Between $400,000 - $500,000 Winter Haven FL Real Estate, Homes, Condos for Sale

4 Beds ⋅ 4 Baths ⋅ Lakewood Tr 173 SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. Located in the highly sought-after gated community of Lakewood, this beautifully maintained home offers 4 bedrooms and 3.5 bathrooms, set on a lush, manicured lot with mature trees and attractive landscaping. Inside, you’ll find rich wood flooring throughout the spacious living and dining areas, as well as the kitchen and family room—perfect for both everyday living and entertaining. A standout feature is the expansive 480 sq ft detached game room, included in the total living area, complete with a full bathroom and generous closet space—ideal for conversion into a private guest house, in-law suite, or home office. The primary suite boasts a recently renovated en-suite bathroom and direct access to the large screened lanai and pool area, creating a relaxing retreat. Major updates include a roof replacement in 2017. This exceptional property offers space, flexibility, and charm—don’t miss your opportunity to make it yours!

184 Lake Otis Road, Winter Haven

$469,000

4 Beds ⋅ 3 Baths ⋅ Hampton Cove SubDv. ⋅ 33881 Zip Code

Under contract-accepting backup offers. Welcome to this immaculately maintained 4-bedroom, 3-bathroom home with a spacious 3-car garage, perfectly situated in the highly desirable Country Club area of Northeast Winter Haven. Located within a gated community, this home offers both privacy and peace of mind. Backing up to an 11-acre jurisdictional wetland, the property provides complete rear privacy with a beautiful natural landscape—no rear neighbors, just serene views and tranquil surroundings. Inside, you’ll find a thoughtfully designed split floor plan with upgraded flooring, modern cabinetry, and stylish countertops throughout. The layout offers both functionality and comfort, ideal for those who love to entertain. Step outside to your private screened back porch retreat and fully fenced yard—perfect for relaxing evenings or weekend gatherings while enjoying the quiet, natural backdrop. This home truly combines luxury, privacy, and location—don’t miss the opportunity to make it yours.

132 Broad Street, Winter Haven

$430,000

4 Beds ⋅ 2 Baths ⋅ Terranova Ph 02 SubDv. ⋅ 33884 Zip Code

ROOF 2022! Enjoy the HEATED SALTWATER POOL all year in your backyard Oasis. LARGE CORNER LOT (.28 acre). SINGLE STORY HOME. Terranova is a GATED COMMUNITY nestled among the Winter Haven Chain of Lakes. LOW HOA. NO CDD. Screened in patio is great for enjoying the beautiful Florida weather. Fully fenced yard with double door gate so you can pull a small boat inside! SPLIT FLOOR PLAN features the primary bedroom and bathroom on one side of the home and three additional bedrooms and a full bath on the other. High ceilings. BRAND NEW PUBLIX GROCERY STORE less than five minutes away! Walking trail within the community to Chain of Lakes Elementary School. The pool has a child safety fence that can be put up if desired - not photographed. Call to schedule your private showing today.

496 Terranova Street, Winter Haven

$440,000

4 Beds ⋅ 3 Baths ⋅ Lake Lucerne Ii SubDv. ⋅ 33881 Zip Code

Discover this stunning 2023-built home in the growing Lucerne Park area of Winter Haven, offering the perfect blend of space, comfort, and modern design. Situated on an oversized lot, this 4-bedroom, 3-bath home with a 3-car garage features over 3,000 square feet of living space with an open and functional floor plan ideal for entertaining and everyday living. The large kitchen overlooks the main living area, creating a bright and welcoming space for gatherings. The spacious primary suite features a walk-in closet and private bathroom, while the additional bedrooms provides flexibility for family, guests, or a home office. Enjoy the oversized backyard with plenty of room to relax, entertain, or create your dream outdoor oasis. Conveniently located near shopping, dining, schools, and just minutes from LEGOLAND Florida Resort, this move-in ready home is a fantastic opportunity in one of Winter Haven’s growing communities.Seller is offering a contribution toward the buyer’s closing costs, helping reduce out-of-pocket expenses at closing.

1531 Fuji Court, Winter Haven

$405,900

4 Beds ⋅ 3 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code

Seller is willing to offer funds towards Buyer's Closing Costs. Welcome to 4020 Carteret Dr in Winter Haven, a beautifully updated 4-bedroom, 3-bath home located in a desirable 55+ lakefront community with a 3-car garage offering comfort, convenience, and low-maintenance living in the heart of Central Florida. This thoughtfully designed home features stunning lake views, hardwood flooring, an updated kitchen with modern finishes, and stylish upgrades throughout. The spacious layout includes a mother-in-law suite, perfect for visiting family, guests, or additional privacy. Residents enjoy direct water access and a private community boat ramp, providing easy access to Winter Haven’s renowned Chain of Lakes, ideal for boating, fishing, and enjoying Florida’s outdoor lifestyle. The community also offers boat and water toy storage for a small fee, making it convenient to keep your boat or jet skis nearby and ready to use. One of the standout features of this home is the maintenance-free lifestyle. The HOA covers Cable, Internet, Exterior Home Maintenance including landscaping, mulch, and exterior painting, and More, allowing homeowners to enjoy their property without the typical upkeep responsibilities. Located just minutes from Cypress Gardens Boulevard, this home offers quick access to shopping, restaurants, grocery stores, golf courses, parks, and medical facilities. Residents are also close to LEGOLAND Florida Resort, and major roadways including US-27 and the Polk Parkway, making travel to Lakeland, Orlando, and Tampa convenient. If you’re searching for a Lake view home in Winter Haven, a low-maintenance home in a 55+ community, or a property with Ruby Lake access, 4020 Carteret Dr offers the perfect combination of location, lifestyle, and modern comfort in one of Polk County’s most established lake communities. Schedule a showing today!

4020 Carteret Drive, Winter Haven

$414,635

6 Beds ⋅ 4 Baths ⋅ Harbor At Lake Henry SubDv. ⋅ 33881 Zip Code

Pre-Construction. To be built. New construction home with 3162 square feet two-story including 6 bedrooms, 3.5 baths, plus loft and bonus room and an open living area. Enjoy an open kitchen with shaker-style cabinets, granite countertops, Samsung stainless steel appliances, pantry, and a spacious breakfast bar, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. Plus, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. ***Please note - Virtual Tour/Photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey!

439 Ituna Circle, Winter Haven

$410,000

3 Beds ⋅ 2 Baths ⋅ Chestnut Creek SubDv. ⋅ 33881 Zip Code

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.

1097 Sandpiper Loop, Winter Haven

$459,000

6 Beds ⋅ 5 Baths ⋅ Lake Shipp Or Porters Add SubDv. ⋅ 33880 Zip Code

Virtually Staged. Fully occupied 5-unit multifamily investment property located minutes from Downtown Winter Haven in a high-demand rental market. Zoned multifamily and currently producing immediate cash flow with all units leased. Strong location near major thoroughfares, retail, and ongoing residential development, including a planned townhome project that is expected to support future rental demand. Opportunity exists for additional income growth through rent optimization. Situated in one of Central Florida's fastest-growing submarkets, this stabilized asset offers current income, long-term appreciation potential, and portfolio expansion opportunities. Contact for rent roll and financial information.

1339 7th Street Sw, Winter Haven

$450,000

4 Beds ⋅ 2 Baths ⋅ Lake Thomas Woods Eight Add SubDv. ⋅ 33880 Zip Code

RUDUCED PRICE! MOTIVATED SELLERS Charming 4-Bedroom Lakefront Home on Lake Thomas – No HOA Discover the perfect blend of comfortable family living and relaxed lakefront lifestyle in this beautiful 4-bedroom, 2-bath home on Lake Thomas. Offering a spacious layout, generous outdoor space, and scenic water access, this property delivers both everyday functionality and waterfront charm. Step inside to find tile flooring throughout the main living areas and an open-concept design that seamlessly connects the living and dining spaces — ideal for family gatherings and entertaining guests. Ceiling fans throughout the home enhance comfort year-round. Outdoors, enjoy an oversized, level backyard that’s fully fenced — perfect for pets, outdoor dining, gardening, or play. Whether you're relaxing by the water or hosting weekend barbecues, this home offers space and flexibility to fit your lifestyle. Located in Winter Haven, you’ll appreciate convenient access to local amenities, shopping, dining, and recreational opportunities — all without the burden of HOA restrictions. Lake living, space to grow, and freedom to enjoy — this one has it all.

183 Lake Thomas, Winter Haven

$485,900

5 Beds ⋅ 3 Baths ⋅ Pinnacle Point SubDv. ⋅ 33880 Zip Code

Neighboring home just sold and here is one more Catalina model left. This home is a steal and OWNERS ARE MOTIVATED!!! The immaculately kept 2023 home offers the same floor plan, Upgraded Flooring, Caged Saltwater Pool with a Safety Alarm System, Spacious Gazebo, and many more outstanding features. Located in Winter Haven near the scenic Chain of Lakes, this 5 Bedroom 3 Bathroom home with two Flex Rooms is move in ready and close to everything loved like easy commuting, Grocery Stores, Shopping, Dining, Boat Ramps, Scenic Walking Trails, Theme Parks and not too far from Beaches and Cruise Ports! The Outside Oasis offers a Relaxing Retreat for Outdoor Dining, Lounging, or Entertaining while overlooking this communities Beautiful Pond. Unique Bonus Room with a Sound Proofing wall, ideal for Recording Studios, Podcasters, Musicians, Content Creators or any Work from home professionals needing their quiet space. This home shows like new with Fresh Interior Paint, New Luxury Laminate Flooring, Carrara Porcelain Tile for a sleek modern finish. You will appreciate the Bright open concept living area, Spacious Kitchen, and Water Softener for a supreme refreshing quench. With its flexible floor plan, this home can easily accommodates Large Families, Multi Generational living or hosting guests comfortably. It's is a must see in a highly sought after community!

1491 Axel Circle, Winter Haven

$422,948

5 Beds ⋅ 4 Baths ⋅ Seasons At Annabelle Estates SubDv. ⋅ 33884 Zip Code

Under Construction. The main floor of the inviting Ammolite plan offers a private study and versatile flex space, which can be optioned as an additional bedroom and bathroom or a guest suite, complete with living room. You’ll also appreciate a convenient powder room; a nook; a great room and a well-appointed kitchen with a center island, a large pantry, and optional additional cabinets. Upstairs, discover an airy loft, a convenient laundry, three secondary bedrooms, and a lavish primary suite boasting an expansive walk-in closet and a private bath. This plan also features a patio and a 2-car garage. SAMPLE PHOTOS. Actual homes as constructed may not contain the features and layouts depicted and may vary from image(s).*Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

5122 Kinsley Drive, Winter Haven

$425,000

6 Beds ⋅ 5 Baths ⋅ Hart Lake Cove Ph 02 SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. COMPLETE REMODELING * PRIME LOCATION * HOUSE & INVESTMENT * NEW ROOF 2026 Complete remodeling house6/5 near 4,000 square feet of living area. Short distance from parks as Legoland, restaurants, malls. Great location between Tampa and Orlando. Builders don't build this king of big houses anymore. Brand new fence, new floors, walls and update bathrooms inside, owner invested more than $50,000 on new updates. Price is reduced for a quick sale. Today construction cost is $200 square feet. Get this great deal for a fraction of the original price. All concrete block construction.

461 Fish Hawk Drive, Winter Haven

$451,000

4 Beds ⋅ 3 Baths ⋅ Lakewood SubDv. ⋅ 33884 Zip Code

SELLER VERY MOTIVATED! 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!

148 Lake Otis Road, Winter Haven

$452,000

3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph Ii North SubDv. ⋅ 33884 Zip Code

Welcome to this beautifully upgraded 3-bedroom, 2-bath home offering 2,045 square feet of refined living space in the highly desirable Lake Ashton 55+ golf community—where luxury meets an active, resort-style lifestyle. This thoughtfully designed home features top-notch upgrades throughout, including an additional sliding glass door leading to the back patio, flooding the living space with natural light and creating a seamless indoor-outdoor living experience. The spacious kitchen is a standout, boasting abundant cabinet storage with extended cabinetry along the back wall, perfect for entertaining, organization, and everyday convenience. Smart hybrid water heater and water softener system as well The open and inviting floor plan provides generous living and dining areas, while the private primary suite offers comfort and tranquility. Two additional bedrooms are ideal for guests, hobbies, or a home office. Both bathrooms are well-appointed, and the home’s layout is designed for easy living. Located within Lake Ashton, residents enjoy world-class amenities including championship golf courses, clubhouses, fitness centers, pools, tennis and pickleball courts, planned activities, and a vibrant social calendar. Experience the best of Florida living in this exceptional home—schedule your private showing today and discover everything Lake Ashton has to offer.

6308 Pinehurst Loop, Winter Haven

$439,000

4 Beds ⋅ 3 Baths ⋅ Overlook Ests Ph 3 SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. Beautiful 4 bedroom, 2 1/2-bathroom, pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.

240 Santa Rosa Drive, Winter Haven

$415,000

4 Beds ⋅ 3 Baths ⋅ Gates Of Lake Region SubDv. ⋅ 33881 Zip Code

Impressive custom home in the quaint gated community of The Gates of Lake Region in Winter Haven FL. This beautifully maintained neighborhood is known for its picturesque brick-walled entrance, lush mature landscaping, tranquil ponds with fountains, and pride of ownership throughout. Unlike larger developments, The Gates of Lake Region offers a warm, neighborly atmosphere where residents enjoy quiet streets, manicured lawns, quality-built homes, and a true sense of community. This spacious 2,500-square-foot residence was originally constructed as a builder's model home and showcases numerous upgrades and architectural details throughout. Built with high-efficiency Ytong concrete block construction, the home offers superior sound reduction, enhanced structural performance, and meaningful energy savings. The elegant floor plan features 4 spacious bedrooms (one currently utilized as an office), 2 full bathrooms, and 1 half bath. Refined interior finishes include crown molding, oversized custom doors, handcrafted double entry doors, custom cabinetry, ceiling fans, a jetted tub in the primary suite, and a generously sized laundry room. Mature landscaping and a covered front entry create an inviting first impression. Inside, the foyer opens to formal living and dining areas accented by soaring ceilings and detailed trim work, providing an elegant setting for both everyday living and entertaining. The well-appointed kitchen offers abundant cabinetry, solid-surface countertops, a closet pantry, and a bright breakfast nook overlooking the screened lanai and private brick-walled backyard. The comfortable family room is centered around a granite-faced gas fireplace that adds warmth and character. A desirable split-bedroom layout provides privacy for the primary suite, which features a spacious walk-in closet, soaking tub, and tiled walk-in shower. The guest wing includes two additional bedrooms with generous closet space and convenient access to the guest bath. Outdoor living is equally inviting with a large screened lanai, mature tropical landscaping, and a private brick-walled backyard designed for relaxation and enjoyment. Additional features include an oversized two-car garage, natural gas water heater, irrigation system, and an efficient interior laundry room with additional storage. Residents of The Gates of Lake Region enjoy a peaceful setting surrounded by scenic ponds, decorative fountains, and beautifully maintained common areas, all while being just minutes from the Winter Haven Chain of Lakes, several golf courses, the Country Club of Winter Haven, medical facilities, shopping, dining, and Downtown Winter Haven. A new Publix is also planned nearby for added convenience. Orlando, Tampa, international airports, and both Florida coasts are all within easy driving distance. If you're searching for a community that combines timeless charm, quality homes, beautiful surroundings, and a genuine neighborhood feel, The Gates of Lake Region is a place you'll be proud to call home.

108 Lake Region Boulevard N, Winter Haven

$435,000

3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code

Golf Course • 3-Car Garage • Private Office • Move-In Ready • Premier 55+ Resort Lifestyle Imagine waking each morning to sweeping golf course views, enjoying coffee on your screened lanai as the sun rises over the fairway, and spending your days surrounded by resort-style amenities designed for the active lifestyle you've earned. Welcome to Lake Ashton, one of Central Florida's premier gated 55+ communities, where championship golf, pickleball, tennis, fitness centers, lakeside recreation, fine dining, and an endless calendar of social activities create an extraordinary way of life. Perfectly positioned on the golf course, this beautifully maintained move-in ready residence offers 2,354 square feet of thoughtfully designed living space with 3 bedrooms, 2 bathrooms, a dedicated office/den, and an oversized 3-car garage with plenty of room for vehicles, a golf cart, hobbies, or additional storage. Inside, you'll discover an elegant blend of comfort and sophistication. A welcoming foyer opens to spacious living and dining areas accented by crown molding, architectural columns, and abundant natural light. The well-appointed kitchen features granite countertops, quality cabinetry, stainless steel appliances, generous workspace, and a breakfast bar that flows seamlessly into the family room—ideal for entertaining or enjoying quiet evenings at home. The private owner's suite serves as a relaxing retreat with tranquil golf course views, dual walk-in closets, and a spacious ensuite bath complete with dual vanities, a soaking tub, and a separate walk-in shower. Two additional guest bedrooms provide comfortable accommodations for visiting family and friends, while the flexible office offers the perfect space for remote work, reading, crafts, or hobbies. Step outside to the expansive screened lanai where panoramic golf course vistas create the perfect backdrop for morning coffee, afternoon gatherings, or peaceful evenings watching Florida's spectacular sunsets. Beyond your front door, Lake Ashton offers an unmatched lifestyle with two private clubhouses, championship golf courses, indoor and outdoor pools, fitness centers, bowling lanes, movie theater, tennis, pickleball, bocce, lakeside activities, on-site dining, and countless clubs and events that make every day feel like a vacation. If you've been searching for more than just a home—if you're looking for a vibrant community where neighbors become friends and every day offers something new—this exceptional golf course residence delivers the Florida lifestyle you've been dreaming about. Schedule your private showing today and discover why so many are proud to call Lake Ashton home.

4048 Phoenician Way, Winter Haven

$445,000

3 Beds ⋅ 2 Baths ⋅ Island Lakes SubDv. ⋅ 33881 Zip Code

Priced to sell!! Bring them an offer!! Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. Gorgeous real hardwood floors, stand up tub for the later years, huge shed and a low HOA fee. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.

3971 Island Lakes Drive, Winter Haven

$450,000

Bryson R H Sub SubDv. ⋅ 33880 Zip Code

If you’ve been looking for a clean, standalone commercial building in a prime, high-visibility location, this is it. Located on 1st Street South, surrounded by busy auto dealerships and professional offices, and just minutes from downtown Winter Haven, this freestanding building offers excellent exposure with steady drive-by traffic throughout the day. The property features ample paved parking, including front and side spaces, and sits on a corner with easy access and visibility from multiple directions. Inside, you’ll find a bright, open layout with flexible rooms that can be adapted for many types of businesses — salon, boutique, medical office, professional services, or even a small café or studio. The building features a welcoming front entry, updated lighting, two restrooms, and central air conditioning units. Winter Haven continues to grow rapidly, attracting both residents and investors due to its central location in Polk County and proximity to Lakeland, Orlando, and Tampa. This property gives you a chance to own a piece of that growth in one of the most active corridors in town. Highlights: freestanding commercial building with great curb appeal, Plenty of on-site parking.High-traffic corridor near car dealerships and retail centers. Ideal for office, salon, or professional use Easy access to U.S. 17 and Cypress Gardens Blvd.

1610 1st Street S, Winter Haven

$400,000

4 Beds ⋅ 2 Baths ⋅ Gates Of Lake Region SubDv. ⋅ 33881 Zip Code

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, jetted tub, separate shower and a water closet! Bedroom #4 is currently used as a home office. The floor plan allows creativity of 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 is conveniently located within 0.8 mile with additional stores and a bank currently under construction! 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.

126 Lake Region Circle, Winter Haven

$430,000

5 Beds ⋅ 5 Baths ⋅ Lake Add SubDv. ⋅ 33880 Zip Code

Under contract-accepting backup offers. Great investment opportunity! Tenant-occupied property in a central location with strong rental demand. Short sale subject to lender approval. Sold as-is, no repairs. Do not disturb tenants. No seller/creative financing.

724 W Central Avenue, Winter Haven

$500,000

5 Beds ⋅ 3 Baths ⋅ Southeast Terrace SubDv. ⋅ 33880 Zip Code

Fully Renovated! Discover the perfect blend of modern upgrades and timeless charm in this beautifully updated 5-bedroom, 3-bathroom home. Featuring a brand-new kitchen, updated living spaces, new flooring throughout, and completely renovated bathrooms, this property is truly move-in ready. Recent upgrades include a new roof (2024), new electrical panel, new water heater, fresh interior and exterior paint, and all-new lighting and ceiling fans. The kitchen is a standout, showcasing quartz countertops, new cabinetry, stainless steel appliances, and modern finishes. Enjoy the warmth of a cozy wood-burning fireplace or step outside to your private oasis with a resurfaced pool and a spacious, fully fenced backyard—perfect for entertaining or relaxing. Located between Orlando and Tampa with no HOA or CDD, this home offers flexibility, freedom, and excellent investment potential. Conveniently close to major highways, theme parks, shopping, and dining. Short-term rentals are allowed, making this a great opportunity for both homeowners and investors.

1818 6th Street Se, Winter Haven

$457,465

Daniels Sub SubDv. ⋅ 33880 Zip Code

AGGRESSIVELY PRICED PORTFOLIO SALE—MUST BE SOLD TOGETHER WITH 524 1ST ST S, WINTER HAVEN, FL 33880. This 2,300± SF commercial building is part of a two-property offering with a combined price of $720,000. The adjacent property at 524 1st St S includes an additional 1,320± SF office/medical-style building. The properties will not be sold separately. Located in a visible Winter Haven commercial corridor, this building offers a flexible retail/flex-style layout with open work or display areas, storage, two restrooms, ramped access, central air conditioning, and on-site parking. Zoned C-3, the property may support a variety of retail, office, professional, wellness, service, and specialty commercial uses, subject to buyer verification and municipal approval. The health food store business may be available through a separate transaction. Inventory, refrigeration, shelving, racking, and trade fixtures are not included in the real estate sale unless separately negotiated. Buyer must independently verify square footage, zoning, permitted uses, condition, accessibility, and all other property information.

632 1st Street S, Winter Haven

$495,000

33884 Zip Code

This property is located on Pollard Road, which has just been repaved. With the new easement, acquired by the City of Winter Haven, street lights have been added and also City water and City sewer is available. And best of all there is NO HOA. This property is in a rural setting, with the occasional train passing by, yet, less than 5 miles from Publix or the local theme park. Currently, this property is in the county of Polk, but surrounded by the City of Winter Haven. This property was once a grove and as indicated by the FEMA flood plane map is high and dry with good drainage.

Pollard Road, Winter Haven

Browse All Winter Haven FL Between $400K - $500K Properties for Sale

Between $400K - $500K Winter Haven Real Estate