Location: Winter Haven
Do Not Show Listings
2642 RUTLEDGE CT, WINTER HAVEN, FL 33884
$199,90016 Days on yellowkey MLS ID: A4688023
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1419 Built: 2006 Tax: $1,794 (2024)Community: Traditions Ph 01Townhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,794
Elementary School: Chain O Lakes Elem
High School: None
Tax Year: 2024
Middle School: Mclaughlin Middle
Remarks: Light and bright 2/2/1 in The Verandah's at Lake Reeves. The Verandahs offers a community pool and fishing dock on Lake Reeves. The low HOA fee includes ground maintenance, basic cable and internet, exterior painting and more. Easy access to shopping, Legoland, chain of lakes. Light and bright, move in ready. Dual master bedroom set up. Den/office off of main living area. Vaulted ceilings, large kitchen, open living plan.
Listing is courtesy of: FLATFEE.COM (954-965-3990)
Listing Agent: Cliff Glansen
196 DURRELL CIR, WINTER HAVEN, FL 33884
$215,00016 Days on yellowkey MLS ID: O6393488
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1402 Built: 1973 Tax: $3,359 (2025)Community: Fla Highlands Co SubSingle Family
Taxes:$3,359
Elementary School: Garden Grove Elem
High School: Winter Haven Senior
Tax Year: 2025
Middle School: Denison Middle
Remarks: This 3-bedroom, 2-bathroom home located in the Florida Highland Co neighborhood. This residence offers a classic and straightforward layout that provides a comfortable living environment for a variety of lifestyles. The heart of the home features a kitchen equipped with a mix of black and white appliances, complemented by durable laminate countertops that offer plenty of workspace for daily meal preparation. The interior transitions smoothly between living areas, maintaining a functional sense of space throughout. Situated in a convenient location, this property offers easy access to local amenities and major regional hubs, ensuring a simplified commute for those working in the surrounding areas. Schedule your private showing today!
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
103 MORNING GLORY CIR, WINTER HAVEN, FL 33884
$319,90016 Days on yellowkey MLS ID: TB8489377
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2021 Built: 1996Monthly Fee: $160 Tax: $1,677 (2025)Community: MorningsideSingle Family
Taxes:$1,677
High School: Lake Region High
Remarks: Welcome to 103 Morning Glory Circle in the highly desirable Morningside at Winterset community in Winter Haven. As you step inside, you’ll be greeted by soaring vaulted ceilings, abundant natural light, neutral paint tones and immense charm. The spacious living room is the heart of the home, featuring a cozy fireplace and custom built-in shelving, creating the perfect space to relax or entertain. The home’s layout flows seamlessly, offering both functionality and style, while the tile roof adds durability and long-term value. New HVAC was installed in 2025 and water heater in 2020 along with all new appliances within the last few years. Step outside to your large screened-in patio, ideal for enjoying Florida’s outdoor lifestyle year-round, whether you’re hosting guests or unwinding in your private retreat. Located in a gated community with low HOA and no CDD, homeowners of Morningside at Winterset enjoy access to resort-style amenities including a community pool, clubhouse, tennis courts, private-community boat ramp, and direct lake access to Lake Winterset, perfect for boating, fishing, and soaking up the Florida sunshine. Conveniently situated near LEGOLAND Florida Resort, the Chain of Lakes, shopping, dining, medical facilities, and major highway access, this home offers the perfect blend of peaceful living and everyday convenience. If you’ve been searching for a home that combines character, community, and location, this one checks all the boxes. Schedule your showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Eric Gross (513-907-4271)
1518 FUJI CT, WINTER HAVEN, FL 33881
$285,90079 Days on yellowkey MLS ID: TB8468713
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1537 Built: 2023Monthly Fee: $92 Tax: $3,746 (2025)Community: Lake Lucerne IiSingle Family
Taxes:$3,746
Elementary School: Lake Alfred Elem
High School: Haines City Senior High
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: Discover resort-style living in this charming 3-bedroom, 2-bath home built in 2023, nestled in the amenity-rich Villages at BridgeWater community. Boasting 1,537 sq ft of modern comfort on a 5,998 sq ft lot, enjoy an open floor plan with vaulted ceilings, a modern kitchen with large island, and a private primary suite. Community perks include a pool, fitness center, tennis courts, and a playground – perfect for families! Convenient to US-27, shopping, and top employers. Low HOA includes cable/internet. Move-in ready for your Florida lifestyle!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: John Crusinberry (813-815-2535)
1347 OAKMONT DR, WINTER HAVEN, FL 33884
$384,90024 Days on yellowkey MLS ID: L4960249
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1712 Built: 2020Monthly Fee: $5 Tax: $3,921 (2025)Community: Lake Ashton West Ph 2 SouthSingle Family
Taxes:$3,921
Elementary School: None
Middle School: None
Remarks: Are you looking for a move-in ready home? Well, you found it! This home is like a new build, only better. It is clean as a whistle, has tasteful lighting and fans, luxury plank vinyl, granite countertops, screened lanai, retractable screens on the garage, epoxy garage floor, pad for a grill outback, only naming a few. This is an open floor plan that is great for either entertaining or hanging out at home by yourselves. The home was built in 2020 so it was designed to be eco friendly which makes it easier on the pocketbook. The master has an ensuite bath and a large walk in closet. The two additional bedrooms are a comfortable size for guests. One of the rooms has 3 windows that bow out which allows in lots of natural light, not to mention the bit of extra floor space it adds. It is a perfect space for a desk should you choose to make this your office. All this plus the fact that it is in one of Florida's premier Active Adult Communities. There are two 24 hr manned entrances, 2 pools & hot tubs, billiard rooms, craft rooms, computer libraries, bowling alley, movie theater, 3 dog parks, golf course, pro shop, dances, entertainment and too many clubs and activities to mention. You can be as active or involved as you like. Live and mingle among folks you may have a lot in common with and many of the same interests.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Ann Heaton (407-758-1472)
235 6TH ST NW #307, WINTER HAVEN, FL 33881
$125,000162 Days on yellowkey MLS ID: P4936842
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 714 Built: 1982 Tax: $1,976 (2025)Community: The HavenCondo
Taxes:$1,976
Elementary School: Lake Shipp Elem
Remarks: One or more photo(s) has been virtually staged. Downtown Winter Haven condo located in one of Winter Haven’s most iconic hotels, The Haven. This residence has been transformed into boutique historic condos just steps from downtown, Lake Howard, restaurants, coffee shops, nightlife, parks, and the popular Saturday Farmers Market. With its blend of vintage charm, modern updates, and low-maintenance living, this 1-bedroom, 1-bath unit is ideal for first-time buyers, investors, seasonal residents, or anyone seeking an affordable condo with great rental potential. Located on the 3rd floor, the residence features tall ceilings, large windows, and bright natural light with elevated views of downtown. The updated kitchen offers granite countertops, brand-new stainless steel appliances, and dual pantry/utility closets—perfect for maximizing storage in a condo setting. The spacious primary bedroom boasts oversized historic windows, a walk-in closet, and room for a king-sized bed. The bathroom has been refreshed with granite counters, a tiled tub surround, and a traditional tub/shower combo. The Haven provides sought-after condo amenities, including secure key-fob access, elevators, a community pool, assigned parking, on-site laundry, additional storage rooms, and a beautifully restored historic lobby. Residents also enjoy a private pool courtyard surrounded by lush landscaping, creeping fig walls, palm trees, and peaceful lounging areas—ideal for relaxation or working remotely outdoors. This walkable location offers the best of downtown Winter Haven living. Enjoy immediate access to dining, shopping, entertainment, and lakefront walking paths. With 50 lakes—including the world-famous Winter Haven Chain of Lakes—you’re minutes from boating, fishing, skiing, and sunset views. Everyday conveniences like Publix, Walmart, Aldi, TJ Maxx, medical facilities, and LEGOLAND Florida Resort are all close by. If you’re looking for an affordable, updated, low-maintenance condo with historic character and the convenience of downtown living, this stylish unit at The Haven checks every box.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Michael Stone (863-412-9733)
3410 FOX RIDGE ST, WINTER HAVEN, FL 33884
$275,00062 Days on yellowkey MLS ID: P4937797
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1369 Built: 1986 Tax: $1,686 (2025)Community: Fox Ridge Ph 02Single Family
Taxes:$1,686
Remarks: Welcome to 3410 Fox Ridge Street in Winter Haven, FL. This 3-bedroom 2 bath home features tiled flooring throughout, new appliances, new interior and exterior paint. Granite countertops in kitchen and bathrooms. Open floor plan with a wood burning fireplace. Inside laundry room. Master bedroom features his and her walk-in closets. The home is within walking distance of Garden Grove elementary school. Minutes from Legoland, shopping , medical facilities and many dining options. No HOA in this community. Easy access to major highways and located in between Tampa and Orlando. This home has much to offer. Schedule your appointment today!
Listing is courtesy of: THE HOME COMPANY (863-268-8157)
Listing Agent: Sue Ann Williamon (863-258-3115)
5850 CYPRESS GARDENS BLVD #302, WINTER HAVEN, FL 33884
$149,50019 Days on yellowkey MLS ID: P4938197
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1332 Built: 1975 Tax: $1,683 (2025)Community: Royal Crescent CondoCondo
Taxes:$1,683
Remarks: Welcome to this charming and updated, move-in ready 2-bedroom, 1.5-bath condo nestled right on Cypress Gardens Blvd in Winter Haven — just minutes from world-class shopping, dining, and the famous LEGOLAND Florida Resort! This well-maintained two-story unit has been tastefully updated throughout. Rich dark luxury vinyl plank flooring flows through the spacious living areas, giving the home a modern, cohesive feel. The kitchen is fully equipped with rich wood cabinetry, stainless steel appliances including a dishwasher, range, and refrigerator, and tile flooring — with a sliding glass door that brings in great natural light. A convenient half bath on the main level is fully updated with a new vanity and brushed nickel fixtures. Upstairs you'll find two generously sized bedrooms. The dedicated laundry closet plumbed and ready for your washer and dryer is on the first floor. The classic brick exterior and covered front porch add great curb appeal and a welcoming first impression. Whether you're a first-time buyer, downsizer, or investor looking for a rental in a high-demand location, this one checks all the boxes. Schedule your showing today — this one won't last!
Listing is courtesy of: HAVEN REALTY & INVESTMENTS (863-333-5053)
Listing Agent: Vincent Reina (863-398-6243)
1586 MARTIN LUTHER KING BLVD NE, WINTER HAVEN, FL 33881
$675,000163 Days on yellowkey MLS ID: L4957040
0 Days Off yellowkey (back on 3/30/2026)
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2493 Built: 2023 Tax: $4,242 (2024)Community: Buckeye HeightsSingle Family
Taxes:$4,242
Remarks: Under contract-accepting backup offers. Welcome to 1586 Martin Luther King Blvd NE, Winter Haven, FL 33881—an exceptional custom-built residence completed in 2022 that seamlessly blends refined elegance with modern innovation. Nestled on a beautifully landscaped half-acre lot, this stunning home offers 4 bedrooms, 3 bathrooms, and a private office with French doors, encompassing 2,493 square feet of thoughtfully designed living space. The property is privately gated with a Ghost Controls automatic gate and Remootio remote access, surrounded by lush clumping bamboo that creates a natural living fence along both the front and rear property lines for serene privacy. Step inside to soaring 10-foot ceilings, elegant trey details, and custom wood beams accenting both the great room and primary suite. Every detail of this home has been carefully curated, from the insulation-injected block construction to the seamless integration of style, comfort, and technology. The heart of the home—the kitchen—is a showpiece of sophistication. Designed for both functionality and visual impact, it features striking quartz countertops, a spacious center island perfect for entertaining, and beautiful display cabinets that elevate the overall aesthetic. Under-cabinet and accent lighting illuminate the rich finishes, while all stainless-steel appliances add a sleek, modern touch. The open layout flows effortlessly into the great room and dining area, creating an inviting environment for gatherings large and small. Retreat to the luxurious primary suite, where craftsmanship and comfort meet. The spa-inspired bathroom features a freestanding soaking tub elegantly positioned within the walk-in shower, surrounded by high-end finishes. Custom closet systems throughout the home ensure both form and function are beautifully balanced. Outdoor living is equally impressive, with front and rear porches finished in tongue-and-groove ceilings that exude timeless charm. The property’s lush, fully irrigated lawn—fed by a dedicated shallow well and managed via a Hydrawise smart controller—is enhanced by thoughtful landscape lighting and buffered plantings for added seclusion. Sustainability and innovation define this home’s infrastructure, including 32 solar panels paired with dual Tesla Powerwall 3 whole-home backup batteries, a Tesla Level 2 wall charger, and a Kinetico whole-home water filtration and softening system. The residence also includes custom driveway, and a fully operational chicken coop. With no HOA and an enviable location in the heart of Winter Haven—renowned for its scenic chain of lakes—this exquisite property offers a rare opportunity to own a modern luxury estate designed for comfort, privacy, and sustainable living. Experience elegance redefined at 1586 Martin Luther King Blvd NE. Schedule your private tour today.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Christine Hubbert (863-370-4915)
341 STERLING DR, WINTER HAVEN, FL 33884
$389,50099 Days on yellowkey MLS ID: L4958307
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2008 Built: 1991Monthly Fee: $24 Tax: $4,432 (2024)Community: BerryhillSingle Family
Taxes:$4,432
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Experience refined living in this beautifully renovated residence designed for both elegance and comfort. This exceptional 4-bedroom, 3-bath home has a newer roof and AC as well as featuring a desirable split floor plan, soaring ceilings in select areas, and an abundance of natural light that enhances the home’s open, airy feel. The designer kitchen is a true showpiece, appointed with all-new custom cabinetry, sleek quartz countertops, premium appliances, and an expansive peninsula ideal for upscale entertaining and casual dining alike. Luxury vinyl flooring flows seamlessly throughout, complemented by new designer fans, fixtures, and finishes. The primary suite serves as a private retreat, offering a spacious walk-in closet and a spa-inspired en-suite bath with double vanities and an oversized walk-in shower. A second en-suite bedroom provides the perfect guest or multi-generational suite, thoughtfully positioned for privacy. Step outside through two sets of sliding glass doors to your own resort-style oasis. The covered lanai overlooks a private, fully screened swimming pool with an in-ground spa, creating the ultimate setting for relaxation and outdoor entertaining. The fully fenced backyard enhances privacy while maintaining a serene atmosphere. Additional highlights include an indoor laundry room, an attached two-car garage, and an oversized driveway providing ample parking. This move-in-ready home offers sophisticated finishes, functional design, and luxurious indoor-outdoor living.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
1731 AVENUE C NE, WINTER HAVEN, FL 33881
$380,000145 Days on yellowkey MLS ID: S5138718
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1619 Built: 1952 Tax: $2,668 (2025)Community: Elbert AcresSingle Family
Taxes:$2,668
Elementary School: Elbert Elem
High School: Chain of Lakes Collegiate High
Middle School: Westwood Middle
Remarks: Exclusive property in Winter Haven featuring a 4-bedroom main home, private pool, independent studio, and parking for up to 6 cars. Located in a peaceful and welcoming city known for its beautiful lakes and excellent quality of life, this property offers comfort, space, and great potential. The main house includes 4 spacious bedrooms, 2 beautifully updated bathrooms, a fully renovated kitchen with an island and pool views, open-concept living and dining areas, and bright, inviting spaces throughout. Enjoy your own private pool, perfect for relaxation and entertainment. The independent studio is ideal for rental income, guests, or family use, and offers an integrated living/sleeping area, a full kitchen with stove, microwave, and dishwasher, a private bathroom, and its own laundry space. Conveniently located between Orlando and Tampa, Winter Haven provides access to numerous lakes for recreation and water sports, a quiet and safe community, and proximity to schools, shopping, dining, and essential services. Don’t miss this unique opportunity—schedule your visit today!
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Paola Millan (407-452-7034)
271 INMAN BLVD, WINTER HAVEN, FL 33881
$350,000131 Days on yellowkey MLS ID: W7881213
Bed: 5 Bath: 2.5 Liv Area Sq Ft: 2274 Built: 2024Monthly Fee: $49 Tax: $1,347 (2024)Community: Inman GrovesSingle Family
Taxes:$1,347
Remarks: PRISTINE AND MOVE-IN READY! Seller is offering up to $5,000 concession towards closing costs and prepaids. Come and see this barely lived in 5 BEDROOM, 2.5-BATH home nestled in the solar-friendly community of INMAN GROVES. Built in 2024 and set on a corner lot with NO REAR NEIGHBORS, this home offers peaceful views, unbeatable privacy, and all the advantages of brand-new construction—without the wait. Step inside and be greeted by a bright and open first floor layout designed for effortless living and entertaining. The spacious great room flows seamlessly into the stunning kitchen, featuring QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES, A LARGE CENTER ISLAND, SPACIOUS PANTRY, and ABUNDANT CABINET SPACE. The adjacent dining area makes gathering and conversation feel natural and inviting. A HALF BATH and INSIDE LAUNDRY ROOM add everyday convenience. Upstairs, a VERSATILE LOFT offers the perfect second living space ideal as a TV lounge, playroom, homework hub, or home office. Tucked away in its own private corner is the PRIMARY BEDROOM, complete with an oversized WALK-IN CLOSET and spa-inspired en-suite bathroom with DUAL SINKS, QUARTZ VANITY, and an elegant WALK-IN TILE SHOWER. FOUR SPACIOUS SECONDARY BEDROOMS are thoughtfully arranged around a full bathroom with dual sinks, making room for everyone. Step outside to your FENCED BACKYARD, where a patio awaits—perfect for grilling, lounging, and enjoying Florida’s year-round sunshine. Enjoy low utility costs with your energy-efficient SOLAR PANELS leased at only $93/month. Home is located just off Dundee Road and gives you quick access to Hwy 27, Hwy 17 and Polk Parkway, theme parks like Legoland, Disney and Universal. Close to Winter Haven downtown, hospitals, restaurants, breweries, Chain of lakes and Florida beaches. With contemporary design, energy savings, and an unbeatable location, this home checks every box. Don’t miss your chance to make 271 Inman Blvd your New Haven—schedule your private showing today!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (352-688-2227)
Listing Agent: Isabelle Maye (540-840-8849)
3111 LAUREL OAK LN, WINTER HAVEN, FL 33884
$307,90068 Days on yellowkey MLS ID: L4959234
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1857 Built: 2025Monthly Fee: $18Community: VillamarSingle Family
Taxes:$0
Remarks: New construction home with 1857 square feet on one-story including 4 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty ***Please note - Virtual Tour/Photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey!
Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)
Listing Agent: George Lindsey, Iii (863-797-4999)
5355 MICKEY AVE, WINTER HAVEN, FL 33884
$339,950134 Days on yellowkey MLS ID: S5139501
1 Days Off yellowkey (back on 3/6/2026)
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2077 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Remarks: This thoughtfully designed Slate home opens with two bedrooms flanking a full hall bath. Beyond the entry, you’ll find an open layout with a dining nook, a great room with access to an inviting covered patio, and a kitchen with a center island, walk-in pantry and abundant cabinetry. The owner’s suite is nearby, offering a generous walk-in closet and a private bath with a shower and a separate soaking tub. A laundry room and a fourth bedroom with its own private bath complete the home. Features include; 9"4' ceilings and 8' doors, 42' cabinets, white quartz counter tops in the kitchen, ceramic tile throughout the wet and main living areas of the home. All bedrooms, family room, and covered lanai are prewired for ceiling fans. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $25,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Stephanie Morales, Llc (407-399-2055)
530 SANCTUARY BLVD, WINTER HAVEN, FL 33881
$639,90053 Days on yellowkey MLS ID: S5144344
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 3619 Built: 2023Monthly Fee: $83 Tax: $7,594 (2025)Community: Sanctuary By The Lake Ph OneSingle Family
Taxes:$7,594
High School: Auburndale High School
Remarks: Welcome to this exceptional custom-built 2023 luxury residence located within the gated community of Sanctuary by the Lake, where modern elegance, thoughtful design, and everyday comfort come together seamlessly. Perfectly positioned on a spacious corner lot directly across from the lake, this stunning home immediately impresses with its commanding presence and refined architectural detail. Step through the beautiful double front doors and experience an immediate sense of openness, highlighted by soaring ceilings, abundant natural light, and expansive living spaces designed to feel both grand and inviting. With over 3,600 square feet of living space, the thoughtfully designed open layout effortlessly connects formal and casual living areas, creating an ideal setting for both entertaining and relaxed daily living. At the heart of the home lies a beautifully appointed chef’s kitchen, featuring granite countertops, upgraded stainless steel appliances, a breakfast bar, walk-in pantry, and generous prep space, perfect for hosting gatherings or enjoying quiet mornings at home. The kitchen flows naturally into the impressive great room and dining areas, enhancing the home’s seamless indoor living experience. One of the standout features is the oversized covered and enclosed Florida room, custom added by the owners to extend the living space year-round. Whether hosting celebrations, entertaining guests, or simply unwinding while enjoying peaceful surroundings, this space truly elevates the lifestyle this home offers. Designed with privacy in mind, the desirable triple split floor plan includes 4 spacious bedrooms, 3 full bathrooms, and a dedicated private office, ideal for remote work or flexible living needs. The luxurious primary suite serves as a private retreat, complete with dual vanities, a garden tub, separate walk-in shower, makeup vanity, and a very generous walk-in closet. Beautiful luxury vinyl plank flooring flows throughout the main living areas, complemented by tasteful finishes and quality craftsmanship that reflect the home’s custom construction. A well-equipped laundry room with cabinetry, countertop workspace, and sink adds everyday convenience. A 50 amp generator port was added for peace of mind. Beyond the home itself, the location offers the best of Central Florida living. Just minutes from downtown Winter Haven, residents enjoy award-winning restaurants, local boutiques, parks, and year-round entertainment, while nearby access to Lakeland and I-4 provides an easy commute to both Tampa and Orlando. Florida’s Atlantic and Gulf beaches are approximately 90 minutes away, making weekend coastal escapes effortlessly accessible. This is more than a home, it is a refined living experience combining space, luxury, and lifestyle within one of Winter Haven’s most desirable gated communities.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
2202 GARDEN LAKE DR, WINTER HAVEN, FL 33884
$249,000110 Days on yellowkey MLS ID: P4937345
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2000Monthly Fee: $230 Tax: $3,336 (2025)Community: Richmond Square SubSingle Family
Taxes:$3,336
Remarks: Experience resort-style living in the prestigious gated community of Winterset, just minutes from Legoland. This captivating 3-bedroom, 2-bath villa, featuring Mediterranean-inspired architecture, offers the perfect blend of elegance, comfort, and tranquility. Upon arrival, you’re welcomed by a charming covered screened porch accented with a leaded glass entry door, setting the tone for the inviting interior. The thoughtfully designed split-bedroom floor plan includes a spacious great room highlighted by a wood-burning fireplace, a decorative built-in media center, and glass sliders that open to the Florida room—seamlessly blending indoor and outdoor living. Easy-to-maintain solid surface flooring flows throughout the home. The well-appointed kitchen showcases white cabinetry with crown molding, an upgraded stainless steel appliance package including a gas range and beverage cooler. Granite countertops that adorn the expansive breakfast bar and a double-bowl sink with a gooseneck faucet adds both style and functionality. The open-concept layout is ideal for entertaining, with the formal dining room flowing effortlessly into the living area. The primary bedroom suite serves as a luxurious retreat, featuring laminate flooring, a spacious walk-in closet, and a glass slider providing private access to the Florida room. The primary bathroom offers a granite-topped vanity, upgraded brushed nickel fixtures, a comfort-height toilet, and a tub/shower combination with a decorative tile surround. Both guest bedrooms are generously sized and include walk-in closets, providing ample storage. Outdoor living is elevated with an extended Florida room offering peaceful pond views—an ideal space to relax and unwind. Additional Features: Laundry room with washer and dryer, New ceiling fans throughout with remote controls, new water heater, Updated AC system (2021), Epoxy-finished flooring in the Florida room and garage, Exterior carriage lighting, Gutters, Tile roof, One-car garage with garage door opener. The Winterset community offers an exceptional array of amenities, including a lakefront clubhouse, tennis courts, shuffleboard, a heated pool, hot tub, and access to Lake Winterset, part of the renowned Winter Haven Chain of Lakes. HOA fees include exterior maintenance, grounds maintenance, security, and access to community amenities, ensuring truly carefree living. Conveniently located near shopping, dining, medical facilities, and entertainment, this villa provides a lifestyle defined by luxury, comfort, and convenience.
Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)
Listing Agent: Eileen Belanger (863-221-0229)
4507 RAPALLO AVE, WINTER HAVEN, FL 33884
$302,90068 Days on yellowkey MLS ID: L4959233
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1754 Built: 2025Monthly Fee: $18Community: VillamarSingle Family
Remarks: Move-in ready 4-bedroom home for sale! A Craftsman-style front porch welcomes you into the fully open living area featuring airy volume ceilings and sunny natural lighting. Unwind in your private owner's suite complete with a large walk-in wardrobe and a private en-suite bath with dual vanities, a tiled glass-enclosed shower, private toilet, and a linen closet. Plus, enjoy outdoor living on your front porch and screened-in lanai! This home includes features and finishes hand-selected by our professional designers to provide you with enduring style, move-in convenience, and easy home maintenance: Well-appointed kitchen with: A counter-height island. Quartz countertops. 36-in shaker-style cabinets with crown moulding and decorative knobs/pulls. Stainless steel undermount sink with a pull-down faucet. Walk-in pantry. Samsung stainless steel appliances: 5-burner smooth-top electric range with wi-fi smart controls. Fingerprint-resistant microwave with ventilation system. ENERGY STAR(R) quiet-operation dishwasher. ENERGY STAR(R) large capacity side-by-side refrigerator. . Dining space at the island and the adjacent cafe. . Low-maintenance luxury vinyl plank flooring throughout the entire home. Convenient drop zone at the garage entry. Energy-efficient LED lighting in the kitchen and gathering room. Custom-fit 2-in. faux wood window blinds . Built-in pest control. Architectural shingles with a limited-lifetime warranty. Fully sodded homesite with Florida-friendly landscaping and an irrigation system. ... and much more!. Save on utilities with energy-efficient R-30 insulation, foam-injected block insulation, double-pane Low-E windows, and a programmable thermostat. Call or email us today!
2735 RUTLEDGE CT, WINTER HAVEN, FL 33884
$220,00091 Days on yellowkey MLS ID: TB8462826
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1419 Built: 2006Monthly Fee: $250 Tax: $1,639 (2025)Community: Traditions Ph 01Townhouse
Taxes:$1,639
Remarks: Under contract-accepting backup offers. Move-in-ready, one-story townhome is now available in the highly sought-after Verandahs at Lake Reeves community. This well-maintained home offers 2 spacious bedrooms and 2 full bathrooms, plus a large bonus room that can be used as an office, den, or potential third bedroom. The kitchen features solid wood cabinetry, solid surface countertops, and ample space for cooking and entertaining. High ceilings and an open floor plan create a bright, airy atmosphere throughout the home. Enjoy relaxing on the screened lanai overlooking peaceful community greenspace. Residents of The Verandahs enjoy access to a community pool and fishing pier on scenic Lake Reeves. The low monthly HOA covers internet, cable, and lawn maintenance—so you can stay cool and carefree in the Florida sunshine. Furnture can be included with purchase if buyer has interest in it. Major updates include a new roof in 2018, along with a recently replaced water heater and dryer. Simply move in and start enjoying the Florida lifestyle.
Listing is courtesy of: KELLER WILLIAMS TAMPA PROP. (813-264-7754)
Listing Agent: Cynthia Kladakis (813-415-7277)
252 MEREDITH BLVD, WINTER HAVEN, FL 33881
$289,99017 Days on yellowkey MLS ID: G5110266
0 Days Off yellowkey (back on 3/29/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1758 Built: 2025Monthly Fee: $6 Tax: $500 (2024)Community: WillowbrookSingle Family
Taxes:$500
Elementary School: Fred G. Garnier Elem
Remarks: One or more photo(s) has been virtually staged. Hillcrest floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1,758 square feet of living space and provides excellent curb appeal in its elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
4622 CYPRESS GARDENS RD, WINTER HAVEN, FL 33884
$180,00018 Days on yellowkey MLS ID: S5146684
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1706 Built: 1985 Tax: $3,238 (2025)Community: Silver Oaks VillasSingle Family
Taxes:$3,238
Remarks: Welcome to this charming and versatile 2-bedroom, 2-bath home offering 1,706 square feet of living space in Winter Haven. This property features a spacious combined living and dining area, ideal for both everyday living and entertaining. The home also offers a flexible bonus room that can easily be converted into a third bedroom, home office, hobby space, or guest area, along with a bright sunroom at the back—ideal for relaxing and enjoying backyard views year-round. Step outside to a screened-in back porch, ideal for unwinding or outdoor dining, and take advantage of the backyard shed for additional storage. With its adaptable spaces and inviting indoor-outdoor features, this home is a must-see—schedule your private showing today and discover all it has to offer! The home is being Sold in As Is condition without any Warranty nor Guarantee by seller. The buyer is responsible for verifying ALL property information, room sizes, utilities and condition. All buyers must view the home before submitting an offer. HUD CASE: 098-116683 FINANCE ESCROW MAY APPLY FINANCE CODE: IE
Listing is courtesy of: REALTYCITY INC (863-438-6605)
Listing Agent: Jesse Carriedo (863-438-6605)
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