Homes For Sale in Winter Haven 33881 - 271 homes

Remarks: LOCATION, LOCATION, LOCATION! ONLY MINUTES FROM ATTRACTIONS. THIS HARWICH FLOOR PLAN IS GREAT FOR ENTERTAINING WITH IT'S OPEN FLOOR PLAN. HOME IS WELL EQUIPED WITH SIDE BY SIDE FRIDGE, GLASS TOP RANGE, DISHWAHER, WASHER, DRYER, NEW 2026 ROOF AND MUCH MORE. MASTER SUITE IS VERY SPACIOUS AND MASTER BATH WITH STAND UP SHOWER AND DOUBLE VANITY. LAKESIDE LANDINGS IS A BEAUTIFUL COMMUNITY WITH A LOT OF GREEN SPACE, A NATURE TRAIL AND PARK AT LAKE CONINE, 2 POOLS (FREEFORM AND LAP), LARGE COVERED LANAI AREA WITH SEATING AND RESTROOMS, AND PLAYGROUND. 15 MINUTES TO LEGOLAND. STOP BY AND TAKE A LOOK AT LAKESIDE LANDINGS COMMUNITY.

Listing is courtesy of: KELLER WILLIAMS REALTY PREMIER (305-595-2844)

Listing Agent: Aileen Garciga (786-286-9372)

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: Discover unparalleled versatility and breathtaking lakefront living with this beautifully remodeled/converted dual-unit home on the shores of Lake Jessie in Winter Haven, Florida. Although zoned single-family residential, this property has been thoughtfully converted into two stunning living spaces—ideal for multigenerational families, in-law accommodations, or dual-family living side-by-side. Unit 1- 2,900 SF welcomes you with a fully renovated two-story layout featuring 4 bedrooms and 3 full bathrooms and 1 half bath. Enjoy gorgeous lakefront views from multiple vantage points and modern finishes throughout, creating the perfect blend of comfort and style. Unit 2- 2,800 SF, mirrors the same level of craftsmanship, two story offering 5 bedrooms and 3 full bathrooms. This spacious unit is also fully remodeled and showcases sweeping views of Lake Jessie, making every day feel like a retreat. Two car garage with additional storage room off the front of the garage. Your backyard becomes a true private oasis—complete with a fire pit, outdoor grill area with a pergola, and a covered boat dock equipped with a boat lift, water, and electric. Watch sea planes take off and land daily from Brown’s Sea Plane Base right from your own waterfront sanctuary. Whether you’re seeking a unique multigenerational setup, an expansive home for a large family, or the ultimate lakeside lifestyle, this exceptional property delivers it all. Don’t miss the opportunity to own this one-of-a-kind lakefront retreat in beautiful Winter Haven, Florida.

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

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

Remarks: This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.

Listing is courtesy of: THE URBAN GROUP, INC. (954-522-6226)

Listing Agent: Ashlee Morrell (941-740-9134)

Remarks: One or more photo(s) has been virtually staged. 4.99% Rate 30-year fixed FHA/VA Act now ! Step into this renovated farmhouse charm : 2-bedroom, 2-bathroom home, nestled on a spacious lot in the established Villa Manor neighborhood. NO HOA This move-in-ready residence presents luxury finishes, laminate flooring throughout, a sleek new kitchen with updated cabinets, carrara white quarts countertops, and stainless steel appliances, and a freshly tiled bathroom with contemporary finishes. Fresh interior and exterior paint, and upgraded lighting fixtures. The large backyard offers plenty of space for outdoor living or future expansion. Located minutes from local schools, parks, and downtown Winter Haven’s shops and restaurants, this home is perfect for first-time buyers, downsizers, or investors seeking turnkey potential.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Daniel Araque (321-276-0747)

Remarks: One or more photo(s) has been virtually staged. Welcome to 1936 Crossroads Blvd in the highly sought-after gated community of Crossroads at Lake Region. This exquisite entertainer’s paradise comes partially furnished, features a private screened pool and spa, upgraded finishes throughout, and a fully fenced backyard designed for relaxation and entertaining. This meticulously upgraded Rockingham II floor plan, built in 2018, offers nearly 2,500 square feet of thoughtfully designed living space with one of the most functional and desirable layouts in the community. The open-concept design provides a natural flow from the kitchen to the main living area with sweeping views of the covered lanai and pool enclosure, making the home ideal for both everyday living and entertaining. The kitchen features granite countertops, stainless steel appliances, pendant lighting, abundant cabinetry, and a large breakfast bar overlooking the main living area. Wood-look tile flooring throughout the main living areas adds durability while giving the home a clean, modern feel. The primary suite features an upgraded tray ceiling, abundant natural light, and a spacious walk-in closet with a custom California Closet system for added organization. The ensuite bath offers dual vanities, a soaking tub, and a separate glass-enclosed shower. Step outside to the true highlight of the home. The screened pool and spa area features an upgraded epoxy-coated deck that gives the outdoor space a clean, finished appearance while also being durable and easy to maintain. The fully fenced backyard provides privacy and security, while the covered lanai and extended deck space offer plenty of room for outdoor seating, grilling, and entertaining year-round. The property also features a dedicated irrigation well to help maintain the landscaping efficiently, thereby reducing water costs. The home is also equipped with a programmable permanent exterior lighting system, allowing for customizable accent lighting year-round. This incredible property is conveniently located near Highway 27 and the Polk Parkway, offering quick access to I-4, major metro areas, local theme parks and attractions, shopping, dining, and Florida’s beautiful beaches. Do not miss this incredible opportunity. Schedule your private showing today.

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Craig Murrell (863-409-7718)

Remarks: Under Construction. 2-story new construction townhome with 1,604 square feet, 3 bedrooms, and a covered lanai, located in the brand-new Harbor of Lake Henry community. Downstairs, enjoy an open layout(optional first floor layout with den)and a gourmet kitchen with, shaker-style wood cabinets, Samsung stainless steel appliances, including a pantry. The spacious gathering room opens to your covered lanai. The entire lower level and upstairs baths are finished with luxury vinyl plank flooring, with stain-resistant carpet in the bedrooms. Upstairs, you'll find three spacious bedrooms including your owner's suite complete with a walk-in wardrobe, linen closet, and a private en-suite bath with dual vanities and a tiled shower. Additional features for your convenience include a half bath downstairs, upstairs hall bath for the secondary bedrooms, energy-efficient insulation and windows, and a full builder warranty.

Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)

Listing Agent: George Lindsey, Iii (863-797-4999)

Remarks: Move-in ready and meticulously maintained! This spacious 4-Bedroom, 2.5-Bathroom two-story home was built in 2022. The main level offers seamless flow between the living room, dining area, and kitchen perfect for family gatherings. The kitchen showcases granite countertops, stainless steel appliances, a large center island with seating, deep sink, upgraded fixtures, and abundant cabinet space. A private main-floor office/den with double doors adds flexibility for remote work, fitness, or study, plus a convenient half bath downstairs. Upstairs, the generous primary suite features a large walk-in closet and an ensuite bath with dual sinks, granite counters, and an upgraded walk-in shower. The additional bedrooms are spacious, and the upstairs laundry room is centrally located for convenience. Situated on a desirable corner lot, the home offers excellent outdoor space including a covered back porch, ideal for relaxing or hosting gatherings. The backyard provides plenty of room to enjoy Florida living year-round. Lake Lucerne residents enjoy community amenities including two pool, a playground, and beautifully maintained space. Ideally located with easy access to Hwy 27 and approximately 20 minutes to I-4, you’re centrally positioned between Orlando and Tampa, about 45 minutes to Disney, 20 minutes to Legoland, and 35 minutes to Lakeland. Close to Winter Haven Hospital, Downtown Winter Haven, Publix, Walmart, Shopping and more! The roof, AC unit and water heater are all 4 years old. Schedule your private showing today!

Listing is courtesy of: HOMESMART (407-476-0451)

Listing Agent: Nan Seelall Llc (352-978-1050)

Remarks: Under contract-accepting backup offers. Discover the potential of this 3-bedroom, 2-bathroom home in Winter Haven, offering a versatile layout with a combined living and dining room perfect for everyday living or entertaining. The property features a fenced-in backyard, a spacious yard with room to customize, an empty pool ready for renovation or removal, and an enclosed back porch that adds extra flexible living space. With solid bones and plenty of opportunity to make it your own, this home is ideal for buyers looking to personalize a property in a desirable location.

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

Listing Agent: Jana Lutz (863-602-8992)

Remarks: ***PRICE REDUCTION*** Refined luxury meets modern efficiency in this stunning 4-bedroom, 3-bath home located in the private gated community of Hampton Cove, tucked away on a peaceful cul-de-sac, accented by elegant brick exterior detailing. Designed for both sophistication and comfort, this meticulously upgraded home offers timeless finishes, flexible living spaces, and exceptional energy efficiency. Inside, luxury vinyl plank flooring flows throughout, complemented by granite countertops in every space. The chef-inspired kitchen is beautifully appointed with stainless steel appliances, rich granite surfaces, a designer backsplash, deep drawer storage, and soft-close cabinetry, a breakfast bar, and a sunlit dinette-creating a space that is as functional as it is striking. A dedicated dining room provides the perfect setting for hosting and formal gatherings. The primary suite serves as a serene retreat, featuring a private sitting area and a spa-style en-suite bath with a soaking tub and walk-in shower. Bedrooms two, three, and four are generously sized, offering comfort and flexibility for family, guests, or additional work-from-home needs. Both guest bathrooms are thoughtfully designed with walk-in showers, offering elevated comfort for family and guests alike. A versatile flex room allows effortless customization—ideal for a private office, fitness studio, or creative space. Outdoors, the expansive fenced backyard provides abundant room for a resort-style pool, with a strategically located bathroom perfectly suited for future pool access. This home is enhanced with top-tier systems and energy-conscious upgrades, including: • Lennox 19.5 SEER high-efficiency A/C (2018) with damper system and four thermostats • Fully paid solar panels • 16kW whole-home Generac generator powered by natural gas • Hybrid water heater (2018) • Roof, A/C, and water heater replaced in 2018 • Energy Recovery Ventilator (ERV) in the garage for improved air quality and humidity balance • Double-pane windows throughout • Backyard fencing added in 2023 • Washer and dryer (2025) included. This exceptional home delivers luxury, resilience, and efficiency in one elegant package—an opportunity rarely found.

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

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

Remarks: Welcome to 525 Winter Terrace in Winter Haven, an inviting, move-in-ready 2-bedroom, 2-bath, single-level townhouse in a maintenance-free family community with outstanding amenities. Step inside to find ceramic tile throughout the main living areas, spacious bedrooms, and a bright Florida room perfect for relaxing or entertaining. The heart of the home is the completely updated kitchen featuring nice appliances, wood cabinetry, and granite countertops, complemented by neutral interior paint and updated tile. Enjoy even more comfortable living space in the enclosed back room, offering additional air-conditioned square footage. The primary suite has sliding glass doors that lead to your own, private, enclosed porch. Community perks include a clubhouse, solar-heated pool, shuffleboard, and a private boat dock on beautiful Lake Smart. Schedule your showing today because this one won’t last long!

Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)

Listing Agent: Oralis Perez (407-325-1045)

Remarks: Welcome To Hartridge Hills!! This Gorgeous Gated Community is one of Polk County's Hidden Treasures. An established and well maintained community of charming custom homes, each one uniquely it's own. Nestled between Lake Pansy and Lake Hartridge, this community offers boat lovers their own private boat ramp with access to the Chain of Lakes. This community also has been home to many pilots over the years and is conveniently located beside the Winter Haven Airport and only minutes to Publix and all major medical facilities making this community a perfect location. Situated on a corner lot, this well built home by Ernie White is a split plan offering 3 bedrooms & 2 baths plus a den or office space. The dining room, living area and bedrooms have new luxury vinyl. There is High ceilings throughout, crown molding, updated granite in the kitchen and bathrooms. The roof was replaced in 2017. HOA fee's include lawn care and the irrigation system is on a small well, saving you money on your water bill! Grab your favorite beverage & Relax and Enjoy the water views on your enclosed back lanai. Come check out this beautiful property, You'll love being a part of this quaint community!!

Listing is courtesy of: PREMIER HOMES AND REAL ESTATE (863-937-8942)

Listing Agent: Christy Smith (863-409-8709)

Remarks: HUGE price reduction! Lakefront Living in Hamilton Point! Discover this spacious 5-bedroom, 3-bath home located in the upscale Hamilton Point community, within the city limits of Winter Haven. Situated on just under one acre, this rare lakefront property offers space, privacy, and the perfect setting for enjoying Florida’s outdoor lifestyle. Start your summer right with direct access to Lake Hamilton, a beautiful 2,142-acre lake known as one of Central Florida’s premier fishing destinations. Whether you enjoy waterskiing, jet skiing, fishing, or relaxing boat rides, this lake has something for everyone. Even better, this property offers true chain access to two additional lakes, expanding your boating adventures. Take a short ride across the water to two of the area’s favorite spots—Port 27 for waterfront dining or the local favorite Floridino's Italian Kitchen, known for serving some of the best pizza around. You might even spend an afternoon simply relaxing on the water while watching seaplanes land and take off. Surrounded by mature vegetation and located in a quiet, well-established community, this home truly has so much to offer. Properties like this are a rare find—especially on true lakefront acreage in such a desirable location.

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

Listing Agent: Lamanda Jones (863-557-3627)

Remarks: Welcome to this spacious and recently upgraded home sitting on a rare 0.40-acre corner lot with NO HOA and NO CDD, giving you the freedom and space you’ve been looking for. Major recent improvements include updated HVAC, electrical, and plumbing systems for added peace of mind, along with attractive interior upgrades featuring modern flooring, an updated kitchen with stylish cabinetry and stainless-steel appliances, and refreshed bathrooms with contemporary tile finishes. The oversized lot offers endless possibilities and plenty of room to park your RV, boat, jet ski, work vehicles, or recreational toys worry-free — something hard to find in today’s market. Conveniently located near major supermarkets, restaurants, schools, and main roads for easy commuting, this property is ideal for homeowners seeking space and flexibility or investors looking for a strong opportunity. Schedule your private showing today and discover the value, freedom, and potential this unique property has to offer!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Jose Hooker-Gomez (407-272-6986)

Remarks: Charm and curb appeal abound for this Winter Haven Home! Step inside into the inviting foyer, which is flanked on the right by the three secondary bedrooms. Through the well-appointed living room you'll find the kitchen, which boasts stainless steel appliances, hard surface countertops, and ample storage. Rounding out this ranch style floorplan is the dining room and the primary suite. Come and see for yourself the possibilities that this home has to offer!

Listing is courtesy of: EVERYSTATE INC. (501-725-1234)

Listing Agent: Blake Keathley (661-900-9145)

Remarks: Under contract-accepting backup offers. Turnkey Duplex Investment, reliable Income, renovated, & low maintenance. Excellent opportunity to acquire a fully rented, income-producing duplex in a convenient Winter Haven location. This solid block construction property features two spacious 2-bedroom, 1-bath units, each with a well designed, functional layout that tenants love. The property has been recently renovated, including fresh interior paint and new appliances, offering a clean, modern feel and minimizing near-term maintenance expenses. Both units are occupied by reliable, long term tenants, providing immediate and steady cash flow from day one. Strong rental demand in the area, combined with the property's durable block construction, great location, and updated interiors, makes this an ideal addition to an investor's portfolio, whether you're a seasoned buyer or looking for your next low-hassle income property. To respect tenant privacy, property may be previewed once under contract. Do not disturb tenants. Key Highlights: Duplex with 2 bed / 1 bath on each side Fully occupied with dependable tenants in place, Newly renovated: paint & appliances, Block construction for durability and longevity, Nice, efficient layouts, Great location with continued renter demand. Turnkey investment with steady income

Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (727-898-6800)

Listing Agent: Mary Lannin (231-883-2286)

Remarks: Welcome home to Brenton Manor! This move-in ready 3-bedroom, 2-bathroom split-plan home checks every box — and then some. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for entertaining or relaxing after a long day. Step outside to your private, fully fenced backyard with no rear neighbors — your own Florida oasis. Big-ticket updates have already been done for you: brand-new 2026 HVAC with UV ray lights and professionally cleaned ductwork, 2026 whole-home water softener system, 2025 tankless water heater, 2025 fresh exterior paint, 2025 gutters, and a 2023 roof. Both bathrooms feature updated showers, so all you need to do is move in and enjoy. Nestled in the established Brenton Manor community near US-27 and beautiful Lake Hamilton, this home offers the perfect blend of comfort, convenience, and peace of mind. Conveniently located minutes from I4 offering easy access to major roadways, downtown Orlando, MCO airport, short drive to theme parks, premier shopping, dining and world class health facilities. Schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)

Listing Agent: Cynthia Davis (407-619-2937)

Remarks: INVESTORS! Take a look at this 1914 Crafstman Bungalow style home! This opportunity is located in the heart of the Winter Haven Heights Historic Residential District that was added to the National Register of Historic Places in 2000! Just 200 feet to the Kiwanis Park on the shores of Lake Martha! Spacious rooms with high ceilings waiting for your imagination are renovation! New Roof 2024! Call for your private showing today!

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

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: Welcome to this beautifully reimagined 4-bedroom, 2-bathroom pool home, perfectly positioned on a premium corner lot. Thoughtfully updated with a new roof (2021), HVAC (2024), and fresh interior paint throughout—including ceilings and the pool deck—this residence offers effortless, move-in-ready living. Inside, a refined layout unfolds with a formal dining space and a flexible bonus room, ideal for a private office or curated living area. The heart of the home showcases an open-concept design, where the living room flows seamlessly into a sophisticated kitchen and breakfast space, perfect for both intimate gatherings and entertaining. The kitchen is appointed with quartz countertops, high-end appliances, a built-in bar fridge, and a convenient pot filler, blending style with function. A desirable three-way split floor plan ensures privacy and comfort throughout. Outdoors, enjoy a screened-in patio overlooking a sparkling pool, complemented by a generously sized, fully fenced backyard, your own private retreat designed for the Florida lifestyle. Experience the perfect blend of modern upgrades and timeless comfort. Schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Kevin Asenjo (407-844-5252)

Remarks: Welcome to this beautiful 4-bedroom, 2.5-bath home that perfectly blends comfort and charm. Major updates have already been completed, including a new roof installed in May 2025, foundation work completed in November 2024, a new sliding door added in November 2024, and the main floor has recently been updated. Step inside to find spacious living areas, ideal for both everyday living and entertaining. The real showstopper is the dream backyard—an outdoor oasis featuring a stunning pool and an incredible farm-style barn that offers endless possibilities, from hobbies to storage or even a unique entertaining space. This property truly has it all—space, style, and a one-of-a-kind backyard retreat you won’t want to miss! Property is being sold As-Is. The property also features a brand-new barn shed and solar panels, offering added value and efficiency for the next owner.

Listing is courtesy of: NORKIS & CO REALTY (407-506-7070)

Listing Agent: Daisy Perez (407-951-4218)