Winter Haven, FL Homes

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  /65

  $725,000

  • 3 Beds
  • 3 Baths
  • 2,591 Sq Ft

  105 Wyndham Dr, Winter Haven, FL 33884

  GATED AND GUARDED WATERFRONT PROPERTY – WYNDHAM AT LAKE WINTERSET: Welcome to 105 Wyndham Drive, an extraordinary custom residence within the prestigious gated and guarded community of Wyndham at Lake Winterset. From the moment you arrive, the community sets the tone for elegance and prestige with its brick-paved entry, charming guardhouse, and manicured landscaping that changes with the seasons.

  Michael Stone THE STONES REAL ESTATE FIRM

  105 Wyndham Dr, Winter Haven, FL 33884
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  /30

  $2,450 per month

  • 5 Beds
  • 2.5 Baths
  • 2,254 Sq Ft
  • House for Rent

  1454 Austin Terrace, Winter Haven, FL 33884

  Make Winter Haven your new home. In Peace Creek Reserve, a master-planned community along a beautiful creek, this Edison home offers an open layout that integrates the kitchen, living room, and dining area and extends to the patio for outdoor enjoyment. Upstairs, five bedrooms surround a versatile loft (home office, study, or game room). The master suite offers a walk-in closet and en suite

  Carla Moreno Pineda EXP REALTY LLC

  1454 Austin Terrace, Winter Haven, FL 33884
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  /19

  $339,990 Sold Aug 13, 2025

  • 1,909 Sq Ft
  • $178/SF

  • 4 Beds
  • 2 Baths
  • Built 2025

  3494 Evening Star Dr, Winter Haven, FL 33881

  As you enter the home from the extended front porch, you’re welcomed into the foyer, where two bedrooms sit at the front of the home and share a full bath. Continuing down the hall, you'll find an additional bedroom and a conveniently located laundry room nearby. The heart of the home opens into the kitchen, seamlessly connected to the family room and dining area, creating an inviting space for

  Starlight Homes

  3494 Evening Star Dr, Winter Haven, FL 33881
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  /42

  Est $237,398 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,391 Sq Ft

  1572 Vienna Square Dr, Winter Haven, FL 33884

  1572 Vienna Square Dr, Winter Haven, FL 33884
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  /35

  $297,000

  • 4 Beds
  • 3 Baths
  • 2,212 Sq Ft

  685 Avenue N SE, Winter Haven, FL 33880

  Spacious 4-Bedroom, 3-Bath Pool Home with Office & Upgrades!Welcome to this 4-bedroom, 3-bath home offering approximately 2,212 square feet of comfortable living space. Step into the inviting double foyer that leads to an oversized family room/formal dining area, complete with a modern mini-split A/C system for year-round comfort. The newly remodeled bathroom and laundry room with

  Kelley Vogel Blackburn COLDWELL BANKER REALTY

  685 Avenue N SE, Winter Haven, FL 33880
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  /16

  $2,209 per month

  • 4 Beds
  • 2 Baths
  • 2,829 Sq Ft
  • House for Rent

  2753 Rochelle Dr, Winter Haven, FL 33881

  This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.0 bathrooms, and approximately 2,829 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your

  2753 Rochelle Dr, Winter Haven, FL 33881
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  /2

  $45,000 Sold Aug 13, 2025

  • 594 Sq Ft
  • $76/SF
  • 12 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1965

  216 Varnadoe Rd, Winter Haven, FL 33880

  Affordable Fixer-Upper with Extra Space – 216 Varnadoe Rd, Winter Haven, FLHere’s your chance to own a 2-bedroom, 1-bathroom home in the heart of Winter Haven—offered at an unbeatable price. Whether you’re an investor looking for your next project or a buyer ready to bring your vision to life, this property is packed with potential.The home sits on a generously sized lot and

  David Fleming BHHS FLORIDA PROPERTIES GROUP

  216 Varnadoe Rd, Winter Haven, FL 33880
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  /9

  Est $267,506 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,322 Sq Ft

  Unlisted Address

  Unlisted Address
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  /70

  $779,000

  • 4 Beds
  • 2.5 Baths
  • 2,549 Sq Ft

  2414 Gerber Dairy Rd, Winter Haven, FL 33880

  Enjoy peaceful country living on just under 5 acres with this 4-bedroom, 2.5-bath home in Winter Haven. Offering 2,549 sq ft, the split floor plan includes a spacious kitchen with breakfast nook, bar seating, and pantry, a family room with wood-burning fireplace, and a formal dining room. The primary suite features dual vanities, walk-in shower, soaking tub, and walk-in closet, while additional

  Jon Crow LPT REALTY, LLC

  2414 Gerber Dairy Rd, Winter Haven, FL 33880
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  /16

  $1,905 per month

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft
  • House for Rent

  3728 Imperial Dr, Winter Haven, FL 33880

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

  Nico Silva Vanegas MAIN STREET RENEWAL LLC

  3728 Imperial Dr, Winter Haven, FL 33880
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  /2

  $215,000 Sold Aug 13, 2025

  • 832 Sq Ft
  • $258/SF
  • 12 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1923

  423 Avenue H SE, Winter Haven, FL 33880

  Owner Financing Available! Welcome to 423 Avenue H SE — a beautifully updated 2-bedroom, 1-bathroom home located in the heart of Winter Haven. Just minutes from vibrant Downtown Winter Haven and the popular Cypress Gardens Boulevard, this home offers a perfect mix of character, convenience, and opportunity. Step inside to find original wood flooring that brings timeless charm, complemented by a

  Jason Stone BHHS FLORIDA PROPERTIES GROUP

  423 Avenue H SE, Winter Haven, FL 33880
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  /52

  Est $296,254 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,668 Sq Ft

  1359 Buckeye Trace Blvd, Winter Haven, FL 33881

  1359 Buckeye Trace Blvd, Winter Haven, FL 33881
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  /6

  $195,000

  • 3 Beds
  • 1 Bath
  • 1,076 Sq Ft

  1450 35th St NW, Winter Haven, FL 33881

  House in Winter Haven, Florida, with three bedrooms, one bathroom, and a laundry room. Recently renovated, cozy, and close to main routes, schools, and shopping. Just 30 minutes from Disney theme parks, Legoland, and much more. Excellent for investors and for your forever home.

  Josefina Carbon LA ROSA REALTY KISSIMMEE

  1450 35th St NW, Winter Haven, FL 33881
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  /18

  $1,939 per month

  • 4 Beds
  • 2 Baths
  • 1,643 Sq Ft
  • House for Rent

  194 Lake Thomas Dr, Winter Haven, FL 33880

  This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.0 bathrooms, and approximately 1,643 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your

  194 Lake Thomas Dr, Winter Haven, FL 33880
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  /2

  $274,000 Sold Aug 13, 2025

  • 1,768 Sq Ft
  • $155/SF
  • 126 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2018

  325 St Georges Cir, Eagle Lake, FL 33839

  Charm and curb appeal abound for this Eagle Lake home! Step inside into the inviting foyer and into the well-appointed living room, which sits at the center of the home. The kitchen features a four-piece appliance package, hard surface countertops, a pantry, and ample storage. Rounding out this ranch style floorplan is the home's laundry room, the primary suite, and three secondary bedrooms.

  Blake Keathley EVERYSTATE INC.

  325 St Georges Cir, Eagle Lake, FL 33839
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  /17

  Est $288,812 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft

  4729 Osprey Way, Winter Haven, FL 33881

  4729 Osprey Way, Winter Haven, FL 33881
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  /63

  $550,000

  • 3 Beds
  • 2 Baths
  • 2,006 Sq Ft

  1818 6th St SE, Winter Haven, FL 33880

  ***FULLY RENOVATED***Discover the perfect blend of modern upgrades and timeless charm in this beautifully updated 3-bedroom, 2-bathroom home.This beautiful house has now 2 extra bedrooms after renovations with the total 5 bedrooms, new kitchen, new living room, new floor, new bathrooms and the best new backyard in the city. Nestled between Orlando and Tampa with no HOA or CDD, this property

  Erika Pinto GARCIA REALTY GROUP

  1818 6th St SE, Winter Haven, FL 33880
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  /19

  $2,200 per month

  • 4 Beds
  • 2 Baths
  • 1,858 Sq Ft
  • House for Rent

  219 Cloverdale Rd, Winter Haven, FL 33884

  FOR RENT - 4 Bedroom/2 Bath Single Family Home in desirable SE Winter Haven. This home can be rented unfurnished for $2200 a month or completely furnished for $2500 a month. It is located right by LEGOLAND to the West and near Highway 27 to the East. The decorations and the furnishings are very contemporary and in good taste. The home opens up to a spacious formal living room and dining room

  Linda Andre COLDWELL BANKER REALTY

  219 Cloverdale Rd, Winter Haven, FL 33884
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  /2

  $375,000 Sold Aug 13, 2025

  • 3,023 Sq Ft
  • $124/SF
  • 292 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2014

  3540 Julius Estates Blvd, Winter Haven, FL 33881

  MAJOR PRICE REDUCTION! This stunning 5 bedroom, 3 bath, 2 car garage home in beautiful Lake Smart Estates offers the perfect blend of comfort and luxury. With over 3,000 square feet of living space, you'll have plenty of room to entertain or relax. As you step inside, you'll be greeted by a spacious open floor plan with custom porcelain tile flooring. The gourmet kitchen has everything a chef

  Twanna Dewdney LA ROSA REALTY PRESTIGE

  3540 Julius Estates Blvd, Winter Haven, FL 33881
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  /32

  Est $315,100 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,788 Sq Ft

  1591 Normandy Heights Blvd, Winter Haven, FL 33880

  1591 Normandy Heights Blvd, Winter Haven, FL 33880
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  /22

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,484 Sq Ft

  3832 Giorgio Dr, Winter Haven, FL 33884

  Immaculate, move in ready, 3bedroom/2 bath home. All appliances included with home. Blinds/curtains included. Open Floorplan great for Family get togethers. Neighborhood has 2 community pools, Clubhouse and playgrounds for your family ready to use. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include

  Alfredo Lopez FIERCE REALTY

  3832 Giorgio Dr, Winter Haven, FL 33884
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  /14

  $1,899 per month

  • 3 Beds
  • 2 Baths
  • 1,672 Sq Ft
  • House for Rent

  289 St Georges Cir, Winter Haven, FL 33880

  This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,672 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your

  289 St Georges Cir, Winter Haven, FL 33880
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  /28

  $279,990 Sold Aug 12, 2025

  • 1,665 Sq Ft
  • $168/SF

  • 4 Beds
  • 2 Baths
  • Built 2025

  4948 Kaia Ave, Winter Haven, FL 33884

  The property is located at 4948 Kaia Avenue WINTER HAVEN FL 33884 priced at 279990, the square foot and stories are 1665, 1.The number of bath is 2, halfbath is 0 there are 4 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton

  4948 Kaia Ave, Winter Haven, FL 33884
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  /3

  Est $304,221 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,825 Sq Ft

  4749 Osprey Way, Winter Haven, FL 33881

  4749 Osprey Way, Winter Haven, FL 33881
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  /68

  $299,000

  • 3 Beds
  • 1.5 Baths
  • 1,766 Sq Ft

  1380 Lucerne Loop Rd NE, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Amazing Lakefront Opportunity on Lake Lucerne! This beautifully updated 1959 charmer is perfectly situated on over half an acre of stunning lakefront property. This 3-bedroom, 1.5 bathroom home blends classic character with modern upgrades throughout. Enjoy natural light streaming through the spacious living and family rooms, creating a warm and

  Harold Baker KELLER WILLIAMS REALTY SMART 1

  1380 Lucerne Loop Rd NE, Winter Haven, FL 33881
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  /33

  $1,950 per month

  • 3 Beds
  • 2.5 Baths
  • 1,625 Sq Ft
  • House for Rent

  2574 Pine Place, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. ***Move in today and enjoy your first month absolutely FREE! Don’t miss this limited-time offer to snag the perfect home at an unbeatable value!***Discover 2562 Pine Place, a beautifully maintained 3-bedroom, 2.5-bath home offering the perfect blend of modern comfort and tranquil waterfront living. Wake up to peaceful water views from your own

  Jacob Hara TRANSCEND REALTY

  2574 Pine Place, Winter Haven, FL 33881
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  /2

  $224,999 Sold Aug 12, 2025

  • 1,400 Sq Ft
  • $161/SF
  • 9 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  575 Avenue M SE, Winter Haven, FL 33880

  Welcome to 575 Ave M SE — a beautifully refreshed home offering space, style, and incredible potential! Nestled on almost a quarter-acre lot, this property features a roundabout driveway for easy access and ample parking.Step inside to find fresh new paint, stylish newer flooring, NEW water heater and a modern kitchen with a new backsplash. The newer AC keeps things cool and efficient, while

  Destini Lewis LA ROSA REALTY PRESTIGE

  575 Avenue M SE, Winter Haven, FL 33880
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  /29

  Est $177,686 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 930 Sq Ft

  7906 Waterview Way Unit 7906, Winter Haven, FL 33884

  7906 Waterview Way Unit 7906, Winter Haven, FL 33884
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  /31

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft

  701 Reflections Dr, Winter Haven, FL 33884

  Experience the perfect blend of comfort and style in this stunning 3-bedroom, 2-bathroom home, nestled in the sought-after Reflections East community—just minutes from LEGOLAND! Move-in ready with modern updates, this home features a newer roof (2019), some newer windows (2020), and a newer air conditioner (2022) for worry-free living. Designed for effortless everyday life, it offers a warm and

  Hailey Cornell WATERS REAL ESTATE GROUP

  701 Reflections Dr, Winter Haven, FL 33884
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  /20

  $2,039 per month

  • 4 Beds
  • 2 Baths
  • 1,852 Sq Ft
  • House for Rent

  6279 Red Herring Dr, Winter Haven, FL 33881

  This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.0 bathrooms, and approximately 1,852 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your

  6279 Red Herring Dr, Winter Haven, FL 33881
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  /2

  $302,500 Sold Aug 12, 2025

  • 1,768 Sq Ft
  • $171/SF
  • 62 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2018

  305 St Georges Cir, Eagle Lake, FL 33839

  $10,000 Price Reduction***This stunning, professionally designed and decorated Former Model Home is now available for sale in the sought-after Winter Haven area. The Parker is one of Highland Homes top-selling Florida home plans and offers a bright, open living space ideal for modern living. Key Features: 1. Open Concept Living: The spacious gathering room, dining cafe, and kitchen with a

  LaChelle Olivet PALERMO REAL ESTATE PROF. INC.

  305 St Georges Cir, Eagle Lake, FL 33839
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  /54

  Not Listed For Sale

  • 2 Beds
  • 1.5 Baths

  415 Seagull Dr Unit 415, Winter Haven, FL 33881

  415 Seagull Dr Unit 415, Winter Haven, FL 33881
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  /5

  $75,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  17 Lake Shipp Ct, Winter Haven, FL 33880

  Charming 2BR/1BA SFH with 672 sq ft on a 4,996 sq ft lot. Features include a 700 sq ft upstairs loft + downstairs loft, concrete flooring, front porch, and window A/C units. Kitchen & bath ready for updates—great opportunity to add your personal touch!

  Cliff Glansen FLATFEE.COM

  17 Lake Shipp Ct, Winter Haven, FL 33880
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  /33

  $1,950 per month

  • 3 Beds
  • 2.5 Baths
  • 1,625 Sq Ft
  • House for Rent

  2568 Pine Place, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Welcome to 2568 Pine Pl, a stunning 3-bedroom, 2.5-bath home nestled in the heart of Winter Park, FL—where comfort meets serene waterfront living. Enjoy peaceful water views right from your backyard, perfect for morning coffee or evening relaxation. This beautifully maintained property offers a spacious, open layout, modern kitchen, and a primary

  Jacob Hara TRANSCEND REALTY

  2568 Pine Place, Winter Haven, FL 33881
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  /2

  $240,000 Sold Aug 12, 2025

  • 1,258 Sq Ft
  • $191/SF
  • 65 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2020

  392 Kensington View Dr, Winter Haven, FL 33880

  Welcome to 392 Kensington View Drive in Winter Haven. Built in 2020, this 3-bedroom, 2-bath home sits in a quiet gas community and includes a 1-car garage. Inside, you’ll find tile flooring throughout the main living areas, a tankless hot water heater, and a full irrigation system that wraps around the entire property. The 12x30 screened and paved lanai offers plenty of space to relax or

  Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

  392 Kensington View Dr, Winter Haven, FL 33880
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  /2

  Est $210,745 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,053 Sq Ft

  1665 Teagan Ln, Winter Haven, FL 33884

  1665 Teagan Ln, Winter Haven, FL 33884
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  /29

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,521 Sq Ft

  1883 Galloway Terrace, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Welcome to this charming, well-maintained home in the desirable gated community of Buckeye Trace in Winter Haven, Florida! This 3-bedroom, 2-bathroom home offers an open floor plan with high ceilings and tile floors in the main living areas. The stylish kitchen features a functional island with extra counter space for meal prep and plenty of room

  Nankumar Seelall HOMESMART

  1883 Galloway Terrace, Winter Haven, FL 33881
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  /17

  $1,795 per month

  • 3 Beds
  • 2 Baths
  • 1,397 Sq Ft
  • House for Rent

  966 Sunshine Way SW, Winter Haven, FL 33880

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $1939.90. That covers your base rent, $1795.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  966 Sunshine Way SW, Winter Haven, FL 33880
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  /2

  $204,500 Sold Aug 12, 2025

  • 1,575 Sq Ft
  • $130/SF
  • 87 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1994

  1531 Oakview Cir SE, Winter Haven, FL 33880

  Welcome to the well-maintained 55+ owner occupant community of Oakview located in beautiful Winter Haven, Florida. This is a two bedroom two bath tastefully furnished home. The split bedroom plan gives lots of privacy to guests or residents. The living/dining room combination is spacious and located right off the kitchen for ease of entertaining family and friends. There is a den at the rear

  Brenda J. Quinn QUINN & COMPANY REALTORS, LLC

  1531 Oakview Cir SE, Winter Haven, FL 33880
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  /99

  Est $525,667 Not Listed For Sale

  • 8 Beds
  • 4 Baths
  • 3,456 Sq Ft

  227 Palmetto Ave NW, Winter Haven, FL 33881

  227 Palmetto Ave NW, Winter Haven, FL 33881

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