Winter Haven Real Estate

Welcome to Winter Haven, Florida, where stunning real estate opportunities await! Located in Polk County, Winter Haven is a vibrant city known for its beautiful lakes, lush landscapes, and abundant recreational activities. This idyllic locale offers a wide range of real estate options to suit diverse preferences.

Prospective buyers can discover an array of properties, from cozy single-family homes in friendly neighborhoods to luxurious waterfront estates overlooking the serene lakes. With its year-round mild climate and proximity to major attractions, Winter Haven presents an enticing living environment.

Moreover, Winter Haven enjoys easy access to neighboring towns, further enhancing its appeal. Just a short drive away, you'll find the charming communities of Auburndale, Lake Alfred, and Haines City, each offering their own unique character and amenities.

Whether you're seeking a peaceful retreat, a family-friendly community, or an active lifestyle with water sports and golfing, Winter Haven and its neighboring towns provide an abundance of options. Embrace the Florida dream and explore the fantastic real estate opportunities available in Winter Haven today!

Latest Winter Haven Real Estate For Sale

$260,000
3 Beds ⋅ 2 Baths ⋅ L4964916 MLS
Welcome to this beautifully updated 3-bedroom, 2-bath home in Winter Haven! The home offers a versatile in-law suite layout with two living areas and private spaces on each side of the home, connected by a brand-new kitchen featuring new cabinets, quartz countertops, and new appliances. The property also features fresh interior and exterior paint, with most of the flooring updated throughout the home, along with a completely remodeled bathroom. Enjoy the added benefit of paid-off solar panels with no solar loan to assume. The spacious, fully fenced backyard offers plenty of room for entertaining, relaxing, gardening, or outdoor activities. A large workshop/storage area can also be used as a 2-car garage, plus there is a carport in the rear for additional parking. With three separate entrances, this home offers exceptional flexibility for extended family, guests, or a variety of living arrangements. Don't miss this opportunity to own a spacious home with numerous updates and unique features—schedule your showing today!

2336 Avenue E Nw, Winter Haven

Courtesy of LA ROSA REALTY PRESTIGE

$338,000
4 Beds ⋅ 2 Baths ⋅ S5157377 MLS
A fantastic opportunity for investors or future homeowners! This beautiful corner-lot home features 4 bedrooms and 2 bathrooms, offering comfort, space, and excellent income potential. It boasts a beautiful, spacious kitchen. The open-concept layout seamlessly connects the living and dining areas, creating the ideal space for entertaining guests or enjoying everyday family life. Sliding glass doors open onto a large backyard—perfect for outdoor activities, gatherings, or simply relaxing. Additional features include a two-car garage, a fully equipped laundry room, and a well-designed floor plan that prioritizes functionality and comfort. Located in the desirable Lake Lucerne community, residents enjoy excellent amenities such as a clubhouse, swimming pools, a playground, and walking paths. The home is close to shops, restaurants, and major roads—including easy access to US-27—making for a convenient commute to Winter Haven, Davenport, and Orlando attractions. Don't miss out on this incredible opportunity!

604 Sarner Pass Way, Winter Haven

Courtesy of LPT REALTY, LLC

$320,000
3 Beds ⋅ 2 Baths ⋅ TB8548042 MLS
Discover the opportunity to own a home in a convenient Central Florida location, surrounded by attractions, recreation, shopping, dining, and everyday conveniences. Enjoy easy access to LEGOLAND® Florida Resort, approximately 25 minutes away, as well as LEGOLAND Water Park and PEPPA PIG Theme Park. Winter Haven is also known for its beautiful Chain of Lakes, offering opportunities for boating, fishing, water activities, and enjoying Florida's outdoors. The area provides convenient access to local parks, restaurants, shopping, entertainment, and downtown Winter Haven. Its Central Florida location also makes it an excellent base for enjoying many of the region's popular attractions while maintaining a more relaxed residential lifestyle. Whether you're looking for a primary residence, a second home, a vacation property, or an investment opportunity, this property offers the chance to enjoy the best of Winter Haven and Central Florida living. Schedule your private showing today!

4629 Palmetto Drive, Winter Haven

Courtesy of MIRANDA LANDA REALTY GROUP LLC

$275,000
3 Beds ⋅ 2 Baths ⋅ TB8547534 MLS
3BR/2BA Beauty Near Downtown Winter Haven — Fully Updated Kitchen! Move right into this beautifully updated 3-bedroom, 2-bathroom home just minutes from downtown Winter Haven. The kitchen has been completely renovated with brand-new cabinetry, a stylish island, and gleaming granite countertops — a true showstopper for anyone who loves to cook or entertain. Ceramic tile flooring flows throughout the entire home for a clean, cohesive, low-maintenance feel. Enjoy an unbeatable location within walking distance of both Lake Shipp and Lake Howard — perfect for morning walks, fishing, or simply soaking in that classic Central Florida lake life. Downtown Winter Haven's shops, restaurants, and community events are just a short drive away. This home comes move-in ready with the refrigerator, stove, microwave, dishwasher, washer, and dryer all included. Major systems have been well maintained. No HOA means no extra fees and no added restrictions. Homes like this in this location don't sit on the market long — schedule your showing today!

1306 15th Street Sw, Winter Haven

Courtesy of MARK SPAIN REAL ESTATE

$215,000
2 Beds ⋅ 2 Baths ⋅ O6441156 MLS
Welcome to 6364 Lolly Bay Loop NE, a beautifully updated Winter Haven home offering comfort, value, and a convenient Central Florida lifestyle. This property features a **2023 roof, remodeled bathrooms, and new flooring**, giving buyers important major updates and a fresh, move-in-ready feel. Located in a peaceful residential setting, this home offers the opportunity to enjoy the relaxed Winter Haven lifestyle while remaining within convenient driving distance of Orlando and other Central Florida destinations. With access to major highways, nearby shopping, dining, outdoor recreation, and Winter Haven’s many lakes, this location offers the best of both convenience and tranquility. Whether you're looking for a primary residence, a place to settle down, or a home that offers more value for your money, this property is a great opportunity to make Central Florida living your own. Schedule your private showing today and come see all that this home has to offer!

6364 Lolly Bay Loop Ne, Winter Haven

Courtesy of EXP REALTY LLC

$249,900
2 Beds ⋅ 2 Baths ⋅ P4939773 MLS
BEAUTIFUL VILLA READY TO MOVE IN! A brand-new HVAC system (June 2026), along with new insulation throughout the attic. Features include cathedral ceilings, elegant detailed baseboard trim with decorative corner blocks throughout, new flooring, plantation shutters on the windows, and three sets of French doors. The upgraded kitchen features stainless steel appliances, double ovens, and a built-in pantry with pull-out shelves. A utility closet provides additional storage, and the interior laundry room includes a full-size washer and dryer. The primary bathroom features dual showers and two vanities with wood cabinetry, while the second bathroom includes a jetted bathtub and wood cabinet vanity. Golf course frontage and two outdoor patio areas, with one overlooking the 8th fairway, plus a second patio with concrete privacy walls. Cypresswood Country Club community offers golf, a Jr. Olympic-size pool, tennis courts, a restaurant and bar, social events, live music three nights a week, and lush, well-maintained surroundings. Come take a look at this one!

2801 Wingfoot Court, Winter Haven

Courtesy of VILLAGE REALTY OF WINTER HAVEN

$239,000
3 Beds ⋅ 1 Baths ⋅ P4939828 MLS
AFFORDABLE & REFRESHED 3 BEDROOM CBS HOME ON LARGE LOT AND NO HOA!!! Centrally located in Winter Haven, the home is at the end of a dead-end street for low traffic. Features include tile flooring throughout, kitchen has wood cabinets, granite countertops and all appliances. You'll enjoy the large, fenced back yard, one-car garage with extra room for storage. Call today to see!

707 Dolly Ben Court, Winter Haven

Courtesy of THE K TEAM REAL ESTATE SERVICES LLC

$289,000
3 Beds ⋅ 2 Baths ⋅ TB8547254 MLS
Welcome home to this beautifully refreshed 3-bedroom, 2-bathroom home offering a comfortable layout, fresh updates, and an expansive backyard with plenty of possibilities. Step inside to discover all-new flooring and fresh interior paint, creating a bright, clean, and inviting atmosphere throughout the home. The spacious living areas provide a versatile setting for both everyday living and entertaining, with plenty of natural light adding to the welcoming feel. The well-designed floor plan offers three comfortable bedrooms and two full bathrooms, providing plenty of space for a variety of needs. The attached two-car garage adds valuable parking, storage, and everyday convenience. Outside, the sprawling backyard is one of the home's standout features, offering abundant space to entertain, garden, enjoy outdoor activities, or create your own private retreat. Whether you envision a large outdoor gathering area, garden space, play area, or simply room to relax and enjoy the outdoors, the possibilities are plentiful. With fresh interior updates, a functional layout, generous living space, an attached two-car garage, and an expansive backyard, this home is ready for its next chapter. Come see all that this refreshed home has to offer and schedule your showing today!

212 Majestic Gardens Lane, Winter Haven

Courtesy of EXP REALTY LLC

$259,000
4 Beds ⋅ 2 Baths ⋅ P4939825 MLS
4 BEDROOM, 2 BATH NEWER HOME WITH AFFORDABLE HOA, NO CDD AND PRICED TO SELL! Welcome to this clean, well-kept 2020 four-bedroom, two-bath home across from Lake Lucerne in Winter Haven. A brick-paver driveway leads to a two-car garage and a bright, open floor plan. The kitchen features a large island, abundant cabinetry, and all appliances included. Living and dining areas flow together for easy everyday living. The home has no carpeting only easy to care for ceramic tile and luxury vinyl flooring and a Split-bedroom layout that places three bedrooms on one side and a spacious primary suite with ensuite bath and walk-in closet on the other. HOA is only $360 per year with NO CDD. Move-in ready in a convenient neighborhood with NO REAR NEIGHBOR, close to town, around the corner from Willowbrook golf course, shopping, medical and local eateries.

1333 Lucerne Loop Road Ne, Winter Haven

Courtesy of BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY

$765,000
3 Beds ⋅ 2 Baths ⋅ O6441050 MLS
Virtually Staged. Welcome to 3831 Gaines Dr, where beautifully updated interiors, exceptional outdoor living, and the best of the Winter Haven lifestyle come together. Situated on an impressive half-acre-plus homesite in the established Gaines Cove area, this immaculate 3-bedroom plus dedicated office home offers the space, privacy, and character that can be difficult to find. The location is a standout. Enjoy being just minutes from the Winter Haven Chain of Lakes, with multiple nearby options for boat ramps and lake access, making it easy to spend your days boating, fishing, skiing, or exploring Winter Haven’s interconnected lakes. LEGOLAND Florida Resort is also just minutes away, along with shopping, dining, and the everyday conveniences of the Cypress Gardens area. Inside, an inviting open floor plan welcomes you with spacious living areas designed for both everyday comfort and entertaining. Architectural details, abundant natural light, plantation shutters, and a fireplace with built-ins add warmth and character throughout. The beautifully updated kitchen features brand-new appliances and flows seamlessly into the main living area, while updated bathrooms and thoughtful improvements throughout create a polished, move-in-ready feel. A dedicated office with French doors provides the perfect space for working from home, studying, or additional flex space. The upgrades go well beyond what you immediately see. The home features a Kinetico water filtration system, allergen air filtration system, and a Tesla charging station, adding modern convenience and functionality to an already impressive property. Step outside and discover what truly sets this home apart. The expansive screened outdoor living area creates your own private Florida backyard retreat, centered around a heated saltwater pool with plenty of space for relaxing and entertaining. The substantial covered lanai features an impressive outdoor kitchen with built-in grill, vent hood, sink, and refrigeration, complemented by generous outdoor dining and seating areas. Remote-controlled power sun shades on the rear lanai provide added shade, privacy, and comfort at the touch of a button, making this incredible space even more enjoyable throughout the day. And unlike many pool homes, the backyard doesn't end at the screened enclosure. Beyond the pool is an expansive fenced yard with abundant usable green space, mature trees, and beautifully maintained landscaping. The combination of a large homesite, resort-style pool area, covered outdoor living, and substantial backyard creates a wonderful sense of openness and privacy. Curb appeal is equally impressive, with a large paver driveway, expansive front lawn, mature landscaping, and welcoming covered front porch creating a memorable first impression. Spend the morning boating on the Chain of Lakes, the afternoon relaxing in your heated saltwater pool, cook dinner in your outdoor kitchen, and finish the evening unwinding on the lanai. With LEGOLAND just minutes away and shopping, dining, recreation, and multiple lake-access options nearby, 3831 Gaines Dr offers more than a beautifully updated home—it offers the Winter Haven lifestyle.

3831 Gaines Drive, Winter Haven

Courtesy of COLDWELL BANKER REALTY

$323,990
5 Beds ⋅ 3 Baths ⋅ O6441023 MLS
Under Construction. The first floor of the stunning Edison two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

6260 Botticella Boulevard, Winter Haven

Courtesy of LENNAR REALTY

$339,000
4 Beds ⋅ 2 Baths ⋅ S5157350 MLS
Beautiful home featuring 4 spacious bedrooms and 2 bathrooms. The fully equipped kitchen boasts beautiful wood cabinetry and granite countertops. Sliding glass doors lead to a covered patio and a private, grassy backyard—perfect for relaxing and enjoying the Florida outdoor lifestyle. The home includes a 2-car garage and a fully equipped laundry room for added convenience. Situated in a desirable community, this property offers comfort, practicality, and excellent investment potential. It is conveniently located near LEGOLAND, Chain of Lakes Park, downtown Winter Haven, shopping centers, restaurants, grocery stores, and medical facilities, with easy access to Highway 27. Winter Haven is also known for its beautiful Chain of Lakes, offering opportunities for boating, fishing, and outdoor recreation. The property is currently leased through November 2026 at $2,150 monthly. A fantastic opportunity for both investors and future homeowners.

507 Short Lane, Winter Haven

Courtesy of LPT REALTY, LLC

$299,000
4 Beds ⋅ 2 Baths ⋅ TB8547660 MLS
Welcome home! This beautiful property features a comfortable and functional layout, perfect for everyday living and entertaining. Enjoy spacious living areas, a well-appointed kitchen, and inviting bedrooms with plenty of room to relax. Step outside to the fully fenced backyard, providing added privacy and plenty of space for outdoor activities, pets, or weekend gatherings. The covered lanai is the perfect place to enjoy your morning coffee, unwind after a long day, or simply take in Florida’s beautiful weather year-round. Conveniently located near shopping, dining, schools, and major roadways, this home combines comfort, space, and convenience. Schedule your private showing today and come see everything this home has!

624 Sarner Pass Way, Winter Haven

Courtesy of THE ELITE REALTY EXPERIENCE

$345,690
4 Beds ⋅ 2 Baths ⋅ O6438380 MLS ⋅ Na BLDG.
Beautiful Single Level, 2 Car Garage Home with Open Concept Living and 4 Bedrooms! The Baker plan is in Farmhouse exterior design. Adjacent the foyer you'll find 3 secondary bedrooms and a full bathroom. The well-appointed island kitchen overlooks the spacious family room and adjoining cafe with access to the covered lanai. The primary suite boasts an en suite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet.

815 Andrew Street, Winter Haven

Courtesy of DRB GROUP REALTY, LLC

$549,999
3 Beds ⋅ 3 Baths ⋅ P4939770 MLS
*GOLF COURSE and WATER VIEWS*** Located behind the secure gates of the coveted 55 + community of Lake Ashton, the views from the covered and screened lanai are superb! Built in 2019, this home offers TWO SUITES, ONE GUEST BEDROOM and THREE BATHS. This split floor plan home offers great curb appeal with a FRESH NEW EXTERIOR COAT OF PAINT, Paver Driveway and Well Maintained Landscape. The lawn is "watered" by an irrigation system. As you enter thru the double glass doors of this home you are greeted by a large open floor plan offering expansive views of the golf course and lake beyond. The views from this coveted lot location are spectacular so make sure you bring your binoculars! The living room, formal dining area and kitchen flow seamlessly together in this modified ASHTON Floor plan home, making entertaining easy and fun! The spacious Living Room has a tray ceiling, floor outlets, ceiling fan and triple sliders that stack and open to the covered and screened lanai. A formal dining area is located to the left of the front entry and the arched double windows add a touch of class! The Kitchen features 42" wood cabinetry, breakfast bar, pendant lighting, granite countertops, SS appliances (microwave replaced Sept. 2026) and ample counter top space for food prep and food display. The Dinette area is conveniently located off of the kitchen and the double windows provide an abundance of natural light into the home. Double sliders provide access to the lanai from the dinette area. The spacious and oversized Primary Suite with double door entry makes up the right wing of the home. It showcases two large walk-in closets, a separate water closet with window, a linen closet, a large, tiled walk in shower with grab bars and a tiled bench to sit on. The vanity with double sinks compliments the bathroom area. The Primary Suite with trey ceiling and ceiling fans can accommodate a separate sitting area for relaxation or larger bedroom furniture. The 2nd Suite with double door entry is on the left side of the home. It's accessible from the dinette area and from the hallway that leads to the 3rd Bedroom/3 Bath. The 2nd Suite has a private bath and built in closet. The 2nd Suite Bath features a comfort height vanity, walk in shower with glass enclosure, grab bars, foot rest and comfort height toilet. Overnight Guests will enjoy their own bedroom and bath with shower/tub combo and comfort height vanity. The Laundry Room (FLEX ROOM) is spacious and well designed with a wash tub and portable storage units for your personal items. The washer/dryer are included in the sale of this home. The outdoor living space offers a delightful place for entertaining. There are two OPTIONS: You can enjoy the covered portion of the lanai or the extended/uncovered screened lanai with direct views of the golf course and lake. The double car garage is sizeable and there is a separate golf cart entrance. The home also has a WHOLE HOUSE GENERAC- this is a huge bonus! ADDITIONAL IMPROVEMENTS to this home include: NEW INTERIOR PAINT and NEW LUXURY VINYL FLOORING. The community of Lake Ashton is a hidden treasure with an aura of peace and tranquility, and offers 2 golf courses, tennis courts, 2 pools (one indoor and one outdoor) movie theater, bowling lanes, card, craft and billiard rooms, fitness centers, pickleball courts, indoor basketball, indoor racquetball, numerous recreational activities, and restaurants. Make an appointment today to TOUR THIS HOME!

6136 Pebble Beach Boulevard, Winter Haven

Courtesy of LAKE ASHTON REALTY INC.

$219,900
3 Beds ⋅ 2 Baths ⋅ O6439949 MLS
Come and see this 3-bedroom, 2-bathroom single-story home in the Lesnick Park neighborhood. This property features a spacious open floor plan that seamlessly connects the main living areas for an airy, comfortable feel. The kitchen is well-appointed with beautiful countertops and sleek appliances. A standout feature of the home is the primary bedroom, which includes a large walk-in closet for excellent storage. Situated in the heart of southeast Winter Haven, the location offers superb convenience. You are just minutes away from local schools, a variety of shopping and dining options, and nearby medical facilities. Schedule your private showing today!

806 Avenue L Se, Winter Haven

Courtesy of ENTERA REALTY LLC

$364,999
5 Beds ⋅ 3 Baths ⋅ TB8547214 MLS
Under Construction. Indigo BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails.  Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

5441 San Pietro Drive, Winter Haven

Courtesy of CASA FRESCA REALTY

$300,000
3 Beds ⋅ 2 Baths ⋅ TB8546687 MLS
Virtually Staged. Welcome to this beautiful, move-in-ready home offering comfort, style, and easy maintenance! Step inside to a bright and inviting layout featuring no carpet throughout the home, making everyday living and upkeep a breeze. The kitchen is equipped with updated appliances and provides a functional space for preparing meals and entertaining family and friends. Step outside to the screened-in back porch, the perfect place to relax and enjoy the Florida weather while overlooking the backyard. Whether you're enjoying your morning coffee, unwinding after a long day, or hosting guests, this outdoor space adds even more room to enjoy the home. Conveniently located in Winter Haven with access to shopping, dining, schools, and major roadways, this home is ready for its next owner. Schedule your showing today and see everything this property has to offer!

477 Kensington View Drive, Winter Haven

Courtesy of MARK SPAIN REAL ESTATE

$106,000
2 Beds ⋅ 2 Baths ⋅ P4939801 MLS ⋅ Lakeridge BLDG.
**THIS CONDO IS PRICE TO SELL !!**CENTRAL FLORIDA 55+ Age GATED CONDOMINIUM COMPLEX WITH LAKE AND CITY VIEW. All new insulated windows throughout. This condominium provides 1,347 sq. ft. of living area & is located in the beautiful "Chain Of Lakes" City of Winter Haven, Fl. Very friendly complex w/ social activities offered if you wish to participate. Monthly association fee includes water, sewer, trash, fiber optic cable & internet, condo reserves, manager and use of recreational facilities. Lakeridge Condominiums offers a maintenance-free lifestyle w/ heated pool, tennis, shuffleboard, community room, gated entrances & covered assigned parking space. The large bright kitchen has plenty of cabinets & great counter space, appliances (dishwasher does not work) & pantry closet. The kitchen overlooks the 26'x14' great room that also adjoins the additional bonus space & storage closet. The 16X14 foot Primary bedroom suite has a walk in closet & bathroom w/ walk-in shower. Beautiful views of Spring Lake can be enjoyed from Primary bedroom & living areas. The 2nd bedroom & bath can be a private guest area or for your personal use for office, hobbies etc. The washer & dryer are included in the sale. Central heat and air conditioning. Convenient proximity to shopping, places of worship, groceries & restaurants. Extra assigned storage bin on same floor. Make this your full time home, winter home or investment property to update. Lakeridge Condominiums is an age-restricted, well-maintained & well-managed community. Sharepoint car charger provided for those with electric cars. Non-smoking property. 1 pet, 20 pounds or under may be approved.

1776 6th Street Nw Unit 304, Winter Haven

Courtesy of JUDY B CLEAVES PROPERTIES INC

$515,000
3 Beds ⋅ 2 Baths ⋅ TB8546901 MLS
Welcome home to this spacious 3-bedroom, 2-bath pool home offering 2,269 square feet of living space, with an inviting layout designed for everyday living and entertaining. Topped with a new metal roof, this home combines valuable recent improvements with plenty of character inside and out. Step inside to an open and expansive living area highlighted by exposed wood beams, recessed lighting, and tile flooring throughout much of the main living space. The updated kitchen features luxury cabinetry, quartz countertops, subway tile backsplash, stainless steel appliances, abundant storage, and generous counter space, all flowing naturally into the dining and living areas. An additional bonus/game room offers exceptional flexibility and could serve as a billiards room, home theater, playroom, office, or second family room. The primary suite features a spacious walk-in closet and an updated bathroom with a large dual-sink vanity, modern fixtures, and beautifully tiled walk-in shower. Step outside to your own Florida retreat featuring a private in-ground swimming pool, paver deck, and tropical landscaping. The expansive screened lanai overlooking the pool provides plenty of covered space for outdoor dining, entertaining, or simply relaxing and enjoying the Florida lifestyle year-round. Additional highlights include a dedicated indoor laundry room, generous storage, spacious secondary bedrooms, multiple living areas, and a large backyard. With its new metal roof, updated interior, private pool, screened outdoor living space, bonus room, and 2,269 square feet of living space, this Winter Haven home delivers the space, versatility, and indoor-outdoor lifestyle today's buyers are looking for.

44 Brevard Drive, Winter Haven

Courtesy of SCHLEICHER SELECT PROPERTIES

$182,000
3 Beds ⋅ 1 Baths ⋅ O6440388 MLS
Auction Property. 3-bedroom, 1 bath, 1,080 square foot ranch home sitting on 10,097 square foot lot. Cyprus Gardens, Lego Land and a few Parks near you can recharge your energy. Only a short distance from the Orlando International airport. Make it your own. Jump on this great deal before its gone! All buyers are responsible to confirm City, County, Zoning, Tax, and other records to their satisfaction before bidding. No inspection contingencies in contract. Absolutely no repairs before closing. This property is sold As-Is. This is a REO auction property.

679 Avenue L Se, Winter Haven

Courtesy of REALHOME SERVICE & SOLUTIONS INC

$370,000
4 Beds ⋅ 3 Baths ⋅ P4939817 MLS
HOME SWEET HOME! This sweet 4 bedroom 3 bath home is ready for its next happy homeowner. Located in a small gated community in SE Winter Haven this one has the perfect combination of location, and comfort. Check out the homey kitchen with granite countertops and wood cabinets. The corner pantry can hold all your treats for those football weekend get togethers. The rooms have large windows offering abundant natural light, and space for everyone. The ideal 3 way split bedroom plan offers form, and function. The spacious yard offers peace, and privacy with a PVC-fenced back yard, and extra storage in a charming 10x12 planters shed. The 2025 architectural shingle roof, 2017 AC dual zone AC system, and Generac generator have you covered in all Florida weather. Check out this sweet property today. Step inside, fall in love. Make it yours!

754 Santa Maria Dr, Winter Haven

Courtesy of CENTURY 21 WATSON & MYERS REALTY

$399,900
4 Beds ⋅ 3 Baths ⋅ L4964789 MLS
Freedom and flexibility await in this amazing 4 bedroom, 3 bathroom ranch-style POOL home, featuring beautiful updates, a floor plan ideal for multi-generational needs, and a detached garage offering plenty of room to store your boats, ATV's, Jet Skis or hot rods! Situated on a .6-acre cul-de-sac lot right across the street from Eagle Lake with NO HOA, here you are tucked away from it all, with space to enjoy your own private piece of paradise. Crisp landscaping, a covered front entry and an extended driveway make a nice first impression. It is clear from its tasteful updates and excellent condition that this home has been lovingly maintained. You will appreciate the attractive finishes, knockdown ceilings (no popcorn!), stylish fixtures and solid flooring throughout. The layout offers options and space, with formal and informal living areas, a separate formal dining room and triple split bedrooms, including two with en-suite bathrooms. An updated primary suite provides a peaceful retreat, with a spacious bedroom, walk-in closet, and a gorgeous bathroom including a jetted tub, dual sinks, and a walk-in shower. The second en-suite at the back of the home is a wonderful space for guests or live-in loved ones of all generations, with a bedroom including a Murphy Bed, a refreshed bathroom, and convenient access to the pool. There are also two additional bedrooms and a guest bathroom down a hallway, providing separation from the rest of the home. The remodeled kitchen is stunning, with white soft-close cabinetry, stainless steel appliances, closet pantry, quartz countertops, and a breakfast bar with seating. A window from the kitchen sink overlooks the remodeled pool area. The pool was recently resurfaced, with a new pump and salt system, a screen enclosure and a large, covered paver lanai - perfect for relaxation and entertaining. Green space is ample in the back yard, with room and hookups to park up to a 45-foot RV, and a private air-conditioned shed for a workshop, gardening or hobbies. The incredible 30x40x14 garage, however, is the highlight of this area, with two 12 foot roll up doors, concrete floors, side walk-in door and 1 window. Just imagine what you could do in this space! Solar panels (2023) provide efficiency in this home, while other key system updates include water heater (2024), well pump (2026), driveway (2024), A/C (2022), and Culligan water system (2023). The best part about this home, though, is that it is a FUN place to live! You really can make this space all your own, enjoying your time inside and out, with easy access to the water and all that Central Florida living has to offer! **LOCATED IN A USDA ELIGIBLE AREA**

5014 Sunrise Drive, Winter Haven

Courtesy of KELLER WILLIAMS REALTY

$269,900
3 Beds ⋅ 2 Baths ⋅ L4964764 MLS
Welcome to this beautifully maintained 3-bedroom, 2-bathroom home in Winter Haven, built in 2023 and offering the feel of a nearly new home without the wait for new construction. The open and inviting layout features durable vinyl flooring throughout, creating a clean and modern look with easy maintenance. Thoughtful upgrades include a black aluminum privacy fence, an expanded two-car driveway, and paver walkway for added curb appeal. Inside, matte black faucets and door hardware throughout the home add a stylish, contemporary touch. The spacious backyard provides plenty of room for outdoor entertaining, pets, gardening, or simply enjoying Florida’s beautiful weather. With no HOA, you’ll have added flexibility and freedom without monthly association fees or restrictions. Conveniently located in Winter Haven, this move-in-ready home combines modern finishes, desirable upgrades, and a low-maintenance lifestyle. Schedule your showing today!

1200 33rd Street Nw, Winter Haven

Courtesy of 54 REALTY LLC

$379,000
4 Beds ⋅ 2 Baths ⋅ P4939766 MLS
Step into a piece of Winter Haven history—beautifully reimagined for modern living. Just moments from Lake Howard, this exceptional 1925 residence offers the character and craftsmanship today's luxury buyers crave, paired with a complete top-to-bottom transformation. Original refinished 101 year old hardwood floors and two sets of original French doors provide a timeless connection to the home's past, while the rest has been thoughtfully rebuilt with today's lifestyle in mind. The custom kitchen, elegant architectural details, crown molding, tray ceilings, and spacious living areas create a home that feels both sophisticated and inviting. The private primary suite is a true retreat, featuring his-and-hers walk-in closets and a spa-inspired ensuite with a two-person tiled shower, garden tub, and generous vanity space. Two additional bedrooms upstairs add flexibility for guests, family, or a private home office. With approximately 2,011 heated square feet, 4 bedrooms, 2 baths, a dedicated laundry room, fully fenced backyard, and no HOA, this is a rare opportunity to own something with genuine character—not another cookie-cutter home. Bring your boat and water toys and enjoy the freedom and lifestyle that come with living near Winter Haven's beautiful Chain of Lakes. For buyers who appreciate history, character, and modern luxury, this is a home that simply must be experienced in person.

2112 Avenue C Sw, Winter Haven

Courtesy of KELLER WILLIAMS REALTY SMART 1

$145,000
3 Beds ⋅ 2 Baths ⋅ O6437272 MLS ⋅ 1 BLDG.
**Welcome to Imperial Harbours, a beautifully maintained 55+ active community surrounded by gorgeous landscaping and offering access to Winter Haven’s Chain of Lakes!** This spacious **3-bedroom, 2-bath second-floor corner condo** offers over 1,226 sq. ft. of comfortable living with an open-concept living/dining area, lovely kitchen with beautiful countertops and abundant cabinetry, plus an enclosed bonus room perfect for an office, sitting area, or hobby space. The generous primary suite features a private bath and large walk-in closet. Enjoy the peace of mind of a **BRAND-NEW A/C**, newer double-pane windows, updated bathroom vanities, fresh interior paint, and an in-unit washer and dryer. Additional features include an exterior storage unit, elevator access, covered assigned parking, guest parking, and community car wash. Enjoy resort-style amenities including a **heated pool, fitness room, billiards, recreation room, shuffleboard, BBQ grills, gazebo, fishing, dock access, and nearby boat ramp.** HOA includes **water, internet, cable, and trash!** Conveniently located near hospitals, restaurants, shopping, and everyday essentials. **Come experience the Florida lifestyle at Imperial Harbours—schedule your private showing today!**

333 Lake Howard Drive Nw Unit 204D, Winter Haven

Courtesy of UNITED REAL ESTATE PREFERRED

$274,999
3 Beds ⋅ 2 Baths ⋅ O6438788 MLS
Virtually Staged. Virtual stage. Move-in ready and beautifully renovated! NEW ROOF TO BE INSTALLED PRIOR TO CLOSING! This beautifully updated home features brand-new luxury vinyl plank flooring throughout, fresh interior paint, and a completely remodeled kitchen with elegant quartz countertops. A new roof will be installed prior to closing, along with new cabinetry, a new microwave, and a new range. The bathrooms have also been tastefully renovated with modern finishes, creating a fresh and contemporary feel throughout the home. Conveniently located near shopping, dining, schools, and major roadways, this home is perfect for first-time buyers, families, or investors. Don't miss this incredible opportunity—schedule your private showing today!

3947 Warbler Drive, Winter Haven

Courtesy of FLORIDA REALTY INVESTMENTS

$152,000
2 Beds ⋅ 2 Baths ⋅ O6439573 MLS ⋅ 350 BLDG.
SERENE WATERFRONT LIVING ON THE CHAIN OF LAKES 2 Bedrooms | 2 Full Bathrooms | 1,073 SQFT | Single-Story Villa-Style Condo. Water Views & Chain-of-Lakes Lifestyle! Welcome home to low-maintenance living with a view! Situated in the desirable waterfront community of Winter Ridge, this turn-key 2-bedroom, 2-bath end unit pairs interior updates with living on Lake Smart. Unlike multi-story apartment complexes, this single-story villa design offers easy entry and maximum privacy. Step onto your private 8x17 screened-in covered lanai to enjoy the outdoors pest-free. Fresh & Fully Modernized Interior. Inside, the refreshed open-concept living space awaits. Stylish, water-resistant Luxury Vinyl Plank (LVP) flooring runs seamlessly throughout the home—no carpet! Enhanced by a fresh, clean, neutral paint palette. Gourmet Galley Kitchen: Features a full suite of modern appliances, a closet pantry, ample cabinet storage, and an integrated indoor laundry area. Primary Suite Sanctuary: A spacious retreat showcasing a large walk-in closet and an updated en-suite bathroom. Capital improvements include a brand-new roof (2025) and an updated water heater, offering buyers significant savings on home insurance and maintenance. Living at Winter Ridge feels like a year-round vacation on the Winter Haven Chain of Lakes: Boater’s Dream: Take advantage of direct access to Lake Smart via the private community boat launch ramp and fishing dock. Active Recreation: Unwind in the geothermal heated community pool, social clubhouse, or on the shuffleboard courts. Prime Parking: Includes two dedicated parking spaces, including a covered carport directly near your front entrance. All-Ages Community: Unlike many surrounding lakefront complexes that enforce age restrictions, Winter Ridge is an all-ages community, making it ideal for primary homeowners, snowbirds, or long-term investors. Location & Convenience: Nestled in Central Florida’s lake country with quick access to US-17, US-27, and I-4. Enjoy a short 10-minute drive to charming Downtown Winter Haven dining, shopping, medical centers, Polk State College, and LEGOLAND Florida. Low-maintenance waterfront living, major structural updates, and direct chain-of-lakes access—schedule your private tour today!

350 Winter Ridge Boulevard Unit 350, Winter Haven

Courtesy of RP INVESTMENT REALTY LLC

$184,900
2 Beds ⋅ 2 Baths ⋅ B4902354 MLS ⋅ Hartridge Landing BLDG.
Great condo in Hartridge Landings. A premier 55+ small 42 unit custom condominium complex Walking out the front door one can find themselves only a few steps from the clubhouse, pool and the famous Chain of Lakes...Lake Hartridge. 17-lake chain of inter-connected lakes. Boating and fishing enthusiasts paradise! Well maintained. This home comes with several skylights to brighten your day. It also has several custom shelves and engineered closet built-ins. Large totally private rear patio area that's great for entertaining outside and room to add a portable spa. Large double car garage with some storage closets. New TPO roof, re-piped plumbing and a/c system in 2022. Vacant and easy to show.

2215 Starboard Drive Unit 29, Winter Haven

Courtesy of KLINE REAL ESTATE SERVICES

$279,900
4 Beds ⋅ 2 Baths ⋅ O6439455 MLS
Virtually Staged. Welcome to this beautiful one-story Freeport floor plan featuring 4 bedrooms, 2 bathrooms, an open-concept kitchen and great room, a private primary suite with a walk-in closet, a patio, and a two-car garage. The home also includes solar panels, offering incredible energy savings even during August, one of the hottest months of the year; the electric bill was under $20! The buyer must assume the existing solar-panel account. Don’t miss this wonderful opportunity to enjoy a comfortable home with significantly lower energy costs!

1020 Cambridge Drive, Winter Haven

Courtesy of CAPITAL HOMES INC

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