Refine Search
Sort by
357 Ruby Lake Loop, Winter Haven
$392,900
3 Beds ⋅ 2 Baths ⋅ Ruby Lake Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to your dream home in the gated community of Ruby Lake! This beautifully designed 3-bedroom, 2-bath Cassidy “Ox” floor plan perfectly balances elegance and everyday comfort. Step inside to discover a spacious layout featuring formal living and dining rooms, along with a generous family room—ideal for both entertaining and relaxed living. The updated kitchen is truly the heart of the home, showcasing sleek quartz countertops, a breakfast bar, closet pantry, and durable tile flooring. Retreat to the impressive primary suite, offering a large 17x15 bedroom, walk-in closet, and a spa-like en suite bath complete with soaking tub, walk-in shower, and dual vanities. Thoughtfully designed, the secondary bedroom and bath are handicap accessible with widened doorways for added ease. Enjoy Florida living year-round on the expansive 10x38 screened lanai—perfect for gatherings or quiet evenings. Additional highlights include an interior laundry room with sink, surround sound throughout, plantation shelving with ambient lighting, ceiling fans, irrigation system with separate meter, and a 2-car garage with a high-profile door. Conveniently located near shopping, dining, medical facilities, schools, and Legoland, with easy access to Tampa and Orlando—this exceptional home truly has it all. Don’t miss your opportunity to make it yours!

357 Ruby Lake Loop, Winter Haven

194 S Lake Mariam Drive, Winter Haven
$390,000
2 Beds ⋅ 2 Baths ⋅ Valencia Wood Estates First Add SubDv. ⋅ 33884 Zip Code
** $10K PRICE REDUCTION!** Welcome to this beautifully updated home in desirable Southeast Winter Haven, offering space, privacy, and modern upgrades on a generous half-acre lot. Step inside to vaulted ceilings and rich hardwood flooring that create a warm, open feel. The living room features a gas fireplace with mantle detail, adding character and comfort to the main gathering space. The fully renovated kitchen stands out with stainless steel appliances, granite countertops throughout, updated shaker-style cabinetry, and a sleek glass vent hood for a clean, contemporary finish. The layout flows effortlessly into the dining and living areas, making it ideal for both everyday living and entertaining. The enclosed rear patio is fully incorporated into the heated and cooled square footage, providing additional living space in a controlled climate year-round. From here, you overlook the expansive backyard with mature trees and complete privacy — and with no rear neighbors, that view and buffer will never change. The updated bathroom features a spacious walk-in shower with modern tile accents, granite vanity top, and upgraded lighting for a polished, spa-like feel. Outside, the half-acre homesite offers exceptional flexibility. There is ample room for a future pool, garden, or additional structure, along with space for boat or RV parking. A detached shed provides extra storage. The property backs to natural privacy with no rear neighbors ever, creating a peaceful setting that’s hard to find. Located in a one-way-in, one-way-out area of Southeast Winter Haven, the neighborhood offers limited traffic and added privacy while still being conveniently close to everything. With a little effort, this home could easily be converted into a 3-bedroom layout, adding even more value and flexibility for future owners. If you’re looking for updated interiors, privacy, and room to grow — this one checks boxes that most homes simply don’t.

194 S Lake Mariam Drive, Winter Haven

5378 San Pietro Drive, Winter Haven
$389,999
5 Beds ⋅ 3 Baths ⋅ Villa Mar SubDv. ⋅ 33884 Zip Code
Under Construction. Valencia BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender.  Prepare to be impressed by the Valencia, a two-story home featuring 5 bedrooms, 3 bathrooms, and a 2-car garage. This floorplan is designed for modern living and effortless entertainment. Step through the elegant foyer into a vibrant main living area, complete with a private guest suite for ultimate comfort. The kitchen shines with sleek quartz countertops, stainless steel appliances, and luxurious vinyl plank flooring overlooking the dining area which flows beautifully to the covered lanai through sliding glass doors. Upstairs, you’ll find the secluded owner’s suite complete with a walk-in shower, dual vanity and spacious walk-in closet. Conveniently located by the additional bedrooms is the cleverly designed oversized laundry room. Another modern feature of the Valencia is the smart thermostat with voice control, making energy efficient living a breeze. Outside, enjoy the chic elevation and professionally curated landscaping that adds the perfect finishing touch to this exceptional home. 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.

5378 San Pietro Drive, Winter Haven

605 Sarner Pass Way, Winter Haven
$389,900
4 Beds ⋅ 3 Baths ⋅ Lake Lucerne Ph 5 SubDv. ⋅ 33881 Zip Code
Move-in ready, built in 2022. Welcome to 605 Sarner Pass Way, a spacious 4-bedroom, 2.5-bath home with a flexible first-floor bonus room—perfect for a home office, guest space, playroom, or fitness room. The open-concept main level offers an inviting living and dining area alongside a well-appointed kitchen featuring granite countertops, stainless-steel appliances, a large center island, and abundant cabinetry. Upstairs, the spacious primary suite features a walk-in closet, dual vanities, and walk-in shower, with three additional bedrooms providing plenty of room for family or guests. Enjoy Florida living from the covered lanai overlooking a generous backyard. Lake Lucerne residents enjoy two community pools, a playground, and maintained common areas. Conveniently located approximately 6 minutes from Hwy 27, with easy access to Davenport shopping and dining, Central Florida attractions, Orlando-area airports, and routes toward Tampa. With newer major systems from its 2022 construction and flexible owner-financing options available, this home is ready for its next owner. Schedule your private showing today!

605 Sarner Pass Way, Winter Haven

228 W Lake Ina Drive, Winter Haven
$389,000
3 Beds ⋅ 4 Baths ⋅ Eloise Woods Lake Roy Un SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to lakefront living on beautiful Lake Ina in Winter Haven! This 3 bedroom, 4 bathroom pool home with NO HOA offers generously sized bedrooms, wood flooring throughout the living areas and bedrooms, and tile in the kitchen and bathrooms. The kitchen features granite countertops, wood cabinetry, a tile backsplash and a convenient breakfast bar. Two of the bathrooms showcase charming retro styling, adding unique character to the home. Two large picture windows frame peaceful lake views and fill the interior with natural light. Step outside and experience the Florida waterfront lifestyle, with opportunities to spend your days boating, fishing, water skiing or simply relaxing by the water and enjoying the views. Designed for outdoor living and entertaining, the property includes a covered deck, covered patio, outdoor kitchen, outdoor shower and a large swimming pool surrounded by an impressive 57 by 63 foot paver patio, along with a pool bath. Whether hosting poolside gatherings, launching out for a day on the lake or unwinding by the water at sunset, this home offers a true lakefront retreat!

228 W Lake Ina Drive, Winter Haven

107 Sanderling Drive, Winter Haven
$385,000
4 Beds ⋅ 2 Baths ⋅ Hamilton West Ph 02 SubDv. ⋅ 33881 Zip Code
Welcome to **107 Sanderling Drive**, a spacious and inviting **4-bedroom, 2-bathroom single-family home** in the desirable Hamilton West community of Winter Haven. Offering approximately **2,567 square feet of living space**, this one-story home provides plenty of room for comfortable everyday living, entertaining, and creating lasting memories. Step inside to a welcoming floor plan featuring spacious living and dining areas, an eat-in kitchen, vaulted ceilings, crown molding, and a combination of wood and tile flooring. The kitchen offers generous cabinet and counter space and opens toward the breakfast area and family room, creating a great gathering space for family and friends. The split-bedroom layout provides privacy for the primary suite, which features **two walk-in closets, dual sinks, a garden tub, and a separate walk-in shower**. Recent and important property improvements include a **new roof installed in 2024 with architectural shingles**, providing added peace of mind for years to come. The home features an **HVAC system with dual-purpose natural gas heating and cooling**, along with a **natural gas water heater**. A **well irrigation system services the sprinkler system**, helping maintain the landscaping while providing an efficient source for irrigation. Additional features include a **two-car attached garage**, ceiling fans, window treatments, and a spacious **0.26-acre lot** with approximately **11,326 square feet of land**, providing plenty of room to enjoy Florida's outdoor lifestyle. Located in the heart of Winter Haven's famous **Chain of Lakes region**, residents can enjoy boating, fishing, kayaking, water sports, and beautiful waterfront recreation. Nearby **Lake Howard** and the surrounding lakes provide numerous opportunities for outdoor adventures and relaxation. Enjoy the shops, restaurants, entertainment, and community events of **downtown Winter Haven**, or spend the day exploring local parks and nature areas. Family-friendly attractions and activities are also nearby, including **LEGOLAND Florida Resort**, golf courses, walking and biking trails, and numerous recreational facilities throughout the Winter Haven area. Conveniently located with easy access to major roadways, this home provides a great balance of peaceful residential living and proximity to shopping, dining, recreation, medical facilities, and Central Florida attractions. With its spacious floor plan, **2024 architectural shingle roof**, natural gas HVAC and water heater, well irrigation system, and desirable Winter Haven location, **107 Sanderling Drive** is an excellent opportunity to enjoy the Central Florida lifestyle. **Come see all this wonderful home has to offer!**

107 Sanderling Drive, Winter Haven

136 Lake Mariam Road Se, Winter Haven
$385,000
4 Beds ⋅ 3 Baths ⋅ Lakewood Community Association SubDv. ⋅ 33884 Zip Code
*NEW-PRICE REDUCTION in a classic Winter Haven Community-Beautiful Home!* *NEW ROOF 2026 * NEW INSULATION 2026 * NEW HOT WATER HEATER 2026* NEWER AIR CONDITIONER 2020* Welcome to the classic neighborhood of Lakewood, located in Southeast Winter Haven. This spacious 4 bedroom, 3 bath home, & with the additional 4th bedroom it offers versatility, including a closet, private sliding door access, making it ideal for a bedroom, office/flex room, guest space, or home office. The split floor plan provides comfortable living with over 2,300 square feet of living space, multiple living and entertaining areas, a convenient inside laundry room, and beautiful hard wood flooring in the living room, dining room, and family room, this home offers endless potential. Step outside to enjoy the large screened in-ground pool with heater, perfect for relaxing and entertaining year round. Conveniently located near shopping, dining, medical facilities, and Winter Haven's Chain of Lakes, this home is ready for its next owners to add their personal touches and make it their own. Schedule your private showing today!

136 Lake Mariam Road Se, Winter Haven

344 Alexzander Way, Winter Haven
$385,000
5 Beds ⋅ 3 Baths ⋅ Jace Lndg SubDv. ⋅ 33881 Zip Code
Welcome to this stunning 5-bedroom, 3-bath home located in the Jace Landing community of Winter Haven. Built in 2021, this modern two-story residence provides nearly 2,700 square feet of living space designed for comfort, flexibility, and contemporary living. The open-concept layout features a bright and spacious great room, modern finishes, and a large kitchen with stainless steel appliances, ample cabinetry, and an oversized island perfect for family gatherings and entertaining. The first floor also includes a versatile flex room or optional sixth bedroom and a full bathroom, making it ideal for guests, a home office, or multi-generational living. Upstairs, the primary suite provides a private retreat with a large walk-in closet and an ensuite bath featuring dual vanities and a walk-in shower. Four additional bedrooms and a convenient upstairs laundry room create plenty of space for the whole family. This home is built with durable block construction on both levels and includes smart-home technology with Alexa integration and energy-efficient systems throughout. Outside, enjoy the covered patio and spacious backyard — perfect for relaxing or hosting outdoor get-togethers. Conveniently located just minutes from downtown Winter Haven, Legoland, shopping, dining, and with easy access to I-4, this home combines modern comfort with everyday convenience. Don’t miss your chance to own this move-in-ready home in one of Winter Haven’s most desirable communities.

344 Alexzander Way, Winter Haven

128 N Lake Florence Drive, Winter Haven
$384,900
3 Beds ⋅ 2 Baths ⋅ Eloise Woods SubDv. ⋅ 33884 Zip Code
Lake Views | Paid-Off Solar System | Mother-in-Law Suite | NO Flood Zone | Exceptional Upgrades | New Roof | Welcome to your own private retreat in the heart of beautiful Winter Haven, Florida! Perfectly positioned on an elevated home-site overlooking the peaceful waters of Lake Florence, this meticulously maintained 3-bedroom, 2-bathroom residence offers 2,167 square feet of thoughtfully designed living space, complete with an Attached Mother-In-Law Suite—perfect for multi-generational living, visiting guests, a home office, or added flexibility. From the moment you arrive, you’ll appreciate the quality, care, and countless upgrades that make this home truly move-in ready. Built with solid block construction and situated high and dry in NO FLOOD ZONE, this property delivers both comfort and peace of mind. Inside, the warm and inviting floor plan features rich pecan wood cabinetry, modern appliances, and a charming wood-burning fireplace that creates the perfect centerpiece for relaxing evenings or entertaining family and friends. The spacious 2-car garage provides plenty of room for vehicles, storage, and weekend projects. Designed with efficiency and long-term value in mind, this home boasts a remarkable list of improvements, including a 2020 roof, fully paid-off 2020 solar panel system, and 50-year transferable warranties on both the roof and solar system. With energy costs continuing to rise, you’ll enjoy the financial benefits of owning your solar system outright while dramatically reducing your monthly electric bills. Additional premium upgrades include a 2023 4-ton HVAC system, 2023 electrical panel, a 2023 mini-split system dedicated to the mother-in-law suite, Custom installed New South double-pane energy-efficient windows and front entry door backed by a lifetime warranty, and fresh exterior paint completed in 2026. In addition, an on-site utility shed, fully permitted with hurricane clips, power connected for additional storage to meet and exceed all of your storage needs! Wake each morning to breathtaking sunrises over Lake Florence, then unwind in the evening with spectacular Florida sunsets from your elevated vantage point. It’s the perfect setting to enjoy everything that makes Central Florida living so special. Ideally located just minutes from LEGOLAND Florida Resort, Winter Haven’s renowned Chain of Lakes, top-rated schools, shopping, dining, golf, and everyday conveniences, this home offers an exceptional combination of location, lifestyle, and lasting value. Homes with this level of craftsmanship, energy efficiency, flexible living space, and picturesque lake views are a rare find. Don’t miss your opportunity to own this incredible Winter Haven property—schedule your private showing today and experience Florida living at its finest.

128 N Lake Florence Drive, Winter Haven

2108 River Hawk Loop, Winter Haven
$384,900
4 Beds ⋅ 2 Baths ⋅ Residences At Winter Haven SubDv. ⋅ 33880 Zip Code
Move-in Ready! Welcome to the Everglades at Residences at Winter Haven, an exclusive 63-lot semi-custom community offering exceptional craftsmanship, modern design, and a prime central Winter Haven location. This thoughtfully designed 4-bedroom, 2-bath home features an open-concept layout that blends style and functionality. At the heart of the home, the designer kitchen showcases a stunning waterfall island, 42-inch soft-close cabinetry with crown molding, stainless steel appliances, abundant storage, and a spacious walk-in pantry. The extended great room flows seamlessly to the covered lanai, creating the perfect space for everyday living and entertaining. Additional features include luxury vinyl flooring throughout the main living areas, floor-to-ceiling porcelain tile in the showers, blinds throughout, four ceiling fans, a dedicated laundry room, and a 2-10 Home Buyers Warranty for added peace of mind. Residences at Winter Haven offers low HOA fees of just $225 quarterly, no CDD fees, and the opportunity to personalize future homes by selecting your lot, floor plan, exterior finishes, interior design package, and upgrade options. Experience quality construction, thoughtful design, and a community you'll be proud to call home.

2108 River Hawk Loop, Winter Haven

1652 Lemon Avenue, Winter Haven
$380,000
4 Beds ⋅ 3 Baths ⋅ Eagle Crest SubDv. ⋅ 33881 Zip Code
Welcome to 1652 Lemon Ave in Winter Haven, Florida! Built in 2019, this spacious home offers approximately 2,509 square feet of living space and a desirable four-bedroom layout, providing plenty of room to spread out, entertain, and enjoy everyday living. Whether you're looking for additional space to work from home, host guests, or create the lifestyle you've been looking for, this property offers an excellent opportunity in a convenient Winter Haven location. Enjoy easy access to everyday essentials. Outdoor recreation is close by, with local parks such as Trailhead Park Playground and Lake Howard Park offering opportunities to enjoy the Florida sunshine, walking trails, and time outdoors. Looking for entertainment and weekend activities? Explore the shops and restaurants of historic Downtown Winter Haven, enjoy the area's beautiful Chain of Lakes, or plan a fun-filled day at LEGOLAND Florida Resort. With convenient access to local dining, recreation, shopping, and entertainment, this location offers a great balance of everyday convenience and Central Florida fun. If you're searching for a spacious home in Winter Haven with room to make it your own and convenient access to local amenities, 1652 Lemon Ave is one to put on your list. Schedule your showing and discover the possibilities!

1652 Lemon Avenue, Winter Haven

210 Meadowbrook Boulevard, Winter Haven
$380,000
5 Beds ⋅ 3 Baths ⋅ Lucerne Park Reserve SubDv. ⋅ 33881 Zip Code
Motivated Seller!! Welcome to this beautifully maintained home in the desirable Meadowbrook community of Winter Haven! From the moment you arrive, you'll appreciate the inviting curb appeal, functional layout, and comfortable living spaces designed for everyday living and entertaining. The open-concept floor plan flows seamlessly into the spacious kitchen and living area, creating the perfect place to gather with family and friends. The primary suite offers a relaxing retreat, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to enjoy the backyard, ideal for morning coffee, weekend barbecues, or simply unwinding after a long day. Conveniently located near shopping, dining, medical facilities, parks, and major roadways, this home offers the perfect balance of comfort and convenience. Whether you're a first-time homebuyer, growing family, or looking to downsize, this property is ready to welcome you home. Don't miss your opportunity to own this wonderful Winter Haven home.

210 Meadowbrook Boulevard, Winter Haven

2925 E Lake Hartridge Drive, Winter Haven
$380,000
4 Beds ⋅ 3 Baths ⋅ Pine Terrace Rep SubDv. ⋅ 33881 Zip Code
BACK ON THE MARKET DUE TO BUYERS FINANCING!! Welcome to this beautifully maintained 4-bedroom, 3-bathroom pool home situated on a desirable corner lot in Winter Haven! Offering a flexible floor plan, the spacious 4th bedroom can easily serve as a bonus room, home office, playroom or guest suite to fit your lifestyle. Inside, you'll find a stylish luxury vinyl plan flooring throughout and an open-concept living area perfect for everyday living and entertaining. The kitchen features granite countertops, ample cabinetry and an eat-in dining area. Step outside to your private backyard oasis complete with a sparkling pool, ideal for enjoying Florida's year-round sunshine. With a low HOA and a convenient location between Tampa and Orlando, this home offers the perfect combination of comfort, flexibility, and value. Schedule your private showing today!

2925 E Lake Hartridge Drive, Winter Haven

215 Kilmer Lane, Winter Haven
$379,998
4 Beds ⋅ 3 Baths ⋅ Fla Highlands Co Sub SubDv. ⋅ 33884 Zip Code
Fully Occupied Income Property | 3 Units | $4,300/mo Gross Rent | No Vacancy | Winter Haven Rare turnkey income property generating $4,300/month in gross rent — fully occupied with zero vacancy. This versatile multi-income single-family property features two interior apartments plus a separate rear cabin, each independently rented with established tenants in place. Landlord expenses are minimal: owner covers water (~$25/mo) and basic WiFi ($50/mo). Tenants handle electricity, lawn maintenance, and all other utilities — maximizing net cash flow from day one. 4 bedrooms | 2 bathrooms | 1,680 sq ft | Built 1965 | Polk County | Minutes from US-27, downtown Winter Haven, and Legoland Florida. Ideal for the buy-and-hold investor seeking immediate cash flow with low management overhead. Current leases transfer at closing. All financing welcome: Conventional | DSCR Loan | Cash.

215 Kilmer Lane, Winter Haven

204 Inman Boulevard, Winter Haven
$379,900
5 Beds ⋅ 3 Baths ⋅ Inman Groves SubDv. ⋅ 33881 Zip Code
NO CDD and a BRAND NEW FENCE!!! Oh my!! Welcome home to this beautifully maintained 5-bedroom, 3-bath residence offering nearly 2,700 square feet of flexible living space in one of Winter Haven's fastest-growing areas. Priced at just $379,900, this spacious home delivers exceptional value with room for everyone. Designed with today's lifestyles in mind, the thoughtfully crafted floor plan includes five true bedrooms, three full bathrooms, and a versatile flex room that can easily serve as a home office, playroom, media room, gym, or even a sixth bedroom. A first-floor guest suite provides the perfect setup for visitors, extended family, or multigenerational living. The heart of the home features an open-concept kitchen complete with granite countertops, abundant cabinet space, and plenty of room for gathering with family and friends. Durable tile flooring throughout the main living areas adds both style and easy maintenance, while the home's immaculate condition means you can move right in and start enjoying it from day one. Step outside to enjoy one of this home's standout features—no rear neighbors. Whether you're sipping your morning coffee or relaxing after a long day, you'll appreciate the added privacy and peaceful backdrop. Conveniently located just minutes from downtown Winter Haven, you'll enjoy easy access to local restaurants, boutique shopping, the historic Ritz Theatre, Saturday farmers markets, the public library, and the Chain of Lakes lifestyle that makes Winter Haven so special. A brand-new Publix is under construction just a short distance away, making everyday errands even more convenient. The community offers a low HOA with no CDD fees, helping keep monthly ownership costs affordable. You'll also be just minutes from Legoland Florida Resort and approximately 30 minutes from Walt Disney World, making this an ideal location for both everyday living and entertaining visiting family and friends. If you've been searching for a home that combines generous living space, a flexible floor plan, modern finishes, and an unbeatable Central Florida location, 204 Inman Boulevard is ready to welcome you home.

204 Inman Boulevard, Winter Haven

301 Terranova Boulevard, Winter Haven
$379,900
4 Beds ⋅ 2 Baths ⋅ Terranova Ph 04 SubDv. ⋅ 33884 Zip Code
Discover this spacious 4-bedroom, 2-bath, 1,960 SqFt home in the gated Terranova community of Winter Haven, offering the comfort, privacy, and location today’s buyers are looking for—all just minutes from LEGOLAND Florida Resort. Step inside to an inviting and functional layout with generous living spaces designed for everyday comfort and entertaining. Outside, enjoy your own private retreat with a fully fenced backyard and relaxing spa/jacuzzi—perfect for unwinding after a long day or enjoying Florida living year-round. Terranova offers the added benefits of gated access, NO CDD, and a low HOA, providing an attractive combination of community living and affordability. The home is conveniently located near shopping, dining, medical facilities, schools, entertainment, and major Central Florida destinations. The property is equipped with leased solar panels. The solar will be transferred to the buyer subject to the solar provider’s requirements and approval. Additional information regarding the solar is available upon request. Ask about available financing and down payment assistance options that may help make homeownership more accessible. Schedule your private showing today and discover everything 301 Terranova Blvd

301 Terranova Boulevard, Winter Haven

2112 Avenue C  Sw, Winter Haven
$379,000
4 Beds ⋅ 2 Baths ⋅ West Winter Haven SubDv. ⋅ 33880 Zip Code
Step into a piece of Winter Haven history—beautifully reimagined for modern living. Just moments from Lake Howard, this exceptional 1925 residence offers the character and craftsmanship today's luxury buyers crave, paired with a complete top-to-bottom transformation. Original refinished 101 year old hardwood floors and two sets of original French doors provide a timeless connection to the home's past, while the rest has been thoughtfully rebuilt with today's lifestyle in mind. The custom kitchen, elegant architectural details, crown molding, tray ceilings, and spacious living areas create a home that feels both sophisticated and inviting. The private primary suite is a true retreat, featuring his-and-hers walk-in closets and a spa-inspired ensuite with a two-person tiled shower, garden tub, and generous vanity space. Two additional bedrooms upstairs add flexibility for guests, family, or a private home office. With approximately 2,011 heated square feet, 4 bedrooms, 2 baths, a dedicated laundry room, fully fenced backyard, and no HOA, this is a rare opportunity to own something with genuine character—not another cookie-cutter home. Bring your boat and water toys and enjoy the freedom and lifestyle that come with living near Winter Haven's beautiful Chain of Lakes. For buyers who appreciate history, character, and modern luxury, this is a home that simply must be experienced in person.

2112 Avenue C Sw, Winter Haven

4099 Island Lakes Drive, Winter Haven
$379,000
3 Beds ⋅ 2 Baths ⋅ Island Lakes SubDv. ⋅ 33881 Zip Code
One or more photo(s) has been virtually staged. NEW ROOF 2/9/2026 + $10K PRICE IMPROVEMENT on 7/24! Now offered at another improved price, this waterfront home on Lake Rochelle delivers the best value currently available on the Winter Haven Chain of Lakes. Located in the desirable Island Lakes community, this well-maintained 3-bedroom, 2-bath home combines lakefront living, major recent updates, and everyday functionality. A brand new roof was installed in February 2026, offering added peace of mind and potential insurance advantages for the next owner. Fresh landscaping and new sod create excellent curb appeal, while the open split-bedroom floorplan provides comfortable living with beautiful natural light throughout. The spacious primary suite overlooks the water and includes a private bath and walk-in closet. The living and dining areas flow easily into the kitchen, making the home ideal for entertaining, weekend guests, or simply enjoying the lake lifestyle. Step outside and enjoy direct access to the Chain of Lakes with boating, fishing, kayaking, and sunset views right from your backyard. Conveniently located near shopping, dining, medical facilities, and major roadways while still offering a peaceful waterfront setting. Whether you’re looking for a primary residence, winter retreat, or investment opportunity, this property checks all the boxes for Florida lakefront living. Schedule your private showing today.

4099 Island Lakes Drive, Winter Haven

1501 N Lake Howard Drive, Winter Haven
$375,000
3 Beds ⋅ 2 Baths ⋅ Interlaken Add SubDv. ⋅ 33881 Zip Code
A rare 1945-lakefront home on Lake Howard along Winter Haven's highly sought-after Chain of Lakes. This central Florida waterfront property offers a 2BR/1BA main home plus a separate 1BR/1BA guesthouse currently used as a rental. The breezeway, (laundry rm), has a doorway from the main house leading into the guesthouse that has been sealed off, but could easily be opened again if a buyer wanted to merge the guesthouse into becoming part of the main home. The historic charm here is truly one of a kind w/ original hardwood floors running through much of the home, arched doorways between the rooms, & even the original front door w/ its antique turn-key doorbell. The living rm is anchored by a wood-burning fireplace w/ deep built-in shelving on each side, while large sweeping windows frame views of Lk Howard. The Florida rm/sun rm features wall-to-wall wrap-around windows, tile floor & a built-in window seat w/ storage, offering panoramic lake views & beautiful sunsets. An ornate stained glass divider leads from the sun rm into the dining rm, which showcases a stunning hand-painted mural of Old Florida lakefront scenery w/ the same blue herons, coots & anhingas you'll see right outside. The bathroom features an arched, tiled walk-in shower w/ a frameless glass enclosure. The spacious kitchen offers tile floors, tile countertops, a gas range, white cabinetry, a pantry & a breakfast-nook area w/ French doors that lead to the separate laundry rm, which features vintage mosaic tile floors & direct access to the brick walkway & the generously sized wrap-around wooden sun deck. The large .35-acre lot offers room for a garden, pool, or a private outdoor retreat. Just behind the main home, the guesthouse has its own charm, w/ a checkerboard woven wood ceiling & painted vintage mosaic tile floors. Its living area has sliders leading to its private covered patio. The guesthouse kitchen includes wood cabinetry, & tile floors while the tiled bathroom offers a step-in shower. The same tenant has called it home for approx. 4 years & rents month-to-month for $800/mo, making it a reliable income-producing property, a private space for guests, or a future extension of the main home. There are 3 carports plus 2 storage rooms. Across the street, your private lakefront features a boat dock w/ electric, newer decking & a boatlift that just needs a motor. This fixer-upper needs some TLC, but w/ this much character & potential on the Chain of Lakes, it is a rare chance to restore a true piece of Winter Haven history. All measurements are approx. & all info should be confirmed by buyer.

1501 N Lake Howard Drive, Winter Haven

417 Avenue G  Se, Winter Haven
$375,000
3 Beds ⋅ 2 Baths ⋅ Lawing Sub SubDv. ⋅ 33880 Zip Code
MORE SPACE, MORE FLEXIBILITY, MORE POSSIBILITIES. Discover the charm and potential of this inviting property located in Winter Haven! Featuring 3 bedrooms and 2 bathrooms, this home offers a comfortable and functional layout with no carpet throughout, making everyday living and maintenance a breeze. A standout feature is the additional flexible space with its own full bathroom, ideal for accommodating guests, creating a private home office, or enjoying extra room for your personal needs. Step outside and discover an expansive, fully fenced backyard, offering a wonderful setting for outdoor entertaining, gardening, weekend gatherings, or simply relaxing under the Florida sunshine. A convenient covered carport adds everyday practicality. Whether you're looking for comfortable indoor living, versatile extra space, or a generous outdoor area to enjoy, this property brings it all together. **A unique opportunity with space to make it your own! Schedule your private showing today and experience everything this property.

417 Avenue G Se, Winter Haven

Island Way, Winter Haven
$375,000
Orchid Spgs SubDv. ⋅ 33884 Zip Code
PRICE REDUCED!!! This is an incredible opportunity to own 5 acres of pristine, buildable land in one of Winter Haven’s most exclusive gated residential communities. Currently comprised of five separate parcels that will be combined and conveyed as one expansive 5-acre homesite, this property offers the privacy, space, and beauty rarely found in today’s market. Surrounded by majestic grandfather oaks and gorgeous dappled sunlight, the land is flat, cleared, and ready for construction. Build your custom dream estate and enjoy the tranquility of this picturesque setting. Community requirements include the construction of one single-family residence with a minimum of 2,700 sq ft, ensuring a neighborhood of quality homes. Opportunities like this are truly a unicorn—spacious, private, and located in a stunning setting just minutes from all that Winter Haven entails. This will not last long—call today to schedule your private showing!

Island Way, Winter Haven

3992 Giorgio Drive, Winter Haven
$370,000
4 Beds ⋅ 3 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Under Construction. Brand new, energy-efficient home available by Jan 2027! Entertain guests with ease with an open kitchen which overlooks the dining and great room. First floor flex space can be best used to fit your family's needs. Upstairs primary suite features an oversized 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.

3992 Giorgio Drive, Winter Haven

3035 Buckeye Pointe Drive, Winter Haven
$369,900
4 Beds ⋅ 3 Baths ⋅ Buckeye Pointe SubDv. ⋅ 33881 Zip Code
Welcome to 3035 Buckeye Point Drive, a beautifully refreshed pool home located in the desirable Buckeye Pointe community of Winter Haven. Offering 4 bedrooms, 3 bathrooms, and approximately 2,070 square feet of living space, this spacious home combines a functional layout, modern updates, and the Florida lifestyle buyers are looking for. The home has been freshly repainted inside and out, featuring a modern light gray exterior with crisp trim and a refreshed interior with light gray walls and bright trim throughout. The fresh finishes create a clean, updated, and move-in-ready feel from the moment you arrive. Inside, you'll find high ceilings and a spacious floor plan with plenty of room for everyday living, entertaining, family, and guests. Step outside to your private screened-in pool and enjoy your own backyard retreat—perfect for relaxing, entertaining, or enjoying Florida weather year-round. Located in Winter Haven, Buckeye Pointe offers convenient access to shopping, dining, schools, medical facilities, recreation, and major roadways connecting you throughout Central Florida. Whether you're looking for a primary residence, vacation home, or investment opportunity, this updated 4-bedroom, 3-bath pool home offers an excellent combination of space, comfort, location, and value. Don't miss the opportunity to make 3035 Buckeye Point Drive your own!

3035 Buckeye Pointe Drive, Winter Haven

218 Hartridge Hills Drive, Winter Haven
$369,000
3 Beds ⋅ 2 Baths ⋅ Hartridge Hills SubDv. ⋅ 33881 Zip Code
Virtually Staged. Some homes are built to follow trends. Others are built to stand the test of time. Welcome to 218 NW Lake Hartridge Drive, where timeless craftsmanship meets beautiful renovations in one of Winter Haven's established gated communities, complete with private access to the Chain of Lakes. Built in 1988, this custom home offers something becoming increasingly difficult to find: character, quality construction, and architectural details that make a home truly special. From the moment you step inside, soaring ceilings, exposed wood beams, solid wood doors, and matching wood baseboards create a sense of warmth and character that simply cannot be replicated in today's cookie cutter construction. Thoughtfully renovated from top to bottom, this home beautifully balances its original charm with the comforts of modern living. Luxury vinyl plank flooring, fresh interior paint, updated lighting, and smooth ceilings provide a fresh, inviting atmosphere throughout. The beautifully remodeled kitchen features custom wood cabinetry, granite countertops, and matching Whirlpool appliances, while both bathrooms have been tastefully updated with beautiful tile finishes, wood vanities, Delta fixtures, and Kohler toilets. The spacious split bedroom floor plan offers privacy and flexibility, while the primary suite features new carpeting. Imagine the holidays here. A Christmas tree beneath those beautiful ceilings, Thanksgiving dinner surrounded by family, and the laughter of friends filling the living spaces. This is the kind of home that invites you to slow down, gather together, and create memories that last for generations. A home that feels curated rather than decorated, where the character is already there and the next chapter is yours to write. And while the character may be timeless, the improvements are anything but dated! A NEW ROOF installed in March 2026, new double insulated windows, new water heater, fresh exterior paint, updated irrigation, and professional landscaping provide peace of mind for years to come. The home has also passed a recent four point inspection. An attached two car garage and generous laundry room storage add everyday practicality. Beyond the front door, you'll discover an established gated neighborhood with mature surroundings and a wonderful sense of pride of ownership. Residents enjoy a private community dock and boat ramp with access to Winter Haven's beautiful Chain of Lakes, offering endless opportunities to enjoy life on the water. Even better, the HOA is just $150 per month and includes lawn mowing and fertilization, allowing you to spend more time enjoying your home and less time maintaining the lawn. If you've been searching for a home with substance, character, and quality, without sacrificing the updates and conveniences of today, this may be exactly what you've been waiting for. Because some homes aren't meant to look like every other home on the street. And that's precisely what makes them special. Welcome home to 218 NW Lake Hartridge Drive.

218 Hartridge Hills Drive, Winter Haven

5385 Hogan Lane, Winter Haven
$369,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph I SubDv. ⋅ 33884 Zip Code
Welcome to this stunning Biscayne-model home located at 5385 Hogan Lane, Winter Haven, Florida 33884, within the highly desirable Lake Ashton, a Premier Florida Retirement community in Central Florida. This beautifully maintained property offers premium upgrades, functional spaces, picturesque lake views and gorgeous Florida sunsets. Premium Interior Features include: Gourmet Kitchen with 42" cherry cabinetry with modern crown molding and large metal handles, granite countertops, a breakfast bar, an elegant tile backsplash, and window above the sink. The kitchen cabinet layout includes several banks of drawers, a stainless steel sink and an enlarged open area that flows seamlessly into the breakfast nook. The dedicated den is a highly functional space complete with a built-in Murphy bed and custom desk complex, perfect for a home office or guest room. The wall unit also has a desk that folds out easily. The Primary Suite Bath features comfort height cabinetry, granite countertops, upgraded mirrors and lighting fixtures, a garden tub, and a glass shower door enclosure. The guest bathroom is similarly appointed with a comfort height cabinet, granite counter, upgraded mirrors, and a shower/tub combo. You'll find Upgraded Flooring in the main living, dining, and dinette areas with bamboo flooring, while the kitchen, bathrooms, laundry room and den have tile flooring; plush carpeting is in the bedrooms. This home has a desirable outdoor living area. Relax on the large, screened lanai with tile floor while enjoying beautiful water views and sunsets. A professionally laid paver walkway connects the garage directly to the lanai. This home has double-paned windows, solar tubes for abundant natural light throughout the kitchen, bathrooms, laundry room, and den, and ceiling fans in every room. The Expanded Garage Space is a bonus. The generous double car garage has built-in cabinetry, an extra-long dedicated golf cart garage (8'5x29'11), a utility sink, an exterior window, and a pull-down ladder for attic storage. Additional Home Highlights: Roof Replaced 2025, A/C (2017), Separate Irrigation Meter, Extended Birdcage with Tile Flooring. Located in Lake Ashton, a Florida Retirement community offering Resort style amenities and planned activities. Lake Ashton, a 55 community in Florida, has (2) 18- Hole Golf Courses, Pro Shop, Main Clubhouse with Movie Theater, Bowling Lanes, Grand Ballroom, Card, Craft and Billiards, Outdoor Pool, Bocce, Shuffleboard, Tennis and Fitness Center. The Health and Fitness Center has an Indoor Pool, Card, Craft and Billiards, Multi-Purpose Room, Media Center, Indoor 1/2 Court Basketball, Indoor Full Court Racquetball, Pickle Ball courts and MORE! One Year Home Warranty Included. Call today to tour this home.

5385 Hogan Lane, Winter Haven

1734 Hummingbird Road, Winter Haven
$368,720
4 Beds ⋅ 3 Baths ⋅ Harmony On Lake Eloise SubDv. ⋅ 33884 Zip Code
Under Construction. Welcome to the Campbell, a stunning four-bedroom, two and a half bathroom home located in the heart of Winter Haven, Florida at our Harmony at Lake Eloise community. A beautiful patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, quartz countertops, dining area and a walk-in pantry for extra storage. Ample windows and a set of sliding glass doors allow lighting into the dining area and luxury vinyl plank flooring throughout is stylish and charming. The first floor also features a powder bathroom off the living area for convenience. As we head up to the second floor, we are greeted with bedroom one that features an en-suite bathroom with a double vanity and a spacious walk-in closet providing substantial space for storage. Three additional bedrooms, a full bathroom, and a laundry area are located on the second floor. Like all homes in Harmony at Lake Eloise, the Campbell includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. With its spacious layout and contemporary finishes, the Campbell in Harmony at Lake Eloise provides the perfect blend of style and functionality. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1734 Hummingbird Road, Winter Haven

How much is your home worth?

Get instant property value now!