Winter Haven Homes with Private Yard Exterior Features

Winter Haven Homes with Private Yard Exterior Features

Welcome to Winter Haven, Florida – a charming city nestled in the heart of Polk County, where the sun shines bright and community spirit thrives. Known for its stunning lakes and picturesque landscapes, Winter Haven is a delightful blend of small-town warmth and modern conveniences. With its rich history and vibrant culture, residents enjoy a variety of recreational opportunities, from exploring the scenic Chain of Lakes to indulging in the local dining scene.

One of the standout features of homes in Winter Haven is the abundance of properties boasting private yards. Imagine stepping out into your own serene oasis, where you can unwind amidst lush greenery, host summer barbecues, or simply enjoy a peaceful evening under the stars. These homes offer the perfect backdrop for families, pet owners, or anyone who appreciates outdoor living.

Many of the residences in this area are designed with private yard exterior features that not only enhance your lifestyle but also provide a sense of privacy and tranquility. Whether you’re looking for a cozy bungalow or a spacious family home, you’ll find options that cater to your needs while allowing you to enjoy the Florida sunshine in your own backyard.

In Winter Haven, you’re not just buying a home; you’re investing in a lifestyle. With its friendly neighborhoods, excellent schools, and proximity to major attractions, this city is a fantastic place to call home. Discover the joys of living in Winter Haven, where comfort and community come together seamlessly. Your dream home with a private yard awaits!

Newest Winter Haven Homes with Private Yard Exterior Features

2500 Avenue O Nw, Winter Haven

2500 Avenue O Nw, Winter Haven

11 Beds ⋅ 5 Baths ⋅ Inwood #5 SubDv. ⋅ 33881 Zip Code

INCOME-PRODUCING INVESTMENT OPPORTUNITY IN WINTER HAVEN! Don’t miss this opportunity to own a four-unit investment property with $6,400 in potential monthly rental income at full occupancy! Currently generating $4,700 a month with three of the four units occupied, this property offers immediate cash flow and an opportunity for additional rental income. Situated on approximately 0.55 acres, this unique property features three structures with four separate rental units, offering an established income stream and excellent investment potential. The main residence, located at 2500 Avenue O NW, offers 4 bedrooms and 2 bathrooms and currently rents for $1,800 a month. An attached one-bedroom, one-bath apartment at 2502 Avenue O NW generates an additional $1,200 a month. At the rear of the property, a two-story duplex at 2504 Avenue O NW features two spacious three-bedroom, one-bath units, each renting for $1,700 a month. 3 of the 4 units are currently occupied with tenants on annual leases, providing immediate rental income for the next owner. The one-bedroom apartment and both duplex units received updates in January, including fresh paint and interior improvements. The upstairs duplex unit also features a recently replaced air conditioning system. A shared laundry room is conveniently located between the main residence and duplex. With a total of approximately 4,465 square feet of MLS-reported living space, multiple rental units, and established tenants already in place, this property presents a compelling opportunity for investors looking to expand their rental portfolio. Whether you’re a seasoned investor or looking to add your first multifamily property, this Winter Haven investment offers immediate income and long-term potential. Schedule your private showing today!

2500 Avenue O Nw, Winter Haven

1140 Tyler Loop, Winter Haven

1140 Tyler Loop, Winter Haven

3 Beds ⋅ 3 Baths ⋅ Peace Crk Reserve SubDv. ⋅ 33884 Zip Code

Short Sale. Short Sale. Welcome to 1140 Tyler Loop in Winter Haven! This two-story home offers 4 bedrooms, 2.5 bathrooms, and an open floor plan that connects the living, dining, and kitchen areas—ideal for everyday living and entertaining. The kitchen offers ample cabinet space, while the primary suite features a private bathroom and generous closet space. Additional bedrooms provide flexibility for guests, a home office, or hobbies. An attached two-car garage adds convenient parking and storage. Discover the possibilities and schedule your private showing today! Sale is subject to lender approval of the purchase price and terms. Additional time may be required for the short sale approval process.

1140 Tyler Loop, Winter Haven

6052 Kaley Drive, Winter Haven

6052 Kaley Drive, Winter Haven

4 Beds ⋅ 3 Baths ⋅ Sunridge Village East SubDv. ⋅ 33880 Zip Code

Welcome to 6052 Kaley Dr in Sunridge Village! This spacious 4-BEDROOM, 3-FULL-BATH POOL HOME PLUS a dedicated HOME OFFICE/BONUS ROOM offers 2,200 square feet of living space, an impressive outdoor entertaining area, and numerous valuable upgrades! THE SELLERS WILL OFFER $10,000 TOWARDS A RATE BUY DOWN WITH A FULL PRICE OFFER! Located in a desirable NO CDD community with an exceptionally LOW HOA OF JUST $165 PER YEAR, this home offers both space and affordability! THE ROOF, A/C SYSTEM, REMODELED KITCHEN, and INTERIOR PAINTING ALL DONE IN 2019, while additional recent updates provide even more value and appeal. This inviting two-story home features an OPEN FLOOR PLAN with TALL CEILINGS, attractive CROWN MOLDING, and generous living spaces designed for both everyday comfort and entertaining. The beautifully UPDATED ISLAND KITCHEN boasts GRANITE COUNTERTOPS, DOUBLE CLOSET PANTRIES, and STAINLESS STEEL APPLIANCES. The spacious living room features a distinctive SPECIALTY CEILING and FRENCH DOORS opening directly to the covered lanai, creating a wonderful connection between indoor and outdoor living. A separate dining room provides additional space for gatherings, while the convenient inside laundry room includes a washer and dryer. The spacious PRIMARY SUITE features a private EN SUITE BATHROOM with a WALK-IN SHOWER and relaxing GARDEN TUB. Three additional bedrooms provide comfortable accommodations, while the DOWNSTAIRS BONUS ROOM, currently used as a HOME OFFICE, offers incredible flexibility and POTENTIAL TO CONVERT INTO A FULL 5TH BEDROOM! With one of the THREE FULL BATHROOMS conveniently located downstairs, this layout provides excellent options for guests, multigenerational living, or anyone looking for additional living space. SPACIOUS 3 CAR GARAGE! Get the full FLORIDA EXPERIENCE by stepping outside to your own PRIVATE BACKYARD OASIS! The spacious COVERED LANAI features TILE FLOORING and OUTDOOR CEILING FANS, providing the perfect setting for relaxing or entertaining. Beyond the lanai, you'll discover a SCREEN-ENCLOSED IN-GROUND SWIMMING POOL & SPA, complete with an OUTDOOR BAR, BUILT-IN PLANTERS, and a charming TIKI-STYLE COVER OVER THE SPA! The pool area has also benefited from several improvements, including a NEW POOL PUMP in 2023, EPOXY-COATED POOL DECK PAVERS in 2023, and a POOL HEAT EXCHANGER replaced approximately 4.5 years ago. The current owners have also installed VINYL PRIVACY FENCING, creating a FULLY FENCED BACKYARD for additional privacy and enjoyment. Other improvements include a BEAUTIFUL NEW DOUBLE FRONT ENTRY DOOR installed in 2025, adding to the home's curb appeal. Situated on a generous .25-ACRE LOT in Sunridge Village, this property offers an EXCELLENT CENTRAL FLORIDA LOCATION! Enjoy convenient access to the POLK PARKWAY, providing easy connections toward TAMPA and ORLANDO, as well as nearby HIGHWAY 60, offering a direct route west toward TAMPA and east toward VERO BEACH and Florida's Atlantic Coast. Shopping, restaurants, and everything Winter Haven has to offer are also conveniently located nearby. With ALL THE UPDATES, 4 BEDROOMS PLUS A FLEXIBLE DOWNSTAIRS BONUS ROOM, 3 FULL BATHROOMS, FULLY FENCED BACKYARD, and spectacular SCREENED POOL & SPA AREA, this home offers an outstanding combination of space, improvements, and Florida living! Add in the NO CDD and incredibly LOW ANNUAL HOA of just $165, and this is an opportunity you won't want to miss. Schedule your private showing today!

6052 Kaley Drive, Winter Haven

3223 Avenue S Nw, Winter Haven

3223 Avenue S Nw, Winter Haven

2 Beds ⋅ 1 Baths ⋅ Hundred Lakes Corps Inwood SubDv. ⋅ 33881 Zip Code

Beautifully updated 2-bedroom, 1-bath home featuring a 2-year-old roof, new interior and exterior paint, new flooring throughout, and a remodeled bathroom. The brand new kitchen offers new cabinets and new upgraded stainless steel appliances, creating a clean and functional space. This home includes 728 sq. ft. of living area on an oversized 0.17-acre lot, providing room for outdoor enjoyment. Exterior features include a screened side porch, laundry room, carport, and two backyard sheds for storage or projects. Located near Winter Haven’s Chain of Lakes, shopping, dining, parks, and major roadways. A move-in-ready property with modern updates and convenient access to local amenities. Buyer is responsible for verifying all measurements, square footage, and layout details.

3223 Avenue S Nw, Winter Haven

188 Black Skimmer Lane, Winter Haven

188 Black Skimmer Lane, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Lake Deer SubDv. ⋅ 33880 Zip Code

WELCOME HOME! Discover this beautiful single-family home featuring 3 bedrooms, 2 bathrooms, and 1,720 square feet of living space, built in 2020 and located in Winter Haven! Designed with comfort and functionality in mind, this residence showcases a beautiful open floor plan that seamlessly connects the kitchen, dining, and living areas, creating a spacious and inviting atmosphere perfect for everyday living and entertaining. The modern kitchen features elegant granite countertops, stainless steel appliances, and a functional layout that makes meal preparation and gatherings a pleasure. The spacious primary bedroom provides a comfortable retreat, while two additional bedrooms allow flexibility for guests, a home office, or additional living needs. ONE OF THE PROPERTY'S STANDOUT FEATURES IS THE SOLAR PANEL SYSTEM, WHICH WILL BE PAID IN FULL BY THE SELLER AT CLOSING, allowing the new owner to enjoy the potential benefits of lower electricity bills without assuming the existing solar financing. Step outside to your fully fenced, private backyard, an ideal setting for outdoor gatherings, weekend barbecues, pets, or simply relaxing in the Florida sunshine. The property also features a SPACIOUS 2-CAR GARAGE, providing ample room for parking and additional storage. Conveniently situated near shopping, dining, schools, and major roadways, this home combines the appeal of newer construction with everyday convenience. Whether you're searching for a primary residence or an investment opportunity, this property is an excellent choice. Don't miss this fantastic opportunity! Schedule your private showing today!

188 Black Skimmer Lane, Winter Haven

7123 Summit Drive, Winter Haven

7123 Summit Drive, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Summit East Ph 01 SubDv. ⋅ 33884 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in a the quiet East Summit neighborhood. Thoughtfully updated and move-in ready, this property offers both comfort and style with a spacious, well-designed layout. The private primary suite features a generous bathroom complete with a relaxing soaking tub, separate walk-in shower, and dual vanity sinks. Throughout the home, you'll find attractive tile flooring that creates a seamless and modern feel. The kitchen is well-equipped with quality appliances and provides plenty of space for cooking and entertaining. Recent improvements add even more value and peace of mind, including a new roof installed in 2025, fresh interior paint, a freshly painted garage, a brand-new bathroom sink, updated light fixtures, and new AC vents throughout the home. Step outside to enjoy the fully fenced backyard, offering the perfect space for pets, outdoor gatherings, gardening, or simply unwinding in your own private retreat. Conveniently located near LEGOLAND Florida Resort, shopping, dining, schools, and major roadways, this home combines a peaceful residential setting with easy access to all that Winter Haven has. Don't miss this opportunity to own a beautifully updated home in one of Winter Haven's desirable, quiet neighborhoods. Schedule your private showing today!

7123 Summit Drive, Winter Haven

888 Twin Oaks Lane, Winter Haven

888 Twin Oaks Lane, Winter Haven

5 Beds ⋅ 5 Baths ⋅ Twelve Oaks Estates SubDv. ⋅ 33880 Zip Code

Welcome to 888 Twin Oaks Lane, where striking custom architecture, luxury features, four acres of privacy, and resort-style outdoor living come together in prestigious, gated Twelve Oaks Estates. Built by respected custom builder Alan Ulch on a quiet cul-de-sac, this distinctive residence offers 4,565 square feet of heated living space with five bedrooms, four full bathrooms, one half bathroom, and a versatile bonus room. A dramatic two-story foyer and living room showcase soaring 22-foot ceilings, an architectural catwalk, and custom shiplap detailing. Abundant windows fill the home with natural light and frame peaceful property views, complemented by engineered wood flooring, oversized doorways, plantation shutters, and custom window treatments with motorized shades. The chef-inspired kitchen pairs premium Bosch and Thermador appliances with Misterio quartz countertops, floor-to-ceiling cabinetry, a custom range hood, and floating shelves. A built-in coffee maker, Ice-O-Matic nugget ice machine, and separate wine and beverage refrigeration elevate everyday living and entertaining. Two oversized sinks, concealed small-appliance closets, deep island drawers, and an expansive walk-in pantry provide exceptional storage and functionality. The main-level primary suite offers direct pool access and a spa-like bathroom with an oversized soaking tub, floor-to-ceiling tiled shower, dual vanities, dedicated makeup area, and two expansive walk-in closets with custom shelving. A separate main-level mother-in-law suite welcomes extended family or guests. Oversized secondary bedrooms with walk-in closets, an office nook, and a spacious bonus room offer flexibility for work and recreation. The oversized laundry and mudroom feature abundant counter space, a utility sink, laundry chute, barn door, and dedicated pet-washing station. Expansive covered porches with elegant pavers and wood-planked ceilings invite you to enjoy the peaceful setting. Relax on the twin-size bed swing and enjoy the nature. Expansive sliding glass doors connect the interior to an oversized custom heated saltwater pool with a sun shelf, integrated spa, wraparound seating bench, and beautiful lighting. An outdoor shower and plumbing provisions for a future outdoor kitchen enhance this private retreat. Beautiful acreage framed by horse fencing provides room to gather, play, and explore. Quality construction and modern conveniences include Hardie board siding, metal roofing over the porches, whole-home spray foam insulation, a Generac whole-house generator, Culligan water treatment system, three tankless water heaters, two central air-conditioning systems plus a mini-split, and an integrated residential fire sprinkler system. An oversized driveway provides ample parking. With controlled gated access and paved community roads, Twelve Oaks Estates offers a peaceful home base convenient to Winter Haven, Lakeland, Auburndale, and Bartow, with shopping, dining, downtown entertainment, parks, lakes, and boating nearby. Polk Parkway connections to I-4 put Tampa, Orlando, both international airports, and attractions including LEGOLAND Florida, Walt Disney World, Universal Orlando, and Busch Gardens Tampa Bay within reach. Grand spaces for gathering. Quiet places to retreat. Four private acres to call your own. 888 Twin Oaks Lane brings together custom craftsmanship, luxury finishes, resort-style outdoor living, and everyday comfort for an exceptional expression of private estate living.

888 Twin Oaks Lane, Winter Haven

273 Mariposa Street, Winter Haven

273 Mariposa Street, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Florida Highland Co SubDv. ⋅ 33884 Zip Code

Welcome to 273 Mariposa St. in the desirable Orchid Springs Patio Homes community in Winter Haven! This beautifully maintained 3-bedroom, 2-bathroom home has undergone MAJOR UPGRADES THROUGHOUT in 2022/2023, offering a wonderful combination of modern improvements, spacious living areas, and Florida charm! The versatile floor plan features a formal living room, dining room, and family room, with luxury vinyl plank flooring throughout much of the home and tile flooring in the family room. The inviting living room features vaulted ceilings accented by beautiful wood beams, adding warmth and character. The FULLY REMODELED KITCHEN is a standout feature, offering gorgeous granite countertops, updated cabinetry, a center island, stylish backsplash, and stainless steel appliances, including built-in ovens, cooktop, microwave, and dishwasher. The dining room is enhanced by classic wainscoting and sliding glass doors that fill the space with natural light and provide easy access to the family room and outdoor living areas. The bathrooms have received attractive updates! The guest bathroom features an updated vanity, toilet, tile, backsplash, and fresh paint. The spacious primary suite offers a private ensuite bathroom and generous closet space. The list of MAJOR IMPROVEMENTS continues with a COMPLETE HOME REPLUMBING, COMPLETE ELECTRICAL REWIRING WITH UPDATED OUTLETS THROUGHOUT, WINDOWS REPLACED with double-pane windows, updated baseboards, interior repainting, updated blinds, and a NEW WATER HEATER installed in September 2024. The home also features a well-maintained Trane A/C system, an attractive METAL ROOF and an attached 2-car garage with built-in storage cabinetry and a replaced garage door opener. Step outside and enjoy Florida living from the SCREEN-ENCLOSED PATIO or the additional open patio featuring a firepit, perfect for relaxing or entertaining! Situated on a desirable .14-acre CORNER LOT, the property showcases beautiful, mature oak and palm trees, along with thoughtfully maintained landscaping. Orchid Springs Patio Homes offers residents access to a COMMUNITY POOL and CLUBHOUSE, providing a wonderful opportunity to enjoy the Florida lifestyle. LOCATION IS ANOTHER GREAT FEATURE! Conveniently situated near restaurants, medical facilities, churches, and shopping, with a NEW PUBLIX just approximately 5 minutes away! The home also offers easy access to HIGHWAY 27 and is just a short drive from LEGOLAND FLORIDA RESORT, making it easy to enjoy everything Central Florida has to offer. With its extensive upgrades, generous living spaces, inviting outdoor areas, and convenient location, this home is a wonderful opportunity to enjoy Florida living. Schedule your private showing today!

273 Mariposa Street, Winter Haven

251 Greenfield Road, Winter Haven

251 Greenfield Road, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code

VACANT AND PRICED TO SELL! NEW ROOF 2025! 2 BED 2 BATH CONCRETE BLOCK STUCCO (CBS) HOME IN GUARD GATED CYPRESSWOOD GOLF AND COUNTRY CLUB, WINTER HAVEN FL 33884. Vacant single story home on a 0.44 acre lot with an attached garage, central air, and no CDD. Roof replaced 2025 and water heater 2017. The home needs some work and is priced for its condition. Seller is open to making repairs needed for FHA or conventional loan approval. Cypresswood is a golf cart friendly golf course community with a 24 hour guard gate, 18 hole championship golf course, clubhouse, community pool, and tennis. Located in Polk County near Legoland Florida, Cypress Gardens, the Chain of Lakes, shopping, dining, US 27, and the I-4 corridor between Orlando and Tampa. FHA, VA, conventional, and cash welcome. Sold as is.

251 Greenfield Road, Winter Haven

503 William Avenue, Winter Haven

503 William Avenue, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code

Be the First to Enjoy This Beautifully Renovated Home! Featuring brand-new paint, flooring, kitchen, bathrooms, windows, doors and AC. This home offers modern finishes and a bright, open layout with granite countertops, new cabinetry, and stainless-steel appliances. Situated on an oversized lot in a quiet, established neighborhood with NO HOA, enjoy a spacious yard, ample parking, and plenty of room to entertain. Conveniently located near shopping, dining, and major roadways, this move-in-ready home is a must-see!

503 William Avenue, Winter Haven

417 Avenue G Se, Winter Haven

417 Avenue G Se, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Lawing Sub SubDv. ⋅ 33880 Zip Code

MORE SPACE, MORE FLEXIBILITY, MORE POSSIBILITIES. Discover the charm and potential of this inviting property located in Winter Haven! Featuring 3 bedrooms and 2 bathrooms, this home offers a comfortable and functional layout with no carpet throughout, making everyday living and maintenance a breeze. A standout feature is the additional flexible space with its own full bathroom, ideal for accommodating guests, creating a private home office, or enjoying extra room for your personal needs. Step outside and discover an expansive, fully fenced backyard, offering a wonderful setting for outdoor entertaining, gardening, weekend gatherings, or simply relaxing under the Florida sunshine. A convenient covered carport adds everyday practicality. Whether you're looking for comfortable indoor living, versatile extra space, or a generous outdoor area to enjoy, this property brings it all together. **A unique opportunity with space to make it your own! Schedule your private showing today and experience everything this property.

417 Avenue G Se, Winter Haven

1217 Michelangelo Lane, Winter Haven

1217 Michelangelo Lane, Winter Haven

4 Beds ⋅ 4 Baths ⋅ Estates/Lk Florence SubDv. ⋅ 33884 Zip Code

NO CDD • LOW HOA • SPACIOUS CORNER LOT! Space, style, and modern Florida living come together in this impressive Winter Haven home offering nearly 3,000 SQ. FT. with 4 BEDROOMS + a dedicated OFFICE/BONUS ROOM, 3.5 BATHROOMS + a HUGE UPSTAIRS LOFT. The PRIMARY SUITE and dedicated OFFICE are both conveniently located on the first floor, creating a highly functional layout with privacy, flexibility, and plenty of room to spread out. LOCATION IS ANOTHER MAJOR ADVANTAGE! Enjoy convenient access to LEGOLAND Florida Resort, shopping, dining, entertainment, beautiful lakes, outdoor recreation, and major roadways connecting you throughout Central Florida—all while enjoying the benefits of NO CDD and LOW HOA fees.Some rooms are Virtually Staged Step inside and you’ll immediately appreciate the OPEN-CONCEPT LAYOUT and sense of space. Beautiful CERAMIC TILE flows throughout the first floor, creating a seamless transition between the kitchen, dining, and living areas. The kitchen features GRANITE COUNTERTOPS, plenty of cabinetry and storage, and an open design perfect for everyday living and entertaining. The PRIMARY SUITE on the first floor provides privacy and convenience, while the separate OFFICE/BONUS ROOM, also downstairs, is ideal for working from home, a study, hobby room, playroom, or additional flex space. Head upstairs and the space continues! A HUGE LOFT creates an entirely separate living area—perfect for a MEDIA ROOM, GAME ROOM, HOME GYM, KIDS’ LOUNGE, or SECOND FAMILY ROOM. The remaining three bedrooms are upstairs, offering great separation from the primary suite, along with generous walk-in closets and plenty of storage throughout the home. Outside, the LARGE CORNER LOT gives you even more room to enjoy. The FULLY FENCED BACKYARD and COVERED LANAI create the perfect setting for entertaining, weekend BBQs, pets, or simply relaxing and enjoying the Florida lifestyle. The home also features a FULL GUTTER SYSTEM for added convenience. If you’ve been looking for SIZE, MODERN STYLE, and FLEXIBLE LIVING SPACE, this home delivers—4 BEDROOMS + OFFICE/BONUS ROOM + HUGE LOFT, nearly 3,000 sq. ft., a first-floor primary suite, spacious fenced corner lot, NO CDD and LOW HOA. Schedule your private showing today and experience everything this beautiful Winter Haven home has to offer!

1217 Michelangelo Lane, Winter Haven

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