$260,000
$30K PRICE DROP
Under Contract
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
4271 Expedition Way Unit 103, Osprey, FL 34229
Toni Zarghami
KW COASTAL LIVING III
5,018
Osprey, FL Homes
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4271 Expedition Way Unit 103, Osprey, FL 34229
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$2,500 Per Month
- 1 Bed
- 1 Bath
- 623 Sq Ft
- Condo for Rent
51 Mac Ewen Dr Unit 1, Osprey, FL 34229
51 Mac Ewen Dr Unit 1, Osprey, FL 34229 -
$900,000
Sold Jan 16, 20263957 Waypoint Ave, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,328 Sq Ft
- Built 2018
Last Sold Summary
- 6% Below List Price
- $387/SF
- 35 Days On Market
Current Estimated Value $927,379
Last Listing Agent Leonard Giarrano RE/MAX ALLIANCE GROUP
3957 Waypoint Ave, Osprey, FL 34229 -
Est $662,722
Not Listed For Sale463 Park Trace Blvd, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,153 Sq Ft
- Built 2002
Last Sold Summary
- 63 Days On Market
Last Listing Agent Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY
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$289,900
$60K PRICE DROP- 2 Beds
- 2 Baths
- 1,165 Sq Ft
1801 Highland Rd, Osprey, FL 34229
1801 Highland Rd, Osprey, FL 34229
Kimberly Werla
RE/MAX ALLIANCE GROUP
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$1,900 Per Month
- 2 Beds
- 2 Baths
- 1,325 Sq Ft
- Condo for Rent
236 Woodland Dr, Osprey, FL 34229
236 Woodland Dr, Osprey, FL 34229Property Id: 310276 IN 2026, AVAILABLE SEP 10 to OCT 10. IN 2027, AVAILABLE BEGINNING MAY 15. Light, airy home in Pine Run overlooks established native landscaping. Copious sliding doors, windows & high ceilings. Beautifully updated kitchen offer views to outdoors. Carport + 1 visitor parking space. A nature lovers paradise, this laid-back, quiet & desirable community is close to Casey Key,
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$452,500
Sold Aug 29, 2025784 Sarabay Rd, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Built 1981
Last Sold Summary
- 38% Below List Price
- $287/SF
- 257 Days On Market
Current Estimated Value $427,378
Last Listing Agent Peggy Lewis COLDWELL BANKER SARASOTA CENT.
784 Sarabay Rd, Osprey, FL 34229 -
Est $1,031,570
Not Listed For Sale3961 Waypoint Ave, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,346 Sq Ft
- Built 2018
Last Sold Summary
- 213 Days On Market
Last Listing Agent Lee Brewer RE/MAX ALLIANCE GROUP
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$215,000
$10K PRICE DROP- 2 Beds
- 2 Baths
- 1,325 Sq Ft
110 Woodland Place, Osprey, FL 34229
110 Woodland Place, Osprey, FL 34229
Echo Belser PA
COLDWELL BANKER REALTY
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$5,000 Per Month
- 2 Beds
- 2 Baths
- 1,568 Sq Ft
- Condo for Rent
293 Hidden Bay Dr Unit 203, Osprey, FL 34229
293 Hidden Bay Dr Unit 203, Osprey, FL 34229 -
$600,000
Sold May 26, 2026522 Luminary Blvd, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,320 Sq Ft
- Built 2005
Last Sold Summary
- 7% Below List Price
- $259/SF
- 88 Days On Market
Current Estimated Value $603,886
Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
522 Luminary Blvd, Osprey, FL 34229 -
Est $985,311
Not Listed For Sale3904 Waypoint Ave, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,344 Sq Ft
- Built 2016
Last Sold Summary
- 161 Days On Market
Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
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$700,000
- 3 Beds
- 2 Baths
- 1,799 Sq Ft
14041 Bellagio Way Unit 214, Osprey, FL 34229
14041 Bellagio Way Unit 214, Osprey, FL 34229
Veronica Lee
COLDWELL BANKER REALTY
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$775 Per Month
- 1 Bed
- 1 Bath
- House for Rent
8 Bay Ave, Osprey, FL 34229
8 Bay Ave, Osprey, FL 34229Property Id: 1524644 Unfurnished Room with private bath for rent, for 1 person, utilities included. No pets, no alcohol drinks, no drugs, no visitors allowed inside the house. House rules to follow, NO EXCEPTIONS Landlord requires 1st, last month rent plus $455 security deposit due at the sign of the lease. Information to verify employment, references from previous landlord and
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$865,000
Sold Feb 10, 202638 W Bay St, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,124 Sq Ft
- Built 1994
Last Sold Summary
- 6% Below List Price
- $407/SF
- 107 Days On Market
Current Estimated Value $841,344
Last Listing Agent Mitch Helmuth HARRY ROBBINS ASSOC INC
38 W Bay St, Osprey, FL 34229 -
Est $1,044,512
Not Listed For Sale3973 Waypoint Ave, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,377 Sq Ft
- Built 2018
Last Sold Summary
- 84 Days On Market
Last Listing Agent Carlo Costantini DAVE JONES REALTY, LLC
-
$2,850,000
$350K PRICE DROP- Land
- 16,988 Sq Ft
- $7,307,692 per Acre
141 N Casey Key Rd, Osprey, FL 34229
141 N Casey Key Rd, Osprey, FL 34229 -
$5,157
Total Monthly Price
- 4 Beds
- 2 Baths
- 2,389 Sq Ft
- Condo for Rent
111 Tina Island Dr Unit SI ID1591462P, Osprey, FL 34229
111 Tina Island Dr Unit SI ID1591462P, Osprey, FL 34229The advertised rate of $5,157/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
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$75,000
Sold Dec 12, 2025570 Blackburn Point Rd Unit 2, Osprey, FL 34229
- Built 2006
Last Sold Summary
- 5% Below List Price
- 17 Days On Market
Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY
570 Blackburn Point Rd Unit 2, Osprey, FL 34229 -
Est $598,077
Not Listed For Sale4421 Conchfish Ln, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,133 Sq Ft
- Built 2017
Last Sold Summary
- 38 Days On Market
Last Listing Agent Rory McDonald PREFERRED SHORE LLC
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$399,000
$46K PRICE DROP- 2 Beds
- 2 Baths
- 1,346 Sq Ft
329 Bay Vista Ave, Osprey, FL 34229
329 Bay Vista Ave, Osprey, FL 34229
Rodrigo Posada
THE SHORELINE FL REALTY LLC
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$1,600 Per Month
- 1 Bed
- 1 Bath
- 595 Sq Ft
- Condo for Rent
51 Mac Ewen Dr Unit 8, Osprey, FL 34229
51 Mac Ewen Dr Unit 8, Osprey, FL 34229Come lounge around in one of the finest golf communities where everyday can feel like a vacation. This elegant loft has a lovely view of the lake with the rolling green right behind it. Enjoy endless summer days basking in the sun at the pool which is only steps away! This loft is equipped with granite countertops, a full size washer and dryer, stainless steel appliances, fixtures and fittings, a
Deserea Hardy ROSSI & COMPANY INC
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$220,000
Sold Aug 07, 2026480 Blackburn Point Rd Unit 5, Osprey, FL 34229
- Built 2006
Last Sold Summary
- 12% Below List Price
- 3 Days On Market
Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY
480 Blackburn Point Rd Unit 5, Osprey, FL 34229 -
Est $752,100
Not Listed For Sale148 Osprey Point Dr, Osprey, FL 34229
Last Sold Summary
- 375 Days On Market
Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN
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$1,500,000
$195K PRICE DROP Pending- 3 Beds
- 3.5 Baths
- 3,208 Sq Ft
480 Oriskany Ct, Osprey, FL 34229
480 Oriskany Ct, Osprey, FL 34229
Susan Pelton
MICHAEL SAUNDERS & COMPANY
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$5,157
Total Monthly Price
- 4 Beds
- 2 Baths
- 2,389 Sq Ft
- Condo for Rent
111 Tina Island Dr Unit SI ID1591462P, Osprey, FL 34229
111 Tina Island Dr Unit SI ID1591462P, Osprey, FL 34229The advertised rate of $5,157/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 27, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
-
$1,850,000
Sold Jan 22, 2026453 E MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 4,191 Sq Ft
- Built 1999
Last Sold Summary
- 8% Below List Price
- $441/SF
- 19 Days On Market
Current Estimated Value $1,842,317
Last Listing Agent William Kelly THE REAL ESTATE STORE
453 E MacEwen Dr, Osprey, FL 34229 -
Est $1,106,012
Not Listed For Sale3932 Waypoint Ave, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,416 Sq Ft
- Built 2017
Last Sold Summary
- 11 Days On Market
Last Listing Agent Larry Brzostek RE/MAX ALLIANCE GROUP
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$1,100,000
- 5 Beds
- 3 Baths
- 3,912 Sq Ft
674 Clear Creek Dr, Osprey, FL 34229
674 Clear Creek Dr, Osprey, FL 34229
Arkadiy Abdurakhmanov
United Realty Group Inc.
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$2,300 Per Month
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Property for Rent
184 Explorer Dr Unit 184, Osprey, FL 34229
184 Explorer Dr Unit 184, Osprey, FL 34229Property available for $2300 from April 1,2024 till November 30,2024. Tenant pays electricity and internet. Available for season 2024/2025 for $4500. If you are looking for the perfect Florida lifestyle, this is it. Conveniently located between Sarasota and Venice with #1 Siesta Key beach close by, this darling two-bedroom, two-bath, impeccably maintained, property move-in ready. Located on the
Claudia Dybala DALTON WADE INC
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$669,000
Sold Apr 07, 2026146 Willow Bend Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,540 Sq Ft
- Built 2002
Last Sold Summary
- 4% Below List Price
- $263/SF
- 26 Days On Market
Current Estimated Value $677,234
Last Listing Agent Maria Rocha KELLER WILLIAMS ON THE WATER S
146 Willow Bend Way, Osprey, FL 34229 -
Est $141,681
Not Listed For Sale570 Blackburn Point Rd Unit 27, Osprey, FL 34229
- Studio
- Built 2006
Last Sold Summary
- 23 Days On Market
Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY
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$175,000
$15K PRICE DROP- Land
- 20,908 Sq Ft
- $364,583 per Acre
14 Old Venice Rd, Osprey, FL 34229
14 Old Venice Rd, Osprey, FL 34229 -
$4,800 Per Month
- 4 Beds
- 3 Baths
- 2,290 Sq Ft
- House for Rent
956 Scherer Way, Osprey, FL 34229
956 Scherer Way, Osprey, FL 34229This FULLY FURNISHED 4 bedroom, 3 bathroom rental home is available for an ANNUAL LEASE in a quiet HOA community with a PRIVATE HEATED POOL, HOT TUB, 3-CAR GARAGE, and great access to everything Sarasota/Osprey has to offer!- This home has the perfect Florida living setup with a backyard overlooking natural Florida views that you can enjoy from your SCREENED-IN LANAI.- Inside, enjoy
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$1,025,000
Sold Apr 24, 20261218 Yacht Harbor Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 3,297 Sq Ft
- Built 1980
Last Sold Summary
- 15% Below List Price
- $311/SF
- 203 Days On Market
Current Estimated Value $1,037,765
Last Listing Agent Karie Backman KELLER WILLIAMS ON THE WATER S
1218 Yacht Harbor Dr, Osprey, FL 34229 -
Est $521,493
Not Listed For Sale622 Pine Ranch Rd E, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,302 Sq Ft
- Built 1995
Last Sold Summary
- 50 Days On Market
Last Listing Agent Terri Persing PARADISE EXCLUSIVE REAL ESTATE
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$1,595,000
$200K PRICE DROP- 3 Beds
- 3.5 Baths
- 4,241 Sq Ft
909 MacEwen Dr, Osprey, FL 34229
909 MacEwen Dr, Osprey, FL 34229Mark Lyda GENEROUS PROPERTY
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$5,900 Per Month
- 3 Beds
- 3 Baths
- 2,545 Sq Ft
- Condo for Rent
3603 N Point Rd Unit 602, Osprey, FL 34229
3603 N Point Rd Unit 602, Osprey, FL 34229**FURNISHED, 3-BED / 3-FULL BATH, Over 2500sf CONDO with FANTASTIC VIEW** features an Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Spacious interior which boasts beautiful Crown Moldings, Hardwood Floors, a well-equipped Kitchen with granite
Mark Lyda GENEROUS PROPERTY
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$480,000
Sold Mar 18, 2026827 Placid Lake Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,875 Sq Ft
- Built 2002
Last Sold Summary
- 16% Below List Price
- $256/SF
- 202 Days On Market
Current Estimated Value $490,617
Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY
827 Placid Lake Dr, Osprey, FL 34229 -
Est $955,711
Not Listed For Sale336 Pine Ranch Rd E, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,705 Sq Ft
- Built 1989
Last Sold Summary
- 5 Days On Market
Last Listing Agent Marco Guadagnini PREFERRED SHORE LLC
Showing Results 1 - 40, Page 1 of 18
Home Prices in Osprey, FL
The median home sale price in Osprey, FL is $660,000, down 13% year-over-year. Homes in Osprey sell in 95 days on average, compared to the national average of 55 days.
Home Price Trends
|
Median Sale Price
$660,000
|
Median Single Family Sale Price
$780,000
|
|
Median Townhouse Sale Price
$435,000
|
Median 2 Bedroom Sale Price
$335,000
|
|
Median 1 Bedroom Sale Price
$200,000
|
Average Price Per Sq Ft
$361
|
|
Number of Homes for Sale
79
|
Last 12 months Home Sales
198
|
|
Months of Supply
4.80
|
Median List Price
$739,900
|
|
Median Change From 1st List Price
7%
|
Median Home Sale Price YoY Change
-13%
|
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