Osprey, FL Homes

/62
$1,595,000
- 3 Beds
- 3.5 Baths
- 4,241 Sq Ft
909 MacEwen Dr, Osprey, FL 34229

**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious

Mark Lyda GENEROUS PROPERTY

909 MacEwen Dr, Osprey, FL 34229
/41
$2,400 Per Month
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
- Condo for Rent
4219 Frontier Ln Unit 105, Osprey, FL 34229

2 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

4219 Frontier Ln Unit 105, 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 $933,737

Last Listing Agent Marco Guadagnini PREFERRED SHORE LLC

336 Pine Ranch Rd E, Osprey, FL 34229

/34
Not Listed For Sale

201 Palm Air Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Built 1980
201 Palm Air Dr, Osprey, FL 34229

Last Sold Summary
- $162/SF
- 119 Days On Market
- Last Sold Price $155,000
- May 02, 2024
Last Listing Agent Roxane Solowey BERKSHIRE HATHAWAY HOMESERVICE

/69
$1,995,000
- 3 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
/32
$3,595 Per Month
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
- Condo for Rent
280 Hidden Bay Dr Unit 202, Osprey, FL 34229

Be 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

280 Hidden Bay Dr Unit 202, 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 $414,120

Last Listing Agent Bill Garrison RE/MAX PALM

117 Villa Dr Unit 117, Osprey, FL 34229

/46
Est $591,722 Not Listed For Sale

2007 Cordes St, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
- Built 2023
2007 Cordes St, Osprey, FL 34229

Last Sold Summary
- 7% Above List Price
- $276/SF
- 15 Days On Market
- Last Sold Price $554,000
- Nov 30, 2023
Last Listing Agent Lee Brewer RE/MAX

/71
$735,000
- 2 Beds
- 2 Baths
- 2,143 Sq Ft
5100 Jessie Harbor Dr Unit 304, Osprey, FL 34229

Experience effortless coastal living in this stunning third-floor FURNISHED waterfront residence, perfectly positioned for boaters and kayakers in protected waters just off Blackburn Bay and minutes from the Intracoastal Waterway and Gulf. Watch dolphins, manatees, otters, and breathtaking sunsets from your private balcony. Your water views continue inside, flowing through the living room, dining

Suki Scollo COLDWELL BANKER REALTY

5100 Jessie Harbor Dr Unit 304, Osprey, FL 34229
/31
$4,500 Per Month
- 3 Beds
- 2 Baths
- 2,367 Sq Ft
- House for Rent
1355 Southbay Dr, Osprey, FL 34229

Southbay 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

1355 Southbay Dr, 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 $690,339

Last Listing Agent Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

162 Willow Bend Way, Osprey, FL 34229

/2
Est $762,143 Not Listed For Sale

280 Hidden Bay Dr Unit 303, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
- Built 2025
280 Hidden Bay Dr Unit 303, Osprey, FL 34229

Last Sold Summary
- 8% Below List Price
- $430/SF
- 27 Days On Market
- Last Sold Price $832,750
- Apr 10, 2025
Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

/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
/35
$3,795 Per Month
- 3 Beds
- 2 Baths
- 1,937 Sq Ft
- Condo for Rent
280 Hidden Bay Dr Unit 203, Osprey, FL 34229

This second-story unit in Edgewater at Hidden Bay is ready for move-in and is offered furnished or unfurnished. The apartment includes 3 bedrooms, 2 bathrooms, modern finishes, and steady natural light throughout. The kitchen provides ample cabinet storage, a breakfast bar, quartz countertops, and all major appliances, including a stainless-steel refrigerator, microwave, dishwasher, and range.

Nancy Guerrero PMI SOUTHWEST FLORIDA

280 Hidden Bay Dr Unit 203, 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 $530,658

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1313 Thornapple Dr, Osprey, FL 34229

/5
Not Listed For Sale

0 N Point Rd Unit A11454780, Osprey, FL 34229
0 N Point Rd Unit A11454780, Osprey, FL 34229

Last Sold Summary
- 218 Days On Market
- Last Sold Price $850,000
- Apr 24, 2024
Last Listing Agent Jennifer Arciniegas Cuadra Group LLC

/55
$2,249,000
- 4 Beds
- 3.5 Baths
- 4,117 Sq Ft
362 MacEwen Dr, Osprey, FL 34229

Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with

Steve Abbe COLDWELL BANKER REALTY

362 MacEwen Dr, Osprey, FL 34229
/44
$6,500 Per Month
- 3 Beds
- 3 Baths
- 2,266 Sq Ft
- House for Rent
521 Habitat Blvd, Osprey, FL 34229

Stylish 3BR Pool Home w/ Office – 10 Mins to Beach ****SEASONAL RENTAL ONLY**** 90 Day minimum stay, Peak Season at $8,900/mo plus fees; Off Season at $6,500/mo plus fees. NOTE: Jan, Feb and March 2027 are Not Available. Your Gulf Coast getaway awaits at this beautifully furnished 3-bedroom, 3-bath pool home in the scenic Willowbend community of Osprey, FL. Ideal for mid-term stays, this spacious

Dave Holt PMI SOUTHWEST FLORIDA

521 Habitat Blvd, 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 $776,645

Last Listing Agent Mark Lyda GENEROUS PROPERTY

385 N Point Rd Unit 404, Osprey, FL 34229

/24
Est $290,387 Not Listed For Sale

4224 Expedition Way Unit 105, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
- Built 2016
4224 Expedition Way Unit 105, Osprey, FL 34229

Last Sold Summary
- 17% Below List Price
- $308/SF
- 0 Days On Market
- Last Sold Price $350,000
- Sep 12, 2023
Last Listing Agent Randal Longo KEYS REALTY REDEFINED LLC

/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
/53
$5,000 Per Month
- 2 Beds
- 2.5 Baths
- 1,950 Sq Ft
- Condo for Rent
260 Hidden Bay Dr Unit B-504, Osprey, FL 34229

Annual Turnkey Furnished or short term seasonal Penthouse on the Bay! If you want mesmerizing views of intracoastal waterway, Little Sarasota Bay, Casey Key, and the Gulf of Mexico in a beautiful, comfortable and roomy penthouse, then this could be your next home. This natural light filled delight is 2 bedrooms, each with en suite bathroom, separate office with large closet and glass French

Cody Smith RENT SARASOTA

260 Hidden Bay Dr Unit B-504, 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 $209,338

Last Listing Agent Kristen Wheat COMPASS FLORIDA LLC

216 Glenwood Ave, Osprey, FL 34229

/4
Est $53,749 Not Listed For Sale

570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229
- Studio
- 45,244 Sq Ft
570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229

Last Sold Summary
- 10% Below List Price
- $1/SF
- 21 Days On Market
- Last Sold Price $60,000
- Aug 29, 2023
Last Listing Agent Christopher Pelletier CHRISTOPHER PELLETIER BROKER

/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
/87
$6,950 Per Month
- 3 Beds
- 2 Baths
- 2,143 Sq Ft
- Condo for Rent
5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229

CLOSE TO NOKOMIS BEACH! BOOKED JAN/FEB/MAR 2027. AVAILABLE APR 2027 $6,950/MONTH. Beautiful direct waterfront 5th Floor condo located in Blackburn Harbor Residences with breathtaking panoramic water views of Little Sarasota Bay, which can be seen from the living room, kitchen, primary bedroom suite, and spacious balcony! The condo comes turnkey furnished and has 3 bedrooms (3rd bedroom was

Chrissie Cummings JENNETTE PROPERTIES INC

5100 Jessie Harbor Dr Unit 504, 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 $776,902

Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

790 Shadow Bay Way, Osprey, FL 34229

/12
Est $24,323 Not Listed For Sale

570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229
- Studio
- 45,244 Sq Ft
570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229

Last Sold Summary
- 10% Below List Price
- $1/SF
- 69 Days On Market
- Last Sold Price $27,000
- Sep 29, 2023
Last Listing Agent Stephen Mason PREFERRED SHORE LLC

/97
$1,399,000
- 3 Beds
- 3 Baths
- 2,594 Sq Ft
385 N Point Rd Unit 701, Osprey, FL 34229

Situated on the 7th floor of The Meridian, this sophisticated three-bedroom plus den, three-bath residence with private two-car garage offers elevated waterfront living behind the gates of the prestigious The Oaks Preserve and within the exclusive Oaks Club community. Every detail has been carefully curated for refined comfort, luxury, and effortless Florida indoor-outdoor living. A private

Judy Wright, PA MICHAEL SAUNDERS & COMPANY

385 N Point Rd Unit 701, 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 $225,141

Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

111 Woodland Place, Osprey, FL 34229

/50
Est $563,041 Not Listed For Sale

2006 Preymore St, Osprey, FL 34229
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
- Built 2023
2006 Preymore St, Osprey, FL 34229

Last Sold Summary
- 5% Above List Price
- $267/SF
- 10 Days On Market
- Last Sold Price $535,000
- Apr 08, 2024
Last Listing Agent Lee Brewer RE/MAX

/55
$1,465,000 Pending
- 3 Beds
- 3 Baths
- 2,414 Sq Ft
434 E MacEwen Dr, Osprey, FL 34229

Meticulously maintained and updated with care, this 3 bedroom, 3 bath + den/study home in The Oaks Clubside offers beautiful views. A mixture between clean modern lines and cottage chic this house feels cozy. Yet it has an open floor plan, soaring ceilings and every room in the house is light and bright. The formal living room opens to the large lanai and pool with Southern exposure. The view

Steve Abbe COLDWELL BANKER REALTY

434 E MacEwen Dr, 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 $790,945

Last Listing Agent Adam Waxler UKEEPCOMMISSION REAL ESTATE

14021 Bellagio Way Unit 410, Osprey, FL 34229

/2
Est $287,702 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
- 9% Below List Price
- $255/SF
- 5 Days On Market
- Last Sold Price $317,500
- Feb 07, 2025
Last Listing Agent Tim Weller EXIT KING REALTY

/74
$1,399,000 Pending
- 4 Beds
- 4 Baths
- 3,286 Sq Ft
140 Sugar Mill Dr, Osprey, FL 34229

Under contract-accepting backup offers. SELLERS SAY SELL! BEST PRICED 4 BED IN THE OAKS - MAJOR UPDATES ALLOW IMMEDIATE MOVE IN - NO REMODELING NEEDED! 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

Monica Verinder COLDWELL BANKER REALTY

140 Sugar Mill Dr, Osprey, FL 34229
/2
$137,000 Sold Apr 17, 2026

214 Palm Air Dr, Osprey, FL 34229
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Built 1979
Last Sold Summary
- 2% Below List Price
- $143/SF
- 1 Day On Market
Last Listing Agent Garrett Sedlacek KELLER WILLIAMS ON THE WATER S

214 Palm Air Dr, Osprey, FL 34229

/17
Est $291,182 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
- Sep 12, 2023
Last Listing Agent Uli Wills WILLS REAL ESTATE LLC

/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
$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 $768,789

Last Listing Agent Christine Pope MICHAEL SAUNDERS & COMPANY

424 Cezanne Dr, 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
- Jun 20, 2024
Last Listing Agent Christy Neff Michael Saunders

Showing Results 121 - 160, Page 4 of 18

Florida Sarasota County Osprey

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