemizes the cash to close, and the Florida first-time buyer guide covers programs and down-payment help.
What county is Osprey in?
Osprey is in Sarasota County, Florida. Sarasota County's 12-month median sale price is $435K on 12,012 closings. Property tax, school zoning and permitting for Osprey run through Sarasota County.
Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Osprey as of 2026-10-15 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.