Winter Haven Homes with Maintenance Amenities

Winter Haven Homes with Maintenance Amenities

Welcome to Winter Haven, Florida – a charming city nestled in the heart of Polk County, where vibrant community life meets breathtaking natural beauty. Known for its stunning chain of lakes, Winter Haven is a haven for outdoor enthusiasts and families alike. With a rich history, this picturesque town offers a blend of small-town charm and modern conveniences, making it an ideal place to call home.

Winter Haven boasts a variety of homes that cater to diverse lifestyles, including those with maintenance amenities designed to simplify your life. Imagine living in a beautifully appointed residence where lawn care, pool maintenance, and even exterior upkeep are taken care of for you. This means more time to enjoy the scenic parks, explore the local shops, or partake in the numerous community events that Winter Haven has to offer.

The city is famed for its attractions, including Legoland Florida Resort, which draws families from all over, and the tranquil beauty of the lakes that provide endless opportunities for fishing, boating, and picnicking. With a strong sense of community and a welcoming atmosphere, Winter Haven is not just a place to live; it’s a place to thrive.

Whether you’re looking for a cozy bungalow or a spacious family home, Winter Haven’s real estate market has something for everyone. With maintenance amenities available, you can enjoy the best of Florida living without the hassle of upkeep. Come discover your dream home in Winter Haven, where life is as vibrant as the sunsets over the lakes!

Newest Winter Haven Homes with Maintenance Amenities

$178,500
2 Beds ⋅ 2 Baths ⋅ Winterset 02 A Condo Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to resort-style living in the heart of Winter Haven! This charming 2-bedroom, 2-bath condo/Townhouse offers the perfect combination of comfort, convenience, and an incredible community lifestyle. Located inside a desirable gated community, residents enjoy an impressive selection of amenities including a sparkling community pool, clubhouse, boat ramp with access to Lake Winterset and the Chain of Lakes, tennis and pickleball courts, and more. The location is hard to beat! Just minutes from LEGOLAND Florida, approximately 5 minutes from US Highway 27, and conveniently close to grocery stores, shopping, dining, and some of Winter Haven's hidden-gem local restaurants. Whether you're looking for a full-time residence, a Florida getaway, or a low-maintenance home in a vibrant community, this property offers an exceptional opportunity. Come experience the relaxed Florida lifestyle, recreational amenities, and convenient location that make this community such a special place to call home. Schedule your private showing today!

2007 Garden Lake Drive Unit 2007, Winter Haven
$150,000
3 Beds ⋅ 3 Baths ⋅ Casa Del Sol Condo Village Ph 02 SubDv. ⋅ 33881 Zip Code
Welcome to this spacious 3-bedroom, 2.5-bath corner condo in the lakefront Casa Del Sol community. This two-story home offers 1,334 square feet, an attached two-car garage, granite countertops, newer appliances, inside laundry, and flexible living and dining areas. Sliding doors open to a private courtyard and screened patio overlooking the pool and putting green. All bedrooms are upstairs, including a primary suite with a walk-in closet and private balcony. Whether you're a first-time buyer, downsizer, or investor, this property delivers an easy, low-maintenance living experience. Community amenities include pools, a clubhouse, a fitness center, and access to Lake Hartridge. Conveniently located near downtown Winter Haven, shopping, dining, and major roadways. Schedule your private showing today!

2500 21st Street Nw Unit 58, Winter Haven
$369,900
3 Beds ⋅ 2 Baths ⋅ Hartridge Hills SubDv. ⋅ 33881 Zip Code
Move-In Ready Custom Home in a Gated Community Near the Airport Ideally located for aviation professionals seeking convenient access to the airport or for families looking for a safe, gated community, this beautifully updated custom home offers the perfect blend of comfort, style, and convenience. Built in 1988, this spacious home features an open floor plan with soaring ceilings, stunning exposed wood beams, solid wood doors, and matching wood baseboards that create warmth and character throughout. The split-bedroom layout provides privacy, while the attached two-car garage adds everyday convenience. The recently remodeled interior showcases numerous upgrades, including luxury vinyl plank flooring, fresh interior paint, and updated lighting throughout. The beautifully renovated kitchen features custom wood cabinetry, granite countertops, and a full suite of matching Whirlpool appliances. Both bathrooms have been tastefully updated with new wood vanities, Delta fixtures, Kohler toilets, and stylish tile finishes. The primary bedroom offers the comfort of new carpeting, and the home features smooth ceilings throughout—no popcorn ceilings. Additional highlights include generous laundry room storage, fresh exterior paint, and numerous major improvements for peace of mind. A new roof was installed in March 2026, along with new double-insulated windows, new irrigation, and professional landscaping. Every major update has been completed—simply move in and enjoy. The HOA fee is just $150 per month and includes lawn mowing and fertilization, making it easy to maintain a beautiful yard year-round.

218 Lake Hartridge Drive Nw, Winter Haven
$198,900
2 Beds ⋅ 2 Baths ⋅ Vienna Square SubDv. ⋅ 33884 Zip Code
Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this 2 bedroom 2 bath Vienna Square Villa with pond and wooded view. Located next door to the clubhouse! The charming kitchen has upgraded ivory cabinets, and quartz counter tops. The oak floors flow from the kitchen, and great room giving a warm quality finish. The roof was replaced in 2022. Sold strictly AS-IS. No renting for the 1st 2 years of ownership in this charming 55+ community. This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a low-maintenance lifestyle with reasonable fees, in a welcoming setting. Vienna Square is a beautifully maintained, amenity-rich community designed for easy living. Monthly fees include exterior paint, roof replacement, irrigation water, basic yard maintenance, and a Spectrum Internet/TV package. Residents enjoy access to a community pool, fitness center, billiards, movie nights, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!

1307 Innsbruck Ct, Winter Haven
$325,000
3 Beds ⋅ 2 Baths ⋅ Villamar Ph 6 SubDv. ⋅ 33884 Zip Code
Stunning VillaMar residence in Winter Haven, built in 2024, showcasing modern construction with a clean, contemporary design throughout. The interior features an inviting layout highlighted by a chef-style kitchen that opens seamlessly to a spacious great room, creating an ideal space for both everyday living and entertaining. This home includes a whole-house water filtration system, a screened front porch for comfortable outdoor relaxation, a fully fenced backyard for privacy, and enhanced landscaping with decorative stone accents and fresh plantings that elevate the exterior appeal. Conveniently located approximately 10 minutes from Legoland Florida and about one hour from Disney World, this property offers both comfort and an exceptional lifestyle location. Thoughtfully designed and move-in ready, it delivers style, quality, and lasting value. Schedule your private tour today! Errors, omissions, changes, withdrawal may occur. *Buyers are advised to independently verify square footage, permits, and property details.

4913 Kaia Avenue, Winter Haven
$165,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Tennis Villas SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to effortless Florida living in the highly sought-after gated Cypress Wood Golf & Country Club! Perfectly positioned on the beautifully maintained 10th hole, this 2-bedroom, 2-bath villa offers over 1,100 square feet of comfortable living with no close rear neighbors—just breathtaking views of lush fairways, mature oak trees, and Florida wildlife. Inside, you’ll find a bright, open floor plan complete with a spacious Florida room, the perfect place to enjoy your morning coffee or unwind while taking in the peaceful golf course scenery. Offered fully furnished with quick occupancy available, this home is truly move-in ready. Beyond the entrance, experience the exceptional lifestyle that makes Cypress Wood one of Central Florida’s most desirable golf communities. Enter through a 24-hour guard gate and enjoy a scenic drive along beautifully landscaped, tree-lined streets surrounded by meticulously maintained grounds and natural beauty. Residents have access to outstanding amenities including an 18-hole championship golf course, clubhouse, restaurant, community pool, tennis courts, pickleball courts, and a vibrant social atmosphere. The HOA provides lawn maintenance and exterior upkeep, allowing you to spend more time enjoying everything this resort-style community has to offer. Conveniently located just minutes from LEGOLAND Florida Resort, shopping, dining, and everyday conveniences, with easy access to Highway 27 and I-4, offering an easy commute to both Orlando and Tampa. Whether you’re searching for a full-time residence, winter retreat, or investment opportunity, this villa offers the perfect blend of comfort, convenience, and carefree Florida living. Schedule your private showing today !

665 Broadmoor Circle, Winter Haven
$309,900
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to 2820 Traditions Blvd S, located in the desirable 55+ gated community of Traditions at Lake Ruby in Winter Haven. This well-maintained Augusta model offers 3 bedrooms, 2 bathrooms, a spacious 2-car garage, and a peaceful pond-front setting. This home is perfect for Florida living! The open and comfortable floor plan provides beautiful pond views from the kitchen, dining area, living room, primary suite, and enclosed patio, allowing you to enjoy the tranquil Florida surroundings throughout the home. The kitchen offers ample cabinetry and workspace, while the spacious living areas create an inviting environment for both everyday living and entertaining. The split bedroom layout provides privacy for owners and guests alike. The enclosed patio is a wonderful space to relax, enjoy your morning coffee, or unwind while taking in the water views. Just outside your door, enjoy all that Traditions at Lake Ruby community provides, including a clubhouse, resort-style amenities, pool, fitness facilities, and recreational opportunities designed for an active adult lifestyle. Conveniently located in Winter Haven with easy access to shopping, dining, medical facilities, golf, and Central Florida attractions. Whether you are looking for a full-time residence or a seasonal retreat, this home offers comfort, convenience, and the opportunity to enjoy the relaxed lifestyle of Traditions at Lake Ruby.

2820 Traditions Boulevard S, Winter Haven
$399,900
4 Beds ⋅ 3 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code
Welcome to this beautifully maintained, energy-efficient 4-bedroom, 3-bath home in the highly desirable Traditions at Ruby Lake, a premier 55+ gated community offering the very best of Florida resort-style living. Situated on an oversized lot, this exceptional home features a desirable split floor plan Jack and Jill bathroom w/ walk-in tub and soaring high ceilings that create a bright, open, and spacious feel throughout. Thoughtfully upgraded for both comfort and efficiency, the home offers a spacious, expanded screened lanai with brick pavers—the perfect outdoor retreat for entertaining or enjoying a quiet evening—enhanced by customizable LED lighting to create the ideal ambiance. Energy-saving features include foam-core insulation in the concrete block walls, new Andersen windows, and a freshly painted exterior. Inside, you'll find hardwood flooring in the primary bedroom and front bedroom, which also makes an ideal home office. The kitchen is beautifully appointed with custom cabinetry, granite countertops, slate stainless steel appliances, and abundant storage. Custom maple shelving in the pantry, laundry room, and both linen closets adds both elegance and functionality. The primary bath also features granite countertops, completing the home's high-quality finishes. Designed for comfortable everyday living and effortless entertaining, this home offers generous living spaces that provide both privacy and flexibility for family and guests. HOA dues provide exceptional value and include weekly lawn and landscape maintenance, Spectrum TV service, and exterior house painting every seven years. Residents also enjoy full access to the community's impressive lakefront clubhouse, featuring a resort-style pool and spa, sauna, showers, a fully equipped fitness center, staffed front desk, library, business center, billiards room, craft room, and a spacious ballroom that hosts meetings, dances, entertainment, guest speakers, clubs, and social events. Outdoor amenities are equally impressive and include tennis, basketball, bocce ball, shuffleboard, pickleball, three community boat docks, a picturesque lakeside gazebo, and a paved walking path along the lake—perfect for morning strolls or evening exercise. If you're looking for a move-in-ready home with exceptional upgrades, low-maintenance living, and an active, resort-style lifestyle, this is the one you won't want to miss!

4132 Martindale Loop, Winter Haven
$449,900
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 2 South SubDv. ⋅ 33884 Zip Code
WELCOME to the lifestyle you've been dreaming of in the premier 55+ community of Lake Ashton! This Stunning Designer residence offers the perfect blend of elegance, comfort, and resort-style living with 3 spacious bedrooms, 2 beautifully appointed baths, plus a private den/office in a desirable split-bedroom floor plan. The heart of the home is the spectacular open-concept kitchen, featuring upgraded all-wood raised-panel cabinetry, gleaming granite countertops, stainless steel appliances, abundant storage, and a large breakfast bar overlooking the expansive living and dining areas. Gorgeous tile flooring flows throughout the main living spaces, while plush carpeting adds warmth and comfort to the bedrooms. Natural light fills every room through an abundance of windows, creating a bright and inviting atmosphere. Step through the sliding glass doors onto the screened veranda, where you can relax with your morning coffee or evening cocktail while enjoying peaceful pond views and Florida's beautiful sunsets. The luxurious owner's suite is a private retreat featuring an incredible spa-inspired bath with dual granite vanities, upgraded wood cabinetry, and a spectacular walk-through fully tiled shower designed for both beauty and convenience. Enjoy the pocket doors throughout the house. This house has so many Designer Upgrades, its difficult to list all of them. Life at Lake Ashton is second to none, offering two private golf courses, three pristine natural lakes, two magnificent clubhouses, indoor and outdoor resort-style swimming pools (including a relaxing hot tub), two state-of-the-art fitness centers, racquetball, basketball, tennis, pickleball, scenic walking trails winding throughout the golf course, and the convenience of a golf cart-friendly community. Enjoy dining at the restaurant overlooking the golf course, meet friends for endless social activities and entertainment, and experience the vibrant, active lifestyle you've always imagined. This home has solar panels that will save on your electric bills for years to come. Don't miss this exceptional opportunity to own one of Lake Ashton's most BEAUTIFUL DESIGNER HOMES. Schedule your private showing today and be the first to call this extraordinary residence HOME!

1061 Sawgrass Drive, Winter Haven
$375,000
4 Beds ⋅ 3 Baths ⋅ Terranova Ph 04 SubDv. ⋅ 33884 Zip Code
Set on a spacious .24-acre homesite in the gated Terranova community, this beautifully designed 4-bedroom, 3-bathroom home offers over 2,400 square feet of comfortable living space with a layout that perfectly balances openness and privacy. Mature fruit trees, a low HOA, and no CDD fees make this an exceptional opportunity in one of Winter Haven’s most desirable neighborhoods. Inside, you'll find an inviting open-concept design filled with natural light, enhanced by tile flooring throughout the main living areas and plush carpet in the bedrooms. The split-bedroom floor plan provides added privacy, making it ideal for families, guests, or multi-generational living. Spacious gathering areas flow seamlessly into a separate dining space featuring custom built-in shelving and a convenient sliding glass door leading to the backyard. The heart of the home is the generously sized kitchen, complete with a breakfast bar, abundant cabinet storage, and plenty of workspace for cooking and entertaining. Just beyond, the screened patio offers the perfect place to enjoy Florida’s year-round sunshine while overlooking the expansive backyard. Retreat to the oversized primary suite, where wide windows bring in beautiful natural light. The suite also features a large walk-in closet and a private ensuite bath with a soaking tub, separate shower, and dual functionality designed for everyday comfort. Additional highlights include a 2-car garage, three full bathrooms, ample storage throughout, and a thoughtfully designed single-story floor plan that maximizes both space and convenience. Located just minutes from LEGOLAND Florida Resort, shopping, dining, major roadways, and Winter Haven’s renowned Chain of Lakes, this home combines the tranquility of a gated community with easy access to everything Central Florida has to offer. Call now and schedule your viewing today because space, functionality, and location come together beautifully in this Terranova gem.

306 Terranova Boulevard, Winter Haven
$310,000
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
Perfectly situated on a premium pond-front homesite in the sought-after 55+ gated community of Traditions at Lake Ruby, this beautifully maintained residence offers the ideal blend of comfort, space, and carefree Florida living. With 3 bedrooms, 2 bathrooms, and 2,109 square feet of thoughtfully designed living space, the open split-bedroom floor plan is perfect for both everyday living and entertaining. From the moment you arrive, the paver driveway, carriage-style lighting, manicured landscaping, and covered entry create impressive curb appeal. Inside, soaring ceilings and solid-surface flooring enhance the bright, open feel of the home. The spacious kitchen overlooks the family room and features 42-inch maple cabinetry with decorative rain-glass accents, Corian countertops, a breakfast bar, closet pantry, and a charming dining nook. Designed for gathering, the expansive family room is framed by triple sliding glass doors that showcase tranquil pond views and seamlessly connect to the oversized Florida room. Whether you're hosting friends or enjoying a quiet morning coffee, this inviting space provides the perfect backdrop, complete with views of the soothing waterfront fountain. The generously sized primary suite is a true retreat, offering its own waterfront sitting area, direct access to the Florida room, dual walk-in closets, and a spacious en-suite bath featuring a comfort-height double vanity, garden tub, seated walk-in shower, linen closet, and private water closet. Two additional bedrooms provide flexibility for guests, hobbies, or a home office, while the interior utility room includes a washer, dryer, and utility sink for added convenience. Additional highlights include a 2021 roof, 2024 HVAC system, 2018 water heater, gutters, security system, and a two-car garage with an additional refrigerator. Life at Traditions at Lake Ruby feels like a year-round vacation. Residents enjoy an impressive collection of resort-style amenities, including a lakefront clubhouse, heated pool and spa, fitness center, ballroom, library, billiards room, craft and meeting rooms, tennis courts, pickleball courts, bocce ball, basketball, shuffleboard, dog park, private dock, boat ramp, and a full calendar of social activities. The HOA provides exceptional value with lawn maintenance, exterior house painting, cable, internet, and full access to community amenities included. Conveniently located near shopping, dining, medical facilities, major highways, and LEGOLAND, this waterfront gem offers the perfect opportunity to enjoy an active, low-maintenance lifestyle in one of Central Florida’s most desirable 55+ communities.

3614 Plymouth Drive, Winter Haven
$149,900
1 Beds ⋅ 1 Baths ⋅ Park Lake 03 02 Amd SubDv. ⋅ 33880 Zip Code
MUST SEE! Discover this beautifully remodeled first-floor condo with NO STAIRS to climb, offering the convenience and comfort of true single-level living. Perfect for year-round residents, seasonal owners, or anyone seeking easy accessibility, this move-in-ready home combines modern updates with an exceptional lifestyle in one of Winter Haven's most desirable lakefront communities. Located just steps from the community clubhouse, pool, fitness room, mailboxes, and parking, you'll enjoy maintenance-free living with outstanding amenities right outside your door. Park Lake residents also enjoy access to a private dock, gazebo, and beautiful waterfront views of Lake Lulu, part of the world-famous Winter Haven Chain of Lakes, providing opportunities for boating, fishing, and enjoying Florida's natural beauty. The nearby Chain of Lakes Complex and baseball fields add to the recreational appeal. Inside, soaring vaulted ceilings in the living room, dining area, and primary bedroom create a bright and spacious atmosphere. The screened lanai offers dual entry points and the perfect place to enjoy your morning coffee or evening breeze. Major renovations completed in December 2022 include stylish kitchen cabinetry, granite countertops, under-counter refrigerator, induction cooktop, and ceramic tile flooring throughout. Additional upgrades include impact-resistant windows, a new A/C system with UV light, Nest security system, and a new washer and dryer. The location is hard to beat, with restaurants, shopping, banking, medical facilities, downtown Winter Haven, and LEGOLAND Florida all just minutes away, making this home ideal for both full-time living and seasonal enjoyment. Whether you're looking for a primary residence, winter retreat, or investment opportunity, this beautifully updated condo offers affordability, convenience, lakefront amenities, and a truly carefree Florida lifestyle. Seller financing and Private Financing Available! Do not wait, it will not last long!

2049 San Marcos Drive Se Unit 127, Winter Haven
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