Winter Haven Homes with Courtyard Exterior Features

Winter Haven Homes with Courtyard Exterior Features

Welcome to Winter Haven, Florida – a charming gem nestled in Polk County, known for its stunning lakes, vibrant community, and rich history. Often referred to as the "Chain of Lakes City," Winter Haven boasts over 50 sparkling lakes, making it a paradise for water enthusiasts and nature lovers alike. The city offers a delightful blend of small-town charm and modern conveniences, with an array of shopping, dining, and recreational activities that cater to every lifestyle.

One of the most sought-after features in Winter Haven's real estate market is the homes with courtyard exterior features. These properties not only exude a unique architectural appeal but also provide a serene outdoor space that enhances the living experience. Imagine stepping into your private courtyard, surrounded by lush greenery and blooming flowers, where you can enjoy morning coffee, host gatherings, or simply unwind after a long day.

Homes with courtyard designs often feature open floor plans that seamlessly integrate indoor and outdoor living, allowing for natural light to flood the interiors while maintaining a sense of privacy. This architectural style is perfect for those who appreciate both aesthetics and functionality. Whether you're looking for a cozy retreat or a spacious family home, Winter Haven's courtyard homes offer a perfect blend of comfort and elegance.

With its friendly atmosphere, excellent schools, and abundant recreational opportunities, Winter Haven is not just a place to live; it's a place to thrive. Discover your dream home today and experience all that this picturesque city has to offer!

Newest Winter Haven Homes with Courtyard Exterior Features

100 Island Way, Winter Haven
$1,100,000
4 Beds ⋅ 6 Baths ⋅ O6452572 MLS
Discover timeless elegance and waterfront living at 100 Island Way, a distinctive custom estate nestled within the gated community of Orchid Springs. Situated on approximately 1.29 acres of beautifully landscaped grounds overlooking Lake Lewis, this remarkable residence offers 4,179 square feet of living space, 4 bedrooms, 4 full bathrooms, 2 half bathrooms, and a detached artist's studio. Originally built in 1969, this one-of-a-kind home showcases exceptional architectural character, featuring natural coral rock sourced from Coral Gables, rich wood accents, custom built-ins, and thoughtfully designed living spaces. A grand circular driveway and expansive porte-cochère create an impressive entrance, welcoming you into a home filled with warmth, charm, and picturesque garden and lake views. At the heart of the residence is a stunning chef's kitchen, beautifully transformed in 2021 with an approximately $200,000 renovation. Featuring custom solid wood cabinetry, premium quartz countertops, a Wolf gas range, oversized Sub-Zero refrigerator, matching wine refrigerator, and a dedicated coffee and wine bar, this exceptional space is designed for both everyday living and entertaining. Two spacious primary suites, a private home office, and a library area provide comfort and versatility, while distinctive architectural details, including exotic redwood floating vanities, natural wood veneer accents, and custom sliding doors, add character throughout. The detached artist's studio offers additional flexible space, ideal for creative pursuits, a private workspace, or a personal retreat. An unexpected second-floor reading or drafting room, accessible by a spiral staircase, adds to the property's unique charm. Step outside into your own private Florida oasis, where lush tropical gardens, brick-lined courtyards, and expansive verandas create inviting spaces for relaxation and entertaining. Enjoy breathtaking waterfront views and a private dock on Lake Lewis, perfect for fishing, canoeing, or simply unwinding while watching the sunset. Notable improvements include the 2021 kitchen renovation, wood-look ceramic tile flooring installed in 2020, several remodeled bathrooms, four A/C units replaced in 2018, plumbing updates, refreshed exterior paint, and updated dock decking. Blending timeless craftsmanship, modern comforts, and serene waterfront surroundings, 100 Island Way presents a rare opportunity to own a truly distinctive Florida estate. Experience the beauty, privacy, and character of this exceptional property. Schedule your private showing today!

100 Island Way, Winter Haven
2212 Starboard Unit 2212, Winter Haven
$229,900
2 Beds ⋅ 2 Baths ⋅ P4940270 MLS ⋅ Na BLDG.
Enjoy Florida Living in this updated 2BR/2BA home located in the lakefront 55+ community on Lake Hartridge. Only 42 units in Hartridge Harbors condo situated on the beautiful Winter Haven Chain-of-Lakes. Well maintained complex with affordable HOA fees. This home features a 2 car garage, inside laundry, new appliances, Large master suite, and large guest room. Screened and private patio at the rear of the house affords space for outdoor kitchen, spa, or garden area. Location is ideal-close to shopping, restaurants, medical, etc. Community amenities include a clubhouse and pool while offering low maintenance living. Call today for your private showing.

2212 Starboard Unit 2212, Winter Haven
100 El Camino Drive Unit 208, Winter Haven
$139,900
1 Beds ⋅ 1 Baths ⋅ O6451540 MLS ⋅ 100 BLDG.
OWNER MOTIVATED Beautiful Condo, Tastefully remodeled, completely updated in 2023. All new appliances, granite counter tops, remote controlled fans, Kitchen and bathroom new cabinets. Come enjoy Florida Living or just retire in style or enjoy it as your Winter Getaway. A small Bonus space may be used as a second sleeping quarters for additional guests. Conveniently located near shopping centers, restaurants, hospitals, churches and more. HOA fees cover your cable, internet, water, sewer, trash pick up and natural gas. Exclusive Carport. Seller will assist you with closing costs or interest rate buy down if needed.

100 El Camino Drive Unit 208, Winter Haven
829 Sun Ridge Village Drive, Winter Haven
$369,900
4 Beds ⋅ 3 Baths ⋅ O6447971 MLS
Move-in ready four-bedroom, 2.5-bathroom home located in the desirable Sun Ridge Village Ph 01 neighborhood. This home features an open floor plan that flows seamlessly throughout the main living spaces. The updated kitchen is equipped with sleek granite countertops and stainless steel appliances, making it a functional and modern space for cooking and gathering. The primary suite offers a private retreat, complete with a primary bathroom and a large walk-in closet. Outside, enjoy a fully fenced backyard perfect for privacy and outdoor enjoyment. Conveniently located minutes from the toll road with easy access to Tampa and Orlando. Schedule your private showing today!

829 Sun Ridge Village Drive, Winter Haven
1921 Manor Circle Se, Winter Haven
$1,295,000
3 Beds ⋅ 3 Baths ⋅ L4965515 MLS
Imagine waking each day to breath-taking lake views, swaying palms, spectacular sunsets, and the tranquil beauty of Lake Lulu. Quietly positioned on one of the most desirable lakes within Winter Haven's renowned Chain of Lakes, this beautifully maintained and thoughtfully updated single-story residence enjoys a private setting on 0.45-acre lot, surrounded by mature landscaping and established tropical gardens. Designed for both comfortable everyday living and exceptional entertaining, the home offers spacious, versatile accommodation with stunning lake views from the moment you enter through the front door. The flowing floor plan seamlessly connects the formal living and dining areas, with 50-inch SAMSUNG TV & rich wood flooring to the family room, kitchen, breakfast nook, and outdoor living spaces, creating an inviting atmosphere throughout. At the heart of the home is a well-appointed gourmet kitchen featuring a large center island, breakfast bar, premium stainless-steel appliances, updated Kitchen-aid double ovens with air fryer, microwave, French-door refrigerator, and dishwasher. Custom cabinetry includes soft-close drawers, pull-out shelving, glass display cabinets, wine storage, pantry space, and appliance garage. Beautiful non-slip tile flooring extends throughout the main living areas. Adjacent to the kitchen, the breakfast nook offers direct access to the pool area through sliding glass doors, while the spacious family room features a stunning Travertine fireplace, built-in SAMSUNG 50-inch television, neutral finishes, and expansive 12-foot sliding glass doors that open directly to the screened resort-style swimming pool & paved Lanai (1485sq,ft ) The laundry room is equipped with custom cabinetry, generous storage, a large linen closet, and includes a front load washer and dryer. A conveniently located half bath provides direct access to the pool and outdoor entertainment area. The fourth bedroom is currently configured as a home office. NEW (AUGUST 2026) ARCHITECTURAL SHINGLE ROOF on home, boathouse and storage shed. Owned security system. Phone, internet, and Wi-Fi connectivity throughout the home. Extensive custom cabinetry and storage solutions. Walk-in closet system in the primary suite. Landscaped with irrigation and lighting. Circular paved driveway with courtyard entrance and carriage lighting. Attached 2 car garage has staircase to large, walk-up attic for extra storage. 106ft frontage on Lake Lulu with a private dock, boathouse with lift. Direct access to Winter Haven's Chain of Lakes for boating, fishing, and water recreation. Convenient location with easy access to downtown Winter Haven, shopping, dining, LEGOLAND, Highway 27, Interstate 4. Tampa and Orlando Airports.

1921 Manor Circle Se, Winter Haven
441 San Jose Drive, Winter Haven
$254,900
2 Beds ⋅ 2 Baths ⋅ L4965434 MLS
Welcome to 441 San Jose Drive, featuring a NEW ROOF installed in 2026 and located in the highly sought after Orchid Springs community of Winter Haven. This spacious 2 bedroom, 2 bathroom patio home sits on an oversized lot and offers a thoughtfully designed floorplan with generous living spaces and wonderful indoor and outdoor flow. The expansive kitchen opens to the large family room and dining area, creating an inviting space for everyday living and entertaining, while a separate living room and breakfast nook provide additional room to spread out. The spacious primary suite is privately positioned at the rear of the home and features an ensuite bathroom and walk in closet, while the second bedroom and full bathroom are located on the opposite side of the home. The home features a combination of tile and carpet flooring throughout. Step outside to enjoy both a charming courtyard and a large screened porch, offering multiple spaces to relax and enjoy the oversized lot. A wooded area along one side of the property is visible from the kitchen and adds a peaceful, secluded feel to the home. Additional features include a 2 car garage and gas water heater. Conveniently located in Winter Haven, this home is close to shopping, dining, medical facilities, recreation, and everyday conveniences. With its spacious floorplan, oversized lot, multiple outdoor living spaces, NEW ROOF, and desirable Orchid Springs location, 441 San Jose Drive is ready to welcome its next owner.

441 San Jose Drive, Winter Haven
100 El Camino Drive Unit 301, Winter Haven
$149,900
3 Beds ⋅ 3 Baths ⋅ B4902382 MLS ⋅ Granada Building BLDG.
Welcome to 100 El Camino Drive, Unit 301, a spacious corner-unit condominium located in the established Orchid Springs community of Winter Haven. As one of the larger residences in the building, this home offers an appealing combination of generous living space, privacy, convenience, and low-maintenance Florida living. The thoughtfully designed floor plan provides each bedroom with its own private full bathroom, making the home especially well suited for guests, multi-generational living, or owners who simply appreciate added privacy. As a corner unit, the residence benefits from an enhanced sense of separation and space, while additional storage provides room for seasonal items and everyday necessities. Major improvements include a 2023 Heating system and the home has been replumbed throughout, offering valuable updates for the next owner. Additional conveniences private storage, elevator access, and a designated parking space. Orchid Springs offers a peaceful residential setting highlighted by beautifully maintained grounds and scenic water features, along with access to a private community pool and clubhouse. The monthly association fee provides exceptional convenience by including water, gas, cable, internet, and trash service, helping simplify monthly expenses. Community amenities also include pool and clubhouse access, with association services supporting an easy, low-maintenance lifestyle. The location places you in the heart of everything Winter Haven has to offer. Enjoy convenient access to shopping, dining, medical services, downtown Winter Haven, LEGOLAND® Florida Resort, and the famous Winter Haven Chain of Lakes. Known as the “Chain of Lakes City,” Winter Haven offers abundant opportunities for boating, fishing, kayaking, waterfront dining, and other outdoor recreation while remaining conveniently positioned within Central Florida. Spacious, updated, and packed with included amenities, Unit 301 offers an excellent opportunity to enjoy comfortable condominium living in one of Winter Haven’s most distinctive established communities.

100 El Camino Drive Unit 301, Winter Haven
4230 Roberta Drive, Winter Haven
$360,000
5 Beds ⋅ 3 Baths ⋅ O6445712 MLS
Welcome to 4230 Roberta Drive in Winter Haven! This spacious single-family home offers 5 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
604 Sarner Pass Way, Winter Haven
$318,000
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
2500 21st Street Nw Unit 58, 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
1700 6th Street Nw Unit A38, 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. ***Please note this is a pet free community***

1700 6th Street Nw Unit A38, Winter Haven
1405 28th Street Nw, Winter Haven
$215,000
2 Beds ⋅ 1 Baths ⋅ L4963168 MLS
Price Improvement!! Owners Motivated!! 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
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