$2,100,000
- 4 Beds
- 3.5 Baths
- 3,768 Sq Ft
448 E MacEwen Dr, Osprey, FL 34229
Mark Lyda GENEROUS PROPERTY
5,118
Homes in ZIP Code 34229
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448 E MacEwen Dr, Osprey, FL 34229
-
$6,950 Per Month
- 3 Beds
- 2.5 Baths
- 1,839 Sq Ft
- Townhouse for Rent
101 Woodland Place, Osprey, FL 34229
101 Woodland Place, Osprey, FL 34229Now AVAILABLE FOR LEASE PINE RUN Condominiums in OSPREY, Florida! 3BR/2.5BA Great SARASOTA Vacation Location! West of the Trail, Pine Run is an active community set in a tropical oasis of 20+ acres of wooded Florida landscape. This spacious corner unit townhouse is well FURNISHED. Beautifully decorated and full of light and color with vaulted ceiling in the main Great Room. Custom designed
Patrice Ivan WAGNER REALTY
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$362,500
Sold Apr 09, 2026124 Revolution Way, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Built 2016
Last Sold Summary
- 9% Below List Price
- $230/SF
- 47 Days On Market
Current Estimated Value $361,988
Last Listing Agent James Briley COLDWELL BANKER REALTY
124 Revolution Way, 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
-
$799,000
$166K PRICE DROP- 3 Beds
- 2 Baths
- 2,310 Sq Ft
13 Bayhead Ln, Osprey, FL 34229
13 Bayhead Ln, Osprey, FL 34229Mark Lyda GENEROUS PROPERTY
-
$8,000 Per Month
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
- Condo for Rent
14041 Bellagio Way Unit 316, Osprey, FL 34229
14041 Bellagio Way Unit 316, Osprey, FL 34229AVAILABLE FOR SEASON 2027 - 2 MONTH MIN REQUIRED. MINUTES TO CASEY KEY & NOKOMIS BEACH! Welcome to BELLAGIO at Osprey Harbor Village, offering luxurious waterfront living! This turnkey direct waterfront condo has 3 beds/2 baths plus a den is the perfect place for your next Florida vacation, located in a private gated community. As you step off the elevator, you are basically outside this 3rd
Chrissie Cummings JENNETTE PROPERTIES INC
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$1,050,000
Sold Jul 22, 2025142 Dory Ln, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,531 Sq Ft
- Built 1984
Last Sold Summary
- 12% Below List Price
- $415/SF
- 32 Days On Market
Current Estimated Value $980,439
Last Listing Agent Sharon Lewis GOLF & BAY PROPERTIES LLC
142 Dory Ln, Osprey, FL 34229 -
Not Listed For Sale
570 Blackburn Point Rd Unit C2, Osprey, FL 34229
- Built 2005
Last Sold Summary
- 234 Days On Market
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$1,395,000
- 3 Beds
- 3 Baths
- 2,545 Sq Ft
3603 N Point Rd Unit 702, Osprey, FL 34229
3603 N Point Rd Unit 702, Osprey, FL 34229Mark Lyda GENEROUS PROPERTY
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$4,500 Per Month
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
- Condo for Rent
152 Navigation Cir Unit 107, Osprey, FL 34229
152 Navigation Cir Unit 107, Osprey, FL 34229BACIK ON THE MARKET HIGH SEASON NOW AVAILABLE!! Seasonal and short term rental Get out of the cold and into the sunshine in this newer 3/2 condo in the gated community of Bay Street Village in Osprey. This condo is an end unit with an open floor plan for ease of entertaining and family time. The extra windows flood the unit with natural sun light. The kitchen is a natural gathering point with
Cody Smith RENT SARASOTA
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$2,100,000
Sold May 14, 2026479 S Creek Dr, Osprey, FL 34229
- 5 Beds
- 5.5 Baths
- 4,261 Sq Ft
- Built 1995
Last Sold Summary
- 34% Below List Price
- $493/SF
- 135 Days On Market
Current Estimated Value $2,421,353
Last Listing Agent Michelle Hupp KELLER WILLIAMS ISLAND LIFE REAL ESTATE
479 S Creek Dr, Osprey, FL 34229 -
Est $1,072,544
Not Listed For Sale3925 Waypoint Ave, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,323 Sq Ft
- Built 2016
Last Sold Summary
- 42 Days On Market
-
$1,250,000
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
409 N Point Rd Unit 601, Osprey, FL 34229
409 N Point Rd Unit 601, Osprey, FL 34229Mark Lyda GENEROUS PROPERTY
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$3,980 Per Month
- 5 Beds
- 4.5 Baths
- 3,050 Sq Ft
- House for Rent
246 Burney Rd, Osprey, FL 34229
246 Burney Rd, Osprey, FL 34229Brand-new construction single-family home available for rent in a prime Osprey location! This spacious residence offers 5 bedrooms + 2 dedicated office/study rooms + 4.5 bathrooms + a 2-car garage, also All windows are impact-rated, eliminating the hassle of putting up hurricane shutters while providing extra security, energy efficiency, and storm protection. and ideal for large families or those
xiaoying zhang FLORIDA MORNING REALTY LLC
-
$2,100,000
Sold Jan 30, 2026889 MacEwen Dr, Osprey, FL 34229
- 4 Beds
- 4 Baths
- 3,235 Sq Ft
- Built 1994
Last Sold Summary
- 9% Below List Price
- $649/SF
- 41 Days On Market
Current Estimated Value $2,036,288
Last Listing Agent Mark Lyda GENEROUS PROPERTY
889 MacEwen Dr, Osprey, FL 34229 -
Est $1,057,718
Not Listed For Sale3937 Waypoint Ave, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,314 Sq Ft
- Built 2016
Last Sold Summary
- 63 Days On Market
-
$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
-
$3,980 Per Month
- 5 Beds
- 4.5 Baths
- 3,050 Sq Ft
- House for Rent
254 Burney Rd, Osprey, FL 34229
254 Burney Rd, Osprey, FL 34229Brand-new construction single-family home available for rent in a prime Osprey location! This spacious residence offers 5 bedrooms + 2 dedicated office/study rooms + 4.5 bathrooms + a 2-car garage, also All windows are impact-rated, eliminating the hassle of putting up hurricane shutters while providing extra security, energy efficiency, and storm protection. and ideal for large families or those
xiaoying zhang FLORIDA MORNING REALTY LLC
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$1,405,000
Sold Jul 11, 2025282 Shell Midden Ct, Osprey, FL 34229
- 3 Beds
- 4.5 Baths
- 3,699 Sq Ft
- Built 1992
Last Sold Summary
- 17% Below List Price
- $380/SF
- 128 Days On Market
Current Estimated Value $1,416,362
Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
282 Shell Midden Ct, Osprey, FL 34229 -
Est $281,211
Not Listed For Sale101 Navigation Cir Unit 101, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Built 2014
Last Sold Summary
- 80 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
- Condo for Rent
260 Hidden Bay Dr Unit B 401, Osprey, FL 34229
260 Hidden Bay Dr Unit B 401, 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
Jaime Barcelo GULF COAST REALTY & MANAGEMENT
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$1,330,000
Sold Jan 07, 2026401 N Point Rd Unit 901, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
- Built 2003
Last Sold Summary
- 24% Below List Price
- $513/SF
- 764 Days On Market
Current Estimated Value $1,281,660
Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
401 N Point Rd Unit 901, Osprey, FL 34229 -
Est $299,490
Not Listed For Sale163 Explorer Dr Unit 103, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Built 2014
Last Sold Summary
- 28 Days On Market
-
$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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$3,500 Per Month
- 3 Beds
- 2 Baths
- 1,648 Sq Ft
- House for Rent
2068 Preymore St, Osprey, FL 34229
2068 Preymore St, Osprey, FL 34229Welcome home to this charming and beautifully maintained 3-bedroom, 2-bath residence located on a great community. Step inside to a spacious open floor plan featuring a generous great room, a dedicated dining area, and a large primary suite. Cathedral ceilings, pocket sliding doors, and fluid room transitions create an airy atmosphere perfect for easy living and entertaining. The bright, eat-in
Kenia Rivas PREFERRED SHORE LLC
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$110,000
Sold May 14, 2026234 Palm Air Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 987 Sq Ft
- Built 1984
Last Sold Summary
- 8% Below List Price
- $111/SF
- 30 Days On Market
Last Listing Agent Toni Zarghami KW COASTAL LIVING III
234 Palm Air Dr, Osprey, FL 34229 -
Not Listed For Sale
201 Palm Air Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Built 1980
Last Sold Summary
- 119 Days On Market
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$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
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$2,300 Per Month
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Condo for Rent
4219 Frontier Ln Unit 105, Osprey, FL 34229
4219 Frontier Ln Unit 105, Osprey, FL 342292 bedrooms. 2 baths, 1 car garage. Condo Unfurnished. Available July 1, 2026. Tenant Occupied until June 22, 2026. 2nd floor. Close to Beaches! Located 10 minutes to Nokomis Beach/Casey Key Beach or 15 minutes to Siesta Key Beach. Minutes by bike to Legacy Trail and Casey Key. Water, Sewer & trash included in the rent. This maintenance free community includes gated entry, resort style community
Tim Weller EXIT KING REALTY
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$962,500
Sold Aug 07, 2025742 Shadow Bay Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,321 Sq Ft
- Built 2002
Last Sold Summary
- 12% Below List Price
- $290/SF
- 115 Days On Market
Current Estimated Value $975,983
Last Listing Agent Reeny Kaney RE/MAX ALLIANCE GROUP
742 Shadow Bay Way, Osprey, FL 34229 -
Est $555,538
Not Listed For Sale2007 Cordes St, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
- Built 2023
Last Sold Summary
- 15 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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$3,595 Per Month
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
- Condo for Rent
280 Hidden Bay Dr Unit 202, Osprey, FL 34229
280 Hidden Bay Dr Unit 202, Osprey, FL 34229Be the first to call this brand-new condo in Edgewater at Hidden Bay home. The kitchen showcases a sleek, modern design, complemented by solid wood cabinetry and quartz countertops, creating an ideal space for both everyday living and effortless entertaining. Appliances include a stainless-steel refrigerator, microwave, range, and dishwasher. Large windows bring in an abundance of natural light
Nancy Guerrero PMI SOUTHWEST FLORIDA
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$210,000
Sold Oct 22, 2025480 Blackburn Point Rd Unit 4, Osprey, FL 34229
- Built 2006
Last Sold Summary
- 7% Below List Price
- 5 Days On Market
Current Estimated Value $210,914
Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY
480 Blackburn Point Rd Unit 4, Osprey, FL 34229 -
Est $753,762
Not Listed For Sale280 Hidden Bay Dr Unit 303, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
- Built 2025
Last Sold Summary
- 27 Days On Market
-
$725,000
$10K PRICE DROP- 2 Beds
- 2 Baths
- 2,143 Sq Ft
5100 Jessie Harbor Dr Unit 304, Osprey, FL 34229
5100 Jessie Harbor Dr Unit 304, Osprey, FL 34229Suki Scollo COLDWELL BANKER REALTY
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$4,500 Per Month
- 3 Beds
- 2 Baths
- 2,367 Sq Ft
- House for Rent
1355 Southbay Dr, Osprey, FL 34229
1355 Southbay Dr, Osprey, FL 34229Southbay Yacht & Racquet Club where the true Florida lifestyle is alive and well! This three-bedroom two bath pool home is located in an active community with unmatched amenities such as an active social atmosphere, heated community pool, playground, fitness room, tennis, pickleball courts, and fishing. All for you to enjoy! Walk, bike or take your golf cart to restaurants, shopping or the
Sharon Lewis GOLF & BAY PROPERTIES LLC
-
$980,000
Sold Dec 09, 2025385 N Point Rd Unit 903, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
- Built 2000
Last Sold Summary
- 11% Below List Price
- $353/SF
- 41 Days On Market
Current Estimated Value $1,016,189
Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY
385 N Point Rd Unit 903, Osprey, FL 34229 -
Not Listed For Sale
0 N Point Rd Unit A11454780, Osprey, FL 34229
Last Sold Summary
- 218 Days On Market
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