Location: Winter Haven , 33881
Do Not Show Listings
3421 HICKORY ST NW, WINTER HAVEN, FL 33881
$187,00016 Days on yellowkey MLS ID: O6412571
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 690 Built: 1955 Tax: $962 (2025)Community: Biltmore ShoresSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$962
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: NO HOA! This 2 bedroom, 1 bathroom property has an eat-in kitchen with granite countertops & dining space, and a separate living room for gathering. There is luxury vinyl plank (LVP) floors throughout the home and the bathroom has been newly tiled. The home has UV double-insulated windows, 8x10 shed with finished interior, electricity & wall A/C unit, and a spacious fenced backyard with vehicle gate. Seller updates include screen-enclosed front entry, landscape & sod, bathroom tile, crown molding, living room ceiling fan, LVP & baseboards, and finished shed. This home sweet home is tucked away approximately a half mile to Havendale Blvd which leads to groceries, restaurants and connecting highways/roads for commutes. A brand new Publix will soon be opening right next to this neighborhood! Bring your watercraft because you're approximately one mile to a public boat ramp for Lake Jessie which is known for its fishing, aviation activity (including seaplanes!), and is part of Winter Haven's famous Chain of Lakes.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Juan Castro (407-808-5353)
961 DREXEL AVE NE, WINTER HAVEN, FL 33881
$305,000114 Days on yellowkey MLS ID: L4959592
REDUCED by $10,000 (3.2%) on 06/08/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1856 Built: 1948 Tax: $3,409 (2025)Community: Anna MarSingle Family
Taxes:$3,409
Elementary School: Inwood Elem
High School: Winter Haven Senior
Middle School: Westwood Middle
Remarks: ***PRICE DECREASE*** This unique 2-story home in Winter Haven is full of character and charm, located just three houses down from scenic Lake Elbert. Thoughtfully updated while preserving its warm, rustic appeal, this property offers a welcoming atmosphere from the moment you arrive. Outdoor enthusiasts will love the 2.4-mile paved loop trail surrounding Lake Elbert, complete with boardwalks and beautiful landscaping—perfect for morning walks, bike rides, or peaceful evening strolls. The home is in walking distance to Downtown Winter Haven, the public boat ramp and park, and Polk State College’s Winter Haven Fine Arts Building, offering exceptional convenience and lifestyle amenities. Inside, you’ll find live-edge wood countertops, natural wood trim, and an open kitchen overlooking the family and dining rooms. The kitchen features stainless steel appliances, newer cabinets, and a rustic flair originally crafted by an Amish family. The spacious family room includes a large picture windows that frame the beautiful front yard and mature oak tree. The primary bedroom and bathroom are conveniently located downstairs, while the second floor offers two additional bedrooms, a bonus room, a full bathroom, and a loft area with generous storage closets. Both bathrooms have been updated with newer cabinets, newer countertops, and newer tile. Additional interior upgrades include newer luxury vinyl plank flooring, newer windows, newer light fixtures and ceiling fans, and fresh interior paint. The home also features a newer A/C system. Outside, the home offers a covered front porch perfect for evening relaxation, mature landscaping, and a fenced yard on nearly a quarter-acre, with most of the outdoor space located in the front of the home. Ideally situated near Lake Elbert, Downtown Winter Haven, Polk State College, shopping, dining, parks, and medical facilities, this home offers both convenience and character. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Lisa Ford (863-510-3890)
1055 30TH ST NW, WINTER HAVEN, FL 33881
$199,90035 Days on yellowkey MLS ID: TB8507249
REDUCED by $10,000 (4.8%) on 06/13/2026
Bed: 4 Bath: 1.0 Liv Area Sq Ft: 1020 Built: 1955 Tax: $1,715 (2025)Community: Rosewood ManorSingle Family
Taxes:$1,715
Remarks: **Price Improvement** Move-in ready and fully remodeled from top to bottom, this 4-bedroom, 1-bathroom home at 1055 30th Street NW in Winter Haven is a true turnkey opportunity. Brand new roof (2026), brand new AC (2026), brand new windows (2026), new plumbing, and a new water heater mean all the big-ticket items are already handled — just bring your furniture and move right in. Inside, you'll find all new vinyl flooring throughout, a beautifully updated kitchen, and a flexible bonus room that can easily serve as a 4th bedroom, home office, playroom, or guest bedroom — whatever fits your lifestyle. Tucked into a quiet Winter Haven neighborhood with quick access to Highway 17, US-27, and Legoland, you're minutes from shopping, dining, and some of Polk County's best lakes.
Listing is courtesy of: YELLOWFIN REALTY (813-347-7547)
Listing Agent: Philips Joseph (813-955-1966)
2235 LAKERIDGE DR, WINTER HAVEN, FL 33881
$300,00068 Days on yellowkey MLS ID: P4938412
REDUCED by $5,000 (1.6%) on 06/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1893 Built: 2015Monthly Fee: $65 Tax: $2,614 (2025)Community: Lakeridge EstatesSingle Family
Taxes:$2,614
Elementary School: Frank E. Brigham Academy
Remarks: Welcome to 2235 Lakeridge Estates, your opportunity to enjoy the Florida lifestyle in one of Winter Haven's growing and desirable communities near scenic Lake Hartridge and the Beautiful Winter Haven Chain of Lakes. An exceptional opportunity to own a beautifully designed home in the heart of Winter Haven. Nestled within the desirable Lakeridge Estates community near scenic Lake Hartridge, this well-maintained 3-bedroom, 2-bathroom residence offers nearly 1,893 square feet of thoughtfully designed living space, blending comfort, functionality, and Florida lifestyle appeal. From the moment you arrive, you’re greeted by a welcoming entry that opens into a bright, open-concept floor plan featuring vaulted ceilings and a seamless flow between the living and dining areas—perfect for both everyday living and entertaining. The spacious kitchen is a standout, complete with stainless steel appliances, ample cabinetry, a center island, and a pantry, making it as practical as it is stylish. The split-bedroom layout offers privacy and comfort, with a generously sized primary suite featuring a walk-in closet and an en-suite bath with dual features designed for relaxation. Two additional bedrooms provide flexibility for guests, family, or a home office. Step outside to one of this home’s most desirable features—a spacious backyard, ideal for outdoor gatherings, pets, or creating your own private oasis. The covered rear porch extends your living space outdoors, capturing the essence of Florida indoor-outdoor living. Location is key, and this home delivers. You’re just minutes from everyday conveniences including shopping destinations, along with casual dining options. Beyond daily conveniences, Winter Haven is known for its vibrant charm and attractions. Enjoy weekends exploring the nearby Chain of Lakes, or take a short drive to world-renowned destinations like LEGOLAND Florida Resort, a major area highlight for entertainment and recreation. The revitalized downtown district offers local boutiques, dining, and community events, adding to the area’s growing appeal. Whether you’re a first-time buyer, growing household, or investor, 2235 Lakeridge Drive presents a compelling blend of space, location, and lifestyle—an inviting place to call home in one of Central Florida’s most steadily growing markets.
Listing is courtesy of: LA ROSA REALTY CENTRAL FLORIDA LLC (407-861-8009)
Listing Agent: Maria Elena Fernandez (407-704-0732)
3426 HICKORY ST NW, WINTER HAVEN, FL 33881
$220,00068 Days on yellowkey MLS ID: O6398170
REDUCED by $10,000 (4.3%) on 05/12/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1044 Built: 1955 Tax: $2,004 (2025)Community: Biltmore ShoresSingle Family
Taxes:$2,004
Remarks: Virtually Staged. NO HOA! LOW TAXES! ASSUMABLE FHA LOAN! NEW FLOORS! NEW FENCE! Bring your boat, your work vehicle and your RV! This home is has plenty of yard to hold all your toys and you won't be bothered by an HOA! This move-in ready property features brand new flooring and fresh interior paint, offering a clean, modern feel throughout. This home is light and bright and ready for its new owner! Whether you enjoy sipping your coffee on the front porch and talking with your neighbors or heading to your huge backyard to climb some trees or stoke up the fire pit, you will have years of happy memories in this solidly built Winter Haven home. A termite bond is in place, providing you added peace of mind! Located in the heart of Winter Haven, this home offers convenient access to major roadways including US-27 and the Polk Parkway, making commuting and travel simple. Enjoy being just 45–60 minutes to Orlando area attractions, including Walt Disney World and about 1.5 to 2 hours to Florida’s Gulf Coast beaches such as Clearwater and St. Pete Beach. Nature lovers will appreciate the close proximity to some of Florida’s most beautiful outdoor destinations. Nearby options include Circle B Bar Reserve which is known for scenic trails and wildlife viewing or Colt Creek State Park, offering hiking, horseback riding, and camping. Prefert the water? Lake Kissimmee State Park is perfect for boating, fishing, and exploring Florida’s natural landscape. Winter Haven itself is known for its chain of lakes, boating lifestyle, and local charm with shopping, dining, and entertainment just minutes away. Whether you’re looking for a primary residence, seasonal home, or investment opportunity, this property offers comfort, convenience, and access to everything that makes Central Florida special!
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)
Listing Agent: Heather Walker, Pa (407-383-0762)
1280 DENALI DR, WINTER HAVEN, FL 33881
$409,000139 Days on yellowkey MLS ID: G5107453
INCREASED by $10,000 (2.5%) on 04/05/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2566 Built: 2024Monthly Fee: $92 Tax: $6,203 (2025)Community: Lake Lucerne IiSingle Family
Taxes:$6,203
Elementary School: Bethune Academy
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: Virtually Staged. Move-In Incentive Available! Qualified buyers who finance with our affiliated lender may choose one of the following: a 4.5 interest rate or $5,000 toward closing costs (buyer must qualify; incentive applies only when using our affiliated lender). Welcome to this stunning 3-bedroom, 2.5-bath two-story home located on a quiet cul-de-sac in the desirable Lake Lucerne II community. Built in 2024 and beautifully enhanced with thoughtful upgrades, this home offers the peace of new construction with the added value buyers are looking for. The backyard is truly a showstopper, featuring a screened enclosure and backing up to conservation land with a serene pond view, creating the perfect setting to enjoy your morning coffee or unwind at the end of the day. Vinyl fencing along the sides and a rear metal fence preserve privacy without obstructing the view. Inside, the home features high ceilings throughout, luxury vinyl flooring (with carpeted stairs and tile in bathrooms and laundry), an open-concept floor plan, and elegant design touches including a detailed foyer wall and a charming electric fireplace in the living room. The upgraded kitchen boasts stone countertops, beautiful cabinetry, stainless steel appliances, a large island with bar seating, and a pantry, making it ideal for both everyday living and entertaining. Downstairs also includes a flex room perfect for a home office or guest space, a half bath, and a 2-car garage. Upstairs, a spacious loft offers endless possibilities, family room, playroom, or potential 4th bedroom. The primary suite is a true retreat, featuring tray ceilings, generous space for a king-sized bed, and an upgraded California Closet–designed walk-in closet offering exceptional storage and organization. The primary bath includes dual sinks and a walk-in shower. Two additional bedrooms, a full bath, and a well-appointed laundry room with sink complete the upper level. Additional upgrades include a whole-home water filtration system, security system, and a hybrid heat-pump water heater that efficiently heats water while cooling the garage. Enjoy resort-style living with no CDD, a community clubhouse, two pools, and a playground. Conveniently located near shopping, golf courses, and with easy access to I-4, you’re perfectly positioned between Orlando and Tampa, sunrise to sunset. This home is move-in ready and truly special. Schedule your private showing today and experience it for yourself.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Luisa Hurtado (646-259-1153)
3356 AVENUE Q NW, WINTER HAVEN, FL 33881
$297,500309 Days on yellowkey MLS ID: S5132588
REDUCED by $500 (0.2%) on 06/13/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1488 Built: 1980 Tax: $3,556 (2024)Community: InwoodApartment
Taxes:$3,556
Elementary School: Fred G. Garnier Elem
High School: Auburndale High School
Tax Year: 2024
Remarks: BACK ON MARKET — NOW PRICED UNDER $300K! Seller offering a $5,000 buyer closing cost credit. Occupied Winter Haven duplex generating $2,550/month in gross rental income. Both units are 2 bed / 1 bath and feature stone countertops, laminate flooring, and separate living spaces. No carpet. No HOA. No current vacancy. This property offers immediate income from day one with a practical two-unit setup for long-term rental demand. Located in a quiet residential area less than 2 miles from public schools, near Winter Haven’s Chain of Lakes, Lake Shipp Park, public boat ramps, trails, shopping, dining, and approximately 20 minutes from LEGOLAND Florida. Investors looking for an income-producing asset under $300K should take a serious look. Schedule your showing today.
Listing is courtesy of: BANERSY REAL ESTATE, LLC (407-962-6201)
Listing Agent: Enrique Ojeda (321-946-8241)
419 AVENUE M NE, WINTER HAVEN, FL 33881
$244,99935 Days on yellowkey MLS ID: TB8507931
REDUCED by $5,000 (2.0%) on 06/13/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1232 Built: 1946 Tax: $1,957 (2025)Community: Silvercrest AddSpa: NoSingle Family
Taxes:$1,957
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bathroom home offering the perfect blend of comfort, functionality, and style. Step inside to find a bright and inviting floor plan with spacious living areas, abundant natural light, and a warm, welcoming atmosphere throughout. The kitchen features ample cabinet space, and a convenient layout ideal for both everyday living and entertaining with direct access to the back patio. The master bedroom offers a private retreat with an en-suite bathroom and generous closet space that is connected directly to the large laundry room. The additional bedrooms provide flexibility for family, guests, or a home office. Outside, enjoy a spacious, fenced in yard with plenty of room for relaxing, gardening, or hosting gatherings. Conveniently located near Polk State College, Winter Haven schools, and just minutes away from downtown Winter Haven. This home combines peaceful living with everyday convenience. Don’t miss the opportunity to make this move-in-ready home your own!
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
448 ITUNA CIR, WINTER HAVEN, FL 33881
$318,9005 Days on yellowkey MLS ID: L4962701
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1744 Built: 2026Monthly Fee: $50Community: Harbor At Lake HenrySingle Family
Taxes:$0
Remarks: Brand-new, 3-bedroom home for sale! Say hello to life in the Sophia, featuring an open living area with luxury vinyl plank flooring, under an airy volume ceiling! Unwind in your spacious owner's suite complete with a private en-suite bath including a decorative tiled shower, dual vanities, a convenient linen closet, and a walk-in wardrobe! Plus, enjoy outdoor living on your covered lanai! This home includes features and finishes hand-selected by our professional designers to provide you with enduring style, move-in convenience, and easy home maintenance: Beautiful, open kitchen with: A counter-height island Quartz countertops 36-in. shaker-styler cabinets with crown moulding and decorative knobs/pulls Stainless steel undermount sink with a pull-down faucet Walk-in pantry Samsung stainless steel appliances: 5-burner smooth-top electric range with wi-fi smart controls Fingerprint-resistant microwave with ventilation system ENERGY STAR® quiet-operation dishwasher ENERGY STAR® side-by-side refrigerator Low-maintenance luxury vinyl plank flooring throughout the living areas, kitchen, laundry room and all bathrooms Mohawk stain-resistant carpet in all bedrooms Energy-efficient LED lighting in the kitchen and gathering room Custom-fit 2-in. faux wood window blinds Built-in pest control Architectural shingles with limited-lifetime warranty Fully sodded with Florida-friendly landscaping and irrigation system ...and much more! Save on utilities with energy-efficient R-30 insulation, foam-injected block insulation, double-pane Low-E windows, and a programmable thermostat.
Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)
Listing Agent: George Lindsey, Iii (863-797-4999)
308 AVE P NW, WINTER HAVEN, FL 33881
$230,00027 Days on yellowkey MLS ID: L4962121
2 Days Off yellowkey (back on 6/12/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1402 Built: 2025Community: Harrington A B SubHalf Duplex
High School: Lake Region High
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 306 Ave P NW – a fantastic opportunity for first-time home buyers or savvy investors! Now offered as separate units for added affordability and flexibility, this property is perfect for buyers looking to own instead of rent. This well-maintained home features bright living spaces, functional layouts, and great potential to personalize and build equity. Whether you’re looking for your first home, a mortgage helper opportunity, or an affordable investment, this property checks all the boxes. Located in a convenient neighborhood close to schools, parks, shopping, and everyday amenities, you’ll love the value and potential this property offers. Why rent when you can own? Don’t miss your chance to get into the market with this affordable and versatile property. Quick possession available — motivated seller!
Listing is courtesy of: TRUE FLORIDA REALTY LLC (863-337-9667)
Listing Agent: Ricky Miller, Jr (407-453-8679)
306 AVE P NW, WINTER HAVEN, FL 33881
$230,00027 Days on yellowkey MLS ID: L4962119
3006 ELM ST, WINTER HAVEN, FL 33881
$215,00042 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
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
$295,00048 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)
820 AVENUE Z NW, WINTER HAVEN, FL 33881
$197,50020 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
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
$315,00029 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)
1558 DREXEL AVE NE, WINTER HAVEN, FL 33881
$384,00064 Days on yellowkey MLS ID: L4960971
REDUCED by $15,500 (3.9%) on 05/21/2026
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 $15,000 PRICE DROP! Completely renovated and move-in ready, this beautifully updated home combines modern style with everyday comfort in the heart of Central Florida. Step inside to a bright, open floor plan filled with natural light from large floor-to-ceiling windows throughout—including in the bedrooms. The spacious living areas flow seamlessly, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. The stunning kitchen has been completely updated with beautiful soft-close cabinetry, luxurious quartz countertops, stainless steel appliances, and recessed lighting—offering a sleek, contemporary look and exceptional functionality. Luxury vinyl plank flooring runs throughout the home, complemented by fresh interior paint, modern fixtures, and stylish ceiling fans that complete the elegant finish. The primary suite provides a private retreat, while additional bedrooms offer flexibility for family, guests, or a home office. Both bathrooms have been tastefully remodeled with updated tile, vanities, and fixtures. Outside, enjoy your private backyard oasis—fully enclosed with a block wall for enhanced privacy. A sparkling inground pool with paver deck sets the stage for year-round Florida living, whether you’re hosting a gathering or enjoying a quiet evening under the stars. Additional features include a separate exterior laundry/storage room for added convenience. Ideally located near shopping, dining, schools, and major roadways, this home offers easy access to Winter Haven’s famous Chain of Lakes and other nearby Central Florida attractions. Every detail has been updated—move right in and start enjoying the Florida lifestyle today! Schedule your private showing before it’s gone.
Listing Agent: David Small (407-601-8351)
601 LAKE PANSY DR NW, WINTER HAVEN, FL 33881
$765,900154 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
$350,0006 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
$749,90048 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)
117 5TH ST NE, WINTER HAVEN, FL 33881
$484,00043 Days on yellowkey MLS ID: L4961626
0 Days Off yellowkey (back on 5/9/2026)
Bed: 6 Bath: 0.0 Liv Area Sq Ft: 2214 Built: 1930 Tax: $962 (2025)Community: Revised Map Of Fernwood AddApartment
Remarks: Under contract-accepting backup offers. Great opportunity to add to your portfolio or start your rental property journey! Great Quad that has had multiple upgrades and improvements. The best part is the adjacent empty lot that is zoned for another Quadraplex included in the sale! Build another Quad or even a duplex, the possibilities are endless! Consistently rented with one of the units being newly built out. New roof April of 2026! New commercial grade washer and dryer in the common area along with a new large gas water heater for the building in the last year. All units rented - Come and take a look at your next income property! Unit 115 - Upstairs - 2/1 $1350/month Unit 113 - Downstairs - 1/1 $1500/month includes electric Unit 119 - Upstairs - 2/1 $1350/month Unit 117 - Downstairs - 2/1 $1250/month
Listing is courtesy of: REMAX EXPERTS (863-802-5262)
Listing Agent: Stacy Tuttle (863-602-9554)
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