Winter Haven Homes For Sale & Real Estate - 1002 homes

Remarks: Perfectly situated on a beautiful pond lot, this stunning 4-bedroom, 2-bath home offers over 2,000 square feet of thoughtfully designed living space and was JUST BUILT IN 2024. PAID OFF SOLAR PANELS! Why wait to build when you can move right into a like-new home with upgrades already done? Villamar is a wonderful new home community in Southeast Winter Haven offering a impressive resort-style community pool and playground. Location is key, this home is convenient to everything Winter Haven has to offer including a brand new Publix store opening soon just about 2 miles away! Step inside to discover an open and inviting floor plan with beautiful vinyl plank flooring, featuring a spacious kitchen with a large center island that overlooks the dining and living areas—perfect for entertaining family and friends. The kitchen is also upgraded with granite countertops and attractive stainless-steel appliances. The private owner's suite is tucked away at the rear of the home and features a generous walk-in closet and a spacious en-suite bathroom. The owner has added FULLY PAID OFF SOLAR PANELS AND A WHOLE HOME WATER FILTER AND SOFTENER! Enjoy Florida living year-round from the covered and screened lanai, an ideal space for relaxing while taking in your scenic pond views. The two car garage features an ELECTRIC CAR CHARGER AND EPOXY FLOORING! The fully fenced backyard provides privacy and plenty of room for outdoor enjoyment, making this home the perfect blend of function and style. Schedule your private showing today!

Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)

Listing Agent: Zachary Lay Llc (407-988-6342)

Remarks: ROOF 2022! Enjoy the HEATED SALTWATER POOL all year in your backyard Oasis. LARGE CORNER LOT (.28 acre). SINGLE STORY HOME. Terranova is a GATED COMMUNITY nestled among the Winter Haven Chain of Lakes. LOW HOA. NO CDD. Screened in patio is great for enjoying the beautiful Florida weather. Fully fenced yard with double door gate so you can pull a small boat inside! SPLIT FLOOR PLAN features the primary bedroom and bathroom on one side of the home and three additional bedrooms and a full bath on the other. High ceilings. BRAND NEW PUBLIX GROCERY STORE is being built less than five minutes away! Walking trail within the community to Chain of Lakes Elementary School. Call to schedule your private showing today.

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

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

Remarks: Welcome Home to Orchid Springs Village! Step into comfort with this inviting 1-bedroom, 1.5-bath condo located on the second floor of the peaceful Orchid Springs 55+ community. Surrounded by mature landscaping, this residence offers a quiet and comfortable setting, ideal for those looking to enjoy a relaxed Florida lifestyle. You’ll appreciate being conveniently close to shopping, dining, medical facilities, Winter Haven Hospital, US Hwy 27, and I-4. The monthly HOA fee covers water, sewer, trash, natural gas, lawn maintenance, grounds upkeep, and use of the community room, allowing for easy, maintenance-free living. An assigned parking space is included, and one pet is welcome with HOA approval (size and breed restrictions apply). Buyer approval is also required by the HOA. Whether you’re searching for a year-round home or a seasonal retreat, this well-maintained condo at Orchid Springs Village offers comfort, convenience, and a welcoming community atmosphere.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Scott Cohara (407-398-9554)

Remarks: Under contract-accepting backup offers. Welcome to 343 Sterling Drive in the well-established and well-loved Berryhill community of Winter Haven. This 3 bedroom, 2 bathroom home features a functional split floorplan and a wonderful opportunity for buyers looking to add their own cosmetic style and personal touches while enjoying several important updates already completed. Major improvements include replumbing throughout the home completed in 2016, new windows 2018, new roof in 2020, and a brand-new water heater in 2026 — providing peace of mind for many of the home’s major components. Step outside to enjoy the covered patio and private fenced backyard setting, offering a peaceful space for relaxing, entertaining, or enjoying quiet evenings at home. Berryhill is known for its established charm and convenient location with a very low annual HOA. Ideally situated near shopping, dining, medical facilities, and local attractions including LEGOLAND Florida Resort. This home combines comfort, value, and potential in one of Winter Haven’s convenient locations. Additional features include an interior laundry room and spacious two-car garage, adding everyday functionality and convenience.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Jessica Willaford (863-662-8549)

Remarks: **PRICE IMPROVEMENT** MAINTENCE-FREE LIVING...Located right in the Heart of Winter Haven at Imperial Villas, a 55+ community. This very well maintained 2 Bedroom/ 2 Bathroom Villa that offers a complete update, boasting tasteful renovations throughout. Being sold Fully Furnished! From the kitchen to the bathrooms, flooring to the roof, nearly everything has been thoughtfully upgraded. Step inside to discover new ceramic tile and luxury vinyl flooring that sets a modern tone. The kitchen showcases stainless steel appliances, granite countertops, ample cabinet and countertop space. Retreat to the owner's suite at the back of the villa, offering a beautifully tiled walk-in shower and a generous walk-in closet. Through the great room, step into to enclosed lanai. Updates include: Roof (2020), Electrical Panel (2023), HVAC (2012) & Tankless Hot Water Heater (2018). Residents of this community have access to a refreshing pool, making it perfect for leisurely afternoons. The low HOA fee of $270/month covers water, internet, cable, gas, trash and grounds maintenance, ensuring a hassle-free lifestyle. Conveniently located just a short walk from the picturesque Lake Howard and minutes away from downtown Winter Haven. You'll have easy access to charming shops, delectable restaurants, the historic Ritz Theater, and vibrant events like farmers markets in the park. Don't miss out on the opportunity to make this your new home. Schedule your private showing today and experience the epitome of Florida living!!

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

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

Remarks: Under contract-accepting backup offers. Welcome to 4717 Magnolia Preserve Ave, a beautifully upgraded home nestled in the desirable Magnolia Preserve community of Winter Haven. Built in 2016, this thoughtfully designed home features 3 bedrooms, 2 bathrooms, and a versatile formal dining room that can easily serve as a home office or potential 4th bedroom. Inside, you’ll find an open and inviting floor plan with high ceilings and an extended living area, creating a bright and spacious feel throughout. The kitchen is a standout, showcasing granite countertops, 44-inch cabinetry, stainless steel appliances, and a charming bay window that fills the space with natural light. A breakfast bar seamlessly connects the kitchen to the living area—perfect for entertaining or everyday living. The primary suite offers a true retreat with elegant tray ceilings, dual closets, and a well-appointed en suite bathroom featuring dual vanities and a relaxing garden tub. Step outside through the French doors to your covered patio and enjoy one of this home’s most sought-after features—a fully fenced backyard overlooking a peaceful, picturesque pond. Whether you're hosting gatherings or enjoying a quiet evening, this outdoor space delivers both privacy and a beautiful view. Perfectly positioned in Central Florida, this location offers the best of both worlds—convenient access to world-famous theme parks and an easy drive to Florida’s stunning Gulf and Atlantic beaches. With its ideal layout, scenic backyard, and convenient location, this home offers the perfect blend of comfort and Florida lifestyle living. Come see it for yourself—you won’t want to leave!

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

Listing Agent: Stephen Novak (863-409-3635)

Remarks: Short Sale. Welcome to your new home in this peaceful and well-maintained community! This spacious 2-bedroom, 2-bathroom condo offers comfortable, low-maintenance living with all the amenities you need to relax and enjoy life. Step inside to find a bright and open floor plan with generous living space, a well-equipped kitchen, and private bedrooms on opposite sides for added privacy. The primary suite includes a full en-suite bathroom and ample closet space, while the second bedroom is perfect for guests, a home office, or family. Enjoy your morning coffee on the screened in back patio or take a short stroll to the community clubhouse, where you’ll find a sparkling swimming pool, social spaces, and exclusive access to a private fishing area—perfect for outdoor enthusiasts. Nestled in a quiet neighborhood with beautifully landscaped grounds, this condo is ideal for those seeking comfort, convenience, and a touch of nature. Whether you're downsizing, investing, or buying your first home, this property offers a unique blend of tranquility and community living. Don’t miss this opportunity—schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Casandra Vann (863-546-5446)

Remarks: Stunning Masterpiece! This custom built 4 bedroom, 3 bathroom home with a den/office offers over 2.300 square feet of beautifully designed living space! From the moment you step inside, you'll be captivated by the open-concept floor plan and elegant wood-look ceramic tile flooring that flows seamlessly throughout the home. The spacious living room serves as the heart of the home, showcasing a striking recessed tray ceiling accented with rich wood detailing and triple-panel sliding glass doors that fill the space with natural light while providing easy access to the rear covered patio and fully fenced backyard. The chef-inspired kitchen is designed to impress, featuring crisp white shaker cabinetry, a contrasting center island, gorgeous stone countertops, a stylish tile backsplash, and a generous walk-in pantry. The thoughtfully designed split-bedroom layout offers privacy and comfort. The luxurious primary suite is a true retreat, complete with two walk-in closets and a spa-like bathroom featuring dual vanities and an oversized walk-in shower. The 2nd bedroom has its own ensuite bathroom with access to the rear patio. Outside, the brick paver driveway and attractive stone accents create exceptional curb appeal and make a memorable first impression. Schedule your appointment today and experience everything this remarkable property has to offer!

Listing is courtesy of: ASSOCIATE REALTY (863-618-4000)

Listing Agent: Chrissi Jasso (863-618-4000)

Remarks: One or more photo(s) has been virtually staged. Best deal in Garden Grove Oaks! 55 plus manufactured home in Garden Grove Oaks! One of the best values in the community given the size, price and condition. Quietly tucked away in the peaceful 55+ community of Garden Grove Oaks, this home in excellent condition with lots of valuable updating and a spacious interior easy living. This move-in-ready 2-bedroom, 2-bath home offers thoughtful updates designed for easy, low-maintenance living, including double-pane energy-efficient windows, luxury vinyl plank flooring, a brand-new water heater, extra wide driveway, covered carport, screened patio, and a workshop/storage space. Inside, the bright and open layout provides multiple comfortable living areas, including a welcoming family room, a sunny Florida room, and a dedicated dining area—perfect for everyday living or hosting visiting friends and family. The spacious kitchen features ample cabinetry, generous counter space, and all appliances included. The primary suite offers a peaceful retreat with a walk-in closet and private bath with walk-in shower, while the guest bedroom and second full bath are ideal for visitors. At the front of the home, a light-filled Florida room with bay windows creates the perfect space for morning coffee, a home office, or hobbies. Step out to the screened porch and enclosed workshop to enjoy Florida’s mild weather year-round. Residents of Garden Grove Oaks enjoy an active, well-maintained community with a swimming pool, spa, clubhouse, shuffleboard courts, community pond, RV and boat parking, and a full calendar of social activities—making it easy to stay as engaged or as relaxed as you choose. Located in the heart of Winter Haven, you’re surrounded by over 50 lakes, including the renowned Winter Haven Chain of Lakes, along with golf courses, parks, local restaurants, and nearby attractions such as LEGOLAND Florida Resort. Everyday conveniences—Publix, Aldi, Walmart, TJ Maxx, and medical facilities—are all just minutes away. A comfortable home, a friendly 55+ community, and a convenient Central Florida location—all at an exceptional value. Don’t miss this opportunity to enjoy the Florida lifestyle at Garden Grove Oaks.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Michael Stone (863-412-9733)

Remarks: Under Construction. Brand new, energy-efficient home available by Jul 2026! Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy and features a huge walk-in closet. 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: Under Construction. Brand new, energy-efficient home available by Jul 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home providing plenty of privacy and features a spacious walk-in closet and shower. 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: Picture yourself in this top-floor, 3-bedroom, 2-bathroom condo with a Sun/Florida room, nestled in the desirable Imperial Harbor community of Winter Haven. With easy access via an elevator, this is the peaceful 55+ retreat you’ve been searching for!Imagine waking up and enjoying a morning stroll to the private community dock on Lake Howard, where you can cast a fishing line or set off on a boat ride—and yes, boat docking is INCLUDED in your HOA dues! Spend your afternoons soaking in the heated pool, staying active in the fitness center, or playing a friendly round of shuffleboard or billiards. This is truly resort-style living at its finest. Centrally located only about 45 minutes to Tampa or Orlando.Step inside to discover a bright, open layout with a spacious kitchen, perfect for entertaining. The primary suite boasts a walk-in closet, while the additional bedrooms provide plenty of space for guests, hobbies, or a home office. Plus, the in-unit laundry closet comes equipped with a washer and dryer for ultimate convenience.Best of all, your water, basic cable, and internet are included, making for effortless, low-maintenance living. This is the dream lifestyle you deserve—schedule your private tour today and make it yours!

Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)

Listing Agent: Justin Cans (347-238-0790)

Remarks: Discover this must-see Ruby home. Included features: an inviting covered entry; a well-appointed kitchen offering 42" white cabinets, a walk-in pantry and a center island; an elegant dining room; a spacious great room; a lavish primary suite showcasing a generous walk-in closet and a private bath; a laundry and a 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 PRICING!! NEW INSTALLED ROOF, AC AND APPLIANCES, KITCHEN FAUCET JUNE 2026. Discover the potential in this charming 3-bedroom, 2-bath home nestled within a gated Winter Haven community. Offering 1,303 square feet, this property features a unique side-entry front door connected by a private walkway, creating added character and curb appeal. Enjoy the comfort of an established neighborhood with long-term residents and a welcoming community feel. Conveniently located just minutes from Walmart, shopping, dining, entertainment, and Legoland, this home offers both location and opportunity. Residents also enjoy access to the community pool. Priced to sell and ready for your personal touch!

Listing is courtesy of: NEWBERRY REALTY & DEV GRP INC. (321-607-2354)

Listing Agent: Gylwerd Sevilla Oviedo (305-989-7853)

Remarks: One or more photo(s) has been virtually staged. Beautifully renovated home in the heart of Winter Haven! Located 2.1 miles to LEGOLAND Florida Resort, this home is ideal as a primary residence, vacation home, or investment opportunity. Conveniently close to shopping, restaurants, and medical facilities, with easy access to everything Winter Haven has to offer. This move-in ready property features updated finishes throughout and offers the perfect combination of comfort and convenience. Enjoy a large fenced backyard with plenty of space for entertaining, pets, or outdoor activities. Don’t miss your chance to own this charming home in a prime location!

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

Listing Agent: Twinkle Robinson (863-860-6645)

Remarks: Welcome to modern comfort in the heart of Winter Haven! This meticulously maintained 4-bedroom, 2-bathroom home is a move-in-ready living space. The residence features a bright, open-concept floor plan with a seamless flow between the kitchen and living areas, complemented by durable tile and laminate flooring. Enjoy outside living in your private fenced in backyard or sit on the enclosed patio and enjoy the outdoors. Florida living at its best!

Listing is courtesy of: SPANN & ASSOCIATES REAL ESTATE (407-468-7512)

Listing Agent: Kal Scarvers (863-617-5236)

Remarks: ARE YOU LOOKING FOR A GATED COMMUNITY WITH A LOW HOA and NO CDD? At 116 Mandolin Dr in WINTER HAVEN, FL! This spacious 4-bedroom, 2-bathroom home offers 2,248 square feet of COMFORTABLE LIVING on a generous 0.26-acre lot! Step inside to soaring VAULTED CEILINGS in the living and dining areas—these ELEVATED CEILINGS create an open, airy feel that makes the home even larger than its footprint. The entire home features durable VINYL FLOORING, and all bedrooms are generously sized, offering FLEXIBILITY FOR FAMILIES, guests, or a home office. NATURAL LIGHT pours in throughout the home, creating a bright and welcoming atmosphere that’s perfect for new homeowners. Major updates include a NEW A/C SYSTEM (2025) and GUTTERS INSTALLED (2024), while the WATER HEATER was replaced in 2017. The roof and plumbing are original, but the seller is willing to NEGOTIATE A BRAND NEW ROOF — making this property an UNBEATABLE VALUE for the price. Situated in a quiet gated community, this property offers both privacy and security. The location is a standout—just a short walk from a newly constructed Publix set to open in the coming months, as well as nearby Dollar General and 7-Eleven for everyday convenience. You’re also just minutes away by car from Eagle Ridge Mall, LEGOLAND Florida Resort, and all the shopping, dining, and entertainment that downtown Winter Haven has! —making this home not only comfortable, but perfectly located.

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

Listing Agent: Nomar Rosa (646-673-3900)

Remarks: One or more photo(s) has been virtually staged. Welcome to 6775 Brentwood Dr NE, located in the desirable no pet community of Lake N Golf Estates, a 55+ lakefront community offering the best of Florida living. This well maintained, mostly furnished home offers 3 bedrooms, 2 bathrooms with a spacious and functional layout, including a Florida room, formal dining room, breakfast nook and a dedicated laundry/storage room, providing plenty of flexibility for everyday living and entertaining. Updated HVAC system (2024) & automated thermostat. Additional exterior features include awnings for added shade and energy efficiency, along with a spacious carport for convenient covered parking. The home already passed the insurance/4-pointe inspection & will come with a one year home warranty at closing. It is situated within an established, beautifully maintained community known for its welcoming atmosphere & convenient access to nearby shopping, dining, medical facilities, and major roadways. Residents of Lake N Golf Estates enjoy fantastic amenities including a clubhouse, heated pool, spa, shuffleboard courts and community boat slip access, perfect for taking full advantage of the scenic lakefront setting. With OWNED land, low maintenance living, this community offers both comfort & peace of mind. Whether you're looking for a seasonal retreat or a fulltime residence, this is a wonderful opportunity to enjoy the Florida lifestyle at its finest. Schedule your private showing today and experience all that Lake N Golf Estates has to offer!

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

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

Remarks: One or more photo(s) has been virtually staged. Welcome to 23 Casarena Ct in Winter Haven, located in the gated lakefront community of Casarena on the Lakes on Lake Cannon, part of Winter Haven's Chain of Lakes. This spacious 2BR/2.5BA townhome that offers approximately 2,045 sq ft of living space with vaulted ceilings, abundant natural light, and a functional two-story layout. The main level features an open living area with sliding glass doors leading to a private covered patio, plus a well-appointed kitchen with a breakfast bar and a convenient half bathroom. Upstairs, enjoy a versatile loft/bonus space ideal for a home office or additional living area. Both bedrooms offer ensuite bathrooms, including a primary suite with a private screened balcony. Additional highlights include ceramic tile & hardwood flooring, spacious bedrooms, a two-car garage with freshly painted floor & multiple outdoor spaces including three patios. Recent updates include the ROOF (Aug 2023). Owner is offering a $5,000 credit towards flooring. Residents enjoy resort style amenities: community pool, tennis courts, boat slip & dock with direct access to Lake Cannon and the Chain of Lakes, perfect for boating, fishing, and waterfront living. Prime location near shopping, dining and major roadways. Low-maintenance living in a secure, gated community.

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

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

Remarks: MOVE-IN CONDITION! Charming 2-bedroom, 2-bath patio home on a shaded, landscaped corner lot in Cypresswood Golf & Country Club. This well-maintained single-level residence features a split-bedroom floorplan, expansive great room for living and dining, breakfast nook, carpet and tile floors, skylight, ceiling fans, ample closets including a walk-in in the primary, and a convenient attached 2-car garage with attic access. Enjoy an oversized screened rear porch overlooking picturesque greenspace and mature oaks. Systems and amenities include architectural shingle roof, gas water heater, and full kitchen appliances (dishwasher, range, microwave, refrigerator, washer/dryer). HOA includes community pool and private road; community amenities include an 18-hole golf course, clubhouse with pro shop and lounge, Jr. Olympic pool, tennis/pickleball/recreation area. Convenient to HWY 27, I-4, shopping, restaurants and near Publix.

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

Listing Agent: Michelle Howard (863-944-9920)