Location: Winter Haven
Do Not Show Listings
238 AVENUE F SE, WINTER HAVEN, FL 33880
$204,90025 Days on yellowkey MLS ID: L4962934
3 Days Off yellowkey (back on 7/4/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1187 Built: 1953 Tax: $887 (2025)Community: Havencrest AddSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$887
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. Welcome to this charming 3-bedroom, 2-bath home with a new roof, updated bathroom, and spacious fenced yard with a storage shed. The property could use some finishing touches, making it the perfect opportunity to add your own style and build equity. With ample outdoor space and plenty of potential, don't miss your chance to make this home your own! Just minutes away from Downtown Winter Haven, full of shops and restaurants.
Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)
Listing Agent: Audrey Yopp (863-430-4409)
3588 RALEIGH DR, WINTER HAVEN, FL 33884
$262,500155 Days on yellowkey MLS ID: L4959265
0 Days Off yellowkey (back on 7/4/2026)
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
Taxes:$1,555
Remarks: Under contract-accepting backup offers. 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)
1549 DREXEL AVE NE, WINTER HAVEN, FL 33881
$400,00033 Days on yellowkey MLS ID: S5151595
INCREASED by $50,000 (14.3%) on 07/04/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1120 Built: 1957 Tax: $1,027 (2025)Community: Lake Elbert Heights Unit 01 02 RepSingle Family
Taxes:$1,027
Remarks: This architecturally significant residence offers a rare blend of iconic mid-century design and historical provenance. One of only a few remaining original 1957 Craney Spec homes, the home was designed by celebrated architect Gene Leedy. Regarded as a legend and an icon, Leedy’s importance in history is prominent as a pioneering architect of the Sarasota School of Architecture movement, famous for integrating mid-century modernism with Florida’s climate. This historic residence showcases Leedy’s signature aesthetic, seamlessly merging natural surroundings with interior and exterior living spaces. Meticulously maintained landscaping and fig vines accent the perimeter walls, adding to the property's quintessential style. Clean lines and a seamless connection between interior and exterior spaces define the home’s architectural character. Floor-to-ceiling sliding glass walls, Ocala block, structural beams, and rich mahogany paneling demonstrate Leedy’s mastery of space, proportion, and detail as well as his talent for displaying the beauty of raw materials rather than covering them up. Drexel Avenue remains a celebrated example of Leedy's Florida climate-responsive Mid-Century Modern homes. In 1989, the home was remodeled by Leedy himself. The redesign improved functionality by extending the primary bedroom and primary bathroom walls, adding depth while creating additional storage and a more versatile living space. Other interior highlights include rich tongue-and-groove wood ceilings, a floating gas fireplace, built-in shelving, and wide unobstructed views of the peaceful landscape. The kitchen and both bathrooms have been gutted, providing a blank canvas for a personalized restoration, allowing you to blend historic character with modern convenience. The dining area overlooks the courtyard, creating a stronger connection to the outdoors. The guest bedroom can also serve as an office, with a sliding glass wall that opens to the backyard. Other features include interior and exterior post-and-beam construction, an enclosed garage, original wrought-iron front gate, outdoor shower, tankless water heater, ample storage, track lighting throughout, central air conditioning, lush gardens, a relaxing courtyard for enjoying Florida's cooler days and evenings, and an eight-foot perimeter wall with ambient downlighting throughout. Gene Leedy chose to bring his modernist vision to Winter Haven, a city uniquely shaped by his work. Winter Haven is situated between Orlando and Tampa and surrounded by lakes and year-round pleasant weather. The Lake Elbert Trail is just two blocks away, and downtown is an easy bike ride or enjoyable walk. Polk State College and other everyday conveniences are only minutes from Drexel Avenue. One or more photos have been virtually staged. UPDATE ON PRICE!!!! The home’s remodel (after interior cosmetic demolition) has recently begun, with the goal of preserving the home’s key historic mid-century elements. Key areas of improvement are: New electric wiring throughout the home; all new PEX plumbing to replace original galvanized plumbing; non-tempered sliding glass door glass is being replaced with modern tempered safety glass and new sliding glass door track glides--so the walls of glass slide easily. The original frames from the sliding glass doors will be preserved, thus maintaining the home’s historic integrity. A price adjustment has been made accordingly for these items.
Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)
Listing Agent: Michael Brenner (863-557-3300)
132 LAKE MARIAM WAY, WINTER HAVEN, FL 33884
$320,00011 Days on yellowkey MLS ID: V4949607
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2207 Built: 1995Monthly Fee: $38 Tax: $2,403 (2025)Community: Lake Mariam Hills RepSingle Family
Taxes:$2,403
Remarks: Exceptional value in the gated community of Lake Mariam Hills! This spacious 4 bedroom home presents a rare opportunity to purchase in one of Winter Haven's most desirable neighborhoods at a price that reflects the opportunity for updating. Offering a functional floor plan, generous room sizes, and solid construction, this property is ready for a new owner to add their personal style. Residents here enjoy beautiful surroundings, mature landscaping, and a peaceful residential setting. The home's location provides convenient access to Downtown Winter Haven, the famous Chain of Lakes, numerous parks, golf courses, walking trails, and outdoor recreation opportunities. Enjoy weekends boating, fishing, or exploring nearby attractions including LEGOLAND® Florida Resort and Lake Howard Nature Park. Everyday conveniences are just minutes away, including shopping, dining, healthcare facilities, and Winter Haven Hospital. The property is also conveniently located near public and private schools, making it an attractive option for a variety of buyers. Easy access to Cypress Gardens Boulevard, US-17, the Polk Parkway, and I-4 allows for convenient travel to Lakeland, Orlando, and Tampa. Don't miss the chance to make this property your own and enjoy all that this sought-after community has to offer.
Listing is courtesy of: WATSON REALTY CORP (386-734-4559)
Listing Agent: Jourdan Hoover (407-401-1182)
2362 BRASSIE CT, WINTER HAVEN, FL 33884
$273,900144 Days on yellowkey MLS ID: O6384404
REDUCED by $1,000 (0.4%) on 06/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1260 Built: 2022Monthly Fee: $18 Tax: $5,003 (2025)Community: VillmarSpa: NoSingle Family
Taxes:$5,003
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Middle School: Denison Middle
Remarks: One or more photo(s) has been virtually staged. Opportunity for an assumable mortgage at a 4.5% interest rate, subject to lender approval and buyer qualification! Nestled in the growing Villamar community, this beautifully maintained 3-bedroom, 2-bath Meritage Home offers modern comfort and an ideal location near Chain of Lakes Elementary. Built with energy efficiency in mind, this newer home features an inviting open-concept floor plan where the kitchen flows seamlessly into the spacious great room—perfect for entertaining and everyday living. The kitchen showcases quartz countertops, stainless steel appliances, a pantry, and ample cabinetry for storage. Sliding glass doors off the family living area leads to the backyard, offering easy indoor-outdoor living. The thoughtfully designed split-bedroom floor plan provides privacy, with two secondary bedrooms and a guest bath located at the front of the home, while the primary suite is tucked away off the great room. The spacious owner’s retreat includes quartz countertops, dual sinks, a walk-in tile shower, and a generous walk-in closet. Ceramic tile flooring enhances the main living areas with a clean, modern aesthetic, while the bedrooms provides comfortable carpeting. Residents of Villamar enjoy resort-style amenities, including a community pool with lap lane overlooking Crystal Lake, playground, and convenient community mailboxes. The location offers quick access to Route 27 for commuting to Orlando and is just minutes from Legoland, shopping centers, Publix, and Walmart. This community is only two miles from Legoland and in close proximity to Posner Park which offers many stores, restaurants and entertainment for your family, as well as the Orlando's theme parks. Discover the perfect blend of comfort, convenience, and community in this move-in ready home. The photographs included in this listing were taken during a previous rental listing. The property may appear slightly different at time of showing. One or more photos have been modified or virtually staged for illustrative purposes.
Listing is courtesy of: RE/MAX INNOVATION (407-281-1053)
Listing Agent: Millie Brockmeyer (407-970-9782)
247 S LAKE PANSY DR, WINTER HAVEN, FL 33881
$469,90092 Days on yellowkey MLS ID: TB8496517
REDUCED by $10,000 (2.1%) on 05/10/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2847 Built: 1986Monthly Fee: $136 Tax: $2,948 (2025)Community: Hartridge HillsSingle Family
Taxes:$2,948
Remarks: LAKEFRONT 3 BEDROOM / 2 BATH HOME ~ 2,847 SQ FT ~ WITH PICTURESQUE OPEN WATER VIEWS AND PRIVATE 30 FT DOCK! OWNER FINANCING AVAILABLE. Located directly on Lake Pansy in the gated subdivision of Hartridge Hills, a quaint lakefront community of approximately 60 homes. NEWER ROOF 2022 and NEWER GENERAC GENERATOR 2020. Lot size is 150 X 83 ft directly on Lake Pansy. Additional lot size in records of 2.44 acres includes riparian or water rights into the lake. Beautiful stone working fireplace with vaulted ceiling in the great room. Spacious kitchen with plenty of storage and breakfast area overlooking tranquil water views. With 2,847 sq ft of air-conditioned living space under roof, you have plenty or room for entertaining and extended family. Large windows and sliding glass doors frame panoramic vistas, infusing the space with a sense of tranquility and connection to nature. Attached 2-car garage with large storage room with AC. HOA fees include lawn care, trimming and fertilizer to give you more time to relax. Access to Lake Hartridge and the ‘Chain of Lakes’, a navigable canal system connecting 15 lakes, is obtained from the private community boat ramp and dock. This community is well known and desired by aircraft owners and flying enthusiasts as it is near Gilbert Field-Winter Haven Regional Airport, a city-owned airport that supports over 80,000 flights a year. It is also home to the Jack Brown Seaplane Base renowned as the largest and one of the oldest seaplane training and base operations in the world. Conveniently located between Orlando and Tampa with great attractions, waterfront restaurants, shopping, and some of the best fishing and ski lakes available! Welcome home to endless days of sunshine and relaxation. Please see the interactive 3D virtual tour and floor plan. Virtually staged photos are included.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Kay Szinegh (813-918-0624)
3408 COSTELLO CIR, WINTER HAVEN, FL 33884
$315,00046 Days on yellowkey MLS ID: O6411460
INCREASED by $10,000 (3.3%) on 06/01/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1713 Built: 2025Monthly Fee: $18 Tax: $3,036 (2025)Community: Villamar Ph 6 & Ph 6DSpa: NoSingle Family
Taxes:$3,036
Remarks: 4-bedroom, 2-bathroom home, you'll find 1,713 square fee of comfortable living. A Craftsman-style front porch welcomes you into the fully open living area featuring airy volume ceilings and sunny natural lighting. Unwind in your private owner's suite complete with a large walk-in wardrobe and a private en-suite bath with dual vanities, a tiled glass-enclosed shower, private toilet, and a linen closet. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz 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 quartz 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 are flexible 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. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. Priced to Sell !!
Listing is courtesy of: BEACH REALTORS (407-201-6300)
Listing Agent: Rachel Reyes (407-201-6300)
1715 SANDALWOOD CIR SW, WINTER HAVEN, FL 33880
$283,99984 Days on yellowkey MLS ID: P4938520
2 Days Off yellowkey (back on 7/4/2026)
REDUCED by $14,901 (5.0%) on 05/10/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1556 Built: 1990 Tax: $3,176 (2025)Community: Sandalwood SubSpa: NoSingle Family
Taxes:$3,176
Remarks: Under contract-accepting backup offers. This updated and well-maintained three-bedroom, two-bath home, built in 1990, offers timeless comfort with smart updates. It features a new roof installed four to five years ago, double-paned tinted windows, city water and sewer, plus a dedicated well for the sprinkler system. Inside, you'll find an electric fireplace, updated kitchen with range, refrigerator, dishwasher, washer and dryer. flooring is a mix of tile, laminate, and carpet, a full security system, Ring doorbell, camera system, and a water purifier. The two-car garage comes with an opener, and the fully fenced backyard includes both chain-link and wood sections, a storage shed, and a handy workshop - plus the lawnmower stays with the property. It's a turnkey, low-maintenance gem ready for its next chapter.
Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)
Listing Agent: Teresa Markley (863-207-3457)
4253 STAFFORD DR, WINTER HAVEN, FL 33880
$374,80028 Days on yellowkey MLS ID: A4697252
REDUCED by $5,000 (1.3%) on 07/04/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2631 Built: 1985 Tax: $2,553 (2025)Community: Lake Thomas Woods Add 02Single Family
Taxes:$2,553
Remarks: Nestled on a spacious 0.5-acre lot with an in-ground pool, this solid Winter Haven home balances completed improvements with an opportunity to add your own personal updates. A stunning converted family room boasts a natural wood interior, full wet bar, and an open layout, while a separate detached 2-car garage provides ample parking. Enjoy a cozy living area with a brick fireplace and built-in bookshelf. The large master suite features a walk-in closet and a jacuzzi tub. With extensive storage, a large cabinet-packed kitchen, and an optional HOA, this home is ready for your vision!
Listing is courtesy of: JOSEPH WALTER REALTY LLC (248-294-7850)
Listing Agent: Scott Fader (248-294-7850)
5148 MAGNOLIA PRESERVE BLVD, WINTER HAVEN, FL 33880
$318,00016 Days on yellowkey MLS ID: O6419703
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1654 Built: 2018Monthly Fee: $35 Tax: $3,724 (2025)Community: Magnolia Preserve Ph 1Single Family
Taxes:$3,724
Remarks: Welcome to 5148 Magnolia Preserve Blvd, Winter Haven, FL 33880! This beautifully maintained 4-bedroom, 2-bathroom home offers the perfect combination of comfort, space, and convenience. Designed with an inviting open-concept floor plan, this residence provides ample room for both everyday living and entertaining. The spacious living and dining areas flow seamlessly into the heart of the home, creating a bright and welcoming atmosphere. All bedrooms feature comfortable carpeting, providing warmth and comfort throughout the private living spaces. Curb appeal shines with attractive front landscaping that enhances the home's charm from the moment you arrive. Step outside to discover a large, fully fenced backyard—ideal for pets, family gatherings, and outdoor activities. The generous seating area creates the perfect setting for relaxing evenings, weekend barbecues, and entertaining guests. Conveniently located near major attractions, this home offers easy access to LEGOLAND Florida Resort, shopping, dining, and recreation. With its spacious layout, beautiful outdoor space, and desirable location, this property presents an excellent opportunity to enjoy the best of Central Florida living. Schedule your private showing today and experience everything this wonderful home has!
Listing is courtesy of: LA ROSA REALTY CENTRAL FLORIDA LLC (407-861-8009)
Listing Agent: Teneke Outing (863-605-8802)
116 MANDOLIN DR, WINTER HAVEN, FL 33884
$349,90076 Days on yellowkey MLS ID: O6403313
REDUCED by $15,100 (4.1%) on 06/26/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2248 Built: 2009Monthly Fee: $56 Tax: $5,678 (2025)Community: MandolinSingle Family
Taxes:$5,678
Remarks: ARE YOU LOOKING FOR A GATED COMMUNITY WITH A LOW HOA and NO CDD? At 116 Mandolin Dr in WINTER HAVEN, FL! This spacious 4-bedroom, 2-bathroom home offers 2,248 square feet of COMFORTABLE LIVING on a generous 0.26-acre lot! Step inside to soaring VAULTED CEILINGS in the living and dining areas—these ELEVATED CEILINGS create an open, airy feel that makes the home even larger than its footprint. The entire home features durable VINYL FLOORING, and all bedrooms are generously sized, offering FLEXIBILITY FOR FAMILIES, guests, or a home office. NATURAL LIGHT pours in throughout the home, creating a bright and welcoming atmosphere that’s perfect for new homeowners. Major updates include a NEW A/C SYSTEM (2025) and GUTTERS INSTALLED (2024), while the WATER HEATER was replaced in 2017. The roof and plumbing are original, but the seller is willing to NEGOTIATE A BRAND NEW ROOF — making this property an UNBEATABLE VALUE for the price. Situated in a quiet gated community, this property offers both privacy and security. The location is a standout—just a short walk from a newly constructed Publix set to open in the coming months, as well as nearby Dollar General and 7-Eleven for everyday convenience. You’re also just minutes away by car from Eagle Ridge Mall, LEGOLAND Florida Resort, and all the shopping, dining, and entertainment that downtown Winter Haven has! —making this home not only comfortable, but perfectly located.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Nomar Rosa (646-673-3900)
1558 DREXEL AVE NE, WINTER HAVEN, FL 33881
$349,50091 Days on yellowkey MLS ID: L4960971
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: Virtually Staged. HUGE PRICE DROP! Completely renovated Gene Leedy home 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)
3723 IMPERIAL DR, WINTER HAVEN, FL 33880
$250,000188 Days on yellowkey MLS ID: O6371966
REDUCED by $5,900 (2.3%) on 07/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1264 Built: 1999Monthly Fee: $8 Tax: $2,835 (2025)Community: Queens CoveSingle Family
Taxes:$2,835
Remarks: Stop looking now!This well kept home is waiting just for you. A nice 3/2 with tile and laminate thorough. This home offers a beautiful back yard with a deck for a peaceful retreat for enjoyment of the lake.Price just reduced for quik sale. Schedule your showing now.
Listing is courtesy of: PROPERTY WAREHOUSES OF AMERICA (321-234-2683)
Listing Agent: Louis Vincent (321-436-9220)
440 PALMA CEIA RD, WINTER HAVEN, FL 33884
$775,00034 Days on yellowkey MLS ID: O6415193
REDUCED by $25,000 (3.1%) on 07/03/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2575 Built: 2023Monthly Fee: $149 Tax: $6,403 (2025)Community: Cypresswood Golf/CcSpa: NoSingle Family
Taxes:$6,403
Elementary School: Elbert Elem
High School: Winter Haven Senior
Remarks: Over 1 Acre with Golf Course Views in Cypresswood Golf & Country Club. Discover a rare opportunity to own one of the LARGEST residential lots in Cypresswood Golf & Country Club, one of Winter Haven's premier gated golf communities. Built in 2023 and situated on 1.17 acres, this exceptional 4-bedroom, 3-bathroom residence offers luxury, privacy, and modern living with expansive views of the 2nd green and 9th tee of the Ron Garl-designed championship golf course. A long private driveway lined with Florida-friendly landscaping leads to an expansive paver parking courtyard and oversized three-car garage featuring a professionally finished epoxy floor. Ebony-finished tongue-and-groove ceilings on both the front entry and rear screened lanai create an impressive first impression, while the Therma-Tru insulated front door with decorative glass insert welcomes you inside. The thoughtfully designed OPEN-CONCEPT FLOOR PLAN features luxury vinyl plank flooring throughout, soaring ceilings with decorative beam details, custom millwork, recessed lighting, and large windows that fill the home with natural light. The spacious great room is anchored by a custom shiplap feature wall with an electric fireplace and opens seamlessly to the covered lanai through oversized sliding glass doors. A premium Denon surround sound system serves both the great room and lanai, making entertaining effortless. The gourmet kitchen combines style and functionality with quartz countertops, a large center island, solid wood cabinetry, under-cabinet lighting, a walk-in pantry with custom shelving, Frigidaire Professional Series stainless steel appliances, and a natural gas cooktop. The spacious primary suite offers a tray ceiling with decorative beams, an oversized walk-in closet, and a luxurious ensuite bath featuring dual vanities, a garden tub, walk-in shower, and private water closet. The split-bedroom floor plan provides privacy for family and guests, and every bedroom includes a walk-in closet. Step outside and enjoy the freedom of owning more than an acre with panoramic golf course views and plenty of room to create your dream outdoor living space. Residents of Cypresswood Golf & Country Club enjoy an 18-hole championship golf course, clubhouse, restaurant, junior Olympic-sized pool, tennis and pickleball courts, and scenic roads perfect for walking, running, and biking. Conveniently located near US-27, I-4, the Polk Parkway, downtown Winter Haven, and LEGOLAND Florida Resort, this home offers an exceptional combination of luxury, space, and location.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Jessica Estrada (863-409-1771)
250 VOLUSIA DR, WINTER HAVEN, FL 33884
$279,000162 Days on yellowkey MLS ID: L4958940
REDUCED by $15,000 (5.1%) on 07/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1449 Built: 1974 Tax: $2,344 (2025)Community: Eloise Woods Lake Mariam UnitSingle Family
Taxes:$2,344
Remarks: HUGE PRICE DROP! Welcome to this charming 3-bedroom, 2-bathroom home in Winter Haven, offering an open and functional layout perfect for everyday living and entertaining. This solid single-family residence features approximately 1,449 sq. ft. of comfortable living space, including a cozy living/dining combination and a well-appointed kitchen. The property boasts significant recent upgrades, including: - Roof: Installed in 2021 - HVAC: Brand new A/C system, ducts, and air handler installed one year ago - Water Heater: Only 3 months old - Flooring: Brand new tile throughout the entire home Outside, you will find a large fenced backyard providing ample room for gardening, play, or weekend grilling. Ideally located on a quiet residential street, this home is just minutes from shopping, dining, major highways, local attractions, and Legoland. With no HOA, this home is an excellent opportunity for first-time buyers, those looking to downsize, or investors seeking value and convenience. Don’t miss out on this Winter Haven gem!
4599 REYNOSA DR SW, WINTER HAVEN, FL 33880
$309,999183 Days on yellowkey MLS ID: S5141435
REDUCED by $15,001 (4.6%) on 06/29/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2309 Built: 1984 Tax: $3,589 (2025)Community: Plaza SubSingle Family
Taxes:$3,589
Elementary School: Lake Shipp Elem
Middle School: Westwood Middle
Remarks: Some homes are built. Others are crafted. Tucked away in a quiet Winter Haven neighborhood, 4599 Reynosa Drive is a rare, cedar-constructed residence that blends artisan craftsmanship with modern efficiency. From the moment you arrive, the home sets itself apart fully fenced with new vinyl fencing, enhanced exterior lighting, and a brand-new Trex front porch designed for relaxed mornings and long evenings. Inside, the warmth is immediate. Cedar wood wraps the interior, creating a natural, timeless atmosphere rarely found in Florida homes. The craftsmanship was completed by a skilled wood artisan, and the attention to detail is felt throughout custom wood features, soaring character, and a layout that feels both grounded and inviting. Tile flooring spans the entire downstairs, while all bathrooms are finished floor-to-ceiling in tile, offering durability and a clean, elevated aesthetic. The home has been thoughtfully upgraded for comfort and longevity, including brand-new hurricane-impact, double-pane windows with architectural tint reflecting up to 90% of heat, a new AC unit, new attic fan, insect-repellent insulation, and a fully sealed roof coated with heat-reflective, hurricane-rated paint. Even in peak summer, electric bills remain impressively low under $150 with no solar required. The kitchen and bathrooms feature newer plumbing, modern appliances (all just a few years old), and a standout stone-wrapped Jacuzzi tub, creating a spa-like retreat within the home. Side sliders bring in natural light and connect indoor living with outdoor space, while the garage includes sensor lighting, Hardie backer walls, full electrical, and AC, making it ideal for a workshop, studio, or flex space. The property is being offered fully furnished, including custom handcrafted wood furnishings (excluding beds and sofas), making it a true turnkey opportunity for a buyer who values character, quality, and immediate livability. Regular termite and pest control servicing adds peace of mind to this cedar-built, naturally insect-resistant home. Centrally located between Orlando and Tampa, with convenient access to major highways, shopping, and daily essentials, this home delivers both lifestyle and location. This is not a cookie-cutter property. This is a home with a story built to last, designed to feel different, and ready for its next chapter.
Listing Agent: Jason Prieto (877-366-2213)
3642 QUEENS COVE BLVD, WINTER HAVEN, FL 33880
$234,90064 Days on yellowkey MLS ID: O6406940
REDUCED by $8,600 (3.5%) on 07/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1396 Built: 2005Monthly Fee: $12 Tax: $3,427 (2025)Community: Queens Cove Ph 04Single Family
Taxes:$3,427
Remarks: Welcome to this spacious 3-bedroom, 2-bathroom home located in the desirable Winter Haven area. This residence offers a great floor plan with plenty of natural light, a kitchen with ample storage, and a layout ideal for both everyday living and entertaining. The owner’s suite features a private bath and walk-in closet, while the three additional bedrooms provide flexibility for family, guests, or a home office. The property is conveniently situated near major Central Florida attractions, including LEGOLAND Florida Resort, and is just a short drive from Walt Disney World and Universal Orlando Resort. Residents will also enjoy proximity to shopping at Posner Park Village, diverse dining options, and excellent medical facilities such as BayCare Winter Haven Hospital. For outdoor enthusiasts, nearby Lake Eloise, Chain of Lakes Park, and Bok Tower Gardens brings ample recreation and leisure opportunities. With its prime location and easy access to highways connecting Orlando and Tampa, this property offers the perfect combination of comfort and convenience. Don’t miss the opportunity to make this beautiful Winter Haven home yours. Roof (2017) Water heater (2025)
Listing is courtesy of: OAK AVENUE REAL ESTATE LLC (407-720-5000)
Listing Agent: Vivian Ortiz (863-514-7641)
3212 ROYAL TERN DR, WINTER HAVEN, FL 33881
$238,50042 Days on yellowkey MLS ID: S5151131
2 Days Off yellowkey (back on 7/3/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1725 Built: 2020Monthly Fee: $12 Tax: $5,952 (2025)Community: Lakeside Lndgs Ph 3Single Family
Taxes:$5,952
Elementary School: Fred G. Garnier Elem
Remarks: Welcome home to this newer 3-bedroom, 2-bath residence built in 2020, offering 1,672 square feet of thoughtfully designed living space. The open-concept layout creates a bright and inviting atmosphere, with the living, dining, and kitchen areas flowing together to accommodate both everyday living and entertaining. The primary suite features a walk-in closet, while the primary bathroom is equipped with dual sinks and a walk-in shower for added convenience. With a functional floor plan and modern design, this home provides the ideal blend of comfort and practicality. The home is ready to be converted into your ideal living space. Don't miss your opportunity to make this home yours—schedule your private showing today! The home is being sold in as is condition. All buyers must view the home before submitting an offer.
Listing is courtesy of: REALTYCITY INC (863-438-6605)
Listing Agent: Jesse Carriedo (863-438-6605)
106 LANTERN LN, WINTER HAVEN, FL 33884
$212,000180 Days on yellowkey MLS ID: O6374164
1 Days Off yellowkey (back on 7/3/2026)
REDUCED by $3,000 (1.4%) on 06/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1134 Built: 1973 Tax: $2,698 (2025)Community: UnincorporatedSingle Family
Taxes:$2,698
Remarks: Under contract-accepting backup offers. Back on the market due to buyer financing, property previously appraised at $215,000. Welcome to 106 Lantern Ln in Winter Haven, a comfortable and move in ready 2 bedroom 2 bathroom home with 1,134 square feet of living space. When you step inside, you are welcomed into the living room that opens nicely to the dining area and adjoining kitchen, creating a functional and inviting layout for everyday living. From the dining room, you can step into the Florida room, a great space to relax, enjoy your morning coffee, or use as a flexible bonus area. One of the bathrooms has been recently updated and features a new tiled shower. The home has seen several major updates, including a new HVAC system installed in December 2025, along with a new roof and water heater replaced in 2023, and recently septic pumped this year. Out back, a storage shed provides plenty of room for tools, equipment, or extra storage. From the front yard, you can enjoy peaceful views of Ruby Lake, adding to the home’s charm. Conveniently located just minutes from Legoland Florida, Walmart, Winter Haven Medical Plaza, as well as shopping, dining, and everyday conveniences, this home is ready for its next owner. Schedule your showing today.
Listing is courtesy of: JADE KEY REALTY LLC (407-743-7766)
Listing Agent: Quoc Huynh (407-575-1355)
5716 LAKESIDE LANDINGS BLVD, WINTER HAVEN, FL 33881
$249,00063 Days on yellowkey MLS ID: S5149694
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1748 Built: 2018Monthly Fee: $12 Tax: $4,334 (2025)Community: Lakeside Landings Ph 01Single Family
Taxes:$4,334
Remarks: Welcome to this newer 1 Story home! This 4-bedroom, 2-bath home offers 1,748 square feet of comfortable living space with an open-concept layout designed for both everyday living and entertaining. Enjoy a spacious kitchen overlooking the main living and dining areas, generously sized bedrooms, and a private primary suite with ample closet space and an en-suite bath. Natural light flows throughout the home, creating a warm and inviting atmosphere, while the outdoor space provides room to relax or entertain. Conveniently located near shopping, dining, schools, and major roadways, this home offers both comfort and convenience in a desirable community. This home is ready to be converted into your ideal living space. Don’t miss the opportunity to make this beautiful property your next home—schedule your private showing today! 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. The buyer must deliver an updated copy of the preapproval letter or Proof of Funds dated within 30 days. The escrow deposit must be in form of Certified Funds and the check must be delivered to the Listing Broker within 48 hours of bid acceptance by HUD. The escrow check must be payable to the Buyer's closing Title Agent listed on the initial bid. Do Not make the escrow check payable to the Listing Broker and Do not wire nor deliver the escrow check to the title company. Failure to deliver the escrow check and pre-approval letter within 48 hours will result in bid cancellation by HUD and no extensions will be granted. HUD CASE: 093-914062 FINANCE ESCROW MAY APPLY FINANCE CODE: IE
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