Winter Haven Single Family Homes For Sale - 711 homes

Remarks: Better Than New 2022 Home – Move-In Ready! VA Assumable Mortgage!!! Welcome to this beautifully maintained 3-bedroom, 2-bath home with a 2-car garage, located on a desirable corner lot in the sought-after Villamar community of Winter Haven. Built in 2022, this home offers modern living without the wait for new construction. Step inside to an open and inviting floor plan featuring tile flooring throughout the main living areas, with comfortable bedrooms and a spacious primary suite. The kitchen comes equipped with appliances and flows seamlessly into the living and dining areas, making it perfect for everyday living and entertaining. Enjoy outdoor living in the screened lanai, ideal for relaxing or hosting guests. The home also includes an irrigation system and established landscaping, features often not included in new builds. Located in a community with resort-style amenities including a pool, playground, and sidewalks, and just minutes from shopping, dining, and local schools, this home offers both convenience and lifestyle. Skip the construction wait, this home is vacant and ready for immediate move-in! Don’t miss your opportunity to own a newer home in a growing area at an incredible value. Schedule your private showing today!

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

Listing Agent: Regina Moran Pa (863-698-0748)

Remarks: Welcome to this beautifully updated home in Winter Haven! This move-in ready property combines classic charm with modern upgrades, featuring stunning high-gloss marble-style porcelain flooring throughout that creates a bright and elegant living space. Enjoy a spacious layout filled with natural light, a well-maintained kitchen with stainless steel appliances, wood cabinetry, and a stylish backsplash — perfect for everyday living. The home also offers a renovated bathroom with modern finishes and a convenient interior laundry area. Step outside to a large, fully fenced backyard, ideal for entertaining, pets, or simply enjoying your own private outdoor space. The covered carport and extended driveway provide ample parking. Located in a quiet, well-established neighborhood, this home is perfect for first-time buyers or investors. Property is being sold AS-IS, presenting a great opportunity for buyers looking for value and flexibility. Schedule your private showing today!

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

Listing Agent: Gabriel Rivera Gonzalez (407-724-4717)

Remarks: Ready Now! 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 Glen Ridge single-family home is your key to great living. An open floor plan makes entertaining a breeze. Play a game in the family room or gather round the dining room table for a delicious meal, home cooked in the gorgeous gourmet kitchen with large island and walk-in pantry. The 2-car garage offers convenient extra storage. Upstairs, 2 bedrooms and a full bath give guests plenty of privacy. Make the most of your loft by using it as a second living space or media center. Your luxury owner’s suite includes dual walk-in closets and double vanities. You’re going to love The Glen Ridge. 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 charming and well-maintained home in the heart of Winter Haven! Situated on a spacious lot, this property offers a perfect blend of comfort and functionality with an open-concept layout, abundant natural light, and inviting living spaces. The kitchen features ample cabinetry and flows seamlessly into the main living area, making it ideal for both everyday living and entertaining. Enjoy a generously sized backyard with plenty of room for outdoor activities, gardening, or relaxing in your own private space. Conveniently located near shopping, dining, schools, and major roadways, this home provides both tranquility and accessibility. A fantastic opportunity for homeowners or investors alike—schedule your showing today!

Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)

Listing Agent: Bridd Bone (727-798-1918)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. WATERFRONT CUSTOM St. John floor plan with CDD bond debt PAID IN FULL! Recent Upgrades: Kinetico whole-house water softener, refrigerator (2025), New roof (2024), AC, dishwasher, stove, additional screened room with pavers, and upgraded landscaping (2022). Experience Florida living at its finest in this beautifully upgraded 3-bedroom + den, 2-bath home, complete with an enclosed Florida room and extended screened lanai. From the moment you arrive, you’ll notice the attention to detail: custom stacked stone accents, a power screen on the garage door, golf cart garage entrance, upgraded landscaping, a front paver patio, screened entry, and elegant beveled double glass doors. Inside, round columns frame the dining area, while raised stone archways lead to the kitchen and breakfast nook. The great room features coffered ceilings with recessed lighting, a ceiling fan, and double crown molding that flows throughout the home. The kitchen boasts a bank of drawers, 42" raised-panel custom cabinets with crown molding, stainless steel appliances, a large prep island with extra storage, granite countertops, pendant lighting, and a breakfast bar. Wake up to serene views from your primary bedroom, complete with sliding doors to the lanai. The en-suite bath features two walk-in closets, a walk-in shower, double vanities, a soaking tub, and a linen closet. Enjoy two clubhouses, two 18-hole golf courses, bowling, a movie theatre, craft & card rooms, billiards, pickleball, tennis, bocce, and so much more.

Listing is courtesy of: A+ REALTY LLC (863-293-1141)

Listing Agent: Emily Muscarella (863-978-7180)

Remarks: Short Sale. "SHORT SALE!! Seller accepting CASH ONLY!! APPROVED SHORT SALE PRICE BY LIEN HOLDER. Needs TLC. This midcentury POOL home has much potential. It features 3 bedrooms and 3 baths. It has a formal living room area, an office area and a large dining/family room for family gatherings. The fireplace has been converted to gas. Pool enclosure can be developed to be an amazing outdoor space. There is NO HOA, NO CDD and NO FLOOD ZONE is this well-established neighborhood. Located close to popular restaurants, shopping centers, and Legoland Florida Resort & Park, banks and lakes. It is tucked away, yet close to it ALL.

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

Listing Agent: Kelly Hansell (863-557-1784)

Remarks: Discover this well maintained 2 bedroom, 1 bathroom home offering 1,206 sq ft of comfortable living space. The home features a practical layout with a functional living area and kitchen. The bedrooms are well sized, and the property offers a spacious yard with room to enjoy. Located in a quiet residential neighborhood, this home is easy to show and ready for its next owner!

Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)

Listing Agent: William Figueroa (305-662-1502)

Remarks: Under contract-accepting backup offers. DON'T MISS THIS 3 BEDROOM 2.5 BATH HOME CENTRALLY LOCATED IN WINTER HAVEN, FL ON AN OVERSIZED (.39 ACRE) LOT WITH NO HOA!!! Featuring nearly 2,000 SqFt. of heated and cooled living space, this 2-owner home was constructed of BLOCK AND BRICK! The OPEN-CONCEPT, SPLIT BEDROOM PLAN, and CENTRALLY LOCATED KITCHEN share both privacy and convenience. There is plenty of natural light in the main living area and especially through the glass sliders leading to the back yard. In the event more privacy is preferred, just hit the remote button for the MOTORIZED BLINDS, which are also INCLUDED IN THE SALE. For those looking for an OVERSIED GARAGE, this one plenty of workspace for several different hobbies. There is no shortage of parking whatsoever on this HUGE CORNER LOT! Opportunity awaits at this lovely residence, which is located in close proximity to LEGOLAND, FL, medical, shopping, dining, schools, and the many freshwater lakes Winter Haven features. Winter Haven is also located between ORANDO INTERNATIONAL and TAMPA INTERNATIONAL AIRPORT, and the most recently added AVELO AIRLINE in LAKELAND, FL!!!

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

Listing Agent: Wanda Dicks (863-287-7846)

Remarks: Brand new, energy-efficient home available NOW! First-floor primary suite ensures everyone has their own private space. Second floor offers a spacious loft that can be used to best fit your family's needs. Enjoy preparing meals with your family in the open kitchen with spacious work island. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS. : Offers may be entered ONLINE through Monday, May 4, 2026 at 2:00 pm. Welcome to this beautiful 3-bedroom, 2-bathroom block home perfectly positioned at the end of a quiet cul-de-sac in Winter Haven's sought-after Cypress Gardens neighborhood. With 1,400 square feet of interior living space and a layout designed for both comfort and connection, this home checks every box. Step inside and you're immediately greeted by a bright, open floor plan where the living room, dining area, and kitchen flow together seamlessly ideal for everyday living and effortless entertaining. The kitchen is generously sized, featuring an abundance of cabinetry and two lazy Susan's that maximize every inch of storage. Natural light floods the home through an impressive array of windows, and sliding glass doors in the main bedroom, middle bedroom, and living room all open directly onto the crown jewel of this property: a stunning 47 x 15 screened-in patio complete with a bar area, built-in grill, refrigerator, and cabinetry. Whether you're hosting guests or simply enjoying a quiet Florida evening, this outdoor space delivers. Both bathrooms have been tastefully updated. The guest bath features a brand-new tub and shower installed by Westshore Homes in October 2025, along with a new vanity, mirrored medicine cabinet, cabinet above the toilet, and new toilet. The main bathroom has also been refreshed with a new mirrored medicine cabinet, cabinet above the toilet, and new toilet. Major systems are all squared away brand-new roof in 2025, A/C replaced in 2021, and water heater from 2018 offering true peace of mind from day one. The home is also pre-wired for a generator, a smart bonus for Central Florida living. The attached garage includes a dedicated laundry and storage room with extensive shelving, and the washer and dryer convey with the home. Set on an 8,537 square foot lot at the end of a tucked-away cul-de-sac, this property offers the rare combination of privacy, space, and convenience. Just minutes from US-27, LEGOLAND Florida Resort, Winter Haven Hospital, Polk State College, and the renowned Chain of Lakes, everything Central Florida has to offer is right at your doorstep. Homes this move-in ready, this well-maintained, and this well-located don't stay on the market long schedule your private showing today! Offers may be entered ONLINE through Monday, May 4, 2026 at 2:00 pm. AT SELLER'S DISCRETION, A SUBMISSION MAY BE ACCEPTED AT ANY TIME.

Listing is courtesy of: NEW HEIGHTS REALTY GROUP (407-934-0305)

Listing Agent: Daniel Rodriguez (407-934-0305)

Remarks: Short Sale. Welcome Home to this 5 bedroom 3 bath POOL Home on a large corner lot in Winter Haven. Upgrades galore. NEW ROOF, NEW POOL EQUIPMENT, 2 NEW A/C UNITS. The home features luxury vinyl wood flooring throughout. The kitchen has been renovated featuring white wood shaker cabinets, quartz countertops and stainless steel appliances. The bathrooms have been fully renovated as well and feature modern updated finishes. The living room features a large brick fireplace. The large fenced in backyard has a large underground pool just waiting for its new homeowners to spend their afternoons building memories and soaking up the Florida sun. The front of the home features 2 driveways. This home is close to Legoland, Lakes galore and amazing shopping, dining and entertainment.

Listing is courtesy of: ELEVATE REALTY LLC (561-427-3923)

Listing Agent: Laura Auten (561-427-3923)

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

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

Listing Agent: Gino Dapello (954-790-0632)

Remarks: Charming and inviting, this 3-bed, 2-bath home sits in a lovely Winter Haven community with a very low HOA. Built in 2015, it offers a modern design, a comfortable one-level layout, a 2-car garage, and all appliances included. Tucked into the vibrant Chain of Lakes region, you’re surrounded by peaceful views, leafy lakes, and plenty of outdoor fun from boat cruises to paddle boarding. And when it’s time for entertainment, you couldn’t be better located: you’re just 20 minutes from LEGOLAND Florida Resort, and only about 30 miles from Walt Disney World, making magical Orlando day trips effortless.

Listing is courtesy of: MARZUCCO REAL ESTATE (813-679-1365)

Listing Agent: Clarisa Moody (813-446-2003)

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and living area. A dreamy, covered lanai, accessible through sliding glass doors, invites you to take full advantage of the Florida climate. The owner’s suite boasts double vanities, a walk-in shower and a substantial walk-in closet, while the additional bedrooms and full bathroom are located off the kitchen for added privacy. With a laundry room located off the foyer, a smart thermostat with voice control to maintain energy efficient living, and professionally curated landscaping, the Magenta is designed to make every day extraordinary. 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. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change.

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

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

Remarks: One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and living area. A dreamy, covered lanai, accessible through sliding glass doors, invites you to take full advantage of the Florida climate. The owner’s suite boasts double vanities, a walk-in shower and a substantial walk-in closet, while the additional bedrooms and full bathroom are located off the kitchen for added privacy. With a brand-new washer and dryer conveniently located off the foyer, a smart thermostat with voice control to maintain energy efficient living, and professionally curated landscaping, the Magenta is designed to make every day extraordinary. 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: One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Welcome to The Azure, where modern design meets practical living in a home that has it all. With 4 bedrooms, 2.5 bathrooms, and a 2-car garage, this home is crafted for comfort and style. The extraordinary elevation and professionally designed landscaping create a captivating first impression. Step through the front door to discover luxurious vinyl plank flooring that extends throughout the open-concept layout. The kitchen shines with quartz countertops and all-new stainless-steel appliances, overlooking the dining area and patio. A convenient half bath is located downstairs for guests, while the spacious laundry room upstairs comes complete with a brand-new washer and dryer. Upstairs, you’ll find all four bedrooms, including the expansive owner's suite with a walk-in shower, double vanities, and a spacious walk-in closet. A flexible recreation space upstairs provides an ideal spot for family gatherings. With a smart thermostat ensuring energy efficiency and comfort, the Azure seamlessly blends functionality and modern luxury. 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.

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

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

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and living area. A dreamy, covered lanai, accessible through sliding glass doors, invites you to take full advantage of the Florida climate. The owner’s suite boasts double vanities, a walk-in shower and a substantial walk-in closet, while the additional bedrooms and full bathroom are located off the kitchen for added privacy. With a laundry room located off the foyer, a smart thermostat with voice control to maintain energy efficient living, and professionally curated landscaping, the Magenta is designed to make every day extraordinary. 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.

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

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

Remarks: Seller motivated. Welcome to your home in Winter Haven—just minutes from Legoland, shopping, medical facilities, and Highway 27 for easy commuting! Originally a 3-bedroom, 2-bath layout, this home has been converted into a spacious 5-bedroom, 2-bath residence, offering incredible versatility for growing families, multigenerational living, or those needing extra space for a home office or hobby rooms. It will need some TLC due to tenant being in property. With five true bedrooms, everyone in the family can have their own retreat while still enjoying generous shared living spaces. Outside, you’ll find a property ideally situated for convenience—whether you’re heading to Legoland for weekend fun, accessing everyday amenities just minutes away, or commuting via Highway 27. This home offers the perfect blend of location, and space in one of Winter Haven’s most desirable areas.

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

Listing Agent: Brandy Duncan (863-585-6849)

Remarks: Under contract-accepting backup offers. Welcome to the Serendipity floor plan — where comfort meets style! This stunning three-bedroom, den, two-bathroom home offers the perfect blend of modern design and everyday convenience. Step inside to find a bright, open-concept layout featuring high vaulted ceilings, a spacious great room, a beautifully appointed kitchen with a large island and walk-in pantry, and a cozy dining area ideal for gatherings. The owner’s suite provides a peaceful retreat with dual walk-in closets and a luxurious en-suite bath. The flexible den is perfect for a home office, guest space, or hobby room, offering versatility to fit your lifestyle. Enjoy year-round outdoor living in the beautiful enclosed lanai overlooking the fully fenced backyard—perfect for relaxing or entertaining in privacy. Located in a highly desirable area, this home offers convenient access to top-rated schools, shopping, dining, parks, and houses of worship. Designed for both elegance and functionality, the Serendipity truly lives up to its name—a happy discovery of the place you’ll love to call home.

Listing is courtesy of: CORCORAN CONNECT LLC (407-953-9118)

Listing Agent: Kelly Martinez (407-864-8965)

Remarks: Situated in the desirable gated community of Terranova, this wonderful 3-bedroom, 2-bath pool home with a den offers comfort, and efficiency. Enjoy low energy costs thanks to the FULLY PAID SOLAR SYSTEM, providing long-term savings and sustainability. Upon arrival, you’re welcomed by a lovely covered entry accented with a leaded glass front door and arched transom window, filling the foyer with natural light. The spacious great room features hand-scraped engineered wood flooring and a large sliding glass door that seamlessly brings the outdoors in, offering views of the patio and pool area. The well-appointed kitchen showcases white cabinetry with brushed nickel hardware, beautifully complemented by a glass tile backsplash. Stainless Steel Appliance Package includes a Gas Range. A granite-topped breakfast bar with pendant lighting provides additional seating and creates a natural gathering space. A formal dining room is conveniently located nearby, making entertaining effortless. The primary bedroom suite offers a walk-in closet and a cozy sitting niche—ideal for relaxing while enjoying views of the pool. The primary bathroom is thoughtfully designed with dual sinks, a linen closet, walk-in shower, private water closet, and a luxurious garden tub. Step outside to your private outdoor oasis. The lagoon-style pool with a cascading waterfall creates a tranquil ambiance, while the covered patio provides shade from the Florida sun and convenient access to the guest bath—perfect for poolside gatherings. A fully fenced yard ensures privacy and features an avocado and citrus trees. Additional Features: Den/office, Laundry room with washer and dryer, Solid surface flooring throughout, Water heater (2020), Architectural shingle roof (2020), 18 SEER Carrier HVAC system with heat pump (2020) and warranty, In-wall pest control system, Pull-down attic stairs, Irrigation well, Smart lock entry, Child safety fence for pool, Exterior carriage lighting, Oversized driveway, Two-car garage with door opener and keyless entry panel. This fabulous home is conveniently located in a picturesque gated community near schools, shopping, restaurants, and Legoland, offering the perfect blend of luxury, convenience, and energy efficiency.

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Eileen Belanger (863-221-0229)