Winter Haven Homes For Sale & Real Estate - 979 homes

Remarks: ***Investor Special*** Welcome to this 2 bedroom 1 bath home. It is in need of some work but not out of range for the right do it your self investor. It is situated on .6 acres of land with room on the back of the lot for a garden, chickens or storage building. This property is located in Winter Haven and is close to everything you need.

Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)

Listing Agent: Craig Burke (863-899-5010)

Remarks: Under contract-accepting backup offers. A stunning home featuring three spacious bedrooms and two bathrooms with a desirable split bedroom plan. Built in 2021, this residence offers a generous 2,200 square feet under roof, seamlessly blending an open floor layout with the latest technology for exceptional value in one incredible package. Enjoy the convenience of a smart home with automated lighting, climate control, and advanced security access, all designed to bring comfort and efficiency right to your fingertips. The architectural roof is less than a year old, and the energy-efficient construction ensures lower utility costs and sustainable living. This property also includes a water softener, washer, and dryer, all of which stay with the home for added value. If buyers need assistance with closing costs, the seller is open to considering support, making this an even more attractive opportunity. Seller will leave Living room, dining room furniture, big screen tv in master, if buyer desires.

Listing is courtesy of: BROKER’S REALTY AND CONSULTING (863-557-3265)

Listing Agent: Patty Clemons (863-557-3265)

Remarks: Nestled in the heart of Winter Haven just north of Lake Lulu, this charming block home captures the true essence of a hometown retreat. Inside, the 1,338 square feet of living space feels warm and inviting, featuring a classic living and dining layout that flows into a versatile Florida room—currently used as a cozy third bedroom. Peace of mind comes standard here, thanks to a sturdy roof installed in 2019 and a solid construction that has stood the test of time. Step outside into your private sanctuary, where a spacious 0.24-acre fenced yard offers plenty of room for pets to roam or for gardening under the Florida sun. The property is a hobbyist’s dream, equipped with two large storage sheds (240 and 96 square feet) that provide ample space for a workshop, gear, or seasonal decor. The location truly bridges the gap between quiet residential living and urban convenience; you are just a short, breezy walk from the Publix Shopping Plaza, Walmart, and a variety of local restaurants. For those seeking a bit of magic, LEGOLAND Florida Resort is only 15 minutes away, while the vibrant amenities of downtown Winter Haven are practically at your doorstep. This is more than just a house; it’s a place to plant roots in a community that feels like home. Go ahead and schedule a showing today.

Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)

Listing Agent: Twanna Dewdney (863-207-1634)

Remarks: Lakefront living with a proper sunset! Down a private road with no HOA (because your house shouldn't come with a rule book). This renovated home offers direct frontage 80' on Lake Pansy and a bonus 80' of canal frontage across the street. The property provides excellent water access and endless sunset views. Outside is where this home really shows off with amenities including a heated saltwater pool / lap pool with markers on the bottom, lighting and water features, added style with a surfboard outdoor shower, screened in with panoramic panels because this view deserves center stage. The outdoor summer kitchen is outfitted with a refrigerator, table top ice chest, bar area, and a grill supplied by a 99-gallon propane tank, making it well-suited for entertaining all year round. The lanai is glassed in with cedar tongue and groove ceiling and motorized retractable sunshade, while enhanced landscape lighting and mature palm trees set the tropical tone. Additional exterior upgrades include a composite dock, fenced in yard, seamless gutters with leaf filters, and recently replaced garage and front entry doors. Inside, the vibe continues with an electric fireplace with customizable lighting (because ambiance matters). Live-edge floating shelves with integrated lighting adds a designer touch. Double-pane replacement windows, custom drapes, California Closets, luxury vinyl and ceramic tile throughout, laundry closet for added convenience. The kitchen brings the function and the flair with an island, generous storage, new cabinetry, quartz countertops, a natural gas range with hood ventilation, along with a built in microwave, electric oven, and refrigerator/freezer. Culligan water treatment. The roof and HVAC system are approximately 10 years old. Additional features include epoxy garage floor, LRE foundation improvements, and well-fed irrigation. Prewired generator hook-up installed in garage. The boat ramp is located on the west side of lake Pansy. Conveniently Located 20 minutes from Lego Land, 7 minutes from Publix Super Market, 5 minutes to Home Depot, 3 minutes to the nearest boat ramp to access the Winter Haven Chain of Lakes. This is a rare opportunity to own a turnkey lakefront property with endless sunsets, extensive upgrades, and no HOA restrictions.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Olivia Boggs (863-232-8234)

Remarks: Welcome to easy lakefront living in the highly desirable Sandy Cove community on the Winter Haven Chain of Lakes! This beautiful 2nd floor condo offers low-maintenance living perfect for a full-time residence, seasonal retreat, or investment opportunity. This 2-bedroom, 1-bath condo features a bright and functional layout with comfortable living and dining spaces designed for everyday living and relaxing. The remodeled bathroom adds a fresh, modern touch, while the fully furnished interior makes this property truly move-in ready. Enjoy peaceful mornings and beautiful sunsets just steps from the water. Sandy Cove offers fantastic community amenities including a pool, clubhouse, dock, and fishing pier, creating the perfect Florida lifestyle. Conveniently located near shopping, dining, medical facilities, and all that Winter Haven has to offer.

Listing is courtesy of: WHITMORE PROPERTIES (863-439-7201)

Listing Agent: Samantha Whitmore (863-241-1696)

Remarks: Welcome to your dream lakefront retreat on picturesque Lake Rochelle, part of Winter Haven’s famous Chain O’ Lakes! This beautiful two-story, 4-bedroom, 2.5-bath home combines comfort, style, and Florida living at its finest. Step inside to a bright and spacious living room featuring stunning cathedral ceilings and breathtaking lake views. The kitchen offers ample counter space, a large pantry, and an inviting layout perfect for entertaining or family gatherings. The master bedroom is on the first floor with a walk-in closet and a stunning view to the lake. Upstairs loft area with 3 additional bedrooms and a jack-and-jill bathroom. Convenience meets functionality with a downstairs laundry room, two-car garage, and long driveway providing plenty of parking. The exterior has been freshly painted, giving the home a crisp, updated look that complements its serene waterfront setting. Enjoy mornings with coffee by the lake and evenings watching sunsets reflected on the water. Located just minutes from LEGOLAND, 30 minutes from Disney, and only two hours from both Florida coasts, you’ll have endless recreation and adventure at your doorstep. This lakefront gem blends natural beauty, modern comfort, and an unbeatable location — the perfect place to call home in the heart of Winter Haven, FL. Use Showtime feature to schedule your viewing.

Listing is courtesy of: GATAP REALTY (352-978-5459)

Listing Agent: Roberta San Juan (786-256-1139)

Remarks: Under contract-accepting backup offers. Welcome to 1930 Austin Terrace, located in the highly desirable gated community of Woodpointe in SE Winter Haven. Perfectly situated near Hwy 27 and just minutes from LEGOLAND Florida Resort, this home offers both convenience and a peaceful cul-de-sac setting on a spacious fully fenced 0.32-acre lot.This beautifully designed 4-bedroom, 3-bathroom POOL home welcomes you with an elegant entry foyer, soaring specialty ceilings, and wood flooring throughout, complemented by ceramic tile in the foyer, kitchen, breakfast nook, and bathrooms. The thoughtfully designed layout includes a formal dining room and an open, inviting living space ideal for both everyday living and entertaining. The kitchen features granite countertops, a new refrigerator (04/2026), a breakfast bar, and a walk-in pantry, with a cozy breakfast nook overlooking the saltwater pool for relaxed mornings. Step outside to enjoy true Florida living with a screen-enclosed pool, covered lanai, and a beautifully paved pool patio, perfect for hosting or unwinding in your private, fully fenced backyard. The pool system has been well maintained with a new pool pump (09/2025) and recently updated salt cell and WiFi-enabled motherboard (03/2026), offering modern convenience and efficiency. The spacious primary suite serves as a private retreat, complete with an additional office space, fireplace, walk-in closet, and an ensuite bathroom featuring a split sink vanity, garden tub, and separate shower. Additional highlights include a newer AC system (approximately 4 years old), a brick-paved driveway and walkways, and a charming covered front porch accented by columns, adding to the home’s curb appeal. A brand new roof will be put on before closing! This exceptional property offers the perfect combination of space, style, and location in one of SE Winter Haven’s most sought-after gated communities.

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Charming 3-Bedroom, 2-Bathroom Home in Squires Grove – Move-In Ready! Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the desirable Squires Grove subdivision. This move-in ready property offers modern updates and thoughtful features that make it the perfect place to call home. Step inside to find brand new commercial-grade waterproof laminate flooring throughout, adding both durability and style. The spacious living room is perfect for relaxing or entertaining, while the kitchen includes a cozy eating area ideal for casual family meals. Enjoy Florida living at its best with a screened-in back patio, complete with lighting and tile flooring—a great spot for morning coffee or evening gatherings. The patio opens up to a beautiful back yard, offering added peace and privacy. BRAND NEW A/C system installed in March 2025, ensuring comfort year-round.

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Tony Fridovich (863-698-4267)

Remarks: Pack your bags and move right into this very well maintained home located in Oakwood Estates, a 55+ community. The floorplan offers two living areas with nice sized bedroom. The cathedral ceilings make the living area feel spacious. The functional kitchen provides lots of storage with the built-in in the dining area offering more storage. The home features all new windows, with acrylic windows in the front porch area. The HVAC is one year old. The roof-over was installed approximately 2017. This home comes furnished right down to the dishes, silverware, pots and pans. Oakwood Estates offers many amenities and activities to keep you as busy as you would like, or just sit on the front porch and enjoy the view of the lake.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: LAKEFRONT 3 BEDROOM / 2 BATH HOME WITH PICTURESQUE OPEN WATER VIEWS AND PRIVATE 30 FT DOCK! Located directly on Lake Pansy in the gated subdivision of Hartridge Hills, a quaint lakefront community of approximately 60 homes. NEWER ROOF 2022 and NEWER GENERAC GENERATOR 2020. Lot size is 150 X 83 ft directly on Lake Pansy. Additional lot size in records of 2.44 acres includes riparian or water rights into the lake. Beautiful stone working fireplace with vaulted ceiling in the great room. Spacious kitchen with plenty of storage and breakfast area overlooking tranquil water views. Home was originally constructed with 2,247 sq ft and later the expansive back porch was enclosed bringing the total to 2,958 sq ft of air-conditioned living space under roof. Large windows and sliding glass doors frame panoramic vistas, infusing the space with a sense of tranquility and connection to nature. Attached 2-car garage with large storage room. HOA fees include lawn care, trimming and fertilizer to give you more time to relax. Access to Lake Hartridge and the ‘Chain of Lakes’, a navigable canal system connecting 15 lakes, is obtained from the private community boat ramp and dock. This community is well known and desired by aircraft owners and flying enthusiasts as it is near Gilbert Field-Winter Haven Regional Airport, a city-owned airport that supports over 80,000 flights a year. It is also home to the Jack Brown Seaplane Base renowned as the largest and one of the oldest seaplane training and base operations in the world. Conveniently located between Orlando and Tampa with great attractions, waterfront restaurants, shopping, and some of the best fishing and ski lakes available! Welcome home to endless days of sunshine and relaxation. Please see the interactive 3D virtual tour and floor plan. Virtually staged photos are included.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Kay Szinegh (813-918-0624)

Remarks: Welcome to maintenance-free living in the heart of Winter Haven! This darling 2-bedroom, 2-bath villa is perfectly located in the desirable Imperial Villas a 55+ residential community, sitting within a short walking distance to beautiful Lake Howard. Inside, you’ll find updated flooring throughout and both bathrooms tastefully renovated, giving the home a fresh, move-in-ready feel. The open layout flows seamlessly to a peaceful sitting lanai overlooking the heated community pool—the perfect spot to enjoy your morning coffee or unwind in the evenings. Major updates add peace of mind, including a resurfaced roof with a 15-year warranty, a tankless hot water heater, and an updated electrical system. The low HOA fee of just $270/month covers water, high-speed internet, cable, gas, and all grounds maintenance—you only pay for electric! The property includes 2 assigned parking spaces, with one under a carport, and the community has ample visitor parking. Enjoy easy access to shopping, dining, and downtown Winter Haven events, all while embracing a relaxed, low-maintenance lifestyle close to the lake. Whether you’re downsizing, snowbirding, or looking for carefree Florida living, this villa checks all the boxes. Property is eligible for FHA Financing! Move in, relax, and enjoy the best of Winter Haven living!

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Michele Elchin (863-514-6880)

Remarks: Pack your bags and move right into this fully furnished home. This home has many updates!! Although the bedrooms have updated carpets there is nice wood laminate flooring throughout the main living areas with plywood subfloor. The baths and front porch area have updated tile flooring. The kitchen has newer appliances, a beautiful mosaic backsplash and updated counter tops. All the windows are updated with double pane, thermal, tilt in windows. The updated entry door has blinds between the half glass that you can open for the light or close for privacy. Both bathrooms have updated vanities. Enjoy the updated and modern light fixtures. You get all this, plus the golf cart with new batteries is included in the sale of the home. The HVAC was installed in July 2023. The roof is a roof over adding extra insulation value to the home. Oakwood Estates is an active 55+ communities offering many amenities as well as activities. You can be as busy as you would like or just sit back and enjoy the peacefulness of the community.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: This updated and well-maintained three-bedroom, two-bath home, built in 1990, offers timeless comfort with smart updates. It features a new roof installed four to five years ago, double-paned tinted windows, city water and sewer, plus a dedicated well for the sprinkler system. Inside, you'll find an electric fireplace, updated kitchen with range, refrigerator, dishwasher, washer and dryer. flooring is a mix of tile, laminate, and carpet, a full security system, Ring doorbell, camera system, and a water purifier. The two-car garage comes with an opener, and the fully fenced backyard includes both chain-link and wood sections, a storage shed, and a handy workshop - plus the lawnmower stays with the property. It's a turnkey, low-maintenance gem ready for its next chapter.

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: Teresa Markley (863-207-3457)

Remarks: Need space? This private gated 2.38-acre Winter Haven property with NO HOA offers room to live, play, and grow—bring your RV, boat, ATV, and all your toys. Set well back from the road behind a remote-operated gated entry, this property delivers the privacy and convenience buyers are actively searching for in Winter Haven and throughout Polk County. The fully fenced acreage gives you the freedom to create the lifestyle you want—whether it’s kids playing football or volleyball, evenings around a fire-pit, playground, space for a future pool, or planting your own fruit trees and garden. Inside, the home features an open floor plan with a desirable split-bedroom layout, offering both functionality and comfort. Enjoy formal living and dining spaces for hosting, plus a spacious family room that flows into the kitchen—perfect for everyday living and gatherings. The kitchen is equipped with abundant cabinetry, hardwood flooring, a breakfast bar overlooking your private backyard. The owner’s suite is a peaceful retreat, featuring French doors leading to the screened back porch, a large walk-in closet, and a spa-style bathroom with soaking tub and separate shower. A flexible fourth bedroom near the primary suite provides the ideal space for a home office, nursery, or hobby room. Step outside and experience true Florida living from your 42’ covered front porch or 34’ screened back porch, surrounded by mature trees and open space. This property offers the perfect balance of cleared land for activities and wooded areas for added privacy. Additional features include: * Remote-operated gate for easy access and security * New roof in 2023 * Side-entry 2-car garage + metal carport * Inside laundry room * Well for irrigation & water softener * High and dry acreage *New AC, Well Pump & Water Heater in 2018 *Septic Pumped 2026 Located just minutes from the Polk Parkway, with convenient access to Lakeland, Tampa, and Orlando, this home combines privacy, land, and accessibility—a rare opportunity in today’s market. If you’ve been searching for a gated acreage property in Winter Haven with no HOA and true outdoor living potential, this one checks all the boxes.

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Kimberly Davis (850-625-8855)

Remarks: PRICE REDUCTION – $5,000! Recently Fully Renovated Townhouse – Move-In Ready! Seller offering $4,000 credit toward buyer’s closing costs or interest rate buydown. Don’t miss your chance to own this completely remodeled 2-bedroom, 2.5-bathroom townhouse in Park Lake, now available at an unbeatable price! This home has been beautifully updated from top to bottom, offering modern style and worry-free living: All 3 bathrooms fully renovated with fresh, modern finishes Brand-new kitchen featuring stainless steel appliances (refrigerator, gas range, range hood, microwave), new sink & faucet, New A/C system & new gas water heater for comfort and efficiency Fresh paint throughout (walls, doors, and closets), New vertical and window blinds, New ceiling fans with remote controls and stylish light fixtures in every room, balcony, and lanai, Garage floor freshly painted for a clean, polished look, Washer and dryer included. The spacious main living area is filled with natural light and opens to an extra-large screened lanai, perfect for entertaining or relaxing outdoors. Upstairs, both bedrooms are oversized with private bathrooms, and the primary suite features its own screened balcony. All 3 Bathrooms are renovated, brand new vanities. Prime Winter Haven Location! Next to the new collegiate baseball stadium and parks project, bringing $60M in growth to the city, Direct access to Lake Lulu, part of the Chain of 22 Lakes for boating, fishing, and outdoor fun, Walking distance to dining and shopping: Starbucks, Chick-fil-A, Panera, Outback, Red Lobster, Steps from the Rowdy Gaines Olympic Pool and Advent Fieldhouse, This townhouse is truly move-in ready—all major upgrades are already completed. Perfect as a primary residence, vacation home, or investment property in one of Winter Haven’s most desirable communities. Schedule your private showing today!

Listing is courtesy of: HIGDON HOMES REALTY LLC (863-209-2543)

Listing Agent: Fatma Higdon (863-209-5243)

Remarks: 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!

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: WELCOME TO 3923 BALDWIN LANE, NEW ROOF 2023, NEW A/C 2025, FRESHLY PAINTED 2024. LOCATED IN THE HIGHLY SOUGHT-AFTER TRADITIONS GATED COMMUNITY IN WINTER HAVEN! THIS BEAUTIFULLY MAINTAINED HOME OFFERS THE PERFECT BLEND OF COMFORT, STYLE, AND LOW-MAINTENANCE LIVING. FEATURING SPACIOUS LIVING AREAS, A WELL-APPOINTED KITCHEN, AND A SERENE SCREENED-IN LANAI, IT'S IDEAL FOR RELAXING OR ENTERTAINING. ENJOY RESORT-STYLE AMENITIES INCLUDING A CLUBHOUSE, HEATED POOL, FITNESS CENTER, TENNIS COURTS, AND LAKE ACCESS WITH A PRIVATE DOCK-PERFECT FOR ACTIVE ADULTS 55 AND BETTER! WITH 24-HOUR SECURED GATED ENTRANCE AND A VIBRANT, FRIENDLY ATMOSPHERE. TRADITIONS OFFERS THE LIFESTYLE YOU HAVE BEEN LOOKING FOR. THE SELLERS ARE OFFERING A GENEROUS $8,000 CREDIT TO BE APPLIED TOWARD THE BUYER'S PREPAID EXPENSES AND CLOSING COSTS. THIS INCENTIVE PROVIDES ADDED FLEXIBILITY AND CAN HELP REDUCE OUT-OF-POCKET EXPENSES AT CLOSING, MAKING HOMEOWNERSHIP EVEN MORE ATTAINABLE. SCHEDULE YOUR PRIVATE TOUR TODAY AND EXPERIENCE FLORIDA LIVING AT ITS FINEST.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Brian Reeves (877-366-2213)

Remarks: Under contract-accepting backup offers. Enjoy this clean 2 bedroom, 2 bath villa in the community of Mayfair Place. Step into a spacious great room with soaring ceilings and all ceramic tile floors throughout, offering both style and ease of maintenance. The open kitchen includes plenty of counterspace, gas range/stove, and breakfast bar. The primary suite features sliding glass doors leading to a peaceful back patio, the perfect spot for morning coffee or winding down in the evening. Inside utility room with extra cabinet and counter space, plus an additional storage closet for even more convenience. Just minutes from downtown, this villa provides easy access to local dining, shopping, and medical facilities.

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Waterfront view home on a large lot in amenity-rich community with clubhouse, pool, shuffleboard and fishing pond. This 2 bedroom 2 bathroom home features a completely remodeled kitchen with stone counter tops, custom pull-out cabinetry, and luxury vinyl plank flooring. New carpet throughout most of home. Glass-enclosed Florida room with A/C overlooks pond and clubhouse. The guest bathroom includes a washer and dryer. Widened driveway, deep carport fits car + golf cart. Shed under a carport with water softener and storage/workshop space. Move-in ready partially furnished and conveniently located near all community amenities. Own your land in this 55+ Community. The roof was replaced in 2009.

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Kimberly Davis (850-625-8855)

Remarks: New to the market is this "one owner" villa located in the sought-after Enclave neighborhood located in Cypresswood Golf and Country Club in SE Winter Haven. This 3 bedroom 2 bathroom end unit has just undergone a professional interior paint job. Enjoy Easterly pasture and sunrise views from the lanai. The country club amenities include access to the clubhouse with bar and grill, jr. olympic swimming pool and soon to be completed pickleball courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix is opening a brand new location just a mile down the road which is sure to attract other popular businesses.

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Steven Smith, Pa (863-224-2297)