Location: Winter Haven , 33884
Do Not Show Listings
3588 RALEIGH DR, WINTER HAVEN, FL 33884
$262,500116 Days on yellowkey MLS ID: L4959265
REDUCED by $6,000 (2.2%) on 05/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1719 Built: 2007Monthly Fee: $485 Tax: $1,555 (2025)Community: Traditions Ph 02Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,555
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to 3588 Raleigh Dr! Located within the gated 55+ community of Traditions, this well-maintained corner-lot home offers a blend of comfort, functionality, and resort-style living. The residence features two bedrooms, two bathrooms, and more than 1,700 square feet of open living space designed to accommodate both everyday living and entertaining. It boasts an open floor plan with spacious living & dining areas flowing directly into the fully equipped kitchen. The entire area creates the heart of the home and lends ample room for gathering. Each bedroom is spacious and a split layout provides privacy for everyone. You'll especially love the master suite which has brand new carpet, a walk-in closet, a full private bathroom with dual sink vanity, a step-in shower, and a siding glass door leading out to the lanai. An enclosed lanai extends the living space and offers a relaxing spot to enjoy the outdoors year-round. A pavered courtyard with established landscaping adds privacy and a peaceful atmosphere. Major system updates include a new roof (2023), water heater (2023), and A/C (2021). Traditions offers an impressive selection of amenities, highlighted by a 19,000-square-foot lakefront clubhouse featuring a heated swimming pool, spa, fitness center, sauna, billiards room, craft rooms, library, and ballroom. Residents also enjoy walking trails, tennis and pickleball courts, shuffleboard, and basketball courts. Direct lake access includes a community boat ramp and docks, ideal for boating and fishing enthusiasts. The monthly HOA fee includes lawn maintenance, cable, internet, and exterior home painting, supporting a low-maintenance lifestyle. Located close to Hwy 27, golf courses, restaurants, and anticipating a brand new Publix just around the corner, this place truly offers Adult Florida living lifestyle at its finest!
Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)
Listing Agent: Cindy Strouse (863-581-1605)
3322 OAK HILL PL, WINTER HAVEN, FL 33884
$333,00035 Days on yellowkey MLS ID: O6404080
REDUCED by $4,000 (1.2%) on 05/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2109 Built: 2006Monthly Fee: $155Community: Oakgrove SubSingle Family
Taxes:$0
Remarks: WELCOME HOME to this beautifully updated 3-bedroom, 2-bath residence located in the pristine gated community of Cypresswood! From the moment you enter the neighborhood, you’ll feel the charm of this private, resort-style community nestled in the heart of Polk County—just minutes from US Hwy 27, providing easy access to all that Central Florida has to offer. Step through the front door into a grand foyer with soaring ceilings that opens to a spacious, light-filled living room—perfect for entertaining guests or enjoying quiet evenings at home. The kitchen is designed to impress, featuring beautiful cabinetry, abundant pantry space, and brand-new stainless steel appliances that elevate both style and functionality. Just off the kitchen, the oversized laundry room offers even more storage along with a convenient laundry sink. On the opposite side, a charming breakfast nook overlooks the large backyard—ideal for morning coffee or casual dining. The generously sized primary suite is a true retreat, complete with an expansive walk-in closet, dual vanities, a walk-in shower, and private access to the screened lanai—perfect for enjoying Florida evenings. Bedrooms two and three both feature double closets, providing plenty of storage space for family or guests. Major updates give you peace of mind for years to come, including the roof (2021), new A/C (2024), gas water heater 2021, new stainless appliances. This move-in-ready gem offers comfort, style, and thoughtful upgrades in one of the area’s most desirable golf communities which include an 18 hole champion designed course, pro shop, wellness center, Pub/restaurant, clubhouse, swimming pool and more! Don’t miss your opportunity to make it yours—schedule your private showing today!
Listing is courtesy of: INFINITE REAL ESTATE POWERED BY ILIST (321-689-8731)
Listing Agent: Michelle Keohane (850-866-5905)
1864 EMILY DR, WINTER HAVEN, FL 33884
$292,900205 Days on yellowkey MLS ID: TB8447490
REDUCED by $1,000 (0.3%) on 05/07/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1836 Built: 2005Monthly Fee: $25 Tax: $3,788 (2024)Community: Emily EstatesSingle Family
Taxes:$3,788
Tax Year: 2024
Remarks: Welcome to your dream home in the highly desirable community of Emily Estates! This stunning, move-in-ready 4-bedroom, 2-bathroom residence has been beautifully refreshed with brand-new interior and exterior paint, sparkling new stainless steel appliances, and upgraded plumbing fixtures throughout—giving it the crisp, clean feel of a brand-new build. You will love the light and bright open-concept floor plan, which perfectly channels natural sunlight across the spacious main living areas. The kitchen is a chef's delight, boasting ample cabinet and counter space, a convenient breakfast bar, and durable ceramic tile flooring throughout for effortless maintenance. Step outside to an expansive backyard with endless possibilities—perfect for a playground, hosting weekend BBQs, or simply relaxing in the Florida sunshine. Nestled in a fantastic, quiet neighborhood just minutes from premier shopping, dining, and the excitement of Legoland, this turnkey home offers the perfect blend of comfort and convenience. schedule your tour today!
Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-531-2006)
Listing Agent: Octavia Cheveresan (727-403-8948)
1525 LEAMINGTON LN, WINTER HAVEN, FL 33884
$299,366371 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
High School: Winter Haven Senior
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
$313,967233 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.
1340 DAISY FIELD DR, WINTER HAVEN, FL 33884
$310,000309 Days on yellowkey MLS ID: O6331865
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1882 Built: 2024Monthly Fee: $69 Tax: $2,968 (2025)Community: Harmony On Lake EloiseSingle Family
Taxes:$2,968
Remarks: SELLER MOTIVATED!!! Welcome to this stunning corner-lot home located in the desirable community of Harmony on Lake Eloise — just minutes from LEGOLAND and perfectly situated between Tampa and Orlando! This beautifully designed property offers a modern open-concept floor plan ideal for today’s lifestyle. Step inside to find elegant shaker-style cabinets, quartz countertops, and a stainless-steel range hood vented to the exterior. The kitchen is fully equipped with Whirlpool stainless-steel appliances including range, dishwasher, refrigerator, washer, and dryer — all included! The spacious layout provides comfort and style with thoughtful upgrades throughout. The large corner lot offers a generous backyard, perfect for entertaining, relaxing, or even building your dream outdoor space. Built with quality in mind, the home features block-on-block construction, architectural shingles, and a sleek stucco exterior for long-lasting durability and curb appeal. Inside, integrated smart home technology allows you to control lighting, temperature, and more — all from the palm of your hand. Living in Harmony on Lake Eloise means enjoying Florida’s outdoor lifestyle with access to the Chain of Lakes, nearby parks, shopping centers, restaurants, and golf courses. Plus, with easy access to major highways, commuting is a breeze. Don’t miss your chance to own this move-in-ready home in one of Central Florida’s most convenient and charming communities!
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Antonio Chacon (407-227-4683)
1109 BRIMSTONE CIR, WINTER HAVEN, FL 33884
$324,900172 Days on yellowkey MLS ID: L4957925
REDUCED by $5,100 (1.5%) on 05/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1697 Built: 2023Monthly Fee: $30 Tax: $3,769 (2025)Community: Harmony/Lk Eloise Ph 1Spa: NoSingle Family
Taxes:$3,769
Remarks: Seller is providing up to $10,000 in concessions toward Buyer’s closing costs, prepaid items, or an interest rate buy-down (subject to lender approval). Location, Location, Location! Welcome to this beautifully upgraded D.R. Horton home, enhanced with extensive custom finishes and thoughtful owner improvements throughout. Fresh interior and exterior paint complement crown molding, recessed lighting, updated decorative light fixtures, ceiling fans, French doors, and a modern glass front entry door. Window treatments throughout provide both style and convenience. The open-concept kitchen features stainless steel appliances, a large island, pantry, upgraded lighting, an under-sink Reverse Osmosis drinking water filtration system, and a whole-home water treatment system. Bathrooms have been tastefully updated with upgraded mirrors, modern hardware, high-efficiency toilets, and an added vanity in the secondary bathroom. The spacious primary suite offers a walk-in closet, dual sinks, and a walk-in shower. Outdoor living is equally impressive with a covered rear patio featuring an added swing, enhanced landscaping, rear irrigation, installed gutters, and updated exterior lighting. Additional highlights include an indoor laundry room and a 2-car garage. Located in the master-planned community of Harmony at Lake Eloise, residents currently enjoy a community pool, sidewalks throughout the neighborhood, scenic walking paths around ponds, and a designated bike accessway. Future community plans include a proposed lakefront amenity center on Lake Eloise and a planned commercial district with neighborhood shops (subject to development timelines and approvals). Conveniently situated near LEGOLAND Florida Resort, the AdventHealth Fieldhouse and Conference Center, and the Freedom Boat Club Winter Haven – Lake Eloise location nearby—providing an additional boating lifestyle option through membership. Additional sports and recreation facilities are planned nearby, including four collegiate-level baseball fields projected to generate significant economic activity for the City of Winter Haven based on publicly discussed plans. Cypress Junction Montessori is planned nearby and is currently accepting enrollment for 2026. Polk County has also begun clearing and dredging efforts at nearby Lake Lulu, with discussions suggesting a future canoe and kayak launch and park area (subject to county completion and final designation). With continued infrastructure investment and future recreational enhancements planned throughout the area, Harmony at Lake Eloise continues to position itself as one of Winter Haven’s most exciting and growing communities.
Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)
Listing Agent: John Calhoun (863-528-7973)
6441 DOMIZIO DR, WINTER HAVEN, FL 33884
$299,49049 Days on yellowkey MLS ID: O6400090
1 Days Off yellowkey (back on 5/20/2026)
REDUCED by $5,000 (1.6%) on 05/12/2026
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2326 Built: 2026Monthly Fee: $53 Tax: $32 (2025)Community: Villa Mar 40'SSingle Family
Taxes:$32
Elementary School: Pinewood Elem
High School: Lake Region High
Middle School: Denison Middle
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)
116 HAMPDEN RD, WINTER HAVEN, FL 33884
$249,900217 Days on yellowkey MLS ID: S5137660
21 Days Off yellowkey (back on 5/21/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2225 Built: 1966 Tax: $4,494 (2024)Community: Dugger RepSingle Family
Taxes:$4,494
Remarks: Under contract-accepting backup offers. Short Sale. ***THIS IS AN UNAPPROVED SHORT SALE TRANSACTION*** Spacious 4/2 with a duplex layout. an impressive 12,000sqft+ lot that includes a covered back patio, nice sized pool, and detached garaged. Property needs new roof, pool work, and a variety of other repairs throughout the property. Tenant occupied. 24hr notice needed
Listing is courtesy of: TOWER TEAM REALTY, LLC (786-233-4959)
Listing Agent: Brandon Ford (305-305-0105)
6212 BOTTICELLA BLVD, WINTER HAVEN, FL 33884
$289,49044 Days on yellowkey MLS ID: O6401328
REDUCED by $5,000 (1.7%) on 05/12/2026
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2112 Built: 2026Monthly Fee: $53 Tax: $32 (2025)Community: Villa Mar 40'SSingle Family
Remarks: Under Construction. The first floor of the stunning Edison two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom. 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.
543 TERRANOVA CIR, WINTER HAVEN, FL 33884
$399,90095 Days on yellowkey MLS ID: L4959863
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2118 Built: 2003Monthly Fee: $67 Tax: $1,923 (2025)Community: Terranova Ph 01Spa: NoSingle Family
Taxes:$1,923
Remarks: POOL Home on Pond in TERRANOVA! Located in desirable southeast Winter Haven, this home has it all! Large areas overlooking screened pool and pond frontage and views! Enjoy the security of a gated community close to schools, shopping, churches and LEGOLAND! Call for your private showing today!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Steve Lockhart (863-289-9801)
3865 GIORGIO DR, WINTER HAVEN, FL 33884
$328,48016 Days on yellowkey MLS ID: TB8508578
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1695 Built: 2026Monthly Fee: $154 Tax: $1 (2026)Community: VillamarSpa: NoSingle Family
Taxes:$1
Tax Year: 2026
Remarks: Under Construction. Brand new, energy-efficient home available by Jul 2026! Open kitchen flows to the dining space, great room and outside patio. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.
Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)
Listing Agent: Bryan Sumner (813-336-5895)
340 VAIL DR, WINTER HAVEN, FL 33884
$365,000127 Days on yellowkey MLS ID: S5142678
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2042 Built: 1984Monthly Fee: $17 Tax: $3,946 (2025)Community: Cedar Cove Ph 01Single Family
Taxes:$3,946
Remarks: One or more photo(s) has been virtually staged. Beautifully updated home tucked away on a quiet cul-de-sac in the well-established Cedar Cove community, just moments from the scenic shores of Lake Eloise. Set on over a quarter-acre lot, this property offers more than 2,000 sq ft of thoughtfully designed living space, featuring 3 bedrooms, 3 full bathrooms, and an enclosed bonus room that can easily function as a 4th bedroom. Inside, bright formal living and dining areas flow effortlessly into a spacious open-concept kitchen, recently remodeled with granite countertops, modern shaker-style cabinetry, and stainless steel appliances. Dual breakfast bars overlook the inviting family room and dining space, creating the perfect setup for entertaining or everyday living. The family room impresses with soaring ceilings and a striking stone wood-burning fireplace, while luxury vinyl plank flooring and upgraded bathroom vanities elevate the home’s style throughout. A convenient third full bath located near the laundry area is ideal for guests or for future pool-day use, just imagine the possibilities. Step out onto the screened porch and enjoy a generously sized backyard—perfect for gatherings or peaceful relaxation. Additional highlights include an oversized garage with ample storage and workspace, brand-new windows for enhanced energy efficiency and natural light, plus a newer roof and A/C system for added peace of mind. Ideally located near local amenities, downtown Winter Haven, and Legoland, with world-famous theme parks just 40 miles away, this home truly has it all. Don’t miss this rare opportunity to own a standout home in one of Winter Haven’s most desirable neighborhoods!
Listing is courtesy of: EXIT REALTY 4CORNERS (863-344-3948)
Listing Agent: Carlos Dejesus (407-818-6868)
737 SANTA MARIA DR, WINTER HAVEN, FL 33884
$478,00044 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
Elementary School: Elbert Elem
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)
44 LAKE ELOISE CT, WINTER HAVEN, FL 33884
$619,50035 Days on yellowkey MLS ID: P4938605
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2916 Built: 1989Monthly Fee: $42 Tax: $4,168 (2025)Community: Harbour EstatesSingle Family
Taxes:$4,168
Remarks: BEAUTIFUL SE POOL HOME LOCATED ON A QUIET CUL-DE-SAC IN DESIRABLE HARBOR ESTATES. SITUATED ON A SPACIOUS WOODED LOT OF OVER 1/2 ACRE. THIS PROPERTY OFFERS PRIVACY, MATURE LANDSCAPING AND PLENTY OF OUTDOOR LIVING SPACE FOR ENTERTAINING OR FOR THOSE FAMILY GATHERINGS. THIS HOME FEATURES 4BR PLUS A PRIVATE GUEST BEDROOM AND BATH, IDEAL FOR GUESTS, MULTI GENERATIONAL LIVING OR FLEXIBLE HOME OFFICE SPACE. ENJOY THIS 38X10 LANAI OVERLOOKING THE SCREEN ENCLOSED POOL, PERFECT FOR ENTERTAINING AND RELAXING YEAR ROUND. LARGE ENTRY FOYER WITH FORMAL LIVING ROOM WITH FIREPLACE, PLANTATION SHUTTERS THROUGHOUT. FORMAL DINING ROOM FOR THOSE FAMILY DINNERS. LARGE OPEN KITCHEN WITH ABUNDANCE OF CABINETS, LARGE CENTER ISLAND WITH GRANITE COUNTERTOPS AND STAINLESS APPLIANCES, A CHEF'S DELIGHT. 20 X 16 FAMILY ROOM WITH FULL STORAGE WALL. SPACIOUS PRIMARY BEDROOM HAS MASTER BATH WITH DOUBLE VANITIES AND STEP IN SHOWER. WALK IN CLOSET WITH ORGANIZER SHELVING. DON'T NEED TO FORGET ... THE OVERSIZED SIDE ENTRY GARAGE HAS A MINI SPLIT AC UNIT AND HAS PREVIOUSLY COOLED THE SPACE FOR AN ART STUDIO, SO MANY POSSIBILITIES. THIS HOME IS CONVENIENTLY LOCATED NEAR SHOPPING, DOWNTOWN EVENTS, RESTAURANTS AND NEAR AREA LAKES ON OUR FAMOUS WINTER HAVEN CHAIN OF LAKES. THIS IS A RARE OPPORTUNITY TO OWN A HOME IN ONE OF OUR SE WINTER HAVEN'S MOST ESTABLISHED COMMUNITIES.
Listing is courtesy of: FLORIDA HOME CHOICE REALTY (863-412-2727)
Listing Agent: Glenda Pruitt (863-412-2727)
10 ENCLAVE DR, WINTER HAVEN, FL 33884
$234,00022 Days on yellowkey MLS ID: P4938719
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1368 Built: 1996Monthly Fee: $435 Tax: $1,981 (2025)Community: Cypresswood Enclave Ph 01Townhouse
Taxes:$1,981
Remarks: WELCOME TO THIS CHARMING TOWNHOUSE located in the sought-after Cypresswood Golf & Country Club community in beautiful Winter Haven! This inviting 2 BD / 2 BA home offers comfortable Florida living with a spacious open-concept living and dining room combination, abundant natural light, and a thoughtfully designed layout perfect for both relaxing and entertaining. The kitchen features beautiful granite countertops, handsome cabinetry, and a cozy eat-in space ideal for casual dining. The primary suite is generously sized and includes a custom walk-in closet, dual sink vanity, skylight, and an attractive walk-in shower creating a bright and airy retreat. The guest bedroom also offers a custom closet for added organization and convenience. Additional features include skylights that fill the home with natural light, spacious living areas, and a warm, welcoming atmosphere throughout. Residents of Cypresswood enjoy a gated golf course community with beautifully maintained grounds, scenic surroundings, clubhouse amenities, tennis courts, community pool, restaurant access, and an 18-hole championship golf course, all conveniently located near shopping, dining, medical facilities, and easy access to both Orlando and Tampa. Come experience the peaceful lifestyle and exceptional community setting this lovely townhouse has to offer!
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Erin Floyd (863-412-2286)
103 MORNING GLORY CIR, WINTER HAVEN, FL 33884
$299,99967 Days on yellowkey MLS ID: TB8489377
3 Days Off yellowkey (back on 5/20/2026)
REDUCED by $19,901 (6.2%) on 05/11/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2021 Built: 1996Monthly Fee: $160 Tax: $1,677 (2025)Community: MorningsideSingle Family
Taxes:$1,677
Remarks: Under contract-accepting backup offers. Welcome to 103 Morning Glory Circle in the highly desirable Morningside at Winterset community in Winter Haven. As you step inside, you’ll be greeted by soaring vaulted ceilings, abundant natural light, neutral paint tones and immense charm. The spacious living room is the heart of the home, featuring a cozy fireplace and custom built-in shelving, creating the perfect space to relax or entertain. The home’s layout flows seamlessly, offering both functionality and style, while the tile roof adds durability and long-term value. New HVAC was installed in 2025 and water heater in 2020 along with all new appliances within the last few years. Step outside to your large screened-in patio, ideal for enjoying Florida’s outdoor lifestyle year-round, whether you’re hosting guests or unwinding in your private retreat. Located in a gated community with low HOA and no CDD, homeowners of Morningside at Winterset enjoy access to resort-style amenities including a community pool, clubhouse, tennis courts, private-community boat ramp, and direct lake access to Lake Winterset, perfect for boating, fishing, and soaking up the Florida sunshine. Conveniently situated near LEGOLAND Florida Resort, the Chain of Lakes, shopping, dining, medical facilities, and major highway access, this home offers the perfect blend of peaceful living and everyday convenience. If you’ve been searching for a home that combines character, community, and location, this one checks all the boxes. Schedule your showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Eric Gross (513-907-4271)
5347 MICKEY AVE, WINTER HAVEN, FL 33884
$349,52166 Days on yellowkey MLS ID: S5146851
REDUCED by $478 (0.1%) on 05/20/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2077 Built: 2026Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Remarks: This home offers, 9"4' ceilings and 8' doors, 42' cabinets, white quartz counter tops in kitchen, ceramic tile throughout the wet and main living areas of the home, all bedrooms, family room, and covered lanai are prewired for ceiling fans, secondary bedroom with its own bathroom. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Stephanie Morales, Llc (407-399-2055)
3365 COSTELLO CIR, WINTER HAVEN, FL 33884
$320,00016 Days on yellowkey MLS ID: L4962031
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2522 Built: 2023Monthly Fee: $211 Tax: $7,389 (2025)Community: Villamar Ph 5Spa: NoSingle Family
Taxes:$7,389
Remarks: Short Sale. Discover this beautifully designed 2023-built 5-bedroom, 3-bathroom home located in the highly sought-after Villamar community in Winter Haven, Florida. This spacious two-story home offers the perfect blend of modern style, functional living space, and scenic water views. The welcoming foyer opens into a bright and airy open-concept floor plan ideal for both entertaining and everyday living. The chef-inspired kitchen features plentiful gray cabinetry, a large center island, stainless steel appliances, and an oversized pantry, all overlooking the spacious living room for seamless gathering and conversation. A downstairs bedroom and full bathroom provide the perfect setup for guests, multi-generational living, or a home office. Upstairs, you’ll find a versatile loft space that can be used as a second living area, playroom, media room, or workspace. The spacious primary suite offers a large walk-in closet and private en-suite bathroom complete with double vanities and a walk-in shower. Three additional upstairs bedrooms, another full bathroom, and a convenient upstairs laundry room provide plenty of room for everyone. Step outside and enjoy peaceful water views right from your backyard. Located in the growing Villamar community, residents enjoy amenities including a community pool, clubhouse, playground, and low HOA fees. Conveniently situated near US-27 and I-4, this home provides easy access to shopping, dining, medical facilities, and entertainment. Nearby attractions include the LEGOLAND Florida Resort, the Winter Haven Chain of Lakes, and the Downtown Winter Haven Historic District. This is a fantastic opportunity to own a newer construction home with water views in one of Winter Haven’s fastest-growing communities. Short sale opportunity — don’t miss your chance to make this home yours!
Listing is courtesy of: ENGEL & VOELKERS LAKELAND (863-412-6633)
Listing Agent: Emily Lietz (863-266-9961)
3334 FOX RIDGE DR, WINTER HAVEN, FL 33884
$349,900232 Days on yellowkey MLS ID: P4936715
REDUCED by $12,600 (3.5%) on 05/19/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1542 Built: 1985 Tax: $2,467 (2025)Community: Fox Ridge Ph 01Single Family
Taxes:$2,467
Elementary School: Garden Grove Elem
Remarks: LAKEFRONT LIVING WITH NO HOA Welcome to 3334 Fox Ridge Drive — a beautifully maintained 3-bedroom, 3-bath pool home perfectly situated on over half an acre along the shores of Lake Fox in Winter Haven. Enjoy the peace and privacy of a spacious lot with no HOA, while still being just minutes from shopping, dining, and schools. Step inside to find a bright, open layout designed for both comfort and entertaining. The kitchen overlooks the living area and pool, featuring plenty of cabinetry and counter space. Each bedroom offers generous closet storage and natural light, while the primary suite provides serene lake views and a private ensuite bath. Out back, unwind in your screened pool area or relax under the covered lanai—perfect for outdoor gatherings. The expansive backyard slopes gently toward Lake Fox, offering endless possibilities for fishing, paddleboarding, or simply soaking in the view. Additional highlights include: • Over ½ acre lot • Private lake frontage on Lake Fox • Screened-in pool with lanai • No HOA or CDD fees • Convenient SE Winter Haven location This is a rare opportunity to enjoy lakefront living with freedom and space—schedule your private showing today!
Listing Agent: Brandy Waters (863-268-9585)
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