Winter Haven Homes with Courtyard Exterior Features

Winter Haven Homes with Courtyard Exterior Features

Welcome to Winter Haven, Florida – a picturesque city nestled in the heart of Polk County, renowned for its stunning chain of lakes and vibrant community spirit. With its warm climate, friendly neighborhoods, and rich cultural heritage, Winter Haven is an ideal destination for those seeking a tranquil yet engaging lifestyle. Whether you’re an outdoor enthusiast or someone who appreciates art and history, this charming city offers a little something for everyone.

One of the standout features of homes in Winter Haven is their enchanting courtyard exterior designs. These thoughtfully crafted homes often showcase beautifully landscaped courtyards that serve as serene retreats, perfect for enjoying the balmy Florida weather. Imagine sipping your morning coffee surrounded by lush greenery and vibrant flowers, or hosting evening gatherings under the stars in your private outdoor oasis. Courtyards not only enhance the aesthetic appeal of your home but also provide an inviting space for relaxation and entertainment.

In addition to their stunning exteriors, many homes in Winter Haven are designed with open floor plans and modern amenities, ensuring comfort and convenience for families of all sizes. The community is also conveniently located near shopping, dining, and recreational activities, making it easy to embrace the vibrant lifestyle that Winter Haven has to offer.

Whether you’re looking to buy your first home or seeking a peaceful retreat, Winter Haven’s homes with courtyard features promise a unique blend of charm and comfort. Come explore this delightful city and discover your dream home in the heart of Florida!

Newest Winter Haven Homes with Courtyard Exterior Features

2 Beds ⋅ 1 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code

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

2 Beds ⋅ 1 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code

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

3 Beds ⋅ 3 Baths ⋅ Hartridge Landing SubDv. ⋅ 33881 Zip Code

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

2 Beds ⋅ 2 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code

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

4 Beds ⋅ 2 Baths ⋅ Carefree Cove SubDv. ⋅ 33881 Zip Code

Seller to pay all Closing costs for Potential buyer.. 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

2 Beds ⋅ 2 Baths ⋅ Cypresswood Villas/Green Bldg SubDv. ⋅ 33884 Zip Code

Situated in the desirable golfing community of Cypresswood Golf & Country Club, this lovely 2-bedroom, 2-bath townhome offers comfort, style, and beautiful golf course views. Upon arrival, you'll be welcomed by a charming courtyard adorned with pavers, creating a warm and inviting entrance. A glass storm door and smart lock entry provide both convenience and security. Inside, luxury vinyl plank flooring flows throughout the main living areas, enhancing the home's modern appeal and ease of maintenance. The open-concept floor plan features an updated kitchen with maple wood cabinetry embellished with brushed nickel hardware and soft-close hinges. Corian countertops beautifully complement the tile backsplash, while the custom center island serves as the heart of the home. Additional features include a stainless steel appliance package, recessed lighting, and a closet pantry for ample storage. The adjacent dining area is filled with natural light from an overhead solar tube skylight, creating a bright and cheerful space for meals and gatherings. The spacious living room features a convenient dry bar and oversized sliding glass doors that showcase peaceful views of the golf course. The primary bedroom suite serves as a relaxing retreat, offering dual closets and sliding glass doors leading to the Florida Room. The remodeled en-suite bathroom features a comfort-height vanity with Corian countertops, bronze fixtures, and a walk-in shower with a frameless glass enclosure and safety grab bars. The guest bedroom includes luxury vinyl plank flooring, a custom closet organizer system, and views of the private courtyard. The spacious Florida Room provides the perfect place to relax and unwind while enjoying tranquil golf course views through two oversized sliding glass doors. Additional Features: Laundry room with washer and dryer, Comfort-height toilets, Exterior lighting, Metal roof, Gutters with gutter guards. This home is being offered turnkey and fully furnished, making it truly move-in ready. Conveniently located within walking distance of the community clubhouse, restaurant, pub, swimming pool, and tennis courts, this property offers exceptional accessibility to Cypresswood's amenities. The monthly HOA fee of $320 includes: Exterior painting Roof maintenance Lawn care Additional memberships are available for golf and fitness center access. The picturesque Cypresswood Golf & Country Club features beautifully maintained grounds, a 24-hour manned gated entrance, and a welcoming lifestyle centered around golf, recreation, and community living.

664 Clubhouse Road, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Orchid Springs Patio Homes SubDv. ⋅ 33884 Zip Code

Welcome to this wonderful 3 bedroom, 2 bathroom home located on a spacious corner lot with NO rear neighbors in the desirable Orchid Springs community in SE Winter Haven. NEW METAL ROOF PUT ON IN 2021 AND AC REPLACED IN 2023! Offering a versatile split-bedroom floor plan, this home features a living room, dining room and family room, providing plenty of space for both everyday living and entertaining. The bright and open living room showcases vaulted ceilings & glass doors that lead to a private courtyard, creating a seamless connection between indoor & outdoor living. The kitchen is centrally located and offers a spacious breakfast bar, closet pantry & ample cabinet & counter space, making it ideal for meal preparation & gathering with family & friends. The primary suite provides a relaxing retreat with a walk-in closet, garden tub, separate shower & also has access directly to the screened patio. Ceramic tile flooring throughout the home offers both durability & easy maintenance. Additional features include a 2-car garage with built-in storage, utility sink, and washer/dryer hookups. The fenced backyard offers privacy & room for pets, gardening, or outdoor enjoyment. Residents of Orchid Springs enjoy access to community amenities including a clubhouse & swimming pool, all while being conveniently located near shopping, dining, churches, medical facilities, golf courses & major roadways. Don't miss this opportunity to own a spacious home in one of Winter Haven's most established communities.

381 San Jose Drive, Winter Haven

4 Beds ⋅ 2 Baths ⋅ Pollard Shores SubDv. ⋅ 33881 Zip Code

Welcome home to this stunning lakefront 4-bedroom, 2-bath retreat on Lake Hamilton featuring a courtyard outside along with lake views from both the sitting areas and the dining rooms inside of the home. The rooms are spacious, ideal for everyday living and remote work. Whether you're hosting, friends, enjoying family meals, or taking in the scenery after a long day. Spending mornings with coffee, enjoy evenings outdoors, or entertain with ease that comes from a deck right where you want to be, overlooking the lake lifestyle. The community is located near daily conveniences, including shopping, dining, and nearby attractions such as Legoland. From the first look at the views to the comfort of this home, this lakefront home is ready to be enjoyed. Don't miss the opportunity to own a home with lake views in multiple living areas and the added benefit of a deck for outdoor relaxation.

1210 W Lake Hamilton Drive, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Cypresswood Villas/Green SubDv. ⋅ 33884 Zip Code

Enjoy the Florida Country Club Lifestyle in this affordable and updated 2 bedroom 2 bath villa. Recent updates include new luxury vinyl flooring, new dishwasher and new microwave. MOVE IN CONDITION. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and pickleball/tennis courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix just opened a brand new location just a mile down the road which is sure to attract other popular businesses.

1026 Medinah Drive, Winter Haven

3 Beds ⋅ 3 Baths ⋅ North Lake Elbert Heights SubDv. ⋅ 33881 Zip Code

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

3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code

Welcome to resort-style living in the highly sought-after Lake Ashton Golf Club Community! This impeccably maintained home is nestled on a quiet and secluded street, offering the perfect combination of privacy, comfort, and an active Florida lifestyle. From the moment you arrive, you will appreciate the pride of ownership and pristine condition of this beautiful residence. Designed for both everyday living and entertaining, the home offers spacious living areas, abundant natural light, and a floor plan that flows effortlessly throughout. One of the most valuable features of this property is that the CDD bond has been fully paid off, providing significant long-term savings and added value for the new owner. Lake Ashton is one of Central Florida's premier gated 55+ communities, offering an unmatched array of amenities and activities. Residents enjoy access to two private 18-hole championship golf courses, including one of the most challenging and highly regarded courses in the region, making it a favorite among golf enthusiasts. The community also features two expansive clubhouses, a state-of-the-art health and fitness center, resort-style pools, tennis and pickleball courts, bowling lanes, movie theater, ballroom, restaurant and lounge, arts and crafts facilities, numerous social clubs, and a private marina with access to beautiful Lake Ashton. Whether you are looking for an active retirement, a seasonal retreat, or your forever home, this exceptional property offers the perfect opportunity to enjoy the Florida lifestyle at its finest. Schedule your private showing today and discover why so many residents proudly call Lake Ashton home.

5312 Nicklaus Drive, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Stonebridge Ph 02 SubDv. ⋅ 33880 Zip Code

WELCOME HOME TO STONEBRIDGE! Step through your private, custom-gated Courtyard into a beautifully updated Stonebridge Patio Home that is truly MOVE-IN-READY! NEWER ROOF (2024), NEWER ELECTRIC PANEL (2024), NEWER WINDOWS AND SLIDERS (2022), NEW GUTTERS & DOWNSPOUTS (2026). This fabulous property is located in FEMA Zone X, a low-risk flood zone. From the moment you enter, you'll be impressed by the gorgeous PORCELAIN TILE FLOORING that flows throughout the main living areas, creating an elegant and welcoming atmosphere. The spacious Great Room serves as the heart of the home, featuring a stunning wood-paneled fireplace that creates a warm focal point for relaxing or entertaining. Newer (2022) Sliding Doors lead to a private, covered, and screened patio, offering the perfect place to enjoy your morning coffee, unwind after a long day, or entertain guests in a peaceful outdoor setting. Adjacent to the Great Room is a dedicated dining area with a convenient pass-through to the kitchen. The beautifully updated kitchen showcases rich cabinetry, granite countertops, stainless steel appliances, and a breakfast nook, perfect for preparing meals and gathering with family and friends. Enjoy the convenience of the sliding doors out to the private courtyard. Retreat to the spacious primary suite, complete with a walk-in closet and an updated ensuite bath featuring a walk-in shower and modern finishes. The guest bedroom offers generous closet space and flexibility for visitors, a home office, or craft room. The beautifully renovated guest bathroom features a striking designer tile accent wall, creating a stylish space for family and guests. Additional highlights include updated bathrooms, a washer and dryer, a one-car garage, neutral décor throughout, and move-in-ready condition. Take your pick of two outdoor escapes: the gated front courtyard or the covered, screened back patio. There is a one-car garage and an in-home laundry. Residents of Stonebridge enjoy access to a community pool and a convenient location close to shopping, restaurants, churches, medical facilities, and everyday conveniences. Located in the heart of Winter Haven, known as Florida's Chain of Lakes City, residents enjoy boating, fishing, waterfront dining, golf courses, beautiful parks, and year-round recreation. Winter Haven is also home to LEGOLAND Florida Resort and offers convenient access to both Orlando and Tampa, making it an ideal location for full-time residents, seasonal homeowners, or anyone seeking the Florida lifestyle. SCHEDULE A SHOWING TODAY!!

2026 Kings Crossing Sw, Winter Haven

Start Your Search