Displaying: For Sale
Location: Winter Haven
Property Type(s): Single Family
Beds: 3 to 3
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Winter Haven - 324 properties found
1733 SANDALWOOD CIR SW, WINTER HAVEN, FL 33880
$260,00094 Days on yellowkey MLS ID: L4958444
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1075 Built: 1984 Tax: $1,330 (2025)Community: Sandalwood SubSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,330
Elementary School: Lake Shipp Elem
High School: Winter Haven Senior
Tax Year: 2025
Middle School: Westwood Middle
Remarks: Attention Investors & Homeowners! Whether you’re a seasoned investor or looking for a home with built-in income, this property presents an exciting opportunity. This well-maintained 3-bedroom, 2-bath block home is located within Winter Haven city limits and offers 1,155 square feet of tile flooring throughout with no HOA. The home features a functional layout, spacious rooms, ample kitchen counter space, and a large fenced backyard. Major updates include a newer roof (2018), A/C replacement (2014), and a water heater installed in 2004. Currently tenant-occupied, making it a great income-producing option with future flexibility. Conveniently located just minutes from shopping, downtown Winter Haven, and approximately 12 minutes from LEGOLAND. Don’t miss out—schedule your showing today and see the potential for yourself.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Melissa Ramirez (813-956-1071)
1798 WHITE ELEPHANT LOOP, WINTER HAVEN, FL 33884
$298,90080 Days on yellowkey MLS ID: TB8476320
2 Days Off yellowkey (back on 4/6/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1526 Built: 2025Monthly Fee: $90Community: Peach CrossingsSingle Family
Taxes:$0
Elementary School: Pinewood Elem
High School: Lake Region High
Tax Year: 2024
Middle School: Denison Middle
Remarks: Welcome to Peach Crossings, a brand-new community in Winter Haven! This beautiful three-bedroom, two-bathroom home is designed with both comfort and style in mind. The kitchen is a true highlight, featuring expansive counter space, perfect for meal prep and entertaining. It comes fully equipped with Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave—all included at no extra cost! The combination of granite countertops and crisp white cabinetry creates a timeless and elegant look. This home also features high ceilings, enhancing the open and airy feel throughout the living spaces. Enjoy outdoor living on the covered patio, an ideal space for relaxing, dining, or enjoying the Florida weather. This home also comes with energy-efficient features, such as double-pane windows, a programmable thermostat, coach lighting, and a Wi-Fi-enabled garage door opener for modern convenience. A mudroom just off the garage provides a functional space to store shoes, bags, and coats, helping to keep the home organized. Conveniently located next to the laundry room, this area makes everyday tasks easier. Located in the heart of Polk County, Peach Crossings offers the perfect balance of peaceful lake living with easy access to shopping, dining, and local attractions. Families will appreciate the top-rated Polk County schools, and the community features a children’s playground and a picnic area for all to enjoy. Don’t miss this opportunity—schedule your showing today!
Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)
Listing Agent: Gayle Van Wagenen (904-449-3938)
3256 AVENUE M NW, WINTER HAVEN, FL 33881
$205,00098 Days on yellowkey MLS ID: S5142533
0 Days Off yellowkey (back on 4/6/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1097 Built: 2007 Tax: $2,660 (2025)Community: InwoodSingle Family
Taxes:$2,660
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. This charming Winter Haven home offers comfort, functionality, and a convenient location. Featuring a well-designed layout with spacious living areas and natural light throughout, this property is perfect for homeowners or investors alike. The kitchen provides ample cabinet space and flows easily into the main living area, creating an inviting space for everyday living and entertaining. The bedrooms are comfortably sized, and the home offers a functional floor plan ideal for a variety of lifestyles. Situated in a quiet neighborhood, this property is close to shopping, dining, schools, and major roadways, providing easy access to all that Winter Haven has to give. Whether you’re a first-time buyer, downsizing, or looking for an investment opportunity, this home delivers great value and potential.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Phillip Randall (407-202-2096)
5365 HOGAN LN, WINTER HAVEN, FL 33884
$599,90035 Days on yellowkey MLS ID: P4938226
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2591 Built: 2007Monthly Fee: $5 Tax: $5,104 (2025)Community: Lake Ashton West Ph 01Single Family
Taxes:$5,104
Remarks: 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 7½' x 36' bromine pool awaiting your enjoyment. From the striking stone front elevation and bronze screened front entry to the expansive 51' x 13' bronze screened veranda, this home impresses at every turn. Perfectly positioned on a large pond with a nature preserve beyond, it provides delightful sunrise views and frequent sightings of the abundant wildlife that makes Lake Ashton so special. Step inside through the elegant double glass doors and immediately notice the clean, crisp, and welcoming feel that creates the ideal setting for both relaxed everyday living and gracious entertaining. The interior showcases stunning terraced crown molding, coffered ceilings in both the living room and primary bedroom, and five solar tubes that fill the home with abundant natural light. The kitchen is beautifully appointed with gorgeous cabinetry featuring two glass-front cabinets, a wine rack, and rich black granite countertops, complemented by a large walk-in pantry offering generous storage space. Both bathrooms include walk-in showers and granite counters, adding style and convenience. One of the home’s most remarkable highlights is the expansive screened enclosure with pool at the rear of the property, where the views of the pond, wildlife, and nature preserve are among the finest along Hogan Lane. Additional peace of mind comes from an updated air conditioning system and a roof that is only three years old. Residents of Lake Ashton enjoy unmatched amenities including two championship 18-hole golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, theater, pickleball courts, bowling alley, and so much more, creating an active and fulfilling lifestyle. This exceptional property offers the perfect blend of comfort, convenience, and community—schedule your private showing today and experience the very best of Florida living.
Listing is courtesy of: GLOBAL LIFESTYLE LLC (727-455-2709)
Listing Agent: Brad Kirwan (863-280-0390)
221 WHITMAN RD, WINTER HAVEN, FL 33884
$275,00031 Days on yellowkey MLS ID: L4960816
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1511 Built: 1970 Tax: $2,444 (2025)Community: Fla Highlands Co SubSingle Family
Taxes:$2,444
Remarks: Under contract-accepting backup offers. Welcome to this well-maintained 3-bedroom, 2-bathroom home situated on a desirable corner lot in Winter Haven. Conveniently located in the heart of Central Florida, Winter Haven is known for its Chain of Lakes, Legoland, local parks, shopping, dining, and easy access to both Orlando and Tampa. This property offers a functional layout with thoughtful updates throughout. The updated kitchen features quartz countertops, ample dark wood cabinetry, and a convenient breakfast bar. Recent improvements include tile flooring and an upgraded electrical panel, adding both style and peace of mind. The primary bedroom includes a walk-in closet, while the additional bedrooms provide flexibility for a variety of uses. Step outside to enjoy the large screened-in porch, ideal for relaxing or entertaining, all within a fully fenced yard with durable PVC fencing. The irrigation system is controlled by a Hydrawise WiFi system, allowing for easy and efficient lawn maintenance. Additional highlights include a 2-car garage, a circular driveway for added parking and convenience, and a roof replaced in 2018. With no HOA or CDD fees, this property offers added flexibility and fewer restrictions. Located near Winter Haven’s popular Chain of Lakes, as well as nearby shopping, dining, and major roadways, this home provides both comfort and accessibility.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Garrett Robinson (863-838-5210)
606 TURNBERRY CT, WINTER HAVEN, FL 33884
$280,00047 Days on yellowkey MLS ID: O6390721
4 Days Off yellowkey (back on 4/6/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1891 Built: 1980Monthly Fee: $17 Tax: $3,745 (2025)Community: Cypresswood Patio HomesSingle Family
Taxes:$3,745
Remarks: Under contract-accepting backup offers. Looking for a gated community, 3 bedroom home with a bonus room? No need to look any further! Welcome to the highly sought-after Cypresswood Golf Community, where comfort, security, and convenience come together in this spacious 3-bedroom, 2-bath home with an added air conditioned Florida Room that offers a flexible bonus space perfect for anything your lifestyle calls for. Enjoy beautiful golf course views right from your backyard...a peaceful and scenic setting you won’t want to miss! From the moment you arrive, you’ll appreciate the private front patio, offering a peaceful outdoor space to relax or entertain. Step inside to a home that is completely carpet-free, featuring durable laminate and tile flooring throughout, including the garage which is designed for both easy maintenance and a clean, modern feel. The interior layout provides a generous and open living space, with natural flow between the living, dining, and kitchen areas, making it ideal for everyday living and gatherings. One of the standout features is the Florida Room (with A/C), offering incredible flexibility. Whether used as a playroom, home office, guest space, or private suite, this area can easily be adapted to fit your needs complete with the option for a separate private entrance. The garage has been thoughtfully enhanced with a full kitchen setup, creating a unique and functional space perfect for outdoor entertaining, hosting, or extended cooking needs..an efficient and valuable addition. Community features you’ll love living in Cypresswood Golf & Country Club means access to: 24-hour guarded and gated entry,Community pool,Tennis courts,18-hole championship golf course, Clubhouse and on-site restaurant.Prime location conveniently located near U.S. Highway 27, I-4, and the Polk Parkway. This home offers easy access to everything Central Florida has to offer, including:LEGOLAND, Pega Pig Theme Park, Walt Disney World, Orlando International Airport and Tampa International Airport,Gulf Coast beaches near St. Petersburg and Tampa! Surrounded by a growing area filled with shopping, dining, and everyday conveniences, this location supports both lifestyle and accessibility. This home offers versatility, unique features, and access to a lifestyle-rich community—a true opportunity to enjoy the best of Florida living. Don't miss this opportunity! Come see it today!
Listing is courtesy of: NEW HEIGHTS REALTY GROUP (407-934-0305)
Listing Agent: Daniel Rodriguez (407-934-0305)
1124 SAWGRASS DR, WINTER HAVEN, FL 33884
$360,000391 Days on yellowkey MLS ID: P4934195
REDUCED by $8,000 (2.2%) on 04/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2113 Built: 2022Monthly Fee: $5 Tax: $5,743 (2024)Community: Lake Ashton West Ph Ii SouthSingle Family
Taxes:$5,743
Remarks: Master suite paint updated. Custom built-in bookcases in Den/Office. Club Car golf cart conveys with home purchase. Welcome to your next chapter in beautiful Lake Ashton—Central Florida’s premier 55+ active adult community. This immaculate, nearly new home (just 3 years young!) offers a perfect blend of comfort, style, and Florida charm. With 3 spacious bedrooms, 2 full baths, and a flexible den/office that enjoys tranquil views of the tee box on the 10th fairway of Lake Ashton’s West Golf Course, this home is ideal for both relaxed living and entertaining. Certified as a Green Home by Environments for Living, it also comes with a like-new Onward model Club Car golf cart—featuring lithium batteries—which conveys with the purchase! As you arrive, you’ll be welcomed by elegant architectural details including glass block windows in the master bath, a transom window, sidelight by the front door, and a lovely dining room window, all contributing to the home’s bright, sunlit ambiance. Triple sliding glass doors open up to the veranda, blending indoor and outdoor living with ease. The heart of the home—the kitchen—is a chef’s delight, showcasing Skylar maple cabinetry in a rich Shale finish, beautifully complemented by Silver Frost granite countertops with a beveled edge and fingerprint-resistant stainless-steel appliances. The primary suite is a serene retreat with his-and-hers walk-in closets, while the ensuite bath features handicap-height fixtures and a spacious soaking tub for unwinding at the end of the day. A generous 2-car garage plus a separate golf cart bay adds convenience and storage. This thoughtfully designed home offers a gracious and tasteful setting for everyday enjoyment and entertaining alike. Lake Ashton is more than a neighborhood—it’s a lifestyle. Residents enjoy two 18-hole championship golf courses, a 26,000 sq ft clubhouse, a state-of-the-art Health & Fitness Center, pickleball courts, bowling alley, on-site restaurant, and a vibrant calendar of social events and clubs. Don’t miss this exceptional opportunity to own a home that truly has it all. Call today to schedule your private showing—your Florida dream awaits!
1812 2ND ST NW, WINTER HAVEN, FL 33881
$189,00095 Days on yellowkey MLS ID: TB8469792
1 Days Off yellowkey (back on 3/11/2026)
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1163 Built: 1995 Tax: $1,940 (2025)Community: Habitat For Humanity 01Single Family
Taxes:$1,940
Remarks: Under contract-accepting backup offers. NEW ROOF PRIOR TO CLOSING! Welcome to this 3 bedroom, 1 bathroom newly updated home. The Seller has placed new luxury vinyl flooring throughout which will provide durability in the home. The kitchen has also been updated and once the roof is completed you should have a maintenance free property. This home is locataed in the heart of Winter Haven and is move-in ready ideal for first time home buyers or growing families. Sellers Concessions are available!
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Richard Carey (913-963-9800)
2362 BRASSIE CT, WINTER HAVEN, FL 33884
$274,90073 Days on yellowkey MLS ID: O6384404
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1260 Built: 2022Monthly Fee: $18 Tax: $5,003 (2025)Community: VillmarSingle Family
Taxes:$5,003
Elementary School: Chain O Lakes Elem
Remarks: 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 for entertaining and everyday living. The kitchen showcases quartz countertops, stainless steel appliances, a pantry, and ample cabinetry for storage. Sliding glass doors off the family living area leads to the backyard, offering easy indoor-outdoor living. The thoughtfully designed split-bedroom floor plan provides privacy, with two secondary bedrooms and a guest bath located at the front of the home, while the primary suite is tucked away off the great room. The spacious owner’s retreat includes quartz countertops, dual sinks, a walk-in tile shower, and a generous walk-in closet. Ceramic tile flooring enhances the main living areas with a clean, modern aesthetic, while the bedrooms provides comfortable carpeting. Residents of Villamar enjoy resort-style amenities, including a community pool with lap lane overlooking Crystal Lake, playground, and convenient community mailboxes. The location offers quick access to Route 27 for commuting to Orlando and is just minutes from Legoland, shopping centers, Publix, and Walmart. This community is only two miles from Legoland and in close proximity to Posner Park which offers many stores, restaurants and entertainment for your family, as well as the Orlando's theme parks. Discover the perfect blend of comfort, convenience, and community in this move-in ready home. The photographs included in this listing were taken during a previous rental listing. The property may appear slightly different at time of showing. One or more photos have been modified or virtually staged for illustrative purposes.
Listing is courtesy of: RE/MAX INNOVATION (407-281-1053)
Listing Agent: Millie Brockmeyer (407-970-9782)
2438 4TH ST NE, WINTER HAVEN, FL 33881
$239,90055 Days on yellowkey MLS ID: L4960053
1 Days Off yellowkey (back on 4/5/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1135 Built: 2026 Tax: $223 (2025)Community: Lincoln SubSingle Family
Taxes:$223
Remarks: Under contract-accepting backup offers. Welcome to this beautiful brand-new construction home featuring 3 bedrooms and 2 bathrooms with a thoughtfully designed layout. This home offers tile flooring throughout, sleek stainless steel appliances, and a convenient indoor laundry room for added functionality. Enjoy the privacy of a fully fenced backyard, perfect for relaxing or entertaining. No HOA so bring all your Toys! Located in a quiet neighborhood with a great location close to shopping, dining, and everyday amenities, and just a short drive from LEGOLAND, this home combines comfort, style, and convenience. Call me today for a private showing!
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Sandra Canales (863-205-2641)
1280 DENALI DR, WINTER HAVEN, FL 33881
$409,00095 Days on yellowkey MLS ID: G5107453
INCREASED by $10,000 (2.5%) on 04/05/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2566 Built: 2024Monthly Fee: $92 Tax: $6,203 (2025)Community: Lake Lucerne IiSingle Family
Taxes:$6,203
Elementary School: Bethune Academy
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: One or more photo(s) has been virtually staged. Move-In Incentive Available! Qualified buyers who finance with our affiliated lender may choose one of the following: a 4.5 interest rate or $5,000 toward closing costs (buyer must qualify; incentive applies only when using our affiliated lender). Welcome to this stunning 3-bedroom, 2.5-bath two-story home located on a quiet cul-de-sac in the desirable Lake Lucerne II community. Built in 2024 and beautifully enhanced with thoughtful upgrades, this home offers the peace of new construction with the added value buyers are looking for. The backyard is truly a showstopper, backing up to conservation land with a serene pond view, creating the perfect setting to enjoy your morning coffee or unwind at the end of the day. Vinyl fencing along the sides and a rear metal fence preserve privacy without obstructing the view. Inside, the home features high ceilings throughout, luxury vinyl flooring (with carpeted stairs and tile in bathrooms and laundry), an open-concept floor plan, and elegant design touches including a detailed foyer wall and a charming electric fireplace in the living room. The upgraded kitchen boasts stone countertops, beautiful cabinetry, stainless steel appliances, a large island with bar seating, and a pantry, making it ideal for both everyday living and entertaining. Downstairs also includes a flex room perfect for a home office or guest space, a half bath, and a 2-car garage. Upstairs, a spacious loft offers endless possibilities, family room, playroom, or potential 4th bedroom. The primary suite is a true retreat, featuring tray ceilings, generous space for a king-sized bed, and an upgraded California Closet–designed walk-in closet offering exceptional storage and organization. The primary bath includes dual sinks and a walk-in shower. Two additional bedrooms, a full bath, and a well-appointed laundry room with sink complete the upper level. Additional upgrades include a whole-home water filtration system, security system, and a hybrid heat-pump water heater that efficiently heats water while cooling the garage. Enjoy resort-style living with no CDD, a community clubhouse, two pools, and a playground. Conveniently located near shopping, golf courses, and with easy access to I-4, you’re perfectly positioned between Orlando and Tampa, sunrise to sunset. This home is move-in ready and truly special. Schedule your private showing today and experience it for yourself.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Luisa Hurtado (646-259-1153)
3927 PALAZZO PL, WINTER HAVEN, FL 33884
$305,00074 Days on yellowkey MLS ID: O6383833
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1597 Built: 2023Monthly Fee: $40 Tax: $4,716 (2025)Community: Villamar Ph 4Single Family
Taxes:$4,716
Remarks: 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 months of uncertainty, this home is completely MOVE-IN READY. No waiting, no construction process, no guesswork — just the ability to step inside and immediately begin enjoying your new home. From the moment you enter, the home creates a lasting impression. The soaring ceilings and welcoming walk-in foyer set the tone for a bright, open, and airy living experience. The elevated ceiling height dramatically enhances the feeling of space, giving the home a grand and expansive presence that feels far larger than expected. Natural light pours through the living areas, creating a warm and uplifting atmosphere throughout the day. Designed for modern living and meaningful moments, the open-concept floor plan encourages connection and comfort. The seamless flow between the kitchen, dining, and living spaces makes everyday life effortless while providing the perfect backdrop for gatherings, celebrations, and quiet evenings at home. Luxury vinyl flooring throughout the main living areas adds both style and durability, creating a cohesive and low-maintenance environment that complements any design aesthetic. Built in 2023, this residence offers the peace of mind that today’s buyers value most. Everything reflects newer construction standards, meaning you can enjoy your home without the typical concerns of replacing major components or tackling costly updates. Simply move in and focus on living. Adding even more value and convenience, the home includes a full security system with installed cameras that convey with the property, providing comfort and confidence from day one. With three bedrooms and two bathrooms, this home offers flexibility for a variety of lifestyles. Whether accommodating guests, creating a home office, or designing a playroom, the space adapts beautifully to your needs. The primary suite provides a relaxing retreat, complete with a spacious walk-in closet and a well-appointed bathroom featuring a dedicated vanity seating area — a small but meaningful touch that enhances everyday routines. Step outside and the lifestyle continues. A charming front porch offers a welcoming space to relax and unwind, while the backyard provides the perfect setting for entertaining, grilling, or enjoying peaceful outdoor moments. The included playground set adds both convenience and enjoyment. The location of the home is equally appealing, offering exceptional convenience with close proximity to a variety of shopping, dining, and everyday essentials. Residents also benefit from the community’s amenities, including a large resort-style pool with abundant seating and shaded cabana areas, as well as recreational spaces designed for enjoyment and leisure. This is more than just a home — it is an opportunity to skip the wait, avoid construction uncertainties, and immediately embrace a space designed for comfort, connection, and everyday living. Don’t miss your chance at beautiful, easy living!
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Iliana Perez (407-990-7293)
287 INMAN BLVD, WINTER HAVEN, FL 33881
$315,00031 Days on yellowkey MLS ID: S5147134
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1560 Built: 2023Monthly Fee: $49 Tax: $3,542 (2025)Community: Inman Grvs Ph 2Single Family
Taxes:$3,542
Elementary School: Elbert Elem
Remarks: Welcome to 287 Inman Blvd—where modern comfort meets effortless Florida living in the heart of Winter Haven. This beautifully maintained home truly feels like new, offering the peace of mind of recent construction with thoughtful upgrades already in place. From the moment you step inside, you’ll notice a clean, contemporary design paired with warm, inviting spaces. The open-concept layout flows seamlessly, making it perfect for both everyday living and entertaining. The kitchen is a standout feature, enhanced with a stylish backsplash on the island and throughout, complemented by upgraded light fixtures that add a polished, custom feel. The home also features low-maintenance quartz countertops as well as stainless steel appliances. This home has already been elevated beyond builder-grade with valuable improvements, including solar panels for energy efficiency, a vinyl privacy fence for added outdoor enjoyment, and upgraded ceiling fans and lighting throughout. Tile flooring in the wet areas offers durability and easy maintenance, while cozy carpeting in the bedrooms creates a comfortable retreat at the end of the day. Step outside and enjoy a backyard space that’s ready for relaxing evenings, pets, or gatherings—fully enclosed for privacy and convenience. Location is where this home truly shines. Situated just about one and a half miles from the soon-to-open Publix shopping plaza, you’ll have everyday essentials right around the corner. Plus, you’re only minutes from downtown Winter Haven, known for its charming local shops, dining, and access to the Chain of Lakes lifestyle. Commuters will appreciate the quick access to US-27, making travel to surrounding areas simple and efficient. If you’ve been searching for a move-in-ready home with upgrades already done, modern finishes, and a prime location, this is one you don’t want to miss.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Chris Loschiavo (863-280-2201)
688 AUGUSTA RD, WINTER HAVEN, FL 33884
$337,00068 Days on yellowkey MLS ID: P4937966
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1586 Built: 1980Monthly Fee: $137 Tax: $3,636 (2025)Community: Cypresswood Fairway Patio HomesSingle Family
Taxes:$3,636
Remarks: Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Country Club community of Winter Haven. Thoughtfully designed with a desirable split-bedroom floorplan, this residence offers both privacy and functionality for everyday living and entertaining. Plus, seller is currently in the process of installing a NEW ROOF! Step inside to find beautiful hardwood and tile flooring throughout, creating a warm yet low-maintenance living environment. The spacious primary suite serves as a private retreat, complete with direct access to the screen-enclosed pool deck — perfect for enjoying your morning coffee or an evening swim under the stars. The heart of the home flows seamlessly into a dedicated dining area, with an exciting bonus room just beyond featuring a fun wet bar — ideal for hosting gatherings, game nights, or creating your own lounge space. Two additional bedrooms are situated on the opposite side of the home, providing comfort and privacy for family or guests. Outdoors, the screened pool deck offers the perfect space for relaxing or entertaining year-round. The garage includes a dedicated workshop area, making it ideal for hobbyists, DIY enthusiasts, or extra storage needs. Beyond the home itself, residents enjoy an exceptional lifestyle within this premier community, featuring a championship 18-hole golf course, community pool, fitness center, clubhouse, on-site restaurant, and pro shop. Exciting new amenities are on the way, including lighted tennis courts, pickleball, and basketball courts — offering something for everyone. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando and Tampa International Airports, and the gulf-side beaches of Tampa/St. Pete! This is more than just a home — it’s a lifestyle. Schedule your private showing today!
Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)
Listing Agent: Kayly Malinas, Pa (863-258-1426)
2336 W CANNON TER NW, WINTER HAVEN, FL 33881
$729,000111 Days on yellowkey MLS ID: L4958323
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1856 Built: 1995 Tax: $6,634 (2025)Community: West Cannon TerraceSingle Family
Taxes:$6,634
Remarks: HUGE PRICE DROP! Completely renovated home with new pool on Cannon Lake! Welcome to your dream lakeside retreat on a sprawling lot with 120 feet of pristine lakefront on Lake Cannon. This completely renovated three-bedroom, two-bathroom home boasts an open floor plan with high ceilings and a desirable split-bedroom layout. The stunning kitchen features granite countertops, a counter-height breakfast bar, and brand-new Samsung bespoke appliances, including an induction stove, perfect for culinary enthusiasts. The expansive primary suite offers a luxurious en suite bath with a large shower equipped with multiple showerheads, including a rain showerhead, and sliding glass doors that lead to an impressive outdoor entertaining space. The screened-in patio, perfect for hosting gatherings, overlooks the brand-new saltwater, heated pool and spa, completed in 2025, creating an idyllic setting for relaxation and fun. Additionally, the home features a new roof and new windows, ensuring peace of mind for years to come. Enjoy unobstructed views of the lake from your large outdoor area, ideal for summer barbecues or evening stargazing. Conveniently located near shopping, restaurants, and entertainment, this home truly offers the best of lakeside living on the chain of lakes.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
2800 SUNSET DR NW, WINTER HAVEN, FL 33881
$349,000319 Days on yellowkey MLS ID: P4935252
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1536 Built: 1972 Tax: $1,432 (2024)Community: Idylwild HeightsSingle Family
Taxes:$1,432
Elementary School: Walter Caldwell Elem
Remarks: One or more photo(s) has been virtually staged. This 3 bedroom, 2 bathroom home is located in Idylwild Heights a charming residential subdivision nestled in Winter Haven, Florida. Winter Haven is a picturesque city celebrated for its chain of lakes and friendly community atmosphere. Known for its welcoming ambiance and established neighborhood feel, Idylwild Heights offers residents an appealing blend of suburban tranquility and convenient urban access.
Listing is courtesy of: CENTURY 21 WOLF'S CROSSING REALTY (407-449-0000)
Listing Agent: Lucy Martinez (863-521-4156)
638 LAKE DEXTER CIR, WINTER HAVEN, FL 33884
$244,90049 Days on yellowkey MLS ID: O6390069
REDUCED by $5,000 (2.0%) on 04/03/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1316 Built: 1989Monthly Fee: $35 Tax: $3,649 (2025)Community: Lake Dexter Woods Ph 02Single Family
Taxes:$3,649
Remarks: This move-in-ready, three-bedroom, two-bathroom home is located in the sought-after Lake Dexter Woods community. The residence features a functional layout designed for modern comfort and style, highlighted by an attached one-car garage and low-maintenance tile flooring throughout the entire home. The updated kitchen serves as a stylish centerpiece, equipped with beautiful granite countertops and sleek stainless-steel appliances. Outside, you can relax and enjoy the fresh air from your private porch and patio, which overlooks a fully fenced-in backyard, providing a secure space for outdoor entertaining or pets. The location offers a perfect blend of comfort and convenience, situated near top-rated schools, multiple grocery stores, and popular local attractions. Residents can enjoy a resort-style lifestyle with access to premium community amenities, including sparkling pools, tennis/pickleball courts, and more.
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
236 W LAKE INA DR, WINTER HAVEN, FL 33884
$430,00032 Days on yellowkey MLS ID: O6395853
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2576 Built: 1979 Tax: $4,971 (2025)Community: Eloise Woods Lake Roy Unit Pb 14 Pg 19Single Family
Taxes:$4,971
Remarks: Live the lake life you've been dreaming of in this beautifully maintained 3-bedroom, 2-bath home in Winter Haven! Perfectly positioned for those who love being on the water, this property offers lake access with use of two community docks ideal for boating, fishing, or catching stunning Florida sunsets. Step inside to find a bright, comfortable layout enhanced by new windows that fill the home with natural light. Major updates have already been taken care of, including a newer roof, HVAC system, water heater, new garage door giving buyers peace of mind and true move-in-ready convenience. The easy access to the docks makes it simple to embrace an active, outdoor lifestyle without the high price of direct waterfront. Located just minutes from LEGOLAND Florida Resort, shopping, dining, and entertainment, this home offers the perfect balance of adventure and convenience. Whether you're a boating enthusiast, weekend adventurer, or simply someone who loves being near the water, this property delivers the lifestyle -- not just the home.
Listing is courtesy of: RELENTLESS REAL ESTATE CO. (321-302-0763)
Listing Agent: Scott Loveridge (321-302-0763)
3832 TRADITIONS BLVD N, WINTER HAVEN, FL 33884
$250,00032 Days on yellowkey MLS ID: TB8490822
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2109 Built: 2006Monthly Fee: $504 Tax: $1,304 (2025)Community: Traditions Ph 01 Plat Book 131 Pgs 47 Thru 54 LotSingle Family
Taxes:$1,304
Middle School: Mclaughlin Middle
Remarks: One or more photo(s) has been virtually staged. Freshly painted in Oct 2025, this well-maintained home in Traditions offers a split floor plan, water views, and a spacious primary suite with dual closets and a private bath. Enjoy a screened lanai, open living areas, and a well-equipped kitchen. Community amenities include a clubhouse, pool, fitness center, and lake access. Conveniently located near Winter Haven with easy access to Lakeland, Tampa, and Orlando. HOA includes lawn care and exterior painting.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Bridget Franklin (813-424-9043)
1727 SECOND ST NE, WINTER HAVEN, FL 33881
$277,00041 Days on yellowkey MLS ID: TB8490278
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1470 Built: 2022 Tax: $4,565 (2025)Community: Smith Ida M Sub 2Nd Replat Pb 33 Pg 16Single Family
Taxes:$4,565
Remarks: 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, 2-car garage home features 1,421 square feet of thoughtfully designed living space with an open-concept floor plan ideal for both everyday living and entertaining. Step inside to find tray ceilings in the living room and primary suite, enhancing the home’s spacious feel, along with LED recessed lighting throughout and abundant natural light. The kitchen is equipped with granite countertops, solid wood soft-close cabinetry, and energy-efficient appliances, combining style with functionality. This home is loaded with upgrades and energy-saving features, including efficient pull-out windows, architectural 30-year shingles, Decora switches, ceiling fans throughout, and window blinds already in place — making it truly move-in ready. Enjoy the benefits of new construction in Central Florida without the wait to build, all in a location that offers easy access to Orlando, Lakeland, Tampa, shopping, dining, and major highways.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Regan Fuller (727-243-6216)
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