Winter Haven, FL Homes for Sale

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  /21

  $299,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,426 Sq Ft

  3335 Twilight Rd, Winter Haven, FL 33881

  From the front porch, you enter into the foyer and are immediately welcomed into the open family room, dining area, and kitchen. Just off the kitchen is the primary bedroom, which includes a primary bath, walk-in closet, and convenient access to the laundry room. The family room opens to a back patio, perfect for outdoor relaxation. On the opposite side of the kitchen, you’ll find two additional

  Starlight Homes Builder

  3335 Twilight Rd, Winter Haven, FL 33881
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  /57

  $74,900

  • 2 Beds
  • 2 Baths
  • 1,620 Sq Ft

  281 Putter Cir, Winter Haven, FL 33881

  2 Bed | 2 Bath | 1620 square foot | $74,900 (Swiss Golf and Tennis- Lot 281) 5K PRICE DROP! Seller Motivated and offering one-month FREE lot rent if closed by 4/1/2026. Beautifully updated and move-in ready home in a highly sought-after 55+ active golf community! This spacious open-layout home offers comfort, style, and plenty of room to relax or entertain. Partially furnished and loaded with

  Brandi Sappington CRF Communities

  281 Putter Cir, Winter Haven, FL 33881
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  /13

  $269,900

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  1911 Brown St NE, Winter Haven, FL 33881

  Location Location!! NO HOA, NO CDD, Built in 2020. QUIET, YET CONVENIENT LOCATION! Whether you're shopping for a first home, Investment or last home, this beauty is just what you’ve been looking for! Beautiful 3BR/2BA home open floor plan, living room/dinning groom /family room kitchen combo. located in NE Winter Haven. Large walk in closet in the Master Bedroom/Bath. Master bath contains a

  Manuel Duran Jr VYLLA HOME

  1911 Brown St NE, Winter Haven, FL 33881
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  /38

  $225,000

  • 2 Beds
  • 2 Baths
  • 2,190 Sq Ft

  6636 Westchester Dr NE, Winter Haven, FL 33881

  Welcome home to Lake N Golf Estates, a well loved 55+, no pet community situated on the sparkling shores of Lake Henry in sunny Winter Haven, FL! This beautifully maintained 2005 residence offers 2 bedrooms, 2 bathrooms, plus a dedicated office, and boasts an impressive 2,190 square feet of living space — making it the largest home in the community. Major updates provide peace of mind, including

  Laura Villardi COLDWELL BANKER REALTY

  6636 Westchester Dr NE, Winter Haven, FL 33881
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  /38

  $330,000

  • 4 Beds
  • 2 Baths
  • 1,876 Sq Ft

  4956 Jackson St, Winter Haven, FL 33884

  Built in 2023, this 4-bedroom, 2-bath Winter Haven home combines modern design with ultimate convenience. The bright, open-concept interior features ceramic tile floors and a chef-inspired kitchen with a large island. Relax on your screened-in lanai overlooking a private backyard. Located minutes from shopping, schools, and attractions—this move-in-ready gem is a must-see!

  Anthony Medina KELLER WILLIAMS REALTY SMART 1

  4956 Jackson St, Winter Haven, FL 33884
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  /40

  $229,999

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft

  3365 Raleigh Dr, Winter Haven, FL 33884

  ****PRICE IMPROVEMENT**** This home presents an exceptional opportunity to own in one of Winter Haven’s most desirable 55+ communities. This beautifully maintained 2-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and effortless Florida living. Step inside to a bright, open-concept layout where the living and dining areas flow seamlessly into the kitchen—creating an inviting

  James Barris EXP REALTY LLC

  3365 Raleigh Dr, Winter Haven, FL 33884
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  /39

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,725 Sq Ft

  3305 Royal Tern Dr, Winter Haven, FL 33881

  ***SHORT SALE*Discover Your Dream Home at Lakeside Landing! Welcome to this immaculate home in the picturesque community of Lakeside Landing! This property offers the ultimate in modern living, combining comfort, style, and functionality. It's move-in ready and equipped with smart home technology, energy-efficient windows, and SOLAR PANELS to help you save on energy costs. Plus, enjoy the privacy

  Brenda Anglada COLDWELL BANKER REALTY

  3305 Royal Tern Dr, Winter Haven, FL 33881
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  /9

  $139,900

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  6433 Jacaranda Ave NE, Winter Haven, FL 33881

  Significant price improvement and a highly motivated seller make this an exceptional opportunity in the sought-after 55+ Brookhaven Village community. This well-maintained manufactured home is truly move-in ready and offers both comfort and value. Major updates provide peace of mind, including a new roof installed in October 2024, fresh interior paint completed in March 2025, and an HVAC system

  Adriana Morales LA ROSA REALTY ORLANDO LLC

  6433 Jacaranda Ave NE, Winter Haven, FL 33881
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  /6

  $6,000,000

  • Land
  • 23.57 Acres
  • $254,561 per Acre

  0 Monroe Dr, Winter Haven, FL 33880

  Residential Land Location in Winter Haven, FL. Proposed 368 Units - Residential Multi-Family. Winter Haven is a city in central Florida, known for its canal-linked Chain of Lakes. Several lakes have waterside parks and eateries, as well as boat ramps and water-sports rentals. On Lake Eloise, Legoland Florida Resort includes Cypress Gardens, a 1930s botanical garden, and Lego-brick attractions,

  Bobby Luthra PROPERTY INVESTMENT BROKERS

  0 Monroe Dr, Winter Haven, FL 33880
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  /73

  $359,000

  • 5 Beds
  • 3 Baths
  • 2,616 Sq Ft

  605 Honey Bell Rd, Winter Haven, FL 33880

  Welcome home to this beautiful 2-story BLOCK HOME built in 2022 - still feels LIKE NEW and full of warmth and charm! This home offers INCREDIBLE SPACE, BRIGHT ROOMS, and a PEACEFUL WATER VIEW - perfect for family living and entertaining. Step inside to a welcoming foyer that opens to a FLEX ROOM - perfect for a formal dining room, formal living room or office. The kitchen is truly the HEART OF

  Yanery Perez XCELLENCE REALTY, INC

  605 Honey Bell Rd, Winter Haven, FL 33880
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  /34

  $274,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  2362 Brassie Ct, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Nestled in the growing Villamar community, this beautifully maintained 3-bedroom, 2-bath Meritage Home offers modern comfort and an ideal location near Chain of Lakes Elementary. Built with energy efficiency in mind, this newer home features an inviting open-concept floor plan where the kitchen flows seamlessly into the spacious great room—perfect

  Millie Brockmeyer RE/MAX INNOVATION

  2362 Brassie Ct, Winter Haven, FL 33884
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  /24

  $315,000

  • 4 Beds
  • 2 Baths
  • 1,707 Sq Ft

  1228 Denali Dr, Winter Haven, FL 33881

  NO CDD!! Newer 4 bedroom home for sale in Winter Haven, Florida, located in the Lake Lucerne II community in Polk County with no CDD fees and a low quarterly HOA. Built in 2023 by KB Home, this single-story residence offers approximately 1,707 square feet of modern living space designed for comfort, accessibility, and long-term value. Thoughtfully designed with universal design features, the home

  Jackie Mazurowski KELLER WILLIAMS REALTY SMART 1

  1228 Denali Dr, Winter Haven, FL 33881
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  /46

  $305,000

  • 3 Beds
  • 2 Baths
  • 1,597 Sq Ft

  3927 Palazzo Place, Winter Haven, FL 33884

  Do you want to own a true one of a kind? A true one of one? This is truly a special opportunity to own a home that is as unique as it is inviting. This property is the FINAL Amarylis model available in the entire community — a rare find that offers both distinction and immediate availability. Unlike new construction opportunities that often involve lengthy build timelines, unexpected delays, and

  Iliana Perez MAINFRAME REAL ESTATE

  3927 Palazzo Place, Winter Haven, FL 33884
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  /28

  $108,000

  • 2 Beds
  • 2 Baths
  • 1,920 Sq Ft

  1300 Las Brisas Ln Unit 343, Winter Haven, FL 33881

  2 Bedroom | 2 Bath | 1920 sq ft | $108,000 Four Lakes Golf Club Lot 343 Live Where Every Day Feels Like a Getaway - Golf Course Gem with Fountain Views Welcome home to 1300 Las Brisas Lane, Lot 343, where peaceful golf course living meets comfort, space and incredible value. Situated on the 18th hole, this 2 bedroom + den, 2 bath home offers 1,920 sq ft of open, light-filled living space with

  Cheryl Dobbs CRF Communities

  1300 Las Brisas Ln Unit 343, Winter Haven, FL 33881
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  /40

  $127,500

  • 2 Beds
  • 2 Baths

  1403 Wild Dunes Ct Unit 89, Winter Haven, FL 33881

  Great Home, Great Location & Extreme Storage potential!! $127,500 Ditch the storage unit - this home has an extremely large garage and additional shed storage in the back of the garage. Enough room for lots of storage, and 2 cars or that treasured Fishing Boat/Bass Boat & Trailer. Priced right at $127,500 in this wonderful community. This fantastic home also includes a large open concept kitchen,

  Deb Bartholomew Sunset Home Sales

  1403 Wild Dunes Ct Unit 89, Winter Haven, FL 33881
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  /71

  $139,900

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft

  5330 Laurel Oak Dr, Winter Haven, FL 33880

  Discover this exceptional 2018 manufactured home nestled on a prime cul-de-sac location at 5330 Laurel Oak Drive in Winter Haven Oaks community. Offered mostly furnished for your convenience, this residence provides immediate move-in ready comfort. This thoughtfully designed two-bedroom, two-bathroom home offers the perfect blend of comfort and convenience for discerning homeowners seeking an

  Chrissy Walter Sunset Home Sales

  5330 Laurel Oak Dr, Winter Haven, FL 33880
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  /15

  $250,000

  • 4 Beds
  • 2 Baths
  • 1,846 Sq Ft

  920 Cambridge Dr, Winter Haven, FL 33881

  SHORT SALE OPPORTUNITY PRICED TO SELL! Welcome to this 2021 built 4-bed 2 bath home located in the growing Windridge community of Winter Haven. This newer construction single story home offers a desirable open-concept floor plan designed for comfortable everyday living and easy entertaining. The spacious kitchen overlooks the main living and dining areas, creating a bright and inviting central

  Briana Willis Global Advantage Realty LLC

  920 Cambridge Dr, Winter Haven, FL 33881
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  /20

  $367,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,631 Sq Ft

  Primrose Plan at VillaMar - Signature Series, Winter Haven, FL 33884

  Entertain guests with ease with an open kitchen which overlooks the dining and great room. First floor flex space can be best used to fit your family's needs. Upstairs primary suite features an oversized walk-in closet.

  Meritage Homes Builder

  3745 Giorgio Dr Unit 37076789, Winter Haven, FL 33884
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  /31

  $315,000

  • 3 Beds
  • 2 Baths
  • 2,034 Sq Ft

  523 Little Lake Ct, Winter Haven, FL 33884

  Welcome to 523 Little Lake Court — a spacious 3-bedroom, 2-bath home on a generous lot in the heart of Winter Haven. Step through elegant double front doors with decorative glass and an arched transom into soaring vaulted ceilings that flow throughout the main living areas. The open layout features beautiful hardwood floors in the formal living and dining rooms, a large family room with a cozy

  Steven Koleno BEYCOME OF FLORIDA LLC

  523 Little Lake Ct, Winter Haven, FL 33884
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  Price To Be Determined New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,202 Sq Ft

  Plan 2202- at VillaMar - Villamar, Winter Haven, FL 33884

  Adams Homes Builder

  836 Vienna Dr Unit 36485333, Winter Haven, FL 33884
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  /43

  $220,000

  • 2 Beds
  • 2 Baths
  • 1,118 Sq Ft

  3343 Livingston Way, Winter Haven, FL 33884

  Located in the highly desirable 55+ maintenance-free gated community of Traditions on Lake Ruby, this wonderful 2-bedroom, 2-bathroom home offers charm, functionality, and an exceptional lifestyle. Upon arrival, you’re greeted by a welcoming Screened-in front porch decked out with tile flooring. Inside, the open-concept floor plan features a spacious living room with vaulted ceilings, Laminate

  Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  3343 Livingston Way, Winter Haven, FL 33884
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  $307,900 New Construction

  • 4 Beds
  • 2 Baths
  • 1,857 Sq Ft

  3111 Laurel Oak Ln, Winter Haven, FL 33884

  Move-in ready 4-bedroom home for sale in Winter Haven, Florida! This home features a spacious, open living area, a luxuriously appointed kitchen, and outdoor living space with a covered lanai and craftsman-style front porch! Enjoy privacy and relaxation in your spacious owner's suite complete with a large walk-in wardrobe and en-suite bath including a large tiled shower, dual vanities, a closeted

  Highland Homes Builder

  3111 Laurel Oak Ln, Winter Haven, FL 33884
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  /4

  $135,000

  • 2 Beds
  • 1 Bath
  • 708 Sq Ft

  3265 Conine Dr W, Winter Haven, FL 33881

  Cute 2 bed 1 bath home, in a quite area, oversized fenced lot, laminate floors, some renovations done.

  Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

  3265 Conine Dr W, Winter Haven, FL 33881
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  /17

  $65,000

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  910 La Quinta Blvd Unit 26, Winter Haven, FL 33881

  2 Bedrooms | 2 Bathrooms | 1,120 Sq. Ft. | $65,000 Four Lakes Golf Club Lot 26 Price reduced from $69,900 to $65,000 Comfort, Views and Value All in One Step into a home that offers more than just comfort - it delivers a lifestyle. This sweet, well-cared-for residence is ideally located near the entrance of this stunning golf community. The true gem of this home awaits in the back. The screened

  Cheryl Dobbs CRF Communities

  910 La Quinta Blvd Unit 26, Winter Haven, FL 33881
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  /2

  $356,990 New Construction

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

  2775 San Marco Way, Winter Haven, FL 33884

  This well-planned single-story home offers 4 bedrooms, 2 bathrooms, and approximately 2,100 square feet of living space with a 2-car garage. The open-concept layout features a spacious great room that flows seamlessly into the dining area and kitchen, creating an inviting space for everyday living and entertaining. The kitchen includes a center island, pantry, and ample counter space, with clear

  Maronda Homes Builder

  2775 San Marco Way, Winter Haven, FL 33884
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  /74

  $18,000

  • 2 Beds
  • 2 Baths
  • 896 Sq Ft

  62 Dale Dr, Winter Haven, FL 33880

  Seller is open to all offers. Make your own deal on this turnkey home! Whether you're looking to downsize, retire, or simply embrace the best of Florida's lifestyle, this 2 bedroom|2 bathroom in Winter Haven is the perfect place to make your dreams a reality. Winter Haven MHC is a 55+ pet-friendly community for active seniors. There is plenty of additional living space to entertain family/friends

  Patti Alvin Sunset Home Sales

  62 Dale Dr, Winter Haven, FL 33880
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  /27

  $284,990 New Construction

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft

  4952 Kaia Ave, Winter Haven, FL 33884

  The property is located at 4952 Kaia Avenue WINTER HAVEN FL 33884 priced at 284990, 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 Builder

  4952 Kaia Ave, Winter Haven, FL 33884
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  /47

  $382,000 New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,215 Sq Ft

  934 Cattleman St, Winter Haven, FL 33884

  Stunning 5BR/2.5BA single family home on an oversized lot in the sought-after Inman Groves community. Move-in-ready home offers 2,215sq. ft. of thoughtfully designed living space with high ceilings, tile/carpet floors, and an open-concept layout. The kitchen features a spacious island and flows into the expansive family room. Upstairs, the owner’s suite includes a large walk-in closet and private

  Cristina de Oliveira Miami New Realty

  934 Cattleman St, Winter Haven, FL 33884
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  /8

  $195,000

  • 2 Beds
  • 2.5 Baths
  • 2,045 Sq Ft

  28 Casarena Ct, Winter Haven, FL 33881

  Welcome to this charming two-story townhome located in the Casarena gated community in Winter Haven, offering 2 bedrooms and 2.1 bathrooms designed for comfort and flexibility. The inviting main living area features a cozy fireplace, perfect for relaxing or entertaining, while the functional layout flows seamlessly into the dining and kitchen spaces. Upstairs, enjoy your own private second-floor

  Jesse Carriedo REALTYCITY INC

  28 Casarena Ct, Winter Haven, FL 33881
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  /33

  $439,000

  • 4 Beds
  • 3 Baths
  • 2,748 Sq Ft

  3221 La Salle St, Winter Haven, FL 33884

  $81,000 Total Price Reduction | 4 Bedroom Home in Orleans – Winter Haven Chain of Lakes Area Located at 3221 La Salle St in the highly sought-after Orleans subdivision of Winter Haven, this 4-bedroom, 3-bathroom home offers nearly 2,800 square feet of well-designed living space in one of the most desirable areas near the Winter Haven Chain of Lakes. Positioned between Lake Winterset and Lake

  Don Jerue KELLER WILLIAMS REALTY SMART 1

  3221 La Salle St, Winter Haven, FL 33884
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  /2

  $49,000

  • Land
  • 1.01 Acres
  • $48,515 per Acre

  0 Gerber Dairy Rd Unit MFRO6269496, Winter Haven, FL 33880

  This 1.01-acre vacant lot on Gerber Dairy Road in Winter Haven, Florida, "Zoning: RC" offers a great opportunity to build your dream spot with space and privacy. Enjoy a peaceful setting while remaining conveniently close to local amenities, schools, and major roads. A perfect property to create your ideal Florida lifestyle.Pin Location: Latitude 27.94820195, Longitude -81.75169206. Note: buyers

  Samih Sadiq KELLY RIGHT REAL ESTATE

  0 Gerber Dairy Rd Unit MFRO6269496, Winter Haven, FL 33880
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  /38

  $325,000

  • 4 Beds
  • 2 Baths
  • 2,052 Sq Ft

  126 Bermuda Ct, Winter Haven, FL 33880

  The property you are inquiring about is located in Winter Haven, FL in the Emerald Acres/Grassy/Lake Estates area of Polk County. This beautiful lakefront, 4+ bedrooms, 2-bath home is situated on over 2 acres on Grassy Lake! Just needs a little TLC and a new owner to enjoy a relaxed lifestyle with a beautiful view! Call, text, and see! *Agents, please read MLS Remarks.*

  Renee Butler BROKERS REALTY OF CENTRAL FLOR

  126 Bermuda Ct, Winter Haven, FL 33880
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  /24

  $350,900 New Construction

  • 4 - 5 Beds
  • 3.5 Baths
  • 2,587 Sq Ft

  Wesley II Plan at VillaMar, Winter Haven, FL 33884

  Welcome home to the Wesley II by Highland Homes, a two-story Florida home that lives large with an open living area on the first story and a flexible second-story layout! Downstairs, enjoy a fully open living area with: A large gathering room. An open kitchen with a counter-height buttery island or optional galley island, a walk-in pantry, and a sunny dining cafe. A convenient powder room. An

  Highland Homes Builder

  521 Vittorio Dr Unit 37316138, Winter Haven, FL 33884
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  /30

  $89,900

  • 2 Beds
  • 2 Baths
  • 1,288 Sq Ft

  1614 Glen Abby Ln Unit 224, Winter Haven, FL 33881

  2 Bed | 2 Bath | 1,288 Sq Ft | $89,900 Four Lakes Golf Club Lot 224 Step into this beautifully decorated, furnished home perfectly positioned on the golf course-where every day feels like a retreat. From the moment you arrive, you'll love the inviting front sitting area and the convenience of your own golf cart garage. As an added bonus, enjoy ONE FREE year of golf and start living the lifestyle

  Cheryl Dobbs CRF Communities

  1614 Glen Abby Ln Unit 224, Winter Haven, FL 33881
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  /47

  $277,000

  • 3 Beds
  • 2 Baths
  • 1,470 Sq Ft

  1727 2nd St NE, Winter Haven, FL 33881

  Welcome to this beautifully built 2022 new construction home in Winter Haven, FL, offering the perfect blend of modern design, energy efficiency, and affordability — all conveniently located near Orlando’s world-famous attractions, including Walt Disney World and Universal Studios. Built by one of Winter Haven’s most recognized affordable builders, J&S Properties, this 3-bedroom, 2-bathroom,

  Regan Pappas REAL BROKER, LLC

  1727 2nd St NE, Winter Haven, FL 33881
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  /100

  $599,900

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

  5365 Hogan Ln, Winter Haven, FL 33884

  Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this immaculately maintained three-bedroom, two-bath home with a den offers exceptional comfort and elegance, including a beautiful primary suite with its own relaxing sitting room and a sparkling 71⁄2' x 36' bromine pool awaiting your enjoyment. From the striking stone

  Brad Kirwan GLOBAL LIFESTYLE LLC

  5365 Hogan Ln, Winter Haven, FL 33884
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  /41

  $18,990

  • 2 Beds
  • 1 Bath
  • 624 Sq Ft

  83 Stebbins Dr Unit 60, Winter Haven, FL 33884

  Welcome to your new slice of living in the heart of Central Florida! This two-bedroom, one-bathroom manufactured home has been thoughtfully remodeled and is ready for its next chapter. Nestled within 55+ community Grove Shores community, this home offers the perfect blend of comfort and convenience. The lot lease at 749.00 covers water, sewer, trash removal, and lawn care, meaning you can spend

  Chrissy Walter Sunset Home Sales

  83 Stebbins Dr Unit 60, Winter Haven, FL 33884
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  /13

  $298,000

  • 4 Beds
  • 2.5 Baths
  • 1,874 Sq Ft

  1985 Sarah St, Winter Haven, FL 33884

  Check out this upgraded Columbus on a corner lot! This expansive two-story Columbus has a well-designed layout, featuring a first floordedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, which has upgraded contertops,dining room and family room, with a patio extending the interior space outdoors, patio has also been upgraded with a 12x8

  Garrett Collins MARK SPAIN REAL ESTATE

  1985 Sarah St, Winter Haven, FL 33884
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  /51

  $335,000

  • 3 Beds
  • 2 Baths
  • 2,140 Sq Ft

  731 Canberra Rd, Winter Haven, FL 33884

  Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Cypresswood golf community in Winter Haven. Enjoy resort-style living with an 18-hole golf course, 24-hour gated security, clubhouse, community pool, and more. Inside, the renovated kitchen features granite countertops and custom cabinetry. The spacious primary suite offers a large ensuite bath

  Melissa Witter KELLER WILLIAMS REALTY SMART 1

  731 Canberra Rd, Winter Haven, FL 33884
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  /39

  $270,000

  • 3 Beds
  • 2 Baths
  • 1,666 Sq Ft

  2817 Wingfoot Ct, Winter Haven, FL 33884

  Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the prestigious Cypresswood Golf & Country Club, a guard-gated community offering both privacy and tranquility. Inside, you'll find three spacious bedrooms and two full bathrooms. The living and dining areas feature vaulted ceilings that enhance the open

  Dee Norris NEXTHOME NORRIS & COMPANY REAL

  2817 Wingfoot Ct, Winter Haven, FL 33884

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