Winter Haven Homes For Sale & Real Estate - 863 homes

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Indigo - 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. 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: Welcome to your perfect slice of Florida living! This solid concrete block home combines durability, comfort, and modern updates - making it an exceptional opportunity whether you're searching for your next residence or an investment property. Step inside to discover brand-new vinyl plank flooring that flows beautifully throughout, complemented by newer stainless steel appliances that bring a fresh, modern feel to the home. Major systems have already been taken care of for you, including a 2022 HVAC system and 2022 water heater, plus a metal roof installed in 2012 for long-term peace of mind. Outside, enjoy a fully fenced yard - perfect for pets, entertaining, or simply relaxing under the canopy of mature shade trees. The carport and additional parking pad provide plenty of space for vehicles, guests, or even a boat. Nestled in an established neighborhood, this home offers the rare advantage of NO HOA or CDD fees, giving you both freedom and affordability. You'll love the convenient location - just minutes from lakes, parks, shopping, and vibrant downtown Winter Haven. Whether you're looking to settle in or invest, this property checks all the boxes. Don't miss your chance to own this move-in-ready gem - schedule your private showing today before it's gone!

Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)

Listing Agent: John Evans (813-992-3483)

Remarks: Welcome to 960 Wedgewood Dr SE, a one-owner, mid century ranch home offering over 2,300 square feet of living space with original vintage character, ideally situated on a spacious ¼+ acre cul-de-sac lot with no HOA. This 3-bedroom, 2-bath residence offers a functional and inviting layout with formal living and dining rooms, with the dining room offering flexibility as a potential 4th bedroom thanks to its walk-in closet. The large formal living room provides ample space to host many guests and creates the perfect setting for intimate gatherings and conversation while the comfortable family room features a brick wood-burning fireplace surrounded by built-in shelving and cabinetry, creating a warm and welcoming focal point. The kitchen is generously sized with wood cabinetry, abundant counter space, ample storage, and a closet pantry—ready to serve as the heart of the home. The primary suite includes an en-suite bath with an updated walk-in shower and a spacious walk-in closet. Two additional bedrooms provide plenty of space for family or guests. A secondary bath with a tub is conveniently located by the bedrooms and the hallway features two linen closets, offering great storage throughout the home. A front bonus room creates a welcoming entry and is perfect for a piano or flex space. Additional highlights include a screened rear lanai ideal for morning coffee or entertaining, a charming covered front porch, a fenced backyard, and a storage shed with built-in shelving. The home is equipped with two A/C units plus a mini-split in the primary bedroom, allowing you to keep the home extra cool during Florida’s summer months. The oversized two-car garage offers built-in shelving, a storage closet, washer and dryer, and attic access via pull-down stairs for additional storage. Additional features include rain gutters, a separate irrigation water meter, and a location on a dead-end road with minimal traffic, offering added privacy and quiet enjoyment. Major updates have already been completed, including a new electrical panel and breakers (2024), partial re-plumbing (2021), roof (2016) with 50-year shingles, A/C units (2015 & 2018), and a natural gas water heater (2016). With new flooring and cosmetic updates, this home offers the perfect opportunity to create a charming and beautiful space to enjoy for years to come. Conveniently located just minutes from Publix, restaurants, schools, medical facilities, and LEGOLAND Florida Resort, with easy access to both Tampa and Orlando, offering quick trips to world-class theme parks and Florida’s east and west coast beaches. Located on a highly sought-after street, this is a rare opportunity to purchase a well-built home with great bones, space, and location—ready for its next chapter.

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

Listing Agent: Deanna Stone (863-412-2080)

Remarks: Spacious and well-maintained 4-bedroom, 2-bath home with a private pool, offering 2,160 square feet of living space on an oversized 0.24-acre lot. Inside, vaulted ceilings create an open, airy feel throughout the main living areas, enhancing both natural light and functionality. The home also features a brand new HVAC system for added peace of mind. Step outside to a generous backyard with plenty of space beyond the pool to relax, entertain, or customize to your needs. Located in Winter Haven, this property offers convenient access to major roadways, shopping, dining, and the area’s well-known chain of lakes, making it easy to enjoy both everyday living and weekend recreation.

Listing is courtesy of: SOUTH CEDAR REAL ESTATE, INC (813-374-7907)

Listing Agent: Caylee Decleene Llc (920-639-2241)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Investor Opportunity – Prime Land in Growing Polk County This 1966 mobile home is a complete tear-down, offering a valuable opportunity to build new. The true value is in the land. Located in one of the fastest-growing areas in the U.S., this property is ideal for investors or builders looking to capitalize on new construction potential. New builds in the area are selling for approximately $250,000+. Key Highlights: Impact fees already paid (a savings of over $14,000 in Polk County) Public water in place Existing septic system Estimated land value: ~$60,000 Whether you're looking to build and resell or hold for future appreciation, this is a solid investment opportunity. Don’t miss your chance to secure land in a high-growth market.

Listing is courtesy of: REALTY HUB (407-900-1001)

Listing Agent: James Sparkman (352-789-3865)

Remarks: Minutes from Legoland and Peppa Pig Theme Park, this 5-bedroom, 3-bath home offers comfort and functionality in a quiet cul-de-sac. The open-concept layout features a spacious kitchen, main-floor den, and a first-floor guest suite with full bath. Upstairs includes a versatile loft and a primary suite with walk-in closet and dual vanity. Additional highlights include second-floor laundry, tile in wet areas, a 2-car garage, and a large backyard ideal for entertaining. Conveniently located near shopping and dining. Low HOA—perfect for first-time buyers or investors. (Tenant Occupied - Lease ends October 2026)

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

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

Remarks: FIXER-UPPER OR INVESTORS. Priced accordingly. 2 Bedroom 1 bath- Excellent for rental property. Attached carport and large back yard. NO HOA! Located close to schools, churches, and shopping. Cash offers only with buyer paying title insurance and doc stamps.

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

Listing Agent: Sharon Watson (863-557-4800)

Remarks: Under Construction. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5 miles from public lake access at Lake Daisy, ideal for a day of boating, paddle boarding, and enjoying the water. The Panama single-family home is what you always pictured for yourself. Step in from your 2-car garage or front porch and pass the first of 4 spacious bedrooms and a full bath with double vanity. In your dining area, prepare to be wowed. This space is highlighted by a gourmet kitchen with a large island overlooking your lanai and a great room where friends and family will gather. Your luxurious owner’s suite includes a double vanity owner’s bath and a huge walk-in closet. Your second-story bonus room is the perfect space for a home office, playroom or guest suite. You can have it all with the Panama. 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 Brandy Chase Village!! This well desired 55+ community located in Winter Haven Florida is centrally located between Tampa and Orlando. The beautiful 2 bedroom and 2 bathroom home is well maintained and ready for you! Enjoy your oversized sunroom that adds extra square footage of living space for you to enjoy. Updated appliances and a new AC was installed in 2021 , as well as it was replumbed in 2021. Assigned covered parking space with additional guest parking spot. Are looking for a new primary residence , to downsize or a winter getaway? Either way you will not be disappointed with everything this property offers. Beautiful grounds and low cost HOA fee which includes water/sewer, garbage,lawn care, clubhouse and pool maintenance. Minutes from the Polk Parkway and the neighboring cities of Lakeland , Auburndale and Bartow this is the perfect location for you! Call today for your showing , don't miss out on your opportunity to call Brandy Chase your home!

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

Listing Agent: Rosalia Abreu (954-854-3694)

Remarks: Under contract-accepting backup offers. Pending accepting backup offers… Opportunity and location all in one! Situated on a corner lot with just under a quarter of an acre, This property is just 15 minutes from LEGOLAND , 45 minutes to DISNEY and walking distance to Lake Ship Park, making it perfect for enjoying everything the city of Winter Haven, The home features a detached workshop—ideal for hobbies, storage, or a workspace—and a separate area to make in-law suite with its own bathroom, giving you flexibility for guests, extended family, or potential rental space. The suite just needs a little updating to make it your own. Whether you're looking for a primary home with extra space, an investment opportunity, or a property you can customize, this one has tons of potential. Don’t miss out on this hidden gems with so much potential to make this your own nest.

Listing is courtesy of: EXP REALTY LLC (407-392-1800)

Listing Agent: Bonnie Huntsman (407-230-2443)

Remarks: This beautifully maintained 2,041 sq ft home is located in the desirable Villamar community. The open-concept floor plan features a spacious gathering room that flows into the dining area and well-appointed kitchen complete with crown molding, granite countertops, stainless steel appliances, shaker-style cabinets, breakfast bar, and walk-in pantry. The private owner’s suite offers a tray ceiling, large walk-in closet, and spa-like bath with dual vanities, garden tub, tiled shower, and private water closet. Luxury vinyl plank flooring enhances the main living areas, with stain-resistant carpet in the bedrooms. Additional features include a Jack-and-Jill bath, guest powder room, drop zone at garage entry, faux wood blinds, built-in pest control, architectural shingles, and energy-efficient upgrades including R-30 insulation and Low-E tinted windows. Enjoy outdoor living on the covered lanai overlooking beautifully maintained, Florida-friendly landscaping with irrigation. The community resort-style pool is perfect for relaxing in the Florida sun.

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

Listing Agent: Pamela Carter (863-412-4795)

Remarks: Welcome to this 2-bedroom, 1.5-bath condo in the desirable 55+ community of Winter Haven Harbour Apartments! This beautifully updated unit is modern, stylish, and completely move-in ready. Inside, the condo has been freshly painted and features luxury vinyl plank flooring in living areas and tile in kitchen and baths. Both bathrooms have been fully redone with modern finishes. The main bath features granite countertops and a stand-up shower with a built-in seat for added comfort and accessibility. The updated kitchen offers ample cabinetry and storage, Granite counter tops, plus the added bonus of a washer and dryer all-in-one unit — a huge perk for condo living. Important updates include a 2021 water heater and all new storm windows installed last year. An additional bonus is the private storage closet located next to the elevator; approximately 4x6 feet with floor-to-ceiling space. This active 55+ community offers a welcoming community center complete with a fitness center, library, and pool table. Outside near the heated pool, you’ll find a beautiful friendship garden with seating and a fire pit — the perfect spot to relax or gather with neighbors. Residents also enjoy pickleball courts, shuffleboard, and a grilling area ideal for social events and sunny Florida afternoons. Conveniently located near shopping, dining, medical facilities, and positioned between Tampa and Orlando. If you’re looking for updated, modern living in a vibrant and friendly 55+ community, this top-floor gem checks all the boxes. Schedule your private showing today!

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

Listing Agent: David Small (407-601-8351)

Remarks: SELLER OFFERS $10,000 CREDIT TOWARD CLOSING COSTS OR UPGRADES, BUYER’S CHOICE PRIOR TO CLOSING! Welcome to this charming 3-bedroom, 2-bathroom home in Winter Haven, offering an open and functional layout perfect for everyday living and entertaining. This solid single-family residence features approximately 1,449 sq. ft. of comfortable living space, including a cozy living/dining combination and a well-appointed kitchen. The property boasts significant recent upgrades, including: - Roof: Installed in 2021 - HVAC: Brand new A/C system, ducts, and air handler installed one year ago - Water Heater: Only 3 months old - Flooring: Brand new tile throughout the entire home Outside, you will find a large fenced backyard providing ample room for gardening, play, or weekend grilling. Ideally located on a quiet residential street, this home is just minutes from shopping, dining, major highways, local attractions, and Legoland. With no HOA, this home is an excellent opportunity for first-time buyers, those looking to downsize, or investors seeking value and convenience. Don’t miss out on this Winter Haven gem!

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

Listing Agent: David Small (407-601-8351)

Remarks: HERONS, CRANES, EGRETS, AND DUCKS! You'll have a birds eye view of Florida's most beautiful waterfowl from this custom 3 bedroom 3 bath home located in charming Vienna Square. This excellent floor plan offers a private 3rd bedroom with en suite bath perfect for the momma, in-laws, or extra guests. Enjoy the private interior courtyard with an in-ground spa, and space for fun get togethers. Check out the upgraded wood cabinets pull outs, granite countertops, 7 foot doors, elaborate crown molding, and deep wood trim throughout this well planned home. This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a fun filled lifestyle with reasonable fees, in a welcoming setting. Vienna Square is a beautifully maintained, amenity-rich community designed for retirement living. Monthly fees include lawn mowing, a Spectrum Internet/TV package, and all community amenities. Residents enjoy access to a community pool, fitness center, billiards, movie nights, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!

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

Listing Agent: Marti Sutton (863-206-0563)

Remarks: Under contract-accepting backup offers. Priced to Sell! -A fantastic opportunity awaits the buyer looking for a quiet neighborhood with plenty of outdoor space and wide-open views from the back of the property. Welcome home to this spacious 3-bedroom, 2-bathroom double-wide mobile home, designed for comfortable living and maximum storage. The functional floor plan includes two screened-in porches, one at the front and one at the back, offering a seamless transition between indoor and outdoor living. A practical carport protects your vehicle from the elements, while the detached one-car garage, complete with extra storage, is perfect for a workshop or housing your toys. This double-wide mobile home sits on just over a quarter acre and offers a generous footprint, ready for your personal touch. With a little vision, you can transform this property into your dream home and build instant equity.

Listing is courtesy of: JULIE CLARK REAL ESTATE (863-944-2772)

Listing Agent: Janet Harrison (863-712-0606)

Remarks: Under contract-accepting backup offers. Short Sale. BANK APPROVED AT 263K --VACANT---ON A CORNER LOT--delightful home boasting a private vinyl fenced side and backyard. Step inside to find three bedrooms and two bathrooms, where the primary suite offers serene privacy and comfort. The kitchen is a homeowner’s dream with upgraded granite countertops, complemented by stylish brown cabinets. Hard flooring flows throughout most of the home, providing both beauty and durability, while the cozy carpet in one guest bedroom offers a touch of warmth. Freshly painted walls and even the ceiling fan in the family room have just been updated, giving the whole space a fresh, inviting feel. Additionally, a covered lanai provides a perfect spot for relaxation or entertaining. Easy access to the Polk Parkway to Orlando And Tampa,

Listing is courtesy of: PREFERRED RE BROKERS III (407-440-4900)

Listing Agent: Michael Huculak (321-624-0150)

Remarks: Lake Ashton is a 55+ golf community with all the amenities you could ask for including movie theatre, bowling alley, pickle ball, tennis, bocce, fitness centers, two clubhouses and so much more! This highly upgraded 3-bedroom, St John floor plan home is breathtaking! Once inside the elegant beveled double French glass door entry you will be amazed at the impeccably executed home finish. Such as, round columns frame the dining area, while raised archways lead to the kitchen and breakfast nook. The great room features coffered ceilings with recessed lighting, 8’ triple sliders that open to the lanai, a ceiling fan, and 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, granite countertops, pendant lighting, and a breakfast bar. This home has split plan for privacy. 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. The large, screened lanai overlooks the 13th hole has pond and nature views. There is also the Health and Fitness center which has an indoor pool, sauna, racquet ball and basketball, for your enjoyment. There are so many more amenities, clubs, activities, dances, and entertainment. Don't miss out on the opportunity to live in Lake Ashton, Central Florida's premier 55+ active adult resort style living community. This is a must see to appreciate home and community! SELLER MOTIVATED!!!

Listing is courtesy of: HEROES REAL ESTATE GROUP LLC (407-947-6420)

Listing Agent: Armando Perez (407-947-6420)

Remarks: Welcome to this refined sanctuary where timeless elegance meets Florida’s tranquil landscape. On a premium golf-adjacent lot within the guarded, gated community, 2964 Plantation Road blends gracious scale, luminous living and multi-generational flexibility in one seamless layout. Upon arrival, you are greeted by mature landscaping, a circular drive and side-entry access to a three-car garage, with stunning views of golf course fairways and water views. Enter inside to discover over 3,600 square feet of thoughtfully designed space. Formal living and dining rooms flow with grace and purpose, while a custom wet bar offers effortless entertaining. The split floor plan is crafted for privacy and connection. The primary suite is complete with dual vanities, walk-in closets, a garden tub, separate shower and private pool access. On the opposite wing rests an en-suite bedroom, complete with full bath and independent access. Ideal for multigenerational living, guest privacy or an upscale in-law suite. Two additional bedrooms share a Jack and Jill bath, while a half bath serves daily living or poolside use. Gourmet gathering begins in the kitchen including a center island with gas range, generous counter space and views out toward the lanai. The breakfast nook offers a comfortable space for everyday dining, complemented by a nearby utility room and a flexible bonus room. Going outside, this home’s soul lives in its outdoor realm. A pool and spa, and a summer kitchen complete with built-in grill, sink and prep station, invite all-day alfresco living. A covered lanai frames those golf and pond vistas beautifully, offering shade and breeze for lounging or entertaining. Cypresswood is a full-amenity, guard-gated community with an 18-hole golf course, clubhouse with restaurant and lounge, tennis and pickleball, fitness/wellness center, and social programming. $10,000 seller concession and Home Warranty.

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-480-5014)

Listing Agent: Audrey Christman (516-547-5343)

Remarks: PRICE REDUCTION!! Very well kept home on your own lot. No lot rent here! Low HOA of only $65 a month. Garden Grove Oaks is a well-kept and managed over 55 park in a great location in SE Winter Haven. Home has 2 bedrooms and 2 full bathrooms. Kitchen and dining area have tons of cabinets and storage for all your dishes and cookware and includes a closet pantry. There is a wet bar in the dining area with a small sink, open shelves and cabinet storage underneath. The opposite side of the dining room has a built-in china cabinet. Main bedroom is a great size with a walk-in closet and small bathroom with tub and tiled shower. Second bedroom has door opening to nice-sized bathroom with large sink and cabinets and a shower/tub combination. Home has a membrane roof that was installed in spring of 2014. York air conditioner is 8-9 years old. Nice large laundry room has Bosch washer and dryer. Back screened porch is always cool! HOA fee includes use of the clubhouse with many activities planned every month. There is a billiard room, card and game room with library and puzzles to check out, large event area, and great kitchen. Huge heated pool and spa for all residents and their guests. There is a screened-in area with a grill for Bar-B-Q's with family and friends. There is also a shuffleboard court. HOA is an award-winning association. Community is close to a Super Walmart and grocery stores as well as shopping and restaurants. Only minutes to Hwy. 27! Winter Haven is famous for its Chain of Lakes! Where else can you find all of this for only $137,900? Please make an appointment to see this great home today!

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

Listing Agent: Peggy Lewellen (863-412-7692)

Remarks: Take a look at this beautifully upgraded 3-bedroom, 2-bathroom home located in the desirable gated community of Sanctuary by the Lake in Winter Haven. Nestled along the shores of Lake Rochelle part of the renowned Chain of Lakes this property offers the perfect blend of comfort, style, and serene lakeside living. Step inside to an inviting open-concept layout featuring a bright and spacious living and dining area with glass sliding doors that overlook a large, fully fenced backyard. With plenty of room to add a pool, the outdoor space is ideal for relaxation and entertaining. A double-car garage provides ample parking and additional storage. The modern kitchen is designed for both functionality and style, boasting stainless steel appliances, rich wood cabinetry, a spacious pantry, and a large island perfect for casual dining and gatherings. The primary suite serves as a private retreat, complete with an oversized walk-in closet and a luxurious en-suite bathroom featuring a walk-in tiled shower. Two additional bedrooms bring comfort and versatility for family, guests, or a home office. Residents of Sanctuary by the Lake enjoy exclusive access to Lake Rochelle for kayaking and water sports, as well as scenic walking trails, private docks, and a playground. All of this comes with low HOA fees and no CDD. Conveniently located near shopping, dining, medical centers, and major attractions including LEGOLAND®, Walt Disney World®, and Universal Studios® this home offers the best of Central Florida living.

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

Listing Agent: Gaby Murillo (863-668-1914)