Winter Haven Single Family Homes For Sale - 708 homes

Remarks: Move in ready and located on the Winter Haven Chain of Lakes! Welcome to the gated community of Casarena on the Lakes. This well-designed and meticulously maintained home is set up just right for indoor and outdoor living. The first floor is an open design with the fireplace separating the living and dining area. Enjoy granite countertops and updated appliances in the spacious kitchen that provides the perfect setting to create all of your favorite culinary delights. The living area is a versatile space with a cove for a hosting or exercise area. The main floor is also equipped with a half bath. Head upstairs to the loft that overlooks the living area and separates the two bedrooms. The primary bedroom leads to an open balcony on one side and an updated bathroom on the other. Both bedrooms are oversized with plenty of closet space. The new metal roof was installed in October 2023, The HVAC system has been well maintained, there is a new water heater and the home is also equipped with a whole home generator that is tested regularly. Enjoy the community pool, tennis or pickleball court and access to Lake Cannon, which is on the Winter Haven Chain of Lakes. Downtown Winter Haven is only 10 minutes away and you have quick access to Hwy 92 and 27. Call today for your private showing.

Listing is courtesy of: HOMETRUST REAL ESTATE & PTY MGT (863-450-0602)

Listing Agent: Kami Rickert (954-629-7828)

Remarks: Welcome home to Peach Crossings, a brand-new community in Winter Haven! This stunning three-bedroom, two-bathroom home is designed for modern living, featuring an open-concept layout and stylish finishes. The kitchen is a chef’s dream, offering plenty of counter space for meal prep and entertaining. It comes fully equipped with Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave—all included at no extra cost! The granite countertops and sleek cabinetry add a touch of elegance and timeless appeal. This home also features high ceilings, enhancing the open and airy feel throughout the living spaces. Step outside to the covered patio, a perfect spot for relaxing, dining, or enjoying the beautiful Florida weather. This home is also packed with energy-efficient upgrades, including double-pane windows, a programmable thermostat, coach lighting, and a Wi-Fi-enabled garage door opener for added convenience. A mudroom located off the garage provides a dedicated space to store shoes, bags, and coats, keeping your home neat and organized. Plus, it’s conveniently placed next to the laundry room for maximum functionality. Nestled in Polk County, Peach Crossings offers a perfect blend of serene lake living with easy access to shopping, dining, and top attractions. Families will love the highly-rated Polk County schools, while the community itself features a playground and a picnic area for residents to enjoy. This home is move-in ready with all upgrades included! Schedule your tour today

Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)

Listing Agent: Gayle Van Wagenen (904-449-3938)

Remarks: Under contract-accepting backup offers. Impeccably maintained home in the sought-after Traditions 55+ community in Winter Haven! This spacious 2-bedroom, 2-bath home with a dedicated office/den offers over 1,500 square feet of open-concept living space, designed for both comfort and functionality. The home features new flooring throughout, upgraded countertops, 36-inch kitchen cabinets, and modern lighting fixtures, creating a bright and inviting kitchen and living area perfect for everyday living or entertaining. Both bathrooms have been tastefully upgraded, and additional improvements include a new water heater and recently replaced AC coil for added efficiency and peace of mind. The home was freshly painted inside and out in 2023, giving it a clean, modern feel throughout. Step outside to enjoy the new screened-in porch, ideal for relaxing mornings or evening gatherings while overlooking the newly installed sod that enhances the home’s curb appeal. The extended driveway provides additional parking and convenience, and the home is handicap accessible, offering added functionality and ease of living. Residents of Traditions enjoy resort-style amenities, including community boat ramp access, fishing, dock, and private water access, along with a community pool and recreational facilities. The HOA includes cable TV, internet, exterior, grounds maintenance, pool maintenance, recreational facilities, and security, making this a truly low-maintenance lifestyle. Located just minutes from shopping, dining, and major roadways, this move-in ready home combines modern updates, accessibility, and the vibrant lifestyle of one of Winter Haven’s most desirable active adult communities.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)

Remarks: Welcome to the Summit model in Peach Crossings, a beautiful brand-new home featuring four bedrooms and two bathrooms with an inviting open-concept design. This home boasts high ceilings, enhancing the spacious and airy feel throughout. The master retreat is a true sanctuary, offering a generously sized bedroom that connects to a luxurious en-suite bathroom with a dual sink vanity for added convenience and a step-in shower for a spa-like experience. The kitchen is designed for both function and style, featuring exceptional counter space and brand-new Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave. A spacious hall closet provides extra storage, keeping everything organized. The family room is the perfect space for cozy movie nights, with ample room for a large sectional and entertainment setup. Whether it’s a movie marathon or a casual night in, this space is designed for relaxation, laughter, and quality time with loved ones. Step outside to the lanai, an ideal spot for enjoying warm Florida evenings with family and friends. The home also features professional front yard landscaping, adding to its curb appeal. Located in the heart of Polk County, Peach Crossings offers the best of lake living with easy access to shopping, dining, and top attractions. Families will love the highly-rated Polk County schools, and the community features a children’s playground and picnic area for added enjoyment. With all upgrades included, this home is move-in ready! Schedule your showing today!

Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)

Listing Agent: Gayle Van Wagenen (904-449-3938)

Remarks: Under contract-accepting backup offers. This 2022-built 'Hayden' model in Squires Grove surpasses new construction, offering five generously sized bedrooms and a flexible open-concept floor plan. The property features a bright, south-facing backyard, ideal for enjoying Florida afternoons, a contemporary kitchen equipped with granite countertops, and the assurance of a low-risk Flood Zone X designation. Avoid the typical waiting period for new construction and transition into this energy-efficient smart home promptly. This residence is perfectly suited for either a primary dwelling or an investment opportunity. We encourage you to schedule an appointment to view the home today.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Delaindse Leon (407-791-7595)

Remarks: Discover this must-see Tarragon home. Included features: an inviting covered entry; an expansive great room; a quiet study; a well-appointed kitchen offering quartz countertops, stainless-steel appliances, 42" cabinets, a walk-in pantry, a center island and an adjacent dining area; a convenient laundry; an impressive primary suite showcasing a spacious walk-in closet and a private bath; a mudroom and an extended covered patio. This could be your dream home! *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!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: New construction home with 2005 square feet on one-story including 3 bedrooms plus a den, 2 baths, and an open living area. Enjoy an open kitchen with Silestone countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, 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, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. ***Please note - Virtual Tour showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey!

Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)

Listing Agent: George Lindsey, Iii (863-797-4999)

Remarks: Better than new! Completely Remodeled! This 3 bedroom 2 bath home has been completely remodeled, to include a new a/c, new water heater, a beautiful new kitchen, new flooring, new lights & fixtures, and new paint, and the roof was replaced in 2023.

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Dwight Head (863-965-0207)

Remarks: One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 2-bath home in Winter Haven offering 1,334 sqft of comfortable living space; this well-designed home features a functional layout for everyday living, with a bright and inviting living area that flows seamlessly into the dining and kitchen spaces; the bedrooms provide flexibility for family, guests, or a home office, while the 1-car garage adds convenience and additional storage; whether you’re a first-time buyer or looking to downsize, this home offers great potential in a desirable location—don’t miss out, schedule your private showing today!

Listing is courtesy of: REALTYCITY INC (863-438-6605)

Listing Agent: Jesse Carriedo (863-438-6605)

Remarks: Discover waterfront serenity at 5840 Gray Heron Drive, a beautifully maintained Winter Haven retreat featuring a roof replaced just two years ago and a luxurious master bathroom fully renovated in June 2025. This home boasts stylish flooring updated in 2018 and offers a private backyard sanctuary with breathtaking views of a large pond, perfectly complemented by community amenities including two sparkling neighborhood pools. Conveniently located near local favorites like Port 27 and the world-class family fun of Legoland Florida Resort, this property combines modern peace of mind with a premier Florida lifestyle.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Christopher Warschauer (863-257-6677)

Remarks: DON"T SCROLL PAST THIS BEAUTIFUL DESIGNER HOME in the PREMIER Active 55+ Community in LAKE ASHTON. You will LOVE THE EXPANSIVE WATER VIEW OVER THE LAKE in the back. You can see the LAKE easily from the extended Screen Veranda, LOOKING TOWARDS THE CLUBHOUSE and OVER THE GOLF COURSE with FRONTAGE ON the 2ND GREEN of the WEST COURSE...and the SUNSETS are GORGEOUS. This amazing DESIGNER CUSTOM BUILT HOME has everything you are looking for..... From the Beautiful Front Door, the Amazing Stone Accent on the front corners of the house, Gutters on the Front, Side and Back of the home and the Enclosed Screened Entrance ... To the exceptional entrance with High Ceilings, and offering Coffered and Tray Ceilings in the Great Room and Master Bedroom. When you enter this amazing HOME, you will be awed by the Beautiful Designer Features that this home offers, that gives it an elegance that you will admire and enjoy for years to come. ... A Huge benefit in choosing this home is that "You" are going to save thousands on this property because the CDD DEBT IS COMPLETELY PAID IN FULL! The OPEN FLOOR PLAN sets the stage for seamless living combined with elegance. This HOME IS MOVE-IN READY. Some of the many designer upgrades in this home include: Large 20" Diagonal Tile throughout the home in most rooms with excellent upgraded carpeting in the bedrooms, the Gourmet Kitchen with Stainless Steel Appliances, which is open to the Great Room, has 42" All Wood Cherry Cabinets w/ crown molding "bump up and out cabinets, high end Tile Backsplash ( 2022) New Range (2022) Dishwasher (2023) Stainless Steel Refrigerator, Custom Pendant lights over the Kitchen Bar that looks into the GREAT ROOM, and beautiful Granite that completes the designers influence. The Exterior of the house has been Painted in 2025. This floor plan allows easy access to the extended Veranda through the 3 Sliding glass doors which opens from the Great Room into the Large SCREENED Veranda (14 X 34). The View looks over the Golf Course and Lake in the back. The Expanded Den creates a comfortable reading or gathering room for friends and family. The Master Bedroom boasts of a Tray Ceiling and sliders with Silhouette Vertical Blinds that lead to the Expanded Veranda. Throughout the house you will enjoy Designer Ceiling Fans, Window Tinting, Vertical Cellular Blinds at the Kitchen and Great Room Sliders, also Designer upgrades in the bathrooms that compliment the Master Bathroom Suite. Other important upgrades are the NEW ROOF in JULY 2025, Newer Water Heater in 2020, and the A/C is only 6 years old. The 2 car + Golf Cart garage with the added MOTORIZED SCREEN on the garage door along with the added protection with the insulated Garage Doors. Also, the large garage adds additional storage and leads into the inside laundry giving added room for the Washer and Dryer and Walk in Pantry. You will enjoy the Active Lifestyle present in Lake Ashton that sets this community apart from other communities in the Central Florida area. 2 Large Clubhouses, 3 Natural Lakes, 2 Private Golf Courses, Bowing Alley, Movie Theater, Tennis, Pickleball, Basketball court indoor, 2 Pools, 1 indoor and 1 outdoor Pool with Hot Tubs, Sauna, 2 Fitness Centers, Cards, Crafts, Entertainment, Fishing, Boating and close to stores, shopping, and lots or Restaurants. Call today for your private tour and see how much this Active Lifestyle Community will add to your health and enjoyment during these Golden Years.

Listing is courtesy of: ROOST REALTY GROUP LLC (863-398-0267)

Listing Agent: Barb Wiechmann (863-255-9130)

Remarks: Under contract-accepting backup offers. Florida classic with NEW ROOF now available in Winter Haven! This 3/2 is close to everything, and walking distance to the High School. A/C was replaced in 2022, all appliances convey, and home is clean and move-in ready! Home also includes 2 living areas, a large screened porch (carport), a dining area with terrazzo floors, and a huge backyard with shade tree. Better Hurry!

Listing is courtesy of: STORMS REALTY (813-293-4652)

Listing Agent: Steve Storms (813-293-4652)

Remarks: Welcome to 551 Lake Smart Blvd, located in the heart of Winter Haven! This fabulous home features 4 bedrooms, 2 bathrooms, and offers a spacious 1,936 square feet of thoughtfully designed living space with a modern open floor concept—perfect for both everyday living and entertaining. Built in 2020, this home combines contemporary style with peace of mind, including a brand-new roof installed in 2025. Step inside to enjoy a bright and airy layout with generous living areas, a well-appointed kitchen, and comfortable bedrooms designed to fit your lifestyle. Conveniently located just minutes from restaurants, shopping, and major roadways, this property offers both comfort and accessibility in one of Winter Haven’s most sought-after communities. Don’t miss this incredible opportunity to own a beautiful, move-in-ready home in a prime location. Schedule your private showing today!

Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)

Listing Agent: Kenneth Gonzalez (407-860-2304)

Remarks: One or more photo(s) has been virtually staged. This Fully Renovated Gem is ready to go! New Roof at Closing! This beautifully renovated 3-bedroom, 2 bathroom home in Winter Haven, Florida, offers modern living in a serene neighborhood near shopping and seasonal markets. The open-concept layout features a spacious living area, a new kitchen with brand-new stainless steel appliances, and stylish finishes throughout. Each bedroom is generously sized, with the master suite boasting a luxurious walk in Closet. The home also includes a cozy backyard, perfect for relaxation and large shed. Located in a quiet neighborhood, this home combines comfort, convenience, and contemporary charm, making it the perfect place to settle down.

Listing is courtesy of: ALIGN RIGHT REALTY LLC (727-264-6800)

Listing Agent: Austin Williams (516-782-1553)

Remarks: Welcome to a place where everyday life feels like a getaway. Set along the peaceful shores of Lake Jessie, part of Winter Haven’s renowned Chain of Lakes, this lakefront retreat is more than just a home, it’s a lifestyle defined by water, sunshine, and unforgettable experiences. Start your mornings with breathtaking sunrises shimmering across the lake, coffee in hand from your private dock or patio. Spend your days exactly how you choose, cruising the Chain of Lakes by boat, casting a line in some of Central Florida’s best freshwater fishing, or enjoying world-class watersports like skiing, wakeboarding, and paddleboarding right from your backyard. With nearby slalom courses and open water, this is truly a paradise for water enthusiasts. Lake Jessie is especially cherished for its tranquil atmosphere, offering a rare sense of calm while still being full of life. One of its most unique features is the seaplane activity, where you can watch planes gracefully land and take off across the water, an experience that never gets old and adds to the charm of lakeside living. Nature lovers will also appreciate the frequent sightings of all kinds of birds and other beautiful wildlife. The home itself offers a thoughtfully designed single-story layout with over 1,800 square feet, featuring 3 bedrooms and 3 bathrooms. An open-concept living space is filled with natural light and showcases stunning lake views, while a split-bedroom design provides comfort and privacy. A private in-law suite with its own entrance adds flexibility for guests, multi-generational living, or additional income potential. This residence offers plenty of parking space with it's oversized driveway and an additional carport providing covered parking as well. The home has been updated with modern finishes and includes a metal roof installed in 2019. This home would make a perfect full time residence, investment property or second home. Beyond the water, the location is just as appealing. You’re right around the corner from a brand new Publix store and minutes from the heart of Winter Haven, where you’ll find charming local restaurants, shops, parks, and community events. Legoland Florida Resort is just a short drive away and there is convenient access to both Tampa and Orlando, so world-class attractions, dining, and entertainment are always within reach. Whether you're seeking adventure, relaxation, or a smart investment, this Lake Jessie property delivers it all, offering the rare opportunity to live, play, and unwind in one of Florida’s most iconic lakefront settings. Book your showing today!

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

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

Remarks: New - New - New! This 3 bedroom 2 bath features a beautiful lake view and has been completely remodeled. Updates include a new HVAC system, new metal roof, new kitchen with granite counters, new bathrooms, new flooring, and new septic system. No HOA means you can store your boat. Can be purchased together with 73 High Street to make a family compound or have an income producing property. (MLS P4937859)

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Dwight Head (863-965-0207)

Remarks: Welcome to your dream home, a charming 2-bedroom, 2-bath retreat with a versatile bonus room that can be used as a 3rd bedroom or a separate home office featuring its own private exterior entrance! This inviting home has been thoughtfully refreshed and is move-in ready, offering fresh interior paint, a new smart thermostat, recent tree removal, and a brand-new shingle roof (03/24) for peace of mind! Inside, you’ll find a spacious kitchen with a breakfast bar that opens to a bright living room, ideal for everyday living and entertaining. The large dining room or secondary family room is conveniently located next to the kitchen and provides plenty of space for gatherings. Relax in the cozy Florida room, featuring warm wood walls and ceilings and an abundance of windows where you can enjoy views of Lake Elbert! Outside you will find your large paver patio, perfect for entertaining or unwinding, and enjoy the privacy of a newly built fully fenced backyard. Additional updates include a new AC (2022), blown attic insulation (2022), water heater (2019), all kitchen appliances (2021), and Exterior Front Porch paint along with a new front door (2025). Conveniently located just minutes from Downtown Winter Haven, Polk State College, HWY 27, and medical facilities, this home blends comfort, flexibility, and an excellent location. Schedule your showing today!

Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)

Listing Agent: Jenna Henderson (850-524-3843)

Remarks: One or more photo(s) has been virtually staged. Under Construction. 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. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. 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.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: Welcome to this modern residence at 6212 Pinehurst Loop Winter Haven, Fl. 33884, designed with 3 Bedrooms and 2 full bathrooms PLUS an additional room that could be used as a Den/Office. This delightful Sebastian home, with screened entry was BUILT in 2022 and features a spacious living area with abundant natural light, an upgraded kitchen paired with a Large Island (Great for additional seating and entertaining), Upgraded Lighting, Stainless Steel appliances and Silestone countertop. The inviting living and dining areas blend seamlessly together with newly installed carpet. The open-concept layout is beautifully enhanced by new tile plank flooring in the kitchen, laundry, guest bathroom/hall, entry and perimeter of the Living Room, offering a sleek and modern feel. Bedroom 1 and Bedroom 2 are located to the right of the front entry and the guest bathroom with comfort height vanity and shower/tub combo is conveniently located between Bedroom 1 and 2. The guest bath has a glass block above the shower/tub combo. The primary suite with newly installed carpet offers a private retreat on the back of the home, complete with a generously sized bathroom, walk-in closet, separate comfort height vanities, and an oversized shower. Step outside and enjoy the lanai, perfect for entertaining and equipped with an extended birdcage. The flooring on the lanai has been beautifully painted and it adds a touch of class to the space. The laundry room is spacious and is accessible from the garage and kitchen. The garage floor has an epoxy coating. This home blends style and functionality, making it an exceptional choice! The exterior of the home has been well maintained with beautiful landscaped flower beds and the double car garage and the separate golf cart entry is a bonus. Don't miss the opportunity to explore this wonderful property! Lake Ashton is a Florida Retirement Community that offers a Florida Retirement Lifestyle with resort style amenities and activities for 55+ in Florida. The main clubhouse offers a movie theater, bowling lanes, grand ballroom, card, craft and billiards, Restaurant (Charm City), outdoor temperature controlled swimming pool, Bocce Courts, tennis courts, 1/2 court basketball, shuffleboard courts and MORE. The Health and Fitness Center has a large indoor temperature controlled pool, fitness center, indoor 1/2 court basketball, indoor racquetball, large multi-purpose room, card, craft, billiards, pickle ball courts and tennis courts. 2 -18 hole golf courses are located in Lake Ashton (memberships are optional). Tour this well maintained home today! You'll be glad you did!

Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)

Listing Agent: Lori Raath (863-409-6899)

Remarks: Under contract-accepting backup offers. Welcome to 4504 Riviera Drive. This is a unique custom home, built by renowned builder, Bob Coons. This is one of only two homes ever constructed with this exclusive floor plan and was proudly featured in the 1985 Parade of Homes. This beautiful updated home offers a remodeled kitchen and bathrooms, hardwood floors throughout, and a spacious upstairs bonus room that could make the perfect home office, media room or guest space. There is even a striking coral rock fireplace that serves as a stunning focal point of the living room which adds warmth and character. Major upgrades provide peace of mind, including a brand-new roof (November 2025) and all new hurricane rated, energy efficient windows throughout the home. With its custom design, thoughtful updates, and timeless charm, this exceptional property offers outstanding value. Do not miss the opportunity to make this home yours.

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Renard Ellis (863-412-8820)