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 that perfectly blends small-town warmth with vibrant community spirit. Known for its picturesque lakes and lush landscapes, Winter Haven offers an idyllic setting for families and individuals alike. With its rich history, friendly neighborhoods, and a plethora of recreational activities, this city is a hidden gem in Central Florida.

One of Winter Haven's most appealing features is its stunning array of two-story homes. These properties not only provide ample space for growing families but also offer a unique architectural charm that enhances the community's aesthetic appeal. Imagine waking up in a beautifully designed two-story home, where the sun floods the spacious living areas, and the upper floors provide breathtaking views of the surrounding landscape.

Many of these homes come equipped with modern amenities, expansive backyards, and open floor plans that encourage family gatherings and entertaining. With multiple bedrooms and bathrooms, two-story homes in Winter Haven are perfect for those seeking comfort and convenience. Whether you prefer a cozy nook for reading or a large patio for summer barbecues, these homes cater to a variety of lifestyles.

Living in Winter Haven means enjoying access to excellent schools, vibrant shopping districts, and a variety of outdoor activities, including boating, fishing, and hiking. With its friendly atmosphere and beautiful surroundings, Winter Haven is not just a place to live; it's a place to thrive. Explore the possibilities of two-story living in this delightful city and discover your dream home today!

Newest Winter Haven Homes with Two Story Property Description

$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. 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 park 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
4 Beds ⋅ 2 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 secondary bedrooms offer comfortable accommodations and closet space, while 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
$89,000
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
$219,990
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. Open flow sets the tone for this elegant new Crestone II two-story townhome. There are 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.

3021 Captain Jax Way, 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
$439,900
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
$325,000
4 Beds ⋅ 3 Baths ⋅ Villamar Ph 3 SubDv. ⋅ 33884 Zip Code
Sellers are Motivated!! Welcome to this beautifully maintained 4-bedroom, 2.5-bath residence in the highly sought-after VillaMar community of Winter Haven. Built with energy-efficient construction and featuring fully paid-off solar panels, this home offers the perfect blend of comfort, style, and long-term savings. Step inside to an inviting open-concept floor plan designed for today’s lifestyle. The spacious living and dining areas flow seamlessly into the gourmet kitchen, featuring ample cabinetry, generous counter space, and an ideal layout for both everyday living and entertaining. The primary suite is conveniently located on the first floor, offering privacy and comfort with an en-suite bathroom and spacious walk-in closet. Upstairs, you’ll find three additional bedrooms, a full bathroom, and a versatile loft that provides the perfect space for a second living area, media room, playroom, or home office. Conveniently located just minutes from US Highway 27, Highway 60, and SR-17, this home offers easy access to Orlando, Lakeland, Tampa, and Central Florida’s major employment centers. Shopping, dining, grocery stores, medical facilities, and everyday conveniences are all nearby. Whether you’re a first-time homebuyer, growing family, seasonal resident, or investor, this move-in-ready home presents an exceptional opportunity in one of Winter Haven’s fastest-growing communities. Schedule your private showing today!

1836 Carnostie Road, Winter Haven
$479,900
4 Beds ⋅ 4 Baths ⋅ Graydon Hills SubDv. ⋅ 33881 Zip Code
Virtually Staged. 800 W Lake Elbert Dr NE is an extraordinary piece of Central Florida history, a stately 4-bedroom, 4-bath single-family estate built in 1935 and architecturally designed and built by Cypress Gardens founder Dick Pope. Set on an oversized, beautifully landscaped corner lot of more than half an acre in the sought-after Graydon Hills area of Winter Haven, this timeless residence blends original 1930s craftsmanship with thoughtful comforts, all announced by an imported Italian fountain at the front entrance and lovely views of Lake Elbert just beyond. Inside, over 3,200 square feet of living space showcases rich hardwood floors, handcrafted wood doors, intricate crown molding, custom built-ins, pocket doors, and preserved vintage tile that honor the home's architectural roots, while oversized windows bathe the interior in natural light and frame picturesque lake views. The formal living room welcomes you with a crafted fireplace, while the spacious formal dining room features classic built-ins and flows to a den through elegant french doors. At the heart of the home, a beautifully appointed kitchen pairs historic charm with modern function, featuring custom wood cabinetry, stone countertops, stainless steel appliances, a copper farmhouse sink, and a natural gas range. An adjoining butler's pantry adds a second staircase, storage, and everyday convenience. A main-level flex room with a full bath and original vintage tile provides space for guests, a home office, or a private retreat. Upstairs, the generous primary suite is a true sanctuary, complete with a wood-burning fireplace, a private sitting room, a walk-in closet, a spa-inspired ensuite bath, and tranquil views of Lake Elbert. Two additional bedrooms, one with its own ensuite, share a beautifully tiled full bath, and a dedicated indoor laundry room makes daily living simple. Additional highlights include a detached oversized 2-car garage, a screened porch overlooking the grounds, mature landscaping, natural gas, city water, and NO HOA. The home is ready for a cosmetic refresh, with fresh flooring and paint the primary opportunities to bring your own vision to this architectural treasure, which also carries the potential to be officially registered as a historic landmark. For qualified buyers, this property also carries an existing assumable mortgage at a low interest rate, a valuable advantage in today's market. Ideally located near the Winter Haven Chain of Lakes and moments from Lake Elbert, this singular estate is just minutes from historic downtown Winter Haven, LEGOLAND Florida, shopping, dining, and major roadways. Homes of this pedigree, scale, and craftsmanship seldom come to market. Come experience the timeless character and enduring quality of 800 W Lake Elbert Dr NE, and make a true piece of Winter Haven history your own.

800 W Lake Elbert Drive Ne, Winter Haven
$305,000
4 Beds ⋅ 3 Baths ⋅ Peace Crk Reserve SubDv. ⋅ 33884 Zip Code
Welcome to 981 Harold Pass, a beautifully designed 4-bedroom, 2.5-bath home offering the perfect blend of style, space, and comfort. The open-concept floor plan features a spacious kitchen with a large center island, abundant cabinetry, a generous pantry, and seamless flow into the dining and living areas. Sliding glass doors lead to a covered lanai, perfect for enjoying Florida living. Upstairs, the private owner's suite features a walk-in closet, dual vanities, and a walk-in shower, along with three additional bedrooms, a versatile loft, and a conveniently located laundry room. Currently tenant-occupied, this property presents an excellent opportunity for investors looking to generate immediate rental income. Conveniently located in Peace Creek Reserve with easy access to shopping, dining, schools, and everything Winter Haven has to give Schedule your private showing today and discover the potential this exceptional property has to bring!

981 Harold Pass, Winter Haven
$385,000
3 Beds ⋅ 3 Baths ⋅ Lake Thomas Woods Sixth Add SubDv. ⋅ 33880 Zip Code
Beautifully maintained 3-bedroom, 2.5-bath home on a spacious 0.30-acre lot in the desirable Lake Thomas Woods community with NO HOA! This inviting two-story home features an open floor plan with soaring 17-foot ceilings in the living room, abundant natural light, and a cozy wood-burning fireplace. The remodeled kitchen is designed for both style and functionality, offering granite countertops, a breakfast bar, limestone backsplash, closet pantry, and an adjoining dinette with a built-in desk and sliding glass doors leading to the patio. A separate formal dining room provides the perfect space for entertaining. The first-floor primary suite offers a private retreat with an ensuite bath featuring dual vanities, a garden tub, a separate multi-head shower, and a spacious walk-in closet. The main level also includes a convenient laundry room and half bath for guests. Upstairs, you'll find a versatile loft overlooking the living room—ideal as a home office, playroom, or media space—along with two additional bedrooms and a full bathroom. Additional highlights include recessed lighting, a security system, an automatic irrigation system, and a roof replaced in 2020. Step outside to your private, fully fenced backyard, perfect for entertaining or relaxing. Enjoy the charming grapevine-covered gazebo, spacious patio, and above-ground pool—creating the ideal setting for outdoor gatherings and everyday enjoyment. This move-in ready home combines comfort, space, and convenience in an established neighborhood close to shopping, dining, schools, and major roadways. Don't miss your opportunity to make this exceptional property your new home!

4519 Ashford Drive, Winter Haven
$316,000
4 Beds ⋅ 3 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Under Construction. Brand new, energy-efficient home available by Aug 2026! First-floor primary suite ensures everyone has their own private space. Upstairs loft that can be used fit your needs. 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.

3972 Giorgio Drive, Winter Haven
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