Winter Haven FL Historical Real Estate, Homes for Sale

3 Beds ⋅ 1 Baths ⋅ Idyl Ridge View SubDv. ⋅ 33881 Zip Code

Virtually Staged. Step into this charming 3-bedroom, 1-bath home in the heart of Winter Haven, offering comfort, convenience, and classic Florida living. The well-appointed kitchen features abundant cabinetry, providing excellent storage and functionality for everyday cooking and gathering. Enjoy practical features throughout, including a 1-car carport, carpeted bedrooms for added comfort. This home is ideally situated near shopping, schools, and local amenities, with easy access to downtown Winter Haven and surrounding Polk County destinations, making everyday living a breeze. Homes offering this blend of value, location, and livability don’t stay available for long. Don’t let this one slip away.

2710 Woodlawn Drive, Winter Haven

$185,000

2 Beds ⋅ 1 Baths ⋅ Parkland Village SubDv. ⋅ 33880 Zip Code

Welcome home to this well-maintained 2-bedroom, 1-bath patio home located in the 55+ community of Parkland Village. This move-in-ready home offers numerous recent updates, including a new roof (December 2025), new windows (2024–2025), new A/C (2022), and a new refrigerator and stove (2026), providing comfort and peace of mind for years to come. Inside, you'll find thoughtful features such as vertical blinds, mirrored closet doors, and storm doors and shutters. The home also includes a private courtyard, perfect for relaxing or entertaining, along with a 1-car carport and a storage closet with a washer and dryer. Residents enjoy access to a recreation building and shuffleboard courts, while the low monthly HOA fee of just $110 includes grounds maintenance, making for easy, low-maintenance living. Conveniently located near shopping, banks, and restaurants, this home offers the perfect combination of comfort, convenience, and affordability. Don't miss this opportunity—schedule your private showing today!

790 Avenue Q Se, Winter Haven

$930,000

Eastwood Sub SubDv. ⋅ 33884 Zip Code

This 1.05-acre commercial property is ideally located on Dundee Road in Winter Haven, Florida, offering excellent visibility and a wide range of potential commercial uses. With an average daily traffic count of approximately 19,000 vehicles, the site provides strong exposure for businesses. Essential utilities, including water, sewer, electricity, telephone, and high-speed internet, are available at the property, making it ready for development. Conveniently situated just 7 minutes from both US 27 and Downtown Winter Haven, the property also offers easy access to Interstate 4, approximately 35 minutes away. Adding to its appeal, a brand-new Publix shopping center is located at the corner of Dundee Road and Country Club Road, contributing to the area's continued growth and increasing commercial activity. 1,550 SQ/FT house on the property.

Winter Haven

$399,999

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 2,287 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

$224,500

4 Beds ⋅ 2 Baths ⋅ Hills Lake Elbert SubDv. ⋅ 33881 Zip Code

Welcome to this spacious 4-bedroom, 2-bathroom home offering a wonderful blend of timeless character, flexible living space, and outstanding outdoor potential. From its classic brick exterior with charming blue accents to the energy-efficient rooftop solar panels, this property is designed for both comfort and value. Inside, you'll find a bright and inviting living area with durable tile flooring and a decorative leaded-glass front door that creates a warm first impression. The spacious eat-in kitchen features crisp white cabinetry, generous counter space with dark countertops, and plenty of room for everyday meals and gatherings. A versatile BONUS FLEX ROOM showcases rich pine wood paneling, built-in shelving, and direct access to the backyard, making it ideal as a family room, media room, game room, home office, or hobby space. The primary bedroom, flex room, and second bedroom feature comfortable carpeting. The four well-sized bedrooms provide flexibility for families, guests, or remote work needs, while the functional layout offers comfortable everyday living. Step outside to discover a large, FULLY FENCED BACKYARD with endless opportunities to create your own private retreat. The expansive concrete patio with brick accents provides the perfect setting for outdoor dining, entertaining, weekend barbecues, or simply relaxing under the Florida sunshine, with plenty of additional yard space for a garden, play area, or future outdoor enhancements. Major updates include a 2015 water heater, the roof has been updated in 2022 and a 2012 HVAC system, plus the added value of a SECOND BACK UP HVAC UNIT that is not hooked up to the house. Ideally located in the heart of Winter Haven, this home places you just minutes from Downtown Winter Haven, the renowned Chain of Lakes, Chain of Lakes Park, Polk State College, and LEGOLAND® Florida Resort. A NEWLY BUILT SCHOOL IS LOCATED just a few blocks away, while the recently renovated walking, biking, and running trail surrounding beautiful Lake Elbert offers an excellent opportunity to enjoy an active outdoor lifestyle. Everyday conveniences are within easy reach, including Publix, Walmart, Lowe's, shopping, dining, and medical facilities. Winter Haven Hospital is just 7 minutes away, Santiago's Market is approximately 10 minutes away, while Winter Haven Regional Airport and Auburndale Speedway are both just a 17-minute drive. With quick access to US-17, US-27, and the Polk Parkway, commuting to Lakeland, Orlando, and Tampa is simple. Blending vintage charm with modern comforts and an unbeatable location close to the area's top amenities, recreational opportunities, and everyday conveniences, this property is the perfect place to call home.

1500 Avenue H Ne, Winter Haven

$259,000

3 Beds ⋅ 2 Baths ⋅ Deer Lake Terrace Sub SubDv. ⋅ 33881 Zip Code

Welcome to this charming 3-Bedroom, 2-bath home in the heart of Winter Haven! This property offers comfortable living with a functional layout, a welcoming front porch, and a private in-ground pool that's perfect for relaxing or entertaining family and friends. Fully fenced yard. Conveniently located near shopping, dining, schools, and major roadways. DONT miss this opportunity - schedule your showing today!

3334 Avenue J Nw, Winter Haven

$255,000

3 Beds ⋅ 1 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code

Welcome to this newly remodeled 3-bedroom, 1-bath home. This charming home has been thoughtfully updated and is move-in ready, offering a perfect blend of modern finishes and comfortable living.Step inside to discover a bright, inviting interior featuring fresh updates throughout. The spacious living area flows into a functional kitchen with updated cabinetry, countertops, and appliances, making it ideal for both everyday living and entertaining. The three well-sized bedrooms provide plenty of space for family, guests, or a home office, while the renovated bathroom showcases stylish, contemporary finishes.Outside, you'll find a generous yard with room to relax, garden, or entertain. Conveniently located near schools, shopping, dining, parks, and major roadways, this home offers easy access to everything Winter Haven has. Don't miss this opportunity to own a beautifully remodeled home that's ready for its next owner. Schedule your private showing today!

109 2nd Jpv Street, Winter Haven

$235,000

4 Beds ⋅ 2 Baths ⋅ Jan Phyl Village Unit 10 SubDv. ⋅ 33880 Zip Code

Discover the value you've been searching for! This affordably priced 4-bedroom, 2-bath home offers the space today's buyers need without stretching the budget. Inside, you'll find tile flooring throughout, a welcoming formal living room, plus a spacious family room just off the kitchen—perfect for everyday living and entertaining. The kitchen also features a dedicated dining area, creating a comfortable gathering space for family and friends. A generous utility room with additional storage helps keep everything organized, while outside you'll appreciate the fully fenced backyard, offering room for pets, play, or weekend BBQs. A large concrete pad with an existing storage shed provides excellent space for tools, hobbies, or outdoor equipment. Best of all, there's no HOA, giving you added flexibility and fewer restrictions. If you've been searching for an affordable home with four bedrooms, functional living space, and a spacious backyard, this one deserves a spot at the top of your list!

506 Thomas Avenue, Winter Haven

$215,000

3 Beds ⋅ 1 Baths ⋅ West Winter Haven Rep SubDv. ⋅ 33880 Zip Code

Charming and move-in-ready 3-bedroom, 1-bath home situated on a spacious lot in the heart of Winter Haven! This well-maintained residence features an open-concept living area, updated flooring, and a bright kitchen designed for everyday comfort. Recent improvements include updated windows and roof, offering added peace of mind. Enjoy a large fenced backyard with plenty of room for pets, play, gardening, or outdoor entertaining. The extended parking area provides space for multiple vehicles, a boat, or an RV. Conveniently located near shopping, dining, schools, parks, Lake Howard, and major roadways, with easy access to LEGOLAND Florida Resort and other local attractions. No HOA restrictions make this property an excellent opportunity for homeowners or investors alike.

2508 Avenue A Sw, Winter Haven

$379,900

3 Beds ⋅ 2 Baths ⋅ Lesnick Park SubDv. ⋅ 33880 Zip Code

Imagine the possibilities! Offering approximately 1,890 square feet of finished living area along with an additional 1,622 square feet of permitted functional space, the property provides approximately 3,512 total square feet, under roof, of combined building area. The expansive open living areas provide endless possibilities—whether you're envisioning an oversized primary suite, game room, home office, music studio, fitness space, or the ultimate man cave or she shed. Unlike many homes with fixed layouts, this property's generous footprint invites you to customize the space to fit your lifestyle. Step outside to enjoy your own private retreat featuring a solar-heated 20' x 40' pool, beautiful paver pool deck, spacious fenced backyard, circular driveway, and no HOA—all in an established neighborhood surrounded by beautiful lakefront homes. A unique 3-car garage configuration provides exceptional flexibility. The oversized 23' x 25' two-car garage includes an adjoining workshop or storage area, while the separate single-car garage with a built-in closet sits adjacent to the utility room, making it ideal for hobbies, storage, a home gym, or recreational equipment. If you've been searching for a home with space, versatility, and room to make it your own, this is one you won't want to miss.

906 Avenue M Se, Winter Haven

$189,900

2 Beds ⋅ 2 Baths ⋅ Jarvis Heights SubDv. ⋅ 33881 Zip Code

Great location just needs some TLC. This 1,110 sq.ft. home is located in the heart of Winter Haven minutes to downtown hospital and walking distance to Polk State College. Featuring 2 bedrooms and 2 bathrooms, this home has undergone some renovations but looking for someone to finish off with their own touches. The property features a new metal roof, new luxury. vinyl flooring, split unit (2022), and full electric and plumbing in 2022. The kitchen has also been updated with new cabinets and stainless appliances. Outside you have plenty of possibilities. The detached building is ready to be made into a mother-in-law suite or perfect man cave. Large back porch and chicken coop are other perks of this listing. Call or text to see it today! *Agents, please read MLS remarks.*

650 9th Street Ne, Winter Haven

$269,900

3 Beds ⋅ 2 Baths ⋅ Fla Highlands Co Sub SubDv. ⋅ 33884 Zip Code

Welcome to 118 Browning Circle, Winter Haven, FL, where comfort, thoughtful updates, and an unbeatable location come together to create the perfect place to call home. Nestled in a well-established neighborhood with no HOA, this beautifully maintained 3-bedroom, 2-bath home is truly move-in ready and offers the ideal blend of functionality and charm. Step inside to a spacious, open great room with attractive luxury vinyl flooring, creating a warm and inviting space for everyday living, family gatherings, or entertaining guests. The desirable split-bedroom floor plan provides added privacy, while the versatile third bedroom with built-in shelving makes an excellent home office, craft room, or guest bedroom. The kitchen offers abundant cabinet and counter space, a convenient pass-through window, and a cozy breakfast area, making meal preparation both practical and enjoyable. Just beyond, you'll fall in love with the expansive Florida Room, providing additional living space perfect for relaxing, entertaining, a game room, or simply enjoying Florida living year-round. The spacious primary suite features a private en-suite bathroom with a walk-in shower, while the indoor laundry room offers exceptional storage with multiple closets to help keep everything organized. Outside, the fully vinyl-fenced backyard creates your own private retreat. Enjoy beautiful mature landscaping, and a brick paver patio that's perfect for morning coffee, weekend barbecues, or quiet evenings outdoors. This home has been meticulously maintained and thoughtfully updated, giving buyers peace of mind for years to come, including: HVAC (2024), vinyl privacy fence (2024), attic insulation (2024), house replumbed (2022), brick paver patio (2023) Additional features include a spacious two-car garage with built-in shelving for extra storage and organization. Location is everything, and this home delivers. Just two blocks away, you'll enjoy access to the neighborhood park featuring a basketball court, playground, fishing pier, and community boat ramp. Plus, you're only minutes from LEGOLAND Florida Resort, shopping, restaurants, schools, medical facilities, and major roadways, making everyday convenience part of your lifestyle. If you've been searching for a home that offers space, updates, privacy, and an exceptional location, 118 Browning Circle is one you won't want to miss. Schedule your private showing today before it's gone!

118 Browning Circle, Winter Haven

$409,900

4 Beds ⋅ 3 Baths ⋅ Eloise Woods Lake Roy Unit SubDv. ⋅ 33884 Zip Code

Located in one of Southeast Winter Haven's most desirable neighborhoods, just minutes from the Chain of Lakes and Lake Summit boat ramp, this beautifully updated 4-bedroom, 3-bath pool home offers nearly 2,500 square feet of living space with **no HOA**.Designed with flexibility in mind, the home features two spacious primary suites, multiple living areas, and a beautifully remodeled kitchen with quartz countertops, soft-close cabinetry, stainless steel appliances, and a workstation sink. Step outside to the screened lanai overlooking the private pool and enjoy the fully fenced backyard—perfect for entertaining, pets, and everyday living.Major updates include a NEW ROOF(2019), HVAC (2019), HOT WATER HEATER (2019), primary bathroom remodel (2019), kitchen remodel (2021), pool heater (2022), pool pump (2024), front and backyard irrigation system (2024), and guest bathroom remodel (2025)Offering quality updates, generous living space, and an exceptional location! Schedule your private showing today!

144 Beverly Dr, Winter Haven

$482,500

3 Beds ⋅ 2 Baths ⋅ Winterset Gardens SubDv. ⋅ 33884 Zip Code

Virtually Staged. Rarely does a home this unique come to market! Situated on a spacious .30-acre lot directly across the street from beautiful Lake Winterset, this fully renovated 3-bedroom, 2-bath mid-century modern pool home offers incredible character, modern updates, and NO mandatory HOA or CDD. An optional neighborhood HOA of just $100 per year provides access to the community boat ramp, connecting you to the renowned Winter Haven Chain of 22 Lakes, one of Central Florida's premier destinations for boating, fishing, and watersports. Unlike nearly any other Florida home, this property features an impressive 300+ square foot basement, a rare find that offers endless possibilities as a wine cellar, hobby room, workshop, fitness area, or additional storage. The home's distinctive architectural design is complemented by spectacular views of Lake Winterset from the living and dining rooms, where sliding glass doors open to a charming wraparound front porch—the perfect place to enjoy your morning coffee while taking in the peaceful lake scenery. Upstairs, a spacious bonus room provides flexibility as a potential fourth bedroom, media room, home office, or second living area and includes a private balcony overlooking the front of the property and the lake. The beautifully updated kitchen is designed for both everyday living and entertaining with quartz countertops, a center island, pantry, recessed lighting, tile backsplash, reverse osmosis system, garbage disposal, a window overlooking the screened pool, and a premium 2022 Samsung Bespoke appliance suite. The home's thoughtful split layout places all three spacious bedrooms down a private hallway away from the main living spaces. Wood-look tile flooring flows throughout the main living areas, while luxury vinyl plank flooring extends through the bedrooms, bathrooms, and upstairs bonus room. The spacious primary suite features dual vanities and a beautifully remodeled walk-in shower. Additional conveniences include an indoor laundry closet with the washer and dryer included, and a two-car garage. Step outside to your oversized screened, chlorinated pool complete with a diving board and removable safety fence, creating the perfect backyard retreat for entertaining family and friends year-round. Major improvements provide added peace of mind, including a new roof in 2025, a new pool pump and well pump in 2025, new A/C ductwork and attic insulation in 2025, windows replaced in 2019, A/C replaced in 2019, water heater replaced in 2019, and new appliances installed in 2022. Ideally located just a short drive from Disney, Universal, LEGOLAND, and other Central Florida attractions, this one-of-a-kind home combines timeless mid-century modern architecture, extensive modern updates, a rare basement, beautiful lake views, access to the Winter Haven Chain of Lakes, and a lifestyle that is truly hard to find. Don't miss this rare opportunity to own one of the area's most distinctive homes overlooking beautiful Lake Winterset.

6704 Winterset Gardens Road, Winter Haven

$99,000

2 Beds ⋅ 1 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code

Peaceful oasis in a premier 55+ community! This lovely 2 bedroom, 1 bath second-floor condo in Winter Haven Harbour Apartments offers a perfect blend of comfort, functionality, and an active, low-maintenance lifestyle. Inside, you will find a spacious living room that flows effortlessly into a dedicated dining room, and a galley-style kitchen that maximizes counter space and storage, making meal preparation a breeze. Step onto your private balcony, where you can enjoy your morning coffee, read a book, or soak in the serene views. This wonderful active community offers fantastic resort-style perks, including a sparkling heated community pool, an active community center, and shuffleboard courts for fun with friends and neighbors. This home provides the ideal setting for your next chapter. Don't miss out, schedule your appointment today.

1700 6th St Nw Unit C24, Winter Haven

$149,900

2 Beds ⋅ 2 Baths ⋅ Spring Lake Towers SubDv. ⋅ 33881 Zip Code

Enjoy maintenance-free lakefront living in this 2-bedroom, 2-bathroom condominium located in the highly sought-after Spring Lake Towers, a premier 55+ active adult community in the heart of Winter Haven. Updated in 2020, this inviting residence offers BREATHTAKING VIEWS OF SPRING LAKE, part of the scenic Spring Lake Meander, and a bright, open living space that feels like an indoor lanai, where walls of windows create the perfect setting to relax while overlooking the tranquil water. Both the primary bedroom and the second bedroom have direct access to this enclosed lakefront space, creating a seamless connection to the serene waterfront and providing the perfect spot to enjoy your morning coffee, unwind with a book, or simply take in the picturesque views of Spring Lake throughout the day. The updated kitchen is designed for both style and function, featuring soft-close cabinetry, porcelain countertops, recessed lighting, a decorative tile backsplash, a convection oven, and a convenient center island cart. Luxury vinyl flooring flows throughout the main living areas, while the bedrooms offer the comfort of carpet. The spacious primary suite features a walk-in closet and an ensuite bath, while the secondary bathroom has been tastefully updated with a beautifully tiled glass-enclosed shower. The all-inclusive condo fee provides exceptional value, covering cable TV, high-speed internet, water, sewer, trash removal, exterior building maintenance, roof maintenance, building insurance, reserve funds, on-site management, groundskeeping, and assigned covered parking. Residents enjoy an impressive selection of community amenities, including a waterfront in-ground concrete pool, fitness center, recreation room with a full kitchen, library, game area, shuffleboard courts, laundry facilities, private boat docks, and a year-round social calendar. Take advantage of the community's private dock, where boat slips are available on a first-come, first-served basis for a minimal monthly fee, offering convenient access to Spring Lake Meander for boating, fishing, or simply enjoying the peaceful waterfront setting. Ideally located just minutes from historic downtown Winter Haven, the renowned Chain of Lakes, shopping, dining, medical facilities, golf courses, and LEGOLAND® Florida Resort, this waterfront condo offers the perfect blend of low-maintenance living, spectacular views, and an active Florida lifestyle.

700 Mirror Terrace Nw Unit 511, Winter Haven

$210,000

3 Beds ⋅ 1 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

**Calling all lake lovers!** Discover this charming 3-bedroom, 1-bath home situated on **nearly half an acre** in the heart of Winter Haven. Featuring a functional floor plan, a spacious yard, and **private rear access**, this property offers endless possibilities for outdoor entertaining, gardening, parking boats, RVs, or work vehicles, or even future expansion. No HOA. Conveniently located near shopping, dining, schools, and major roadways, you'll also enjoy easy access to Central Florida's top attractions. **LEGOLAND® Florida Resort is approximately 15 minutes away**, **Walt Disney World® Resort is about 35–40 minutes away**, and **Universal Orlando Resort** and **SeaWorld Orlando** are both within **45–50 minutes**, making this home an excellent choice for both homeowners and investors. Boating and fishing enthusiasts will appreciate the close proximity to several of Winter Haven's beautiful lakes, with a public boat ramp located just half a mile away, making it easy to enjoy Florida's year-round outdoor lifestyle. Whether you're a first-time homebuyer, looking to downsize, or searching for a fantastic investment opportunity, this property offers comfort, convenience, generous outdoor space, and tremendous potential. **Schedule your private showing today and discover everything this home has to offer!**

3328 Avenue T Nw, Winter Haven

$274,990

3 Beds ⋅ 2 Baths ⋅ Leisure Shores SubDv. ⋅ 33881 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2-bath home offering approximately 1,627 square feet of comfortable living space in the established Leisure Shores community of Winter Haven. Situated on a spacious 0.22-acre lot, this property is packed with features both inside and out. Step inside to an open floor plan with easy-to-maintain laminate flooring throughout, an updated kitchen featuring granite countertops, newer cabinetry, stainless steel appliances, and plenty of space for everyday living and entertaining. Energy-efficient double-pane windows and an updated sliding glass door help enhance comfort throughout the home. The backyard is designed for enjoying Florida living, complete with a screened lanai, an above-ground pool, a large side deck, and a fully fenced yard that’s perfect for relaxing or hosting family and friends. Need extra space? This property offers multiple detached structures, including a spacious air-conditioned shed that’s ideal for a home office, hobby room, gym, studio, or workshop, plus an additional storage shed for tools and equipment. For those with recreational vehicles or extra toys, you’ll appreciate the dedicated RV parking area with electrical hookup, along with a covered carport for everyday parking. Conveniently located near shopping, dining, schools, and everything Winter Haven has to offer, this home combines comfort, versatility, and outdoor living in one exceptional package. Schedule your private showing today!

2021 Oliver Place, Winter Haven

$109,900

3 Beds ⋅ 2 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

Bring your next project to this really nice house!!!!

3915 Avenue Q Nw, Winter Haven

$315,000

4 Beds ⋅ 2 Baths ⋅ Howard Cannon Park Resub SubDv. ⋅ 33881 Zip Code

Located on a spacious corner lot in the heart of Winter Haven, this income-producing duplex offers an unbeatable combination of location, and long-term potential. One unit is currently rented for $1,300 on a month to month lease. The other unit is currently vacant. Featuring a brand-new roof and easy access to Winter Haven’s famous Chain of Lakes, including Lake Howard and Lake Cannon. Residents can enjoy boating, fishing, and waterfront dining. Ideally situated only about 8 minutes from Downtown Winter Haven, residents can also enjoy local restaurants, shops, entertainment, and community events while still having quick access to major roadways for an easy commute throughout Polk County. The property also offers convenient access to nearby schools, including Inwood Elementary just 2 minutes away, Westwood Middle approximately 4 minutes away, and Winter Haven Senior High around 8 minutes away. Whether you’re looking to expand your investment portfolio or secure a property in one of Central Florida’s fastest-growing lakefront communities, This property has exceptional value with its prime location, recent improvements, and proximity to Winter Haven’s iconic lakes and downtown district.

2097 Avenue H Nw, Winter Haven

$160,000

3 Beds ⋅ 1 Baths ⋅ Florence Village SubDv. ⋅ 33881 Zip Code

Investor Alert! This solid 3-bedroom, 1-bathroom block home sits on a spacious lot in an established neighborhood with NO HOA. Fully fenced from front to back, the property offers a massive backyard and a generous front yard, complete with a charming enclosed front porch. Capitalize on excellent bones and recent big-ticket upgrade-brand-new roof installed in 2025. While the interior needs some cosmetic updating, it represents the ideal canvas for a savvy investor looking for a high-yield rental or a flip project. Enjoy a prime location just minutes from a local lake, park, community recreation center, sought-after magnet schools, and convenient public transit. Opportunities like this don't last long, so bring your vision and make an offer before it’s too late!

1903 3rd Street Ne, Winter Haven

$174,900

2 Beds ⋅ 2 Baths ⋅ Lake Shipp Heights SubDv. ⋅ 33880 Zip Code

Welcome Home! If you've been dreaming of homeownership but thought it was out of reach, this could be the opportunity you've been waiting for. This charming 2-bedroom, 1.5-bath home also features a versatile bonus room that could be used as a 3rd bedroom, home office, playroom, hobby room, or extra storage space. Situated in a well-established Winter Haven neighborhood, this home offers the perfect chance to begin building equity instead of paying rent. One of the standout features is NO HOA, giving you the freedom and flexibility that so many buyers are looking for. The fully fenced yard provides a great space for pets, kids, entertaining, or simply relaxing in your own private outdoor space. Whether you're a first-time homebuyer looking for a place to call your own or an investor searching for your next rental property, this home offers plenty of potential. The functional layout, cozy feel, and flexible living space make it easy to envision making it your own over time. Conveniently located near shopping, restaurants, schools, and major roadways, you'll enjoy easy access to everything Winter Haven and the surrounding area has to offer. Even better, the seller will be installing a BRAND-NEW ROOF prior to closing, giving the new owner added peace of mind and one less major expense to worry about. Your first home doesn't have to be your forever home—it just has to be your start. Come see the possibilities this home has to offer!

112 Palm Drive, Winter Haven

$78,800

2 Beds ⋅ 1 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code

Virtually Staged. Perched on the third floor, Unit A38 at Winter Haven Condominiums offers the perfect combination of privacy, comfort, and peaceful views. As a desirable end unit, you'll enjoy extra windows that fill the home with natural light along with added privacy from neighboring units. Best of all, elevator access means you can enjoy the top-floor location without worrying about the stairs. Inside, the condo has been thoughtfully updated with newer flooring, fresh interior paint, and modern kitchen cabinetry featuring soft-close doors, creating a bright, inviting space that's truly move-in ready. Just outside your front door, the screened breezeway becomes an extension of your living space. Sip your morning coffee as the day begins, relax with a good book in the afternoon, or unwind in the evening while enjoying Florida's warm breeze and peaceful surroundings. Life here is about more than just the condo. Cool off in the community pool, enjoy a friendly game of outdoor shuffleboard, or take advantage of the community clubhouse, a comfortable, air-conditioned gathering space designed for both relaxation and entertainment. Inside, you'll find a pool table, indoor shuffleboard, fitness equipment, television, and a fully equipped kitchen that's perfect for hosting birthdays, holiday gatherings, game nights, or casual get-togethers. Just bring your favorite food, invite your family and friends, and enjoy the space without the hassle of entertaining at home. Covered, assigned parking is conveniently located just steps from the building, making everyday living even easier. Whether you're looking for a year-round residence or a seasonal escape from colder climates, Unit A38 offers low-maintenance living in a welcoming community where comfort, convenience, and relaxation come together. Schedule your private showing today and experience everything this charming condo has to enjoy.

1700 6th Street Nw Unit A38, Winter Haven

$220,000

3 Beds ⋅ 2 Baths ⋅ Winter Haven Heights SubDv. ⋅ 33881 Zip Code

Welcome to this charming elevated home offering privacy, character, and a bright open-concept layout. Located above the garage, the living space features a spacious balcony that’s perfect for enjoying your morning coffee or relaxing in the evening. Situated on an oversized lot, there’s plenty of room for outdoor activities, gardening, or future possibilities. Just a short distance from the lake and a neighborhood park, this home offers the perfect combination of comfort, convenience, and outdoor enjoyment. Whether you’re looking for your first home, an investment, or a peaceful retreat, this property is one you won’t want to miss!

221 Avenue C Ne, Winter Haven

$180,000

2 Beds ⋅ 1 Baths ⋅ Daniels Sub SubDv. ⋅ 33880 Zip Code

Welcome to this charming, move-in ready 2-bedroom, 1-bath home in the heart of Winter Haven! Freshly painted and filled with natural light, this home offers a comfortable layout, a spacious backyard perfect for entertaining or relaxing, and public water and sewer services for added convenience. The roof has been replaced in recent years, providing additional value and peace of mind. Conveniently located near shopping, dining, schools, parks, and major roadways, this property is an excellent opportunity for first-time homebuyers, downsizers, or investors. Schedule your private showing today!

139 Avenue G Se, Winter Haven

$235,000

2 Beds ⋅ 2 Baths ⋅ Yonnally W P Resub SubDv. ⋅ 33881 Zip Code

Beautifully refreshed home located in a quiet, established neighborhood in Winter Haven! Freshly painted and offering spacious living areas, this property provides a comfortable and inviting layout that’s ready for its next owner. Enjoy the freedom of NO HOA while being conveniently located near shopping, restaurants, schools, parks, medical facilities, and major roadways. A great opportunity for first-time buyers, growing families, or anyone looking for generous interior space in a peaceful residential setting. Buyer to verify all measurements and property information. Contact the listing agent for additional details or to schedule a showing.

629 Avenue A Ne, Winter Haven

$359,000

3 Beds ⋅ 2 Baths ⋅ Hills/Lk Elbert SubDv. ⋅ 33881 Zip Code

Welcome to this spacious and beautifully maintained 3-bedroom, 2-bath home offering over 2,280 square feet of living space on a desirable corner lot in an established Northeast Winter Haven neighborhood near Lake Elbert. With tasteful updates, multiple living spaces, and the rare opportunity to purchase the home completely furnished, this property is move-in ready. The remodeled kitchen serves as the heart of the home, featuring granite countertops, lots of cabinets, a built-in wall oven, cooktop, and microwave—creating the perfect space for preparing meals and entertaining family and friends. The adjoining great room offers an inviting place to gather, highlighted by a charming decorative fireplace that adds warmth and character. One of the home's standout features is the spacious downstairs bonus room with direct exterior access, providing incredible flexibility. Whether you need a media room, game room, home office, fitness area, guest quarters, or potential in-law suite, this versatile space can easily adapt to your lifestyle. Upstairs, the oversized primary suite offers a generous walk-in closet, while two additional bedrooms provide comfortable accommodations for family or guests. Both bathrooms have been tastefully remodeled. Throughout the home you'll find durable wood, ceramic tile, and laminate flooring—there's no carpet to maintain. Additional features include an enclosed sunroom, inside laundry room, abundant storage, a detached workshop/storage building, a fenced backyard, and two convenient parking areas with both a circular driveway and a traditional driveway. Major updates provide added peace of mind, including replacement windows installed in 2021 and a roof replaced in 2018. Being offered completely furnished, this home presents an outstanding opportunity for buyers looking for a primary residence, seasonal Florida retreat, or a property that can be enjoyed immediately. Its flexible floor plan and convenient location also make it an attractive option for those considering long-term rental opportunities. Conveniently located just minutes from Lake Elbert, Polk State College, Winter Haven Hospital, downtown Winter Haven, shopping, restaurants, medical facilities, and the area's beautiful Chain of Lakes, this home combines generous living space, thoughtful updates, and exceptional versatility in one desirable package.

1500 Avenue G Ne, Winter Haven

$231,700

4 Beds ⋅ 2 Baths ⋅ Biltmore Shores SubDv. ⋅ 33881 Zip Code

Well-maintained 4-bedroom, 2-bath home located in the desirable Winter Haven area. This inviting residence features a bright and open floor plan with abundant natural light throughout, creating a warm and comfortable atmosphere. The spacious living and dining areas flow seamlessly, making it ideal for everyday living and entertaining. The kitchen features ample cabinet space and functionality, while the generously sized bedrooms provide comfort and flexibility. The primary suite includes a private bath and generous closet space. Enjoy a private backyard with plenty of space for relaxing, gatherings, or outdoor activities. Conveniently located near shopping, dining, parks, schools, and major roadways, providing easy access to all that Winter Haven and Central Florida have to enjoy.

2390 29th Street Nw, Winter Haven

$210,000

4 Beds ⋅ 2 Baths ⋅ Revised Map Of Fernwood Add SubDv. ⋅ 33881 Zip Code

Welcome to 444 Avenue B, Winter Haven, FL, where charm, convenience, and the Florida lifestyle come together in a location that puts everything within easy reach. Whether you're searching for your first home, a seasonal retreat, or an investment opportunity, this property offers the perfect blend of comfort and accessibility. Ideally situated in the heart of Winter Haven, this home provides quick access to shopping, dining, schools, healthcare, and major roadways, making daily living both convenient and enjoyable. Residents appreciate the neighborhood's established character while remaining just minutes from many of Central Florida's most popular destinations. Known as the "Chain of Lakes City," Winter Haven is home to more than 50 interconnected lakes, offering endless opportunities for boating, fishing, kayaking, paddleboarding, and waterfront recreation. Spend your weekends exploring scenic parks, enjoying lakefront sunsets, or taking advantage of the city's beautiful walking and biking trails. Just a short drive away, historic downtown Winter Haven features locally owned restaurants, boutiques, coffee shops, breweries, and a vibrant calendar of community events throughout the year. The home is also conveniently located near LEGOLAND® Florida Resort, making it a great location for families and visitors alike. Golf enthusiasts will appreciate the area's championship golf courses, while nature lovers can enjoy nearby parks, gardens, and outdoor recreation. Everyday conveniences are close at hand with shopping destinations such as Posner Park, Eagle Ridge Mall, Publix, Walmart, and a variety of national retailers and local businesses just minutes away. Commuters will enjoy easy access to US Highway 17, US Highway 27, and the Polk Parkway, providing convenient travel to Lakeland, Orlando, Tampa, and many of Central Florida's world-famous attractions. Whether you're looking to settle down, expand your investment portfolio, or simply enjoy all that Central Florida has to experience, 444 Avenue B presents an outstanding opportunity to experience the best of Winter Haven living with comfort, convenience, and recreation all close to home.

444 Avenue B Ne, Winter Haven

$185,000

3 Beds ⋅ 2 Baths ⋅ Bookers Sub SubDv. ⋅ 33881 Zip Code

HANDY-MAN SPECIAL LOCATED WINTER HAVEN. PROPERTY IS A 3BEDROOM/2BATHROOM WITH 1,200 SQFT. PROPERTY WAS RENOVATED IN 2022. HOUSE NEEDS WORK.

307 Avenue X Ne, Winter Haven

$169,000

3 Beds ⋅ 2 Baths ⋅ Lake Idyll Estates SubDv. ⋅ 33881 Zip Code

One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 1.5-bathroom home featuring upgraded finishes and a comfortable layout designed for everyday living. The spacious kitchen is equipped with plenty of cabinet and counter space including a refrigerator, microwave and oven, offering both style and functionality for preparing meals and entertaining guests. The home's thoughtful floor plan provides inviting living spaces and a dedicated laundry area for added convenience. A covered carport helps protect your vehicle from the elements while providing easy access to the home. Conveniently located in a quiet neighborhood near shopping, dining, and major roadways, this property offers the perfect combination of comfort, practicality, and accessibility. Whether you're looking for your first home or your next chapter, this Winter Haven residence is a wonderful opportunity. Tour today and don't miss out. Multiple offers - Please submit your highest and best by July 10 at 9AM.

2209 9th Court Ne, Winter Haven

$36,950

2 Beds ⋅ 1 Baths ⋅ Bookers Sub SubDv. ⋅ 33881 Zip Code

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.

314 Avenue Y Ne, Winter Haven

$525,000

4 Beds ⋅ 4 Baths ⋅ Hanna Sub SubDv. ⋅ 33880 Zip Code

Welcome to the Chain Life! Situated on a spacious 0.47-acre lot with no HOA, this beautifully updated lakefront property on Lake Howard offers a rare opportunity to enjoy life on the renowned Winter Haven Chain of Lakes. One of the home's most desirable features is the beautifully remodeled studio-style guest suite with its own private entrance and en-suite bathroom. Complete with a wood-burning fireplace and ample space to add a kitchenette, this versatile space is ideal as a mother-in-law suite, private guest quarters, home office, or game room. This property would make a great short term rental for VRBO or Airbnb! The main residence features 3 bedrooms and 2.5 baths with numerous updates throughout. The renovated kitchen showcases new cabinetry, beautiful granite countertops, a stainless steel range and microwave, breakfast bar seating, and picturesque views of the backyard. Wood flooring flows through the spacious living areas, including formal living and dining rooms, an open kitchen, and a comfortable family room designed for both everyday living and entertaining. The primary suite offers a private en-suite bathroom with a walk-in shower and access to the beautifully remodeled guest bathroom that features a relaxing tub. Fresh interior paint and numerous recent improvements make the home truly move-in ready. Additional features include a well-equipped laundry room with cabinetry, utility sink, and a refrigerator, an oversized 24' x 26' two-car garage with built-in storage closets, rain gutters, a lake-fed irrigation system, a deep driveway with plenty of parking, and two A/C systems installed in 2021 and 2023. Step outside and enjoy the Florida lifestyle. Relax with your morning coffee on the covered front porch overlooking Lake Howard, or entertain family and friends on the expansive concrete patio overlooking the spacious backyard. Across the street, your private dock provides direct access to Lake Howard and the famous Winter Haven Chain of Lakes, connecting you to 20 navigable lakes. Spend your days boating to waterfront restaurants and bars, watching seasonal Legoland fireworks from the water, seeing seaplanes take off from Lake Jessie, or visiting the Moose Lodge for dining and social events, all which area accessible by boat. Conveniently located between Tampa and Orlando, Winter Haven offers easy access to major airports, Gulf and Atlantic beaches, and a vibrant downtown filled with locally owned restaurants, craft cocktail bars, a brewery, boutiques, and a popular weekly farmers market. Don't just live on the water—experience the unmatched lifestyle of the Winter Haven Chain of Lakes. Schedule your private showing today.

1475 S Lake Howard Drive, Winter Haven

$239,900

3 Beds ⋅ 2 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code

Welcome home to this beautifully updated 3-bedroom, 2-bath residence situated on a spacious corner lot in an established neighborhood with NO HOA! Blending timeless charm with modern upgrades, this move-in-ready home offers comfort, style, and exceptional value. Recent improvements include a new roof, new central heating and air conditioning system, updated flooring, fresh interior and exterior paint, new lighting fixtures, and updated appliances, giving the home a fresh, modern feel from top to bottom. Inside, you’ll find bright and inviting living spaces designed for comfortable everyday living. A heated and air-conditioned sunroom with a full bath provides incredible flexibility and can serve as a second living area, home office, hobby room, guest space, or entertaining area. The home also features a convenient indoor laundry room under central heat and air, adding comfort and functionality. Situated on a generous corner lot, the property offers plenty of outdoor space with a private irrigation well, making it easy to maintain a beautiful lawn and garden while keeping watering costs down. There’s ample room for outdoor entertaining, pets, or future additions. Conveniently located near shopping, dining, schools, and everyday amenities, this beautifully refreshed home combines the character of an established neighborhood with the peace of mind that comes from extensive recent updates. Don’t miss your opportunity to own this move-in-ready gem with space, flexibility, and modern improvements throughout!

505 Glad Road, Winter Haven

$225,000

4 Beds ⋅ 3 Baths ⋅ Way Sub SubDv. ⋅ 33880 Zip Code

Under contract-accepting backup offers. Welcome to this charming and versatile 4-bedroom, 2.5-bath home nestled on a quiet cul-de-sac in sought-after Southeast Winter Haven, offering the perfect combination of comfort, functionality, and thoughtful updates. Inside, you'll find a flexible floor plan featuring TWO SPACIOUS LIVING AREAS plus an additional FLEX SPACE that can easily serve as a home office, playroom, fitness room, or media room to fit your lifestyle. The kitchen, remodeled in 2004, offers abundant wood cabinetry and generous counter space while flowing seamlessly into the dining area, making everyday living and entertaining a breeze. The spacious primary suite features its own ensuite bathroom, providing a private retreat, while the additional bedrooms offer flexibility for family, guests, or a home office. Carpet flooring adds warmth and comfort in all bedrooms. Enjoy even more living space in the large screened-in patio overlooking the backyard, complete with a detached storage shed that's ideal for extra storage, hobbies, or lawn equipment. Recent updates provide added peace of mind, including a 2020 ROOF, approximately 2020 A/C system and air handler installed by Tradition Air, NEW PLUMBING (2026), and an electrical panel updated within the last 10 years. The home is connected to city water and city sewer, with electric service provided by TECO. Vacant and ready for its next owner, this property presents an excellent opportunity for a primary residence, seasonal home, or investment. Conveniently located just minutes from downtown Winter Haven, you'll enjoy easy access to shopping, dining, medical facilities, parks, and the city's renowned Chain of Lakes. Commuters will appreciate the proximity to US-17, Cypress Gardens Boulevard, and the Polk Parkway, while nearby attractions, including LEGOLAND® Florida Resort, add to the area's appeal. The peaceful cul-de-sac setting combined with its desirable Southeast Winter Haven location offers the perfect balance of privacy, convenience, and the Florida lifestyle.

650 Avenue N Se, Winter Haven

$410,000

4 Beds ⋅ 3 Baths ⋅ Southeast Terrace SubDv. ⋅ 33880 Zip Code

Move-in ready, No HOA, 4-bedroom, 3-bath pool home with extensive updates and an incredible screened outdoor living space! This spacious, well-maintained home offers the perfect blend of functionality and comfort with both formal and informal living areas, a formal dining room, and a thoughtfully designed loor plan. The updated kitchen features a center island, double sink, abundant cabinet storage, generous counter space, and plenty of room for gathering with family and friends. Beautifully renovated bathrooms and fresh interior paint give the home a modern, welcoming feel. The true showstopper is the expansive screened lanai and pool area. Designed for year-round Florida living, this amazing outdoor retreat features a sparkling pool, multiple seating and entertaining spaces, ceiling fans for added comfort, and plenty of room to host everything from family cookouts to relaxing evenings by the pool. Major improvements provide peace of mind, including a 5-year-old metal roof, new windows throughout with a transferable lifetime warranty, two HVAC systems (one new and one replaced in 2019), a 2-year-old water heater, and 2-year-old vinyl fencing. Conveniently located just off one of Winter Haven's main corridors, you'll enjoy easy access to shopping, dining, medical facilities, schools, and major roadways while coming home to your own private backyard oasis. If you've been searching for space, updates, and an outdoor entertaining area that truly stands out, this home is a must-see!

1826 6th Street Se, Winter Haven

$215,000

3 Beds ⋅ 2 Baths ⋅ Silvercrest Add SubDv. ⋅ 33881 Zip Code

3 bedrooms 2 bath move in ready home. Perfect for starter home or first-time buyer. Newer roof and updated electrical and plumbing throughout and freshly painted.

1328 3rd Street Ne, Winter Haven

$235,000

2 Beds ⋅ 1 Baths ⋅ Tranquility Park Sub SubDv. ⋅ 33880 Zip Code

Welcome home to this adorable 2 bedroom/ 1 bath residence, centrally located in beautiful Winter Haven. Perfect for a first-time home buyer, this charming home offers numerous updates, including a newer metal roof (2023), newer HVAC, complete replumbing (2026), newer vinyl flooring and fresh new interior and exterior paint. Step outside and enjoy the spacious, fully fenced backyard providing privacy and the perfect retreat for pets, entertaining, or simply relaxing. Conveniently located just minutes from downtown Winter Haven and the Polk Parkway, with easy access to both Tampa and Orlando. Don't miss out on a chance to own this charming home. Schedule your private showing today.

1365 Sheridan Street Sw, Winter Haven

$259,000

3 Beds ⋅ 2 Baths ⋅ Lake Add SubDv. ⋅ 33880 Zip Code

Opportunity awaits in the heart of Winter Haven! This 3-bedroom, 2-bath home offers approximately 1,580 square feet of living space on a generously sized lot. Inside, you'll find a functional floor plan with spacious living areas and a layout ready for your personal updates. The kitchen and bathrooms offer the opportunity to customize the home to your own style and preferences. Conveniently located near downtown Winter Haven, shopping, dining, schools, parks, and major roadways, this property provides easy access to everyday conveniences. Schedule your private showing today!

715 Avenue B Sw, Winter Haven

$205,000

2 Beds ⋅ 1 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

Fully remodeled 2-bedroom, 1-bath home in the heart of Winter Haven. This move-in-ready property features a new roof, updated electrical and plumbing, and modern finishes throughout. Situated on a spacious lot with no HOA, it offers both comfort and flexibility. Conveniently located near major roads, shopping, dining, schools, and just minutes from downtown Winter Haven and LEGOLAND Florida Resort, making it an excellent option for homeowners or investors.

3420 Avenue R Nw, Winter Haven

$275,000

3 Beds ⋅ 2 Baths ⋅ Elbert Park Resub SubDv. ⋅ 33881 Zip Code

Welcome home to this charming bungalow-style 3-bedroom, 2-bath residence offering comfort, character along with modern updates. Inside, you'll find durable wood-look tile flooring throughout, beautiful granite countertops and a cozy wood-burning fireplace that creates the perfect gathering space. Major improvements include a new roof and windows in 2020, providing added peace of mind. Step outside to enjoy the fully fenced backyard - ideal for pets, play or entertaining. Best of all, there's no HOA, giving you the freedom to truly make this home your own. Conveniently located in the heart of Winter Haven, with easy access to shopping, dining, schools and everything Central Florida has to offer. Schedule your private showing today!

415 8th Street Ne, Winter Haven

$279,900

3 Beds ⋅ 2 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code

Welcome to this beautifully remodeled 3-bedroom, 2-bath home offering the perfect blend of modern updates and functional living space. In addition to the spacious bedrooms, you'll find a dedicated office/flex room—ideal for working from home, a playroom, or hobby space—as well as a bright Florida room perfect for relaxing or entertaining year-round. This home has been thoughtfully updated with a new roof, new HVAC system, and new blown-in attic insulation, providing comfort and peace of mind for years to come. The interior has been refreshed with stylish finishes, creating a clean, modern feel that's ready for its new owners. Situated on a generously sized lot, the backyard offers plenty of room to create your dream outdoor living space, add a pool, garden, workshop, or simply enjoy the extra space. Conveniently located in the heart of Winter Haven, you'll be just minutes from shopping, restaurants, schools, medical facilities, and major roadways, making commuting and daily errands a breeze. This home is also close to Winter Haven's renowned Chain of Lakes and other local attractions. Don't miss your opportunity to own this beautifully updated home—schedule your private showing today!

105 Allen Avenue, Winter Haven

$150,000

2 Beds ⋅ 1 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

Under contract-accepting backup offers. Investor special in the heart of the Inwood neighborhood — solid block construction, new roof (2024), and a location that puts you minutes from everything Winter Haven has to give. This two-bedroom (possibly could be a 3 bedroom), one-bath home sits on a fenced lot with mature shade trees, and the covered, screened front porch gives the place a real homey feel the moment you pull up. Inside you'll find ceramic tile throughout the bedrooms and living areas, ceiling fans in every room, and a converted single-car garage that works well as an additional bedroom or possibly a den, home office, or storage space. The layout is straightforward and functional — living room, eat-in kitchen, two bedrooms with built-in closets, and a full bath with pedestal sink and tiled shower. There's also a linen closet in the hall. A shed out back adds extra storage. And the size of the backyard allows for endless possibilities. The home currently has window AC units but no central air or heat system — a definite opportunity for a buyer to update to their preference and immediately add equity. Dual septic system on site. Water is public. The property is being sold as-is. Convenient to US-17, shopping, dining, Polk State College, the Chain of Lakes trail system, and downtown Winter Haven. No HOA. Great bones, priced to move.

3319 Avenue U Nw, Winter Haven

$225,000

2 Beds ⋅ 1 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

Welcome to your private backyard paradise! This beautiful home features two bedrooms, one bath, no HOA, a relaxing jacuzzi spa, functional greenhouses for gardening, storage sheds, irrigation system and a rare, gated private alley at the rear of the property which provides convenient access to your backyard. The property is currently an active plant nursery and the sale includes everything to continue that if you choose. Inside you will find an open layout perfect for comfortable living. Enjoy total peace of mind with newer appliances, windows (2026), electrical wiring (2025), HVAC (2025) and also an indoor laundry space. This property is conveniently located five minutes from downtown Winter Haven, near dining and shopping, close to the Chain of Lakes, Legoland and many parks and outdoor activities. If your looking for the Florida lifestyle then come tour this unique property.

1405 28th Street Nw, Winter Haven

$175,000

3 Beds ⋅ 2 Baths ⋅ Garden Grove SubDv. ⋅ 33884 Zip Code

Under contract-accepting backup offers. 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.

132 Longfellow Road, Winter Haven

$324,700

3 Beds ⋅ 2 Baths ⋅ Haven Homes Sub SubDv. ⋅ 33880 Zip Code

NO HOA. NO CDD. IN GROUND POOL. NEW HVAC. NEW ROOF. Welcome to 2230 W Central Ave, where timeless character meets modern updates on an oversized double lot in the heart of Winter Haven. This well-maintained 3-bedroom, 2-bath home offers comfortable living with inviting spaces designed for everyday life and entertaining. Step inside to a welcoming parlor that flows into the dining room, creating a warm and functional layout. The kitchen features a picturesque window overlooking the backyard and includes Samsung stainless steel appliances. Just off the kitchen, the spacious family room provides a cozy retreat with direct access to the LARGE screened porch. The backyard is the true centerpiece of this property. Enjoy Florida living year-round with a large screened enclosure surrounding the sparkling in-ground pool, offering plenty of space for outdoor dining, relaxing, and entertaining family and friends. Recent improvements provide added value and peace of mind, including a NEW ROOF installed in November 2024, a NEW HVAC Carrier system installed in 2022, and an A.O. Smith water heater. Outdoor enthusiasts will appreciate the public boat ramp to Lake Howard just two blocks away, along with ample driveway parking for your boat, trailer, or additional vehicles. With its spacious lot, major updates, fantastic outdoor living space, and convenient location close to shopping, dining, parks, and the Chain of Lakes, this move-in-ready home is a wonderful opportunity. Come see this gem today!

2230 W Central Avenue, Winter Haven

$329,900

4 Beds ⋅ 2 Baths ⋅ Haven Terrace SubDv. ⋅ 33880 Zip Code

INVESTOR OPPORTUNITY, HOUSE HACK DREAM, OR MULTI-GENERATIONAL LIVING! Welcome to 113 Avenue C SE, Winter Haven, FL, a beautifully maintained and FULLY FURNISHED income-producing property offering exceptional flexibility and value! Situated on a single parcel, this unique property features a charming 3 BEDROOM, 1 BATH main home currently operating as a successful AIRBNB, along with a DETACHED 1 BEDROOM, 1 BATH IN-LAW SUITE with its own private entrance, separate address (258 1st St S, Winter Haven, FL 33880), and alley access, currently rented for $1,100 /MONTH. Both units have been UPDATED, with ROOFS AND A/C SYSTEMS REPLACED WITHIN THE LAST 3 YEARS, allowing peace of mind for years to come. The front home showcases beautiful ORIGINAL HARDWOOD FLOORS, while the rear apartment features attractive WOOD-LOOK TILE flooring. Built in 1950, this property has been exceptionally cared for and is in GREAT CONDITION while maintaining its timeless character. Whether you're looking to HOUSE HACK, generate immediate RENTAL INCOME, accommodate extended family, or expand your investment portfolio, this property checks every box. Located just a SHORT WALK TO DOWNTOWN WINTER HAVEN, you'll enjoy local restaurants, breweries, coffee shops, farmers markets, and year-round community events. Winter Haven continues to experience tremendous growth with ongoing DOWNTOWN REDEVELOPMENT, major investments in public amenities and infrastructure, expanding logistics and employment opportunities through the Central Florida Integrated Logistics Park, and continued economic development expected over the coming years. Conveniently located approximately 10 minutes from LEGOLAND Florida Resort, 45-60 minutes to Walt Disney World, 50-60 minutes to Orlando International Airport, and about 1 hour to Tampa International Airport, this location offers easy access to Central Florida's world-famous attractions while benefiting from Winter Haven's rapidly expanding job market, vibrant downtown, and outstanding quality of life. Whether you're an investor seeking multiple income streams or a homeowner looking for a property that helps pay for itself, this is a RARE opportunity you won't want to miss!

113 Avenue C Se, Winter Haven

$319,900

4 Beds ⋅ 2 Baths ⋅ Fanning Sub SubDv. ⋅ 33880 Zip Code

Welcome to an exceptional HOUSE HACKING and INVESTMENT OPPORTUNITY in the heart of Winter Haven! Legally classified as a SINGLE-FAMILY HOME, this unique property is GRANDFATHERED FOR MULTI-FAMILY USE and is currently configured as two separate living units, making it ideal for INVESTORS, OWNER-OCCUPANTS, or MULTI-GENERATIONAL LIVING. The front unit features 3 BEDROOMS, 1 BATHROOM, its own PRIVATE CARPORT, LAUNDRY ROOM, separate entrance, and private backyard, while the rear unit offers 1 BEDROOM, 1 BATHROOM, a private entrance, private backyard, and is currently rented for OVER $1,200 /MONTH. For added comfort, energy efficiency, and long-term value, the rear unit has been upgraded with a NEW MINI-SPLIT A/C SYSTEM, providing efficient climate control for tenants. The front unit has an estimated rental value of $1,650-$1,750 /MONTH, creating a projected combined rental income of approximately $2,850-$3,000+ /MONTH. Looking for additional upside? One of the bedrooms in the front unit has its OWN EXTERIOR ENTRANCE leading to the patio and offers exciting VALUE-ADD POTENTIAL for a future studio or efficiency conversion by adding a bathroom and kitchenette (buyer to verify all permitting, zoning, and city requirements). Recent 2023 UPDATES include updated kitchen countertops, fresh exterior paint, new flooring and interior paint in the rear unit, along with the installation of the NEW MINI-SPLIT A/C, making this property truly move-in and rent-ready. The home is serviced by ONE WATER METER and TWO SEPARATE ELECTRICAL METERS, allowing each unit to maintain its own electrical service. Perfectly situated just minutes from DOWNTOWN WINTER HAVEN, the famous Chain of Lakes, shopping, dining, healthcare, and schools, you'll also enjoy convenient access to US-27, I-4, Orlando International Airport, Downtown Orlando, and Walt Disney World, along with many of Central Florida's top attractions. As Winter Haven continues to experience significant residential, commercial, and economic growth, this property presents an outstanding opportunity to capitalize on both IMMEDIATE CASH FLOW and LONG-TERM APPRECIATION, whether you're looking to LIVE IN ONE UNIT WHILE RENTING THE OTHER, expand your investment portfolio, or own a versatile income-producing property with exceptional future potential. For added flexibility, the front 3-bedroom unit is also being offered FOR RENT, creating additional options for investors or future owner-occupants. Front Unit was Virtually Staged.

501 Avenue G Se, Winter Haven

$230,000

3 Beds ⋅ 1 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

Virtually Staged. 3129 Avenue W NW is a residence with a functional layout and modern finishes throughout. Clean interior finishes and updated flooring carry through the home, creating a well-maintained aesthetic throughout. This residence combines practical design with comfortable living spaces, delivering functional amenities throughout every room.. Included 100-Day Home Warranty with buyer activation

3129 Avenue W Nw, Winter Haven

$279,900

3 Beds ⋅ 2 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code

This home is located in a established neighborhood, Seller has done lots of updates, New windows,roof ,c/h/a, both bathrooms remodeled all done in 2023 and 2024 and new drainfield aproximately a year ago. Home still has a few things that need updating, but main remodels have been done. Come enjoy the inground pool. Home is surrounded by wood femce in the rear with chain link fence behind the wood fence. Sitting on a huge half acre lot.This home is priced to sell quickly!

105 Lake Sears Drive, Winter Haven

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