Winter Haven Homes with Two Story Property Description

Winter Haven Homes with Two Story Property Description

Welcome to Winter Haven, Florida – a picturesque city nestled in the heart of Polk County, renowned for its stunning lakes, vibrant community, and a laid-back lifestyle that perfectly blends natural beauty with modern conveniences. With over 50 lakes, Winter Haven is often referred to as the “Chain of Lakes,” making it a haven for water enthusiasts and outdoor lovers alike. Whether you’re exploring the scenic walking trails, enjoying a day of fishing, or indulging in a leisurely boat ride, the beauty of Winter Haven is sure to captivate you.

For those seeking a home that combines elegance with functionality, our collection of two-story properties in Winter Haven is simply irresistible. These homes offer spacious layouts designed for both comfort and style, making them perfect for families of all sizes. With multiple bedrooms and bathrooms, these residences provide ample space for everyone to enjoy their own sanctuary. The open-concept living areas are ideal for entertaining, while the well-appointed kitchens are a chef’s dream, featuring modern appliances and plenty of counter space.

Step outside, and you’ll find beautifully landscaped yards that invite you to enjoy the Florida sunshine. Many of these two-story homes also come with outdoor patios or decks, perfect for hosting summer barbecues or simply unwinding after a long day.

Living in Winter Haven means being part of a community that values both relaxation and recreation. With excellent schools, shopping, dining, and cultural attractions nearby, it’s easy to see why so many are drawn to this charming city. Discover your dream two-story home in Winter Haven today, and embrace a lifestyle filled with warmth and adventure!

Newest Winter Haven Homes with Two Story Property Description

1400 Lake Elbert Drive Se, Winter Haven
$427,000
5 Beds ⋅ 6 Baths ⋅ Elbert Hills SubDv. ⋅ 33884 Zip Code
Welcome to this spacious 2-story home in Winter Haven, offering 5 bedrooms, 5.5 bathrooms, and a private pool. With room for everyone and a layout that works for multigenerational living, this property is ready for its next owner. Inside, the main-floor primary suite offers convenience and privacy, with a walk-in closet to match. A fireplace anchors the living area, adding warmth and a natural gathering spot. Upstairs, the additional bedrooms give family and guests plenty of space, and walk-in closets and extra storage throughout keep everything organized. A dedicated laundry room makes everyday chores easy. Outside, the private pool is ready for year-round Florida enjoyment, and the garage provides parking and additional storage. Don’t miss your chance to own this spacious Winter Haven home.

1400 Lake Elbert Drive Se, Winter Haven
1783 White Elephant Loop, Winter Haven
$364,900
5 Beds ⋅ 3 Baths ⋅ Peach Crossings SubDv. ⋅ 33884 Zip Code
Virtually Staged. ONLY $1,000 DOWN AT SIGNING! BUILDER PAYS THE REMAINING CLOSING COSTS! PLUS, A PROMOTIONAL 4.99% INTEREST RATE FIXED FOR THE FIRST 5 YEARS WITH A 5/1 ARM FOR QUALIFIED BUYERS! BRAND NEW, MOVE IN READY SINGLE FAMILY HOME WITH 5 BEDROOMS AND 3 FULL BATHROOMS! Why wait months to build when you can move right into a beautifully designed new construction home with incredible builder incentives? Welcome to 1783 White Elephant Loop, featuring the spacious Spring floor plan by LGI Homes in the desirable Peach Crossings community. This impressive home offers five generously sized bedrooms, three full bathrooms, and a thoughtfully designed layout that combines modern comfort, functionality, and plenty of room to grow. Step inside to discover bright, inviting living spaces perfect for everyday living and entertaining. With five spacious bedrooms, you'll have endless possibilities for a home office, guest accommodations, playroom, fitness room, or hobby space. The exceptional owner's suite provides a relaxing private retreat with plenty of room for a king sized bed, additional furnishings, and a cozy reading area. The adjoining bathroom features a beautiful dual sink vanity, convenient linen closet, and an impressive walk in closet offering abundant storage and organization. Three full bathrooms provide added convenience for busy households and visiting guests. Enjoy the benefits of brand new construction, modern finishes, and the peace of mind that comes with owning a newly built home. Peach Crossings offers a welcoming community atmosphere with a children's playground and picnic area, along with convenient access to nearby schools, shopping, dining, and everyday essentials. Whether you're looking for additional bedrooms, flexible living spaces, or a beautiful new home without the construction wait, this property checks all the boxes! With builder paid closing costs, incredible promotional financing, five spacious bedrooms, and immediate move in availability, this is an outstanding opportunity to own brand new construction at an exceptional value. Schedule your private showing today! Promotional financing and closing cost incentives are subject to buyer qualification, participating lender requirements, and program availability. The advertised 4.99% interest rate applies to the initial five year fixed rate period of a 5/1 adjustable rate mortgage, after which the rate may adjust.

1783 White Elephant Loop, Winter Haven
3099 Captain Jax Way, Winter Haven
$205,090
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. This new two-story townhome offers ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3099 Captain Jax Way, Winter Haven
2097 Whispering Trails Boulevard, Winter Haven
$410,000
4 Beds ⋅ 3 Baths ⋅ Whispering Trails Ph 01 SubDv. ⋅ 33884 Zip Code
Discover your ideal Florida retreat in this beautifully maintained, gated Winter Haven neighborhood! Perfectly situated close to shopping centers for effortless errands, just 10 minutes from the exciting attractions of Legoland, and less than an hour from the Walt Disney World. Tampa is also within a convenient 1-hour drive, offering additional entertainment and amenities. This charming home comes move-in ready, including all essential appliances such as a range, refrigerator, microwave, garbage disposal. The secure, gated community offers peace of mind and added privacy, making it an ideal place to call home. Whether you're looking for a primary residence, vacation home, or investment property, this residence offers comfort, convenience, and easy access to some of Florida’s top attractions. Don’t miss your chance to own this fantastic 4 bed 3 full bath pool home in the fast-growing City of Winter Haven!

2097 Whispering Trails Boulevard, Winter Haven
4000 Giorgio Drive, Winter Haven
$325,000
4 Beds ⋅ 3 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Brand new, energy-efficient home available by Dec 2026! First-floor primary suite ensures everyone has their own private space. Second floor offers a spacious loft that can be used to best fit your family's needs. Enjoy preparing meals with your family in the open kitchen with spacious work island. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

4000 Giorgio Drive, Winter Haven
5378 San Pietro Drive, Winter Haven
$396,828
5 Beds ⋅ 3 Baths ⋅ Villa Mar SubDv. ⋅ 33884 Zip Code
Under Construction. Valencia BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender.  Prepare to be impressed by the Valencia, a two-story home featuring 5 bedrooms, 3 bathrooms, and a 2-car garage. This floorplan is designed for modern living and effortless entertainment. Step through the elegant foyer into a vibrant main living area, complete with a private guest suite for ultimate comfort. The kitchen shines with sleek quartz countertops, stainless steel appliances, and luxurious vinyl plank flooring overlooking the dining area which flows beautifully to the covered lanai through sliding glass doors. Upstairs, you’ll find the secluded owner’s suite complete with a walk-in shower, dual vanity and spacious walk-in closet. Conveniently located by the additional bedrooms is the cleverly designed oversized laundry room. Another modern feature of the Valencia is the smart thermostat with voice control, making energy efficient living a breeze. Outside, enjoy the chic elevation and professionally curated landscaping that adds the perfect finishing touch to this exceptional home. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails.  Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

5378 San Pietro Drive, Winter Haven
5357 San Pietro Drive, Winter Haven
$329,990
4 Beds ⋅ 3 Baths ⋅ Villa Mar SubDv. ⋅ 33884 Zip Code
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.

5357 San Pietro Drive, Winter Haven
1550 11th Street Ne Unit C5, Winter Haven
$115,000
2 Beds ⋅ 2 Baths ⋅ Lake Buckeye Condo SubDv. ⋅ 33881 Zip Code
This updated unit has 1,148 sq ft of living space, with new flooring, new countertops and plenty of natural light throughout. The kitchen has a large pantry, and the washer and dryer are in the unit. Step out onto the balcony for direct views over Lake Buckeye. Both bedrooms are a good size with large closets, and the primary bedroom has its own private bathroom. Residents can use the community pool. The unit is currently leased at $1,150 a month, and the lease continues after closing, so the buyer takes over an existing tenancy and income from day one. Showings are by appointment only, with notice to the tenant. Information is deemed reliable but not guaranteed. Buyer to verify square footage, lease terms, HOA fees and rules, and all other details.

1550 11th Street Ne Unit C5, Winter Haven
3403 Julius Estates Boulevard, Winter Haven
$349,000
4 Beds ⋅ 3 Baths ⋅ Lake Smart Estates SubDv. ⋅ 33881 Zip Code
Enjoy comfortable living in this spacious home offering just under 2,400 square feet of living space in a convenient North Winter Haven location. Situated directly across from the community swimming pool, newly replaced AC this home offers easy access to neighborhood amenities, including a fishing pier. The backyard features a peaceful view overlooking a small pond, creating a relaxing setting to enjoy your outdoor space. The thoughtfully designed floor plan features an open and inviting downstairs living area with the living room, kitchen, and family room, while all bedrooms are conveniently located upstairs, providing added privacy. The kitchen is appointed with granite countertops, and the home also features a two-car garage and the added convenience of an upstairs laundry area with washer and dryer included. With quick access to Highway 27, getting around Winter Haven and the surrounding areas is a breeze. Enjoy the combination of spacious living, community amenities, peaceful water views, and a convenient location in this inviting home!

3403 Julius Estates Boulevard, Winter Haven
5780 Lakeside Landings Boulevard, Winter Haven
$290,000
4 Beds ⋅ 3 Baths ⋅ Lakeside Landings Ph 01 SubDv. ⋅ 33881 Zip Code
Enjoy peaceful pond views and spacious living in this 4-bedroom, 2.5-bathroom, two-story home in Winter Haven! Built in 2016, this 2,526-square-foot home offers plenty of room to spread out and enjoy comfortable everyday living. Major updates include a roof replacement in late 2023 and exterior paint completed shortly afterward. The A/C has also been recently serviced for added peace of mind. Located in an established community of Lakeside Landings featuring sidewalks, a neighborhood pool, and a playground, there are plenty of opportunities to enjoy the outdoors. Conveniently situated near Lake Fannie (part of the Chain of Lakes) off Lucern Park Rd, with easy access to Hwy 27, shopping, dining, and other everyday conveniences, this home puts you within reach of all that Winter Haven and Central Florida have to offer. Don't miss the opportunity to make this spacious home your own!

5780 Lakeside Landings Boulevard, Winter Haven
1140 Tyler Loop, Winter Haven
$308,000
3 Beds ⋅ 3 Baths ⋅ Peace Crk Reserve SubDv. ⋅ 33884 Zip Code
Short Sale. Short Sale. Welcome to 1140 Tyler Loop in Winter Haven! This two-story home offers 4 bedrooms, 2.5 bathrooms, and an open floor plan that connects the living, dining, and kitchen areas—ideal for everyday living and entertaining. The kitchen offers ample cabinet space, while the primary suite features a private bathroom and generous closet space. Additional bedrooms provide flexibility for guests, a home office, or hobbies. An attached two-car garage adds convenient parking and storage. Discover the possibilities and schedule your private showing today! Sale is subject to lender approval of the purchase price and terms. Additional time may be required for the short sale approval process.

1140 Tyler Loop, Winter Haven
1606 Eagle Pond Drive, Winter Haven
$155,000
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Step into an inviting opportunity and a genuine deal at this price in the desirable Cypresswood Golf & Country Club. Whether you’re seeking a comfortable full-time residence, a relaxing winter retreat, or a place to embrace an active Florida lifestyle, this second-floor 2-bedroom/2-bathroom condo delivers warmth, convenience, and a true sense of community.Enjoy the privacy of an upper-level location with a practical, easy-flow layout designed for comfortable living, plus a convenient storage room for extra belongings. Maintenance-free ownership means the HOA handles exterior and ground maintenance, community pool access, 24-hour security, common-area upkeep, trash service, exterior pest control, and private road maintenance—so you can simply enjoy your home.The convenient location, a short drive to Legoland Florida Resorts, and offers easy access to Hwy 27, making shopping, dining, medical facilities, and everyday errands quick and simple while still keeping you nestled in a peaceful community setting. Residents are welcomed into a lifestyle filled with amenities: a championship 18-hole golf course, on-site restaurant & clubhouse for dining & events, sparkling community swimming pool, tennis courts & pickleball courts, and fitness center. Perfectly positioned for those who value both relaxed living and an active community atmosphere, this condo offers exceptional value and an immediate sense of belonging in one of Winter Haven’s most appealing settings. Schedule your private showing today and experience the lifestyle for yourself. All buyers must provided a pre-approval letter or proof of funds. Buyers are responsible for verifying the accuracy of all information.

1606 Eagle Pond Drive, Winter Haven
Start Your Search

How much is your home worth?

Get instant property value now!