Location: Winter Haven
Keyword(s): Winter Haven Senior
Keyword(s) High School: Winter Haven Senior
Do Not Show Listings
256 MEREDITH BLVD, WINTER HAVEN, FL 33881
$374,99035 Days on yellowkey MLS ID: G5111558
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2531 Built: 2026Monthly Fee: $6 Tax: $500 (2024)Community: WillowbrookSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$500
Elementary School: Lake Alfred Elem
High School: Winter Haven Senior
Tax Year: 2024
Middle School: Denison Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning Winston floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 5-bedroom, 3-bath home offers 2,531 square feet of living space, and providing excellent curb appeal in it's elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz counter tops 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. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
268 MEREDITH BLVD, WINTER HAVEN, FL 33881
$299,99070 Days on yellowkey MLS ID: G5109922
0 Days Off yellowkey (back on 5/22/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1938 Built: 2025Monthly Fee: $6 Tax: $500 (2024)Community: Willowbrook NorthSingle Family
Elementary School: Fred G. Garnier Elem
Remarks: One or more photo(s) has been virtually staged. Welcome to the Mulberry floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2.5-bath home offers 1,938 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. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!
2213 ROSE BLVD, WINTER HAVEN, FL 33881
$289,90033 Days on yellowkey MLS ID: L4961368
0 Days Off yellowkey (back on 5/21/2026)
REDUCED by $10,000 (3.3%) on 05/14/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1851 Built: 2018Monthly Fee: $25 Tax: $2,962 (2025)Community: Buckeye RdgSingle Family
Taxes:$2,962
Elementary School: Elbert Elem
Tax Year: 2025
Remarks: Welcome to 2213 Rose Blvd in Winter Haven—a beautifully maintained and like-new 4 bedroom, 2 bath home offering over 1850 square feet of comfortable living within the Buckeye Ridge community. Perfectly positioned on a corner lot, this home showcases outstanding curb appeal and evident pride of ownership, enhanced by a freshly painted exterior accents, well cared for landscaping, decorative gable vents and carriage-style garage hardware for a custom look. A thoughtfully designed split-bedroom layout with open-concept living at its core, offering a seamless flow for everyday living and entertaining while maintaining privacy with a well-separated primary suite and generously sized secondary bedrooms. Tile flooring leads from the foyer into the great room and kitchen area, where brand-new wood laminate flooring and roomy dimensions provide an ideal level of easy living. The kitchen features an abundance of cabinetry and counter space, breakfast bar/center island, a walk-in pantry and included appliances. Dining space sits just off the kitchen with tranquil backyard views. The triple split-bedroom layout provides privacy and flexibility, highlighted by a generously sized primary suite with brand-new carpeting, a walk-in closet, and an en-suite bath complete with dual vanities, walk-in shower, large linen closet and private water closet. All guest bedrooms also have brand new carpeting and are spacious with easy access to the full guest bath. Step outside to your private outdoor oasis—featuring a screened patio that opens to a fully fenced backyard with vinyl fencing and irrigation system with timer to keep the yard green and lush—perfect for relaxing or hosting gatherings year-round. Additional notable features include an inside laundry room, double-pane windows, two-car garage, warranties on the new flooring, both gas and battery generator connections and a transfer switch for added peace of mind. Location is everything, and this home delivers—just minutes from vibrant downtown Winter Haven, Polk State College, medical facilities, shopping, restaurants as well as multiple golf courses and lakes to fully enjoy the Central Florida lifestyle. Centrally located between Orlando and Tampa, Winter Haven offers the perfect balance of small-town charm with convenient access to major roadways, shopping, dining, and world-class attractions. Homes in this condition with an ideal combination of upgrades and location are hard to find—schedule your private showing today!
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Michael Stone (863-412-9733)
1525 LEAMINGTON LN, WINTER HAVEN, FL 33884
$299,366365 Days on yellowkey MLS ID: L4952865
1 Days Off yellowkey (back on 5/21/2026)
REDUCED by $5,000 (1.6%) on 05/01/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2200 Built: 2025Monthly Fee: $67 Tax: $7,400 (2025)Community: Villa Mar Phase 3Single Family
Taxes:$7,400
Elementary School: Chain O Lakes Elem
Middle School: Berkley Accelerated Middle
Remarks: This 4 bedrooms and 3 bath Home begins with a 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 designated laundry room. 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)
2323 BRASSIE CT, WINTER HAVEN, FL 33884
$313,967227 Days on yellowkey MLS ID: L4956626
2 Days Off yellowkey (back on 5/21/2026)
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
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.
4622 CYPRESS GARDENS RD, WINTER HAVEN, FL 33884
$180,00063 Days on yellowkey MLS ID: S5146684
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1706 Built: 1985 Tax: $3,238 (2025)Community: Silver Oaks VillasSpa: NoSingle Family
Taxes:$3,238
Elementary School: Garden Grove Elem
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)
6710 WINTERSET GARDENS RD, WINTER HAVEN, FL 33884
$535,00025 Days on yellowkey MLS ID: P4938608
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2268 Built: 2017Monthly Fee: $8 Tax: $3,349 (2025)Community: Winterset GardensSingle Family
Taxes:$3,349
Remarks: CUSTOM BUILT POOL HOME IN WINTERSET GARDENS WITH CHAIN OF LAKES ACCESS. Welcome to this beautifully maintained, one-owner custom home located in desirable, lake front Winterset Gardens. This spacious 4-bedroom, 3-bath residence is directly across the street from little Lake Winterset and features 10 foot ceilings, 8 foot custom doors and two true master suites (One with attached pool bathroom), each with walk-in closets, offering flexible living for multi-generational families or guests. Built with quality and efficiency in mind, the home includes a 45-year architectural shingle roof, foam-filled concrete exterior walls, and extra attic insulation. Inside, you’ll find wood plank tile flooring throughout, Level 3 granite surfaces, and semi-custom solid wood cabinetry with dovetail soft-close drawers in the kitchen, bathrooms, and spacious indoor laundry room. The kitchen is equipped with matching LG appliances, under-cabinet lighting, and a Delta touch faucet. Custom craftsmanship is showcased throughout with professionally trimmed 8ft. doors and windows, shiplap accent walls in the dining area, kitchen, and island, plus a stunning custom electric fireplace with mantel, hearth, and barn door cabinetry in the living room. The primary suite also features a matching custom shiplap electric fireplace for added comfort and style. Step outside to your fully fenced private backyard retreat featuring a saltwater pool with a variable speed pump, paver deck and pre-installed footers for a future pool enclosure. The covered lanai is designed for entertaining with an outdoor kitchen including grill, refrigerator, storage, and matching Level 3 granite. Enjoy the motorized screen, tongue and groove wood ceilings, and ambient lighting for the perfect indoor-outdoor experience. Additional highlights include Permanent app-controlled exterior lighting, Sprinkler system on well, leased water filtration and softener, Triple sliding glass doors that retract to fully open to the patio to the living area, Pre-wired surround sound system in living room, primary bedroom, and patio, Upgraded DC motor ceiling fans throughout, Tiled showers to the ceiling with rain shower in primary bath, Framed bathroom mirrors and comfort-height elongated toilets, Custom garage cabinetry, sealed floors, and hot/cold water hookup. Winterset Gardens is a highly respected, quaint neighborhood on the shore of Little lake Winterset and offers an optional $100 HOA with a community boat ramp and no deed restrictions allowing direct access to The world renowned Winter Haven Chain of Lakes. 24 canal connected lakes offering great fishing, skiing and leisure boating. Hop on your boat from your neighborhood and go get a bite to eat at several float up bars and restaurants. This home combines thoughtful and impressive upgrades, energy efficiency, and custom design in a highly sought-after location. Truly move-in ready and built to impress.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY (833-765-3244)
Listing Agent: Brad Martin (863-307-5074)
850 LAKE ELBERT PARK NE, WINTER HAVEN, FL 33881
$267,90044 Days on yellowkey MLS ID: S5148051
1 Days Off yellowkey (back on 5/20/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1781 Built: 1980 Tax: $4,590 (2025)Community: Elbert ParkSingle Family
Taxes:$4,590
Remarks: One or more photo(s) has been virtually staged. Spacious 1-story home located in the Elbert Park subdivision of Winter Haven! This property features 3 bedrooms and 2 full bathrooms, offering a functional layout with great potential. The large living room showcases high ceilings, exposed wood beams, ceramic tile flooring, and a wood-burning fireplace—ideal for gatherings and everyday living. The dining area flows seamlessly onto a large screened patio, providing a great space to relax or entertain. The kitchen offers ample space and is ready for your personal updates to create the home you’ve been envisioning. Step outside to enjoy the fully fenced backyard, complete with a large shed for additional storage. Conveniently located near Lake Elbert and Rotary Park, this home offers easy access to outdoor recreation. Don’t miss this opportunity to add value and make this home your own—schedule your private showing today before it’s gone!
2085 ISLE ROYALE CT SE #284, WINTER HAVEN, FL 33880
$124,999111 Days on yellowkey MLS ID: O6380383
REDUCED by $1 (0.0%) on 04/22/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 648 Built: 2004Monthly Fee: $270 Tax: $213 (2025)Community: Park LakeCondo
Taxes:$213
Elementary School: John Snively Elem
Remarks: CORNER UNIT WITH VAULTED CEILINGS AND PRIVATE BALCONY- Welcome to your new retreat in the highly sought-after chain of lakes community of Park Lake — where comfort, style, and location come together beautifully. Step inside this charming one-bedroom, one-bath home and you’ll immediately notice the open feel created by vaulted ceilings and luxury vinyl flooring throughout the main living areas. The kitchen is a true highlight, featuring quartz countertops, sleek cabinets, stylish backsplash a modern tile floor, and all-new stainless steel appliances — including a five-burner stove, low-profile microwave, and refrigerator with exterior ice-maker. Thoughtful upgrades like new sinks, faucets, a garbage disposal, and modern lighting add both function and sophistication. The bathroom feels spa-like with a sleek tile shower, coordinating tile floor, quartz countertop, new sink, fixtures, and an elegant multi-illuminating with anti fog mirror that provides perfect lighting for any time of day. Two sliding glass doors — one from the living room and another from the bedroom — open to your private screened balcony, filling the home with natural light and offering peaceful outdoor views. The spacious bedroom includes a large closet, providing plenty of storage. This home also features a 2026 hot water heater, 2021 roof, and 2017 AC- offering peace of mind for years to come. Updated blinds, modern ceiling fans, and an inside utility with a washer/dryer combo add even more comfort and convenience. Just five minutes from vibrant downtown Winter Haven and next door to the state-of-the-art Advent Health Field House — complete with basketball courts and an Olympic-size swimming pool — this home’s location can’t be beat. Park Lake sits on the shores of beautiful Lake Lulu, where residents can fish from the pier or enjoy skiing right on the water. Perfectly centered near shopping, dining, and grocery stores, this prime location truly offers it all — comfort, convenience, and the best of the Florida lifestyle. Listing agent is owner. Seller Financing Available.
Listing is courtesy of: LIONHEART BROKERS (321-214-4640)
Listing Agent: Claudia Centesimo (407-383-8882)
15 LAKE HOWARD DR NW, WINTER HAVEN, FL 33880
$250,00054 Days on yellowkey MLS ID: TB8493899
Bed: 6 Bath: 4.0 Liv Area Sq Ft: 2883 Built: 1920 Tax: $5,897 (2025)Community: Leonards SubSingle Family
Taxes:$5,897
Elementary School: Inwood Elem
Middle School: Westwood Middle
Remarks: This expansive property is a true diamond in the rough, perfectly positioned for the savvy investor looking for a great return on a "buy and hold" scenario or a strategic value-add project. Boasting a generous 0.41-acre lot, this property is designed for versatility. With a massive layout featuring 6 bedrooms and 4 bathrooms, the home offers the unique potential for 3 or even 4 separate doors (units), making it an ideal candidate for a multi-generational living setup or a high-performing rental portfolio addition. Only 12 minutes away from LEGOLAND!
Listing is courtesy of: MARZUCCO REAL ESTATE (813-679-1365)
Listing Agent: Clarisa Moody (813-446-2003)
737 SANTA MARIA DR, WINTER HAVEN, FL 33884
$478,00038 Days on yellowkey MLS ID: P4938535
1 Days Off yellowkey (back on 5/10/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2571 Built: 1993Monthly Fee: $46 Tax: $3,220 (2025)Community: Overlook EstatesSingle Family
Taxes:$3,220
Remarks: Already appraised for the listing price, this home is a great opportunity for massive savings every month on utility bills. Current owners typical electric bill in heat of summer is approx. $16 Solar panels WILL be PAID IN FULL by Sellers at closing. 4 BR/2.5 BA w/NEW ROOF 2025, NEW AC 2024. Durable porcelain wood plank-look floors throughout. Stone, wood burning fireplace in great room. Very private, screened 32 x 16 HEATED pool with large covered seating area, cabana bath, outdoor shower and and roomy storage. Well established, small gated community convenient to shopping, downtown WH, chain-of-lakes recreation. Easy going HOA. Pet friendly! Safe concrete block/stucco construction and NO CDD. Don't miss this opportunity to protect yourself from future electric rate hikes. It's move in ready!
Listing is courtesy of: PROPERTY MANAGEMENT OF POLK (863-259-4600)
Listing Agent: Julie Phillips (561-906-1118)
1507 FOXRIDGE RUN SW, WINTER HAVEN, FL 33880
$245,00019 Days on yellowkey MLS ID: O6405110
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1148 Built: 1977 Tax: $2,861 (2025)Community: NaSpa: NoSingle Family
Taxes:$2,861
Elementary School: Lake Shipp Elem
Remarks: Under contract-accepting backup offers. Welcome to this charming and move-in ready 3-bedroom, 2-bath home located in the established Foxridge community of Winter Haven. Featuring approximately 1,148 square feet of living space, this cozy residence offers a functional split-bedroom floor plan, spacious living area, and plenty of natural light throughout. The kitchen provides ample cabinet space and flows nicely into the dining area, making it perfect for everyday living or entertaining. Situated on a generously sized lot with a private backyard, there’s plenty of room to relax, garden, or enjoy outdoor gatherings. Conveniently located near shopping, dining, schools, and major roadways with easy access to all that Winter Haven has to offer. Whether you're a first-time homebuyer, or looking to downsize, this property is a fantastic opportunity to own an affordable home in Central Florida.
Listing is courtesy of: CITARELLI REALTY GROUP LLC (321-607-3586)
Listing Agent: Benjamin Crane (302-841-8999)
231 AVENUE A NE, WINTER HAVEN, FL 33881
$210,00050 Days on yellowkey MLS ID: L4960914
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1144 Built: 1920 Tax: $2,944 (2025)Community: Winter Haven HeightsSingle Family
Taxes:$2,944
Elementary School: Frank E. Brigham Academy
Remarks: One or more photo(s) has been virtually staged. One or more photos have been virtually staged. 1920s home for sale in Winter Haven with original hardwood floors, updated functionality, and R-3 zoning potential in one of Central Florida’s fastest-growing real estate markets. This move-in ready property offers flexible living space, investment potential, and convenient access to shopping, dining, parks, and the Winter Haven Chain of Lakes. The home features a bright tiled foyer with a large coat closet and direct access to a front bedroom ideal for a home office, guest room, or flex space. The main living and dining areas feature original hardwood flooring and an open layout designed for comfortable living and entertaining. The kitchen includes a refrigerator, range, microwave, and dishwasher for everyday convenience. The split-bedroom floor plan provides added privacy, with the primary suite separated from the secondary bedroom. A bonus flex area near the primary bedroom is ideal for a home office, nursery, gym, or media space. A rear Florida room adds additional square footage and direct driveway access, creating extra space for entertaining, relaxing, or indoor-outdoor living. The R-3 zoning offers added value for investors, rental property buyers, or those exploring future development opportunities. Buyers should verify zoning, permitted uses, and redevelopment options with the City of Winter Haven. Located near downtown Winter Haven, Legoland Florida, major highways, medical facilities, and the Chain of Lakes, this Central Florida property combines location, flexibility, and long-term value. Schedule your private showing today.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Michael Hochadel (863-604-0018)
2165 CASTLE PT #2165, WINTER HAVEN, FL 33880
$155,00012 Days on yellowkey MLS ID: S5150150
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1128 Built: 1981Monthly Fee: $135 Tax: $256 (2025)Community: StonebridgeSpa: YesCondo
Taxes:$256
Remarks: Located just 15minutes from Legoland Park, Welcome to this beautifully maintained home, new roof, located in a desirable and quiet community in Winter Haven. This property offers a functional and modern layout designed for comfortable living, featuring bright open spaces and a seamless flow between the living, dining, and kitchen areas. The kitchen is well-appointed with ample cabinetry and workspace, perfect for everyday living and entertaining. The bedrooms are generously sized, providing comfort and privacy, while the primary suite offers a relaxing retreat. Enjoy a spacious yard ideal for outdoor activities, gatherings, or future enhancements. Conveniently located near major highways, shopping centers, dining, schools, and entertainment, this home combines comfort with accessibility. Whether you're a first-time buyer, investor, or looking to relocate, this property presents an excellent opportunity in the growing Winter Haven area.
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Yoja Mirabal (407-543-7789)
4009 CYPRESS LNDG S, WINTER HAVEN, FL 33884
$230,00074 Days on yellowkey MLS ID: TB8487328
0 Days Off yellowkey (back on 5/19/2026)
REDUCED by $9,000 (3.8%) on 05/09/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1291 Built: 1987Monthly Fee: $83 Tax: $3,230 (2025)Community: Cypress Landing Ph 02Single Family
Taxes:$3,230
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Newly renovated 2 bedroom, 2 bathroom home with all the major updates already done for you — new roof, new floors ,new AC, and new water heater. This is a boater and fisher’s dream property located on beautiful Lake Dexter, Enjoy boating, water skiing, and freshwater fishing right from your backyard playground. The community offers a dock with boat slips available on a first-come, first-served basis, perfect for boats up to 24 feet. Residents also enjoy a clubhouse, pickleball courts, and tennis courts, making it easy to enjoy the Florida lifestyle. Whether you're looking for a full-time residence or a weekend lake retreat, this home offers the perfect mix of updates, amenities, and waterfront living.
Listing is courtesy of: ELEVE REAL ESTATE LLC (813-562-5002)
Listing Agent: Danielle Davis (813-526-5002)
2779 ADELINE AVE, WINTER HAVEN, FL 33881
$293,740121 Days on yellowkey MLS ID: O6378154
2 Days Off yellowkey (back on 5/19/2026)
INCREASED by $1,000 (0.3%) on 05/08/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1498 Built: 2025Monthly Fee: $8 Tax: $3,456 (2025)Community: Willowbrook SouthSingle Family
Taxes:$3,456
Remarks: Under Construction. The Freeport II floor plan at Willowbrook South offers the perfect blend of comfort, functionality, and modern design. Built with durable all-concrete block construction, this one-story home maximizes living space with a bright, open-concept layout that’s ideal for everyday living and entertaining. As you enter through the foyer, you’ll find two spacious guest bedrooms and a full guest bath with a modern vanity. A convenient linen closet is positioned between the bathroom and bedrooms for easy storage. Further down the hallway, a third bedroom offers flexibility for a home office or guest space, alongside a private laundry area and direct access to the two-car garage. The heart of the home features a well-appointed kitchen with stainless steel appliances, overlooking the dining area, great room, and covered patio perfect for gatherings and family time. Tucked at the rear of the home, the primary bedroom offers a peaceful retreat with a walk-in closet and a spa-inspired bathroom featuring a double vanity sink and a spacious shower. Every home in Willowbrook South comes equipped with the Home Is Connected Smart Home Technology package, allowing you to control locks, thermostat, and more right from your smartphone whether you’re home or away. With its thoughtful design and modern features, the Freeport makes owning a new home in Winter Haven, FL both easy and enjoyable. *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)
264 MEREDITH BLVD, WINTER HAVEN, FL 33881
$279,99075 Days on yellowkey MLS ID: G5109678
0 Days Off yellowkey (back on 3/16/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1598 Built: 2025Monthly Fee: $6 Tax: $500 (2025)Community: Willowbrook NorthSingle Family
Remarks: Welcome to this stunning Dream Finders Bradley 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 1,589 square feet of living space and boasts excellent curb appeal due to its impressive elevation. Inside, you'll find gorgeous Gray 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.
3307 COSTELLO CIR, WINTER HAVEN, FL 33884
$294,90026 Days on yellowkey MLS ID: L4961494
REDUCED by $5,000 (1.7%) on 05/18/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1553 Built: 2023Monthly Fee: $17 Tax: $4,645 (2025)Community: Villamar Ph FourSingle Family
Taxes:$4,645
Remarks: New to market with a new price in Central Florida. This move-in ready home offers a spacious open-concept layout with high ceilings and a clean, well-maintained interior throughout. Recent updates include the removal of all carpeting and replacement with durable vinyl flooring in the bedrooms, along with luxury vinyl plank flooring in the main living areas, bathrooms, and laundry room. The interior has also been freshly painted, creating a bright and modern feel. The kitchen is thoughtfully designed with quartz countertops, upgraded espresso cabinetry with crown molding, a center island with sink, and Samsung stainless steel appliances. The primary suite features dual vanities, a walk-in closet, and a private en-suite bath. Additional highlights include a whole-home water softener and filtration system, custom-fit blinds, ceiling fans, washer and dryer, and a programmable thermostat. Exterior improvements include a fully fenced backyard with new irrigation and landscaping, providing a functional and inviting outdoor space. The home is also equipped with a Ring doorbell system, which convey wiih the property. Additional features include architectural shingles, energy-efficient insulation and windows, a covered front entry, rear/side patio, and a two-car garage with remote access. Community amenities include a pool and playground. Conveniently located and offered in move-in ready condition. Schedule a private showing to experience this home in person.
1246 31ST ST NW, WINTER HAVEN, FL 33881
$165,900114 Days on yellowkey MLS ID: TB8470610
4 Days Off yellowkey (back on 5/18/2026)
REDUCED by $4,000 (2.4%) on 04/02/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 840 Built: 1961 Tax: $1,157 (2024)Community: West Cannon HeightsSpa: NoSingle Family
Taxes:$1,157
Remarks: Under contract-accepting backup offers. Welcome to this charming 2-bedroom, 1-bathroom home in the West Cannon Heights neighborhood of Winter Haven, an excellent opportunity for first-time buyers or investors. With a really large open kitchen, this home is move-in ready. The exterior features a covered parking area and a workshop with a new roof. This property offers a cozy living space and a convenient location, with no HOA fees. Don't miss the chance to own this piece of Winter Haven.
Listing is courtesy of: PEOPLE'S CHOICE REALTY SVC LLC (813-933-0677)
Listing Agent: Pablo Lluveras Matos (813-406-3652)
3180 COUNTRY CLUB CIR, WINTER HAVEN, FL 33881
$260,000128 Days on yellowkey MLS ID: W7882124
INCREASED by $10,000 (4.0%) on 05/18/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1732 Built: 2019Monthly Fee: $30 Tax: $4,663 (2025)Community: Country Walk/Winter HavenSingle Family
Taxes:$4,663
Remarks: Short Sale. APPROVED SHORT SALE AT PRICE! CHAPTER 7 BANKRUPTCY - Located In The Country Walk Community, This 2019 Built Home At 3180 Country Club Cir, Winter Haven, FL 33881 Features The Popular DR Horton Aria Floor Plan Offering 3 Bedrooms, 2 Bathrooms, & 1,672 Sq Ft Of Living Space. This Home Offers an Open Concept Layout With A Spacious Living Area, Split Bedroom Floor Plan, & a Functional Kitchen Overlooking The Main Living Space. Fenced Yard. Ideal For Everyday Living And Entertaining. Built In 2019, Conveniently Located Near Shopping, Dining, Schools, And Major Roadways With Easy Access Throughout Winter Haven. Bankruptcy Short Sale — Third-Party Approval Required. Property Sold As-Is. Great Opportunity For Owner-Occupants Or Investors Seeking Value In A Growing Area. Call Today For Details Or To Schedule A Private Showing.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Jon Mccall, Pa (352-725-7206)
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