Winter Haven Homes with Rain Gutters Exterior Features

Winter Haven Homes with Rain Gutters Exterior Features

Welcome to Winter Haven, Florida—a picturesque gem nestled in Polk County that seamlessly combines small-town charm with modern conveniences. Known for its stunning chain of lakes, Winter Haven offers a vibrant lifestyle filled with outdoor adventures, cultural experiences, and a warm community spirit. With a population that embraces both the tranquility of nature and the excitement of city living, it’s no wonder that Winter Haven is becoming a sought-after destination for families, retirees, and everyone in between.

When it comes to finding your dream home in this delightful city, consider properties featuring rain gutters—an essential exterior feature that enhances both aesthetics and functionality. Homes equipped with rain gutters not only protect your property from water damage but also contribute to effective drainage, keeping your landscape looking pristine. In the picturesque neighborhoods of Winter Haven, you’ll discover a variety of homes, from charming bungalows to contemporary designs, all boasting that practical yet stylish touch of rain gutters.

Living in Winter Haven means you’re just moments away from beautiful parks, recreational activities, and the renowned LEGOLAND Florida Resort. Whether you’re enjoying a sunny day by the lake or exploring the local dining scene, this community offers a welcoming atmosphere that feels like home.

So, if you’re ready to embrace the Florida lifestyle, explore the diverse range of homes in Winter Haven with rain gutters and start your journey towards finding the perfect place to call your own!

Newest Winter Haven Homes with Rain Gutters Exterior Features

1841 5th Street Se, Winter Haven
$339,000
3 Beds ⋅ 2 Baths ⋅ Southeast Terrace SubDv. ⋅ 33880 Zip Code
Virtually Staged. Welcome to 1841 5th Street SE in Winter Haven, Florida, a well-maintained 3 bedroom, 2 bath home offering approximately 1,917 square feet of living space with a combination of practical upgrades, like luxury vinyl flooring, makes a comfortable indoor living, and a versatile outdoor space.One of the standout advantages is NO HOA, offering added ownership flexibility for buyers and investors alike. Whether you're searching for a primary residence, second home, or potential long-term rental addition to your portfolio, this property presents an appealing opportunity, subject to applicable rental and local regulations. Several important improvements have already been completed, including a roof replaced in August 2026, irrigation and irrigation well updated approximately three months ago, a water heater approximately four years old, newer carpeting, double-pane windows, and an updated faucet. The home is natural gas connected, has a reverse-osmosis water system, security system, generous closets, and cable access in each room. The second bathroom features double vanities, and the bathroom vanities were updated approximately five years ago. The garage features an epoxy-coated floor, adding a clean, finished touch to this functional space. Outdoors, you'll find a screened patio, and a fully fenced backyard, established back and side-yard pathways approximately four years old, a dry storage shed with electricity, and a newer driveway retaining wall providing useful space for pets, gardening, entertaining, storage, hobbies, and everyday outdoor living. Beyond the property, enjoy the lifestyle and convenience that make Winter Haven and Central Florida an attractive place to call home. Get your groceries at Publix or Walmart. Nearby recreation includes South Central Park, Trailhead Park Playground, Rotary Park, Lake Shipp Park, and South Lake Howard Nature Park. Family entertainment and attractions include LEGOLAND® Florida Resort, PEPPA PIG Theme Park Florida, Planet Obstacle, and Cowboy Adventure Park. Discover within short distance local dining favorites such as Olive Garden, Outback Steakhouse, First Watch, Panera Bread, Starbucks, Red Lobster. Then within a short drive Harborside, Longhorn & Texas Roadhouse, Harry's Old Place, Bowen Yard, Panda Express and Lucille's American Cafe, along with convenient access to healthcare services including Winter Haven Hospital, AdventHealth emergency care, and BayCare Urgent Care. With its combination of recent improvements, outdoor functionality, location, and ownership flexibility, 1841 5th Street SE offers an opportunity worth exploring for homeowners and investment-minded buyers. Schedule your private showing today!

1841 5th Street Se, Winter Haven
575 Saint Andrews Road, Winter Haven
$286,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Golf Course Living with Total Peace of Mind! Welcome to your worry-free oasis on the green. Nestled within this beautiful, gated community of Cypresswood Golf and Country Club, this beautifully maintained 2-bedroom, 2-bathroom golf-front home offers the perfect blend of active resort living and quiet tranquility. Imagine waking up, stepping onto your private patio, and sipping your morning coffee while looking out over pristine, rolling fairway. What truly sets this home apart is that every major expense has already been taken care of for you. You can move in with absolute confidence, knowing you won't have to worry about costly upgrades or repairs for years to come. Recent premium updates include: •Brand New HVAC System (2024): Brand new inside and out for peak energy efficiency. •New Roof & Structural Updates (2022): Completely replaced roof, overhang, and facia boards. •Total Peace of Mind (2021): The entire home was fully re-plumbed. •Modern Conveniences: Updated kitchen and bathroom fixtures, a new garage •Modern Conveniences: Updated kitchen and bathroom fixtures, a new garage door opener, a new garbage disposal, and upgraded GFCI outlets. Storage is never an issue with the massive 23x23 oversized garage—offering ample space for your vehicles, workshop, and of course, your golf cart. Opportunities in Cypresswood like this do not last long. Don’t wait to start living your dream golf-course lifestyle—call today to schedule your private showing!

575 Saint Andrews Road, Winter Haven
5344 Nicklaus Drive, Winter Haven
$310,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph I SubDv. ⋅ 33884 Zip Code
Home for Sale in Lake Ashton, a Florida Retirement Community with Two (2) Golf Courses, Resort Style Amenities and Planned Activities like Trivia, Bingo, Dances, Day Trips, Holiday Events and MORE! This 3 Bedroom and 2 Bath home with over 1,600 sq. ft. living area would be a great seasonal home. The furniture in this home is negotiable. The exterior of this home has paver drive and walk ways, mature and well maintained landscape with rock-scape and landscape edging, a screened entry at the Front Door, and a Covered Lanai, on the front of the home, which is large enough for chairs. An irrigation system provides water to the large and beautiful Palm tree and other mature landscape around the home. This seasonally occupied and well maintained home offers an Open and Spacious Split Floor Plan with NO CARPET ANYWHERE! The kitchen features SS appliances (oven-December 2022, refrigerator 2021), Corian countertops, Dinette area with Bay Windows, Step Up breakfast bar and closet pantry. New Anderson Windows have been installed in the Dining room, Primary Bedroom and Primary Bathroom. Laminate flooring is in each of the bedrooms. The Primary Suite has 2 large walk-in closets, His/Her comfort height vanities, a Water closet and Large walk-in shower. The washer/dryer in the laundry room will be included in the sale of this home. The outdoor living area offers a 26 x 10 rear screened lanai and large paver area that is great for grilling. The 2 car garage is equipped with a "Skeeter Beater" for privacy and enjoying the cool cross breeze! Lake Ashton that offers 2 clubhouses, indoor and outdoor heated pools, pickle ball, tennis courts, racquetball, basketball, fitness centers, movie theaters, craft room, media center, several private lakes, private boat ramp/slips and more!! Come and enjoy your retirement and carefree living in the beautiful gated and guarded community of Lake Ashton today!

5344 Nicklaus Drive, Winter Haven
651 Lake Dexter Circle, Winter Haven
$200,000
3 Beds ⋅ 2 Baths ⋅ Lake Dexter Woods Ph 02 SubDv. ⋅ 33884 Zip Code
The property you are inquiring about is located in Winter Haven, FL, in the Lake Dexter area of Polk County. Ok, straight up - This house needs work! The price reflects the evidence. We are here to sell this house because of location AND under market value "As-is". We know what it needs! We also know what you need! Cheap house to offset interest rates, cash to investment equity, or a handy-dandy family looking to help their start-up children quit paying rent, or winter home, or a side slide revenue generator, ANY of the above on this 3-bedroom, 2-bathroom, 1,345 sq.ft. home, with a screened lanai and a garage. It's ready to close in Ten so offer up! Call, text, email.

651 Lake Dexter Circle, Winter Haven
2900 Crump Road, Winter Haven
$425,000
4 Beds ⋅ 3 Baths ⋅ Magnolia Shores SubDv. ⋅ 33881 Zip Code
RARE LAKEFRONT OPPORTUNITY on beautiful Lake Hamilton, part of the northern CHAIN OF LAKES! Situated on an expansive .73-ACRE LOT with approximately 100 FEET OF DIRECT LAKE FRONTAGE, this well-built 4-bedroom, 2.5-bath POOL HOME offers an incredible waterfront setting, NO HOA, plenty of space and endless potential to create your own Florida retreat. A LARGE DRIVEWAY and OVERSIZED PARKING AREA provide plenty of room for multiple vehicles, guests, a boat or other recreational toys, while the DETACHED GARAGE offers even more parking, storage or workshop possibilities. Inside, the spacious living room features VAULTED CEILINGS accented by charming WOOD BEAMS, adding warmth and character to the home. The kitchen offers CORIAN COUNTERTOPS, plenty of cabinetry and stainless-steel appliances, including the STOVE, MICROWAVE and DISHWASHER. Throughout the home, you'll appreciate the abundance of STORAGE and ADDITIONAL CLOSET SPACE. The primary bathroom features an UPDATED, FULLY TILED, EASY-ACCESS SHOWER, and the WASHER AND DRYER located inside the laundry room will also remain with the home. Step outside and discover what makes this property truly special. Enjoy peaceful lake views, mature surroundings, a PRIVATE POOL and generous outdoor living space, all with plenty of room to create your own private waterfront oasis. With approximately 100 feet of direct frontage on Lake Hamilton, there is incredible potential to take full advantage of the Florida lakefront lifestyle. The home is in need of repairs and updating, presenting an excellent opportunity for buyers with vision to renovate, customize and add value while taking advantage of a hard-to-find affordable waterfront property. Important updates include a ROOF (2018), A/C (09/2024) and WATER HEATER (2025). Lake Hamilton is part of the Northern Chain of Lakes, offering access to interconnected waterways for BOATING, FISHING, WATERSPORTS and scenic cruising. Enjoy the tranquility of lakefront living while remaining conveniently located near Hwy 27 and located very close to Winter Haven, LEGOLAND Florida Resort and Port 27. Whether you're searching for a full-time residence, vacation home or renovation project, this property offers a RARE COMBINATION of ACREAGE, DIRECT LAKE FRONTAGE, A PRIVATE POOL, DETACHED GARAGE, OVERSIZED PARKING, NO HOA and tremendous potential in a beautiful Central Florida waterfront setting.

2900 Crump Road, Winter Haven
37 Lake Eloise Lane, Winter Haven
$515,000
3 Beds ⋅ 2 Baths ⋅ Harbour Estates SubDv. ⋅ 33884 Zip Code
Located in the desirable, tree-lined community of Harbour Estates, this custom-built 3-bedroom, 2-bath pool home offers expansive living spaces, and an exceptional outdoor lifestyle. Situated on an impressive .57-acre corner lot at the end of a quiet cul-de-sac, this property provides privacy, space and convenience in a highly sought-after location. Upon arrival, a grand courtyard welcomes you to sit and enjoy the beautifully landscaped grounds. A lovely leaded-glass front door with transom window opens into the inviting foyer, creating an elegant first impression. The generously sized Living Room features a striking stone fireplace, tray ceiling and strategically placed floor outlets that allow for flexible furniture placement. Three sets of glass sliding doors overlook the patio and pool area, bringing the outdoors in and creating a seamless connection between the interior and exterior living spaces. The eat-in Kitchen showcases a timeless black-and-white design, featuring crisp white cabinetry accented with crown molding and designer brushed-nickel hardware. Sleek black granite countertops beautifully complement the tile backsplash, while the kitchen sink is strategically positioned beneath a picture-frame window offering wonderful views of the pool. The upgraded stainless-steel appliance package includes a convection range, while recessed lighting illuminates the space. A cabinet pantry provides additional storage and a convenient coffee bar with a USB outlet adds both functionality and convenience to the kitchen. The charming breakfast nook provides the perfect spot for casual dining. The formal Dining Room features classic chair-rail molding and flows effortlessly into the kitchen, making it ideal for entertaining. The spacious 16' x 23' Primary Bedroom Suite features a beautiful coved ceiling and plenty of room for a comfortable sitting area. Additional features include wall-to-wall carpeting, a safe, and 2 closets, one of which is a walk-in closet. The luxurious Primary Bath offers dual comfort-height vanities with granite countertops, linen closet and walk-in shower with glass enclosure. A bidet and comfort-height toilet are located within the private water closet. A convenient access door leads directly to the patio. Two spacious Guest Bedrooms share a lavishly appointed Guest Bathroom featuring an oversized vanity, luxurious soaking tub accented by a decorative tile surround and a separate walk-in shower with glass enclosure. Outdoor living is truly exceptional in the fully fenced and meticulously landscaped backyard. A sparkling saltwater pool, surrounded by an expansive patio, provides the perfect setting for relaxing or entertaining family and friends. Distant views of Little Lake Eloise add to the tranquil setting. Additional features include a Laundry Room w/ cabinetry, washer & dryer, double-pane Pella fiberglass windows, glass storm door, water softener system, 2024 water heater, security system, stone-accent facade, 2023 architectural shingle roof, well for irrigation, freshly painted exterior, gutters, exterior lights, & 220-volt wiring in the oversized 3 car garage. The garage also features a garage door opener & provides abundant space for vehicles, storage or recreational equipment. Ideally situated in the picturesque community of Harbour Estates, this exceptional home offers the perfect blend of space, comfort, privacy, and convenience, just minutes from shopping, restaurants and LEGOLAND Resort.

37 Lake Eloise Lane, Winter Haven
1215 Fairlane Court Nw, Winter Haven
$335,000
3 Beds ⋅ 2 Baths ⋅ 33881 Zip Code
Come take a look at this beautifully maintained 3-bedroom, 2-bath home near the heart of Winter Haven, ready for its new owners! This property offers an optional HOA with no deed restrictions, giving you added flexibility. Step inside to a spacious, open dining and kitchen area featuring updated appliances and plenty of room for entertaining. Toward the rear of the home, you'll find a HUGE living space that offers plenty of room for the whole family to relax and gather. Situated on a DOUBLE LOT totaling nearly half an acre, this property provides an abundance of outdoor space, with plenty of room to add a pool in the future. The fully fenced yard offers privacy and a safe space for pets, while the large storage shed provides plenty of room for tools, equipment, and all your extras. The home is situated on a dead end road for added privacy and no through traffic. Major updates include a roof replaced in 2018 and a completely replaced AC system in 2023. Located in a quiet neighborhood, this home offers a peaceful setting while still being conveniently close to shopping, medical facilities, dining, and entertainment. Come see all this lovely home has to provide and make it yours today!

1215 Fairlane Court Nw, Winter Haven
815 Lake Jessie Drive, Winter Haven
$595,000
4 Beds ⋅ 4 Baths ⋅ East View Pkwy SubDv. ⋅ 33881 Zip Code
Virtually Staged. Mediterranean-Style Estate with Private Casita, Pool, Covered 2-Car Garage, Spacious Workshop & NO HOA in Winter Haven. Welcome to a truly unique Mediterranean-style estate offering over 4,100 square feet of living space, exceptional versatility, and the freedom of no HOA. This spacious property features a main residence plus a private casita, creating an ideal setup for multi-generational living, extended family, guests, a private home office, or flexible additional living space. Inside, you'll find generous living areas, beautiful architectural details, and plenty of room for both everyday living and entertaining. Recent improvements include a NEW ROOF and NEW AC, offering added peace of mind for the next owner. Enjoy your own private outdoor oasis featuring a beautiful saltwater pool with a new heating and cooling system, complemented by a poolside cabana, perfect for relaxing and entertaining year-round. The property also features a covered 2-car garage and an ample workshop, providing excellent space for vehicles, hobbies, projects, tools, storage, or recreational equipment. Need even more room for your toys? With no HOA and ample parking for boats, RVs, and recreational vehicles, this property offers the space, flexibility, and freedom that can be difficult to find. Conveniently located near Winter Haven's famous Chain of Lakes, you'll be close to boating, fishing, recreation, shopping, dining, and everything the area has to offer. Whether you're searching for a family estate, multi-generational home, private guest accommodations, a home with income potential, or simply a distinctive property with plenty of space and privacy, this home offers endless possibilities. Can't tour in person? Virtual tours are also available! Contact us today to schedule your private showing or virtual tour and experience everything this exceptional Winter Haven property has to offer.

815 Lake Jessie Drive, Winter Haven
6283 Red Herring Drive, Winter Haven
$275,000
3 Beds ⋅ 2 Baths ⋅ Lakeside Landings Ph 01 SubDv. ⋅ 33881 Zip Code
Welcome to 6283 Red Herring Dr., a spacious 3-bedroom, 2-bath home offering 2,272 square feet of comfortable living space in a convenient Winter Haven location. The home features a two-car garage, fully fenced yard, and a screened-in covered back porch, creating the perfect space to relax or enjoy Florida living year-round. Inside, you’ll appreciate the carpet-free flooring throughout, a functional and inviting layout, and a kitchen with space for casual dining or a breakfast area. With generous living spaces, a private backyard, and a well-designed floor plan, this home offers the comfort, space, and versatility to fit a variety of lifestyles.

6283 Red Herring Drive, Winter Haven
4028 Phoenician Way, Winter Haven
$330,000
2 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code
CDD DEBT BALANCE PAID IN FULL*** DESIGNATED GOLF CART ENTRY/GARAGE (9x18) *** FLORIDA ROOM (10X30) ** EXTENDED SCREENED ENCLOSURE(15x30) ** ROOF REPLACED 2022** **Three (3) Windows Replaced in 2023** ** EXTERIOR OF THE HOME PAINTED IN 2021*** and DEDICATED UNSCREENED PAVER AREA FOR YOUR GRILL. This Bali Floor Plan with 2 Beds/2 Baths offers 1,484 sq.ft. living area PLUS 300 Sq. ft. living area in the Florida Room with Tile Floor and Air Conditioning. Grab your Binoculars- You're going to enjoy the nature views of the pond, golf course and wooded area while you relax on the back lanai. The Double Glass Door Entry opens into the heart of the home, the Living Room area. The Guest Bedroom and Bathroom are on the Right, Front of the Home. The Guest Bath features a Shower/Tub Combo and a pocket door provides privacy for overnight guests. A dedicated Linen Closet is in the hallway that leads to the Guest Bedroom/Bath. The Kitchen offers 42" cabinets, granite countertops, breakfast bar, reach in pantry and dinette area. The Living Room, Kitchen and Dinette areas have Crown molding and Tile Floors. The triple sliding glass door system in the Living Room and Double sliding glass door system in the Dinette create a wide, unobstructed opening to the Florida room, offering flexible ventilation, abundant natural light, and a seamless connection. The Florida Room could be used as a Craft area, additional Sitting area with TV or even a Bedroom room for Guests. You have Options! Make the Most of the Space!!! The Primary Suite offers His/Her Walk in Closets and En-suite with Tiled Shower, Vanity with Dual Integrated Sinks and Linen Closet. This attractive home has a 2 Car Garage (19x20) and Separate Golf Cart Garage. The Garage Doors have glass inserts for additional light into the garage and add to the Curb Value of this Home with Paver Driveway and Flagpole. The well-maintained lawn has an irrigation system and custom curbing outlines the landscape beds with rock mulch. Lake Ashton is a 55+ community with Resort Style Amenities, Planned Activities like Dances, Trivia, Day trips, Entertainment series, Holiday Events and MORE! The residents in Lake Ashton enjoy Outdoor and Indoor Swimming Pools, 2- Golf Courses (Memberships are Optional), 2 - Clubhouses, Pickleball, Tennis, Racquetball (Indoor), 1/2 Court Basketball (Indoor), Billiards, Bowling Lanes, Movie Theater, Eagles Nest (Eatery) and More. Make plans today to visit this home and Lake Ashton!

4028 Phoenician Way, Winter Haven
4064 Phoenician Way, Winter Haven
$449,900
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code
GOLF COURSE LIVING AT ITS FINEST! Take a look at this absolutely stunning 3 BR + Den / 2 BA St. John floor plan home in the highly desirable Lake Ashton community, a gated 55+ community in Central Florida! Located on an oversized corner lot, with NO BACKYARD NEIGHBORS you’ll enjoy the serene water views that border Hole 13 along Lake Ashton's West Course. This home has mature and well-maintained landscape with Oak Trees and Beautiful Stately Palm trees, all "watered" by a separate irrigation meter. Highlights you'll love about this home: Double French door entry with Custom Tilework & Interior Finishes in the Open and Spacious Living Room with Tray Ceiling, Triple Sliders that separate the Living Room from the Large Screened Lanai; Luxury Kitchen with Granite Countertops, Tile Backsplash, Under and Above Cabinet Lighting, Custom 42" Maple Cabinets with Pullouts, Pendant Lighting on the Breakfast Bar, SS Appliances, Crown Molding, Glass Front on Select Upper Cabinets and a New Wine Fridge. The Walk in Pantry and Dinette Areas are adjacent to the Kitchen. This home features a Luxurious Primary Suite with Trey Ceiling, His/Her Walk-in closets, a Private En-Suite bathroom complete with a Soaking tub, Separate shower with Custom tile and glass enclosure, Separate His/Her Vanities, and a Dedicated Linen closet. The Primary Suite is a serene retreat after a fun day in Lake Ashton. Additional Upgrades Include: Tile on the Diagonal Flooring, Custom Ceiling fans, Designer lighting fixtures, Stately columns at the entry and a formal dining area, Central Vac, Whole House Sound System and Plantation Shutters. Improvements to the home include: New Roof (2025), New Exterior Paint (2025), Coil Replacement on the A/C, New Water Heater (2025). This home is a Split Floor Plan, offering Privacy for the Owner and Overnight Guests. Bedroom 2 and Bedroom 3 have carpet flooring, a Built in Closet, and ceiling fan. Guests will enjoy the spacious Bath with Comfort Height Vanity and Glass Enclosed Shower. Enjoy Reading a Good Book? Escape to the Den- It's a cozy sitting area and has custom Built-In Shelving- the perfect place to display photos, books or your special "Collectibles. The inside laundry room in this home is sizeable and is the passage from the garage into the home. This home offers a 2- Car Garage and Dedicated Golf Cart Entry. Lake Ashton offers Planned Activities like Dances, Entertainment Series, Karaoke, Bingo and Trivia, Day Trips and SO MUCH MORE! Lake Ashton has two Clubhouses. Residents enjoy Indoor/Outdoor Pools, Pickleball Courts, Tennis Courts, 2- 18 Hole Golf Courses (Memberships Optional), Indoor Racquetball, Movie Theater, Bowling Lane, Fitness Centers (2), Eagles Nest (Eatery), Card, Craft and Billiards and MORE! Schedule an Appointment Today!

4064 Phoenician Way, Winter Haven
1631 Linz Court, Winter Haven
$190,500
2 Beds ⋅ 2 Baths ⋅ Vienna Square Ph 2b SubDv. ⋅ 33884 Zip Code
Maintenance-free Villa in the 55+ gated community of Vienna Square, centrally located in Winter Haven! A brick-paver driveway and walkway lead through mature landscaping to the covered front porch. Inside, the open floor plan features high ceilings, a spacious great room, and a split-bedroom layout. The primary suite offers a large bedroom and en-suite bath, while the second bedroom is conveniently located near the guest bath. The kitchen features a breakfast bar, ample cabinet and counter space, and all appliances, overlooking the Great Room living/dining area with access to the screened lanai through triple Sliding Glass Door. Low monthly HOA fees include roof replacement, exterior painting, lawn maintenance, irrigation, internet/cable TV, and community amenities. Residents enjoy a pool, hot tub, fitness center, tennis/pickleball, billiards, movie room, craft room, recreation room, and more. Conveniently located near shopping, dining, golf, fishing, boating, medical facilities, entertainment, Legoland, Disney, Universal, and both Tampa and Orlando International airports. Vienna Square offers active adult living with the ease, convenience, and peace of mind of low-maintenance living. This is a VA Foreclosure.

1631 Linz Court, Winter Haven
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