Winter Haven Homes For Sale & Real Estate - 1041 homes

Remarks: Welcome to your own slice of paradise! Set on a picturesque lot with serene water views, this stunning pool home offers the lifestyle buyers dream about. Enjoy morning coffee overlooking the water, afternoons by the sparkling screened pool, and evenings entertaining on the expansive lanai. Designed for both relaxation and gathering with family and friends, this home seamlessly blends indoor comfort with exceptional outdoor living. Located in one of Winter Haven's established communities, you'll enjoy the perfect balance of peaceful surroundings and everyday convenience. This is more than a home—it's a lifestyle. Highlights include: Private screened swimming pool Spacious covered lanai for outdoor entertaining Well-maintained home with inviting living spaces Desirable Winter Haven location Convenient access to shopping, dining, and recreation Ideal for enjoying the Florida lifestyle year-round **Home is currently on AirBnb so showings are limited based on bookings ** FREE Incentive: Sellers preferred lender offering a 1-0 temporary rate buydown and/or lender credits up to 1 point for qualified buyers.

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

Listing Agent: Brooke Bass (813-763-7103)

Remarks: Under Construction. Open flow sets the tone for this elegant new Crestone II two-story townhome. There are a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

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

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

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: Don't miss this move-in ready, recently updated 3 bedroom, 2 bathroom block home with a 2-car garage, situated on a spacious 7,370 sq ft lot in Winter Haven. This 1994 built home features a recently remodeled kitchen with quartz countertops, shaker cabinets, stainless steel appliances, luxury vinyl plank flooring, updated bathrooms, and fresh paint throughout! Major components like the roof and A/C have both been updated in recent years, with plenty of life remaining for added peace of mind. The open living room features a shiplapped fire place. Out back, enjoy the newly installed paver patio, perfect for grilling, relaxing, or entertaining in the spacious yard. This is a great value for a well-updated home with both indoor and outdoor space at an affordable price point with a low HOA! FHA and VA friendly! *Some photos have been virtually staged*

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

Listing Agent: Philip Bach, Pa (786-351-2294)

Remarks: 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: Attention investors, landlords, and value-add buyers! Opportunity knocks at 132 Longfellow Rd in SE Winter Haven. This block home offers approximately 1,470 square feet with 2 bedrooms, 1.5 baths, a spacious lot, and strong upside potential. Located in an established neighborhood close to shopping, restaurants, schools, and major commuter routes, this property presents an excellent opportunity for renovation, rental hold, or resale. The seller is seeking the strongest offer and intends to review all offers submitted within the first 10 days on market. Cash buyers, investors, and buyers looking for a project are encouraged to take a look. Whether you're expanding your rental portfolio, looking for your next flip, or searching for a value-add property in a desirable Winter Haven location, this is one you'll want to evaluate quickly. Property is being sold as-is. Schedule your showing today and submit your highest and best offer before the review period ends.

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Chad Lindsey (863-660-7837)

Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 6053 Southern Oaks Drive SE in the highly desirable Garden Grove Oaks, a friendly 55+ community where you own your land—no lot rent! This beautifully maintained and fully furnished 2-bedroom, 2-bath home offers 1,104 square feet of comfortable living space, plus an additional 190-square-foot Florida Room featuring all-new windows, creating the perfect spot to relax, entertain, or enjoy your morning coffee. The bright, inviting interior features an inside laundry room and comes complete with new kitchen appliances, making this home truly move-in ready. Major updates provide peace of mind, including energy-efficient windows installed throughout the home in 2020, a new water heater (2022), insulated Florida room roof update (2023), A/C replaced in 2019, and a roof installed in 2016. Whether you're looking for a year-round residence or the perfect Florida retreat, this home offers low-maintenance living in one of Winter Haven's most sought-after active adult communities. Garden Grove Oaks features a clubhouse, heated pool and spa, shuffleboard, and a full calendar of social activities—all with a low HOA and the added benefit of land ownership. Conveniently located near shopping, restaurants, medical facilities, golf courses, and major highways, this home is ready for you to start enjoying the Florida lifestyle.

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Anita Lowe (863-269-6461)

Remarks: Virtually Staged. Move-In Incentive Available! Qualified buyers who finance with our affiliated lender may choose one of the following: a 4.5 interest rate or $5,000 toward closing costs (buyer must qualify; incentive applies only when using our affiliated lender). Welcome to this stunning 3-bedroom, 2.5-bath two-story home located on a quiet cul-de-sac in the desirable Lake Lucerne II community. Built in 2024 and beautifully enhanced with thoughtful upgrades, this home offers the peace of new construction with the added value buyers are looking for. The backyard is truly a showstopper, featuring a screened enclosure and backing up to conservation land with a serene pond view, creating the perfect setting to enjoy your morning coffee or unwind at the end of the day. Vinyl fencing along the sides and a rear metal fence preserve privacy without obstructing the view. Inside, the home features high ceilings throughout, luxury vinyl flooring (with carpeted stairs and tile in bathrooms and laundry), an open-concept floor plan, and elegant design touches including a detailed foyer wall and a charming electric fireplace in the living room. The upgraded kitchen boasts stone countertops, beautiful cabinetry, stainless steel appliances, a large island with bar seating, and a pantry, making it ideal for both everyday living and entertaining. Downstairs also includes a flex room perfect for a home office or guest space, a half bath, and a 2-car garage. Upstairs, a spacious loft offers endless possibilities, family room, playroom, or potential 4th bedroom. The primary suite is a true retreat, featuring tray ceilings, generous space for a king-sized bed, and an upgraded California Closet–designed walk-in closet offering exceptional storage and organization. The primary bath includes dual sinks and a walk-in shower. Two additional bedrooms, a full bath, and a well-appointed laundry room with sink complete the upper level. Additional upgrades include a whole-home water filtration system, security system, and a hybrid heat-pump water heater that efficiently heats water while cooling the garage. Enjoy resort-style living with no CDD, a community clubhouse, two pools, and a playground. Conveniently located near shopping, golf courses, and with easy access to I-4, you’re perfectly positioned between Orlando and Tampa, sunrise to sunset. This home is move-in ready and truly special. Schedule your private showing today and experience it for yourself.

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

Listing Agent: Luisa Hurtado (646-259-1153)

Remarks: NEW LISTING IN CENTRAL FLORIDA. CONDO IN 55+ Gated Community. This condominium provides 1.347 SF of living area 2 bedrooms, 2 baths, Bonus room with views of Spring Lake & is located in the beautiful City of Winter Haven. Lakeridge Condominiums offers a maintenance free lifestyle with heated pool, tennis, shuffleboard, community room, gated secured entrances and covered assigned parking space. Water, sewer, cable, internet, trash removal and use of recreational facilities are included in the monthly fee. This well appointed move in ready condo has a large bright kitchen with lots of cabinets, great counter space, appliances and pantry closet. The kitchen overlooks the great room that also adjoins the additional bonus area and storage closet. The primary bedroom has a walk in closet & bathroom with a walk in shower. Beautiful views of Spring Lake can be enjoyed from the Primary bedroom & living areas. Washer/Dryer are included. Convenient to shopping, groceries & restaurants. Extra assigned storage bin on same floor. Lakeridge Condominiums is an age restricted, well maintained & well managed community.

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

Listing Agent: Lisa Simpson (863-412-0393)

Remarks: Welcome to 255 Haines Boulevard, Winter Haven, Florida! This beautifully maintained home offers the perfect blend of comfort, convenience, and Florida living. Featuring a spacious floor plan with plenty of natural light, this property is ideal for families, first-time homebuyers, or investors alike. The kitchen provides ample cabinet and counter space and flows seamlessly into the living and dining areas, making it perfect for entertaining guests. Step outside and enjoy the generous yard with room for outdoor activities, gardening, or future enhancements. Conveniently located near shopping, dining, schools, medical facilities, and major roadways, this home provides easy access to everything in Winter Haven. Whether you're looking for a primary residence, seasonal home, or investment property, this move-in-ready opportunity is one you won't want to miss. Schedule your private showing today!

Listing is courtesy of: LAND SOUTH REALTY, LLC (863-937-8867)

Listing Agent: Sean Denney (863-602-0424)

Remarks: Welcome home to this stunning lakefront 4-bedroom, 2-bath retreat on Lake Hamilton featuring a courtyard outside along with lake views from both the sitting areas and the dining rooms inside of the home. The rooms are spacious, ideal for everyday living and remote work. Whether you're hosting, friends, enjoying family meals, or taking in the scenery after a long day. Spending mornings with coffee, enjoy evenings outdoors, or entertain with ease that comes from a deck right where you want to be, overlooking the lake lifestyle. The community is located near daily conveniences, including shopping, dining, and nearby attractions such as Legoland. From the first look at the views to the comfort of this home, this lakefront home is ready to be enjoyed. Don't miss the opportunity to own a home with lake views in multiple living areas and the added benefit of a deck for outdoor relaxation.

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

Listing Agent: Marquita Smith (863-289-3343)

Remarks: Prime opportunity in Winter Haven — this is primarily a land value play. The lot features an older 1950 wood-frame home in need of significant work, giving buyers two clear paths forward: fully renovate the existing structure or clear the lot and build new. A new single-family home on this site carries an estimated ARV of $260,000, making this an ideal project for investors, builders, or renovators looking to add value in a growing area. Sold as-is — bring your vision and your contractor.

Listing is courtesy of: REI BROKERAGE HOUSE, INC. (813-389-7881)

Listing Agent: Shalimar Santiago (813-389-7881)

Remarks: Welcome to this spacious home Located in the gated community of The Gardens, this spacious 4-bedroom, 2-bath home offers an open layout designed for comfortable living and entertaining. The large primary suite features a tray ceiling, two walk-in closets, dual sinks, a tile shower, and a garden tub. Step outside to enjoy a generous backyard with an outdoor kitchen/BBQ area, above-ground pool, storage shed, and plenty of room to relax or entertain.

Listing is courtesy of: ORCHARD BROKERAGE, LLC (844-515-9880)

Listing Agent: Ray Garza (407-607-9382)

Remarks: CALLING ALL INVESTORS!! Amazing opportunity with a blank canvas to be creative! This property boasts 2 separate dwellings, both with living spaces, kitchens, dining areas, 2 bedrooms and 1 bathroom WITH an in ground pool in between! Property also has a THREE car garage AND a huge open space in the attic with stair access from a bedroom! Direct view and access to Lake Cannon, WOW!! Make your appointment today to secure this amazing opportunity! CASH ONLY, BEING SOLD AS IS.

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

Listing Agent: Veronica Davis (863-326-8001)

Remarks: Tucked away on a low-traffic cul-de-sac in Cedar Cove, this well-maintained home offers something increasingly difficult to find in today’s market: space, privacy, mature shade trees, and room to enjoy the Florida lifestyle. Situated on an oversized 11,835 sq ft fenced homesite (more than a quarter acre) the property stands apart with a peaceful setting and a spacious backyard shaded by towering oak trees that provide character and beauty years in the making. Whether entertaining, gardening, relaxing, or simply enjoying extra outdoor space, this property offers flexibility that is becoming harder to find. VALUE, CONFIDENCE, AND PEACE OF MIND ARE BUILT IN. With an acceptable offer, the seller will provide a NEW ROOF prior to closing, and a NEW WATER HEATER has already been installed. A Wood Destroying Organism (WDO) report, Four-Point Inspection, and Wind Mitigation Report are also available for buyer review. Conveniently located near shopping, dining, medical facilities, schools, LEGOLAND Florida Resort, and major routes connecting Tampa and Orlando, this home offers an exceptional combination of convenience, outdoor living, and everyday comfort. Homes offering this combination of outdoor space, mature landscaping, important updates, and convenient access to Winter Haven's Chain of Lakes are becoming increasingly difficult to find. Schedule your private showing today. Inside, natural light pours through the large sliding glass door, skylights, and surrounding windows, highlighting soaring ceilings and creating an open, airy feel throughout the main living areas. The living room is anchored by a fireplace that adds warmth and charm while enhancing everyday living and entertaining. The split-bedroom floor plan balances comfort and functionality. The spacious primary suite features dual closets, motorized blackout blinds, and an updated bathroom with a tiled walk-in shower and modern finishes. Secondary bedrooms offer flexibility for guests, hobbies, a home office, or changing lifestyle needs. Designed for daily living and entertaining, the kitchen offers abundant cabinetry, generous prep space, ample storage, and an oversized pantry rarely found in homes of this size. Fresh interior paint and durable hard-surface flooring throughout much of the home contribute to its move-in-ready appeal. One of the home's standout features is the expansive screened lanai measuring approximately 17' x 15' and overlooking the fenced backyard. A brick paver patio, detached storage shed, and double-gate access add even more functionality and convenience, creating outdoor space that can be enjoyed year-round. Adding even more appeal, the home is located minutes from public boat ramps serving Lake Eloise and Winter Haven's renowned Chain of Lakes, offering convenient access to boating, fishing, watersports, and outdoor recreation.

Listing is courtesy of: CENTURY 21 BE3 (727-596-1811)

Listing Agent: Patty Hernandez (863-535-7214)

Remarks: Under contract-accepting backup offers. This expansive property is a true diamond in the rough, perfectly positioned for the savvy investor looking for a great return on a "buy and hold" scenario or a strategic value-add project. Boasting a generous 0.41-acre lot, this property is designed for versatility. With a massive layout featuring 6 bedrooms and 4 bathrooms, the home offers the unique potential for 3 or even 4 separate doors (units), making it an ideal candidate for a multi-generational living setup or a high-performing rental portfolio addition. Only 12 minutes away from LEGOLAND!

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

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

Remarks: Move-In Ready with Major Updates! Welcome home to this beautifully refreshed 3-bedroom, 2-bath, 2-car garage residence offering over 1,700 square feet of comfortable living space in the heart of Winter Haven. Featuring a NEW ROOF, a NEW HVAC SYSTEM, and stylish interior finishes throughout, this home is ready for its next owner to move right in! Inside, you'll find a spacious open living and dining area that's perfect for entertaining family and friends or simply relaxing at home. The bright and inviting sunroom provides the perfect flex space for a home office, reading nook, playroom, or additional living area while overlooking the backyard. Step outside to enjoy the screened-in back porch—an ideal spot for morning coffee or evening relaxation. The backyard also includes a storage shed, providing plenty of room for tools, lawn equipment, or hobbies. Conveniently located near shopping, dining, schools, medical facilities, and Winter Haven's renowned Chain of Lakes, this home offers an excellent opportunity for first-time buyers, seasonal residents, or investors alike.

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

Listing Agent: Sam Daniels (863-412-8218)

Remarks: Short Sale. Investor opportunity in Winter Haven. Welcome to this 3 bedroom, 2 bath home offering an open and inviting layout with vaulted ceilings and a spacious family room designed for comfortable everyday living. Tile flooring flows seamlessly through the main living areas and into the galley kitchen, creating a bright and cohesive feel throughout the home. Built with durable block construction, this property also features a single car garage. Step outside to enjoy a beautifully shaded lot, perfect for relaxing or entertaining guests in a private outdoor setting. This is a Short Sale. Professionally processed by ARII SOLUTIONS, LLC. Buyer Responsible Short Sale Processing Fee of $5,000. Please review ''Presentation of Offers'' document before submitting offer. Property sold as-is

Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)

Listing Agent: Robert Arnold, Jr (407-389-7318)

Remarks: Amazing potential. This 2-bedroom, 2-bathroom townhouse features a spacious 1,252 square foot floor plan and is located in the established Stonebridge community.

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

Listing Agent: Sarah Armstrong (863-287-0252)

Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath home offering the perfect blend of comfort, functionality, and outdoor living. *Seller will contribute $5,000 towards buyer's closing cost or interest rate buy down with an acceptable offer.* Step inside to a spacious living and dining room combination, highlighted by a wood-burning fireplace, creating a warm and inviting focal point for the home. The updated kitchen features stainless steel appliances, stylish cabinetry, and a convenient breakfast bar perfect for casual dining or entertaining. The private primary suite offers a relaxing retreat with a walk-in closet and en-suite bathroom complete with a walk-in shower. Two additional guest bedrooms and a well-appointed hall bath with tub/shower combo provide ample space for family or visitors. Outdoor living truly shines with a screened lanai featuring a hot tub, overlooking the expansive fenced backyard designed for entertaining. Enjoy the above-ground pool with a wooden stairway deck, cozy fire pit area, and additional storage shed. All creating the ideal setting for gatherings or peaceful evenings at home. Additional highlights include a spacious two-car side-entry garage with laundry area, plus bonus office/workshop/storage space, as well as a one-car carport perfect for boat or camper parking. SOLAR power helps keep utility costs low, adding efficiency to this exceptional property! Solar will be paid in full at the time of closing! Conveniently located just steps from Lake Summit Public Boat Ramp and minutes from Cypress Gardens Boulevard, this home offers easy access to recreation, shopping, dining, and more. A rare opportunity to enjoy space, convenience, and lifestyle all in one remarkable property.

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: Ginger Quirk (863-430-5111)