Osprey, FL Homes

/69
$1,995,000
- 4 Beds
- 4 Baths
- 2,572 Sq Ft
312 Yacht Harbor Dr, Osprey, FL 34229

One or more photo(s) has been virtually staged. Directly across the street from one of the most exceptional community-owned marinas on Florida’s west coast, this beautifully renovated waterfront residence offers remarkable views and an extraordinary boating lifestyle within Southbay Yacht and Racquet Club. Considered one of the finest private residential marinas in the region, Southbay’s

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

312 Yacht Harbor Dr, Osprey, FL 34229
/25
$4,500 per month
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
- Condo for Rent
152 Navigation Cir Unit 107, Osprey, FL 34229

BACIK 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

152 Navigation Cir Unit 107, Osprey, FL 34229
/2
$904,900 Sold May 30, 2025

336 Pine Ranch Rd E, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,705 Sq Ft
- Built 1989
Last Sold Summary
- 9% Below List Price
- $335/SF
- 5 Days On Market
Current Estimated Value $892,441

Last Listing Agent Marco Guadagnini PREFERRED SHORE LLC

336 Pine Ranch Rd E, Osprey, FL 34229

/2
Est $283,493 Not Listed For Sale

128 Navigation Cir Unit 103, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Built 2016
128 Navigation Cir Unit 103, Osprey, FL 34229

Last Sold Summary
- 11% Below List Price
- $255/SF
- 5 Days On Market
Last Sold Price $317,500

Last Listing Agent Tim Weller EXIT KING REALTY

/50
$899,000
- 3 Beds
- 2.5 Baths
- 2,168 Sq Ft
260 Hidden Bay Dr Unit B 405, Osprey, FL 34229

Built in 2019 and perfectly positioned on the fourth floor, this waterfront residence offers sweeping views across the Intracoastal Waterway, tranquil mangroves, and surrounding waterways from nearly every room. Designed with comfort and functionality in mind, the three-bedroom plus office layout spans nearly 2,200 square feet of interior living space and captures the essence of relaxed coastal

Roger Pettingell COLDWELL BANKER REALTY

260 Hidden Bay Dr Unit B 405, Osprey, FL 34229
/21
$2,300 per month
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Property for Rent
184 Explorer Dr Unit 184, Osprey, FL 34229

Property 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

184 Explorer Dr Unit 184, Osprey, FL 34229
/2
$430,000 Sold Aug 01, 2025

117 Villa Dr Unit 117, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,411 Sq Ft
- Built 1967
Last Sold Summary
- 22% Below List Price
- $305/SF
- 244 Days On Market
Current Estimated Value $392,484

Last Listing Agent Bill Garrison RE/MAX PALM

117 Villa Dr Unit 117, Osprey, FL 34229

/17
Est $290,852 Not Listed For Sale

4247 Expedition Way Unit 103, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Built 2016
4247 Expedition Way Unit 103, Osprey, FL 34229

Last Sold Summary
- 18% Below List Price
- $285/SF
- 89 Days On Market
Last Sold Price $355,000

Last Listing Agent Uli Wills WILLS REAL ESTATE LLC

/48
$699,000
- 3 Beds
- 2 Baths
- 2,032 Sq Ft
242 Hidden Bay Dr Unit 302, Osprey, FL 34229

Enjoy breathtaking water views and unforgettable sunsets over Little Sarasota Bay from this spacious three-bedroom condominium with an office, on the third floor with convenient elevator access. This beautifully appointed residence is in the exclusive, gated Hidden Bay community, a waterfront gem. The open floor plan features soaring ceilings, PGT impact windows, sliding glass doors, new

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

242 Hidden Bay Dr Unit 302, Osprey, FL 34229
/2
$1,051,025 Sold Apr 04, 2025

280 Hidden Bay Dr Unit 502, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
- Built 2024
Last Sold Summary
- 2% Above List Price
- $543/SF
- 2 Days On Market
Current Estimated Value $937,792

Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

280 Hidden Bay Dr Unit 502, Osprey, FL 34229

/39
Not Listed For Sale

169 Edgewood Dr, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,664 Sq Ft
- Built 2016
169 Edgewood Dr, Osprey, FL 34229

Last Sold Summary
- $165/SF
- 372 Days On Market
Last Sold Price $275,000

Last Listing Agent Christy Neff Michael Saunders

/50
$1,495,000 Pending
- 4 Beds
- 3.5 Baths
- 3,501 Sq Ft
554 Dove Pointe, Osprey, FL 34229

Located on a quiet cul-de-sac within the gates of The Oaks Clubside, this custom-built residence at 554 Dove Pointe offers privacy, space, and the refined lifestyle of one of Sarasota County’s most established country club communities. Set on a beautifully landscaped homesite covering more than a half-acre, the property enjoys exceptional curb appeal with a circular drive, mature trees, and a

Roger Pettingell COLDWELL BANKER REALTY

554 Dove Pointe, Osprey, FL 34229
/2
$689,000 Sold Mar 06, 2026

162 Willow Bend Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 2,661 Sq Ft
- Built 2004
Last Sold Summary
- $259/SF
- 4 Days On Market
Current Estimated Value $743,472

Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

162 Willow Bend Way, Osprey, FL 34229

/27
Est $348,603 Not Listed For Sale

4260 Expedition Way Unit 4260, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 1,581 Sq Ft
- Built 2017
4260 Expedition Way Unit 4260, Osprey, FL 34229

Last Sold Summary
- 20% Below List Price
- $275/SF
- 94 Days On Market
Last Sold Price $435,000

Last Listing Agent Thomas Cail RE/MAX

/50
$699,000
- 3 Beds
- 3 Baths
- 3,147 Sq Ft
3603 N Point Rd Unit 202, Osprey, FL 34229

**ELEGANT and SPACIOUS CORNER CONDO UNIT – NEARLY 3200sf – With MULTIPLE BALCONIES** found behind the gates of the highly sought after Oaks-Preserve neighborhood. This Light and Bright Open Floorplan offers 3 En Suite Bedrooms, 3 Baths, 2 assigned Parking spaces including 1 under building, Climate-controlled storage and much more! Crown moldings, engineered hardwood floors, expansive kitchen with

Mark Lyda GENEROUS PROPERTY

3603 N Point Rd Unit 202, Osprey, FL 34229
/2
$525,000 Sold Dec 04, 2025

1313 Thornapple Dr, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,082 Sq Ft
- Built 2003
Last Sold Summary
- 3% Below List Price
- $252/SF
- 8 Days On Market
Current Estimated Value $527,070

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1313 Thornapple Dr, Osprey, FL 34229

/24
Est $553,846 Not Listed For Sale

2001 Cordes St, Osprey, FL 34229
- 3 Beds
- 2.5 Baths
- 1,975 Sq Ft
- Built 2023
2001 Cordes St, Osprey, FL 34229

Last Sold Summary
- 5% Above List Price
- $266/SF
- 197 Days On Market
Last Sold Price $525,000

Last Listing Agent Noah Ward EXP REALTY LLC

/99
$699,000
- 3 Beds
- 3 Baths
- 2,203 Sq Ft
401 N Point Rd Unit 603, Osprey, FL 34229

One or more photo(s) has been virtually staged. This incredible offering has everything you need to live a luxury condominium lifestyle in comfort and ease; 3 bedrooms, 3 full baths, a formal dining room and a 2ND FLOOR PRIVATE 2 CAR GARAGE! Add to this, gorgeous views from almost every room, and you have found a well-priced gem in Meridian at The Oaks Preserve to enjoy all the Gulf Coast has to

Steve Abbe COLDWELL BANKER REALTY

401 N Point Rd Unit 603, Osprey, FL 34229
/2
$765,000 Sold Jan 30, 2026

385 N Point Rd Unit 404, Osprey, FL 34229
- 3 Beds
- 3 Baths
- 2,778 Sq Ft
- Built 2000
Last Sold Summary
- 17% Below List Price
- $275/SF
- 142 Days On Market
Current Estimated Value $846,065

Last Listing Agent Mark Lyda GENEROUS PROPERTY

385 N Point Rd Unit 404, Osprey, FL 34229

/48
Est $355,978 Not Listed For Sale

123 Revolution Way Unit 101, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Built 2016
123 Revolution Way Unit 101, Osprey, FL 34229

Last Sold Summary
- 15% Below List Price
- $267/SF
- 4 Days On Market
Last Sold Price $420,000

Last Listing Agent Tim Weller EXIT KING REALTY

/74
$1,749,990 Open Sat 12PM - 3PM
- 4 Beds
- 4 Baths
- 3,286 Sq Ft
140 Sugar Mill Dr, Osprey, FL 34229

FRESH STYLE....FRESH PRICE! Behind the gates of The Oaks - Bayside, this beautifully redesigned estate presents a rare opportunity to enjoy refined country club living at a compelling new value. Updated and thoughtfully improved with designer transitional style - 140 Sugar Mill Drive offers ultimate privacy with lush landscaping, elegant interiors and resort living. Thoughtfully created for

Monica Verinder COLDWELL BANKER REALTY

140 Sugar Mill Dr, Osprey, FL 34229
/2
$175,000 Sold Feb 23, 2026

216 Glenwood Ave, Osprey, FL 34229
- 2 Beds
- 1 Bath
- 732 Sq Ft
- Built 1989
Last Sold Summary
- 30% Below List Price
- $239/SF
- 64 Days On Market
Current Estimated Value $245,709

Last Listing Agent Kristen Wheat COMPASS FLORIDA LLC

216 Glenwood Ave, Osprey, FL 34229

/61
Est $359,514 Not Listed For Sale

4185 Frontier Ln Unit 102, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Built 2018
4185 Frontier Ln Unit 102, Osprey, FL 34229

Last Sold Summary
- 14% Below List Price
- $267/SF
- 15 Days On Market
Last Sold Price $420,000

Last Listing Agent Tim Weller EXIT KING REALTY

/2
$617,999 New Construction
- 3 Beds
- 2 Baths
- 1,356 Sq Ft
791 S Tamiami Trail Unit 101, Osprey, FL 34229

Under Construction. UNDER CONSTRUCTION -STARTING FROM THE MID $500,000'S. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOW AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 3 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (2 BEDROOM AND 2 BATH UNITS ALSO

Laurie Eshleman PRO GROUP REALTY & PROP MGT

791 S Tamiami Trail Unit 101, Osprey, FL 34229
/2
$760,000 Sold Jul 16, 2025

790 Shadow Bay Way, Osprey, FL 34229
- 4 Beds
- 3 Baths
- 3,091 Sq Ft
- Built 2002
Last Sold Summary
- 9% Below List Price
- $246/SF
- 158 Days On Market
Current Estimated Value $760,146

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

790 Shadow Bay Way, Osprey, FL 34229

/59
Est $354,514 Not Listed For Sale

99 Explorer Dr Unit 102, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Built 2015
99 Explorer Dr Unit 102, Osprey, FL 34229

Last Sold Summary
- 19% Below List Price
- $276/SF
- 37 Days On Market
Last Sold Price $435,000

Last Listing Agent Tim Weller EXIT KING REALTY

/62
$660,000
- 3 Beds
- 3 Baths
- 2,055 Sq Ft
385 N Point Rd Unit 402, Osprey, FL 34229

**BEAUTIFULLY UPDATED CONDO with MARVELOUS VIEW** features 3-BEDS and 3-FULL BATH, 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 Impressively Renovated interior which boasts Engineered Hardwood and designer Wood Plank Tile flooring, Plantation

Mark Lyda GENEROUS PROPERTY

385 N Point Rd Unit 402, Osprey, FL 34229
/2
$227,000 Sold Dec 15, 2025

111 Woodland Place, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
- Built 1979
Last Sold Summary
- 7% Below List Price
- $172/SF
- 81 Days On Market
Current Estimated Value $228,286

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

111 Woodland Place, Osprey, FL 34229

/42
Not Listed For Sale

36 Siesta Cir W, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 673 Sq Ft
- Built 1971
36 Siesta Cir W, Osprey, FL 34229

Last Sold Summary
- $202/SF
- 43 Days On Market
Last Sold Price $136,000

Last Listing Agent Tammie Pickard KW COASTAL LIVING III

/91
$2,195,000
- 3 Beds
- 3 Baths
- 3,681 Sq Ft
600 Eagle Watch Ln, Osprey, FL 34229

One or more photo(s) has been virtually staged. **BRILLIANTLY UPDATED, MOVE-IN READY, GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** offers an Ideal Southern-Exposure and View across the 3rd Fairway of the Interior, HERON GOLF COURSE. Situated on an Oversized 0.71 Acre Lot with Circular Driveway and manicured landscape, this Extensively Renovated Home offers 3

Mark Lyda GENEROUS PROPERTY

600 Eagle Watch Ln, Osprey, FL 34229
/2
$835,000 Sold May 21, 2025

14021 Bellagio Way Unit 410, Osprey, FL 34229
- 3 Beds
- 3.5 Baths
- 2,214 Sq Ft
- Built 2006
Last Sold Summary
- 12% Below List Price
- $377/SF
- 42 Days On Market
Current Estimated Value $787,910

Last Listing Agent Adam Waxler UKEEPCOMMISSION REAL ESTATE

14021 Bellagio Way Unit 410, Osprey, FL 34229

/4
Est $29,262 Not Listed For Sale

570 Blackburn Point Rd Unit 28, Osprey, FL 34229
- Studio
- 45,244 Sq Ft
570 Blackburn Point Rd Unit 28, Osprey, FL 34229

Last Sold Summary
- 11% Below List Price
- $1/SF
- 26 Days On Market
Last Sold Price $33,000

Last Listing Agent Moe Mossa SAVVY AVENUE, LLC

/65
$679,000
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
250 Hidden Bay Dr Unit A302, Osprey, FL 34229

ANOTHER PRICE IMPROVEMENT!!!!WHAT A VIEW and the pictures don't do it justice!! SELLER IS OFFERING to prepay three (3) months of HOA dues on behalf of the buyer at closing. FULLY FURNISHED/TURNKEY UNIT! (optional of course) Prepare to be captivated by jaw-dropping sunsets from your oversized, private, screened-in balcony, offering unobstructed vistas across Little Sarasota Bay to the peaceful

Merryl Koven COLDWELL BANKER REALTY

250 Hidden Bay Dr Unit A302, Osprey, FL 34229
/2
$747,850 Sold Aug 08, 2025

424 Cezanne Dr, Osprey, FL 34229
- 4 Beds
- 4 Baths
- 2,945 Sq Ft
- Built 1975
Last Sold Summary
- 16% Below List Price
- $254/SF
- 128 Days On Market
Current Estimated Value $739,797

Last Listing Agent Christine Pope MICHAEL SAUNDERS & COMPANY

424 Cezanne Dr, Osprey, FL 34229

/24
Not Listed For Sale

338 Tropic Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,055 Sq Ft
- Built 1979
338 Tropic Dr, Osprey, FL 34229

Last Sold Summary
- $136/SF
- 118 Days On Market
Last Sold Price $144,000

Last Listing Agent Kristina Avens COLDWELL BANKER REALTY

/52
$675,000
- 2 Beds
- 2 Baths
- 1,943 Sq Ft
232 Hidden Bay Dr Unit 303, Osprey, FL 34229

Waterfront resort-style living is behind the gates of Hidden Bay, set along the shores of the Intracoastal Waterway, Little Sarasota Bay, and a tranquil preserve and park in the heart of Osprey. This third-floor residence, accessible by elevator, has been tastefully remodeled and offers two full bedrooms, each with en-suite baths. The lanai’s exterior sliders open to an all-season, tiled living

Tom Hedge, Jr PREMIER SOTHEBY'S INTERNATIONAL REALTY

232 Hidden Bay Dr Unit 303, Osprey, FL 34229
/2
$2,300,000 Sold Nov 05, 2025

264 Saratoga Ct, Osprey, FL 34229
- 4 Beds
- 3.5 Baths
- 3,857 Sq Ft
- Built 1992
Last Sold Summary
- $596/SF
- 9 Days On Market
Current Estimated Value $2,204,778

Last Listing Agent Mark Lyda GENEROUS PROPERTY

264 Saratoga Ct, Osprey, FL 34229

/79
Est $617,887 Not Listed For Sale

250 Hidden Bay Dr Unit A203, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
- Built 2017
250 Hidden Bay Dr Unit A203, Osprey, FL 34229

Last Sold Summary
- 8% Below List Price
- $348/SF
- 236 Days On Market
Last Sold Price $675,000

Last Listing Agent Pan Steele, GRI COLDWELL BANKER REALTY

/97
$690,000
- 3 Beds
- 3 Baths
- 2,203 Sq Ft
385 N Point Rd Unit 503, Osprey, FL 34229

TURN-KEY FURNISHED 5TH FLOOR RESIDENCE WITH LOVELY VIEWS! Experience luxury coastal living in this stunning 5th floor condo in Meridian at The Oaks Preserve. With water and Preserve views that rival those of higher floors, this residence offers 3 bedrooms, 3 full baths, and a dining room, all enhanced with NEW FURNISHINGS. OFFERED TURNKEY, ALL YOU NEED TO DO IS MOVE IN AND START ENJOYING A

Steve Abbe COLDWELL BANKER REALTY

385 N Point Rd Unit 503, Osprey, FL 34229
/2
$358,000 Sold Nov 13, 2025

115 Green St, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,503 Sq Ft
- Built 1990
Last Sold Summary
- 4% Above List Price
- $238/SF
- 5 Days On Market
Current Estimated Value $348,186

Last Listing Agent Robin Leonardi MICHAEL SAUNDERS & COMPANY

115 Green St, Osprey, FL 34229

Showing Results 121 - 160, Page 4 of 18

Florida Sarasota County Osprey

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