Osprey, FL Homes

/44
Est $1,059,916 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,534 Sq Ft
315 Sea Anchor Dr, Osprey, FL 34229

315 Sea Anchor Dr, Osprey, FL 34229

/48
$335,000
- 3 Beds
- 2 Baths
- 1,889 Sq Ft
4256 Expedition Way Unit 107, Osprey, FL 34229

Welcome to Bay Street. Step into the Florida lifestyle you've been dreaming of with this beautifully designed second-floor condo featuring 3 bedrooms and 2 full baths at 4256 Exhibition Way #107, Osprey, FL. Built just eight years ago, this home blends modern comfort with timeless appeal, offering a setting that feels both inviting and refined. From the moment you walk in, your eyes are drawn to

Geri Scheckner Bright Realty

4256 Expedition Way Unit 107, Osprey, FL 34229
/2
$318,000 Sold Apr 30, 2025
- 1,411 Sq Ft
- $225/SF
- 125 Days On Market
- 2 Beds
- 2 Baths
- Built 1972
115 Villa Dr Unit 115, Osprey, FL 34229

Welcome to your future waterfront retreat in the heart of Osprey, where coastal living meets convenience. This beautifully appointed villa offers 1,411 square feet of thoughtfully designed living space, featuring two bedrooms and two bathrooms in a flowing, open-concept layout.The primary bedroom suite provides a peaceful sanctuary with an ensuite bathroom and generous closet space.

EJ Stukenborg KELLER WILLIAMS ON THE WATER S

115 Villa Dr Unit 115, Osprey, FL 34229

/46
Est $1,596,328 Not Listed For Sale
- 3 Beds
- 3 Baths
- 3,740 Sq Ft
345 S Shore Dr, Osprey, FL 34229

345 S Shore Dr, Osprey, FL 34229

/32
$3,360,000
- 3 Beds
- 4.5 Baths
- 2,572 Sq Ft
135 Tina Island Dr, Osprey, FL 34229

Retreat to paradise in this stunning waterfront home, built new in 2011, in highly sought-after Sorrento Shores, Osprey. Perfectly situated on 210 feet of wide canal frontage, this residence offers deep water access with no bridges to the bay—a dream for boaters. Nearly every room provides breathtaking views of the water and swaying palms. Constructed with concrete block on both floors and

Cliff Glansen FLATFEE.COM

135 Tina Island Dr, Osprey, FL 34229
/2
$950,000 Sold Apr 29, 2025
- 2,570 Sq Ft
- $370/SF
- 82 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1993
32 Bayhead Ln, Osprey, FL 34229

Divine is in the details of this lovely 3 bedroom, 3 1⁄2 bath professionally redesigned home in the Oaks Preserve. No need to be concerned with remodeling, as this home underwent a complete renovation in 2023. This exceptional property meets the demands of today’s discriminating buyer, with a spacious chef’s gourmet kitchen featuring top of the line stainless appliances, a large prep island,

Rosalie Phillips MICHAEL SAUNDERS & COMPANY

32 Bayhead Ln, Osprey, FL 34229

/32
Est $296,678 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,397 Sq Ft
112 Villa Dr, Osprey, FL 34229

112 Villa Dr, Osprey, FL 34229

/92
$925,000
- 3 Beds
- 2 Baths
- 2,216 Sq Ft
21 Bayhead Ln, Osprey, FL 34229

Looking for a home you can fall in love with? The search is over! Once you see this thoughtfully updated, impeccably maintained 3 bedroom, 2 bath home in The Oaks Preserve you will know you have found your home-sweet-home. From the moment you pull up to the pavered driveway, the care taken to maintain this property is evident. Walk past the two-car garage to the pretty, double front doors with

Steve Abbe COLDWELL BANKER REALTY

21 Bayhead Ln, Osprey, FL 34229
/2
$165,000 Sold Apr 28, 2025
- 1,223 Sq Ft
- $135/SF
- 53 Days On Market
- 2 Beds
- 2 Baths
- Built 1980
235 Woodland Dr Unit 235, Osprey, FL 34229

Welcome to 235 Woodland Drive in sunny Osprey, FL—located between Sarasota and Venice so you can easily enjoy the beaches, shopping, arts and entertainment of both towns. This 1,223 square-foot home is all about easy living, featuring an open floor plan and soaring ceilings that let in tons of natural light. You’ll love the sun-drenched living and dining areas, with huge sliding doors that open

Priscilla Adams COMPASS FLORIDA LLC

235 Woodland Dr Unit 235, Osprey, FL 34229

/2
Est $722,426 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,388 Sq Ft
668 Clear Creek Dr, Osprey, FL 34229

668 Clear Creek Dr, Osprey, FL 34229

/100
$1,750,000
- 3 Beds
- 3.5 Baths
- 3,872 Sq Ft
422 Blue Garden Ln, Osprey, FL 34229

A grand traditional residence, this 3-bedroom, 3.5-bath home is tucked into lush tropical landscaping on a quiet cul-de-sac in The Oaks Bayside. Double entry doors open to a marble foyer and wood floors that set the tone for quality throughout. Just off the entry, a cozy den with fireplace sits opposite a spacious guest suite. The heart of the home is the light-filled great room, with formal

Steve Abbe COLDWELL BANKER REALTY

422 Blue Garden Ln, Osprey, FL 34229
/2
$179,000 Sold Apr 28, 2025
- 1,119 Sq Ft
- $160/SF
- 57 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
312 Tropic Dr, Osprey, FL 34229

Welcome to your dream home in a vibrant 55+ community! This charming residence offers 2 spacious bedrooms and 2 full bathrooms, perfect for comfortable living. Enjoy the Florida lifestyle with two screened-in porches, ideal for relaxing or entertaining. The home features a convenient laundry room and ample storage space. Equipped with hurricane windows, this home provides peace of mind. The roof

Michelle Ward COMPASS FLORIDA LLC

312 Tropic Dr, Osprey, FL 34229

/100
Est $1,111,613 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,215 Sq Ft
328 Pine Ranch Trail, Osprey, FL 34229

328 Pine Ranch Trail, Osprey, FL 34229

/50
$659,000
- 3 Beds
- 3 Baths
- 2,320 Sq Ft
522 Luminary Blvd, Osprey, FL 34229

This highly sought-after Ashley II model is situated with rear yard southern exposure on the community lake within the beautiful Willowbend neighborhood. The residence encompasses 2,320 square feet of open living space, including three bedrooms, three bathrooms, formal living and dining rooms, and an additional office or den. The kitchen is equipped with a full island, generous cabinetry,

Ray Nesci REALTY MARK ASSOCIATES

522 Luminary Blvd, Osprey, FL 34229
/2
$744,800 Sold Apr 24, 2025
- 3,060 Sq Ft
- $243/SF
- 145 Days On Market
- 4 Beds
- 3 Baths
- Built 2002
448 Park Trace Blvd, Osprey, FL 34229

**MOTIVATED SELLERS – WILL OFFER CREDIT TOWARD A NEW ROOF WITH ACCEPTABLE OFFER!** Experience the ideal combination of elegance, comfort, and functionality in this custom-built pool home, thoughtfully crafted with premium upgrades and meticulously maintained over the years. Set on a spacious lot, this home boasts 4 bedrooms, 3 baths, a dedicated office, and an impressive array of features

Toni Zarghami KW COASTAL LIVING III

448 Park Trace Blvd, Osprey, FL 34229

/54
Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 5,168 Sq Ft
871 MacEwen Dr, Osprey, FL 34229

871 MacEwen Dr, Osprey, FL 34229

/76
$465,000
- 2 Beds
- 2 Baths
- 1,604 Sq Ft
508 Meadow Sweet Cir, Osprey, FL 34229

PRICE IMPROVEMENT!! The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home is surrounded by lush landscaping and tree-lined streets, contributing to the area's charm and appeal. This home features 2 bedrooms and 2 bathrooms, as well as a versatile den or office space. It is an ideal choice for those seeking a seasonal residence in

Bill Cantrell FLORIDA HOME TEAM LLC

508 Meadow Sweet Cir, Osprey, FL 34229
/2
$315,000 Sold Apr 24, 2025
- 1,092 Sq Ft
- $288/SF
- 147 Days On Market
- 3 Beds
- 2 Baths
- Built 2004
214 Patterson Ave, Osprey, FL 34229

Welcome to your dream home in the enchanting village of Osprey! This inviting 3-bedroom, 2-bathroom block home is nestled on a tranquil street, surrounded by lush landscaped gardens. Designed with comfort and functionality in mind, the open-plan living and dining area provides an ideal space for gatherings, with a clear view into the fully remodeled kitchen. Whether cooking or entertaining, the

Lisa Bouck, PA RE/MAX ALLIANCE GROUP

214 Patterson Ave, Osprey, FL 34229

/65
Est $1,932,929 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,327 Sq Ft
482 E MacEwen Dr, Osprey, FL 34229

482 E MacEwen Dr, Osprey, FL 34229

/100
$1,385,000
- 3 Beds
- 3.5 Baths
- 3,112 Sq Ft
156 Bishopscourt Rd, Osprey, FL 34229

This stunning 3 bedroom, 3.5 bath home, designed by the renowned architect Frank Folsom Smith, stands out with its unique design. The charming Cape Cod style sets the stage for comfortable, graceful living. The home, with beautiful wood floor throughout the main living areas, features a Sonos stereo sound system. The backyard, overlooking the preserve, and offering a lovely sunset exposure, is a

Steve Abbe COLDWELL BANKER REALTY

156 Bishopscourt Rd, Osprey, FL 34229
/2
$880,000 Sold Apr 23, 2025
- 2,045 Sq Ft
- $430/SF
- 61 Days On Market
- 3 Beds
- 2 Baths
- Built 1978
1237 Flying Bridge Ln, Osprey, FL 34229

A Southbay Yacht & Racquet Club beauty! This home has been given meticulous care and offers an abundance of updates and upgrades. Popular Southbay community features a boating marina on the Inter coastal Waterway, making this one of the most sought after locations west of the trail! This airy and open floorplan is sure to please! There are so many delightful updates and improvements, I'll try to

Pat Williams PAT WILLIAMS REALTY, LLC

1237 Flying Bridge Ln, Osprey, FL 34229

/64
Est $295,285 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,839 Sq Ft
112 Woodland Place, Osprey, FL 34229

112 Woodland Place, Osprey, FL 34229

/94
$245,000
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
111 Woodland Place, Osprey, FL 34229

Hidden away in Osprey is the private oasis of Pine Run. You could not find a more natural setting and fantastic location, convenient to Sarasota, Venice and Gulf beaches. This immaculate, ground floor condo is being sold furnished so settling in will be easy. The updated kitchen with stainless appliances is large enough to incorporate dine-in eating, and a laundry closet with full size washer and

Priscilla Adams COMPASS FLORIDA LLC

111 Woodland Place, Osprey, FL 34229
/2
$807,000 Sold Apr 22, 2025
- 2,112 Sq Ft
- $382/SF
- 244 Days On Market
- 3 Beds
- 2 Baths
- Built 1975
124 Tina Island Dr, Osprey, FL 34229

***Amazing waterfront opportunity*** One of the lowest priced canal front properties between Sarasota and Venice*** This great waterfront location is in desirable Sorrento Shores with a new dock on a wide canal sitting on a large lot with great views This 3 bedroom 2 bath split plan has a large living/dining area and a separate office space. The kitchen area has a separate seating area with a

Glenn Davis COLDWELL BANKER SARASOTA CENT.

124 Tina Island Dr, Osprey, FL 34229

/2
Est $385,399 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,304 Sq Ft
308 Kensey Ln, Osprey, FL 34229

308 Kensey Ln, Osprey, FL 34229

/44
$289,000
- 2 Beds
- 2 Baths
- 1,379 Sq Ft
707 Pine Run Dr, Osprey, FL 34229

Nestled in a nature enthusiast’s haven is an architecturally stunning community. Located halfway between the cultural, shopping & culinary meccas of Sarasota & Venice you find the uniquely contemporary community of Pine Run. The community offers Tennis & Pickleball courts, Fitness center, two heated pools, Saunas and an exquisite club house. This ground floor unit offers dual zone A/C, in unit

James Rightmyer RESULTS REALTY GROUP LLC

707 Pine Run Dr, Osprey, FL 34229
/2
$245,000 Sold Apr 21, 2025
- 1,316 Sq Ft
- $186/SF
- 103 Days On Market
- 2 Beds
- 2 Baths
- Built 1980
225 Woodland Dr, Osprey, FL 34229

This completely remodeled, GROUND LEVEL, 2/2 condo is available in a charming West of Trail community (but not in a flood zone) and is the hidden gem you've been looking for! Step inside and be captivated by artistic elegance. This home has been thoughtfully updated and features a new HVAC system in 2023, a kitchen remodel in 2023 including sleek new appliances (including an induction cooktop),

Priscilla Adams COMPASS FLORIDA LLC

225 Woodland Dr, Osprey, FL 34229

/30
Est $133,926 Not Listed For Sale
- 1 Bed
- 1 Bath
- 586 Sq Ft
751 Pine Run Dr Unit 751, Osprey, FL 34229

751 Pine Run Dr Unit 751, Osprey, FL 34229

/33
$177,000
- 1 Bed
- 1 Bath
- 886 Sq Ft
310 Pine Run Dr, Osprey, FL 34229

SELLER OFFERING 1 YEAR HOME WARRANTY! Seller did $20,000 of upgrades. Welcome to 310 Pine Run Dr a charming and thoughtfully designed 1-bedroom, 1-bath condominium with an additional open loft space, nestled in the serene, amenity-rich Pine Run community. This unit blends comfort and functionality with a bright, open layout, perfect for seasonal or year-round living. Have peace of mind with 2022

Krystina Londeree COMPASS FLORIDA LLC

310 Pine Run Dr, Osprey, FL 34229
/2
$600,000 Sold Apr 18, 2025
- 2,887 Sq Ft
- $208/SF
- 24 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1995
402 Pine Ranch Rd E, Osprey, FL 34229

LLocated 1-2 mile from the legacy trail off Bay St. in Osprey. Built on one acre in 1995. This is a 3-bedroom 3.5 bath home that has a lot of potential. The large office in the front of the home could be made into a 4th bedroom. The family room has a fireplace, built-in shelving and has a view of the pool. The pool bath is behind the family room with direct access to the pool. The master suite

Ronnie Caron CARON REALTY INC

402 Pine Ranch Rd E, Osprey, FL 34229

/50
Est $525,100 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,789 Sq Ft
529 Meadow Sweet Cir, Osprey, FL 34229

529 Meadow Sweet Cir, Osprey, FL 34229

/4
$1,500
- 1 Bed
- 1 Bath
124 Happy Haven Dr Unit 10, Osprey, FL 34229

Calling all Investors! Huge opportunity to make a deal on this perfect renovation project. Quick Closing, Quick Renovation and Quick Profit! This home needs significant work and is priced accordingly. Given the amount of work necessary to bring this gem up to it's fiull potential, prospective investors must be licensed and experienced renovation specialists. Call today, we are currently

Tori Coil Happy Haven

124 Happy Haven Dr Unit 10, Osprey, FL 34229
/2
$650,000 Sold Apr 18, 2025
- 2,431 Sq Ft
- $267/SF
- 113 Days On Market
- 3 Beds
- 2 Baths
- Built 1995
610 Pine Ranch Rd E, Osprey, FL 34229

Price Reduced on this Magnificent three bedroom, two bath home with den, heated pool, fenced yard for privacy in Bay Oaks Estates in Osprey. This fantastic, well maintained home has it all including a LOW annual fee of $270. Features include an updated kitchen with large farmer sink, quartz counters, Bosch Range with stainless hood, Bosch dishwasher, Samsung Refrigerator with plenty of storage,

Kim Klee COLDWELL BANKER REALTY

610 Pine Ranch Rd E, Osprey, FL 34229

/68
Est $872,356 Not Listed For Sale
- 6 Beds
- 3 Baths
- 3,982 Sq Ft
1081 Scherer Way, Osprey, FL 34229

1081 Scherer Way, Osprey, FL 34229

/7
$3,000
- 1 Bed
- 1 Bath
124 Happy Haven Dr Unit 28, Osprey, FL 34229

Calling all Investors! Huge opportunity to make a deal on this perfect renovation project. Quick Closing, Quick Renovation and Quick Profit! This home needs significant work and is priced accordingly. Given the amount of work necessary to bring this gem up to it's fiull potential, prospective investors must be licensed and experienced renovation specialists. Call today, we are currently

Tori Coil Happy Haven

124 Happy Haven Dr Unit 28, Osprey, FL 34229
/2
$1,050,000 Sold Apr 16, 2025
- 2,871 Sq Ft
- $366/SF
- 70 Days On Market
- 3 Beds
- 2 Baths
- Built 1979
247 Keel Way, Osprey, FL 34229

No hurricane problems here! impact windows and storm curtains on the lanai helped to keep this home safe. Also located in an X flood zone! This beautiful home located in "west of the trail", Southbay Yacht and Racquet Club is a very sought after location. One of the few communities with it's own marina and very reasonable dock rental fees only available to homeowners in the community. This home

Pat Williams PAT WILLIAMS REALTY, LLC

247 Keel Way, Osprey, FL 34229

/43
Est $474,821 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,040 Sq Ft
1130 Beachcomber Ct, Osprey, FL 34229

1130 Beachcomber Ct, Osprey, FL 34229

/37
$549,000
- 2 Beds
- 2 Baths
- 1,229 Sq Ft
455 N Shore Dr, Osprey, FL 34229

Live the quintessential Florida lifestyle at 455 N Shore Drive in Osprey! Located West of the Trail in desirable Sorrento Shores, this beautifully updated 2-bedroom, 2-bath home is perfect for entertaining, relaxing, or as a strong rental investment.Just minutes from Nokomis Beach, Venice Beach, and Siesta Key, residents can also join the Sorrento Shores Marina Association, offering 42

Geoff Scalera AUM FLORIDA REAL ESTATE LLC

455 N Shore Dr, Osprey, FL 34229
/2
$385,000 Sold Apr 16, 2025
- 1,346 Sq Ft
- $286/SF
- 244 Days On Market
- 2 Beds
- 2 Baths
- Built 1963
329 Bay Vista Ave, Osprey, FL 34229

One or more photo(s) has been virtually staged. Come see this charming house in Osprey It features 2 bedrooms , 2 baths and a 2 car garage .The main bedroom has a sitting room. The kitchen has been updated with white cabinets with soft close drawers, granite countertops, stainless steel refrigerator and dishwasher. Save on electricity with the fully owned solar panel system. The entire yard is

Colette Jay HORIZON REALTY INTERNATIONAL

329 Bay Vista Ave, Osprey, FL 34229

/37
Est $853,344 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,023 Sq Ft
192 Park Trace Blvd, Osprey, FL 34229

192 Park Trace Blvd, Osprey, FL 34229

Showing Results 281 - 320, Page 8 of 18

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