Osprey, FL Homes for Sale with Parking

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  /88

  $2,900,000

  • 6 Beds
  • 6.5 Baths
  • 6,246 Sq Ft

  236 Saint James Park, Osprey, FL 34229

  Tucked away in a quiet cul-de-sac on a double lot beneath majestic oaks, this almost 5,000 sq ft, timeless 2-story home blends sophistication with modern comfort. Situated on the first hole of Heron Golf Course, the home features soaring 11-ft ceilings, marble floors, and crystal chandeliers. A Louis XVI fireplace anchors the sunken living room, while French doors and expansive windows invite

  Karin Watt MICHAEL SAUNDERS & COMPANY

  236 Saint James Park, Osprey, FL 34229
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  /66

  $735,000

  • 4 Beds
  • 3 Baths
  • 2,589 Sq Ft

  826 Oak Briar Ln, Osprey, FL 34229

  Welcome to this MODERN 4-Bedroom, 3-Bath POOL HOME located in the highly desirable PARK TRACE ESTATES in Osprey, Florida — perfectly situated in a PRIME LOCATION between Sarasota, Nokomis, and Venice. Boasting over 3,000 sq. ft. under roof along with $110,000 of RECENT IMPROVEMENTS including: NEW TILE ROOF (’23), NEW impact windows (’23, partial), NEW front door (’23), NEW high-end air condition

  Peter LaSalle PREFERRED SHORE LLC

  826 Oak Briar Ln, Osprey, FL 34229
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  /61

  $614,000

  • 3 Beds
  • 2.5 Baths
  • 2,130 Sq Ft

  51 Webb St, Osprey, FL 34229

  ***PRICE IMPROVEMENT***Location, Location, Location! Situated west of the trail in the heart of Osprey, this stunning 3-bedroom, 2-bathroom plus den ranch home is a rare find, just steps from Sarasota Bay. Enjoy a tranquil coastal lifestyle, with the Main Street fishing pier, Spanish Pointe Marina, Oscar Scherer State Park, and the renowned Pine View School for the Gifted close by.

  Marina Myers FINE PROPERTIES

  51 Webb St, Osprey, FL 34229
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  /35

  $260,000

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft

  111 Woodland Place, Osprey, FL 34229

  Property comes furnished.Rare, 1st floor condo in Pine Run. Unique layout with center outdoor solarium for peaceful retreat. This 2 bd, 2 bath offers lots of space and privacy. Large exp lanai and an outdoor eating area off kit. Beautiful newer luxury vinyl floors. New hot water heater, young air/heating unit. Nicely located carport and lots of storage. Pine Run has two pools, tennis and

  Stephen Hachey FLAT FEE MLS REALTY

  111 Woodland Place, Osprey, FL 34229
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  /64

  $4,750,000

  • 3 Beds
  • 3 Baths
  • 2,582 Sq Ft

  1049 N Casey Key Rd, Osprey, FL 34229

  Seize the opportunity to own a piece of paradise on the exclusive North Casey Key. This sprawling one-plus-acre estate, with 107 feet of pristine gulf frontage, a walkable sandy beach, on a private road with security offering unparalleled privacy, is your personal slice of heaven. Surrounded by majestic live oaks, this property is a rare gem that embodies the timeless beauty of Old Florida

  Lisa Napolitano PREMIER SOTHEBYS INTL REALTY

  1049 N Casey Key Rd, Osprey, FL 34229
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  /60

  $11,750,000

  • 5 Beds
  • 8 Baths
  • 8,050 Sq Ft

  1216 N Casey Key Rd, Osprey, FL 34229

  This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1216 N Casey Key Rd, Osprey, FL 34229
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  /59

  $774,900

  • 3 Beds
  • 2 Baths
  • 2,171 Sq Ft

  866 Placid Lake Dr, Osprey, FL 34229

  Immerse yourself in the blissful lifestyle located in the Woodlands of Rivendell, where this beautifully appointed home awaits. Situated within a community renowned for its expansive green spaces, parks, 24 shimmering lakes, proximity to Oscar Scherer State Park, heated community pool and nearby Pine View School, this residence offers a truly exceptional living experience. This enchanting

  Justin Brunswick KELLER WILLIAMS ON THE WATER S

  866 Placid Lake Dr, Osprey, FL 34229
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  /95

  $2,695,000

  • 4 Beds
  • 3.5 Baths
  • 3,953 Sq Ft

  49 Osprey Point Dr, Osprey, FL 34229

  Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes,

  Jonathan Abrams MICHAEL SAUNDERS & COMPANY

  49 Osprey Point Dr, Osprey, FL 34229
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  /51

  $950,000

  • 3 Beds
  • 2.5 Baths
  • 2,199 Sq Ft

  14021 Bellagio Way Unit 309, Osprey, FL 34229

  A boaters paradise. Discover the epitome of coastal living in this stunning 3-bedroom, 2.5-bathroom condo located in the highly desired, Bellagio Harbor Village. Nestled in between Sarasota Big Pass and the Venice Jetty, just minutes from Midnight pass and the gulf, this property offers prompt access to Sarasota County’s pristine beaches, fine dining, and boutique shopping.With a generous

  Tristin Hopler EXP REALTY LLC

  14021 Bellagio Way Unit 309, Osprey, FL 34229
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  /50

  $1,685,000

  • 3 Beds
  • 3 Baths
  • 2,402 Sq Ft

  364 El Greco Dr, Osprey, FL 34229

  This exquisite waterfront residence offers a dreamlike lifestyle with expansive views of the canal and bay, making it a gem in Sorrento Shores. Boaters dream, 10,000-pound lift in your backyard, 20 minutes to Venice Inlet with access to the turquoise waters of The Gulf. On a prime cul-de-sac lot, the home boasts a stunning circular driveway adorned with majestic Royal Palms, enhancing its curb

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  364 El Greco Dr, Osprey, FL 34229
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  /92

  $1,300,000

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft

  393 N Point Rd Unit 604, Osprey, FL 34229

  Immerse yourself in the unparalleled, unobstructed views of Little Sarasota Bay, the Gulf of Mexico and Midnight Pass, with Casey Key and Siesta Key gracing the horizon from this 6th-Floor Corner Unit Condo. Marvel at the gorgeous water views during the day and the stunning sunsets in the evening from your expansive, sweeping balcony, which feels like an additional room. Experience the epitome

  Debbie Baraona ROBERT SLACK LLC

  393 N Point Rd Unit 604, Osprey, FL 34229
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  /49

  $2,350,000

  • 3 Beds
  • 2 Baths
  • 1,977 Sq Ft

  18 N Casey Key Rd, Osprey, FL 34229

  Beautifully remodeled in 2012, this bayfront residence combines elegance, functionality and an enviable location. The living room, kitchen and family room are great places to gather, and the split floor plan provides room for all, privacy to retreat with a good book or work from home options. The classic coastal style provides a view of the bay and intracoastal waterway from the primary bedroom.

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  18 N Casey Key Rd, Osprey, FL 34229
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  /44

  $910,000

  • 3 Beds
  • 2 Baths
  • 2,271 Sq Ft

  293 Turquoise Ln, Osprey, FL 34229

  **STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure Gates of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank, Plantation Shutters, an Oversized, Owner’s

  Mark Lyda GENEROUS PROPERTY

  293 Turquoise Ln, Osprey, FL 34229
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  /64

  $699,900

  • 4 Beds
  • 3 Baths
  • 2,298 Sq Ft

  644 Rivendell Blvd, Osprey, FL 34229

  Optional Turnkey! Built in 2001, this home features high tray ceilings and a smart, functional layout.The formal living and family rooms, along with the en-suite primary bedroom, open to the lanai. The dining room includes custom built-ins, while two guest bedrooms share a hall bathroom. A private in-law suite, currently used as an office, has its own bathroom and lanai access.The

  Veronica Manes MICHAEL SAUNDERS & COMPANY

  644 Rivendell Blvd, Osprey, FL 34229
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  /51

  $540,000

  • 3 Beds
  • 2 Baths
  • 2,559 Sq Ft

  566 Oak Bay Dr, Osprey, FL 34229

  **Seller is motivated**Welcome to Bay Oaks Estates. This 3-bedroom 2 bath plus den is a classic Florida home featuring a pool with mosaic inspired ocean theme. And with no one behind you and no houses in front offers plenty of privacy. Oh, I almost forgot this home offers a wood burning fire place for those couple of cold nights a year, lol. New roof September 2022 newer water heater. This

  Greg Walters SARABAY REAL ESTATE INC

  566 Oak Bay Dr, Osprey, FL 34229
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  /68

  $324,900

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft

  294 Hidden Bay Dr Unit 203, Osprey, FL 34229

  Escape from the hustle and bustle of the real world to the charms of Hidden Bay. Located on 12 beautiful acres on Little Sarasota Bay, this gated community offers waterfront play and relaxation. Spend your perfect day at the amenity rich community clubhouse/pool or kayaking on Intracoastal waters. This lovely two-bedroom, two-bath home is roomy and bright, offering a den/office along with a

  Kristen Redding MICHAEL SAUNDERS & COMPANY

  294 Hidden Bay Dr Unit 203, Osprey, FL 34229
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  /62

  $409,900

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  2251 Jessie Harbor Dr, Osprey, FL 34229

  **1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO (No Bridges)** Featuring 2 BEDS and 2 FULL BATHS, this LIGHT AND BRIGHT, 1ST FLOOR END UNIT dwelling features an Impressive Kitchen with Granite counters, Stainless Steel appliances and solid wood cabinets while the Spacious

  Mark Lyda GENEROUS PROPERTY

  2251 Jessie Harbor Dr, Osprey, FL 34229
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  /55

  $845,000

  • 4 Beds
  • 4 Baths
  • 3,183 Sq Ft

  650 Crane Prairie Way, Osprey, FL 34229

  BEST PRICED HOME PER SQ FT in a 3-Mile Radius! Now Offered at $845,000 | Lease Option/Purchase Available!Live large in this 3,183 sq ft Lee Wetherington masterpiece with private pool and preserve OSCAR SCHERE PARK views in the coveted Willowbend community—just minutes from Casey Key Beach and the nationally ranked Pine View School for the Gifted. Offering over 3,180 sq ft, this home features

  Cheri Castro KELLER WILLIAMS ON THE WATER

  650 Crane Prairie Way, Osprey, FL 34229
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  /75

  $230,000

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft

  201 Woodland Dr Unit 201, Osprey, FL 34229

  Rarely available 1st floor end unit!

  Lauren Meadows PREFERRED PROPERTIES OF VENICE INC

  201 Woodland Dr Unit 201, Osprey, FL 34229
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  /70

  $485,000

  • 2 Beds
  • 3 Baths
  • 2,837 Sq Ft

  264 Woods Point Rd, Osprey, FL 34229

  One or more photo(s) has been virtually staged. SELLER WILL CONSIDER LEASE PURCHASE. Try it before you buy it. Experience maintenance free Florida living, just a short walk, bike or drive to Casey Key in this large villa situated in the rarely available neighborhood of Blackburn Point Woods. The home greets visitors with a large welcoming paver patio providing a place to relax and greet your

  Mark Midyett KELLER WILLIAMS ON THE WATER S

  264 Woods Point Rd, Osprey, FL 34229
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  /61

  $261,800

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft

  758 Pine Run Dr Unit 758, Osprey, FL 34229

  This home was professionally inspected by a Contractor following Hurricanes Helene and Milton, and I’m pleased to report it sustained no damage from the storms. Welcome to this beautifully updated, spacious 2-story condo, boasting 2 bedrooms, 2.5 bathrooms, and updated modern finishes throughout. Nestled in a desirable community, you'll be just minutes from the beach, with easy access to

  Greg Vander Wel REALNET FLORIDA REAL ESTATE

  758 Pine Run Dr Unit 758, Osprey, FL 34229
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  /38

  $185,000

  • 2 Beds
  • 2 Baths
  • 1,376 Sq Ft

  191 Palm Air Dr, Osprey, FL 34229

  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 square feet of centrally-cooled comfort. Two

  John Alexander FINE PROPERTIES

  191 Palm Air Dr, Osprey, FL 34229
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  /90

  $795,000

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft

  409 N Point Rd Unit 501, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Welcome to luxury condo living in The Oaks Preserve. This 3 bedroom, 3 bath corner unit with office, offers everything you need to live the country club lifestyle with comfort and ease. Take your private elevator to the 5th floor and you will find this lovely residence in pristine condition. The kitchen has stainless steel appliances, breakfast

  Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 501, Osprey, FL 34229
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  /48

  $269,999

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft

  207 Woodland Dr Unit 207, Osprey, FL 34229

  Welcome to this beautifully appointed, well-cared for and fully furnished 2-bedroom, 2-bath condo located in the sought-after Pine Run community. It is completely turnkey; all you need to bring are your clothes! This second-floor unit has been tastefully updated and comes equipped with everything you need to move right in, including all furniture, beds, bedding, all kitchenware, appliances, and

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  207 Woodland Dr Unit 207, Osprey, FL 34229
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  /93

  $719,000

  • 3 Beds
  • 3 Baths
  • 2,203 Sq Ft

  409 N Point Rd Unit 603, Osprey, FL 34229

  BEAUTIFUL FULL WATER VIEWS OF NORTH CREEK, SARASOTA BAY, AND THE GULF! Watch the eagles and osprey fish and enjoy truly stunning sunsets from the balcony of this condo with 3 bedrooms, 3 full baths and a formal dining room/den. With this condo you have found a best-priced gem in Meridian at The Oaks Preserve to enjoy all the Gulf Coast has to offer. Take the private elevator to the sixth floor

  Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 603, Osprey, FL 34229
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  /94

  $1,549,000

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft

  401 N Point Rd Unit 901, Osprey, FL 34229

  This opulent 3 bedroom plus den, 3 bath residence with a PRIVATE 2 CAR GARAGE located in Meridian at The Oaks Preserve, is a dream come true! A penthouse-level end unit situated on the north side of the building, it has been carefully updated and meticulously maintained. From the moment you step off your private elevator you will be impressed by this spacious unit. 10 foot ceilings,

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 901, Osprey, FL 34229
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  /4

  $527,904 New Construction

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft

  791 S Tamiami Trail Unit 102, Osprey, FL 34229

  Pre-Construction. To be built. PRE CONSTRUCTION STARTING FROM $527,904. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOWN AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 2 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (3 BEDROOM AND 2 BATH UNITS ALSO

  Laurie Eshleman PRO GROUP REALTY & PROP MGT

  791 S Tamiami Trail Unit 102, Osprey, FL 34229
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  /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
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  /68

  $639,000

  • 2 Beds
  • 2 Baths
  • 1,766 Sq Ft

  9492 Forest Hills Cir, Sarasota, FL 34238

  Welcome to this beautifully appointed 2-bedroom, 2-bath, Plus a Den villa with stunning panoramic views of the golf course and a tranquil pond—an ideal setting for elegant, maintenance-free living. Located in the highly desirable Forest Hills section of Stoneybrook at Palmer Ranch, this villa features a spacious split floor plan that offers privacy for guests, with a guest bedroom and full bath.

  Mimi Kruk MICHAEL SAUNDERS & COMPANY

  9492 Forest Hills Cir, Sarasota, FL 34238
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  /50

  $545,000

  • 4 Beds
  • 2.5 Baths
  • 3,008 Sq Ft

  9528 Knightsbridge Cir, Sarasota, FL 34238

  LAKEVIEW! NEW ROOF 2021! EXTERIOR AND INTERIOR PAINT 2025! NEW CARPETING UPSTAIRS! Welcome to 9528 Knightsbridge Circle, a spacious lakefront residence located in the highly desirable Stoneybrook Estates at Palmer Ranch. This inviting home features 4 bedrooms, 2.5 bathrooms, plus a versatile den—perfect for a home office or playroom. Enjoy peace of mind with a NEW ROOF in 2021, a NEW A/C system

  Michelle Segatto KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  9528 Knightsbridge Cir, Sarasota, FL 34238
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  /46

  $725,000

  • 3 Beds
  • 2 Baths
  • 1,918 Sq Ft

  5301 Bartolomeo St, Sarasota, FL 34238

  Discover the exceptional lifestyle offered in Esplanade on Palmer Ranch with this beautiful Arrezo model home, perfectly situated on a private cul-de-sac. This vibrant and active community boasts a wealth of amenities, including the Bahama Bar for dining and social activities, pickleball and tennis courts, a well-equipped fitness center, and a breathtaking resort-style pool that could rival the

  Anne Friedland BLUESRQ REAL ESTATE INC

  5301 Bartolomeo St, Sarasota, FL 34238
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  /58

  $1,600,000

  • 3 Beds
  • 3 Baths
  • 2,994 Sq Ft

  5329 Trails Bend Ct, Sarasota, FL 34238

  Discover your dream home in the prestigious Legacy Estates, where luxury meets comfort in a resort-style setting. This exquisite property features a private courtyard and boasts high ceilings with an open floorplan, perfect for modern living and entertaining. With three ensuite bedrooms and ample linen closets, this home offers both privacy and convenience. The interior showcases numerous

  Coreen Wilde MICHAEL SAUNDERS & COMPANY

  5329 Trails Bend Ct, Sarasota, FL 34238
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  /70

  $584,000

  • 3 Beds
  • 2.5 Baths
  • 1,849 Sq Ft

  9590 Knightsbridge Cir, Sarasota, FL 34238

  One or more photo(s) has been virtually staged. Welcome to your beautifully updated 3 bedroom 2 1/2 bathroom, 2 car garage home in Stoneybrook. Be ready to enjoy the large living area and open floor plan with pool and water views. Great home layout for entertaining or relaxing. This wonderful home is freshly painted, clean and bright and a must see! The kitchen features new wood cabinets,

  Kathleen Goff KATHLEEN GOFF LICENSE R.E. BROKER

  9590 Knightsbridge Cir, Sarasota, FL 34238

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