Winter Haven / Florence Villa Homes with Courtyard Exterior Features

Winter Haven / Florence Villa Homes with Courtyard Exterior Features

Welcome to Winter Haven, a picturesque gem nestled in the heart of Polk County, Florida. Known for its stunning chain of lakes and vibrant community spirit, Winter Haven offers a delightful blend of natural beauty and modern conveniences. The city is renowned for its recreational opportunities, including boating, fishing, and the famous Legoland Florida Resort, making it an ideal destination for families and outdoor enthusiasts alike.

In the charming neighborhood of Florence Villa, you'll find a unique collection of homes that perfectly embody the warmth and character of Winter Haven. One standout feature of these residences is their inviting courtyard exteriors. These homes are designed to create a seamless indoor-outdoor living experience, allowing residents to enjoy Florida's sunny weather year-round. Picture yourself sipping coffee in your private courtyard, surrounded by lush landscaping and the gentle sounds of nature—a perfect setting for relaxation or entertaining guests.

The Florence Villa area is characterized by its friendly atmosphere and strong sense of community. With tree-lined streets and a variety of local amenities, residents enjoy easy access to parks, shops, and dining options. Whether you’re looking for a cozy family home or a charming retreat, the properties in Winter Haven, particularly those with courtyard features, offer a unique opportunity to experience the best of Florida living.

Discover the allure of Winter Haven and the enchanting homes of Florence Villa, where your dream lifestyle awaits!

Newest Winter Haven / Florence Villa Homes with Courtyard Exterior Features

$360,000
5 Beds ⋅ 3 Baths ⋅ O6445712 MLS
Welcome to 4230 Roberta Drive in Winter Haven! This spacious single-family home offers 3 bedrooms, 3 bathrooms, and approximately 2,616 sq ft of heated living area, providing plenty of space for comfortable everyday living. The home features a functional layout with the primary bedroom located upstairs, central A/C and heating, and a 2-car attached garage. With generous living spaces and a practical floor plan, this home offers plenty of possibilities to make it your own. Seller is offering up to $10,000 toward buyer’s closing costs, subject to agreed-upon terms. Enjoy the benefit of a remarkably low association fee of only $275 per year. Conveniently located in Winter Haven with access to shopping, dining, services, and everyday conveniences. A great opportunity to make this property your next home. All information is deemed reliable but should be independently verified by buyer and buyer’s agent.

4230 Roberta Drive, Winter Haven
$338,000
4 Beds ⋅ 2 Baths ⋅ S5157377 MLS
A fantastic opportunity for investors or future homeowners! This beautiful corner-lot home features 4 bedrooms and 2 bathrooms, offering comfort, space, and excellent income potential. It boasts a beautiful, spacious kitchen. The open-concept layout seamlessly connects the living and dining areas, creating the ideal space for entertaining guests or enjoying everyday family life. Sliding glass doors open onto a large backyard—perfect for outdoor activities, gatherings, or simply relaxing. Additional features include a two-car garage, a fully equipped laundry room, and a well-designed floor plan that prioritizes functionality and comfort. Located in the desirable Lake Lucerne community, residents enjoy excellent amenities such as a clubhouse, swimming pools, a playground, and walking paths. The home is close to shops, restaurants, and major roads—including easy access to US-27—making for a convenient commute to Winter Haven, Davenport, and Orlando attractions. Don't miss out on this incredible opportunity!

604 Sarner Pass Way, Winter Haven
$150,000
3 Beds ⋅ 3 Baths ⋅ O6433872 MLS ⋅ 58 BLDG.
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
$78,800
2 Beds ⋅ 1 Baths ⋅ L4963441 MLS ⋅ A38 BLDG.
Virtually Staged. Perched on the third floor, Unit A38 at Winter Haven Condominiums offers the perfect combination of privacy, comfort, and peaceful views. As a desirable end unit, you'll enjoy extra windows that fill the home with natural light along with added privacy from neighboring units. Best of all, elevator access means you can enjoy the top-floor location without worrying about the stairs. Inside, the condo has been thoughtfully updated with newer flooring, fresh interior paint, and modern kitchen cabinetry featuring soft-close doors, creating a bright, inviting space that's truly move-in ready. Just outside your front door, the screened breezeway becomes an extension of your living space. Sip your morning coffee as the day begins, relax with a good book in the afternoon, or unwind in the evening while enjoying Florida's warm breeze and peaceful surroundings. Life here is about more than just the condo. Cool off in the community pool, enjoy a friendly game of outdoor shuffleboard, or take advantage of the community clubhouse, a comfortable, air-conditioned gathering space designed for both relaxation and entertainment. Inside, you'll find a pool table, indoor shuffleboard, fitness equipment, television, and a fully equipped kitchen that's perfect for hosting birthdays, holiday gatherings, game nights, or casual get-togethers. Just bring your favorite food, invite your family and friends, and enjoy the space without the hassle of entertaining at home. Covered, assigned parking is conveniently located just steps from the building, making everyday living even easier. Whether you're looking for a year-round residence or a seasonal escape from colder climates, Unit A38 offers low-maintenance living in a welcoming community where comfort, convenience, and relaxation come together. Schedule your private showing today and experience everything this charming condo has to enjoy.

1700 6th Street Nw Unit A38, Winter Haven
$220,000
2 Beds ⋅ 1 Baths ⋅ L4963168 MLS
Price Improvement!! Welcome to your private backyard paradise! This beautiful home features two bedrooms, one bath, no HOA, a relaxing jacuzzi spa, functional greenhouses for gardening, storage sheds, irrigation system and a rare, gated private alley at the rear of the property which provides convenient access to your backyard. The property is currently an active plant nursery and the sale includes everything to continue that if you choose. Inside you will find an open layout perfect for comfortable living. Enjoy total peace of mind with newer appliances, windows (2026), electrical wiring (2025), HVAC (2025) and also an indoor laundry space. This property is conveniently located five minutes from downtown Winter Haven, near dining and shopping, close to the Chain of Lakes, Legoland and many parks and outdoor activities. If your looking for the Florida lifestyle then come tour this unique property.

1405 28th Street Nw, Winter Haven
$215,000
3 Beds ⋅ 3 Baths ⋅ TB8524293 MLS
Check out this wonderful opportunity to own a spacious 3-bedroom, 2.5-bath home in the desirable 55+ community of Hartridge Landings! This well-maintained community offers a low HOA fee that includes access to the community pool and a private boat ramp on Lake Hartridge, providing access to Winter Haven's renowned Chain of Lakes. Step inside to an open and versatile floor plan featuring two expansive living areas that have endless possibilities for entertaining, relaxing, or creating a dedicated den, formal living room, or family room. The spacious first-floor primary suite serves as a private retreat, complete with an en-suite bathroom featuring dual sinks and a walk-in shower. The galley-style kitchen is conveniently located just off the dining area and offers the perfect space for a cozy breakfast nook. Also on the first floor are a half bath, a generously sized laundry room with built-in shelving, and a flexible office/bonus room with a built-in desk. Both the kitchen and office provide direct access to the private courtyard, creating a great space for outdoor relaxation or entertaining. Upstairs, you'll find two generously sized guest bedrooms and a full bathroom, providing plenty of space for family and visitors. Conveniently located near shopping, dining, medical facilities, and everyday conveniences, this home offers the perfect combination of comfort, functionality, and low-maintenance living. Schedule your private showing today!

2216 Starboard, Winter Haven
$92,000
2 Beds ⋅ 2 Baths ⋅ L4962922 MLS ⋅ C BLDG.
Easy Florida living starts here in Winter Haven Harbour, a centrally located 55+ condominium community close to shopping, dining, medical facilities, public transportation, and downtown Winter Haven. This 2-bedroom, 1.5-bath end-unit condo offers 840 square feet of functional living space and a smart opportunity for a buyer looking to downsize, simplify, or create a comfortable seasonal Florida retreat. The end-unit placement provides added privacy, while the half bath gives the floor plan extra everyday convenience compared to many smaller or single-bath options. Enjoy the low-maintenance lifestyle Winter Haven Harbour is known for, with community amenities that include a heated pool, clubhouse, shuffleboard, grilling area, fitness/community space, car wash area, elevator access, assigned/covered parking, and storage/laundry conveniences. Whether you are a full-time resident or a snowbird looking for a manageable Florida home base, this condo puts convenience, community, and value in one package. Buyer approval required. Buyer and buyer’s agent to verify association rules, fees, leasing restrictions, measurements, and all community information. **Some photos are AI enhanced**

1700 6th Street Nw Unit C21, Winter Haven
$195,000
4 Beds ⋅ 2 Baths ⋅ O6418683 MLS
Closing costs assistance is available. Welcome to 108 Edgewater Drive, a beautifully refreshed single-story stucco home offering 4 bedrooms, 2 full bathrooms, and 1,450 sq. ft. of comfortable living space. Step inside to find sleek ceramic tile flooring throughout the entire home, paired with high-quality solid wood cabinets, elegant solid surface countertops, and modern ceiling fans.The functional, bright layout features a practical indoor laundry closet and double-pane window blinds for added privacy. Move-in ready appliances include a built-in range and refrigerator.The exterior boasts excellent curb appeal, a deep driveway with a 1-car carport, and a fully fenced chain-link backyard perfect for pets or outdoor entertainment. Nestled on a quiet and paved road. You are just minutes away from downtown Winter Haven, shopping, top-rated schools, and local entertainment. Schedule your private tour today!

108 Edgewater Drive, Winter Haven
$299,900
3 Beds ⋅ 3 Baths ⋅ P4938888 MLS
Great Location! NO HOA! New Roof, New AC, 3 New Bathrooms, New Front Door, New Floors etc. Next to Polk State College, Lake Elbert Walking Path, Boat Launch and only 2 miles from Downtown Winter Haven. Fresh paint inside and out. The West side of the house has its own access if you want to use the 3rd bedroom as a mother-in-law suite or rent it out privately. The house access is through the newly paved back alley with a large carport in a quiet neighborhood. It has a Large backyard and awesome neighbors. This house is a great place for a family or someone looking to enjoy the lake, walking path, quiet neighborhood or outdoors.

6 Golfview Circle Ne, Winter Haven
$314,999
2 Beds ⋅ 3 Baths ⋅ P4938108 MLS ⋅ Haven Place BLDG.
Experience refined living in the heart of Downtown Winter Haven with this architecturally significant residence just moments from the city’s vibrant lakeside lifestyle. Perfectly positioned within walking distance of local restaurants, boutiques, parks, and entertainment, this exceptional residence places you at the center of one of Central Florida’s most charming downtown districts. Residents will also enjoy quick access to LEGOLAND® Florida Resort, the renowned Chain of Lakes, and nearby tennis and recreation facilities. Originally designed by celebrated architect Gene Leedy, a pioneer of the Sarasota School of Architecture, this residence showcases the timeless elegance of Florida modernism. Clean architectural lines, open living spaces, and distinctive exposed concrete elements reflect Leedy’s philosophy of blending structural beauty with functional design. Expansive interiors allow natural light to flow throughout the home, creating a seamless connection between indoor comfort and the surrounding Florida landscape. Inside, the thoughtfully designed floor plan offers 2 spacious bedrooms, 2 full bathrooms, and a convenient half bath, with 1,408 square feet of living space that balances openness with privacy. The residence provides a comfortable setting for professionals, couples, or small families seeking both style and convenience in one of Winter Haven’s most desirable walkable locations. With its architectural pedigree, prime downtown setting, and close proximity to the lakes, recreation, and major attractions, 503 Avenue B NW #503 offers a rare opportunity to enjoy living in the heart of Winter Haven.

503 Avenue B Nw Unit 503, Winter Haven
$285,000
2 Beds ⋅ 3 Baths ⋅ L4956453 MLS
Move in ready and located on the Winter Haven Chain of Lakes! Welcome to the gated community of Casarena on the Lakes. This well-designed and meticulously maintained home is set up just right for indoor and outdoor living. The first floor is an open design with the fireplace separating the living and dining area. Enjoy granite countertops and updated appliances in the spacious kitchen that provides the perfect setting to create all of your favorite culinary delights. The living area is a versatile space with a cove for a hosting or exercise area. The main floor is also equipped with a half bath. Head upstairs to the loft that overlooks the living area and separates the two bedrooms. The primary bedroom leads to an open balcony on one side and an updated bathroom on the other. Both bedrooms are oversized with plenty of closet space. The new metal roof was installed in October 2023, The HVAC system has been well maintained, there is a new water heater and the home is also equipped with a whole home generator that is tested regularly. Enjoy the community pool, tennis or pickleball court and access to Lake Cannon, which is on the Winter Haven Chain of Lakes. Downtown Winter Haven is only 10 minutes away and you have quick access to Hwy 92 and 27. Call today for your private showing.

21 Casarena Court, Winter Haven
$116,000
2 Beds ⋅ 1 Baths ⋅ P4934743 MLS ⋅ Winter Haven Harbour BLDG.
This fully remodeled condo offers comfortable and stylish living with two bedrooms and one bathroom. Enjoy brand-new vinyl flooring throughout, making maintenance a breeze. The kitchen features new appliances and solid surface countertops, while the updated bathroom adds a modern touch. Assigned covered parking is included with the unit. The active 55+ community boasts a newly remodeled, heated pool, clubhouse, shuffleboard courts, and a grilling area perfect for entertaining. A convenient car wash station is also available on-site. Public transportation stops right outside the community, and you're just a short distance to shopping and dining options. Medical facilities and a hospital are just blocks away. Centrally located between Tampa and Orlando, this location is ideal for both convenience and connectivity. OWNER WILL CONSIDER FINANCING. Please note: Buyer approval is required. All units are owner-occupied—rentals are not permitted.

1700 6th Street Nw Unit C26, Winter Haven
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