Winter Haven Homes with Two Story Property Description

Winter Haven Homes with Two Story Property Description

Welcome to Winter Haven, Florida—a charming city nestled in the heart of Polk County, renowned for its picturesque lakes and vibrant community spirit. With its warm climate and lush landscapes, Winter Haven is not just a place to live; it’s a lifestyle. Known as the "Chain of Lakes" city, residents enjoy an array of outdoor activities, from boating and fishing to hiking along scenic trails. The city boasts a rich history and a thriving arts scene, making it a perfect blend of culture and recreation.

For those seeking a home that offers ample space and a touch of elegance, our selection of two-story properties in Winter Haven is sure to impress. These homes are thoughtfully designed to maximize both comfort and functionality, featuring spacious living areas that flow seamlessly from room to room. With multiple bedrooms and bathrooms, families can enjoy the luxury of privacy while still being connected.

Imagine hosting gatherings in your expansive backyard or enjoying quiet evenings on a cozy balcony overlooking the serene landscape. Many of these two-story homes come equipped with modern amenities, including gourmet kitchens, energy-efficient appliances, and open-concept layouts that cater to today’s lifestyle.

Whether you’re a growing family, a professional looking for space, or simply someone who appreciates the charm of a two-story home, Winter Haven offers a welcoming community and beautiful properties that make it easy to call this city home. Explore your future in Winter Haven, where the perfect two-story abode awaits you!

Newest Winter Haven Homes with Two Story Property Description

$295,000
4 Beds ⋅ 3 Baths ⋅ Dundee Station SubDv. ⋅ 33881 Zip Code
Priced to Sell! Just installed brand new flooring in the living room and kitchen on the first floor! Carpet was newly installed in 2025. Two story Single Family Home in beautiful DUNDEE STATION community in Winter Haven. This 4 bedroom/2.5 bathroom home features a great open floor plan. As you enter, you are greeted with a spacious living, dining and kitchen area. The kitchen features stainless steel appliances, granite counter tops, breakfast bar/island and large pantry. Half bath is conveniently located next to the living room. Laminate floor on the 1st floor in the common areas and carpet on the 2nd floor. All bedrooms are on the second floor. Nice size master bedroom comes with large walk-in closet. Master Bath has a garden tub, separate walk-in shower, and dual vanity sinks. No washer and dryer. LOW HOA Fee! Close to historic downtown, schools, LEGOLAND/Cypress Gardens Theme Park and shopping. THE PROPERTY IS GREAT FOR PRIMARY USE or INVESTMENT.

1370 Salisbury Drive, Winter Haven
$819,900
4 Beds ⋅ 3 Baths ⋅ Waterford Oaks SubDv. ⋅ 33884 Zip Code
Welcome to 9469 Waterford Oaks Drive, a beautifully maintained and spacious custom built home offering an exceptional combination of comfort, privacy, upgrades, and Florida living in the highly desirable, gated community of Waterford Oaks! A pavered, circular driveway provides an impressive approach to the home with plenty of space for vehicles and guests. Inside, the home features soaring ceilings, elegant archways, crown molding, custom built-ins, a beautiful fireplace, and generous living spaces throughout. The grand primary suite is a true private retreat, featuring two walk-in closets and an expansive primary bath with dual vanity areas, extensive cabinetry, and a large walk-in shower. A dedicated home office with custom built-in cabinetry and bookshelves provides an ideal work-from-home space. Upstairs offers even more flexibility with a large second living room/loft, spacious bedroom, and full bathroom—perfect for guests, family, or a private secondary living area. Outside, enjoy a private screened pool and hot tub/spa with a new spa heater, surrounded by an expansive pool deck with plenty of room for multiple outdoor seating and dining areas. The covered lanai features a high-end built-in outdoor grilling system with a direct gas connection, creating an exceptional space for entertaining year-round. Recent improvements include a new roof, new exterior paint, new hot tub/spa heater, full app-controlled pool automation system, Tesla charger installed in the garage, and multiple filtered-water systems throughout the home. A community boat ramp and dock on Lake Winterset on the Winter Haven Chain of Lakes is just a short distance away. With its spacious floor plan, grand primary suite, private upstairs living area, home office, fireplace, pool and spa, expansive outdoor entertaining space, and extensive recent upgrades, 9469 Waterford Oaks Drive is move-in ready and designed to enjoy the Florida lifestyle.

9469 Waterford Oaks Drive, Winter Haven
$330,000
4 Beds ⋅ 3 Baths ⋅ Windridge SubDv. ⋅ 33881 Zip Code
Spacious 4BR/2.5BA home with 2,836 SF in desirable Windridge! Enjoy a screened saltwater pool, spacious fenced backyard, flexible living areas, and parking for up to 8 vehicles (2-car garage + oversized driveway). Major updates include a 2023 roof and 2022 A/C. Low HOA, no CDD, and convenient access to shopping, dining, schools, and major roads. Quick closing available and priced to sell. Act fast; schedule your private showing today!

5888 Windridge Drive, Winter Haven
$355,000
4 Beds ⋅ 3 Baths ⋅ Eagle Lndg Ph Ii SubDv. ⋅ 33880 Zip Code
PRICE IMPROVEMENT! SELLER HIGHLY MOTIVATED! BEST VALUE IN EAGLE LANDING! Welcome to this beautiful 2022-built home in the desirable Eagle Landing community of Winter Haven, conveniently located just minutes from LEGOLAND Florida and ideally positioned between Tampa and Orlando. Offering approximately 2,300 square feet of living space, this move-in-ready home features a spacious open-concept floor plan designed for comfortable everyday living and entertaining. The modern kitchen flows seamlessly into the main living areas, creating a bright and inviting space. Enjoy Florida living from the screened-in porch overlooking the private, fully vinyl-fenced backyard. Additional features include durable block construction, architectural shingle roof, modern stucco exterior, and a LOW HOA. Whether you're looking for a primary residence, vacation home, or investment property, this home offers an excellent combination of location, size, condition, and value. Offered at $355,000 with a highly motivated seller. Easy to show—schedule your private showing today!

662 Eagle Landing Boulevard, Winter Haven
$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
$350,000
5 Beds ⋅ 3 Baths ⋅ Peace Crk Reserve SubDv. ⋅ 33884 Zip Code
This is a great opportunity to own your dream home located in SE Winter Haven, FL. One of Central Florida’s growing residential markets, known for its family-friendly lifestyle, beautiful lakes, peaceful atmosphere, and strategic location. The property is about one hour from Tampa and Orlando. The home offers a modern and functional design with an open-concept layout, a bright great room that flows into the dining area, and a contemporary kitchen featuring stainless steel appliances, sleek cabinetry, and generous counter space. The laundry room is conveniently located on the first floor, adding everyday comfort and practicality. Upstairs, the home features a versatile loft ideal for a home office, entertainment area, or additional family space. All bedrooms are on the second floor. The private backyard adds lifestyle value for future occupants, offering the perfect space to enjoy Florida’s outdoor living. The seller is motivated and open to considering strong offers, making this property an excellent opportunity for you.

1187 Tyler Loop, Winter Haven
$425,000
4 Beds ⋅ 3 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
ON THE GOLF COURSE IN THE BEAUTIFUL & GATED COMMUNITY OF CYPRESSWOOD GOLF & COUNTRY CLUB!!! Recently remodeled, open, spacious & ready to move in! Enjoy the Cypresswood Country Club lifestyle, including an active clubhouse, junior Olympic size pool, pickle ball courts, tennis, golf and a great restaurant with bar! When you're not enjoying all of the amenities, take a walk or ride your bike on the quiet, tree-lined streets throughout the community! This is a one-of-a-kind, two-story classic home on an extra-large lot, so plenty of room for a swimming pool!!! No rear neighbors, just Florida nature and golf in your backyard! Great place for socializing, family gathering and just lots of relaxing! You can park a dozen cars in your driveway and room to park your fishing boat or up to 6 cars in your garage! The oversized garages come complete with a "golf cart" garage in the rear of the home. Freshly remodeled by Bill Reed Construction, the updates include a freshly painted & neutral color scheme and luxury vinyl flooring throughout. You'll enjoy the golf-course views in the updated kitchen with granite tops and GE appliances. The open & bright kitchen nook area has sliding glass doors, and the family room is adjacent as well as a spacious dining room with lots of windows to enjoy! There is a separate living room with glass sliding doors to the oversized screened lanai and features a brick wood-burning fireplace creating a cozy area with lots of "flex" space. Room for all with 4 bedrooms and the primary suite boasts a walk-in closet, built-ins, dual sinks and a modern barn door. Three of the bedrooms are on the second floor. Mature landscaping and shade trees make perfect areas for enjoying the outdoor beauty and watching golf. Cypresswood is just minutes to Highway 27, great shopping, medical and the new Publix. Right in the heart of Central Florida with a "Chain of Lakes" for boating, fishing and a great "foodie" scene in the charming downtown district. This property has so much for your family to enjoy!!! Call today to schedule your private tour!

300 Greenfield Road, Winter Haven
$331,000
5 Beds ⋅ 3 Baths ⋅ Lucerne Park Reserves SubDv. ⋅ 33881 Zip Code
***Seller has a 2.6 interest rate and is open to creative financing options ***SPACE, VERSATILITY & A FANTASTIC FLOOR PLAN! This spacious 5-bedroom, 3-bath D.R. Horton "Hayden" offering approximately 2,601 square feet of living space in Winter Haven's Lucerne Park Reserve. Step inside and you'll immediately appreciate a floor plan designed for today's lifestyle. Just off the entry is a spacious flex room, currently utilized as a home office, but equally suited for a formal dining room, playroom, study or additional sitting area. Continue into the heart of the home where the open-concept kitchen, dining and family room create one large gathering space perfect for everyday living and entertaining. The kitchen features dark cabinetry, generous counter space, a large center island with breakfast-bar seating, pantry storage and a complete appliance package. Sliding glass doors provide easy access to the backyard and bring natural light into the main living areas. One of the most desirable features of this floor plan is the first-floor secondary bedroom and full bathroom, providing excellent flexibility for overnight guests, extended household needs or an additional private workspace. Upstairs, the home's generous proportions continue with a large loft, creating another flexible living area for a media room, game room, homework area or second family room. The oversized primary suite provides plenty of room for a complete bedroom set plus an additional sitting area. The primary suite is complemented by a private bath and walk-in closet. Built in 2021, the home also features tile in the main traffic areas, carpeted living and bedroom spaces, abundant storage and solar panels for added energy-conscious appeal. Outside, enjoy a backyard with plenty of possibilities for creating your own Florida outdoor living space. Lucerne Park Reserve offers residents a community pool, playground, sidewalks and recreational areas, all while providing convenient access to shopping, dining, entertainment and major Central Florida roadways, including access toward I-4. If you've been looking for a home with five bedrooms, three full bathrooms, a downstairs guest suite, dedicated flex space AND an upstairs loft, this floor plan delivers the versatility that's hard to find. Schedule your private showing and see just how much space this home has to offer!

706 Peyton Brooke Way, Winter Haven
$79,000
1 Beds ⋅ 1 Baths ⋅ Havencrest Add SubDv. ⋅ 33880 Zip Code
* Investor Alert* Fixer upper located in the heart of Winter Haven. 1 Bed, 1 Bath with tons of potential. This could make for a great rental property or flip.

212 Avenue F Se, Winter Haven
$398,000
3 Beds ⋅ 2 Baths ⋅ 33880 Zip Code
One or more photos have been virtually staged. HALF ACRE LOT WITH NO HOA!!!! Welcome to this well maintained home on a spacious .53 acre lot. . This home offers the Primary Bedroom and full bathroom downstairs with two bedrooms and full bathroom upstairs. Featuring A NEW ROOF, vinyl floor planks throughout the downstairs, NEW carpet in bedrooms, BEAUTIFUL new flooring upstairs AND NEW vanity's in both bathrooms. The kitchen has wood cabinet's with soft close drawers and doors and newer stainless appliances. A versatile bonus room adds flexible space for a playroom, additional family room or an office. With the freedom of an LARGE lot it’s perfect for outdoor living or parking a boat or RV but still close to restaurants and grocery stores. Don’t miss the opportunity to make this yours!

5838 Old Bartow Eagle Lake Road, Winter Haven
$429,900
4 Beds ⋅ 3 Baths ⋅ 33880 Zip Code
This 4-bedroom, 3-bathroom, two-story home is tucked away on a cul-de-sac beneath beautiful mature oaks. Situated on .44 acres with no HOA, the property provides plenty of room and flexibility to make it your own.Step inside to soaring ceilings, exposed wood beams, warm flooring, and a dramatic stone fireplace that gives the home its inviting character. The kitchen features granite countertops, stainless-steel appliances, rich cabinetry, and a breakfast bar that keeps everyone connected. One bedroom and a full bathroom are located downstairs, while three additional bedrooms are upstairs. The primary suite opens to an oversized screened balcony overlooking the tree-shaded backyard—the perfect place to enjoy a quiet morning or relax at the end of the day. Outside, the expansive backyard is ready for gatherings, gardening, recreation, or the outdoor retreat you’ve been imagining. Multiple screened areas create inviting places to enjoy the outdoors, while the attached two-car garage adds everyday convenience. For added peace of mind, the seller will have a NEW ROOF installed before closing. Come experience the space, charm, and possibilities that make this home truly special.

4734 Monterey Drive, Winter Haven
Start Your Search