Displaying: For Sale
Location: Winter Haven
Property Type(s): Single Family
Price: $300,000 to $399,000
Do Not Show Listings
Winter Haven - 287 properties found
1059 MICHELANGELO LN, WINTER HAVEN, FL 33884
$364,500147 Days on yellowkey MLS ID: S5142551
REDUCED by $500 (0.1%) on 06/23/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1844 Built: 2024Monthly Fee: $55 Tax: $3,878 (2025)Community: Estates/Lk FlorenceSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,878
Elementary School: Elbert Elem
High School: Winter Haven Senior
Tax Year: 2025
Middle School: Denison Middle
Remarks: Discover your dream home without the hassle! This stunning two-year old construction features all the modern upgrades you desire. Why buy new when you can purchase this like-new home with so many stylish finishes and energy efficient appliances. Welcome home to this immaculate 4 bedroom / 2 bathroom / 2 car garage home in Winter Haven! Shows like a model! No CDD! Low HOA fees, and lower taxes. GREAT OPEN FLOORPLAN with lots of living space, this home was BUILT IN 2024 and has plenty of features throughout. The home has upgraded tiled flooring throughout the main living areas and a huge great room, perfect for entertaining! The kitchen features a spacious center island, granite countertops, stainless steel appliances, tiled backsplash, and plenty of cabinetry space. There are 4 spacious bedrooms. The owner's suite boasts an en suite bathroom with dual sinks. The backyard is generously sized and is FULLY FENCED and includes a screened patio and a shed for a perfect outside living experience whether you are relaxing, entertaining or hosting family gatherings. Lots of upgrades! Close to shopping, dining, and Legoland. Perfectly situated between Orlando and Tampa .
Listing is courtesy of: RIGHT TRACK REALTY (953-437-4747)
Listing Agent: Phyllis Haigler (804-641-9763)
302 STERLING DR, WINTER HAVEN, FL 33884
$365,000Listed 06/24/2026 3:50PM MLS ID: O6419370
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2460 Built: 1994Monthly Fee: $24 Tax: $2,764 (2025)Community: BerryhillSpa: NoSingle Family
Taxes:$2,764
Elementary School: Garden Grove Elem
Remarks: Short Sale. Located in Winter Haven, this 4-bedroom, 2-bath home offers approximately 2,460 square feet of living space with a two-car garage, spacious layout, and private pool. The home's generous floor plan provides multiple living areas and ample space for everyday living, entertaining, or accommodating a variety of household needs. Based on available information and photographs, the property appears to be in generally good cosmetic condition. The home offers an opportunity for buyers seeking a larger residence with a functional layout and desirable outdoor living features. The property includes a screened lanai and pool area; however, buyers are encouraged to independently verify the condition and functionality of the pool and all related equipment. Conveniently located near shopping, dining, schools, and other area amenities, this property combines size, location, and potential in today's market. Buyers are encouraged to conduct thorough inspections and verify the condition and functionality of all systems, components, and improvements. Buyers should verify all information. Agents: Please review all private remarks prior to scheduling a s
Listing is courtesy of: KELLER WILLIAMS ELITE REALTY (239-949-8338)
Listing Agent: Jonathon, Pa Mcleod (239-357-8938)
306 TERRANOVA BLVD, WINTER HAVEN, FL 33884
$390,0001 Day on yellowkey MLS ID: TB8522219
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2413 Built: 2006Monthly Fee: $55 Tax: $6,079 (2025)Community: Terranova Ph 04Single Family
Taxes:$6,079
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Remarks: Set on a spacious .24-acre homesite in the gated Terranova community, this beautifully designed 4-bedroom, 3-bathroom home offers over 2,400 square feet of comfortable living space with a layout that perfectly balances openness and privacy. Mature fruit trees, a low HOA, and no CDD fees make this an exceptional opportunity in one of Winter Haven’s most desirable neighborhoods. Inside, you'll find an inviting open-concept design filled with natural light, enhanced by tile flooring throughout the main living areas and plush carpet in the bedrooms. The split-bedroom floor plan provides added privacy, making it ideal for families, guests, or multi-generational living. Spacious gathering areas flow seamlessly into a separate dining space featuring custom built-in shelving and a convenient sliding glass door leading to the backyard. The heart of the home is the generously sized kitchen, complete with a breakfast bar, abundant cabinet storage, and plenty of workspace for cooking and entertaining. Just beyond, the screened patio offers the perfect place to enjoy Florida’s year-round sunshine while overlooking the expansive backyard. Retreat to the oversized primary suite, where wide windows bring in beautiful natural light. The suite also features a large walk-in closet and a private ensuite bath with a soaking tub, separate shower, and dual functionality designed for everyday comfort. Additional highlights include a 2-car garage, three full bathrooms, ample storage throughout, and a thoughtfully designed single-story floor plan that maximizes both space and convenience. Located just minutes from LEGOLAND Florida Resort, shopping, dining, major roadways, and Winter Haven’s renowned Chain of Lakes, this home combines the tranquility of a gated community with easy access to everything Central Florida has to offer. Call now and schedule your viewing today because space, functionality, and location come together beautifully in this Terranova gem. ***FREE 1/0 Rate Buydown when using the seller's preferred lender!***
Listing is courtesy of: LPT REALTY LLC (813-359-8990)
Listing Agent: Andrew Duncan (813-359-8990)
6457 DOMIZIO DR, WINTER HAVEN, FL 33884
$309,49097 Days on yellowkey MLS ID: O6392165
2 Days Off yellowkey (back on 6/24/2026)
INCREASED by $500 (0.2%) on 04/07/2026
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2326 Built: 2025Monthly Fee: $53 Tax: $32 (2024)Community: Villa Mar 40'SSingle Family
Taxes:$32
Elementary School: Pinewood Elem
Tax Year: 2024
Remarks: Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.
Listing is courtesy of: LENNAR REALTY (800-229-0611)
Listing Agent: Ben Goldstein (407-310-7677)
2799 ADELINE AVE, WINTER HAVEN, FL 33881
$305,740183 Days on yellowkey MLS ID: O6369098
1 Days Off yellowkey (back on 3/25/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1328 Built: 2026Monthly Fee: $8 Tax: $3,455 (2025)Community: Willowbrook SouthSingle Family
Taxes:$3,455
Remarks: Under Construction. The Archer II is one of our one-story floorplans features in our Willowbrook South community in Winter Haven, Florida. Take your pick between two sleek exterior options when choosing this floorplan. Inside this 3 bedroom, 2 bathroom home you’ll find 1,328 square feet of comfortable living. The open concept layout allows for seamless movement between spaces making entertaining guests a breeze. It also provides homeowners versatile design options. The kitchen features shaker-style cabinets, quartz countertops, and stainless steel appliances, which are sure to both turn heads and make meal prep easy. You’ll bever be too far from the action with the living and dining area right there. In every bedroom, besides the primary bedroom, you’ll have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom features luxury vinyl plank flooring that will be sure to stand out. It also has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Sharing a sink isn’t a worry with the double vanity, and you also get additional privacy with a separate door for the toilet and shower. Contact us today and find your home at Willowbrook South. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Paul King (407-519-3940)
2323 BRASSIE CT, WINTER HAVEN, FL 33884
$313,967252 Days on yellowkey MLS ID: L4956626
2 Days Off yellowkey (back on 5/21/2026)
REDUCED by $5,000 (1.6%) on 05/01/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2405 Built: 2025Monthly Fee: $68 Tax: $7,100 (2025)Community: Villa Mar Phase 3Single Family
Taxes:$7,100
Middle School: Berkley Accelerated Middle
Remarks: Under Construction. This two-story home features 4 bedrooms and 2 and a half baths. This Home begins with a two-story foyer opening up to the spacious first floor living spaces. The kitchen shines with abundant counter space and an island perfect for entertaining, Upstairs, you will find all four bedrooms and the large loft area. CUSTOM EXTERIOR includes 30-year mildew resistant dimensional shingles Cementitious masonry finish walls & gables, Termite treated with Bora care-renewable after 1st year Designer paint schemes Two convenient garden hose bibs, Dead bolt locks on all exterior doors, Low maintenance aluminum fascia and vinyl soffit Professionally landscaped yards, two exterior weatherproof electrical outlets, Insulated, fiberglass front & rear doors, Decorative coach lights on garage and front entry. EXCEPTIONAL INTERIOR includes Stain resistant designer carpet, Recessed LED lighting in kitchen & family room, Level 1 tile standard in kitchen, laundry, foyer, and bathrooms Prewire for ceiling fan and 4 LED discs in family room, Pre-wiring for ceiling fans in all bedrooms with dual switches LED Disc, with rocker switches in all bedrooms, Doorbell chimes and protective smoke detectors Knock down texture on all interior walls and ceiling, Generous walk in closets with ventilated shelving,6 TV/Cable jacks or phone jacks, Vaulted ceilings, Wood Window Sills Brushed nickel hinges, fixtures and door knobs Indoor laundry room, Upgraded 5 1/4 baseboards throughout,5 panel smooth finish interior doors with brushed nickel, lever door handles, Garage door opener prewire, Two tone Interior paint package 220-volt dryer outlet Custom cased openings, GOURMET KITCHEN includes Designer recessed lighting Custom wood cabinets with adjustable shelves Included 36” upper cabinets with crown molding and custom bump out Stainless steel double bowl sink. Single lever brushed nickel faucet with pull out sprayer, Energy efficient multi-cycle dishwasher, Smooth top stove with self-cleaning feature, Space saver microwave above the range, Ice maker connection Spacious pantry with ventilated shelving. LUXURY BATH AREA includes Easy care garden tub/shower combination in master bath, Elongated toilets, Pull out drawers in most cabinets, Dual rectangle sinks, Upgraded brushed nickel faucets ENERGY EFFICIENCY includes Double pane insulated windows with tilt-in sash for easy cleaning, Energy efficient Whirlpool appliance package,R-38 ceiling insulation, Continuous soffit attic ventilation, Off ridge roof ventilation,15 SEER Heat Pump with digital thermostat Low volume flush toilets CONSTRUCTION QUALITY includes Interior wood studs 16” on center, Professionally engineered roof truss system, Fiber reinforced concrete slabs with vapor barrier 200 AMP service, Engineered to meet or exceed all wind codes 50-gallon water heater, Finished garage interiors Concrete, block construction ,Tax built-in pest control system(tubes in wall) This community is only a short, 10-minute drive to downtown and less than 5 minutes to shopping, schools, and more! Winter Haven is perfectly situated in the middle of Tampa and Orlando, each of which is only an hour's drive away. Villa Mar is perfect for those seeking vacation amenities alongside neighborhood conveniences. Winter Haven is home to Legoland Florida, Willowbrook Golf Course, and Auburndale Speedway. Within Villa Mar itself, there will be many amenities to suit whatever stage of life your family is in.
Listing is courtesy of: ADAMS HOMES REALTY (863-619-8120)
Listing Agent: Claudia Gutierrez Alvarez (602-800-4341)
1871 EMILY DR, WINTER HAVEN, FL 33884
$312,50043 Days on yellowkey MLS ID: S5149517
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2012 Built: 2005Monthly Fee: $38 Tax: $3,862 (2025)Community: Emily EstatesSingle Family
Taxes:$3,862
Remarks: Beautiful single-family home offering 4 bedrooms and 2 bathrooms with approximately 2,012 square feet of heated living space. This spacious residence features high ceilings and a functional layout designed for comfortable living and entertaining. The kitchen includes space for a breakfast table and flows seamlessly into a separate dining room, while an additional family room provides the perfect setting for gatherings. Conveniently located near Cypresswood Golf & Country Club, East Central Park, and Rotary Park, offering access to outdoor recreation, including skating, softball, and picnic areas. The property also provides easy access to U.S. Highway 27, with shopping, dining, and everyday conveniences just minutes away, including Publix and Walmart.
Listing is courtesy of: REALTY OF AMERICA (321-732-5369)
Listing Agent: Cisco Romero (407-922-6375)
3986 JACLYNS JETTY, WINTER HAVEN, FL 33884
$300,000Listed 06/24/2026 9:57AM MLS ID: L4962993
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1526 Built: 2001Monthly Fee: $440 Tax: $1,767 (2025)Community: Cypress Landing Ph 02Single Family
Taxes:$1,767
Elementary School: None
High School: None
Middle School: None
Remarks: LAKEFRONT LIVING in Winter Haven! Welcome to 3986 Jaclyns Jetty, a beautifully maintained 3-bedroom 2-bathroom, split bedroom floor plan with a large and open living area, waterfront home offering the perfect blend of comfort, convenience, and breathtaking views of Lake Dexter. Nestled within the desirable Cypress Landing community, this residence is ideally positioned to capture stunning lake views and Florida sunsets from the comfort of your own backyard. Whether you're enjoying your morning coffee, unwinding after a long day, or entertaining family and friends, the tranquil waterfront setting creates a lifestyle many only dream of. Inside, you'll find a bright and inviting floor plan with spacious living areas designed for everyday living and effortless entertaining. Large windows and sliding glass doors allow natural light to pour inside while showcasing picturesque views of the lake beyond. The kitchen offers ample cabinetry, generous counter space, and a functional layout that flows seamlessly into the dining and living areas. The primary suite provides a peaceful retreat with water views, an en-suite bathroom, and ample closet space. Additional bedrooms offer flexibility for guests, family members, or a home office. Step outside and experience what makes this property truly special. The backyard overlooks beautiful Lake Dexter, providing a picturesque backdrop for everyday living and outdoor enjoyment. Whether you enjoy fishing, boating, kayaking, or simply soaking in the peaceful waterfront scenery, you'll appreciate having lakefront living right outside your door. Residents of Cypress Landing enjoy an outstanding array of amenities, including a heated community pool, tennis courts, private lake access, and a community boat ramp providing convenient access to Lake Dexter. These amenities create the perfect opportunity to embrace the Florida lifestyle and enjoy year-round recreation close to home. Conveniently located near shopping, dining, medical facilities, LEGOLAND Florida, and major roadways, this property offers the ideal balance of waterfront tranquility and everyday convenience. Whether you're searching for a primary residence, seasonal retreat, or waterfront escape, this move-in ready lakefront property presents a rare opportunity to enjoy the best of Winter Haven's lake lifestyle.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Christine Hubbert (863-370-4915)
1558 DREXEL AVE NE, WINTER HAVEN, FL 33881
$349,50071 Days on yellowkey MLS ID: L4960971
3 Days Off yellowkey (back on 6/22/2026)
REDUCED by $34,500 (9.0%) on 06/20/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1160 Built: 1957 Tax: $2,598 (2025)Community: Lake Elbert Heights Unit 01 02 RepSingle Family
Taxes:$2,598
Remarks: Under contract-accepting backup offers. Virtually Staged. HUGE $15,000 PRICE DROP! Completely renovated and move-in ready, this beautifully updated home combines modern style with everyday comfort in the heart of Central Florida. Step inside to a bright, open floor plan filled with natural light from large floor-to-ceiling windows throughout—including in the bedrooms. The spacious living areas flow seamlessly, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. The stunning kitchen has been completely updated with beautiful soft-close cabinetry, luxurious quartz countertops, stainless steel appliances, and recessed lighting—offering a sleek, contemporary look and exceptional functionality. Luxury vinyl plank flooring runs throughout the home, complemented by fresh interior paint, modern fixtures, and stylish ceiling fans that complete the elegant finish. The primary suite provides a private retreat, while additional bedrooms offer flexibility for family, guests, or a home office. Both bathrooms have been tastefully remodeled with updated tile, vanities, and fixtures. Outside, enjoy your private backyard oasis—fully enclosed with a block wall for enhanced privacy. A sparkling inground pool with paver deck sets the stage for year-round Florida living, whether you’re hosting a gathering or enjoying a quiet evening under the stars. Additional features include a separate exterior laundry/storage room for added convenience. Ideally located near shopping, dining, schools, and major roadways, this home offers easy access to Winter Haven’s famous Chain of Lakes and other nearby Central Florida attractions. Every detail has been updated—move right in and start enjoying the Florida lifestyle today! Schedule your private showing before it’s gone.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
961 DREXEL AVE NE, WINTER HAVEN, FL 33881
$305,000121 Days on yellowkey MLS ID: L4959592
REDUCED by $10,000 (3.2%) on 06/08/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1856 Built: 1948 Tax: $3,409 (2025)Community: Anna MarSingle Family
Taxes:$3,409
Elementary School: Inwood Elem
Middle School: Westwood Middle
Remarks: ***PRICE DECREASE*** This unique 2-story home in Winter Haven is full of character and charm, located just three houses down from scenic Lake Elbert. Thoughtfully updated while preserving its warm, rustic appeal, this property offers a welcoming atmosphere from the moment you arrive. Outdoor enthusiasts will love the 2.4-mile paved loop trail surrounding Lake Elbert, complete with boardwalks and beautiful landscaping—perfect for morning walks, bike rides, or peaceful evening strolls. The home is in walking distance to Downtown Winter Haven, the public boat ramp and park, and Polk State College’s Winter Haven Fine Arts Building, offering exceptional convenience and lifestyle amenities. Inside, you’ll find live-edge wood countertops, natural wood trim, and an open kitchen overlooking the family and dining rooms. The kitchen features stainless steel appliances, newer cabinets, and a rustic flair originally crafted by an Amish family. The spacious family room includes a large picture windows that frame the beautiful front yard and mature oak tree. The primary bedroom and bathroom are conveniently located downstairs, while the second floor offers two additional bedrooms, a bonus room, a full bathroom, and a loft area with generous storage closets. Both bathrooms have been updated with newer cabinets, newer countertops, and newer tile. Additional interior upgrades include newer luxury vinyl plank flooring, newer windows, newer light fixtures and ceiling fans, and fresh interior paint. The home also features a newer A/C system. Outside, the home offers a covered front porch perfect for evening relaxation, mature landscaping, and a fenced yard on nearly a quarter-acre, with most of the outdoor space located in the front of the home. Ideally situated near Lake Elbert, Downtown Winter Haven, Polk State College, shopping, dining, parks, and medical facilities, this home offers both convenience and character. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Lisa Ford (863-510-3890)
1328 DAISY FIELD DR, WINTER HAVEN, FL 33884
$380,00075 Days on yellowkey MLS ID: L4960820
REDUCED by $10,000 (2.6%) on 05/19/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2696 Built: 2024Monthly Fee: $30 Tax: $7,633 (2025)Community: Harmony/Lk Eloise Ph 1Single Family
Taxes:$7,633
Remarks: HUGE $45,000 PRICE DROP! Welcome to one of the largest homes in the desirable Harmony Lake Eloise community! This spacious 5-bedroom, 3-bathroom residence offers a versatile and thoughtfully designed layout perfect for modern living. A generously sized flex room—currently used as a dining area—can easily be converted into a 6th bedroom, home office, or bonus space to suit your needs. The spacious kitchen is a true centerpiece, featuring quartz countertops, beautiful cabinetry, recessed lighting, stainless steel appliances, a large kitchen island, and a walk-in pantry. The interior paint throughout the home offers a soft, inviting color palette that’s easy on the eyes. The first floor showcases beautiful tile flooring throughout, along with a large bedroom and full bathroom—ideal for guests or multigenerational living. You’ll also find an additional sitting area or playroom, providing even more functional living space. Upstairs, all bedrooms are upgraded with luxury vinyl flooring, offering both style and durability. The conveniently located upstairs laundry room adds everyday ease. The expansive primary suite boasts his-and-her closets, dual vanities, and a walk-in shower —your own private retreat. With tons of storage throughout and one of the largest floor plans in the community, this home combines space, comfort, and flexibility. Enjoy a low monthly HOA fee and access to a beautiful community pool. Ideally located just minutes from Lake Eloise, Legoland Florida Resort, shopping, dining, schools, and major roadways, with easy access to Orlando, Tampa, and Walt Disney World. This is a must-see property in Winter Haven!
681 LAKE DEXTER CIR, WINTER HAVEN, FL 33884
$349,000Listed 06/24/2026 10:10AM MLS ID: P4939095
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1320 Built: 1990Monthly Fee: $41 Tax: $1,397 (2025)Community: Lake Dexter Woods Ph 02Single Family
Taxes:$1,397
Remarks: PRESENTING A BEAUTIFUL LAKEFRONT RETREAT ON LAKE DEXTER! Welcome to this charming 3 BD / 2.5 BA two-story residence that offers stunning water views, modern updates, and the perfect blend of comfort and Florida lakefront living. The spacious living room features a cozy gas fireplace and flows seamlessly into the beautifully remodeled kitchen and a convenient dining area. Bathrooms have been tastefully updated, while all windows have been replaced with energy-efficient double-pane windows. The primary suite offers a unique private balcony overlooking Lake Dexter, creating the perfect spot to enjoy peaceful lake views. Additional features include an air-conditioned sun room and a relaxing expansive private patio for outdoor enjoyment. Step outside to experience the true highlight of the property—direct access to Lake Dexter with a large private dock and beautiful beach area, ideal for boating, fishing, kayaking, or simply soaking in the waterfront scenery. Combining tasteful updates, inviting living spaces, and exceptional lakefront amenities, this property offers an outstanding opportunity to enjoy the Florida lifestyle at its finest.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Erin Floyd (863-412-2286)
58 LAKE LINK CIR SE, WINTER HAVEN, FL 33884
$398,50047 Days on yellowkey MLS ID: P4938677
0 Days Off yellowkey (back on 5/15/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2000 Built: 1971 Tax: $5,997 (2025)Community: Lake Link EstatesSingle Family
Taxes:$5,997
Remarks: Under contract-accepting backup offers. Location, Location, Location! Welcome Home! This beautifully remodeled 3-bedroom, 2-bath block home offers 2,000 sq ft of living space. Situated on a desirable corner lot, this block home blends style, function, and Florida living at its best. Inside, you’ll find updates throughout, including fresh finishes, modern fixtures, Luxury Vinyl Plank, and a bright, open layout perfect for both everyday living and entertaining. The kitchen showcases all wood cabinets with Quartz counter tops and all new Stainless Steel Appliances. The home features a newer roof and a brand-new water heater, giving buyers peace of mind from day one. Enjoy the outdoors year-round with a screened-in pool, ideal for relaxing or hosting gatherings. The fully fenced backyard provides privacy, space for pets or play, and plenty of room to make it your own. This home truly checks all the boxes — updated, spacious, and designed for easy Florida living. A must-see for anyone looking for comfort, style, and value. Conveniently located to down town Winter Haven and Medical, and located between Tampa and Orlando. Schedule your showing today!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Christopher Howard (888-668-8283)
5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884
$340,000191 Days on yellowkey MLS ID: P4937220
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1677 Built: 2016Monthly Fee: $5 Tax: $2,785 (2024)Community: Lake Ashton West Ph 01Single Family
Taxes:$2,785
Remarks: Don't miss out on this opportunity to reside in a home located on the WEST golf course in Lake Ashton. FURNITURE AVAILABLE! GOLF CART INCLUDED! WASHER/DRYER INCLUDED! This Callaway Floor plan with NEW A/C (December 2025) is a "Green" home with 2 Bedrooms, 2 Baths, Plus a FLEX ROOM. This home has over 1,660 sq. ft. of living space. Located on the 17th Fairway of the West Golf Course in Lake Ashton, a guard-gated Florida 55+ community, this home offers a Split Plan. The kitchen package features a spacious dinette area, granite counter tops, stainless steel appliances, 42" cabinets and breakfast bar. The foyer with high ceiling is welcoming and is a passage to the laundry room and 2nd bedroom. The laundry room is directly to your left and to your right is a hallway with 2 linen closets that leads to the 2nd bedroom and Guest Bath. The laundry room is accessible from the foyer and the garage. The living room, kitchen and dinette are centrally located in this home- OPEN & SPACIOUS. The Den/Office is directly off the living room and is currently being used as a bedroom. There are triple sliders in the living room that separate the screened and covered lanai with tile floor. The primary suite with large walk in closet includes a master bath with dual sinks and a comfort height vanity, walk in shower and separate water closet with window. Other upgrades in this home include tile flooring in the Living Areas (Bedrooms are carpeted), water softener, ceiling fans, screened entryway, automatic screen on the garage door. Lake Ashton offers a Main Clubhouse with a theater, bowling lanes, card, craft and billiard rooms, fitness center, restaurant (Charm City), and outdoor heated pool. Residents also enjoy tennis courts, shuffleboard courts, Bocce and planned activities in the community. There is a Health and Fitness Center with an indoor heated lap pool, 1/2 basketball, indoor racquetball, pickle ball courts and MORE... Make an appointment to tour this home and Lake Ashton TODAY!
Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)
Listing Agent: Lori Raath (863-409-6899)
443 ITUNA CIR, WINTER HAVEN, FL 33881
$308,90063 Days on yellowkey MLS ID: L4961315
REDUCED by $10,220 (3.2%) on 06/24/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1644 Built: 2026Monthly Fee: $50Community: Harbor At Lake HenrySingle Family
Taxes:$0
Remarks: Under Construction. Brand-new 3-bedroom 2-bath home! The Ashlyn features an inviting and open living area under an airy volume ceiling. Relax in your private owner's suite featuring a large en-suite bath with a decorative tiled shower with glass enclosure, dual vanities, a closeted toilet, and walk-in wardrobe .Two secondary bedrooms share a hall bath. Plus, enjoy outdoor living on your covered 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: Beautifully designed kitchen with: Breakfast bar. Quartz countertops. 36-in. espresso birch wood cabinets with decorative knobs/pulls. Stainless steel undermount sink with a pull-down faucet. Convenient 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)side-by-side refrigerator. . . Low-maintenance luxury vinyl plank flooring throughout the living areas, kitchen, laundry room, and bathrooms. Mohawk stain-resistant carpet in the bedrooms. 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 limited-lifetime warranty. Fully sodded homesite with Florida friendly landscaping and 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. For more information about this beautiful, professionally designed move-in ready home in Winter Haven, FL, call or email us today!
Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)
Listing Agent: George Lindsey, Iii (863-797-4999)
4099 ISLAND LAKES DR, WINTER HAVEN, FL 33881
$389,000449 Days on yellowkey MLS ID: P4934266
REDUCED by $5,000 (1.3%) on 05/28/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1603 Built: 2006Monthly Fee: $17 Tax: $5,194 (2024)Community: Island LakesSingle Family
Taxes:$5,194
Remarks: Virtually Staged. NEW ROOF 2/9/2026 + $5K PRICE IMPROVEMENT on 5/26! 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.
Listing Agent: Don Jerue (863-259-9550)
4045 GIORGIO DR, WINTER HAVEN, FL 33884
$300,9901 Day on yellowkey MLS ID: O6419297
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1665 Built: 2026Monthly Fee: $18 Tax: $3,147 (2025)Community: Villamar Phase 6 And Phase 6DSingle Family
Taxes:$3,147
Middle School: McLaughlin Academy Of Excellence
Remarks: Under Construction. Introducing the Harper floorplan at Villamar, where every square foot is put to use with sophistication and comfort. Inside this 4 bedroom, 2 bathroom home, you’ll find 1,665 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing granite and tile floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The chef's kitchen is a true highlight, boasting granite countertops, sleek stainless steel appliances, and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms provide flexibility for various lifestyles. The primary suite is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Like all homes in Villamar, the Harper includes all concrete block and also smart home technology, which allows you to control your home anytime with your smart device while near or away. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
516 REGGIE RD, WINTER HAVEN, FL 33884
$325,0001 Day on yellowkey MLS ID: O6418177
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2109 Built: 2024Monthly Fee: $16 Tax: $7,811 (2025)Community: Peace Crk ReserveSingle Family
Taxes:$7,811
Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Beautiful NEXT GENERATION HOME in the desirable Peace Creek Reserve community in Winter Haven! Built in 2024, this contemporary 4-bedroom, 3-bathroom residence offers the sought-after Freedom floor plan with a 2-car garage and 2,109 square feet of thoughtfully designed living space, blending modern style, energy efficiency, and comfortable living. A standout feature is the private Next Gen suite, complete with its own entrance, bedroom, living area, kitchenette, and washer and dryer hookup — ideal for multigenerational living, guests, or added flexibility. Inside the main residence, an open-concept layout seamlessly connects the kitchen, dining, and living areas, all enhanced by abundant natural light. The gourmet kitchen is designed for both everyday living and entertaining, featuring quartz countertops, stainless steel appliances, an oversized island, and a walk-in pantry. The spacious primary suite serves as a relaxing retreat with a private ensuite bath featuring dual sinks and a walk-in shower. Two additional generously sized bedrooms provide comfort and versatility for family members or guests. The covered patio extends the living space outdoors, creating the perfect setting for relaxing, everyday enjoyment, or entertaining family and friends on the weekends. Residents of Peace Creek Reserve enjoy resort-style amenities, including a community pool, playground, and scenic natural creek. Conveniently located near parks, recreational facilities, lakes, shopping, and dining, this home offers the perfect balance of small-town charm and modern conveniences in a peaceful setting.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
3600 JULIUS ESTATES BLVD, WINTER HAVEN, FL 33881
$340,000299 Days on yellowkey MLS ID: O6339978
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2526 Built: 2014Monthly Fee: $105 Tax: $3,256 (2024)Community: Lake Smart EstatesSingle Family
Taxes:$3,256
Remarks: AMAZING two-story home!!! Located in a BEAUTIFUL LAKEFRONT COMMUNITY! HUGE, fenced corner lot, very nice layout with a FLEX area/room that can be used as a formal Livingroom, office, or den, large master bedroom with a nice bathroom with dual sinks, walk in shower & walk-in closet, laundry room, 2 car garage & so much MORE**Seller may consider buyer's concessions **CALL YOUR AGENT FOR A PRIVATE SHOWING**
Listing is courtesy of: LUXURY REAL ESTATE GROUP LLC (561-929-7304)
Listing Agent: Gladys Falcon (863-812-1771)
1138 MICHELANGELO LN, WINTER HAVEN, FL 33884
$394,90075 Days on yellowkey MLS ID: S5147440
0 Days Off yellowkey (back on 6/23/2026)
REDUCED by $5,000 (1.3%) on 05/29/2026
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2386 Built: 2023Monthly Fee: $55 Tax: $4,275 (2025)Community: Estates/Lk FlorenceSingle Family
Taxes:$4,275
Remarks: Under contract-accepting backup offers. *** No CDD fees!!***Welcome to this stunning smart home offering the perfect blend of modern design, space, and functionality. This impressive two-story residence features 5 bedrooms, 3 full bathrooms, and a spacious 3-car garage, making it ideal for growing families or those who love to entertain. Step inside to discover a bright and open floor plan designed for today’s lifestyle. The main living areas flow seamlessly, creating the perfect space for gatherings, while large windows bring in abundant natural light. The modern kitchen serves as the heart of the home, featuring sleek finishes, ample cabinetry, and generous counter space for cooking and entertaining. With five generously sized bedrooms, there’s room for everyone—including a flexible space for guests, a home office, or multi-generational living. The primary suite offers a private retreat with a well-appointed en-suite bathroom and plenty of closet space. This home is equipped with smart home technology, providing convenience, efficiency, and peace of mind at your fingertips.Step outside and enjoy your own private outdoor retreat situated on a generous 0.24-acre lot, offering plenty of space for relaxation, play, or future customization. The covered back patio and screened enclosure create the perfect setting for year-round outdoor living—ideal for morning coffee, evening gatherings, or simply enjoying Florida’s beautiful weather without the bugs. Built in 2023, this home offers the advantages of newer construction without the wait, combining modern features with move-in ready convenience. Home is just minutes from Legoland and the sea life aquarium! Don’t miss the opportunity to own this beautifully designed home—schedule your private showing today!
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: David Hartigan (407-955-1156)
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