Location: Winter Haven , 33881
Do Not Show Listings
3356 AVENUE Q NW, WINTER HAVEN, FL 33881
$297,500306 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,556
Elementary School: Fred G. Garnier Elem
High School: Auburndale High School
Tax Year: 2024
Middle School: Westwood Middle
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
$244,99932 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
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
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
$318,9002 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)
140 KRENSON BAY LOOP, WINTER HAVEN, FL 33881
$270,0001 Day on yellowkey MLS ID: G5113525
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1479 Built: 2022Monthly Fee: $58 Tax: $3,522 (2025)Community: Krenson BaySpa: NoSingle Family
Taxes:$3,522
Elementary School: Frank E. Brigham Academy
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: Welcome to this inviting 3BR/2BA home with a 2-car garage and 2,128 sq. ft. in a gated Winter Haven community. Features include tile in the main living areas, carpet in the bedrooms, an open kitchen with pantry and dining area, and a primary suite with walk-in closet, dual sinks, garden tub, and separate shower. Enjoy no rear neighbors and backyard views of Lake Maude Natural Park, with convenient access to downtown Winter Haven, Polk State Diamond Plex, and the Chain of Lakes Trail.
Listing is courtesy of: OPTIMA ONE REALTY, INC. (352-243-6784)
Listing Agent: Alexis Ortiz Mendez (321-624-3951)
3014 BUCKEYE POINTE DR, WINTER HAVEN, FL 33881
$309,9902 Days on yellowkey MLS ID: R4911379
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1554 Built: 2022Monthly Fee: $33 Tax: $3,544 (2025)Community: Buckeye PointeSingle Family
Taxes:$3,544
Remarks: Schedule your showing before it’s gone!! Check out this beautiful custom home. It sits on a big corner lot and it is the newest house in the neighborhood. Some of the items this home comes with include 9’4 ceilings, open floor concept, crown molding, St. Augustine grass, irrigation system, insulation injected into the block, custom stone back wall in the living room, ceramic tile, granite counter tops, custom closets, a range hood, real wood cabinets, a back patio pergola, gutters and so much more!! So schedule your showing to see this beauty before its to late.
Listing is courtesy of: FREEDOM PROPERTY AGENT LLC (407-530-4600)
Listing Agent: Santiago Arroyo (863-307-5212)
815 LAKE JESSIE DR, WINTER HAVEN, FL 33881
$620,00030 Days on yellowkey MLS ID: S5149974
REDUCED by $30,000 (4.6%) on 06/12/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4128 Built: 1949 Tax: $7,136 (2025)Community: East View PkwySpa: NoSingle Family
Taxes:$7,136
Elementary School: Auburndale Central Elem
Remarks: Discover this unique Spanish/Mediterranean-inspired estate on an oversized lot across from Lake Jessie on the Chain of Lakes. Featuring a 3BR/2BA main home plus a private 1BR/2BA casita/in-law suite, this property is ideal for multi-generational living, vacation rentals, or income-producing opportunities. The versatile floor plan provides the flexibility to function as a triplex-style investment property. Recent upgrades include a NEW roof, NEW AC, NEW water heater, new casita flooring, and more. Inside, enjoy vaulted ceilings, a fireplace, abundant natural light, and spacious living areas designed for entertaining. Step outside to a resort-style screened saltwater heated pool with new heating, cooling, and saltwater systems. Located on a quiet street with no rear neighbors and NO HOA, there’s plenty of room for boats, RVs, and extra vehicles—just steps from the community boat ramp on Lake Jessie. A rare blend of privacy, flexibility, and investment potential. Don't miss this opportunity! Book your appointment today.
Listing is courtesy of: META ONE REALTY GROUP LLC (407-223-3678)
Listing Agent: Aline Oliveira (407-300-7123)
5872 ROYAL HILLS CIR, WINTER HAVEN, FL 33881
$310,0005 Days on yellowkey MLS ID: P4938974
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1730 Built: 2006Monthly Fee: $25 Tax: $3,749 (2025)Community: Royal HillsSingle Family
Taxes:$3,749
Elementary School: Lake Alfred Elem
High School: Haines City Senior High
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: Seller agrees to contribute up to $10,000 toward the Buyer's allowable closing costs, prepaid expenses, and/or interest rate buy-down with a full-price offer, subject to lender approval. Welcome to Royal Hills, where comfort, space, and convenience come together in this beautifully maintained 4-bedroom, 2-bath home. Situated on a quiet street with no rear neighbors, this move-in-ready property offers a desirable split-bedroom floor plan, mature landscaping, and an abundance of indoor and outdoor living space. Step inside to discover soaring ceilings, abundant natural light, and a versatile layout designed for both everyday living and entertaining. The kitchen, dining area, and living room form the heart of the home, creating an open and inviting gathering space for family and friends. The renovated kitchen features granite countertops, a stylish glass tile backsplash, an island, and a raised breakfast/coffee bar overlooking the living room, allowing the chef to stay connected to the conversation. In addition to the main living area, the home offers a spacious family room that provides endless possibilities. Whether you envision a media room, game room, home office, playroom, fitness space, or second living area, this flexible bonus space can easily adapt to your lifestyle. The private owner's suite is thoughtfully positioned on one side of the home and features vaulted ceilings, a walk-in closet, and an en-suite bath. Three additional generously sized bedrooms and a second full bath are located on the opposite side of the home, providing privacy and flexibility for family or guests. An inside laundry room and two-car garage add convenience to everyday living. Enjoy Florida living year-round from the expansive screened porch, accessible through sliding glass doors and offering plenty of space for outdoor dining, relaxing, or entertaining. The fenced backyard includes a storage shed and a large patio area perfect for grilling and gatherings. Additional features include a water softener system, recently installed appliances, a new garbage disposal, and newer A/C, roof, and windows for added peace of mind. Conveniently located near shopping, dining, entertainment, major highways, Legoland, theme parks, and Lake Lucerne, this exceptional home offers the perfect blend of tranquility and accessibility. Schedule your private showing today and experience all that Royal Hills has to offer! Photos may be virtualy staged. It is the buyers responsibility to verify all listing information.
Listing is courtesy of: XCELLENCE (866-595-6025)
Listing Agent: Felicia Nicholson (863-701-4435)
308 AVE P NW, WINTER HAVEN, FL 33881
$230,00024 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
$230,00024 Days on yellowkey MLS ID: L4962119
3006 ELM ST, WINTER HAVEN, FL 33881
$215,00039 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
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
$295,00045 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
$197,50017 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)
4111 ISLAND LAKES DR, WINTER HAVEN, FL 33881
$399,90018 Days on yellowkey MLS ID: O6411190
0 Days Off yellowkey (back on 6/12/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1998 Built: 2012Monthly Fee: $17 Tax: $4,556 (2025)Community: Island LakesSingle Family
Taxes:$4,556
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained waterfront home on an oversized lot in the desirable Island Lakes community. This contemporary residence combines comfort, functionality, and breathtaking lake views. Step inside to discover an open-concept floor plan with soaring cathedral ceilings, abundant natural light, and a desirable split-bedroom layout. The spacious primary suite has views of the lake and access to the screened in back porch. The ensuite includes a large walk-in closet, dual vanity, soaking tub, shower and private water closet. The comfortable great room flows seamlessly into the kitchen and dining areas, creating the perfect setting for everyday living and entertaining. Secondary bedrooms are generously sized and perfect for family and guests. The true highlight of this property is the direct frontage on Lake Rochelle, part of Winter Haven's renowned Chain of Lakes. Your private dock is perfect for fishing or parking your boat. Enjoy peaceful views and breezes from the screened rear porch overlooking the water. Roof replaced in 2024, all new LVP in the family and dining rooms. Whether you enjoy boating, fishing, water sports, or simply relaxing by the lake, this property offers the Florida lifestyle you've been dreaming of. Pack your bags and move in today!
Listing Agent: Amy Moline (407-506-7447)
5780 LAKESIDE LANDINGS BLVD, WINTER HAVEN, FL 33881
$315,00026 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
$384,00061 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)
1540 N LAKE MIRROR DR NW, WINTER HAVEN, FL 33881
$919,900374 Days on yellowkey MLS ID: P4934907
REDUCED by $30,100 (3.2%) on 06/12/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3885 Built: 1967 Tax: $6,494 (2025)Community: Mirro MacSingle Family
Taxes:$6,494
Elementary School: Inwood Elem
Remarks: Lakefront living on the Winter Haven Chain of Lakes takes on a completely different feel at The Guest House, a rare Mid-Century Modern residence designed and built by internationally recognized architect Gene Leedy. Quietly tucked away at the end of a cul-de-sac on the crystal-clear waters of Lake Mirror, the setting feels surprisingly hidden despite being just minutes from shopping, dining, and convenient access to Lakeland, the Polk Parkway, and Interstate 4 for an easy commute between Tampa and Orlando. Originally commissioned for Thelma Guest, "The Guest House" is a striking example of Leedy’s signature architectural style, blending precast concrete construction, dramatic cantilevered forms, walls of glass windows and doors, deep overhangs, and natural light in a way that still feels timeless today. From the street, the design sits perfectly among mature trees and lush landscaping, setting the stage for what awaits inside. The layout was thoughtfully designed around openness, symmetry, and connection to the outdoors. A towering two-story glass entry and interior atrium create an immediate architectural focal point, while the open staircase and original vintage elevator add both character and functionality between levels. The main living spaces are positioned upstairs to maximize natural light and elevated lake views, with expansive glass overlooking the pool, shoreline, and towering oaks draped in Spanish moss. Nearly every upstairs bedroom and living area opens onto long covered balconies, creating seamless indoor and outdoor living. Downstairs offers an entirely different experience with additional flexible living areas surrounding the central atrium and opening directly to the lakefront grounds and pool area . The heated salt-filtered pool feels perfectly integrated into the original architecture, framed by Leedy’s iconic double “T” beam design and expansive covered patios that naturally extend the living space outdoors. The clean geometry, broad overhangs, and shaded entertaining areas create a resort-like atmosphere that feels both private and connected to the lakefront setting. The property itself offers direct frontage on beautiful Lake Mirror , known for its clear water, scenic shoreline, and access to the larger Winter Haven Chain of Lakes — a connected system of more than 20 lakes popular for boating, skiing, fishing, waterfront dining, and exploring by water. A lightly used public boat ramp located immediately next door makes launching effortless without sacrificing usable shoreline space on the property itself. Additional highlights include solar panels, tasteful modern updates, integrated storage and closet systems true to the Mid-Century aesthetic, two covered carports, circular drive, low-maintenance landscaping, and no HOA restrictions. Rarely does a home combine architectural significance, true Chain of Lakes waterfront living, privacy, and Central Florida convenience in such a compelling way. The Guest House is more than a lakefront residence — it is a piece of Winter Haven architectural history.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Michael Stone (863-412-9733)
601 LAKE PANSY DR NW, WINTER HAVEN, FL 33881
$765,900151 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
$350,0003 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
$749,90045 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
$484,00040 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
Taxes:$962
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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