Winter Haven Homes under $250,000

Winter Haven Homes under $250,000

Welcome to Winter Haven, Florida – a charming city nestled in the heart of Polk County, known for its picturesque lakes and vibrant community spirit. With its lush landscapes and sunny weather, Winter Haven offers an idyllic setting for families, retirees, and young professionals alike. The city is renowned for its beautiful Chain of Lakes, boasting over 50 lakes perfect for boating, fishing, and enjoying the great outdoors. Additionally, Winter Haven is home to the famous LEGOLAND Florida Resort, making it a delightful destination for families seeking adventure and fun.

If you’re in the market for a home that combines affordability with charm, you’ll be pleased to discover that Winter Haven offers a variety of homes priced under $250,000. These properties present an excellent opportunity for first-time homebuyers or those looking to invest in a growing area. From cozy single-family homes to townhouses with modern amenities, there’s something for everyone in this welcoming community.

Living in Winter Haven means you’re never far from essential conveniences, including shopping, dining, and entertainment options. The city’s friendly atmosphere fosters a sense of belonging, while its rich cultural offerings, including local festivals and art events, provide endless opportunities to engage with your neighbors.

With its affordable housing market and vibrant lifestyle, Winter Haven is the perfect place to call home. Explore the possibilities today and find your dream home in this enchanting Florida gem!

Newest Winter Haven Homes under $250,000

7060 Fairview Village Circle, Winter Haven
$134,990
1 Beds ⋅ 1 Baths ⋅ Fairview Village SubDv. ⋅ 33881 Zip Code
Welcome Home to Easy Florida Living! Come discover this beautifully maintained 2023 Skyline Park Model, installed in August 2022 and thoughtfully designed with comfort, convenience, and relaxation in mind. From the moment you arrive, you?ll appreciate the new concrete driveway, newer roof, central air, spacious storage, and inviting outdoor living opportunities. Inside, the home offers an open and comfortable layout with a large pantry, dining island, electric fireplace, walk-in shower, and a bedroom spacious enough for a king-size bed. The home is being offered with many furnishings and features, including a French-door refrigerator, electric range, microwave, washer/dryer combo, water softener, blinds, generator ready and more. The lifestyle is just as appealing! The 99-year perpetual lease is renewable for only $1, while the current $90 monthly association fee includes water, sewer, trash, seasonal lawn maintenance, heated pool access, clubhouse, and a variety of community activities. Enjoy shuffleboard, horseshoes, billiards, ping pong, and a community dock with direct canal access to Lake Henry, complete with a pier bench and fire pit. Whether you?re looking for a seasonal retreat, a comfortable Florida getaway, or a place to enjoy the relaxed community lifestyle, this one is ready for you to come see and fall in love with it! Financing Available!

7060 Fairview Village Circle, Winter Haven
306 Eagle Pond Drive Unit 306, Winter Haven
$211,000
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Beautiful completely updated condo in the highly desirable gated community of Cypresswood Golf and Country Club. It features tile flooring throughout the whole condo, marble kitchen countertops with an extended breakfast island, new water heater, matching marble on both bathroom vanities, upgraded lighting fixtures/ceiling fans, interior laundry with washer and dryer, pond view, and so much more. The master bedroom features an en suite bathroom while both bedrooms have a walk-in-closet. Additional linen storage exists in the main bedroom and hallway, plus an additional outside storage closet with shelves. The Cypresswood community features an 18-hole championship golf course designed by Ron Garl, junior Olympic sized community pool, lighted tennis courts, clubhouse with a restaurant, event space and more. Minutes from Hwy 27 and the I-4 corridor, Winter Haven's chain-of-lakes for the water enthusiast, Legoland Fl Park and Resort, Bok Tower gardens, and a brand new Publix shopping center within 2 miles and much more. Centrally located between Orlando and Tampa. Schedule your private showing today.

306 Eagle Pond Drive Unit 306, Winter Haven
6733 Kensington Drive Ne, Winter Haven
$165,500
2 Beds ⋅ 2 Baths ⋅ Lake N Golf Estates SubDv. ⋅ 33881 Zip Code
Charming 2-Bedroom, 2-Bath Home on a Corner Lot Near Lake Henry! Welcome to this beautifully maintained 2-bedroom, 2-bathroom home, where pride of ownership shines from the moment you arrive! From the unique guitar-themed driveway artwork to the immaculate interior, this inviting home is ready for you to move in and enjoy. A new HVAC system installed in 2026 adds to the home's appeal. Situated on a desirable corner lot, the home is located on a street leading directly to the community boat dock overlooking scenic Lake Henry. Whether you enjoy spending time on the water, participating in community activities, or simply relaxing and socializing with neighbors, this location offers plenty of opportunities to enjoy the Florida lifestyle. Inside, the thoughtfully designed floor plan features a bright kitchen with white cabinetry, white appliances, and a convenient center island with seating—perfect for casual meals or morning coffee. Just off the kitchen, the indoor laundry area offers upper cabinets for added storage and organization. The formal dining room features a built-in china cabinet, providing a lovely setting for entertaining family and friends. Adjacent to the dining area, the family room flows seamlessly into the home's entertaining spaces, with sliding glass doors leading to an oversized lanai that spans nearly the entire width of the home. This generous outdoor living area offers plenty of room to relax, entertain, and enjoy Florida's beautiful weather. Both bedrooms offer convenient access to their own bathrooms, providing added privacy and comfort for residents and overnight guests alike. Residents enjoy an active community lifestyle with a variety of amenities and social events offered throughout the month. Conveniently located near shopping, medical facilities, restaurants, and live entertainment, this home also provides easy access to the recreational opportunities and social activities available within the community. Come discover the charm, comfort, and lifestyle this inviting home has to offer!

6733 Kensington Drive Ne, Winter Haven
125 Whittier Lane, Winter Haven
$225,000
3 Beds ⋅ 2 Baths ⋅ Fla Highlands Co Sub SubDv. ⋅ 33884 Zip Code
Virtually Staged. NO HOA! 3BR/2BA Gem in Established quiet Winter Haven Neighborhood! Welcome home to this solid, beautifully built 3-bedroom, 2-bathroom residence featuring a 2-car garage and a spacious, comfortable layout designed for easy living! This property offers complete freedom and flexibility. Big-ticket updates provide complete peace of mind, including a roof replaced in 2020 and an HVAC system installed in 2019. Inside, enjoy an inviting floor plan with ample living space, ideal for relaxing or entertaining. Step outside to your private backyard—perfect for outdoor gatherings, pets, or creating your own backyard oasis. Conveniently located just minutes from top-rated schools, local shopping centers, medical facilities, dining, and popular area attractions. Whether you are searching for your ideal primary residence, a relaxing Florida vacation getaway, or a high-performing addition to your rental investment portfolio, this versatile home is an absolute must-see!

125 Whittier Lane, Winter Haven
240 Westwood Avenue, Winter Haven
$249,900
3 Beds ⋅ 2 Baths ⋅ Brysons R H Sub SubDv. ⋅ 33880 Zip Code
Completely remodeled, full of charm, and NO HOA! Welcome to this beautifully updated 3-bedroom, 2-bath home in Winter Haven, where modern finishes and comfortable living come together. Step inside to a bright, open floor plan featuring beautiful new-look flooring, fresh neutral tones, and an inviting living space that flows seamlessly into the kitchen and dining area. The beautifully remodeled kitchen offers shaker-style cabinetry, gorgeous countertops, stainless steel appliances, modern fixtures, and a spacious breakfast bar perfect for gathering with family and friends. Both bathrooms have been tastefully updated with stylish vanities, modern finishes, and beautiful tilework. A metal roof adds another appealing feature to this already impressive home. Outside, you'll find a spacious backyard with mature trees and plenty of room for entertaining, gardening, pets, or simply enjoying your own outdoor space. With NO HOA, you have the freedom to make this property your own! Conveniently located near shopping, dining, downtown Winter Haven, parks, and the area's beautiful lakes, with access to major roadways connecting you to Lakeland, I-4, Tampa, and Orlando. Beautifully updated, thoughtfully designed, and ready for you to move right in. Come see everything this Winter Haven home has to offer!

240 Westwood Avenue, Winter Haven
1406 Meadow Drive Ne, Winter Haven
$130,000
3 Beds ⋅ 2 Baths ⋅ Buckeye Heights SubDv. ⋅ 33881 Zip Code
Short Sale. Located in Winter Haven, this property offers plenty of potential and a convenient location. The spacious 0.26-acre lot provides room to enjoy outdoor activities and explore future possibilities. With no HOA, you can enjoy added flexibility without monthly association fees or restrictions. The property features a Florida room, offering additional space to relax or entertain. An HVAC system is available but is currently not working. Whether you're looking for your next home or an investment opportunity, this property is worth a look. Enjoy the convenience of being near local shopping and dining options. Everyday essentials are just a short drive away. The location also provides access to major roadways for convenient travel throughout the area. Winter Haven offers a variety of local amenities and recreational opportunities. With some vision, this property offers an opportunity to make it your own. Don't miss the opportunity to explore the possibilities this Winter Haven property has to offer!

1406 Meadow Drive Ne, Winter Haven
650 9th Street Ne, Winter Haven
$179,900
2 Beds ⋅ 2 Baths ⋅ Jarvis Heights SubDv. ⋅ 33881 Zip Code
Lots of potential in this charming 2-bedroom, 2-bath home featuring a large kitchen with plenty of space for cooking and entertaining. The home has new flooring throughout giving the interior a fresh feel. This home has no HOA. Enjoy the outdoors in the large, fully fenched-in yard, perfect for pets, gardening, entertaining or relaxing with family and friends. Additional highlights include a metal roof installed in 2024 providing durability and peace of mind. This home is a great opportunity for homeowners or investors looking for a great space, convenience and potential.

650 9th Street Ne, Winter Haven
609 Maggie Circle, Winter Haven
$224,900
3 Beds ⋅ 2 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code
Welcome home to this block/stucco home with 3 bedrooms/2 baths. The kitchen has been updated for you with granite counters, new cabinets, and newer stainless appliances. Freshly painted, 6-panel doors, and ceiling fans with remotes can be found throughout the home. Primary and Hall Baths feature granite counters, new mirrors and fixtures. Bonus/Flex Room can be a bedroom, den or game room. The yard is fenced with plenty of room to entertain or keep outdoor toys. Make this home yours before the end of the year. HVAC 2025; Roof 2022; Water Heater 2017. Close to restaurants and shopping.

609 Maggie Circle, Winter Haven
113 Nemo Lane, Winter Haven
$239,900
3 Beds ⋅ 3 Baths ⋅ Harbor At Lake Henry SubDv. ⋅ 33881 Zip Code
Brand-new 3-bedroom, 2.5-bath two-story townhome with garage in Winter Haven, FL. The open-concept main level features a spacious living area, flex space, powder room, and private covered lanai. The professionally designed kitchen includes a breakfast bar, 36-inch soft-close birch cabinets, premium laminate countertops, walk-in pantry, and Samsung stainless steel appliances. Upstairs, the owner’s suite offers a walk-in closet and en-suite bath with dual vanities and a tiled shower, while two additional bedrooms share a dual-vanity hall bath. Features include luxury vinyl plank flooring in main areas and baths, stain-resistant carpet in bedrooms, LED lighting, built-in pest control, and energy-efficient construction with Low-E windows, R-30 insulation, and a programmable thermostat. Move-in ready and easy to maintain.

113 Nemo Lane, Winter Haven
444 Avenue I Se, Winter Haven
$119,000
2 Beds ⋅ 2 Baths ⋅ Pine Crest Heights SubDv. ⋅ 33880 Zip Code
INVESTOR OPPORTUNITY with recent systems updates! The costly systems have been updated at this 2-bedroom, 2-bath home at 444 Avenue I SE in Winter Haven: Roof (2025), HVAC (2023), Water Heater (2023), and Plumbing (2023, all except the kitchen). The electrical wiring in the demoed bathroom was also updated in 2023. With these recent updates, more of your renovation budget can go toward finishes and value-adding improvements. Offering approximately 1,036 square feet of living space on a 75 x 140 lot in an established neighborhood close to downtown. Inside, hardwood floors, a wood-burning fireplace, and separate living and dining areas provide character and a solid starting point for your renovation plans. The spacious yard offers room to enjoy the outdoors, while a detached shed provides additional workshop and storage space. No HOA. Located approximately one mile from downtown Winter Haven, the home offers convenient access to Central Avenue's shopping and dining and the historic Ritz Theatre. Winter Haven Hospital and Polk State College's Winter Haven campus are also nearby. Enjoy the area's lakes and outdoor recreation, including South Lake Howard Nature Park, with additional shopping and dining along Cypress Gardens Boulevard and LEGOLAND Florida Resort within driving distance. The home requires repairs and renovation, and is being sold strictly AS-IS. CASH OR HARD MONEY FINANCING ONLY. An opportunity to bring new life to a property with updated systems, character, outdoor space, and proximity to Winter Haven's amenities. Seller makes no representations or warranties regarding condition, square footage, zoning, permitted uses, or future development potential. Buyer and buyer's agent are responsible for conducting their own due diligence. The roof has a hole and requires repairs.

444 Avenue I Se, Winter Haven
193 E Sweet Circle, Winter Haven
$110,000
2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code
Charming 2 bedroom, 2 bath fully furnished home where comfort meets character. This beautifully appointed residence features custom, hand crafted furniture made by the owner, adding a unique personal touch you won't find in most homes. Enjoy the convenience of a move in ready home in an active park that has many games and activities that allows you to meet and make new friends. This home is located in a welcoming community and comes with one share of Orange Manor Co-Op., giving the owner voting rights within the cooperative. Even better, enjoy the benefit of low monthly HOA fees.

193 E Sweet Circle, Winter Haven
217 Grove Ridge Drive, Winter Haven
$160,000
2 Beds ⋅ 2 Baths ⋅ N/A SubDv. ⋅ 33880 Zip Code
HELLO INVESTOR OR FIRST TIME HOME BUYER DON'T MISS THIS FANTASTIC OPPORTUNITY TO OWN YOUR OWN LAND! THIS WELL-MAINTAINED 2 BEDROOM 2 BATH DOUBLE-WIDE MANUFACTURED HOME SITS ON A SPACIOUS 0.26-ACRE OWNED, FULLY FENCED LOT, OFFERING PRIVACY AND PLENTY OF ROOM TO ENJOY THE OUTDOORS. THE HOME FEATURES A BRIGHT AND SPACIOUS LIVING AREA, A LARGE WALK-IN CLOSET IN THE PRIMARY BEDROOM, A NEW WELL WATER SYSTEM, AND RV PARKING. CONVENIENTLY LOCATED CLOSE TO EVERYTHING, THIS PROPERTY IS IDEAL FOR HOMEOWNERS OR INVESTORS SEEKING CONFORT, SPACE, AND VALUE. AGAIN NO LOT RENT. SCHEDULE YOUR PRIVATE SHOWING TODAY.

217 Grove Ridge Drive, Winter Haven
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