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503 William Avenue, Winter Haven
$269,900
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
$380,000
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
125 Whittier Lane, Winter Haven
$225,000
3 Beds ⋅ 2 Baths ⋅ Fla Highlands Co Sub SubDv. ⋅ 33884 Zip Code
Virtually Staged. NO HOA! 3BR/2BA Gem in Established quiet Winter Haven Neighborhood! Welcome home to this solid, beautifully built 3-bedroom, 2-bathroom residence featuring a 2-car garage and a spacious, comfortable layout designed for easy living! This property offers complete freedom and flexibility. Big-ticket updates provide complete peace of mind, including a roof replaced in 2020 and an HVAC system installed in 2019. Inside, enjoy an inviting floor plan with ample living space, ideal for relaxing or entertaining. Step outside to your private backyard—perfect for outdoor gatherings, pets, or creating your own backyard oasis. Conveniently located just minutes from top-rated schools, local shopping centers, medical facilities, dining, and popular area attractions. Whether you are searching for your ideal primary residence, a relaxing Florida vacation getaway, or a high-performing addition to your rental investment portfolio, this versatile home is an absolute must-see!

125 Whittier Lane, Winter Haven
240 Westwood Avenue, Winter Haven
$249,900
3 Beds ⋅ 2 Baths ⋅ Brysons R H Sub SubDv. ⋅ 33880 Zip Code
Completely remodeled, full of charm, and NO HOA! Welcome to this beautifully updated 3-bedroom, 2-bath home in Winter Haven, where modern finishes and comfortable living come together. Step inside to a bright, open floor plan featuring beautiful new-look flooring, fresh neutral tones, and an inviting living space that flows seamlessly into the kitchen and dining area. The beautifully remodeled kitchen offers shaker-style cabinetry, gorgeous countertops, stainless steel appliances, modern fixtures, and a spacious breakfast bar perfect for gathering with family and friends. Both bathrooms have been tastefully updated with stylish vanities, modern finishes, and beautiful tilework. A metal roof adds another appealing feature to this already impressive home. Outside, you'll find a spacious backyard with mature trees and plenty of room for entertaining, gardening, pets, or simply enjoying your own outdoor space. With NO HOA, you have the freedom to make this property your own! Conveniently located near shopping, dining, downtown Winter Haven, parks, and the area's beautiful lakes, with access to major roadways connecting you to Lakeland, I-4, Tampa, and Orlando. Beautifully updated, thoughtfully designed, and ready for you to move right in. Come see everything this Winter Haven home has to offer!

240 Westwood Avenue, Winter Haven
703 Avenue L Se, Winter Haven
$278,000
4 Beds ⋅ 2 Baths ⋅ Carls Sub SubDv. ⋅ 33880 Zip Code
Looking for a 4-bedroom home in Winter Haven with extra-living space and convenient access to shopping, dining, and local attractions? Located at 703 Avenue L SE, this single-family home offers 4 bedrooms, 2 full bathrooms, approximately 1,830 square feet of heated living space, and a separate flex room ideal for a home office, playroom, hobby room, or additional sitting area. The layout offers flexibility for everyday living, with a kitchen featuring granite countertops, stainless steel appliances, and cabinet storage. The primary suite includes an en-suite bathroom with a walk-in shower. Other features include porcelain tile flooring, double-pane windows, a one-car covered carport with storage space, and a fenced backyard with room for outdoor activities or gardening. Important updates documented in a February 2025 four-point inspection include a complete re-pipe with PEX plumbing in 2016 and a full architectural-shingle roof replacement in 2016. At the time of that inspection, the roof was rated satisfactory with an estimated 16 years of remaining useful life; this is an inspector’s estimate, not a warranty or guarantee.Enjoy convenient access to everyday essentials, including Publix at Southeast Plaza Shopping Center and Walmart Supercenter on Cypress Gardens Boulevard, along with nearby restaurants, shops, and services. Citrus Connection Route 30 serves the area, including a stop at 6th Street SE and Avenue K SE. Downtown Winter Haven adds local restaurants, coffee shops, boutiques, parks, and community events. For recreation, explore Winter Haven’s Chain of Lakes, nearby parks and trails, or LEGOLAND Florida Resort within driving distance. With four bedrooms, a versatile flex room, documented system updates, covered parking, and access to the shops and activities of Winter Haven, this home offers practical space in a convenient Central Florida location. Schedule a showing to see the layout and possibilities in person.

703 Avenue L Se, Winter Haven
420 Hillcrest Drive Se, Winter Haven
$279,900
3 Beds ⋅ 2 Baths ⋅ Eloise Woods Lake Roy Unit SubDv. ⋅ 33884 Zip Code
*** WELL CARED FOR WITH MANY RECENT UPDATES IN THIS 3 BED 2 BATH 2 CAR GARAGE *** FRESH PAINT INSIDE & OUT, ALL NEW FLOORING & BASEBOARDS, NEW KITCHEN WITH QUARTZ COUNTER TOPS & APPLIANCES. MASTER RETREAT IS SPACIOUS WITH PRIVATE FULL BATH *** COME CHECK THIS OUT TODAY ***

420 Hillcrest Drive Se, Winter Haven
1400 Avenue D Ne, Winter Haven
$337,500
3 Beds ⋅ 2 Baths ⋅ Lake Elbert Heights SubDv. ⋅ 33881 Zip Code
3 BR - 2BATH LAKEVIEW HOME WITH OVER 2000 SF OF LIVING AREA AND 2 CAR GARAGE, THIS PROPERTY ALSO INCLUDES A 40 FT WATERFRONT LOT WITH REBUILT DOCK W/COVERED BOAT DOCK ON LAKE ELBERT. THIS HOME IS CLEAN AND MOVE IN READY. FORMAL LIVING ROOM, FORMAL DINING ROOM, KITCHEN IS OPEN TO THE FAMILY ROOM WITH BRICK FIREPLACE. THE DINETTE OFF THE KITCHEN HAS ACCESS TO THE SCREEN ENCLOSED REAR PORCH WHICH ALSO HAS ACCESS FROM THE FORMAL DINING ROOM. THE FENCED BACK YARD HAS A NICE SHED AND BEAUTIFUL OAKS. THIS HOME HAS HAD SOME MODIFICATION SUCH AS THE MASTER SUITE HAS A LARGE OPEN LAUNDRY ROOM WITH WASHER & DRYER AND THE GUEST BATHROOM HAS A ROLL IN SHOWER ACCESS. HOME ALSO HAS A GENERATOR. YOU HAVE A VIEW OF LAKE ELBERT FROM YOUR FRONT YARD AND ALSO CAN WALK DOWN TO YOUR PRIVATE DOCK AND ENJOY THE BEAUTIFUL FLORIDA SUNSETS OR ENJOY A WALK AROUND LAKE ELBERT ON THE WALKING PATH. POLK STATE COLLEGE JUST ACROSS THE LAKE. THIS PROPERTY IS CONVENIENTLY LOCATED ONLY MINUTES TO DOWNTOWN WINTER HAVEN WITH RESTAURANT, SHOPPING, LIBRARY, PARK AND LOCAL EVENTS. DON'T FORGET THE FREE CYPRESS GARDENS SKI SHOW ON LAKE SILVER.

1400 Avenue D Ne, Winter Haven
650 9th Street Ne, Winter Haven
$179,900
2 Beds ⋅ 2 Baths ⋅ Jarvis Heights SubDv. ⋅ 33881 Zip Code
Lots of potential in this charming 2-bedroom, 2-bath home featuring a large kitchen with plenty of space for cooking and entertaining. The home has new flooring throughout giving the interior a fresh feel. This home has no HOA. Enjoy the outdoors in the large, fully fenched-in yard, perfect for pets, gardening, entertaining or relaxing with family and friends. Additional highlights include a metal roof installed in 2024 providing durability and peace of mind. This home is a great opportunity for homeowners or investors looking for a great space, convenience and potential.

650 9th Street Ne, Winter Haven
420 Avenue U Ne, Winter Haven
$155,900
3 Beds ⋅ 2 Baths ⋅ Eula Vista Sub SubDv. ⋅ 33881 Zip Code
Welcome to this charming 3-bedroom, 1.5 bathroom solid block home offering a comfortable 1,216 square feet of living space in an established, NO-HOA neighborhood. Built in 1960 and situated on a 0.14-acre lot, this property features a fully fenced front-to-back yard with a massive backyard and generous front yard. Step inside to enjoy a bright interior complemented by fresh paint, new flooring, spacious closets, convenient linen closets for extra storage, and a delightful enclosed Florida room with French doors. Major peace of mind comes with a brand-new roof installed in 2022. Perfectly positioned just minutes from local lakes, parks, recreation centers, magnet schools, and public transit, this home combines timeless character with modern updates. Schedule your showing today!

420 Avenue U Ne, Winter Haven
444 Avenue I Se, Winter Haven
$119,000
2 Beds ⋅ 2 Baths ⋅ Pine Crest Heights SubDv. ⋅ 33880 Zip Code
INVESTOR OPPORTUNITY with recent systems updates! The costly systems have been updated at this 2-bedroom, 2-bath home at 444 Avenue I SE in Winter Haven: Roof (2025), HVAC (2023), Water Heater (2023), and Plumbing (2023, all except the kitchen). The electrical wiring in the demoed bathroom was also updated in 2023. With these recent updates, more of your renovation budget can go toward finishes and value-adding improvements. Offering approximately 1,036 square feet of living space on a 75 x 140 lot in an established neighborhood close to downtown. Inside, hardwood floors, a wood-burning fireplace, and separate living and dining areas provide character and a solid starting point for your renovation plans. The spacious yard offers room to enjoy the outdoors, while a detached shed provides additional workshop and storage space. No HOA. Located approximately one mile from downtown Winter Haven, the home offers convenient access to Central Avenue's shopping and dining and the historic Ritz Theatre. Winter Haven Hospital and Polk State College's Winter Haven campus are also nearby. Enjoy the area's lakes and outdoor recreation, including South Lake Howard Nature Park, with additional shopping and dining along Cypress Gardens Boulevard and LEGOLAND Florida Resort within driving distance. The home requires repairs and renovation, and is being sold strictly AS-IS. CASH OR HARD MONEY FINANCING ONLY. An opportunity to bring new life to a property with updated systems, character, outdoor space, and proximity to Winter Haven's amenities. Seller makes no representations or warranties regarding condition, square footage, zoning, permitted uses, or future development potential. Buyer and buyer's agent are responsible for conducting their own due diligence. The roof has a hole and requires repairs.

444 Avenue I Se, Winter Haven
640 Avenue I Nw, Winter Haven
$325,000
3 Beds ⋅ 3 Baths ⋅ Villa Park Or Stone & Manns SubDv. ⋅ 33881 Zip Code
GREAT OPPORTUNITY to own this unique property. If you have a strong vision for remodeling and a passion for a project, this is the perfect property for you to restore to it's full potential! The main house and the duplex in the back of the property combine a total of over 3700 sq ft of living. The main house could be your residence while the duplex offers flexibility- ideal as an in-law suite, a rental income, or both. It could even be a place to live while you renovate the main house. The possibilities are endless with this fixer upper. The Location is OUSTANDING: walk to downtown, grocery stores, bus terminal, medical facilities, Hospital, restaurants, and shopping. With the RIGHT vision, this property can be used in a variety of ways and may even generate income to help cover the mortgage while using the main house as your primary residence. Please schedule your showing and contact your lender for information about a reno loan today so you don't miss the chance to own this property!

640 Avenue I Nw, Winter Haven
1020 W Lake Hamilton Drive, Winter Haven
$710,000
4 Beds ⋅ 3 Baths ⋅ Pollard Shores SubDv. ⋅ 33881 Zip Code
Central Florida Lakefront living in Winter Haven, Florida on an acre of land with no HOA. This home is for a buyer who loves lake views, great fishing, skiing and water sports. With over 3,400 square feet, this 4 bedroom 3 bathroom home is located just minutes from downtown, Lego Land and about an hour from Orlando attractions. Move-in ready for your family or start retirement at the lakefront retreat. Spend time in the 18 x 11 workshop or enjoy lounging in the recently added screened room while enjoying the lake views, wildlife and beautiful oaks.

1020 W Lake Hamilton Drive, Winter Haven
1075 8th Street Nw, Winter Haven
$480,000
4 Beds ⋅ 3 Baths ⋅ Haven Shores SubDv. ⋅ 33881 Zip Code
RENOVATED, SPACIOUS, AND JUST MINUTES FROM LAKE HOWARD! Discover this beautifully renovated 4-bedroom, 3-bathroom home in the heart of Winter Haven, offering a combination of modern upgrades, flexible living arrangements, and a fantastic location near the scenic Chain of Lakes! With 1,985 square feet of living space and 2,455 total square feet, including the garage and porch, this home is designed for comfortable and flexible living! Major improvements completed in 2021 include a NEW ROOF, IMPACT-RESISTANT WINDOWS AND DOORS, along with updates to the electrical, plumbing, and HVAC system. What truly sets this property apart is its VERSATILITY! The home features an IN-LAW SUITE, providing additional space for extended family, guests, or multigenerational living. Looking for even more flexibility? The primary bedroom offers potential for conversion into a private studio-style unit, creating the possibility of a SECOND IN-LAW SUITE! These possibilities make the property especially appealing to buyers seeking adaptable living arrangements. Step outside and enjoy your own backyard retreat featuring an ABOVE-GROUND POOL, perfect for Florida’s sunny days! An additional backyard structure also presents potential for a future accessory dwelling unit (ADU). LOCATION, LOCATION, LOCATION! Just minutes from beautiful Lake Howard, part of Winter Haven’s Chain of Lakes, and conveniently located near downtown Winter Haven, shopping, restaurants, and medical facilities. LEGOLAND Florida Resort is approximately 20 minutes away! With extensive renovations, multiple possibilities for flexible living space, and a convenient location, this is a property you won’t want to miss. Schedule your private showing today! Must have proof of funds for showings.

1075 8th Street Nw, Winter Haven
218 6th Jpv Street, Winter Haven
$255,000
3 Beds ⋅ 2 Baths ⋅ Jan Phyl Village Rep SubDv. ⋅ 33880 Zip Code
This 3-bedroom, 2-bath pool home with ease of access to the Polk Parkway is perfect for all needs. It features luxury vinyl planks flooring throughout, split bedrooms, granite countertops, stainless steel appliances, primary bedroom with wood burning fireplace, and inside laundry area. Outdoor step into a good-sized backyard that is fenced and features a swimming pool with a brand new pool pump. Other features include a pavered driveway, HVAC unit is 3 years old, and roof is approximately 6 years old. Call today, this one won't last long.

218 6th Jpv Street, Winter Haven
714 Avenue O Se, Winter Haven
$359,900
5 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv. ⋅ 33880 Zip Code
Welcome to 714 Avenue O SE! Situated in a prime SE Winter Haven neighborhood (Polk County), this fully modernized, single-story Mid-Century Ranch features 5 bedrooms, 2 bathrooms, and 2,104 sq ft of open living space. Constructed in 1964 on a 0.32-acre lot, shaded by mature Florida oak trees, the interior includes tile flooring, central air conditioning, a wood-burning fireplace, and an updated kitchen with stainless steel appliances and solid wood cabinetry. Highlights feature an attached car garage, tankless gas water heater, impact/double-pane windows, and an indoor laundry room. Step outside to your private oasis featuring a fully renovated in-ground pool, screened lanai, open patio, and brand-new privacy-fenced backyard. Conveniently zoned for Chain of Lakes Elementary and Winter Haven Senior High!

714 Avenue O Se, Winter Haven
828 30th Street Nw, Winter Haven
$215,000
3 Beds ⋅ 2 Baths ⋅ Westwood Sub SubDv. ⋅ 33881 Zip Code
MOVE-IN-READY 3-BEDROOM, 2-BATH HOME ON A 0.31-ACRE DOUBLE LOT WITH A 2026 ROOF, NEW SEPTIC SYSTEM, AND NO HOA IN WINTER HAVEN! Cosmetic updates include new flooring, fresh paint, refreshed bedrooms and bathrooms, and an updated kitchen with new cabinets, countertops, and appliances. Additional improvements include a water heater replaced within the last few years. The double lot offers plenty of outdoor space for gardening, entertaining, or enjoying the Florida sunshine. Located near Lake Howard, Lake Cannon, and Downtown Winter Haven’s dining, shopping, and entertainment, with access to the Chain of Lakes for boating, fishing, and waterfront recreation. Convenient access to US-17 and US-92 connects you to Auburndale, Lakeland, and surrounding Central Florida destinations. FHA, VA, conventional, USDA financing, and cash offers welcome. Square footage is owner provided. Buyer to verify square footage and all measurements. Schedule your showing today!

828 30th Street Nw, Winter Haven
104 13th Street Se, Winter Haven
$200,000
2 Beds ⋅ 2 Baths ⋅ Elbert Hills SubDv. ⋅ 33880 Zip Code
A great opportunity for a handyman or investor! This 2-bedroom, 2-bath home offers 1,776 square feet of living space, plus a versatile bonus room with a bathroom. Enjoy a spacious 15-by-24 foot screened back porch, and an above-ground pool, and a view of Lake Elbert from the front driveway. With a little TLC, this property is ready to make your own or unlock its investment potential in desirable area of Winter Haven.

104 13th Street Se, Winter Haven
842 Avenue N Sw, Winter Haven
$175,000
3 Beds ⋅ 1 Baths ⋅ Lake Shipp Or Porters Add SubDv. ⋅ 33880 Zip Code
Rental income from day one in Winter Haven! This 3 bedroom, 1 bath home near downtown has a tenant in place through September 30, 2027, paying $1,350 per month, giving an investor a predictable return from the day they close. Inside, you'll find an updated kitchen, central AC, and a fireplace that adds character to the main living area. Outside, the property sits on a quarter acre lot with a screened front patio, a backyard deck, and a large fenced backyard, which makes the home appealing to future tenants and a future owner-occupant alike. The location is close to downtown Winter Haven, with dining, shopping, and the area's lakes nearby. Lease and rent history are available on request. Showings are by appointment only - see remarks.

842 Avenue N Sw, Winter Haven
827 Avenue O Sw, Winter Haven
$229,900
3 Beds ⋅ 2 Baths ⋅ Lake Shipp Or Porters Add SubDv. ⋅ 33880 Zip Code
Welcome to this beautifully remodeled Winter Haven home with a desirable Lake Shipp view! Thoughtfully updated from top to bottom, this property offers the peace of mind of a new roof, new HVAC system, updated plumbing, and updated electrical—giving you the feel of a brand-new home without the new-construction wait. Inside, enjoy a fresh, modern living space with quality updates and an inviting layout designed for comfortable everyday living and entertaining. The Lake Shipp views add a special touch, creating a relaxing backdrop to your Florida lifestyle. With major systems already updated, this home is an excellent opportunity for buyers looking for a move-in-ready property with substantial improvements already completed. Conveniently located in Winter Haven with easy access to area shopping, dining, recreation, and Central Florida attractions.

827 Avenue O Sw, Winter Haven
624 Lake Elizabeth Drive, Winter Haven
$145,000
2 Beds ⋅ 1 Baths ⋅ Eloise Woods Lakes Miriam Un SubDv. ⋅ 33884 Zip Code
Under contract-accepting backup offers. Charming single-story bungalow nestled in the desirable Eloise Woods Lakes community. This inviting home offers two spacious bedrooms, a comfortable family room, separate living and dining areas, and a dedicated laundry room. The kitchen features rich-colored cabinetry, sleek stainless steel appliances, and plenty of charm. Enjoy the added living space of the screened-in sunroom overlooking a large, private backyard with mature landscaping—perfect for relaxing or entertaining. Ceiling fans throughout and a convenient single-car carport add to the home's comfort and functionality. Ideally located near shopping, dining, and everyday conveniences, this delightful home is ready to welcome you!

624 Lake Elizabeth Drive, Winter Haven
645 Avenue M Se, Winter Haven
$330,000
3 Beds ⋅ 2 Baths ⋅ Carls Sub SubDv. ⋅ 33880 Zip Code
LOOK AT THIS WELL-KEPT 3 BEDROOM, 2 BATH HOME WITH LOTS OF STORAGE, PRIVACY AND NO HOA!!! SOME NOTABLE UPDATES IN NEW ROOF- (2024), NEW AC- (2022), NEW WATER HEATER- (2020). You will absolutely love this spacious kitchen that has an abundance of SOLID WOOD CABINETRY and CORIAN COUNTERTOPS! The STAINLESS APPLIANCES- refrigerator, stove, dishwasher, and microwave were replaced in (2020). The dining and living room area boast LAMINATE FLOORING, RECESSED LIGHTING, VAULTED CEILING and a CUSTOM GRANITE BUFFET. The family room opens out to a large back porch that is perfect for all your "Game Day" entertaining! Don't forget about the CHEF'S DREAM OUTDOOR AREA featuring a Jenn-Air stainless gas grill, smoker, wok, and also an extra gas burner. This home has PLENTY OF STORAGE featuring 2 separate dedicated areas under AC perfect for a workshop/hobbies, or extra equipment storage. This home is conveniently located in Winter Haven, FL, home to LEGOLAND!!! Medical, shopping and restaurants are a very short distance from this very solid block/brick home.

645 Avenue M Se, Winter Haven
215 S Lake Howard Drive, Winter Haven
$419,000
3 Beds ⋅ 2 Baths ⋅ Linger & Nichols Sub/Winter H SubDv. ⋅ 33880 Zip Code
Under contract-accepting backup offers. LAKEFRONT OPPORTUNITY ON LAKE HOWARD! Enjoy the Winter Haven waterfront lifestyle at 215 S Lake Howard Drive. This 3-bedroom (with bonus room off bedroom- possibly and office overlooking the lake), 2-bath home includes lakefront property directly across Lake Howard Drive from the residence, providing access to beautiful Lake Howard along with a private dock and covered boat area. The home has recently been refreshed and is ready for its next chapter, featuring fresh interior paint, new carpet and padding, professional cleaning, and professionally steam-cleaned tile. The floor plan offers comfortable living spaces, a single-car garage, and a large screened rear patio overlooking the spacious, fenced backyard. Across the street, your lakefront area provides the opportunity to enjoy boating, fishing, and everything that makes living on Lake Howard so special. Keep your boat conveniently at the dock and head out on the water to enjoy the Central Florida lake lifestyle. The home offers a great foundation for a buyer looking for waterfront access while still having the opportunity to make additional improvements and personalize the property. With some added love and updating, this could become a wonderful full-time residence, seasonal Florida home, or lake retreat. Conveniently located near downtown Winter Haven, shopping, dining, medical facilities, and area attractions, this property combines an established location with one of Winter Haven's most desirable amenities—access to Lake Howard right across the street. Bring your vision, your boat, and your love of the water and discover the possibilities at 215 S Lake Howard Drive!

215 S Lake Howard Drive, Winter Haven
815 Lake Jessie Drive, Winter Haven
$595,000
4 Beds ⋅ 4 Baths ⋅ East View Pkwy SubDv. ⋅ 33881 Zip Code
Virtually Staged. $20,000 SELLER CREDIT! Take advantage of this amazing opportunity! The sellers are offering a $20,000 CREDIT that buyers can use toward closing costs, to buy down their mortgage interest rate, or a combination of both! 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
124 Edgewater Drive, Winter Haven
$239,999
3 Beds ⋅ 1 Baths ⋅ Carefree Cove SubDv. ⋅ 33881 Zip Code
MOTIVATED SELLER Welcome to this charming home tucked into the desirable Carefree Cove neighborhood of Winter Haven. This 3 bedroom, 1 bath home is as cute as a button and features a beautiful living space that has been thoughtfully remodeled throughout, offering move-in-ready comfort with none of the guesswork. The front exterior has custom woodwork making a modern statement as soon as you pull up. A long driveway can accommodate multiple vehicles or storage for a boat or RV. Upon stepping inside you'll find brand-new laminate flooring flowing throughout every room, making clean ups and pet care easy peasy as there is NO carpet anywhere in the home. An upfront drop-zone is perfect for slipping on your shoes or storing purses & backpacks. Love to entertain??? Then the large family room will check these boxes! With a beautiful fireplace as a focal point, you'll also have a cafe section perfect for popcorn & snacks with a beverage fridge tucked in the corner. Tons of windows throughout make this a bright and airy home. The kitchen has been upgraded to butcher block countertops that are stunning on the eyes. A large pantry can easily accommodate all the big cases of water, rolls of paper towel & much much more! Just off of the kitchen is a nicely sized dining room. This can hold a large formal table and still have room for a serving buffet or credenza for extra storage. All 3 bedrooms feature new closet sliding doors. Major system upgrades give buyers extra peace of mind, including a brand-new roof and a 4-year-old air conditioning system. The big-ticket items are already taken care of. This home sits on a generous 7,279 sq ft lot with a fully fenced rear yard and a bonus screened patio, perfect for enjoying Florida evenings. Fire up the grill and enjoy BBQing while cozying up to a fire-pit in your rear backyard oasis. Solid block construction and a slab foundation add to the home's durability. Ideally located just off Carefree Cove Drive near the water, this home offers a quiet, established neighborhood feel while remaining close to Winter Haven's shopping, dining, and the area's famous chain of lakes. Whether you're a first-time buyer, downsizer, or investor, this fully updated home is ready for its next chapter. Schedule your showing today!

124 Edgewater Drive, Winter Haven
1325 Lake Shipp Dr N, Winter Haven
$224,900
3 Beds ⋅ 1 Baths ⋅ 33880 Zip Code
Bring your vision and make this 3-bedroom, 1-bath home your own! This property needs some TLC but offers great potential, with several important updates already completed. Features include original hardwood floors, an inviting screened-in pool, and sliding glass doors that open directly to the pool area—perfect for enjoying Florida living. The home also offers a convenient inside laundry room complete with a washer and dryer and a spacious 25’ x 8’ enclosed front porch complete with ceiling fans, providing additional flexible living or entertaining space. Outside, you’ll find a large fenced yard with plenty of room to enjoy the outdoors. Major updates include a new roof in 2026, New pool pump in 2026, New gas water heater 2026, and updated windows and glass sliding doors. With the big-ticket items already addressed, this home is ready for someone to add their personal touches and bring out its full potential. The home also has a Brinks home security system. Don’t miss this opportunity to create your own Florida home with a pool and a large fenced yard!

1325 Lake Shipp Dr N, Winter Haven
1540 S Lake Shipp Drive, Winter Haven
$215,000
2 Beds ⋅ 1 Baths ⋅ Lake Shipp Heights SubDv. ⋅ 33880 Zip Code
Welcome home! If you’ve been looking for a home with a little more room to enjoy both inside and out, this 2-bedroom, 1-bath Winter Haven home may be just what you’ve been waiting for. As you step inside, you’re welcomed by a spacious living area with beautiful wood flooring and a brick fireplace that gives the room plenty of character. The kitchen features white cabinets, stainless steel appliances, plenty of counter space, and tile flooring. There’s also an additional enclosed space that gives you options—make it your home office, sitting area, playroom, or whatever works best for you. And wait until you see the outdoor space! Sitting on approximately 0.29 acres, the property is fully fenced with plenty of front yard and backyard space. Whether you enjoy entertaining, gardening, spending time outside with your pets, or simply want a little more room between you and your neighbors, there’s plenty of space to make it your own. You’ll also have a detached storage building for those extra items, an attached one-car garage, and a roof that is approximately 6 years old. And one more thing buyers will appreciate—NO HOA! Conveniently located in Winter Haven near shopping, dining, and everyday needs, this home gives you space, flexibility, and the freedom to make it your own. Come take a look and imagine yourself calling this one home. Schedule your private showing today!

1540 S Lake Shipp Drive, Winter Haven
716 Avenue I Ne, Winter Haven
$258,500
3 Beds ⋅ 2 Baths ⋅ Hutchinson Add SubDv. ⋅ 33881 Zip Code
Under contract-accepting backup offers. Virtually Staged. Welcome home to this beautifully maintained midcentury gem, tucked in the highly sought-after Lake Elbert Trail neighborhood! Set on a sprawling quarter-acre-plus lot, this move-in ready beauty blends timeless character with modern comfort — featuring a stylish updated kitchen with brand-new appliances and fresh new carpet in every bedroom. Major peace-of-mind updates already done for you: roof (2023), water heater (2025), plumbing (2024), and electrical (2026). Step outside to a sprawling front yard and a fully fenced backyard — plus a bonus storage barn for all your extras. Homes like this in Lake Elbert Trail don't last — schedule your showing today!

716 Avenue I Ne, Winter Haven
Winter Haven
$310,000
3 Beds ⋅ 2 Baths ⋅ Lake Elbert Estates SubDv. ⋅ 33881 Zip Code
Welcome to this beautifully remodeled 3-bedroom, 2-bathroom home offering approximately 1,220 square feet of living space on a generous 0.28-acre lot. The home features an updated interior, modern finishes, comfortable living areas, and a functional floor plan. Conveniently located near shopping, dining, recreation, and downtown Winter Haven. Schedule your private showing today and come see everything this move-in-ready home. Owner is willing to give $5000 towards closing costs.

Winter Haven
1210 32nd Street Nw, Winter Haven
$179,900
3 Beds ⋅ 1 Baths ⋅ West Cannon Heights SubDv. ⋅ 33881 Zip Code
Virtually Staged. Welcome to this 3-bedroom, 1-bath home in Winter Haven. The single-story home offers a comfortable layout with well-sized bedrooms and inviting living spaces. A one-car carport provides convenient covered parking, while the outdoor space offers room to enjoy the Florida weather. The home will benefit from some minor updates, providing an opportunity to add personal touches and make the property your own. Conveniently located near local schools, shopping, dining, parks, and major roadways.

1210 32nd Street Nw, Winter Haven
113 Avenue C Se, Winter Haven
$319,900
4 Beds ⋅ 2 Baths ⋅ Haven Terrace SubDv. ⋅ 33880 Zip Code
SINGLE-FAMILY HOME WITH DETACHED IN-LAW SUITE, RENTAL INCOME & NO HOA! This unique Winter Haven property features a 3-BEDROOM, 1-BATH MAIN HOME plus a separate 1-BEDROOM, 1-BATH DETACHED IN-LAW SUITE, ideal for MULTIGENERATIONAL LIVING, extended family, guests, or ADDITIONAL RENTAL INCOME. The main home is currently operated as a SHORT-TERM RENTAL and is being sold FULLY FURNISHED, with furniture included in the sale price, offering a TURNKEY opportunity for a new owner or a MOVE-IN-READY PRIMARY RESIDENCE. The detached suite has its own PRIVATE ENTRANCE, SEPARATE ADDRESS, PARKING, and SEPARATE UTILITIES currently paid by the tenant, and is generating $1,095/MONTH in rental income while maintaining privacy between both living spaces. Major improvements include NEWER ROOFS completed within approximately the last two years, UPDATED PLUMBING, and CENTRAL A/C for both living spaces. Located just minutes from DOWNTOWN WINTER HAVEN with convenient access to restaurants, shopping, entertainment, and the continued GROWTH AND DEVELOPMENT happening throughout the area. Live in the main home while collecting rental income, continue utilizing the main home as a SHORT-TERM RENTAL, or accommodate extended family—the property offers exceptional FLEXIBILITY for a variety of living arrangements and income opportunities, subject to applicable local regulations. NO HOA!

113 Avenue C Se, Winter Haven

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