Osprey, FL Homes

/2
$1,775,000 Sold Oct 22, 2024
- 3,912 Sq Ft
- $454/SF
- 152 Days On Market
- 4 Beds
- 4.5 Baths
- Built 1989
165 Sugar Mill Dr, Osprey, FL 34229

This 4 bedroom, 4.5 bath home in The Oaks Bayside has been continuously updated and redecorated over the past several years, making it a pristine, elegant showcase. This is the perfect home for the refined country club lifestyle you seek to live. As you enter the new paver circular driveway, with three car side entry garage, it is evident how special this house is. Ideally situated on a private

Steve Abbe COLDWELL BANKER REALTY

165 Sugar Mill Dr, Osprey, FL 34229

/40
Est $1,210,972 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,827 Sq Ft
109 Tina Island Dr, Osprey, FL 34229

109 Tina Island Dr, Osprey, FL 34229

/18
$249,900 Pending
- 3 Beds
- 2 Baths
- 1,284 Sq Ft
444 Washington Ave, Osprey, FL 34229

Under contract-accepting backup offers. Handyman or tear down. Potential of 2 buildable lots. The carport area roof lifted in last hurricane.

Hansel Pitts COLDWELL BANKER SARASOTA CENT.

444 Washington Ave, Osprey, FL 34229
/2
$580,000 Sold Oct 17, 2024
- 1,482 Sq Ft
- $391/SF
- 23 Days On Market
- 3 Beds
- 2 Baths
- Built 1989
216 Shoreland Dr, Osprey, FL 34229

Key West Home completely redone in 2023 listed at $30K Under Recent Appraisal! 3 Bedroom /2 Bath plus Office/Den with High End Finishes. The interior and exterior blend seamlessly with a screened lanai across the entire front of the home with French doors into all front facing rooms. It feels as though you’re in a treehouse.Take your Kayaks & Canoes across the street to Shoreland Park

Dennis Schulte MICHAEL SAUNDERS & COMPANY

216 Shoreland Dr, Osprey, FL 34229

/65
Est $948,481 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,632 Sq Ft
800 Eaglenook Way, Osprey, FL 34229

800 Eaglenook Way, Osprey, FL 34229

/40
$4,500,000 Pending
- 3 Beds
- 2 Baths
- 1,876 Sq Ft
426 N Casey Key Rd, Osprey, FL 34229

Under contract-accepting backup offers. Gulf to Bay on North Casey Key – the perfect location! Panoramic views of Little Sarasota Bay to the east and a beachfront lot on the west. Original cypress tongue and groove ceilings and beautiful oak floors add warmth and nostalgia throughout the home. A nicely updated kitchen overlooks the pool and bay. The entire second floor is dedicated to an

Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

426 N Casey Key Rd, Osprey, FL 34229
/2
$335,000 Sold Oct 15, 2024
- 1,515 Sq Ft
- $221/SF
- 2 Days On Market
- 3 Beds
- 2 Baths
- Built 1997
223 Hidden Bay Dr Unit 305, Osprey, FL 34229

Waterfront community, this third-floor unit has elevator access and an oversized two-car garage. Gorgeous panoramic views of a tranquil pond with water features, community pool, clubhouse & pickleball. This is an estate sale, and the family is selling it as-is and priced it to sell. Purchase this condo and remodel it to your very own design. The south side of the unit has impact windows in the

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

223 Hidden Bay Dr Unit 305, Osprey, FL 34229

/9
Est $175,834 Not Listed For Sale
- 2 Beds
- 1 Bath
- 630 Sq Ft
242 Washington Ave, Osprey, FL 34229

242 Washington Ave, Osprey, FL 34229

/6
$39,000 Pending
570 Blackburn Point Rd Unit 17, Osprey, FL 34229

Dry boat slip for sale at Osprey Harbor Village—hurricane-protected dry storage with top-tier amenities! This rarely available top-level slip means no boats dripping on yours and offers hassle-free storage in one of Sarasota County’s most convenient locations. Keep your boat safe from Florida’s unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the

Daniel Treiman MICHAEL SAUNDERS & COMPANY

570 Blackburn Point Rd Unit 17, Osprey, FL 34229
/2
$265,000 Sold Oct 07, 2024
- 595 Sq Ft
- $445/SF
- 0 Days On Market
- 1 Bed
- 1 Bath
- Built 1990
51 MacEwen Dr Unit 13, Osprey, FL 34229

RARE OPPORTUNITY now available at the WINDSOR LODGE, located within The OAKS! This second-floor, maintenance-free studio condominium is the easiest way to become a club member and experience the distinguished lifestyle. Perfect for your quests, vacations, weekend getaways, seasonal home and more! Enjoy the benefits and country club lifestyle of The Oaks Club with the purchase of a Windsor Lodge

Jamie Mullis COLDWELL BANKER REALTY

51 MacEwen Dr Unit 13, Osprey, FL 34229

/38
Est $525,259 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,714 Sq Ft
527 Meadow Sweet Cir, Osprey, FL 34229

527 Meadow Sweet Cir, Osprey, FL 34229

/54
$765,000 Pending
- 3 Beds
- 2 Baths
- 2,463 Sq Ft
127 Park Trace Blvd, Osprey, FL 34229

Absolutely Spectacular Lake-View Home in Osprey - with New ROOF and Upgrades throughout is priced to sell!This property boasts over $160,000 in enhancements, including a custom-designed luxury bath, bespoke mastercloset, renovated kitchen, porcelain flooring, remote-controlled blinds, plantation shutters, upgraded laundryfacilities, built-in outdoor grill, refinished pool w/new

Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

127 Park Trace Blvd, Osprey, FL 34229
/2
$900,000 Sold Oct 04, 2024
- 2,968 Sq Ft
- $303/SF
- 29 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1978
1321 Southbay Dr, Osprey, FL 34229

This is an outstanding Southbay residence, the best-kept secret on the Gulf Coast where boats are accommodated in a deep-water marina for low fees. Numerous recent upgrades and finishes. Inviting paver drive, oversized 22-by-24-foot garage and double-door entry welcomes you to a home that is simultaneously tranquil and energizing. Custom crafted throughout with a wood fireplace that is centered

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

1321 Southbay Dr, Osprey, FL 34229

/32
Est $273,020 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
237 Woodland Dr Unit 237, Osprey, FL 34229

237 Woodland Dr Unit 237, Osprey, FL 34229

/40
$350,000 Pending
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
4236 Expedition Way Unit 106, Osprey, FL 34229

Under contract-accepting backup offers. FABULOUS, MODERN, FURNISHED 3 BEDROOM/2 BATHROOM/1 CAR GARAGE CONDO in desirable Bay Street Village. This second story (walk-up) is impressive! The OPEN CONCEPT offers a spacious feel, yet the split bedroom design allows for privacy when your guests are visiting. Quality features include a designer kitchen with cherry cabinets, crown molding, granite

Susan Honsberger RE/MAX ALLIANCE GROUP

4236 Expedition Way Unit 106, Osprey, FL 34229
/2
$925,000 Sold Sep 30, 2024
- 2,433 Sq Ft
- $380/SF
- 10 Days On Market
- 4 Beds
- 3 Baths
- Built 2003
1030 Scherer Way, Osprey, FL 34229

Welcome Home to this well designed and meticulously cared for home! This 4 Bedroom 3 Bathroom POOL Home with 3 car garage is just what you have been searching for. This Luxurious home is situated on a large beautifully landscaped, lake front lot with a Southeast Exposure overlooking Oscar Scherer State park! Peaceful, relaxing, yet close to shopping, restaurants, Legacy Trail, Osprey Junction,

Kimberly Young BERKSHIRE HATHAWAY HOMESERVICE

1030 Scherer Way, Osprey, FL 34229

/34
Est $616,300 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,163 Sq Ft
1358 Thornapple Dr, Osprey, FL 34229

1358 Thornapple Dr, Osprey, FL 34229

/96
$3,250,000 Pending
- 4 Beds
- 3.5 Baths
- 2,380 Sq Ft
5 N Casey Key Rd, Osprey, FL 34229

Under contract-accepting backup offers. HOME RUN DEAL YOU CAN'T AFFORD TO MISS! CASEY KEY GULF FRONT MOVE-IN READY FOR UNBELIEVABLE PRICE! REDUCED 900K! Iconic Gulf-front Mid-Century Modern gated residence on Casey Key embodies the true essence of casual coastal living, offering an unparalleled retreat for the soul. The moment you step through the door, a magical transformation takes place. Your

Kelley Ann Ayers AYERS AND ASSOCIATES REAL ESTATE

5 N Casey Key Rd, Osprey, FL 34229
/2
$20,000 Sold Sep 30, 2024
- 135 Days On Market
570 Blackburn Point Rd Unit 14-LIDO, Osprey, FL 34229

DRY SLIP BOAT RACK W/ FUELING, MARINA AND RESTAURANT! 32LX8HX10W, slip s14 at Osprey Harbor totally takes the stress and worry out of boating! Simply call ahead to the friendly staff to order your boat to be splashed. Arrive for a fun day on the water and when you return, the staff pulls the boat, washes the exterior, flushes the engine(s), and places it in your own rack for next time. This is an

Bob Stahlschmidt II BRIGHT REALTY

570 Blackburn Point Rd Unit 14-LIDO, Osprey, FL 34229

/42
Est $586,361 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,079 Sq Ft
564 Crane Prairie Way, Osprey, FL 34229

564 Crane Prairie Way, Osprey, FL 34229

/61
$679,000 Pending
- 3 Beds
- 3 Baths
- 2,223 Sq Ft
673 Crane Prairie Way, Osprey, FL 34229

Under contract-accepting backup offers. Enjoy spectacular sunsets over a sweeping lake view the minute you walk through the door. This lovely Savannah model built by Lee Wetherington boasts three spacious bedrooms, three baths plus an office/flex room, making it the property for you and your family and guests. The primary suite has a sitting area that opens to the pool and lanai, two walk-in

Laura Harris, PA PREMIER SOTHEBYS INTL REALTY

673 Crane Prairie Way, Osprey, FL 34229
/2
$1,300,000 Sold Sep 27, 2024
- 2,916 Sq Ft
- $446/SF
- 0 Days On Market
- 3 Beds
- 4 Baths
- Built 1976
322 Yacht Harbor Dr, Osprey, FL 34229

Welcome to BOATERS PARADISE and this stunning OVERSIZED CORNER-LOT pool home with breathtaking WATER VIEWS of the private deep-water marina in the highly sought-after Southbay Yacht & Racquet Club. This expansive residence boasts three bedrooms, a possible FOURTH bedroom (currently used as a den), four bathrooms, and a bonus room, all situated on a corner lot with a circular drive and a

Lori Turkovics COLDWELL BANKER REALTY

322 Yacht Harbor Dr, Osprey, FL 34229

/3
Est $684,122 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,630 Sq Ft
6100 Jessie Harbor Dr Unit 403, Osprey, FL 34229

6100 Jessie Harbor Dr Unit 403, Osprey, FL 34229

/38
$210,000 Pending
- 2 Beds
- 2 Baths
- 1,376 Sq Ft
191 Palm Air Dr, Osprey, FL 34229

Under contract-accepting backup offers. Come home to this tastefully-furnished, well-maintained spacious home in a top-of-the-line, perfectly located Co-Op park. LOTS OF UPGRADES: NEW windows 2022, NEW A/C and HVAC 2023, NEW moisture barrier underneath 2022. NEW hurricaine window covers 2023, NEW Solar tube in kitchen 2022, NEW ceiling fan in dining area 2022. Relax in the 1,376

John Alexander FINE PROPERTIES

191 Palm Air Dr, Osprey, FL 34229
/2
$1,210,000 Sold Sep 23, 2024
- 2,391 Sq Ft
- $506/SF
- 59 Days On Market
- 3 Beds
- 3 Baths
- Built 2016
3933 Waypoint Ave, Osprey, FL 34229

Welcome to the epitome of luxurious and hassle-free living in the coveted community of Bayside, a gated waterfront community of 49 homes on Little Sarasota Bay. This immaculate, like-new home, built in 2016 on an oversized lot with serene, private preserve views, has been meticulously maintained and offers a host of premium features that discerning buyers will appreciate. Upon arrival, you’ll be

Mike Warm PREMIER SOTHEBY'S INTERNATIONAL REALTY

3933 Waypoint Ave, Osprey, FL 34229

/85
Est $967,362 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 3,420 Sq Ft
184 Park Trace Blvd, Osprey, FL 34229

184 Park Trace Blvd, Osprey, FL 34229

/48
$1,200,000 Pending
- 3 Beds
- 2 Baths
- 2,531 Sq Ft
142 Dory Ln, Osprey, FL 34229

Southbay Yacht & Racquet Club, The waterfront Community with Resort-Style Amenities. Welcome to this beautiful three-bedroom two-bathroom home featuring a private pool and spa, perfect for relaxing or entertaining year-round. Located in a highly sought-after waterfront community, this property offers access to a private marina, clubhouse, community pool and scenic park-ideal for enjoying the

Sharon Lewis GOLF & BAY PROPERTIES LLC

142 Dory Ln, Osprey, FL 34229
/2
$210,000 Sold Sep 06, 2024
- 1,325 Sq Ft
- $158/SF
- 100 Days On Market
- 2 Beds
- 2 Baths
- Built 1979
120 Woodland Place Unit 120, Osprey, FL 34229

It's all about location and this bright second floor end unit is priced right and ready for you to make your own.Wonderful floor plan with spacious living area, primary ensuite and guest bedroom and a wonderful Breakfast Nook for your morning tea or coffee while catching up on the morning news. Walk down your steps and out the gate to take advantage of convenience. Grocery,

Maurice Menager MICHAEL SAUNDERS & COMPANY

120 Woodland Place Unit 120, Osprey, FL 34229

/36
Est $294,507 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,173 Sq Ft
429 Patterson Ave, Osprey, FL 34229

429 Patterson Ave, Osprey, FL 34229

/49
$499,000 Pending
- 3 Beds
- 2.5 Baths
- 2,166 Sq Ft
1110 Beachcomber Ct Unit 1, Osprey, FL 34229

Enjoy the best of coastal living in this spacious 2,166 sq. ft fully furnished townhouse condo, perfectly situated within walking distance of Casey Key and just steps from Casey Key Marina and Blackburn Point Park. This 15-acre waterfront park offers kayaking, fishing, a public boat ramp, and more. The thoughtfully designed first-floor master suite features a walk-in shower, a garden tub, and

Margaret Kennedy MICHAEL SAUNDERS & COMPANY

1110 Beachcomber Ct Unit 1, Osprey, FL 34229
/2
$512,500 Sold Sep 06, 2024
- 1,977 Sq Ft
- $259/SF
- 116 Days On Market
- 3 Beds
- 2 Baths
- Built 1995
515 Oak Bay Dr, Osprey, FL 34229

Welcome to your dream home nestled in the serene community of Bay Oaks in Osprey, Florida. This charming residence offers the perfect blend of comfort and convenience. As you approach the cul-de-sac street, you'll be greeted by the inviting curb appeal of this well-maintained property. The lush landscaping and manicured lawn frame the entrance, hinting at the beauty that awaits within.Step

Thomas Cail RE/MAX ALLIANCE GROUP

515 Oak Bay Dr, Osprey, FL 34229

/65
Est $596,292 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,335 Sq Ft
17 Bayhead Ln, Osprey, FL 34229

17 Bayhead Ln, Osprey, FL 34229

/2
$649,000 Pending
- Land
- 0.26 Acre
- $2,496,154 per Acre
0 Four Knot Ln, Osprey, FL 34229

Under contract-accepting backup offers. Do not miss your opportunity to build your dream home in the amenity-rich, waterfront community of Southbay Yacht and Racquet Club! This lot is only a short walk away from 10,000 square foot newly renovated clubhouse that overlooks the Southbay marina. The Power & Sail Club hosts events like potlucks, lunch cruises, and picnics. Boat life not for you? At

Gregory Wood CERUS REALTY

0 Four Knot Ln, Osprey, FL 34229
/2
$875,000 Sold Sep 03, 2024
- 2,015 Sq Ft
- $434/SF
- 93 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
1251 Windward Dr, Osprey, FL 34229

Priced below bank appraisal of $1,000,000!Located in the premier neighborhood of Southbay Yacht and Racquet, this home has been thoughtfully updated leaving you with minimal maintenance so you can truly enjoy all that fun there is to have with the many amenities this development has to offer. This property is move-in ready. With a newer roof, hurricane impact windows and all up to date

Lauren Doyle HORIZON REALTY INTERNATIONAL

1251 Windward Dr, Osprey, FL 34229

/71
Est $2,324,955 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,197 Sq Ft
892 MacEwen Dr, Osprey, FL 34229

892 MacEwen Dr, Osprey, FL 34229

/2
$1,950,000 Pending
- 4 Beds
- 4 Baths
- 4,132 Sq Ft
898 MacEwen Dr, Osprey, FL 34229

Large 4 bedroom, 4 bath home on over half an acre bordering the 7th fairway of the Heron Golf Course in the Oaks Clubside. Located in the heart of south Sarasota, The Oaks offers 2 championship golf courses, a world-class tennis facility, a state-of-the art wellness center and a wide variety of club amenities, including dining options and social offerings. Club membership is required with

Steve Abbe COLDWELL BANKER REALTY

898 MacEwen Dr, Osprey, FL 34229
/2
$850,000 Sold Aug 30, 2024
- 2,504 Sq Ft
- $339/SF
- 22 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2004
637 Crane Prairie Way, Osprey, FL 34229

BRING ALL YOUR OFFERS! The split floorplan places the master suite on the south side, featuring an expansive walk-in closet with custom organizers, and an en-suite bathroom with dual sinks, a soaking tub, and a separate shower. Luxury vinyl plank flooring graces the main living areas, while newly installed Karastan carpeting adorns the guest bedrooms. The residence includes upgrades such as new

Darrell Imbrosciano CENTURY 21 SCHMIDT REAL ESTATE

637 Crane Prairie Way, Osprey, FL 34229

/37
Est $1,271,901 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,742 Sq Ft
903 MacEwen Dr, Osprey, FL 34229

903 MacEwen Dr, Osprey, FL 34229

/76
$3,705,000
- 4 Beds
- 5.5 Baths
- 8,635 Sq Ft
112 Osprey Point Dr, Osprey, FL 34229

Premier Waterfront Opportunity in The Oaks BaysideThis grand estate home, perfectly positioned on a rarely available direct waterfront lot in the exclusive, gated Oaks Bayside community, offers sweeping views of Little Sarasota Bay and exceptional potential. With its expansive floor plan across three levels, soaring ceilings, and dramatic architectural features, this residence was built to

Kara Money KARA MONEY LLC

112 Osprey Point Dr, Osprey, FL 34229
/2
$2,500,000 Sold Aug 30, 2024
- 3,738 Sq Ft
- $669/SF
- 0 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2000
385 N Point Rd Unit 802, Osprey, FL 34229

This 3 bedroom, study, 3 1/2 bath penthouse residence in Meridian at the Oaks Preserve is beautifully renovated with high end finishes, a 2 car garage, has splendid sunsets and is offered furnished. Membership in the Oaks Country Club is required.

Rosalie Phillips MICHAEL SAUNDERS & COMPANY

385 N Point Rd Unit 802, Osprey, FL 34229

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