Winter Haven Homes with Rain Gutters Exterior Features

Winter Haven Homes with Rain Gutters Exterior Features

Welcome to Winter Haven, Florida—a charming city nestled in the heart of Polk County, renowned for its picturesque lakes and vibrant community. With its warm climate, friendly atmosphere, and a plethora of recreational activities, Winter Haven is an ideal place for families, retirees, and anyone looking to embrace the beauty of Florida living.

Known as the "Chain of Lakes City," Winter Haven boasts over 50 sparkling lakes, perfect for boating, fishing, and enjoying breathtaking sunsets. The city is rich in history and culture, offering a variety of local attractions, including the famous LEGOLAND Florida Resort, which draws visitors from near and far. With a thriving downtown area filled with delightful boutiques, cafes, and parks, Winter Haven provides a blend of small-town charm and modern amenities.

When it comes to real estate, Winter Haven offers a diverse selection of homes that cater to various lifestyles and budgets. One standout feature of many properties in this area is the inclusion of rain gutters, an essential exterior feature designed to protect your home from water damage. Rain gutters effectively channel rainwater away from your roof and foundation, helping to prevent erosion and leaks while maintaining the integrity of your property.

Whether you are looking for a cozy single-family home or a spacious waterfront property, Winter Haven has something to offer everyone. Discover the joys of living in this vibrant city, where community spirit and natural beauty come together to create the perfect Florida lifestyle. Explore your dream home today and experience all that Winter Haven has to offer!

Newest Winter Haven Homes with Rain Gutters Exterior Features

$139,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Walk right into this beautiful home located in Oakwood Estates, a 55+ community. You will find the home nicely furnished which all conveys with the sale of the home. The open living area at the front of the home has a beautiful lake view. The kitchen is open to another living space or dining area. The primary bedroom at the rear of the home is nice sized and will accommodate a king sized bed. The guest bedroom is attached to the guest bathroom offering privacy and convenience to your guests. The Lanai which is also air conditioned (vent behind the couch) offers a wonderful area to sit and enjoy your morning coffee where you can watch the world go by. Oakwood Estates offers many activities and amenities including two pools, two clubhouses, tennis courts, shuffle board, miniature golf and much more. You can stay as busy as you like or just sit back and enjoy the peaceful community. The golf cart is included in the sale of the home. The Sellers have a home warranty in place and with a reasonable offer will pay for three month to continue the plan. Make your appointment today to see this beautiful home.

4234 Rolling Oaks Drive, Winter Haven
$749,000
3 Beds ⋅ 4 Baths ⋅ Cypresswood Palma Ceia SubDv. ⋅ 33884 Zip Code
Meticulously maintained and beautifully remodeled, this exceptional Palma Ceia residence in Cypresswood offers pond frontage, three private en-suite bedrooms, a dedicated office, a heated swimming pool, and incredible golf course views. The pavered driveway and walkways, manicured flower gardens, and a 2022 black metal roof set the stage for the impressive interior. Elevated ceilings, crown molding, waterproof Pergo flooring, stone counters, and plantation shutters are just a few of the home’s stunning features. At the heart of the home is a spacious great room featuring a natural gas fireplace with shiplap façade. Triple sliding glass doors, with new screens, create a seamless indoor-outdoor flow to the covered lanai and pool area while showcasing the outdoor views. The updated kitchen features quartz counters, an island with a prep sink and filtered water, a Kohler workstation sink, breakfast bar, stainless appliances, double ovens, gas range, Bosch dishwasher, and a spacious dinette overlooking the pool. A private office provides the perfect setting for working from home. Designed to give everyone their own space, the home offers three bedrooms with en-suite bathrooms. The primary suite includes pool access, a tray ceiling, two walk-in closets with built-in shelving, and a gorgeous remodeled bathroom featuring a six-foot freestanding soaking tub, glass-enclosed walk-in shower, dual vanities, and a water closet. The second bedroom includes an equally impressive en-suite bath with custom tile flooring, a granite counter, tub, and separate walk-in shower. Located at the rear of the home, the third en-suite bedroom is ideal for visiting guests and can be closed off with a pocket door for added privacy. Its bathroom offers a granite counter with dual sinks, a tub and shower combo, and a linen closet. An additional linen closet is located in the guest-wing hallway. The interior laundry room provides a closet pantry, storage closet, and convenient half bathroom. Florida living takes center stage outdoors with a screen-enclosed heated pool, expansive covered lanai, and a separate screened area for sunning. The peaceful setting overlooks the pond and third hole of the golf course, where a variety of birds and wildlife can be enjoyed daily. Meticulously designed gardens, window planter boxes and a pavered sitting area near the pond—ideal for a fire pit—complete this private outdoor oasis. The two-car garage features an epoxy floor, utility sink, storage closets, and overhead storage racks. Additional improvements and features include a 2026 installed gas water heater, a 26-gauge standing seam metal roof (2022) with a 40-year warranty, dual-zone air conditioning (2020), irrigation on separate meter, plantation shutters throughout, remote-controlled lanai lighting, pool safety fence, Ring cameras, rain gutters, and more. Located within the guarded Cypresswood community, this remarkable home combines thoughtful updates, exceptional care, abundant privacy, and a truly beautiful golf course and waterfront setting. Cypresswood Golf & Country Club features an 18-hole championship golf course, driving range, pro shop, jr. olympic pool, tennis & pickleball courts, an event venue, a sports pub and more. Located just minutes from shopping, medical facilities and downtown Winter Haven. Centrally located between Tampa and Orlando with easy commutes to airports and beaches. Come see what this magnificent home and community in Central FL has to offer!

4040 Palma Ceia Circle, Winter Haven
$125,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
A Home That's Ready When You Are — Oakwood Estates, Winter Haven Some of life's best decisions are also the simplest ones. This lovingly maintained, fully furnished manufactured home in Oakwood Estates invites you to skip the hassle and step straight into the lifestyle you've been looking forward to — because everything has already been taken care of, and everything stays. Fresh interiors, thoughtful updates, and a warm, welcoming layout make this one of the most effortless purchases you'll make. Step inside and you're immediately greeted by natural light pouring through double-pane windows, setting a bright, airy tone throughout. The kitchen shines with stainless steel appliances, wood-look countertops, a newer sink, and crisp white cabinetry — and yes, everything stays, right down to the air fryer. The dining area features beautiful built-in cabinetry and shelving, flowing seamlessly into a spacious living room complete with an electric reclining sofa, flat screen TV, and comfortable seating. Luxury vinyl plank flooring runs throughout, tying it all together with style and ease of maintenance. Both bedrooms are generously sized and fully furnished. The primary suite features a walk-in closet, electric reclining bed, and a quality foam mattress. The Florida room offers updated ceiling fans, a brand-new AC unit, and convenient access to the in-home washer and dryer hookups — a true bonus in this community. Slide open the door to the enclosed lanai and enjoy your morning coffee overlooking lush, manicured landscaping — your own quiet corner of Florida. Additional highlights include hurricane shutters, vinyl siding, a 2017 roof, an irrigation system, and an updated electrical panel for peace of mind. Then there's the community. Oakwood Estates is a gated, beautifully maintained 55+ resident-owned community in the heart of Winter Haven — one of Polk County's most desirable areas. Residents enjoy two heated pools, two clubhouses, tennis and pickleball courts, shuffleboard, bocce ball, a miniature golf course, horseshoes, a fishing lake with pier, RV and boat storage, a library and activities center, pool tables, and a vibrant, active activities committee that keeps the social calendar full year-round. Lighted streets, underground utilities, and security cameras throughout the common areas reflect a community that takes pride in where it lives. This is Florida living, fully loaded and ready to go.

4332 Cherrywood Street, Winter Haven
$115,000
2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code
Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 1368 Square ft. 2 bedroom 2 bath 1984 with an attached enclosed Florida room and an enclosed carport with ac. The king size master bedroom has a walk-in closet and a private bathroom with a tub shower. It has an inside utility room with washer & dryer. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is fully furnished and ready to move in. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. Come see it today. This one won't last long. All measurements are approximate and should be verified by the buyer.

113 Lake Hazel Drive, Winter Haven
$379,900
5 Beds ⋅ 3 Baths ⋅ Inman Groves SubDv. ⋅ 33881 Zip Code
Welcome home to this beautifully maintained 5-bedroom, 3-bath residence offering nearly 2,700 square feet of flexible living space in one of Winter Haven's fastest-growing areas. Priced at just $379,900, this spacious home delivers exceptional value with room for everyone. Designed with today's lifestyles in mind, the thoughtfully crafted floor plan includes five true bedrooms, three full bathrooms, and a versatile flex room that can easily serve as a home office, playroom, media room, gym, or even a sixth bedroom. A first-floor guest suite provides the perfect setup for visitors, extended family, or multigenerational living. The heart of the home features an open-concept kitchen complete with granite countertops, abundant cabinet space, and plenty of room for gathering with family and friends. Durable tile flooring throughout the main living areas adds both style and easy maintenance, while the home's immaculate condition means you can move right in and start enjoying it from day one. Step outside to enjoy one of this home's standout features—no rear neighbors. Whether you're sipping your morning coffee or relaxing after a long day, you'll appreciate the added privacy and peaceful backdrop. Conveniently located just minutes from downtown Winter Haven, you'll enjoy easy access to local restaurants, boutique shopping, the historic Ritz Theatre, Saturday farmers markets, the public library, and the Chain of Lakes lifestyle that makes Winter Haven so special. A brand-new Publix is under construction just a short distance away, making everyday errands even more convenient. The community offers a low HOA with no CDD fees, helping keep monthly ownership costs affordable. You'll also be just minutes from Legoland Florida Resort and approximately 30 minutes from Walt Disney World, making this an ideal location for both everyday living and entertaining visiting family and friends. If you've been searching for a home that combines generous living space, a flexible floor plan, modern finishes, and an unbeatable Central Florida location, 204 Inman Boulevard is ready to welcome you home.

204 Inman Boulevard, Winter Haven
$110,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Move right into this furnished home located in Oakwood Estates, a 55+ community. The carpet throughout the home is in excellent condition. The rooms are very spacious and inviting. The home has been very well maintained. The dishwasher was installed in 2018, the washer and dryer 2020, and the refrigerator in 2024. Enjoy the bonus room on the front of the home or sit and watch the world go by on the comfortable lanai. Oakwood Estates offers many activities and amenities. If you are looking for exercise, you can join in with the pool or indoor aerobics. Chair Yoga is offered twice a week, or play some pool volleyball. The tennis court has recently been refinished and there is a pickle ball group that meets three times a week. During the winter months, there are several exciting dances as well as many activities. If food is your thing, Oakwood offers potluck dinners, ice cream socials, and weekly coffee and donuts. If you are looking for full time or just part time, this is your opportunity to move into a wonderful community, conveniently priced.

4807 Plumwood Street, Winter Haven
$305,000
3 Beds ⋅ 2 Baths ⋅ Waterside Village SubDv. ⋅ 33880 Zip Code
Virtually Staged. Welcome to Waterside Village, a community of just 48 homes that offers a peaceful setting while keeping you close to everything Winter Haven has. This move-in ready 3-bedroom, 2-bath home offers an open floor plan, spacious kitchen with a large walk-in pantry, and a backyard designed for entertaining. Enjoy the screened-in lanai, pool deck, and above-ground pool with a recently replaced liner, all within a fully fenced yard complete with a storage shed. Conveniently located near shopping, restaurants, grocery stores, and LEGOLAND, you'll love having everything you need just minutes away.

144 Waterside Circle, Winter Haven
$245,000
3 Beds ⋅ 2 Baths ⋅ Normandy Heights SubDv. ⋅ 33880 Zip Code
Welcome to a home that perfectly combines comfort, convenience, and value in one of Winter Haven's most desirable locations. Situated just minutes from the Polk Parkway, this property offers an easy commute to both Tampa and Orlando while keeping you close to everything Central Florida has to offer, including the renowned Chain of Lakes, world-class theme parks, shopping, dining, and everyday conveniences. Inside, you'll find a thoughtfully designed split bedroom floor plan featuring 3 bedrooms and 2 bathrooms, providing privacy for the primary suite while maintaining an open, functional layout. Vaulted ceilings and abundant natural light create a bright, spacious feel throughout the living areas, making the home feel warm and inviting from the moment you step inside. The kitchen is equipped with upgraded appliances and opens seamlessly to the main living spaces, making it ideal for both everyday living and entertaining. Ample closet space throughout the home provides plenty of storage, while the large fenced backyard offers room for pets, play, gardening, or simply relaxing outdoors. Recent improvements provide added peace of mind, including a brand new roof installed in 2025 and fresh exterior paint that enhances the home's curb appeal. Whether you're a first-time homebuyer, growing family, or someone looking to enjoy the convenience of Central Florida living, this move-in ready home delivers the perfect balance of location, functionality, and modern updates. Schedule your private showing today and discover everything this Winter Haven gem has to offer.

1320 Normandy Heights Circle, Winter Haven
$269,900
3 Beds ⋅ 2 Baths ⋅ Fla Highlands Co Sub SubDv. ⋅ 33884 Zip Code
Welcome to 118 Browning Circle, Winter Haven, FL, where comfort, thoughtful updates, and an unbeatable location come together to create the perfect place to call home. Nestled in a well-established neighborhood with no HOA, this beautifully maintained 3-bedroom, 2-bath home is truly move-in ready and offers the ideal blend of functionality and charm. Step inside to a spacious, open great room with attractive luxury vinyl flooring, creating a warm and inviting space for everyday living, family gatherings, or entertaining guests. The desirable split-bedroom floor plan provides added privacy, while the versatile third bedroom with built-in shelving makes an excellent home office, craft room, or guest bedroom. The kitchen offers abundant cabinet and counter space, a convenient pass-through window, and a cozy breakfast area, making meal preparation both practical and enjoyable. Just beyond, you'll fall in love with the expansive Florida Room, providing additional living space perfect for relaxing, entertaining, a game room, or simply enjoying Florida living year-round. The spacious primary suite features a private en-suite bathroom with a walk-in shower, while the indoor laundry room offers exceptional storage with multiple closets to help keep everything organized. Outside, the fully vinyl-fenced backyard creates your own private retreat. Enjoy beautiful mature landscaping, and a brick paver patio that's perfect for morning coffee, weekend barbecues, or quiet evenings outdoors. This home has been meticulously maintained and thoughtfully updated, giving buyers peace of mind for years to come, including: HVAC (2024), vinyl privacy fence (2024), attic insulation (2024), house replumbed (2022), brick paver patio (2023) Additional features include a spacious two-car garage with built-in shelving for extra storage and organization. Location is everything, and this home delivers. Just two blocks away, you'll enjoy access to the neighborhood park featuring a basketball court, playground, fishing pier, and community boat ramp. Plus, you're only minutes from LEGOLAND Florida Resort, shopping, restaurants, schools, medical facilities, and major roadways, making everyday convenience part of your lifestyle. If you've been searching for a home that offers space, updates, privacy, and an exceptional location, 118 Browning Circle is one you won't want to miss. Schedule your private showing today before it's gone!

118 Browning Circle, Winter Haven
$249,900
3 Beds ⋅ 2 Baths ⋅ Lucerne Park Reserve SubDv. ⋅ 33881 Zip Code
Welcome to 297 Meadowbrook Boulevard, a well-maintained 3-bedroom, 2-bathroom home located in the Lucerne Park Reserve community of Winter Haven. Built in 2020, this single-story residence offers approximately 1,408 square feet of comfortable living space with a functional, open-concept floor plan designed for everyday living and entertaining. The kitchen flows seamlessly into the main living and dining areas, creating an inviting central gathering space. The primary suite features a private bathroom and generous closet space, while two additional bedrooms provide flexibility for guests, a home office, hobbies, or additional living needs. A two-car attached garage offers convenient parking and storage. Residents can enjoy access to community amenities, including a swimming pool and playground. Conveniently situated near shopping, dining, schools, recreation, and major roadways, this property provides easy access to Winter Haven and the surrounding Central Florida area. Schedule your private showing today and explore everything this home has to provide!

297 Meadowbrook Boulevard, Winter Haven
$259,000
3 Beds ⋅ 2 Baths ⋅ Kensington View SubDv. ⋅ 33880 Zip Code
Fresh Updates & Move-In Ready! Welcome home to 392 Kensington View Drive! This beautifully refreshed 3-bedroom, 2-bath home offers the perfect blend of comfort, style, and functionality. The open-concept floor plan creates a bright, inviting living space that's ideal for both everyday living and entertaining. Enjoy the fresh feel of new interior and exterior paint, making this home truly move-in ready. Step outside to the spacious lanai, perfect for relaxing with your morning coffee or hosting family and friends. The new vinyl privacy fence provides a secure, private backyard for pets, play, or peaceful evenings outdoors. Additional features include an attached garage and a thoughtfully designed layout that maximizes space and natural light. Conveniently located near shopping, dining, schools, and major roadways, this home offers the perfect combination of comfort and convenience. Don't miss your opportunity to make this beautiful home yours—schedule your private showing today!

392 Kensington View Drive, Winter Haven
$409,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph I SubDv. ⋅ 33884 Zip Code
HOME FOR SALE IN LAKE ASHTON! Is 4052 Phoenician Way, Winter Haven, Florida YOUR next address? This 3 Bedroom, 2 Bath home with Golf Cart Entry is located on a large premium lot that abuts to the 13th Fairway of Lake Ashton's West Golf Course. The view from the wrap around covered and screened lanai includes a large pond that borders the 13th Hole with a farm pasture beyond. Home Highlights: CDD Debt Balance Paid in Full; Roof Replaced 2022; Water Heater Replaced 2022; A/C Heat Pump Replaced 2019. This home offers excellent curb appeal with a Widened Drive Way, Poured Curbing, Well Maintained Mature Landscape with Landscape Rock, Quoined Corners, Bay Window on the Front Bedroom, and arched Screened Entry. A paver walkway on the right side of the home connects the access door of the golf cart garage to the rear lanai. The interior of this home is warm and inviting with an Open and Spacious Living area. The Foyer, Dining, LR and Kitchen flow seamlessly together making entertaining a "breeze" in this home. The beautiful Bruce interlocking Engineered natural oak floors and the Plantation Shutters on the Side Lights of the Front Entry Door, Double Sliding Glass Doors in the Living Room, Bedroom 2 and Primary Bedroom accent the interior of this home- adding a touch of class. Crown molding gives definition to the Open Living area. The kitchen upgrades include: Granite counter tops, Maple Cabinets with raised panels, 3 banks of drawers, crown molding and a pantry. The refrigerator, microwave and disposal were replaced in 2026 and the range was replaced in 2023. A breakfast bar/snack bar and Dining areas are perfect for entertaining friends and family. Enter thru the 8' Front entry door with Eyebrow window above. To the left of the foyer are Bedrooms 2 and 3, a Linen Closet in the Hallway and a Guest Bathroom with shower/tub combo, accent window and comfort height vanity. A pocket door provides privacy to the Guest Bedroom area. The EXTENDED Primary Suite is located on the back on the home. It's the perfect place to relax after a long day in the sun. The Primary Suite offers a spacious sitting area and En-Suite with His/Her Walk in Closets, His/Her Separate Vanities, a large corner Soaking tub, a separate water room with a walk in shower with glass doors and linen closet. The laundry room is easily accessible from the garage and kitchen. It has cabinets for storage, a wash tub and the washer/dryer will be included in the sale of the home. The double car garage has hang down storage racks, attic access, storage cabinets, and an access door to the outside. There is a motorized screen on the garage door and a separate entry for the golf cart. The outdoor living space is a destination location in this home. The view is peaceful and the space is cozy with paver floor, ceiling fans and TV hook up. Make an appointment to tour this home today! Lake Ashton is a gated and guarded Florida Active Community with resort style amenities (2 Clubhouses with Movie Theater, Restaurant, Outdoor/Indoor Pools, Fitness Centers and More! Residents enjoy activities like Karaoke, Trivia, Dances, Entertainment Series, Holiday Events and so much more. You can stay busy living the Florida Retirement Dream every single day. For those that love the game of golf, there are (2) 18-Hole Golf Courses, a Pro Shop, Driving Range, Putting Green and the Eagles Nest (Hole 19). Don't wait to tour this home; tour it today!

4052 Phoenician Way, Winter Haven
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