Displaying: For Sale
Location: Winter Haven
Property Type(s): Single Family
Price: $400,000 to $499,000
Do Not Show Listings
Winter Haven - 51 properties found
126 LAKE REGION CIRCLE, WINTER HAVEN, FL 33881
$400,000200 Days on yellowkey MLS ID: P4936583
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2142 Built: 2003Monthly Fee: $95 Tax: $3,169 (2025)Community: Gates Of Lake RegionSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,169
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: ALMOST PARADISE! Enjoy the peaceful surroundings and relaxing environment from this 2142 SF executive style home located in The Gates of Lake Region, a well maintained and GATED community close to the Winter Haven Country Club! NEED SPACE? This customized 4BR/2BA home was designed with an open floor plan with split bedrooms, formal dining room and living room ( which could be easily used as a study, library and/or den), family room and interior laundry room. Note the Curb Appeal of the landscaping, TILE ROOF and BRICK paver driveway and walkway! The inviting and covered front porch provides respite from inclement weather. As you enter the entry foyer, the living room will be to the immediate left and the dining room to the right. Straight ahead is the family room with a set of sliding glass doors that opens onto the screened in lanai. Settle back, listen to the birds singing and observe the cows on the adjacent ranch property! To the left of the family room are bedrooms #2 and #3 and to the right is the kitchen, dining nook, primary bedroom suite, bedroom #4 and the laundry room! The well planned kitchen has a breakfast bar, white cabinetry with neutral colored solid countertop and stainless steel appliances. The kitchen appliances have been updated from 2018-2025. The spacious primary suite has sliding glass doors leading to the lanai, two walk-in closets and an ensuite bathroom with dual vanities and sinks, jetted tub, separate shower and a water closet! Bedroom #4 is currently used as a home office. The floor plan allows creativity in use. Most recent updates include: Water Heater replaced Feb. 2026; AC/Heat system April 2025; garbage disposal and microwave 2025; and lanai screen & door 2025. The PERIMETER 90 X 120 lot is a generous in size. There is room to add a pool, outdoor kitchen, play area and/or garden! The HOA fee provides re-use irrigation water and maintenance of the gate and common areas. Perfect for a year round or winter residence, this home is a blank canvas just waiting for YOUR decorating touches! For those who enjoy golf and/or tennis, the Country Club of Winter Haven is just 2 Blocks away! Publix Supermarket and additional stores are currently under construction and are located within 0.8 mile! Easy access to downtown Winter Haven, HWY 27 and I-4. Legoland, Bok Tower, world-famous theme parks of Disney, Universal Orlando, Sea World, water adventure parks, downtown Orlando and various other nature parks are within a 7 to 60 mile drive. Be sure to make your appointment to view this outstanding property! Measurements are approximate. All information is believed to be accurate but not guaranteed.
Listing is courtesy of: JUDY B CLEAVES PROPERTIES INC (863-299-5878)
Listing Agent: Carol Jean Sheil (863-412-3801)
148 LAKE OTIS RD, WINTER HAVEN, FL 33884
$459,000105 Days on yellowkey MLS ID: L4958667
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2663 Built: 1974Monthly Fee: $100 Tax: $6,141 (2025)Community: LakewoodSingle Family
Taxes:$6,141
Remarks: Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level home offers a perfect blend of modern luxury and comfort. With a spacious layout, a private pool, and an abundance of natural light, this home is designed for both relaxation and entertaining. As you enter, you’ll immediately notice the bright and airy atmosphere created by large windows that allow natural light to flood the home. The home features stunning luxury vinyl plank flooring and a beautiful brick fireplace, adding warmth and character to the space. The kitchen is of good size and boasting sleek countertops, new modern appliances, and ample cabinet space. Enjoy casual meals in the eat-in kitchen or step outside to the screened-in porch, an ideal spot for dining al fresco or simply relaxing while overlooking the expansive backyard and pool. Come add your personal touches and make this house your beautiful home!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Michelle Armbruster (863-521-6879)
1097 SANDPIPER LOOP, WINTER HAVEN, FL 33881
$420,00063 Days on yellowkey MLS ID: L4959736
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1912 Built: 2022Monthly Fee: $63 Tax: $3,339 (2025)Community: Chestnut CreekSingle Family
Taxes:$3,339
Remarks: Welcome to 1097 Sandpiper Loop, a beautifully maintained home situated in an intimate community of fewer than 90 residences. Conveniently positioned just off Country Club Road in Winter Haven, this property offers the best of both worlds—quick access to downtown amenities while enjoying the comfort of spacious quarter-acre lots that provide added breathing room. As you enter, you’re welcomed by attractive luxury vinyl flooring that runs throughout the main living spaces, creating a cohesive and low-maintenance design. The kitchen is thoughtfully designed for both everyday living and entertaining, featuring granite countertops, stainless steel appliances, and a generous walk-in pantry. It flows seamlessly into a flexible dining area that can easily adapt to formal gatherings or casual meals. In addition to the main living areas, the home includes a versatile flex room—perfect for a home office, study, playroom, or additional lounge space. The primary suite offers ample space and comfort, paired with a well-appointed bathroom designed with quality finishes and a relaxing atmosphere. Step outside to enjoy the extended covered and screened patio, providing a peaceful outdoor retreat overlooking a fully enclosed backyard. Numerous upgrades throughout the home enhance both functionality and overall appeal. Don’t miss your chance to own this thoughtfully designed home in a desirable Winter Haven location. Schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
5225 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884
$420,000252 Days on yellowkey MLS ID: P4936039
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2031 Built: 2015Community: Lake Ashton West Ph 01Single Family
Taxes:
Tax Year:
Remarks: HUGE PRICE ADJUSTMENT — MOTIVATED SELLER! Welcome to this beautifully, open-concept Sebastian model FULLY FURNISHED and TURNKEY, allowing you to settle in and start enjoying the Lake Ashton lifestyle from day one. Grand, high ceilings immediately draw your eyes to the serene 17th-hole golf view, offering a peaceful backdrop perfect for relaxed living. The living room is anchored by a stunning wood entertainment center with glass display, complemented by plush leather recliners ideal for unwinding or hosting friends. Recessed lighting, neutral tones, and crown molding create a warm, inviting ambiance throughout the home. This home features tile flooring throughout the main living areas, thoughtfully selected furnishings in every room, and a second bedroom equipped with a medical bed for guests or caregiving needs. The gourmet kitchen includes 42" wood cabinetry with crown molding, granite countertops, a stylish backsplash, pendant lighting, Whirlpool stainless steel appliances, and under- and over-cabinet lighting. A washer and dryer are also included for easy, everyday living. The primary suite offers a peaceful retreat with a walk-in closet, dual granite vanities, and a walk-in shower with a corner seat. Triple sliders open to an extended screened veranda, perfect for morning coffee, evening breezes, or simply enjoying the tranquil golf course setting. The Garage is equipped with storage, a golf cart, a leisure bike, and a garage privacy screen, making it easy to embrace the active lifestyle of Lake Ashton. Just unpack and begin enjoying the community, offering two gated entrances with 24/7 guard service and access to two clubhouses featuring a grand ballroom, movie theater, bowling lanes, and on-site dining at Charm City and Eagle Nest. Stay active with amenities including indoor and outdoor pools, fitness centers, racquetball, tennis, pickleball, bocce, shuffleboard, and more.
Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)
Listing Agent: Candra Alston (407-257-5204)
12 BRIDGEWATER DR, WINTER HAVEN, FL 33884
$440,00065 Days on yellowkey MLS ID: S5144703
0 Days Off yellowkey (back on 3/6/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2369 Built: 1990Community: BridgewaterSingle Family
Remarks: Under contract-accepting backup offers. Welcome home to this fabulous 3 bedroom, 3 bath water front pool home nestled in the desirable Bridgewater community. The home is located on the infamous "WINTER HAVEN CHAIN OF LAKES" on the canal between lake Eloise and the cleanest spring fed lake on the chain, LAKE WINTERSET. BRIDGEWATER IS AN ESTABLISHED COMMUNITY OF 22 CUSTOM BUILT HOMES. With access to a private community boat ramp, and newly renovated COMPOSITE dock for your boating and fishing pleasure. Lake Winterset often offers a SLALOM COURSE for the water skiing enthusiast. This fabulous brick home will have a BRAND NEW REROOF with ARCHITECTURAL SHINGLES, peel and stick UNDERLAYMENT installed over the next two weeks for the new owners peace of mind. The new roof will have a ten year transferable warranty to the new owner. As you enter this amazing home you'll be greeted by the grand foyer with vaulted ceilings, and an amazing view of the wood burning brick fireplace in the sunken great room with wooden floors, BLENDING RETRO CHARM WITH MODERN COZY FUNCTIONALITY. There are two sets of French doors exiting to the outdoor kitchen pool area from the great room with amazing views. As you turn to the right, you step inside the amazing study with wooden floors which can easily be transformed into a formal sitting room. Boasting over 2,369 square foot of living space there is plenty of room in this oversized kitchen and dining area to entertain your guest and sliding doors to exit to the pool area. The custom made plantation shutters in the dining area, convey with the home. The large primary bedroom has its own sliding doors that exit to the fully enclosed screen pool and outdoor kitchen area and TWO LARGE WALK IN CLOSETS. The primary bathroom has dual vanity sinks and a large garden jet tub with separate walk in shower stall. Enjoy cooking and entertaining in your fully screened in lanai with an outdoor kitchen area while taking in the sights and sounds of nature on this freshwater canal, AND CASCADING WATERFALL FROM THE SPA INTO THE HEATED POOL. The community of Bridgewater has its own PRIVATE BOAT RAMP LAUNCH and newly renovated dock for unlimited usage to its residents that wish to boat or fish just a few feet from their front door. The home is equipped with two air condition units one replaced 2 YEARS AGO and the other 5 YEARS AGO. Both front loader, washer and dryer convey inside this large indoor laundry room. The two car garage door was insulated for more energy efficient climate control. The home is located just 2.3 MILES FROM THE GATES OF LEGOLAND and just 2.5 MILES FROM SHOPS RESTARUANTS AND MEDICAL FACILITIES making this location ideal. Schedule your viewing today.
Listing is courtesy of: MAZELG REALTY (863-399-0226)
Listing Agent: Eric Sigismondi, Llc (863-651-9257)
280 LAKE SMART CIR, WINTER HAVEN, FL 33881
$425,00087 Days on yellowkey MLS ID: L4959205
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2497 Built: 2021Community: Lake Smart PointeSingle Family
Remarks: Welcome to your 4 bedroom, 2.5 bathroom 2 story home located conveniently in Winter Haven with easy access to shopping, dining, and major roadways. Arriving at the home, you’ll appreciate the tastefully landscaped yard and screened in entry way. Entering the home, you’ll find LVP flooring throughout the home. The bright and open kitchen features stainless steel appliances, quartz countertops, a large island with sink and upgraded faucet, upgraded overhead lighting, wood cabinets, tile back splash and a closet pantry. There is a dining area adjacent to the kitchen. The living room offers plenty of space for entertaining or relaxing. Stepping through the glass sliding doors, you’ll find a large screened porch, the perfect spot for BBQ’s with friends and family! Upstairs, you’ll find a loft area that would make a great library or TV space. The primary bedroom is spacious and bright and features an en-suite with a dual sink vanity, stand up shower, and huge walk in closet!! The remaining bedrooms provide plenty of space and share the main hall bathroom featuring a large single sink vanity and tub/shower combo. The home also features an alarm system, inside laundry room, half bath downstairs, upgraded stair rail spindle, and a fully fenced in yard. The home offers pedestrian access to Lake Smart and the pier. There is an assumable mortgage at a rate of 5.50%. This home checks all the boxes! Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Casandra Vann (863-546-5446)
1209 SAWGRASS DR, WINTER HAVEN, FL 33884
$439,000105 Days on yellowkey MLS ID: P4937555
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2045 Built: 2017Community: Lake Ashton West Ph Ii SouthSingle Family
Remarks: Your Florida Dream Home Awaits in Lake Ashton, an exclusive gated 55+ community. A golf membership (expires Sept. 30, 2026) for a single golfer will convey. Discover this beautiful 3 bedroom, 2 bathroom Sebastian Floor Plan home with an oversized backyard with pond and trees beyond. This PET FREE home is perfectly positioned; one home removed from a cul-de-sac. With over 2,045 sq. ft. living area, this home offers great curb appeal with a well maintained lawn, gutters, paver driveway & walkway, poured curbing around landscaped areas & separate golf cart garage entry. You'll love the screened entry at the front door with side lights and eyebrow window above. With a spacious open floor plan, this bright and airy home is designed for both comfortable living and seamless entertaining with the kitchen overlooking the living room and dining room areas with tile flooring and trey ceiling. Built in 2017 this desirable home has SS Appliances, Under Cabinet Lighting, Breakfast bar, 42" cabinets, Walk In Pantry and generous Granite counter space in the kitchen, making it a chefs delight. Bedroom 2 & 3 are located to the right of the front door just off of the front entrance of the home. Bedroom 2 with carpet, built in closet and Bay window is on the front of the home. Bedroom 3 with tile plank flooring, built in desk with cabinets above and two side closets could be used as a sitting room, craft room or additional tv room for guests. - You choose. The Guest Bathroom separates BR 2 and BR 3. Guests will love the walk in shower with glass enclosure, comfort height vanity and accent glass block above. A linen closet is in the hallway that separates BR 2 and BR 3. The living room has triple glass sliding doors that open to the covered and screened lanai. You'll love the water and nature views from the LR, Dinette and Primary Suite. This well-maintained home with newly cleaned windows has a central vacuum system, too! The Primary Suite is located on the back of the home directly off the Living Room. The En- Suite offers a large walk in closet, separate water closet with window, His and Her Comfort Height Vanities and Large corner Walk In Shower with tiled corner seat/footrest, accent glass block above and a door separates the Primary Bath and Primary Bedroom. Unwind after a long day of having FUN on the screened, covered Lanai with one acrylic window wall. Place your grill on the paver pad just outside of the lanai and take in the tranquil surroundings of your oversized backyard with seasonal pond and trees beyond. The SOLAR PANELS on this home will provide additional monthly savings to YOU. The washer/dryer in the spacious laundry room will convey with the sale of the home. The laundry room has a wash sink, additional cabinets (upper and lower), a seat so you can put on your shoes with ease and a shoe organizer. The garage floor has an epoxy coating and an automatic screen is on the double car garage. Residents in Lake Ashton enjoy the main clubhouse with outdoor pool, bocce, movie theater, card, craft, billiards, bowling lanes, media room, fitness center and grand ballroom. Residents also enjoy the Health and Fitness Center with indoor pool, indoor basketball, indoor racquetball, card, craft and billiards, pickle ball, tennis courts and MORE. Golf Memberships are optional. 2 18-hole golf courses are located within Lake Ashton. Restaurants, Entertainment, Shopping and Medical Facilities are just a short distance away. You MUST See this home!
Listing Agent: Lori Raath (863-409-6899)
357 RUBY LAKE LOOP, WINTER HAVEN, FL 33884
$415,00045 Days on yellowkey MLS ID: L4960449
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2107 Built: 1998Community: Ruby Lake Ph 01Single Family
Remarks: Welcome to your dream home in the gated community of Ruby Lake! This beautifully designed 3-bedroom, 2-bath Cassidy “Ox” floor plan perfectly balances elegance and everyday comfort. Step inside to discover a spacious layout featuring formal living and dining rooms, along with a generous family room—ideal for both entertaining and relaxed living. The updated kitchen is truly the heart of the home, showcasing sleek quartz countertops, a breakfast bar, closet pantry, and durable tile flooring. Retreat to the impressive primary suite, offering a large 17x15 bedroom, walk-in closet, and a spa-like en suite bath complete with soaking tub, walk-in shower, and dual vanities. Thoughtfully designed, the secondary bedroom and bath are handicap accessible with widened doorways for added ease. Enjoy Florida living year-round on the expansive 10x38 screened lanai—perfect for gatherings or quiet evenings. Additional highlights include an interior laundry room with sink, surround sound throughout, plantation shelving with ambient lighting, ceiling fans, irrigation system with separate meter, and a 2-car garage with a high-profile door. Conveniently located near shopping, dining, medical facilities, schools, and Legoland, with easy access to Tampa and Orlando—this exceptional home truly has it all. Don’t miss your opportunity to make it yours!
Listing Agent: Steve Lockhart (863-289-9801)
404 TALAMONE DR, WINTER HAVEN, FL 33884
$485,000144 Days on yellowkey MLS ID: P4937070
1 Days Off yellowkey (back on 3/16/2026)
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2221 Built: 2001Community: Tuscany At WintersetSingle Family
Remarks: BACK ON MARKET DUE TO BUYERS FAILED FINANCING!! MAGNIFICENT 4BR/3BA POOL HOME!! Located in the gated Winter Haven subdivision of Tuscanny, this exquisitely maintained one story home, with approx. 3,242 sqft including an air conditioned sunroom, has so much to offer; it showcases a full GUEST SUITE and a new roof as of April 2021! Fantastic Features include: crown molding, ceramic tile, laminate flooring in all 4 bedrooms, updated granite countertops, sinks and fixtures, volume ceilings and fresh paint. The Kitchen is a chefs dream!! It has stainless steel appliances with a Subzero fridge, custom maple cabinetry, gas range with a restaurant style warming lamp and commercial vent, accent lighting, and a large walk-in pantry. A spacious family room flows off the kitchen and overlooks the pool, patio, and air conditioned Florida room. The luxurious Master Suite showcases tray ceilings and dual walk-in closets, with a well-appointed en suite Master Bath, including dual vanities, walk-in shower, a jetted tub and a water closet for privacy. The GUEST SUITE has its own private full en suite bathroom. There are 2 additional bedrooms and a guest bathroom, which also connects as a pool bath with outside access. The air conditioned enclosed sunroom is just off the master bedroom, through the French doors, overlooking the pool; perfect to enjoy your morning coffee, and adding great flow to the well thought out floor plan. The pool and deck have been repainted in recent years, and pool AND BUILT IN HOT TUB area have been re-screened. A BBQ patio has been newly added out back for an expansion of the outdoor enjoyment. Also added, a privacy fence tree line and poolside sun shades ensuring separation from rear neighbors. There is an OVERSIZED 2 car side garage, large pavered CIRCULAR DRIVEWAY, attractive mature landscaping, and MORE!!! All this in a beautiful gated community just minutes from LEGOLAND, Disneyworld, and Universal Studios! This well appointed home is PRICED TO SELL. What are you waiting for???! Seller is also the listing agent.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Marissa Taranto (888-883-8509)
305 HERNANDO RD, WINTER HAVEN, FL 33884
$479,000 MLS ID: P4937701
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2569 Built: 1978Community: Valenciawood HillsSingle Family
Remarks: Listing price reduced!!! Enjoy the quaint living in this deed restricted community! Step into this stunning home through a spacious, light-filled foyer and prepare to be impressed by the thoughtfully, well maintained designed layout and exceptional features throughout. This home offers oversized bedrooms and a versatile bonus room—perfect for a game room, home office, or even a private in-law suite. This home has a formal living area, family room and dining area. So many different options for the use of this home. Two of the secondary bedrooms are connected by a convenient Jack-and-Jill bathroom, ideal for family living. The expansive kitchen boasts an abundance of cabinetry and storage, complemented by updated stainless-steel appliances and gleaming granite countertops. The bathrooms have been tastefully updated with granite surfaces and beautifully tiled showers. The master suite is truly unique, featuring a walk-around closet, a vanity area, and direct access to the sparkling pool area. In fact, the pool can be accessed from the master bedroom, family room, pool bath, one of the bedrooms, and the bonus room—making indoor-outdoor living a breeze. Additional highlights include: A Generac whole-home generator with a 120# propane tank and a irrigation system for the beautifully maintained yard, a newer roof (2016) and the pool system was replaced in 2021 and is well maintain as you will see. Located in the quiet, charming neighborhood of Valencia Wood Hills, this home offers the perfect balance of peace and convenience. Ideally situated between Tampa and Orlando, you’re just minutes from shopping, Legoland, and over 100 stunning lakes—perfect for boating, water skiing, and sunset dining. Don't miss the opportunity to make this exceptional home yours! You must see to appreciate!...Schedule your showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Sherry Sapp (863-860-7000)
1531 FUJI CT, WINTER HAVEN, FL 33881
$489,000 MLS ID: P4938096
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 3058 Built: 2023Community: Lake Lucerne IiSingle Family
Remarks: Welcome to this beautifully maintained 4-bedroom, 3-bath home built in 2023 and located in the Lucerne Park area of Winter Haven. This spacious home with over 3,000 square feet of living space with an open floor plan designed for both comfort and functionality. The large kitchen opens to the main living area, creating the perfect space for entertaining and everyday living. The primary suite provides a private retreat with a spacious bathroom and walk-in closet, while additional bedrooms provide plenty of room for family, guests, or a home office. Conveniently located near shopping, dining, schools, and just a short drive to LEGOLAND Florida Resort. Don’t miss the opportunity to own this nearly new home in a growing community.
Listing Agent: Jessica Delgado (407-520-0159)
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