Winter Haven / Cypress Gardens Real Estate

Winter Haven / Cypress Gardens Real Estate

Welcome to Winter Haven, Florida, a vibrant city nestled in the heart of Polk County, renowned for its stunning lakes and lush landscapes. Often referred to as the "Chain of Lakes," this picturesque area boasts over 50 sparkling lakes, making it a paradise for water enthusiasts and nature lovers alike. With its warm climate and abundant sunshine, Winter Haven is the perfect place to enjoy outdoor activities year-round.

One of the crown jewels of Winter Haven is the historic Cypress Gardens, which has evolved into a beloved destination for families and thrill-seekers. Originally famous for its enchanting botanical gardens and water ski shows, Cypress Gardens has transformed into a hub of excitement, blending its rich history with modern attractions. Visitors can explore beautiful gardens, take thrilling rides, or simply relax by the water’s edge, soaking in the serene beauty that surrounds them.

Winter Haven is also home to a thriving community with a rich cultural scene. The city hosts various festivals, art exhibits, and live performances throughout the year, ensuring there's always something happening. The downtown area is bustling with charming shops, delightful eateries, and cozy cafes, perfect for a leisurely day out or a night on the town.

For those seeking a place to call home, Winter Haven offers a range of real estate options, from quaint single-family homes to luxurious waterfront properties. With its friendly atmosphere, excellent schools, and convenient access to nearby attractions like Legoland Florida, Winter Haven is an ideal location for families, retirees, and everyone in between. Discover the charm of Winter Haven, where vibrant community life meets the beauty of nature!

Newest Listings in Winter Haven / Cypress Gardens

668 Reggie Road, Winter Haven
$285,000
3 Beds ⋅ 2 Baths ⋅ O6450053 MLS
Virtually Staged. WELCOME TO PEACE CREEK RESERVE! Discover modern Florida living in this beautifully designed 2024-built, single-story home offering 3 bedrooms, 2 bathrooms, approximately 1,444 square feet of living space, and a 2-car garage. The inviting open-concept floor plan seamlessly connects the kitchen, dining, and living areas, creating a comfortable setting for everyday living and entertaining. The contemporary kitchen features attractive cabinetry, solid-surface countertops, a center island, and an open view of the main living area. The spacious primary suite offers a private bathroom with dual sinks and a walk-in closet, while two additional bedrooms provide flexibility for guests or a home office. Enjoy the benefits of newer construction and community amenities including a resort-style swimming pool, playground, and recreational spaces. CONVENIENTLY LOCATED near everyday essentials, including Publix, ALDI, Walmart Supercenter, shopping centers, restaurants, and retail destinations along Cypress Gardens Boulevard and US Highway 27. Outdoor enthusiasts will appreciate Winter Haven's renowned Chain of Lakes, scenic parks, boating opportunities, and nearby LEGOLAND Florida Resort. With convenient access to Winter Haven, Lake Wales, Lakeland, and surrounding Central Florida communities, this property offers an appealing combination of modern comfort, recreation, and everyday convenience. Whether you're looking for a primary residence, seasonal getaway, or investment property, this home is worth exploring. SCHEDULE YOUR PRIVATE SHOWING TODAY!

668 Reggie Road, Winter Haven
1217 Michelangelo Lane, Winter Haven
$399,999
4 Beds ⋅ 4 Baths ⋅ TB8555615 MLS
NO CDD • LOW HOA • SPACIOUS CORNER LOT! Space, style, and modern Florida living come together in this impressive Winter Haven home offering nearly 3,000 SQ. FT. with 4 BEDROOMS + a dedicated OFFICE/BONUS ROOM, 3.5 BATHROOMS + a HUGE UPSTAIRS LOFT. The PRIMARY SUITE and dedicated OFFICE are both conveniently located on the first floor, creating a highly functional layout with privacy, flexibility, and plenty of room to spread out. LOCATION IS ANOTHER MAJOR ADVANTAGE! Enjoy convenient access to LEGOLAND Florida Resort, shopping, dining, entertainment, beautiful lakes, outdoor recreation, and major roadways connecting you throughout Central Florida—all while enjoying the benefits of NO CDD and LOW HOA fees.Some rooms are Virtually Staged Step inside and you’ll immediately appreciate the OPEN-CONCEPT LAYOUT and sense of space. Beautiful CERAMIC TILE flows throughout the first floor, creating a seamless transition between the kitchen, dining, and living areas. The kitchen features GRANITE COUNTERTOPS, plenty of cabinetry and storage, and an open design perfect for everyday living and entertaining. The PRIMARY SUITE on the first floor provides privacy and convenience, while the separate OFFICE/BONUS ROOM, also downstairs, is ideal for working from home, a study, hobby room, playroom, or additional flex space. Head upstairs and the space continues! A HUGE LOFT creates an entirely separate living area—perfect for a MEDIA ROOM, GAME ROOM, HOME GYM, KIDS’ LOUNGE, or SECOND FAMILY ROOM. The remaining three bedrooms are upstairs, offering great separation from the primary suite, along with generous walk-in closets and plenty of storage throughout the home. Outside, the LARGE CORNER LOT gives you even more room to enjoy. The FULLY FENCED BACKYARD and COVERED LANAI create the perfect setting for entertaining, weekend BBQs, pets, or simply relaxing and enjoying the Florida lifestyle. The home also features a FULL GUTTER SYSTEM for added convenience. If you’ve been looking for SIZE, MODERN STYLE, and FLEXIBLE LIVING SPACE, this home delivers—4 BEDROOMS + OFFICE/BONUS ROOM + HUGE LOFT, nearly 3,000 sq. ft., a first-floor primary suite, spacious fenced corner lot, NO CDD and LOW HOA. Schedule your private showing today and experience everything this beautiful Winter Haven home has to offer!

1217 Michelangelo Lane, Winter Haven
5365 San Pietro Drive, Winter Haven
$319,999
4 Beds ⋅ 3 Baths ⋅ TB8558024 MLS
Under Construction. Turquesa BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. The Turquesa is the ultimate family haven, a two-story home featuring 4 bedrooms, 2.5 bathrooms and a private 2-car garage. This home offers an open concept living space designed for both relaxation and entertainment. The half bathroom off the foyer ensures every guest feels at home while the extended foyer opens to the main living and dining area. Featuring luxury vinyl plank flooring and convenient indoor-outdoor living with a lanai through sliding glass doors, it’s a haven of comfort and style perfect for gatherings. The kitchen includes stunning quartz countertops and sleek stainless-steel appliances. Enjoy the spacious upstairs recreation room and the convenience of a laundry room just steps away from the bedrooms. The owner's suite is a secluded retreat with oversized his-and-her walk-in closets, dual vanity and a walk-in shower. Completing this expansive home is the smart thermostat with voice control and professionally designed landscaping, this is truly the epitome of family-friendly luxury! Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails.  Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

5365 San Pietro Drive, Winter Haven
1767 Vanilla Street, Winter Haven
$333,090
4 Beds ⋅ 3 Baths ⋅ TB8558012 MLS
Under Construction. Turquesa BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. The Turquesa is the ultimate family haven, a two-story home featuring 4 bedrooms, 2.5 bathrooms and a private 2-car garage. This home offers an open concept living space designed for both relaxation and entertainment. The half bathroom off the foyer ensures every guest feels at home while the extended foyer opens to the main living and dining area. Featuring luxury vinyl plank flooring and convenient indoor-outdoor living with a lanai through sliding glass doors, it’s a haven of comfort and style perfect for gatherings. The kitchen includes stunning quartz countertops and sleek stainless-steel appliances. Enjoy the spacious upstairs recreation room and the convenience of a laundry room just steps away from the bedrooms. The owner's suite is a secluded retreat with oversized his-and-her walk-in closets, dual vanity and a walk-in shower. Completing this expansive home is the smart thermostat with voice control and professionally designed landscaping, this is truly the epitome of family-friendly luxury! Scenic Terrace pairs comfortable living with inviting community spaces in Lake Hamilton. Amenities include a resort-style pool, clubhouse, playground, and dog park for everyday enjoyment. Ideally located between Orlando and Tampa, residents enjoy convenient access to the best of Central Florida.  Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

1767 Vanilla Street, Winter Haven
1764 Vanilla Street, Winter Haven
$410,620
4 Beds ⋅ 3 Baths ⋅ TB8558005 MLS
Under Construction. Esperanza BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Meet the Esperanza, a single-story, multi-generational home designed for modern living with flexibility and comfort. This 4-bedroom, 3-bathroom, 2-car garage home features a separate multi-gen suite with its own bathroom and kitchenette, ideal for extended family or guests. The spacious layout offers distinct areas for gathering and relaxing, including an open-concept living and dining space paired with a thoughtfully designed kitchen featuring quartz countertops, stainless steel appliances, and smart home technology for everyday convenience. With smart design and stylish touches throughout, the Esperanza balances independence and togetherness, providing room to grow—together. Scenic Terrace pairs comfortable living with inviting community spaces in Lake Hamilton. Amenities include a resort-style pool, clubhouse, playground, and dog park for everyday enjoyment. Ideally located between Orlando and Tampa, residents enjoy convenient access to the best of Central Florida.  Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

1764 Vanilla Street, Winter Haven
1759 Vanilla Street, Winter Haven
$364,745
5 Beds ⋅ 3 Baths ⋅ TB8557999 MLS
Under Construction. Indigo BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Scenic Terrace pairs comfortable living with inviting community spaces in Lake Hamilton. Amenities include a resort-style pool, clubhouse, playground, and dog park for everyday enjoyment. Ideally located between Orlando and Tampa, residents enjoy convenient access to the best of Central Florida.  Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

1759 Vanilla Street, Winter Haven
219 Terranova Boulevard, Winter Haven
$428,000
5 Beds ⋅ 3 Baths ⋅ P4939948 MLS
Don't miss your opportunity to own this 5 bedroom 3 bath pool home in the gated community of Terranova in SE Winter Haven. Minutes from Hwy 27, Hwy 60 and the Polk Parkway. This is a Fannie Mae Homepath property.

219 Terranova Boulevard, Winter Haven
6245 Botticella Boulevard, Winter Haven
$294,990
5 Beds ⋅ 3 Baths ⋅ O6449780 MLS
Under Construction. The first floor of the stunning Edison two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

6245 Botticella Boulevard, Winter Haven
2022 Kapree Court, Winter Haven
$515,000
5 Beds ⋅ 3 Baths ⋅ TB8556796 MLS
3D Virtual Tour available. Welcome to your dream pool home! This beautifully 5-bedroom, 3-bathroom residence offers the perfect blend of comfort, style, and versatility. Ideally located outside the gates to LEGOLAND, this home is perfect for families, vacation-home buyers, or investors seeking a prime location. No HOA. Step inside to discover a lovely interior featuring a spacious, functional layout. The home also includes a private in-law suite/law suite with its own separate entrance, providing an ideal space for extended family, guests, or additional flexibility. The 1/1 suite currently operates as an income generating Airbnb. Step outside to your backyard oasis and enjoy your private pool, perfect for relaxing, entertaining, and making lasting memories. With generous living space, 5 bedrooms, 3 full baths, a separate-entry suite, and an unbeatable location, this home truly has it all.

2022 Kapree Court, Winter Haven
420 Hillcrest Drive Se, Winter Haven
$279,900
3 Beds ⋅ 2 Baths ⋅ TB8557565 MLS
*** WELL CARED FOR WITH MANY RECENT UPDATES IN THIS 3 BED 2 BATH 2 CAR GARAGE *** FRESH PAINT INSIDE & OUT, ALL NEW FLOORING & BASEBOARDS, NEW KITCHEN WITH QUARTZ COUNTER TOPS & APPLIANCES. MASTER RETREAT IS SPACIOUS WITH PRIVATE FULL BATH *** COME CHECK THIS OUT TODAY ***

420 Hillcrest Drive Se, Winter Haven
7380 Bent Grass Drive, Winter Haven
$559,900
4 Beds ⋅ 3 Baths ⋅ P4940007 MLS
Welcome to PARADISE! Enjoy a HEATED, SALTWATER POOL, located on almost half an acre (0.42) in the desired gated community of Miller’s Landing! This expansive 4-bedroom, 2.5-bathroom home offers 2,775 sq. ft. of thoughtfully designed living space featuring tile flooring throughout the main living areas and cozy carpet in the bedrooms. The open-concept floor plan includes formal living and dining rooms, a spacious family room, and interior laundry. The fourth bedroom, complete with double doors, is versatile and can easily serve as a home office. The gourmet kitchen features granite countertops, a breakfast bar, a walk-in pantry, and a large breakfast nook overlooking the pool area. The private primary suite boasts a direct patio door exit, two walk-in closets, and an en-suite bathroom equipped with dual vanities, a garden tub, and a separate shower. Upgraded & Modernized for Peace of Mind: Major Capital Enhancements: Brand-new roof (2026), new exterior paint (2026), new gutters, and a brand-new HVAC system. Outdoor Oasis: A sparkling saltwater pool (converted in 2020) paired with a complete 2024 pool renovation and deck resurfacing, overlooking a massive, fully fenced-feel backyard complete with motion-detection floodlights. A convenient cabana half-bath is directly accessible from the pool deck. Everyday Conveniences: New comfort-height toilets throughout, an installed pulley-winch system for easy attic storage access, and a practical utility sink in the laundry room. Advanced Security: A brand-new in-home security system conveying with the property, featuring 6 perimeter cameras with microphones and speakers. Perfectly combining luxury, security, and exceptional space, this home is ready for you to make it yours!

7380 Bent Grass Drive, Winter Haven
86 Lake Daisy Boulevard, Winter Haven
$269,999
2 Beds ⋅ 2 Baths ⋅ O6449313 MLS
NO HOA AND NO CDD! Welcome to 86 Lake Daisy Blvd in Winter Haven. Don’t let the two-bedroom count fool you—this spacious 2-bedroom, 2-bath home offers 1,826 square feet of living space and an oversized garage with plenty of room for parking, storage, or hobbies. Enjoy an updated interior featuring new flooring, fresh interior and exterior paint, new kitchen and bathroom cabinets, remodeled bathrooms, and updated light fixtures. The roof was replaced in 2023, adding to the home’s appeal.The generous living area provides room to relax and entertain, while the screened porch overlooks a fully fenced backyard with mature trees. With spacious interiors, thoughtful updates, and no HOA or CDD fees, this home is a must-see. Schedule your private showing today!

86 Lake Daisy Boulevard, Winter Haven
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