Location: Winter Haven
Do Not Show Listings
204 AVENUE D NE, WINTER HAVEN, FL 33881
$265,0003 Days on yellowkey MLS ID: O6413665
Bed: 6 Bath: 3.0 Liv Area Sq Ft: 2102 Built: 1915 Tax: $1,902 (2025)Community: Winter Haven HeightsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,902
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Prime mixed-use redevelopment opportunity in one of Winter Haven’s most strategic growth corridors. Situated directly across from Winter Haven Hospital, this property offers exceptional potential for investors, builders, and developers seeking to capitalize on a location positioned for long-term growth and redevelopment. The property is located within a Mixed-Use (MU) district that allows up to four residential dwelling units per lot and building heights of up to four stories, creating significant flexibility for residential, mixed-use, or income-producing projects. Its highly desirable location near major employment centers, medical services, retail, dining, and downtown Winter Haven further enhances its development appeal. An exceptional opportunity exists to assemble a larger development footprint through the acquisition of the adjacent parcel at 203 Ave C NE (see separate MLS#O6414107), as well as 209 Ave C NE (coming soon), offering the potential for a multi-parcel redevelopment project in a high-demand area. Opportunities of this scale and location are increasingly rare in Winter Haven. Whether acquired individually or as part of a larger assemblage, this property presents a compelling investment opportunity for developers seeking density, flexibility, and a premier location directly across from one of the area’s largest healthcare campuses.
Listing is courtesy of: MBA REALTY GROUP, INC (407-291-4665)
Listing Agent: Paola Arias (407-969-9211)
2710 AVENUE J NW, WINTER HAVEN, FL 33881
$179,0003 Days on yellowkey MLS ID: TB8515967
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 672 Built: 1956 Tax: $2,320 (2025)Community: InwoodSpa: NoSingle Family
Taxes:$2,320
Remarks: Welcome to a NO HOA 2 bedroom 1 bath located right between Orlando and Tampa. This starter home is close to everything you need plus wonderful lakes, nature trails, Legoland, and more. Walking into the living room there is plenty of space for unwinding after a long day. The first bedroom is connected to the livingroom. Just to the left of the livingroom is the kitchen. In the kitchen there is plenty of storage and cooking space. The next bedroom is just outside the kitchen. Both bedrooms provide all the essentials and boast a ceiling fan. The side door from the kitchen leads to the carport which could easily act as an awesome covered outdoor space. Walking around the house, a large yard for family activities welcomes you. Come find out why you should make this home yours. Ask about Seller Financing Terms.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Gregory Watson (863-224-6431)
341 MANDOLIN LN, WINTER HAVEN, FL 33884
$439,0003 Days on yellowkey MLS ID: L4962452
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2506 Built: 2011Monthly Fee: $56 Tax: $4,408 (2025)Community: MandolinSingle Family
Taxes:$4,408
Remarks: Welcome to Mandolin! Fall in love with this 4-bedroom, 2-bathroom SALT WATER POOL home PLUS a flex room/office offering an impressive 2,506 square feet of living space in a highly desirable gated community. You’ll appreciate the exceptional curb appeal, extended driveway, detailed custom trim work, Luxury Vinyl Plank and tastefully added upgrades throughout the home. Discover a spacious split floor plan featuring elegant accents that welcome you in. The kitchen features granite countertops, solid wood cabinets, NEWER appliances and a large pantry.The oversized indoor laundry room makes your life easy! The flexible office/den space is perfect for working from home, a playroom, fitness area, or additional guest space. The spacious primary suite is privately tucked away and features oversized his-and-her walk-in closets along with a beautifully remodeled primary bathroom complete with an enlarged walk-in shower, stylish new tile and backsplash, and a relaxing separate garden tub. Three additional generously sized bedrooms provide plenty of room for family and guests. Step outside to your own private backyard retreat and enjoy days of fun in the sun featuring a newly added heated saltwater pool and pool cage, screened porch, patio paver deck, and fully fenced backyard with double gate—perfect for entertaining, relaxing, and enjoying the Florida lifestyle year-round. You can also store your boat or outdoor toys! Additional features include termite bait system, regular pest control maintenance, and much more! Conveniently located near Legoland, the Chain of lakes, schools, shopping, medical facilities, restaurants, an all Winter Haven has to offer. Easy commute to all Central Florida Attractions and Florida Beaches! Call today for your showing!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Tina Heim, Pa (863-370-1786)
896 EAGLE ROCK TER, WINTER HAVEN, FL 33880
$399,9008 Days on yellowkey MLS ID: L4962338
REDUCED by $5,000 (1.2%) on 06/02/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1632 Built: 2022Monthly Fee: $38 Tax: $3,355 (2025)Community: Eagle Lndg Ph IbSpa: YesSingle Family
Taxes:$3,355
Remarks: *****BELOW APPRAISAL VALUE***EASY TO SHOW +++ LUXURY AND REMODELED MOVE-IN READY POOL HEATED HOME IN EAGLE LANDING! Welcome to this stunning, fully upgraded corner-lot residence located in the highly desirable Eagle Landing community—just minutes from LEGOLAND and ideally situated between Tampa and Orlando. Built in 2023, this beautifully enhanced home offers the perfect blend of modern design, comfort, and resort-style living. The open-concept floor plan creates a bright and spacious atmosphere, ideal for both everyday living and entertaining. The chef-inspired fully remodeled kitchen features brand-new cabinetry and elegant granite countertops, seamlessly flowing into the main living areas for a clean, modern feel. Both bathrooms have been completely remodeled with stylish tile finishes and granite vanities, adding a touch of luxury throughout the home. Step outside to your private backyard oasis, featuring a 16' x 22' saltwater pool, lights with a heater for year-round enjoyment, a relaxing spa/hot tub, and a fully screened enclosure. The outdoor space is finished with beautiful pavers and a fully fenced yard, perfect for entertaining or simply relaxing in privacy. Additional highlights include: ?? 2023 construction ?? Fully remodeled kitchen with new cabinets & granite countertops ?? Smart home technology to control your home & pool ?? Saltwater pool (16’ x 22’) with heater + spa/hot tub/ heated ?? Screen enclosure + pavered outdoor living space ?? Fully vinil fenced backyard for privacy and entertainment. ? New front entry door with decorative glass and upgraded hardware. ? Block-on-block construction for durability and peace of mind. ? Architectural shingles and modern stucco exterior for lasting curb appeal. ? Spacious corner lot offering extra privacy and outdoor space. This home featuring modern, nearly new furniture throughout—making it truly turnkey. The only exception is the primary bedroom set, which includes a king-size bed. With its prime location, luxury upgrades, and resort-style amenities, this property is perfect as a primary residence, vacation home, or investment opportunity. ?? Eagle Landing – Winter Haven, Florida ?? Schedule your private showing today before it’s gone!
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Ingrid Reyes (863-838-6863)
900 LAKE JESSIE DR, WINTER HAVEN, FL 33881
$450,00073 Days on yellowkey MLS ID: S5146723
REDUCED by $19,900 (4.2%) on 06/06/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1828 Built: 1948 Tax: $4,023 (2025)Community: East View PkwySpa: NoSingle Family
Taxes:$4,023
Elementary School: Auburndale Central Elem
High School: Auburndale High School
Middle School: Westwood Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to a place where everyday life feels like a getaway. Set along the peaceful shores of Lake Jessie, part of Winter Haven’s renowned Chain of Lakes, this lakefront retreat is more than just a home, it’s a lifestyle defined by water, sunshine, & unforgettable experiences. Start your mornings with breathtaking sunrises shimmering across the lake, coffee in hand from your private dock or patio. Spend your days exactly how you choose, cruising the Chain of Lakes by boat, casting a line in some of Central Florida’s best freshwater fishing, or enjoying world-class watersports like skiing, wakeboarding, and paddleboarding right from your backyard. With nearby slalom courses & open water, this is truly a paradise for water enthusiasts. Lake Jessie is especially cherished for its tranquil atmosphere, offering a rare sense of calm while still being full of life. One of its most unique features is the seaplane activity, where you can watch planes gracefully land and take off across the water, an experience that never gets old and adds to the charm of lakeside living. Nature lovers will also appreciate the frequent sightings of all kinds of birds and other beautiful wildlife. The home itself offers a thoughtfully designed single-story layout with over 1,800 square feet, featuring 3 bedrooms and 3 bathrooms. An open-concept living space is filled with natural light and showcases stunning lake views, while a split-bedroom design provides comfort and privacy. A private in-law suite with its own entrance adds flexibility for guests, multi-generational living, or additional income potential. This residence offers plenty of parking space with it's oversized driveway & an additional carport providing covered parking as well. The home has been updated with modern finishes and includes a metal roof installed in 2019. This home would make a perfect full time residence, investment property or second home. Beyond the water, the location is just as appealing. You’re right around the corner from a brand new Publix store and minutes from the heart of Winter Haven, where you’ll find charming local restaurants, shops, parks, and community events. Legoland Florida Resort is just a short drive away and there is convenient access to both Tampa and Orlando, so world-class attractions, dining, and entertainment are always within reach. Whether you're seeking adventure, relaxation, or a smart investment, this Lake Jessie property delivers it all, offering the rare opportunity to live, play, and unwind in one of Florida’s most iconic lakefront settings. Book your showing today!
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
1540 N LAKE MIRROR DR NW, WINTER HAVEN, FL 33881
$950,000369 Days on yellowkey MLS ID: P4934907
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
High School: Winter Haven Senior
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)
1280 W LAKE HAMILTON DR, WINTER HAVEN, FL 33881
$1,259,0006 Days on yellowkey MLS ID: L4961525
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 5416 Built: 1995 Tax: $7,019 (2025)Community: N/ASingle Family
Taxes:$7,019
Elementary School: Elbert Elem
Middle School: Denison Middle
Remarks: Spanish-inspired architecture, artistic flair, and breathtaking lakefront scenery come together in this truly one-of-a-kind estate on the shores of Lake Hamilton. Situated on more than one acre of fully fenced waterfront property with a wrought-iron gated entrance and no HOA restrictions, this custom residence offers over 5,400 square feet of living area designed for both grand entertaining and everyday enjoyment of Florida's lakefront lifestyle. From the moment you arrive, the home's distinctive architectural design makes a lasting impression. A circular driveway leads to the large covered portico where a tranquil fountain welcomes guests and creates an unforgettable arrival experience. Stepping through the double doors reveals a dramatic foyer with soaring ceilings, abundant natural light, and immediate panoramic lake views. Throughout the home, artistic influence and personality are evident at every turn. One of the owners is an accomplished artist, and their creativity is beautifully reflected in the home's unique design elements, decor, and inviting spaces. The completely remodeled kitchen, updated in 2018, serves as the heart of the home and features extensive custom cabinetry, granite countertops, a striking raised glass breakfast bar, center island with a built-in wine trough, and a bright eat-in dining area overlooking the lake. Nearby, the formal dining room provides the perfect initimate setting for holiday gatherings and special occasions. Designed with flexibility in mind, the home offers multiple living and entertaining spaces including a spacious family room anchored by a fireplace, dedicated office, theater room, enclosed Florida room stretching across the rear of the home, and numerous areas for relaxation or hosting guests. The expansive Florida room is the ideal place to begin each day with coffee while watching spectacular sunrises paint the sky over the water. The first floor features three generously sized guest bedrooms, while the private owner's retreat occupies the upper level. This luxurious sanctuary enjoys elevated wraparound views of Lake Hamilton, creating a peaceful escape unlike anything else in the area. Also located above is a unique artist's perch or widow's walk, offering an elevated vantage point to enjoy panoramic views, morning and evening skies, wildlife watching, and endless inspiration. Outdoor living is equally impressive. The heated salt-filtered pool, completed in 2018, overlooks the lake and creates a resort-style atmosphere. Expansive paver decking and wide-open lawn areas provide ample room for family gatherings, pets, and outdoor recreation. A composite dock extends into Lake Hamilton, making it easy to enjoy boating, fishing, paddleboarding, and sunset cruises. Spanning nearly 1,900 acres, Lake Hamilton is widely known for its excellent fishing, boating opportunities, and scenic beauty. Cruise across the lake to enjoy dining and entertainment at local favorites such as Floridino's and Port 27 before returning home for a peaceful sunset ride across the water. Additional features include a detached two-car garage, large storage shed and the privacy and freedom that comes with having no HOA. Rarely does a property combine architectural character, artistic expression, expansive living space, resort-style amenities, and over an acre of lakefront land in such a remarkable setting. This is more than a home—it is a private waterfront retreat where every sunrise feels like a work of art.
206 DILLON ST, WINTER HAVEN, FL 33880
$215,00017 Days on yellowkey MLS ID: L4962158
0 Days Off yellowkey (back on 6/6/2026)
REDUCED by $2,000 (0.9%) on 06/03/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1017 Built: 1996 Tax: $1,600 (2025)Community: Jan Phyl VillageSingle Family
Taxes:$1,600
Elementary School: Pinewood Elem
High School: Lake Region High
Remarks: Under contract-accepting backup offers. 3 bedroom, 2 bathroom concrete block home with a 1-car garage situated on a corner lot in the Jan Phyl Village area of Winter Haven with NO HOA. Several major updates were completed in 2021 including the roof, kitchen, flooring, guest bathroom flooring, and hot water heater. The home also features a newer dishwasher and new garage door. The backyard provides a great space for relaxing or entertaining. Conveniently located near Polk Parkway access, shopping, dining, schools, and surrounding Central Florida areas for an easier commute. Located in an established neighborhood with friendly neighbors and just a short distance from Winter Haven’s Chain of Lakes area. A solid option for a primary residence or investment property at an affordable price point.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Aubrie Flint (863-618-6347)
47 ENCLAVE DR, WINTER HAVEN, FL 33884
$245,000104 Days on yellowkey MLS ID: P4937867
REDUCED by $15,000 (5.8%) on 05/05/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1444 Built: 1999Monthly Fee: $433 Tax: $3,221 (2025)Community: Cypresswood Enclave Ph 2Spa: NoVilla
Taxes:$3,221
Remarks: PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, and the Interior was Freshly Painted. Be sure to take time to enjoy the view from your Screened Porch. There are No Homes behind you, just open pastures, roaming cows, and trees. Very peaceful. The HOA fee also includes the Landscaping, Lawn Maintenance, Exterior Painting, and Roof (replaced in 2023) for your Villa. This Home allows you to relax and enjoy a game of Golf, take a swim in the Olympic Pool, or just enjoy the view from your Screened Porch. The Home is located close to Shopping (New Publix), Restaurants, Downtown, and Highway 27 which leads to Interstate 4 for Tampa and Orlando (Disney World). Come see what this home can offer you!
Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)
Listing Agent: David Shippey (863-521-4517)
800 WARE AVE NE, WINTER HAVEN, FL 33881
$242,99954 Days on yellowkey MLS ID: O6399008
REDUCED by $1,996 (0.8%) on 06/06/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1000 Built: 2023 Tax: $1,293 (2025)Community: Swan Lake EstatesSingle Family
Taxes:$1,293
Remarks: Welcome to 800 Ware Ave NE, Winter Haven, FL, TENANT OCCUPIED, a fantastic opportunity for both investors and future homeowners alike! This 3-bedroom, 2-bathroom home features a desirable open floorplan with durable laminate flooring throughout, creating a seamless and low-maintenance living space. Situated on a spacious corner lot, the property also offers a fully fenced yard, perfect for added privacy, pets, or outdoor enjoyment. EXCELLENT INVESTMENT opportunity with a reliable, good-paying tenant already in place through January 2027, providing immediate and consistent income. Enjoy the peace of country-style living while remaining just minutes from Winter Haven’s Chain of Lakes, as well as nearby shopping, dining, and world-famous Central Florida attractions like LEGOLAND, Disney, and Universal Studios. The home also includes a dedicated utility/laundry room and the benefits of a newer, energy-efficient build, making it truly move-in ready and built for long-term value. Don’t miss your chance to secure this income-producing property or future home, schedule your private tour today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Veronica Figueroa (407-519-3980)
6103 GREY HERON DR, WINTER HAVEN, FL 33881
$304,99940 Days on yellowkey MLS ID: O6403532
REDUCED by $1 (0.0%) on 06/01/2026
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)
271 INMAN BLVD, WINTER HAVEN, FL 33881
$350,000186 Days on yellowkey MLS ID: W7881213
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2274 Built: 2024Monthly Fee: $49 Tax: $1,347 (2024)Community: Inman GrovesSpa: NoSingle Family
Taxes:$1,347
Tax Year: 2024
Remarks: PRISTINE AND MOVE-IN READY! Seller is offering up to $5,000 concession towards closing costs and prepaids. Come and see this barely lived in 5 BEDROOM, 2.5-BATH home nestled in the solar-friendly community of INMAN GROVES. Built in 2024 and set on a corner lot with NO REAR NEIGHBORS, this home offers peaceful views, unbeatable privacy, and all the advantages of brand-new construction—without the wait. Step inside and be greeted by a bright and open first floor layout designed for effortless living and entertaining. The spacious great room flows seamlessly into the stunning kitchen, featuring QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES, A LARGE CENTER ISLAND, SPACIOUS PANTRY, and ABUNDANT CABINET SPACE. The adjacent dining area makes gathering and conversation feel natural and inviting. A HALF BATH and INSIDE LAUNDRY ROOM add everyday convenience. Upstairs, a VERSATILE LOFT offers the perfect second living space ideal as a TV lounge, playroom, homework hub, or home office. Tucked away in its own private corner is the PRIMARY BEDROOM, complete with an oversized WALK-IN CLOSET and spa-inspired en-suite bathroom with DUAL SINKS, QUARTZ VANITY, and an elegant WALK-IN TILE SHOWER. FOUR SPACIOUS SECONDARY BEDROOMS are thoughtfully arranged around a full bathroom with dual sinks, making room for everyone. Step outside to your FENCED BACKYARD, where a patio awaits—perfect for grilling, lounging, and enjoying Florida’s year-round sunshine. Enjoy low utility costs with your energy-efficient SOLAR PANELS leased at only $93/month. Home is located just off Dundee Road and gives you quick access to Hwy 27, Hwy 17 and Polk Parkway, theme parks like Legoland, Disney and Universal. Close to Winter Haven downtown, hospitals, restaurants, breweries, Chain of lakes and Florida beaches. With contemporary design, energy savings, and an unbeatable location, this home checks every box. Don’t miss your chance to make 271 Inman Blvd your New Haven—schedule your private showing today!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (352-688-2227)
Listing Agent: Isabelle Maye (540-840-8849)
117 4th JPV ST, WINTER HAVEN, FL 33880
$190,000126 Days on yellowkey MLS ID: TB8472143
REDUCED by $28,000 (12.8%) on 05/29/2026
Bed: 3 Bath: 1.5 Gar: 2 Liv Area Sq Ft: 1224 Built: 1957 Tax: $2,572 (2025)Community: Jan Phyl Village Unit 02 Pb 37 Pg 50Single Family
Taxes:$2,572
Remarks: Under contract-accepting backup offers. Looking for the perfect starter home or turnkey investment? Welcome to 117 4th Ave N! This well-maintained 3-bedroom, 1.5-bath home has been lovingly cared for by the same family for over 40 years and is now ready for its next chapter. Situated just minutes from shopping and dining, this property delivers both comfort and convenience in the heart of Winter Haven. Recent updates include a brand-new roof (2025), providing peace of mind and long-term value. For investors, current tenants are interested in staying—offering an immediate income opportunity if desired. Inside, you'll find an open and inviting floor plan where the kitchen flows seamlessly into the spacious living room. Each bedroom offers generous space with nice-sized closets, perfect for growing families or long-term renters. But here's the bonus: attached to the back of the home is additional flex space not included in the square footage. This area could easily be converted into a 4th bedroom, mother-in-law suite, home office, or studio—adding even more value and versatility to the property. Parking is another standout feature with a covered carport plus a detached garage—ideal for extra vehicles, storage, or workshop space. Priced to sell and brimming with potential, this gem won't last long.
Listing is courtesy of: FIVE STAR REAL ESTATE OF FLORIDA LLC (904-539-3336)
Listing Agent: Arina Reid-Martin (770-500-0514)
329 LAKE DAISY LOOP, WINTER HAVEN, FL 33884
$320,00026 Days on yellowkey MLS ID: G5112198
REDUCED by $10,000 (3.0%) on 05/31/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1563 Built: 1995 Tax: $3,888 (2025)Community: Lake Daisy EstatesSingle Family
Taxes:$3,888
Remarks: 329 Lake Daisy Loop | NO HOA Welcome to this beautiful 3BR/2BA home in Lake Daisy Estates, offering over 1,500 sq. ft. of comfortable living space on a spacious corner lot—and best of all, NO HOA, giving buyers the freedom they want. This home features a bright formal living and dining area, a spacious kitchen with Frigidaire appliances, and a large family room with vaulted ceilings and a wood-burning fireplace. Sliding doors open to a generous enclosed patio, perfect for relaxing or entertaining. The master suite includes a walk-in closet, jetted tub, separate shower, double sinks, and private access to the patio. Additional highlights include: Marble flooring installed in 2025, New AC (2025), Roof replaced in 2017, Window shades installed in 2025, Indoor laundry room 2-car garage Located just minutes from Legoland (5 min), Walmart (4 min), shopping centers, restaurants, schools, and medical facilities. A fantastic opportunity in a prime location with no HOA—highly attractive for today’s buyers.
Listing is courtesy of: LA ROSA RTY WINTER GARDEN LLC (407-614-5158)
Listing Agent: Jasmin Vargas (407-747-2367)
2235 LAKERIDGE DR, WINTER HAVEN, FL 33881
$305,00060 Days on yellowkey MLS ID: P4938412
REDUCED by $10,000 (3.2%) on 05/14/2026
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)
551 LAKE SMART BLVD, WINTER HAVEN, FL 33881
$344,90071 Days on yellowkey MLS ID: S5146731
REDUCED by $15,000 (4.2%) on 05/30/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1936 Built: 2020Monthly Fee: $50 Tax: $4,211 (2025)Community: Lake Smart PointeSingle Family
Taxes:$4,211
Remarks: HUGE PRICE REDUCTION! Looking to buy a home in Winter Haven Florida? Welcome to 551 Lake Smart Blvd, a stunning move in ready residence featuring a brand new roof replaced in 2025. This beautiful home features 4 bedrooms, 2 bathrooms, and 1936 square feet of open concept living space. Imagine relocating to central Florida and stepping into a bright, airy floor plan where natural light fills the generous living spaces and connects seamlessly to a modern kitchen. Picture yourself enjoying a spacious yard or hosting gatherings in a versatile layout designed for effortless living. Remote workers and commuters will love the strategic location along the I-4 corridor, offering a quiet retreat with easy access to both Tampa and Orlando. To make your move even smoother, the seller is offering a $5000 dollar contribution toward buyer closing costs alongside a 1 year home warranty. This property delivers affordable modern comfort just minutes from dining, shopping, and major roadways. It is incredibly easy to tour, schedule your private showing today.
Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)
Listing Agent: Kenneth Gonzalez (407-860-2304)
207 AVENUE E SE, WINTER HAVEN, FL 33880
$425,00033 Days on yellowkey MLS ID: L4961631
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2093 Built: 2026 Tax: $3,201 (2025)Community: Twin Oaks Add Pb 12 Pg 16Single Family
Taxes:$3,201
Remarks: This is the ONE! Great location centrally located in Winter Haven. Needing an attached Mother N Law suite with a separate entrance or want an Air BNB. This is the perfect set up. This can be considered as a duplex, since the units are entirely separate. Main home has had total renovations. New trusses, installation, windows, doors, roof, floors, kitchen, baths, sheetrock & tankless water heater. Open plan with dining/kitchen combo. Kitchen features stainless steel appliances, granite counter tops, range, refrig, dishwasher and pantry. Enjoy your spacious front covered porch in the shade. This home features porcelain tile & wood laminate throughout and offers plenty of off street parking spaces. How many vehicles you can park depends on the size of your vehicles. There is space to park an RV. The attached Mother N Law suite or Air BNB has a private entrance. It is attached to the main home but there is not an entrance between the 2 homes. The 2nd home is new construction and features an open floor plan with porcelain tile & wood laminate flooring. This home features a full size kitchen with stainless steel appliances, granite counter tops, range, refrig, dishwasher and double sinks. The living area if open to the kitchen & dining area. The home features 2 bedroom and 2 baths. One bath has a tiled walk-in shower, the other bath has a tub/shower combo & both have granite vanity tops. This home features a large “Recreation or Flex Room.” Each home has it's own HVAC unit with separate meters.
Listing is courtesy of: ADVANTAGE REALTY 1 (863-386-1111)
Listing Agent: Sharon Jones Pa (850-341-9216)
241 GROVE BRANCH RD, WINTER HAVEN, FL 33880
$234,900256 Days on yellowkey MLS ID: L4956146
REDUCED by $5,000 (2.1%) on 05/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1140 Built: 2009Monthly Fee: $57 Tax: $3,774 (2024)Community: Squires GroveSingle Family
Taxes:$3,774
Remarks: Charming 3-Bedroom, 2-Bathroom Home – Move-In Ready! Welcome to this well- maintained, single-family home, located in the desirable Squires Grove subdivision in Eagle Lake. Step inside to find brand new commercial-grade, waterproof, laminate flooring throughout. The spacious living room is perfect for relaxing and entertaining, while the kitchen includes a cozy dinette area. Enjoy Florida living at its best with a screened-in back patio, complete with lighting and tile flooring. The patio opens up to your large back yard. This home also includes a two-car garage. BRAND NEW A/C system installed in March 2025, ensuring comfort year-round and a NEW roof coming soon!
Listing is courtesy of: REMAX EXPERTS (863-802-5262)
Listing Agent: Tony Fridovich (863-698-4267)
5137 WINGED FOOT LN, WINTER HAVEN, FL 33884
$380,00060 Days on yellowkey MLS ID: P4938411
1 Days Off yellowkey (back on 6/6/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2107 Built: 2006Monthly Fee: $5 Tax: $3,291 (2025)Community: Lake Ashton West Ph 01Single Family
Taxes:$3,291
Remarks: Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this delightful, remarkably private, and fully updated 3-bedroom, 2-bath home awaits your arrival. To the west lies a forested nature preserve that circles to the north and then east, providing absolute privacy on two sides of the oversized lot and creating a serene, natural backdrop to everyday living. The exterior of the house was freshly painted in 2025, and the roof was replaced on December 29, 2022, offering both beauty and peace of mind. As you approach the home, you will immediately notice the greatly expanded paver driveway and the inviting front screened enclosure at the entryway. The home’s gorgeous front door with sidelights offers a gracious welcome and sets the tone for what awaits inside. Stepping through the entry, you will appreciate the lovely porcelain tile flooring, the tasteful paint color palette, chair railing in the dining area, and elegant crown molding that adds a refined touch throughout. Three solar tubes provide abundant natural light, creating a bright and cheerful interior. The kitchen has been thoughtfully updated with all appliances replaced, including a new refrigerator installed in April 2026. The kitchen floor is marble, and all counters are granite, combining durability with timeless style. The second bedroom hosts a Murphey bed. Extending the living space is the impressive 10’ by 26’ tiled veranda, which is fully enclosed and air conditioned, providing comfortable additional living space year-round. Just outside the veranda, a 14’ by 26’ screened and pavered enclosure offers the perfect setting for entertaining guests or simply relaxing while enjoying the peaceful, natural surroundings and the soothing sounds of nature. Residents of Lake Ashton enjoy unmatched amenities, including two championship 18-hole golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, both indoor and outdoor swimming pools, a movie theater, pickleball courts, a bowling alley, and so much more, creating an active and fulfilling lifestyle. This exceptional property offers the perfect blend of comfort, convenience, and community. Schedule your private showing today and experience the very best of Florida living.
Listing is courtesy of: GLOBAL LIFESTYLE LLC (727-455-2709)
Listing Agent: Brad Kirwan (863-280-0390)
2207 AVENUE F NW, WINTER HAVEN, FL 33880
$255,00012 Days on yellowkey MLS ID: TB8513310
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1310 Built: 1946 Tax: $2,679 (2025)Community: Beymer Stoner SubSingle Family
Taxes:$2,679
Remarks: Charming and well-maintained home in Winter Haven featuring gorgeous wood flooring throughout the main living areas and porcelain ceramic tile in the kitchen. The beautifully updated kitchen features stainless steel appliances, a gas stove, soft-close cabinets, and ceramic tile flooring, offering both style and functionality. The front enclosed sunroom is filled with beautiful natural morning light through surrounding windows, creating the perfect space to relax, enjoy your coffee, or unwind throughout the day. Conveniently located near several beautiful lakes; including Lake Howard, this property offers the best of Florida living while being situated in a FEMA-designated dry zone outside of the flood area for added peace of mind. Enjoy major energy savings with the fully paid-off solar panel system already in place, helping keep electric bills low for the new owner. Additional updates include a newer roof and AC system, along with a full-house gas generator capable of powering the entire home during storms or outages with the flip of a switch. The spacious backyard workshop provides ample room for tools, hobbies, storage, or workspace needs. Conveniently located near shopping, dining, parks, and recreational opportunities, this property is ideal for buyers seeking comfort, efficiency, preparedness, and functionality all in one. Schedule your private showing today!
Listing is courtesy of: SOUTHERN PINE REALTY GROUP, LLC (813-525-7313)
Listing Agent: Elda Romero (813-957-1212)
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