Location: Winter Haven
Do Not Show Listings
719 AVENUE Q SE, WINTER HAVEN, FL 33880
$220,00015 Days on yellowkey MLS ID: O6409223
3 Days Off yellowkey (back on 6/8/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1181 Built: 1968Monthly Fee: $110 Tax: $487 (2025)Community: Parkland VillageSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$487
Elementary School: None
High School: Winter Haven Senior
Tax Year: 2025
Middle School: Denison Middle
Remarks: Welcome to this well-maintained 2-bedroom, 2-bath home located in a desirable 55+ community in Winter Haven! Situated on a spacious corner lot, this home features engineered hardwood flooring throughout the entire home, creating a warm and cohesive feel. Major updates include a 2025 roof and 2020 water heater, offering peace of mind for the new owner. Enjoy comfortable living with a functional layout, abundant natural light, and low-maintenance living in a quiet established community. Conveniently located near shopping, dining, medical facilities, and local attractions. Don’t miss this opportunity to own a move-in ready home in a great location!
Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)
Listing Agent: Moire Mckibbin (407-361-1139)
3923 BALDWIN LN, WINTER HAVEN, FL 33884
$273,900316 Days on yellowkey MLS ID: P4935847
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1719 Built: 2006Monthly Fee: $467 Tax: $4,082 (2024)Community: Traditions Ph 1Single Family
Taxes:$4,082
High School: None
Tax Year: 2024
Middle School: None
Remarks: WELCOME TO 3923 BALDWIN LANE, NEW ROOF 2023, NEW A/C 2025, FRESHLY PAINTED 2024, RECENT IMPROVEMENTS INCLUDE A NEW GARBAGE DISPOSAL AND THE ADDITION OF A NEW CLOSET IN THE THIRD BEDROOM, ENHANCING BOTH CONVENIENCE AND STORAGE SPACE. LOCATED IN THE HIGHLY SOUGHT-AFTER TRADITIONS GATED COMMUNITY IN WINTER HAVEN! THIS BEAUTIFULLY MAINTAINED HOME OFFERS THE PERFECT BLEND OF COMFORT, STYLE, AND LOW-MAINTENANCE LIVING. FEATURING SPACIOUS LIVING AREAS, A WELL-APPOINTED KITCHEN, AND A SERENE SCREENED-IN LANAI, IT'S IDEAL FOR RELAXING OR ENTERTAINING. ENJOY RESORT-STYLE AMENITIES INCLUDING A CLUBHOUSE, HEATED POOL, FITNESS CENTER, TENNIS COURTS, AND LAKE ACCESS WITH A PRIVATE DOCK-PERFECT FOR ACTIVE ADULTS 55 AND BETTER! WITH 24-HOUR SECURED GATED ENTRANCE AND A VIBRANT, FRIENDLY ATMOSPHERE. TRADITIONS OFFERS THE LIFESTYLE YOU HAVE BEEN LOOKING FOR. THE SELLERS ARE OFFERING A GENEROUS $8,000 CREDIT TO BE APPLIED TOWARD THE BUYER'S PREPAID EXPENSES AND CLOSING COSTS. THIS INCENTIVE PROVIDES ADDED FLEXIBILITY AND CAN HELP REDUCE OUT-OF-POCKET EXPENSES AT CLOSING, MAKING HOMEOWNERSHIP EVEN MORE ATTAINABLE. SCHEDULE YOUR PRIVATE TOUR TODAY AND EXPERIENCE FLORIDA LIVING AT ITS FINEST.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Brian Reeves (877-366-2213)
614 SIDNEY CIR, WINTER HAVEN, FL 33880
$399,99016 Days on yellowkey MLS ID: O6413011
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1908 Built: 1968 Tax: $3,517 (2025)Community: Jan Phyl VillageSingle Family
Taxes:$3,517
Elementary School: Sandhill Elem
High School: Haines City Senior High
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: Discover this beautifully remodeled home located in the desirable Jan Phyl Village community. This property offers the perfect combination of comfort, functionality, and space to enjoy Florida living. The home features 3 bedrooms, 2 bathrooms, a cozy wood-burning fireplace, and a versatile bonus room that can be adapted to fit a variety of needs. The interior provides a warm and inviting atmosphere filled with natural light. Step outside to enjoy a private pool and a fully fenced backyard, ideal for entertaining, relaxing, or enjoying the Florida sunshine. The property includes two lots, offering added privacy and flexibility for future possibilities. Conveniently located near shopping, dining, entertainment, and everyday conveniences. With no HOA restrictions, this property offers greater flexibility for both homeowners and investors. A wonderful opportunity to own a move-in-ready home in a prime Winter Haven location.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Julimar Barreiro Pastrana (407-590-8604)
3006 ELM ST, WINTER HAVEN, FL 33881
$215,00045 Days on yellowkey MLS ID: P4938656
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1172 Built: 1955 Tax: $2,592 (2025)Community: Biltmore ShoresSingle Family
Taxes:$2,592
Elementary School: Auburndale Central Elem
High School: Auburndale High School
Middle School: Westwood Middle
Remarks: Welcome to 3006 Elm Street in beautiful Winter Haven — a charming home full of potential and perfectly positioned for convenience! This 3-bedroom, 1.5-bath home also features a flexible office space that could easily serve as a 4th bedroom, playroom, hobby room, or home gym. Step inside to find new tile flooring, a remodeled bathroom, a newer roof, and updated ceilings that give the home a fresh and modern feel. The spacious kitchen offers plenty of room to cook, gather, and get creative with your dream design ideas. Outside, the backyard is a blank canvas ready for your personal touch — create the garden, outdoor kitchen, pool area, or entertaining space you've always wanted! Conveniently located near shopping, dining, attractions, and with easy access for commuting to both Tampa and Orlando, this property offers the perfect blend of comfort, opportunity, and location. Whether you're looking for your first home, investment property, or extra space to grow, this Winter Haven gem is ready to welcome you home!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Michele Elchin (863-514-6880)
6103 GREY HERON DR, WINTER HAVEN, FL 33881
$295,00051 Days on yellowkey MLS ID: O6403532
REDUCED by $9,999 (3.3%) on 06/12/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1828 Built: 2018Monthly Fee: $15 Tax: $5,214 (2025)Community: Lakeside Landings Ph 01Single Family
Taxes:$5,214
Remarks: Welcome to 6103 Grey Heron Dr in Winter Haven, FL — a beautifully maintained move-in ready home offering modern finishes, open-concept living, and stylish design throughout. This spacious home features a bright and airy split floor plan with neutral tones, abundant natural light, and seamless flow between the kitchen, dining, and living areas — perfect for both everyday living and entertaining. The stunning kitchen is the heart of the home and showcases: • Oversized quartz island with seating • Shaker-style cabinetry • Stainless steel appliances • Modern backsplash details • Ample counter and cabinet space • Open sightlines to the main living area • Designer lighting and upgraded fixtures The primary suite offers a relaxing retreat with spacious accommodations, elegant finishes, and a beautifully appointed ensuite bathroom featuring dual sinks, generous vanity space, and a walk-in glass shower. Additional bedrooms are well-sized and versatile for guests, office space, or family living. Step outside to enjoy the screened lanai overlooking a large backyard with plenty of room to relax, entertain, or create your dream outdoor oasis. Property Features Include: • Newer roof (2025) • Water softener system 2025 • Open-concept layout • Split-bedroom floor plan • Tile flooring in main living areas • Modern light fixtures throughout • Spacious secondary bedrooms • Indoor laundry space • 2-car garage • Screened covered patio/lanai • Large backyard • Contemporary curb appeal Conveniently located near shopping, dining, schools, and major roadways, this home combines comfort, style, and functionality in one beautiful package.
Listing is courtesy of: BROKER HUB REALTY GROUP LLC (219-730-8364)
Listing Agent: Katherine Suero (407-346-4601)
357 RUBY LAKE LOOP, WINTER HAVEN, FL 33884
$415,00092 Days on yellowkey MLS ID: L4960449
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2107 Built: 1998Monthly Fee: $71 Tax: $2,731 (2025)Community: Ruby Lake Ph 01Single Family
Taxes:$2,731
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Remarks: Welcome to your dream home in the gated community of Ruby Lake! This beautifully designed 3-bedroom, 2-bath Cassidy “Ox” floor plan perfectly balances elegance and everyday comfort. Step inside to discover a spacious layout featuring formal living and dining rooms, along with a generous family room—ideal for both entertaining and relaxed living. The updated kitchen is truly the heart of the home, showcasing sleek quartz countertops, a breakfast bar, closet pantry, and durable tile flooring. Retreat to the impressive primary suite, offering a large 17x15 bedroom, walk-in closet, and a spa-like en suite bath complete with soaking tub, walk-in shower, and dual vanities. Thoughtfully designed, the secondary bedroom and bath are handicap accessible with widened doorways for added ease. Enjoy Florida living year-round on the expansive 10x38 screened lanai—perfect for gatherings or quiet evenings. Additional highlights include an interior laundry room with sink, surround sound throughout, plantation shelving with ambient lighting, ceiling fans, irrigation system with separate meter, and a 2-car garage with a high-profile door. Conveniently located near shopping, dining, medical facilities, schools, and Legoland, with easy access to Tampa and Orlando—this exceptional home truly has it all. Don’t miss your opportunity to make it yours!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Steve Lockhart (863-289-9801)
820 AVENUE Z NW, WINTER HAVEN, FL 33881
$197,50023 Days on yellowkey MLS ID: S5150017
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2082 Built: 1925 Tax: $3,824 (2025)Community: Hartridge ManorSingle Family
Taxes:$3,824
Elementary School: Frank E. Brigham Academy
Remarks: Short Sale. Discover a wonderful opportunity in the desirable Winter Haven area. This inviting residence offers comfortable living with a practical and welcoming layout. Bright natural light enhances the interior, creating a warm and airy feel throughout. The living areas flow seamlessly, making everyday living and entertaining effortless. A functional kitchen provides plenty of space for cooking and gathering. Spacious bedrooms showcase relaxing retreats for rest and privacy. The home sits on a generous lot with room to enjoy outdoor living. The backyard is perfect for relaxing evenings, gardening, or weekend gatherings. With no HOA, you’ll enjoy added flexibility and freedom. Ample parking adds convenience for residents and guests alike. The location provides easy access to shopping, dining, and daily essentials. Nearby parks and lakes fit outdoor recreation opportunities year-round. Major roadways are just a short drive away for easy commuting. This property is a great fit for homeowners or investors seeking value and potential. Come explore the possibilities this home has to show for.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Cesar Estrada, Pa (321-209-4782)
5780 LAKESIDE LANDINGS BLVD, WINTER HAVEN, FL 33881
$315,00032 Days on yellowkey MLS ID: P4938750
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2526 Built: 2016Monthly Fee: $15 Tax: $4,656 (2025)Community: Lakeside Landings Ph 01Single Family
Taxes:$4,656
Remarks: From the moment you walk through the door, this home welcomes you with space, comfort, and endless possibilities. Located in the sought-after Lakeside Landings community, this beautifully designed 4-bedroom, 2.5-bath home offers over 2,400 square feet of thoughtfully designed living space. Featuring an open and airy floor plan, generous living areas, and plenty of room to entertain, this home is perfect for growing families or anyone who loves extra space. The large primary suite creates the perfect private escape, while the backyard offers room to relax and enjoy Florida living year-round. Conveniently situated near shopping, dining, and everything Winter Haven has to offer, this home truly checks all the boxes!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Harley Holmes (863-632-6946)
2968 PLANTATION RD, WINTER HAVEN, FL 33884
$442,00092 Days on yellowkey MLS ID: P4938120
0 Days Off yellowkey (back on 5/30/2026)
REDUCED by $23,000 (4.9%) on 04/23/2026
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2433 Built: 1997Monthly Fee: $149 Tax: $3,191 (2025)Community: Cypresswood PlantationsSingle Family
Taxes:$3,191
Remarks: Under contract-accepting backup offers. Enjoy serene golf-front living in this beautifully designed 3BR/2BA home, perfectly positioned to capture golf course frontage and tranquil water views—especially from the private screened patio off the primary suite. A versatile bonus room offers the ideal space for a home office or flex use, and the entire home is wired for surround sound. Thoughtfully equipped for comfort and efficiency, the property features an irrigation well for lush landscaping and a whole-home Generac generator (less than 5 years old) for peace of mind. Inside, a cozy gas fireplace anchors the living area, while the open, spacious floor plan is perfect for both everyday living and entertaining. An expansive screened porch overlooks the golf course and peaceful pastureland, providing exceptional privacy and scenic views. The primary suite is a true retreat, complete with its own screened sitting porch, a spa-like bath with a jetted tub, a walk-in shower, a double vanity, and a bright solarium. The well-appointed kitchen includes a walk-in pantry and built-in shelving, and the oversized laundry room offers a utility sink and abundant cabinetry. Additional highlights include an oversized 3-car garage with extra storage and a paver driveway installed within the last two years. Located in a desirable guard-gated golf course community with amenities including a restaurant, pool, and tennis courts, this home offers a rare opportunity to enjoy relaxed, resort-style living. First time on the market!
Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)
Listing Agent: Joshua Taylor (863-651-5471)
780 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884
$272,50052 Days on yellowkey MLS ID: L4960255
REDUCED by $22,500 (7.6%) on 06/12/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1583 Built: 2013Monthly Fee: $38 Tax: $4,294 (2025)Community: Overlook RdgSingle Family
Taxes:$4,294
Remarks: HOME WARRANTY INCLUDED! Need 4 bedrooms, but don't need to break the budget? This is what you've been searching for here in the heart of Winter Haven! Situated perfectly W of Hwy 27 and out of the hustle and bustle of the city, this 4/2/2 home is ready for you! Close to houses of worship, schools, shopping, golf, and SO much more! Upon arrival, you note the quaint neighborhood, which quickly says "community." The home is situated on a corner lot, as well as on a cul de sac. Upon entry, the new homeowners will be delighted to see easy to maintain flooring throughout the home. No detail was missed in this home's update! New flooring, paint, ceiling fans, kitchen & baths, so she's MOVE-IN READY! The kitchen boasts new countertops, stainless appliances, a cook's workstation, generous sized pantry, and lots of storage. The open floor plan with combined living and dining space is ideal for gatherings and entertaining. The owners suite is spacious, and has a walk in closet and updated bathroom. Three MORE bedrooms, each situated around the living space. This floor plan is superb for daily function of a busy household. Fenced with a durable vinyl fence, the outdoor space is secure for pets. The shed is sturdy for your lawn & garden tools, as well as storage. Equipped with leased solar panels that increase energy efficiency and predictable monthly utility cost. Current solar payment $230/month. (Electric company connection fee applies) Unlike traditional electric bills that fluctuate dramatically during peak simmer and winter months, solar provides consistent energy costs year round. Panels are fully warranted and maintained by the solar company throughout remainder of the lease term for added peace of mind. Water Heater 2021. Roof 2022. Seller is offering a one year American Home Shield warranty!
Listing is courtesy of: FLORIDA REAL ESTATE COMPANY (863-701-3487)
Listing Agent: Cyleste Goodson (863-701-3487)
335 RUBY LAKE LOOP, WINTER HAVEN, FL 33884
$484,90015 Days on yellowkey MLS ID: L4962358
0 Days Off yellowkey (back on 6/12/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2406 Built: 1999Monthly Fee: $71 Tax: $3,154 (2025)Community: Ruby Lake Ph 02Spa: NoSingle Family
Taxes:$3,154
Remarks: Under contract-accepting backup offers. Located in one of SE Winter Haven's most desirable gated communities, this meticulously maintained 4-bedroom, 3-bath pool home offers the perfect blend of elegance, comfort, and Florida outdoor living. Showcasing a desirable triple-split floor plan and numerous updates, including a new roof in 2022 and a new water heater in 2026, this move-in-ready residence is designed to accommodate both everyday living and entertaining with ease. Stepping through the front door, you'll immediately appreciate the soaring ceilings, elegant crown molding, and luxury vinyl flooring that flows seamlessly throughout the entire home. The thoughtfully designed layout offers both formal and casual living spaces, providing a warm and inviting atmosphere. The formal living room features stacking sliding glass doors that open to the lanai and pool, creating seamless indoor-outdoor living, while the adjacent formal dining room provides an elegant setting for gatherings and special occasions. At the heart of the home, the spacious kitchen has been beautifully updated with professionally painted maple wood cabinetry, granite countertops, stainless appliances, a breakfast bar, and a double-door closet pantry offering exceptional storage. The adjoining family room creates a comfortable space to relax and enjoy time with family and friends. The primary suite is a true retreat, featuring pool access, two walk-in closets, and a spacious en-suite bathroom with dual vanities, a soaking tub, and a separate walk-in shower. The home's triple-split layout provides excellent privacy, with two guest bedrooms sharing a full bathroom while the fourth bedroom is tucked away at the rear of the home behind a pocket door alongside the third bathroom, creating an ideal guest suite, in-law space, or home office. The third bathroom also serves as a pool bath. All guest bedrooms are generously sized, and one bedroom features sliding barn doors and a custom-made Lego wall. The interior laundry room adds convenience with built-in cabinetry and a hanging rack. Spend sunny Florida afternoons relaxing in the screen-enclosed swimming pool, lounging on the expansive pool deck, or enjoying shade beneath the covered lanai. The vinyl-fenced backyard offers exceptional privacy with no rear neighbors, creating a peaceful setting for entertaining, pets, or simply enjoying the outdoors. An irrigation well helps keep the landscaping lush while reducing monthly water expenses. Additional features include a generator connection with transfer switch (2024), new toilets (2023), rain gutters, garage work/storage station, extended driveway for additional parking, and more. Residents of Ruby Lake enjoy the security of a gated entrance along with a warm, neighborly atmosphere. Spend peaceful afternoons birdwatching by the scenic community pond, enjoy leisurely bike rides through the neighborhood, or connect with neighbors during an evening stroll along the quiet streets. Conveniently located in Winter Haven with easy access to Legoland FL, downtown restaurants, farmers markets, arts festivals, shopping and a vibrant nightlife scene. Centrally positioned between Tampa and Orlando, this location also provides convenient access to major airports, world-famous attractions, and beautiful Gulf and Atlantic Coast beaches. Combining quality craftsmanship, exceptional privacy, and a desirable location, this beautifully maintained pool home offers an outstanding opportunity to enjoy the very best of Florida living.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Deanna Stone (863-412-2080)
601 LAKE PANSY DR NW, WINTER HAVEN, FL 33881
$765,900157 Days on yellowkey MLS ID: P4937480
REDUCED by $30,000 (3.8%) on 06/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2140 Built: 1977 Tax: $760 (2025)Community: Not In SubdivisionSpa: NoSingle Family
Taxes:$760
Remarks: Lakefront living with a proper sunset! Down a private road with no HOA (because your house shouldn't come with a rule book). This renovated home offers direct frontage 80' on Lake Pansy and a bonus 80' of canal frontage across the street. The property provides excellent water access and endless sunset views. Outside is where this home really shows off with amenities including a heated saltwater pool / lap pool with markers on the bottom, lighting and water features, added style with a surfboard outdoor shower, screened in with panoramic panels because this view deserves center stage. The outdoor summer kitchen is outfitted with a refrigerator, table top ice chest, bar area, and a grill supplied by a 99-gallon propane tank, making it well-suited for entertaining all year round. The lanai is glassed in with cedar tongue and groove ceiling and motorized retractable sunshade, while enhanced landscape lighting and mature palm trees set the tropical tone. Additional exterior upgrades include a composite dock, fenced in yard, seamless gutters with leaf filters, and recently replaced garage and front entry doors. Inside, the vibe continues with an electric fireplace with customizable lighting (because ambiance matters). Live-edge floating shelves with integrated lighting adds a designer touch. Double-pane replacement windows, custom drapes, California Closets, luxury vinyl and ceramic tile throughout, laundry closet for added convenience. The kitchen brings the function and the flair with an island, generous storage, new cabinetry, quartz countertops, a natural gas range with hood ventilation, along with a built in microwave, electric oven, and refrigerator/freezer. Culligan water treatment. The roof and HVAC system are approximately 10 years old. Additional features include epoxy garage floor, LRE foundation improvements, and well-fed irrigation. Prewired generator hook-up installed in garage. The boat ramp is located on the west side of lake Pansy. Conveniently Located 20 minutes from Lego Land, 7 minutes from Publix Super Market, 5 minutes to Home Depot, 3 minutes to the nearest boat ramp to access the Winter Haven Chain of Lakes. This is a rare opportunity to own a turnkey lakefront property with endless sunsets, extensive upgrades, and no HOA restrictions.
Listing Agent: Olivia Boggs (863-232-8234)
1549 DREXEL AVE NE, WINTER HAVEN, FL 33881
$350,0009 Days on yellowkey MLS ID: S5151595
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. Leedy is globally recognized for revolutionizing the use of raw materials and pre-stressed concrete—particularly inventing and utilizing the “Double T” beam to create open, flexible spaces without load-bearing interior walls. 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 eminent beauty and quintessential style. Clean lines, expansive volumes, 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. An expansive backyard and courtyard fully realize his architectural vision. Drexel Avenue remains a celebrated example of Leedy's Florida climate-responsive Mid-Century Modern homes. In 1984, 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, wood-paneled walls, 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, pathways through 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 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. Showings are available for qualified buyers. One or more photos have been virtually staged.
Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)
Listing Agent: Michael Brenner (863-557-3300)
1095 W LAKE HAMILTON DR, WINTER HAVEN, FL 33881
$749,90051 Days on yellowkey MLS ID: L4961524
REDUCED by $27,800 (3.6%) on 06/12/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2363 Built: 1997Monthly Fee: $17 Tax: $6,592 (2025)Community: Hamilton RidgeSingle Family
Taxes:$6,592
Remarks: Welcome to this exceptional 4-bedroom, 3-bath home set on over half an acre, offering a rare combination of space, privacy, and versatility, complete with a heated swimming pool, screened-in patio, and an impressive 32x48 insulated and air-conditioned workshop. From the moment you arrive, you’ll appreciate the curb appeal with a well-maintained exterior, extended driveway, and ample parking leading to the detached workshop — ideal for multiple vehicles, equipment, or recreational toys. Inside, the home offers a bright and functional layout with tasteful finishes throughout. The kitchen is both stylish and practical, featuring warm wood cabinetry, granite countertops, stainless steel appliances, and plenty of counter space — perfect for everyday living and entertaining. The open flow provides easy access to dining and living areas, creating a welcoming environment for family and guests. The primary bathroom is a true retreat, showcasing a spa-like design with a freestanding soaking tub, separate walk-in shower, dual vanities, and modern finishes — offering both comfort and elegance. Step outside and enjoy your private backyard oasis, complete with a heated swimming pool and screened-in patio — ideal for year-round relaxation, bug-free outdoor living, and entertaining. The expansive lot provides plenty of room for additional outdoor activities, storage, or future possibilities. A standout feature is the 32x48 insulated and air-conditioned metal workshop, complete with its own half bathroom, offering endless possibilities for a home business, workshop, vehicle storage, or hobby space. This fully climate-controlled building is a rare find and adds tremendous value and functionality. In addition, the property includes a fully insulated and air-conditioned detached flex space, perfect for a home office, gym, studio, or private retreat — giving you even more versatility to fit your lifestyle. With a rare combination of indoor comfort, outdoor enjoyment, and multiple climate-controlled structures, this property is ideal for those seeking space, functionality, and flexibility.
Listing is courtesy of: PROPERTY SHOPPE OF CENTRAL FL (863-638-6638)
Listing Agent: Damon Trueman (407-276-5417)
12 CHERRY BLOSSOM LN, WINTER HAVEN, FL 33884
$610,00054 Days on yellowkey MLS ID: O6401292
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2100 Built: 1985Monthly Fee: $21 Tax: $2,131 (2025)Community: Sundance Ranch EstatesSingle Family
Taxes:$2,131
Remarks: Welcome to Sundance Ranch Estates! This well-maintained 3-bedroom, 2-bath home sits on 5 acres and offers the ideal balance of country living with convenient access to nearby amenities. The main residence features a spacious living room, formal dining area, and a bright kitchen with breakfast nook. A separate in-law suite includes its own kitchen, bathroom, and private entrance—perfect for multigenerational living or potential rental income. Recent updates include brand new AC (2026), new roof (2024), water heater (2026), and gas stove (2023). Equestrian-friendly, the property is fenced and cross-fenced, providing ample space for horses or other animals. Enjoy privacy, open views, and a versatile layout—all just minutes from shopping, dining, and schools. Move-in ready and designed for flexible living.
Listing is courtesy of: VESTI LLC (407-749-5489)
Listing Agent: Maribel Ramos, Llc (786-281-3336)
3467 JULIUS ESTATES BLVD, WINTER HAVEN, FL 33881
$270,0009 Days on yellowkey MLS ID: S5151796
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1750 Built: 2014Monthly Fee: $105 Tax: $1,247 (2025)Community: Lake Smart EstatesSingle Family
Taxes:$1,247
Remarks: Welcome to this beautiful and well-maintained home in the desirable Julius Estates community of Winter Haven! This spacious residence offers a modern open-concept layout, perfect for both everyday living and entertaining. The kitchen features ample cabinet space, a large island, and overlooks the living and dining areas, creating a bright and inviting atmosphere. The primary suite provides a private retreat with a spacious walk-in closet and an en-suite bathroom. Additional bedrooms offer flexibility for family, guests, or a home office. Enjoy the convenience of a two-car garage, indoor laundry room, and energy-efficient features throughout. Step outside to a generous backyard with plenty of space for outdoor gatherings, pets, or future enhancements. Conveniently located near shopping, dining, schools, medical facilities, and major highways, this home offers the perfect combination of comfort, convenience, and value. Whether you're a first-time homebuyer, growing family, or investor, this is an exceptional opportunity to own a move-in-ready home in one of Winter Haven's growing communities. Schedule your private showing today!
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Ane Bertol Bertol (407-577-5607)
3357 TIMBERLINE RD W, WINTER HAVEN, FL 33880
$279,0009 Days on yellowkey MLS ID: O6416140
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1675 Built: 1983 Tax: $2,765 (2024)Community: Timber WoodSingle Family
Taxes:$2,765
Elementary School: Clarence Boswell Elem
Remarks: Welcome to 3357 Timberline Rd W, located in the charming city of Winter Haven, FL. This exquisite house, a wonderful opportunity to experience comfortable living in a desirable location. The home boasts a timeless design, showcasing a welcoming exterior that hints at the warmth found within. As you step inside, you'll be greeted by well-appointed spaces that cater to both relaxation and entertainment. The layout of this property is thoughtfully designed to provide functionality and style. Experience the convenience of living in a home that meets your needs, whether you're relaxing in your favorite space or hosting gatherings with loved ones. The exterior of the property complements the interior, offering a harmonious balance of indoor and outdoor living. Enjoy all that this beautiful home has to accord in the heart of Winter Haven.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
506 15TH CT NE, WINTER HAVEN, FL 33881
$265,00011 Days on yellowkey MLS ID: L4962442
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1320 Built: 1964 Tax: $2,989 (2025)Community: Hills Lake ElbertSingle Family
Taxes:$2,989
Remarks: Virtually Staged. Welcome to this beautifully renovated, MOVE-IN-READY gem nestled on a spacious nearly quarter-acre lot in the heart of Winter Haven! Perfectly situated on a quiet residential street, this stunning 3-bedroom, 2-bathroom home combines MODERN UPGRADES, functional living spaces, and exceptional outdoor privacy with the freedom of NO HOA RESTRICTIONS. From the moment you arrive, you'll appreciate the inviting curb appeal, long concrete driveway, classic brick accents, and convenient one-car carport. The OVERSIZED HOMESITE provides AMPLE PARKING and plenty of room for additional outdoor storage, recreational vehicles, trailers, or future enhancements. Step inside to discover a bright, open-concept floor plan showcasing gorgeous luxury vinyl flooring, fresh interior finishes, stylish NEW LIGHTING, updated ceiling fans, and an abundance of natural light that creates a warm and welcoming atmosphere throughout the home. The thoughtfully designed layout offers comfortable everyday living while providing the perfect space for entertaining family and friends. At the center of the home is a completely redesigned kitchen that is sure to impress. Featuring elegant quartz countertops, NEW SHAKER CABINETRY, a FARMHOUSE SINK, BRAND-NEW STAINLESS STEEL WHIRLPOOL APPLIANCES, and a breakfast bar, this kitchen delivers the modern finishes maintaining excellent functionality and storage. The thoughtfully designed split bedroom floorplan provides privacy and comfort. The spacious primary suite serves as a relaxing retreat with a beautifully updated ensuite bathroom featuring a stand-up shower, quartz countertops, and a stylish vanity. Two additional bedrooms offer flexibility for guests, family members, a home office, fitness room, or hobby space. The secondary bathroom has also been tastefully renovated with contemporary finishes. Convenience continues with a SEPARATE INDOOR LAUNDRY ROOM offering direct access from both the kitchen and carport, making everyday tasks effortless. French doors open to an EXPANSIVE SCREENED PATIO that serves as an extension of the living space, providing the ideal setting for outdoor dining, weekend gatherings, or simply enjoying Florida's year-round sunshine. Beyond the porch, the FULLY FENCED BACKYARD with PREMIUM VINYL FENCING offers outstanding privacy. Whether you envision a future pool, playground, garden, outdoor kitchen, firepit area, or additional storage building, there's plenty of room to make it your own. Additional updates and features including a roof less than 10 years old, a SEPTIC SYSTEM LESS THAN FIVE YEARS OLD, a BRAND-NEW 2026 WATER HEATER, public water service, and a 2011 HVAC system. The extensive renovations mean less maintenance. Location is everything, and this property delivers. Conveniently located near shopping centers, restaurants, healthcare facilities, schools, parks, and everyday conveniences, you'll also be just MINUTES FROM WINTER HAVEN CHAIN OF LAKES, Downtown Winter Haven, Legoland Florida Resort, Lake Hartridge, and numerous public boat ramps, fishing opportunities, and recreational amenities. Easy access to major highways makes commuting to Lakeland, Orlando, and Tampa a breeze. COMPLETELY RENOVATED, packed with MODERN UPGRADES, situated on a LARGE FENCED LOT, and offering the increasingly rare benefit of NO HOA, this exceptional Winter Haven property presents a unique opportunity seeking a turnkey home in one of Central Florida's most desirable and rapidly growing areas.
Listing Agent: David Small (407-601-8351)
2540 14TH ST SE, WINTER HAVEN, FL 33884
$369,90024 Days on yellowkey MLS ID: O6411362
2 Days Off yellowkey (back on 6/12/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1753 Built: 1956 Tax: $3,789 (2025)Community: South Roy ShoresSingle Family
Taxes:$3,789
Remarks: Turnkey Airbnb opportunity in the heart of Winter Haven! This fully furnished 4-bedroom, 2-bath pool home is perfect for short-term rental income, multi-generational living, or your next investment property. Featuring a flexible multi-generational layout and a suite with its own entrance, the home includes a private in-law suite, creating the ideal setup for guests or extended family. Recent updates include a new roof installed in 2023 for added peace of mind. Inside, you'll find bright and spacious living areas, a functional kitchen with ample cabinet and counter space, and comfortable bedrooms designed for relaxing stays. Outside, enjoy a fully fenced backyard with a private in-ground pool, plenty of room to entertain, and space to unwind. The large driveway and oversized 2-car carport provide ample parking for guests, boats, or multiple vehicles. With no HOA and the property being sold fully furnished, this move-in-ready home offers incredible flexibility as a primary residence, vacation getaway, or income-producing Airbnb. Conveniently located near shopping, dining, schools, and area attractions.
Listing is courtesy of: EXP REALTY LLC (407-706-5000)
Listing Agent: Daniel Betancourt (407-375-9142)
3339 QUEENS COVE LOOP, WINTER HAVEN, FL 33880
$239,900108 Days on yellowkey MLS ID: O6386232
REDUCED by $5,000 (2.0%) on 06/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1158 Built: 1994Monthly Fee: $12 Tax: $3,511 (2025)Community: Queens Cove Ph 02Spa: NoSingle Family
Taxes:$3,511
Elementary School: Eagle Lake Elem
Remarks: This traditional 3-bedroom, 2-bathroom home is located in the established Queens Cove Ph 02 neighborhood. Designed with a functional and classic layout, this residence offers a comfortable living environment perfectly suited for a variety of lifestyles. The heart of the home features a traditional floor plan that provides a clear and smart separation of living spaces. The kitchen is beautifully updated with sleek quartz countertops and Stainless steel appliances, creating a modern and stylish space for meal preparation and entertaining. Situated in a prime location, this home is just minutes away from local essentials, including shopping, dining, and parks. Whether you are searching for a forever home or a smart investment opportunity, this property offers both convenience and potential. Schedule your private showing today!
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
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