$270,000
$20K PRICE DROP
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
4271 Expedition Way Unit 103, Osprey, FL 34229
Toni Zarghami
KW COASTAL LIVING III
5,082
Osprey, FL Homes
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4271 Expedition Way Unit 103, Osprey, FL 34229
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$14,000 Per Month
- 4 Beds
- 6 Baths
- 9,081 Sq Ft
- House for Rent
854 MacEwen Dr, Osprey, FL 34229
854 MacEwen Dr, Osprey, FL 34229Set on a quiet private cul-de-sac in The Oaks, this beautifully revitalized estate embodies the elegance of refined Florida living. Bright, open interiors and thoughtful updates create a welcoming flow from the chefs kitchen through the main living areas and out to the lanai, where sweeping golf course views frame the heated pool, spa, and fully equipped outdoor kitchen perfect for year-round
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$727,500
Sold Feb 12, 2026260 Hidden Bay Dr Unit B 305, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 2,168 Sq Ft
- Built 2019
Last Sold Summary
- 17% Below List Price
- $336/SF
- 257 Days On Market
Current Estimated Value $736,121
Last Listing Agent Cathy Rustin FIRST LIGHT REAL ESTATE
260 Hidden Bay Dr Unit B 305, Osprey, FL 34229 -
Est $257,538
Not Listed For Sale51 MacEwen Dr Unit 20, Osprey, FL 34229
- 1 Bed
- 1 Bath
- 623 Sq Ft
- Built 1990
Last Sold Summary
- 0 Days On Market
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$540,000
- 4 Beds
- 2 Baths
- 2,399 Sq Ft
523 Oak Bay Dr, Osprey, FL 34229
523 Oak Bay Dr, Osprey, FL 34229
Karie Backman
KELLER WILLIAMS ON THE WATER S
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$4,500 Per Month
- 3 Beds
- 2 Baths
- 2,306 Sq Ft
- House for Rent
124 Turquoise Ln, Osprey, FL 34229
124 Turquoise Ln, Osprey, FL 34229**RENT JUST LOWERED**Impressive three-bedroom, two-bathroom home with heated pool designed for both comfortable family living and grand-scale entertaining. High-speed internet is now included. Ideally situated on a quiet cul-de-sac in Emerald Woods at The Oaks, this gated, beautifully landscaped community features serene lakes throughout and offers a prime location just minutes from Siesta Key
Cody Smith RENT SARASOTA
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$1,750,000
Sold Oct 27, 2025627 N MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 4.5 Baths
- 3,857 Sq Ft
- Built 2000
Last Sold Summary
- 10% Below List Price
- $454/SF
- 1 Day On Market
Current Estimated Value $1,736,825
Last Listing Agent Mark Lyda GENEROUS PROPERTY
627 N MacEwen Dr, Osprey, FL 34229 -
Est $619,419
Not Listed For Sale610 Pine Ranch Rd E, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,431 Sq Ft
- Built 1995
Last Sold Summary
- 113 Days On Market
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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 -
$2,599 Per Month
- 2 Beds
- 2 Baths
- 1,500 Sq Ft
- The Residences of Blackburn Bay
2090 S Tamiami Trail Unit 303, Osprey, FL 34229
2090 S Tamiami Trail Unit 303, Osprey, FL 34229 -
$650,000
Sold Jul 03, 2025236 Hidden Bay Dr Unit 301, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,100 Sq Ft
- Built 1997
Last Sold Summary
- 13% Below List Price
- $310/SF
- 246 Days On Market
Current Estimated Value $649,455
Last Listing Agent Linda Scheller COLDWELL BANKER REALTY
236 Hidden Bay Dr Unit 301, Osprey, FL 34229 -
Est $238,891
Not Listed For Sale51 MacEwen Dr Unit 13, Osprey, FL 34229
- 1 Bed
- 1 Bath
- 595 Sq Ft
- Built 1990
Last Sold Summary
- 0 Days On Market
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$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 -
$3,775 Per Month
- 3 Beds
- 2.5 Baths
- 2,168 Sq Ft
- Condo for Rent
280 Hidden Bay Dr Unit 201, Osprey, FL 34229
280 Hidden Bay Dr Unit 201, Osprey, FL 34229Be the first to live in this brand-new stunning condo in the community of Edgewater at Hidden Bay! Sorry, no pets for renters. The kitchen features a sleek and modern look, equipped with stainless steel appliances, including a refrigerator, microwave, stove, and dishwasher, paired with solid wood cabinetry and elegant quartz countertops, creating an ideal space for both everyday living and
Nancy Guerrero PMI SOUTHWEST FLORIDA
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$635,000
Sold May 15, 2026120 Candyce Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,103 Sq Ft
- Built 1962
Last Sold Summary
- 25% Below List Price
- $302/SF
- 155 Days On Market
Current Estimated Value $651,646
Last Listing Agent Michelle Ward COMPASS FLORIDA LLC
120 Candyce Dr, Osprey, FL 34229 -
Est $830,002
Not Listed For Sale124 Tina Island Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,112 Sq Ft
- Built 1975
Last Sold Summary
- 244 Days On Market
-
$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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$4,500 Per Month
- 4 Beds
- 3 Baths
- 2,290 Sq Ft
- Annual Rental: Luxurious 4 Bedroom 3 bath POOL home in Woodlands of Rivendell! Just Blocks form P...
919 Scherer Way, Osprey, FL 34229
919 Scherer Way, Osprey, FL 34229Moving Deal! Sign a lease by July 1st at a better price of $4,300! Perfect Family Pool Home in a Location you can't ignore. Just a few blocks from The Oaks, one of the most exclusives areas in Sarasota, this impeccable home has 4 bedrooms and 3 bathrooms, 3 car garage, with just under 2,300 square feet of living area for your quiet enjoyment or entertaining friends and family. The home offers a
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$1,495,000
Sold Apr 14, 2026554 Dove Pointe, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 3,501 Sq Ft
- Built 2002
Last Sold Summary
- $427/SF
- 2 Days On Market
Current Estimated Value $1,500,658
Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY
554 Dove Pointe, Osprey, FL 34229 -
Est $93,635
Not Listed For Sale570 Blackburn Point Rd Unit Siesta 40, Osprey, FL 34229
- Studio
Last Sold Summary
- 104 Days On Market
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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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$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 34229Stunning 4-bedroom, fully furnished pool home backing directly to the tropical preserve of Oscar Scherer State Park in the highly desirable Woodlands at Rivendell. Enjoy privacy, serene views, and resort-style living within a beautifully maintained community featuring 400+ acres of lakes, walking trails, playground, and heated community pool. Prime location — walking distance to Pine View School
Chantelle Edalgo EXIT KING REALTY
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$163,000
Sold Mar 06, 2026334 Tropic Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,143 Sq Ft
- Built 1978
Last Sold Summary
- 7% Below List Price
- $143/SF
- 2 Days On Market
Last Listing Agent Laura Guess-Fox COLDWELL BANKER REALTY
334 Tropic Dr, Osprey, FL 34229 -
Est $279,749
Not Listed For Sale153 Navigation Cir Unit 106, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Built 2014
Last Sold Summary
- 150 Days On Market
-
$1,289,000
Open Sun 1PM - 3PM- 3 Beds
- 3.5 Baths
- 3,112 Sq Ft
156 Bishopscourt Rd, Osprey, FL 34229
156 Bishopscourt Rd, Osprey, FL 34229Joel Schemmel DOUGLAS ELLIMAN
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$4,850 Per Month
- 3 Beds
- 2.5 Baths
- 2,168 Sq Ft
- Coastal Luxury at Hidden Bay | 3BR Waterfront Condo with Bay Views
260 Hidden Bay Dr, Osprey, FL 34229
260 Hidden Bay Dr, Osprey, FL 342296 Month Minimum Lease Available. Experience the beauty of Florida’s Gulf Coast from this spacious, fully furnished 3-bedroom, 2.5-bath waterfront condominium overlooking Little Sarasota Bay. Thoughtfully designed for both comfort and flexibility, the home includes a private den or home office, convenient in-unit laundry, and generous living spaces perfect for relaxing or entertaining. Nestled
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$1,065,000
Sold Feb 20, 20261235 Yacht Harbor Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,698 Sq Ft
- Built 1984
Last Sold Summary
- 9% Below List Price
- $395/SF
- 30 Days On Market
Current Estimated Value $1,068,182
Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC
1235 Yacht Harbor Dr, Osprey, FL 34229 -
Est $473,025
Not Listed For Sale19 Westview Dr, Osprey, FL 34229
- 2 Beds
- Built 1990
Last Sold Summary
- 114 Days On Market
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$2,189,000
Open Sun 1PM - 3PM $61K PRICE DROP- 4 Beds
- 3.5 Baths
- 4,012 Sq Ft
433 E MacEwen Dr, Osprey, FL 34229
433 E MacEwen Dr, Osprey, FL 34229Mark Lyda GENEROUS PROPERTY
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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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$830,000
Sold Jun 16, 20266100 Jessie Harbor Dr Unit 603, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,630 Sq Ft
- Built 2005
Last Sold Summary
- 8% Below List Price
- $316/SF
- 82 Days On Market
Current Estimated Value $827,335
Last Listing Agent Andrea Stultz ENGEL + VOELKERS SARASOTA
6100 Jessie Harbor Dr Unit 603, Osprey, FL 34229 -
Est $316,220
Not Listed For Sale76 Explorer Dr Unit 104, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,430 Sq Ft
- Built 2017
Last Sold Summary
- 34 Days On Market
-
$2,395,000
$155K PRICE DROP- 3 Beds
- 3.5 Baths
- 4,519 Sq Ft
852 MacEwen Dr, Osprey, FL 34229
852 MacEwen Dr, Osprey, FL 34229Mark Lyda GENEROUS PROPERTY
-
$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
-
$4,000,000
Sold Apr 09, 2026854 N Casey Key Rd, Osprey, FL 34229
- 4 Beds
- 4 Baths
- 3,462 Sq Ft
- Built 1975
Last Sold Summary
- 16% Below List Price
- $1,155/SF
- 27 Days On Market
Last Listing Agent Charles Ruck POTTER TRINITY
854 N Casey Key Rd, Osprey, FL 34229 -
Not Listed For Sale
0 N Point Rd Unit MFRA4600038, Osprey, FL 34229
Last Sold Summary
- 52 Days On Market
-
$1,995,000
- 3 Beds
- 3 Baths
- 3,029 Sq Ft
401 N Point Rd Unit 1001, Osprey, FL 34229
401 N Point Rd Unit 1001, Osprey, FL 34229Mark Lyda GENEROUS PROPERTY
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$3,900 Per Month
- 3 Beds
- 3 Baths
- 2,055 Sq Ft
- Condo for Rent
409 N Point Rd Unit 802, Osprey, FL 34229
409 N Point Rd Unit 802, Osprey, FL 34229Move right into this gorgeous remodeled turnkey furnished condo in desirable gated community of The Oaks Preserve. This community is waterfront on the Intercostal Waterway with soothing stunning views and sunsets to adore. Take the elevator directly up to your front foyer to your unit. This unit is filled with beaming natural light and upscaled furnishings through out. The new oak wood flooring,
toyia Youtzy JENNETTE PROPERTIES, INC.
-
$155,000
Sold Apr 14, 2026316 Tropic Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,151 Sq Ft
- Built 1979
Last Sold Summary
- 16% Below List Price
- $135/SF
- 36 Days On Market
Last Listing Agent Karen Geiger COLDWELL BANKER SARASOTA CENT.
316 Tropic Dr, Osprey, FL 34229 -
Est $555,243
Not Listed For Sale221 Sorrento Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,935 Sq Ft
- Built 1984
Last Sold Summary
- 68 Days On Market
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