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3843 Eloise Estates Court, Winter Haven
$280,000
3 Beds ⋅ 2 Baths ⋅ Lake Smart Estates SubDv. ⋅ 33881 Zip Code
HUGE PRICE REDUCTION! POND-VIEW MOVE-IN READY HOME! Enjoy a serene setting and modern updates including tile flooring & kitchen backsplash (2022) and a NEW ROOF (2023). Kitchen features granite countertops and stainless steel refrigerator. Spacious master suite with pond view, walk-in closet, and large bathroom. Split bedroom layout offers privacy and comfort. Located near Lake Smart with Chain of Lakes access! Community offers a pool and is just a short walk to the lake. This community also offers a community dock so bring your poles. Conveniently located near HWY 27, I-4, and HWY 60. Approx. 6 miles to LEGOLAND, 4 miles to Winter Haven Hospital & Publix, and 6 miles to Winter Haven Regional Airport. Furnishings negotiable (TVs do not convey). Schedule your showing today—don’t miss this opportunity!

3843 Eloise Estates Court, Winter Haven

602 Taylor Boulevard, Winter Haven
$220,000
3 Beds ⋅ 2 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code
Short Sale. Welcome to this charming three-bedroom, two-bathroom home, perfectly situated for comfortable living. The inviting open concept layout seamlessly integrates the kitchen, living, and dining areas, adorned with luxury vinyl plank flooring that adds both style and durability. The well-appointed kitchen features beautiful granite countertops, complemented by sleek black appliances, crisp white cabinets, and a classic white subway tile backsplash, along with a convenient counter-height breakfast bar for casual dining. With significant updates including a new roof, air conditioner, and water heater all installed in 2022, this home offers peace of mind for future years. Enjoy the ease of laundry access off the carport and relax in the privacy of the fenced backyard. With a one-car carport and a warm, welcoming ambiance, this home is a delightful find for anyone seeking a cozy retreat.

602 Taylor Boulevard, Winter Haven

3307 Fox Ridge Drive, Winter Haven
$230,000
3 Beds ⋅ 2 Baths ⋅ Fox Ridge Ph 01 SubDv. ⋅ 33884 Zip Code
Short Sale. BANK APPROVED PRICE! Welcome to your 3 bedroom 2 bathroom home located conveniently in Winter Haven with easy access to shopping, dining, and major roadways. The roof and AC were replaced in 2023. This home features luxury vinyl plank flooring throughout. The living room is spacious and features vaulted ceilings. The kitchen has been remodeled and features newer cabinets and granite countertops and a closet pantry. The primary bedroom is spacious with a walk in closet and en-suite bathroom. The remaining bedrooms offer plenty of space and share the main hall bathroom featuring a single sink vanity and tub/shower combo. The home also features a large screened in back porch, the perfect spot for entertaining. This home has so much to offer. Schedule your private showing today!

3307 Fox Ridge Drive, Winter Haven

1109 5th Street Sw, Winter Haven
$195,000
3 Beds ⋅ 2 Baths ⋅ South College SubDv. ⋅ 33880 Zip Code
Under contract-accepting backup offers. Short Sale. Discover the exceptional potential of this 3-bedroom, 2-bathroom home ideally located in the heart of Winter Haven, offering unbeatable access and flexibility with no HOA restrictions. Positioned just minutes from major highways, shopping centers, dining, and local amenities, this property delivers convenience that’s hard to match. Inside, the home features a spacious living area, an updated kitchen with ample cabinet space, and a comfortable primary suite designed for everyday living. Outside, the generous fenced-in lot provides room for entertaining, expansion, or future development. What truly sets this property apart is its strategic location, making it a strong candidate for Commercial or Industrial rezoning. Whether you envision office space, a retail storefront, business headquarters, long-term rental, or continued residential use, the possibilities are wide open. Perfectly suited for homeowners, investors, or entrepreneurs, this Winter Haven property combines location, accessibility, and potential. Don’t miss this rare opportunity, schedule your private showing today!

1109 5th Street Sw, Winter Haven

3923 Baldwin Lane, Winter Haven
$253,900
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 1 SubDv. ⋅ 33884 Zip Code
Under contract-accepting backup offers. NEW PRICE IMPROVEMENT! WELCOME TO 3923 BALDWIN LANE, NEW ROOF 2023, NEW A/C 2025, FRESHLY PAINTED 2024, RECENT IMPROVEMENTS INCLUDE A NEW GARBAGE DISPOSAL AND THE ADDITION OF A NEW CLOSET IN THE THIRD BEDROOM, ENHANCING BOTH CONVENIENCE AND STORAGE SPACE. LOCATED IN THE HIGHLY SOUGHT-AFTER TRADITIONS GATED COMMUNITY IN WINTER HAVEN! THIS BEAUTIFULLY MAINTAINED HOME OFFERS THE PERFECT BLEND OF COMFORT, STYLE, AND LOW-MAINTENANCE LIVING. FEATURING SPACIOUS LIVING AREAS, A WELL-APPOINTED KITCHEN, AND A SERENE SCREENED-IN LANAI, IT'S IDEAL FOR RELAXING OR ENTERTAINING. ENJOY RESORT-STYLE AMENITIES INCLUDING A CLUBHOUSE, HEATED POOL, FITNESS CENTER, TENNIS COURTS, AND LAKE ACCESS WITH A PRIVATE DOCK-PERFECT FOR ACTIVE ADULTS 55 AND BETTER! WITH 24-HOUR SECURED GATED ENTRANCE AND A VIBRANT, FRIENDLY ATMOSPHERE. TRADITIONS OFFERS THE LIFESTYLE YOU HAVE BEEN LOOKING FOR. SCHEDULE YOUR PRIVATE TOUR TODAY AND EXPERIENCE FLORIDA LIVING AT ITS FINEST.

3923 Baldwin Lane, Winter Haven

2817 Wingfoot Court, Winter Haven
$270,000
3 Beds ⋅ 2 Baths ⋅ Cypresswood Golf Villas Gc-2 SubDv. ⋅ 33884 Zip Code
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 and airy atmosphere. The eat-in kitchen is a standout with new custom cabinetry, granite countertops, and a convenient closet pantry. Flooring throughout the home includes durable laminate and ceramic tile, with cozy carpeting in the third bedroom. The primary suite offers sliding doors to the patio, a generous walk-in closet, and an updated bathroom. The secondary bedroom also includes a walk-in closet, while the third bedroom features patio access and a European-style A/C unit. Major updates include a roof replacement in 2022, and a new A/C system installed in 2019. Covered parking adds convenience. Enjoy resort-style living with scenic golf course views and access to community amenities, all just minutes from shopping, dining, and major roadways. Whether you're seeking a year-round residence or a seasonal escape, this villa is the perfect place to call home. Community pool, tennis, clubhouse & restaurant.

2817 Wingfoot Court, Winter Haven

4612 Reynosa Drive Sw, Winter Haven
$305,000
3 Beds ⋅ 2 Baths ⋅ Plaza Sub SubDv. ⋅ 33880 Zip Code
Short Sale. BACK ON THE MARKET WITH A BANK-APPROVED SHORT SALE PRICE! Don’t miss the opportunity to own this one-of-a-kind, 3-bedroom, 2-bathroom, 2-car garage custom home. Upon arriving at the property, you are greeted by an oversized lot and mature trees in a quiet, well-established neighborhood. Inside, the home offers an open and split floor plan, cathedral ceilings, and an indoor/outdoor pool that flows from the back patio into the living room, adding a unique feature to this property—perfect for entertaining and allowing you to take a dip in any weather. On the left side of the home are two spacious bedrooms with large closets and a shared bathroom featuring a single vanity and a shower/tub combo. Moving to the right side of the house, you’ll find the master suite, loft, and kitchen. The master suite offers ample space and direct access to the pool area. The en-suite bathroom includes a garden tub and walk-in shower. The loft overlooks the living room and pool area and also contains two large storage spaces on either side, making storage accessible while serving as a great spot to watch a show and unwind. The kitchen features tile countertops and a small bar for additional seating. Right out back, the pool is enclosed in a full-screen cage with a large deck. The yard also boasts a shed for storage and plenty of space for activities. This home has so much to offer. Don’t wait—schedule your private showing today!

4612 Reynosa Drive Sw, Winter Haven

1540 N Lake Mirror Drive Nw, Winter Haven
$899,000
3 Beds ⋅ 3 Baths ⋅ Mirro Mac SubDv. ⋅ 33881 Zip Code
Under contract-accepting backup offers. Virtually Staged. Mid-century modern lakefront pool home on the beautiful Winter Haven Chain of Lakes! Welcome to The Guest House, a rare Mid-Century Modern residence designed and built by internationally recognized architect Gene Leedy. Quietly tucked away at the end of a cul-de-sac on the crystal-clear waters of Lake Mirror, the setting feels surprisingly hidden despite being just minutes from shopping, dining, and convenient access to Lakeland, the Polk Parkway, and Interstate 4 for an easy commute between Tampa and Orlando. Originally commissioned for Thelma Guest, "The Guest House" is a striking example of Leedy’s signature architectural style, blending precast concrete construction, dramatic cantilevered forms, walls of glass windows and doors, deep overhangs, and natural light in a way that still feels timeless today. From the street, the design sits perfectly among mature trees and lush landscaping, setting the stage for what awaits inside. The layout was thoughtfully designed around openness, symmetry, and connection to the outdoors. A towering two-story glass entry and interior atrium create an immediate architectural focal point, while the open staircase and original vintage elevator add both character and functionality between levels. The main living spaces are positioned upstairs to maximize natural light and elevated lake views, with expansive glass overlooking the pool, shoreline, and towering oaks draped in Spanish moss. Nearly every upstairs bedroom and living area opens onto long covered balconies, creating seamless indoor and outdoor living. Downstairs offers an entirely different experience with additional flexible living areas surrounding the central atrium and opening directly to the lakefront grounds and pool area . The heated salt-filtered pool feels perfectly integrated into the original architecture, framed by Leedy’s iconic double “T” beam design and expansive covered patios that naturally extend the living space outdoors. The clean geometry, broad overhangs, and shaded entertaining areas create a resort-like atmosphere that feels both private and connected to the lakefront setting. The property itself offers direct frontage on beautiful Lake Mirror , known for its clear water, scenic shoreline, and access to the larger Winter Haven Chain of Lakes — a connected system of more than 20 lakes popular for boating, skiing, fishing, waterfront dining, and exploring by water. A lightly used public boat ramp located immediately next door makes launching effortless without sacrificing usable shoreline space on the property itself. Additional highlights include solar panels, tasteful modern updates, integrated storage and closet systems true to the Mid-Century aesthetic, two covered carports, circular drive, low-maintenance landscaping, and no HOA restrictions. Rarely does a home combine architectural significance, true Chain of Lakes waterfront living, privacy, and Central Florida convenience in such a compelling way. The Guest House is more than a lakefront residence — it is a piece of Winter Haven architectural history.

1540 N Lake Mirror Drive Nw, Winter Haven

104 Woden Way, Winter Haven
$379,000
3 Beds ⋅ 2 Baths ⋅ Valhalla SubDv. ⋅ 33884 Zip Code
Valhalla - A GATED subdivision with pool, club house and more! 3-bedroom, 2-bath villa home with a connecting property but considered a single family home. This special villa has a functional layout with updated features throughout. A screened entry with leaded glass doors opens to vaulted ceilings and custom architectural touches. The open concept kitchen includes granite countertops, custom cabinetry, a center island with breakfast bar, Bosch dishwasher, stainless oven and range, walk-in pantry, and a passthrough to the living area for open flow. Wood plank flooring runs throughout the main spaces. The living room features large windows and an adjacent flex space for dining, office, or den use. The primary suite includes an ensuite bathroom with slate tile, jacuzzi tub, glass shower, dual sinks, and the laundry room is part of the primary. The guest room features a window seat and recessed lighting. A third room functions well as an office or additional guest space. HOA covers lawn care, water, trash, basic cable, pool, and tennis access.

104 Woden Way, Winter Haven

4099 Island Lakes Drive, Winter Haven
$379,000
3 Beds ⋅ 2 Baths ⋅ Island Lakes SubDv. ⋅ 33881 Zip Code
One or more photo(s) has been virtually staged. NEW ROOF 2/9/2026 + $10K PRICE IMPROVEMENT on 7/24! Now offered at another improved price, this waterfront home on Lake Rochelle delivers the best value currently available on the Winter Haven Chain of Lakes. Located in the desirable Island Lakes community, this well-maintained 3-bedroom, 2-bath home combines lakefront living, major recent updates, and everyday functionality. A brand new roof was installed in February 2026, offering added peace of mind and potential insurance advantages for the next owner. Fresh landscaping and new sod create excellent curb appeal, while the open split-bedroom floorplan provides comfortable living with beautiful natural light throughout. The spacious primary suite overlooks the water and includes a private bath and walk-in closet. The living and dining areas flow easily into the kitchen, making the home ideal for entertaining, weekend guests, or simply enjoying the lake lifestyle. Step outside and enjoy direct access to the Chain of Lakes with boating, fishing, kayaking, and sunset views right from your backyard. Conveniently located near shopping, dining, medical facilities, and major roadways while still offering a peaceful waterfront setting. Whether you’re looking for a primary residence, winter retreat, or investment opportunity, this property checks all the boxes for Florida lakefront living. Schedule your private showing today.

4099 Island Lakes Drive, Winter Haven

1787 White Elephant Loop, Winter Haven
$279,900
3 Beds ⋅ 2 Baths ⋅ Peach Crossings SubDv. ⋅ 33884 Zip Code
NO CDD fees! Welcome to Peach Crossings, Winter Haven’s newest community! This brand-new three-bedroom, two-bathroom home is designed for both comfort and style. The kitchen is the heart of the home, offering ample counter space—perfect for meal prep and entertaining. It comes fully equipped with Whirlpool stainless steel appliances, including a refrigerator, stove, dishwasher, and microwave—all included at no extra cost! Granite countertops and modern cabinetry provide a classic, elegant touch. This home also features high ceilings, enhancing the open and airy feel throughout the living spaces. Enjoy the outdoors year-round with the covered patio, a great spot for dining, relaxing, and taking in the fresh air—made even better by the privacy of having no rear neighbors and a beautiful pond view. This home is packed with energy-efficient features, such as double-pane windows, a programmable thermostat, coach lighting, and a Wi-Fi-enabled garage door opener for added convenience. A mudroom off the garage offers the perfect drop zone for shoes, bags, and coats, making daily routines easier. Located next to the laundry room, this space helps keep everything organized and clutter-free. Situated in Polk County, Peach Crossings offers a balance of peaceful lake life and easy access to shopping, dining, and major attractions. Families will love the top-rated Polk County schools, and the community features a playground and picnic area for all to enjoy. Don’t miss out on this incredible opportunity—schedule your tour today!

1787 White Elephant Loop, Winter Haven

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