Homes for Sale Near Lake Region High in Winter Haven - 161 homes

Remarks: This well-maintained 4-bedroom, 3-bathroom pool home is located in the sought-after gated community of Tuscany at Winterset, offering both comfort and style in a prime setting. Inside, you’ll find an inviting layout highlighted by solid surface countertops, elegant tray ceilings, and detailed crown molding that adds a refined touch throughout the living spaces. Major updates provide peace of mind, including new windows (2025), a newer roof (2021), kitchen remodel (2023) and an updated HVAC system (2023). Step outside to enjoy the brick-paved driveway and your own private pool (2020)—perfect for relaxing or entertaining. The property also features a dedicated well for irrigation, helping maintain the landscaping efficiently. This home combines thoughtful upgrades, functional features, and a desirable location—an excellent opportunity in one of the area’s most desirable gated communities.

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

Listing Agent: Tony Insua Jr. (863-221-0656)

Remarks: Under contract-accepting backup offers. ****PRICE IMPROVEMENT**** This home presents an exceptional opportunity to own in one of Winter Haven’s most desirable 55+ communities. This beautifully maintained 2-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and effortless Florida living. Step inside to a bright, open-concept layout where the living and dining areas flow seamlessly into the kitchen—creating an inviting space ideal for both everyday living and entertaining. Large windows flood the home with natural light, highlighting the clean, well-kept finishes throughout. What truly sets this property apart is the oversized fenced backyard and extended pavered screened-in porch—a rare find in the community. This private outdoor retreat provides unmatched space and flexibility. Whether you have pets, enjoy gardening, or simply value extra room to unwind, this backyard delivers both privacy and possibility. The expanded screened porch feels like a true extension of the home—perfect for outdoor dining, hosting guests, or enjoying peaceful mornings and relaxing evenings in comfort. The primary suite offers a tranquil escape, complete with a walk-in closet and glass-enclosed shower. A spacious secondary bedroom provides versatility for guests, a home office, or hobby space. Thoughtfully designed and move-in ready, this home allows for low-maintenance living so you can fully enjoy the lifestyle you deserve. Residents of Traditions at Lake Ruby enjoy resort-style amenities including a 19,000-square-foot clubhouse, heated pool and spa, fitness center, tennis and pickleball courts, scenic walking trails, and private lake access to Lake Ruby—all just minutes from shopping, dining, and medical facilities. With its recent price improvement, exceptional outdoor space, and prime location, this home stands out as one of the best values in the community. Schedule your private showing today before this opportunity is gone.

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

Listing Agent: James Barris (863-258-6321)

Remarks: Quick Move-in! Introducing Villa Mar in Winter Haven, Florida. Master-planned amenities including a pool with cabana that is walking distance from your home, a playground, and shaded seating area. Highway 27, less than 10 minutes away, has everything you are looking for. Grocery stores, movie theaters, shopping centers, golf courses, restaurants, and so much more. The Windermere single-family home is where you want to be. Step in from the 2-car garage and enjoy the good life. Find it in the large family room, where smiling faces greet you and delicious smells fill the gourmet kitchen. Share stories around the island or outside on the lanai. The 1st floor also features a study. Upstairs, 3 bedrooms and a full bath provide privacy while a loft adds extra entertaining space. Your deluxe owner’s suite includes double vanities, a seated shower and a walk-in closet, making The Windermere can’t-miss. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

Listing is courtesy of: MALTBIE REALTY GROUP (813-819-5255)

Listing Agent: Bill Maltbie (813-819-5255)

Remarks: Welcome to this beautifully maintained 3BR/2BA + den home in the desirable gated community of Mandolin in South East Winter Haven! Offering over 2,000 sq ft, this move-in-ready home features a bright open floor plan, vaulted ceilings, and a spacious great room with a striking reclaimed wood accent wall. The kitchen is designed for both everyday living and entertaining, showcasing cherry cabinetry, stainless steel appliances, a breakfast bar, and a cozy nook, plus a formal dining area for gatherings. The split-bedroom layout provides privacy, with a generous primary suite featuring dual walk-in closets, dual vanities, a garden tub, and separate shower. A versatile den makes the perfect home office or flex space. Enjoy peace of mind with a newer roof (2022) and water heater (2025), along with updated flooring and fresh interior paint. Step outside to a screened lanai overlooking a large fully fenced backyard—ideal for relaxing or entertaining. Situated on a .26-acre lot with mature landscaping and irrigation, this home also includes a 2-car garage and excellent curb appeal. Conveniently located near shopping, dining, major highways, and local attractions like Legoland, this home offers the perfect combination of privacy, convenience, and Florida living at its best.

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

Listing Agent: Suzie Rudd (863-287-7861)

Remarks: One or more photo(s) has been virtually staged. Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. 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.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: **SELLERS OFFERING $5,000 CLOSING COST CREDIT** Welcome to the community of Eagle Landing in beautiful SE Winter Haven, Florida. This newer home features 4 Bedrooms/2.5 Bathrooms with a spacious two-story layout that maximizes space and natural light perfect for any lifestyle with Low HOA and NO CDD. The modern kitchen design with Island and Breakfast Bar complete with Granite countertops. The primary bedroom with en-suite bathroom with dual sinks, walk in shower and walk-in closet and 3 additional bedrooms offers plenty of space for a growing family or multi-general family. The solar panels feature a great savings to help keep your energy cost down. Conveniently located in a quiet neighborhood, this property is ideally situated close to Publix, Legoland, schools and the Winter Haven Chain of Lakes. If you're looking for a modern, quiet neighborhood, this is your chance. Schedule your showing today before it's gone!

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

Listing Agent: Cheryl Brewer (863-224-0045)

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, with no rear neighbors, 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. This home is 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 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: One or more photo(s) has been virtually staged. 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.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: One or more photo(s) has been virtually staged. Under Construction. This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient two-car garage. 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.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: One or more photo(s) has been virtually staged. This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient two-car garage. 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.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Welcome to the Summit model in Peach Crossings, a stunning brand-new home offering four bedrooms and two bathrooms with a spacious open-concept design. Featuring high ceilings, this home is bright and airy, providing a welcoming atmosphere throughout. The master suite is a true retreat, offering a large bedroom that leads into a luxurious en-suite bathroom with a dual sink vanity and a step-in shower for a spa-like experience. The kitchen is both functional and stylish, with exceptional counter space and brand-new Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave. A spacious hall closet adds extra storage, keeping everything organized. The family room is perfect for movie nights, providing plenty of space for a comfortable sectional and a large entertainment setup. Whether it’s a movie marathon or a quiet evening, this room is designed for relaxation and family fun. Step outside to the lanai, a great place to enjoy the warm Florida evenings with family and friends. The home also features professional front yard landscaping, adding to its curb appeal. Located just a short walk from the children’s playground, this home is perfect for families. In addition to being close to shopping, dining, and local attractions, the community offers access to top-rated Polk County schools and a picnic area for residents to enjoy. With all upgrades included, this home is ready for you to move in! 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. Don’t miss your chance to own this fully rented quadplex offering immediate cash flow. All four units are currently occupied with month-to-month tenancies paying $1200 per month, giving a new owner flexibility to increase rents to market value or renovate units for added equity and higher returns. Each unit features: 2 Bedrooms / 1 Bathroom, spacious living and dining room combination, dedicated laundry room with washer/dryer hookups, gas stoves and hot water heaters. The roof is only 5 years old. Whether you’re looking to expand your portfolio or secure a strong income-producing property, this quadplex checks all the boxes with built-in upside potential.

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

Listing Agent: Harold Baker (863-604-6272)

Remarks: Under contract-accepting backup offers. This custom Built by Waters, Inc. home sets a higher standard of quality. Live the LAKE LIFE in Waterford Oaks with CHAIN OF LAKES ACCESS via the community private boat ramp on Lake Winterset. Lake Winterset is part of the Winter Haven Chain of more than twenty beautiful lakes. Are you looking for a home with a private pool and a large yard? You don't have to compromise here! Welcome to your HALF ACRE LOT with FRUIT TREES, PRIVACY, a PRIVATE screened-in SALTWATER POOL featuring a SUNSHELF, water features, and a shaded lanai. GATED COMMUNITY. Single story home with SOARING CEILINGS. Four bedrooms - Four FULL BATHROOMS (this means three en suites). A dedicated OFFICE. Breakfast nook in the kitchen and a formal dining room. OPEN FLOOR PLAN design. Custom-built kitchen that skipped no detail: You have Tier 3 granite, soft-close cabinets, a double wall oven, a gas stovetop, a slide-out spice cabinet, recessed square LED lighting, solid wood cabinets with crown molding, exterior vented exhaust, a hidden pantry, and stainless steel appliances. Custom features include CROWN MOLDING, WOOD BEAM COFFERED CEILING, PORCELAIN TILE, ENGINEERED LUXURY VINYL. Plenty of storage and a large laundry room. A new breaker box by the pool includes an available breaker for a pool heater. 2024 whole home surge protector. Gas Water Heater. Washer and dryer included. Kinetico whole house water softener with a filtration system with a separate tap for drinking water. FAST ELECTRIC CAR CHARGER. THREE CAR GARAGE. Built in surround sound system with Yamaha Woofer. HVACs 2017 & 2024. Home has a well for the irrigation and home has ten irrigation zones available. GOLF CARTS are welcome in this community. Along with the BOAT RAMP you can also fish off the community dock. The surrounding area has lots to offer. ADVENT HEALTH FIELD HOUSE AND CONFERENCE CENTER has fitness and sports facilities. A BRAND NEW PUBLIX Grocery Store and 7/11 only two minuets from the home. PORT 27 is a great local spot to enjoy great food and live music and entertainment. TARGET COMING very SOON. ADVENT HEALTH is building a major medical complex in Winter Haven. This home checks every box and will not last long. Schedule your private showing today.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Ken Pozek (407-813-2773)

Remarks: Under contract-accepting backup offers. Short Sale. Packed with potential! This spacious two-story home, featuring 4 bedrooms, 2.5 baths, and a versatile bonus room needs some repairs, cleaning, and TLC, but that’s where the attractive price comes in! The main floor includes a large great room, white kitchen with granite countertops, front living room/den, laundry, enclosed bonus room and a 3-car garage. The lanai offers a great outdoor entertaining space. Upstairs, the primary suite offers dual sinks, tub and separate shower, and dual walk-in closets, and the other bedrooms. Not in a flood zone and low HOA fees of $165/year ensure long-term low cost of ownership. Trustee Sale, must sell!

Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)

Listing Agent: Tanja Cisliek (727-480-4155)

Remarks: Completely renovated and move in-ready Large 4 bedroom, 2 bathroom house awaits your family! On a desirable corner lot, in a quiet neighborhood. New Roof, New Paint, New Flooring all through the house, New Stainless Steel Appliances, New Kitchen Faucet, Like a New Home!! Master Bath has a walk in closet and Garden Tub and Seperate Shower with a Seat. This home offeres a Separate Dining area and a Office or Playroom. Close to the new Polk Parkway extension, so travel to schools, shopping, restaurants and entertainment is super convenient. Great school district and priced to sell quickly. Call today for a showing!

Listing is courtesy of: AVERY PROPERTIES INC. (863-682-1902)

Listing Agent: Anne Greenhow (863-698-4562)

Remarks: This BEATIFUL HARPER Model home is located in the quaint town of Winter Haven. Ski capital & home of LEGOLAND. The NEWLY UPDATED HARPER has 4 bedrooms, 2baths & a 2-car garage - 1665 SqFt. This new model has an open floor plan with a spacious GREAT room off the kitchen to entertain & enjoy the company of your guests. You will love the split floor plan with beautiful & spacious master suite with walk in closet & en suite bathroom away from the other 3 bedrooms. Home comes with WHIRLPOOL Stainless Appliances- range, hood microwave, refrigerator & dishwasher. Home also comes with faux wood blinds throughout & has Smart Home Technology which allows you to set the scene & connect to your home with your voice, from your smart phone. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries. *

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: Under Construction. This BEATIFUL HARPER Model home is located in the quaint town of Winter Haven. Ski capital & home of LEGOLAND. The NEWLY UPDATED HARPER has 4 bedrooms, 2baths & a 2-car garage - 1665 SqFt. This new model has an open floor plan with a spacious GREAT room off the kitchen to entertain & enjoy the company of your guests. You will love the split floor plan with beautiful & spacious master suite with walk in closet & en suite bathroom away from the other 3 bedrooms. Home comes with Stainless Appliances- range, hood microwave, refrigerator & dishwasher. Home also comes with faux wood blinds throughout & has Smart Home Technology which allows you to set the scene & connect to your home with your voice, from your smart phone. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: Under Construction. This BEATIFUL HARPER Model home is located in the quaint town of Winter Haven. Ski capital & home of LEGOLAND. The NEWLY UPDATED HARPER has 4 bedrooms, 2baths & a 2-car garage - 1665 Sq Ft. This new model has an open floor plan with a spacious GREAT room off the kitchen to entertain & enjoy the company of your guests. You will love the split floor plan with beautiful & spacious master suite with walk in closet & en-suite bathroom away from the other 3 bedrooms. Home comes with WHIRLPOOL Stainless Appliances- range, hood microwave, refrigerator & dishwasher. Home also comes with faux wood blinds throughout & has Smart Home Technology which allows you to set the scene & connect to your home with your voice, from your smart phone. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: Under Construction. Introducing the Harper floorplan at Villamar, where every square foot is put to use with sophistication and comfort. Inside this 4 bedroom, 2 bathroom home, you’ll find 1,665 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing granite and tile floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The chef's kitchen is a true highlight, boasting granite countertops, sleek stainless steel appliances, and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms offer flexibility for various lifestyles. The primary suite is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Like all homes in Villamar, the Harper includes all concrete block and also smart home technology, which allows you to control your home anytime with your smart device while near or away. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. Contact us today and find your home at Villamar. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: Under Construction. Introducing the Harper floorplan at Villamar, where every square foot is put to use with sophistication and comfort. Inside this 4 bedroom, 2 bathroom home, you’ll find 1,665 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing granite and tile floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The chef's kitchen is a true highlight, boasting granite countertops, sleek stainless steel appliances, and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms offer flexibility for various lifestyles. The primary suite is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Like all homes in Villamar, the Harper includes all concrete block and also smart home technology, which allows you to control your home anytime with your smart device while near or away. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. Contact us today and find your home at Villamar. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)