Winter Haven FL Real Estate & Homes for Sale

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,313
Status:
NEW LISTING
MLS#:
P4939927
Type:
Single Family
Subdivision:
Cypress Landing Ph 01
Lot size:
0.13 Acres
Year built:
1982
A broker reciprocity listing Courtesy: STACEY TOWNS REALTY LLC 863-422-1585
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ADDITIONAL INFORMATION

Charming 3/2 in Cypress Landings on Lake Dexter! Welcome home to this adorable 3-bedroom, 2-bath property located in the highly desirable Cypress Landings community on beautiful Lake Dexter. Step inside to an inviting open floor plan featuring cathedral ceilings that make the living space feel bright, airy, and perfect for everyday living or entertaining. The large primary bedroom offers plenty of comfort with its walkin closet and a private ensuite bath complete with a convenient step in shower. Living in Cypress Landings means enjoying a lifestyle full of amenities, including: Community boat ramp, Fishing pier, Clubhouse, Heated pool, Tennis courts. All of this, plus a location that keeps you close to shopping, medical offices, dining, and more. This community does not allow short term rentals, ensuring a peaceful, residential atmosphere. A wonderful opportunity to enjoy lake access, great amenities, and a cozy home in a fantastic Winter Haven neighborhood!

Beds:
4
Baths:
2.00
Sq.Ft.:
2,257
Status:
NEW LISTING
MLS#:
L4965212
Type:
Single Family
Subdivision:
Reflections East Add
Lot size:
0.2 Acres
Year built:
2001
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY SMART 1 863-508-3000
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ADDITIONAL INFORMATION

More space, more flexibility, and more included! Located near LEGOLAND Florida Resort, this spacious Winter Haven home offers 2,257 square feet of total living area, including a permitted 320-square-foot addition completed in 2021. The interior features a bright main living area with vaulted ceilings, a separate dining space, generously sized bedrooms, an interior laundry room, and a well-equipped kitchen with ample cabinetry and counter space. The refrigerator, range, microwave, dishwasher, washer, and dryer are all included. Step outside to a fenced backyard designed for enjoying the Florida lifestyle. A brand-new permitted covered patio, completed in March 2026, provides an inviting shaded space for relaxing, grilling, or entertaining. The backyard also features mature shade trees and a paver gathering area with a built-in firepit and seating. Additional highlights include a complete HVAC system installed in 2023, a main house roof installed in 2017, a new patio roof installed in 2026, a two-car garage, an included security system, and eight included 360-degree security cameras. Conveniently positioned in Central Florida between Orlando and Tampa, the home provides access to major attractions, shopping, dining, recreation, and everything the Winter Haven area has to provide. With substantial living space, valuable permitted improvements, included appliances, and an outdoor area ready to enjoy, this home delivers features that are increasingly difficult to find at this price point. Schedule your private showing and see how much this property has to give.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,489
Status:
NEW LISTING
MLS#:
S5157963
Type:
Single Family
Subdivision:
Lake Winterset Acres Unit #2
Lot size:
0.48 Acres
Year built:
1972
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

A Dream come true in Winter Haven! This beautiful 4-bedroom, 2-bath home checks all the boxes: NO HOA, a private pool, and a spacious backyard. Enjoy comfortable indoor living and plenty of outdoor space to relax and entertain. Conveniently located in the Cypress Gardens area near LEGOLAND Florida, shopping, dining, and everyday conveniences. A wonderful combination of space, freedom, location, and Florida lifestyle. Schedule your private showing today!

Beds:
4
Baths:
3.00
Sq.Ft.:
1,933
Status:
NEW LISTING
MLS#:
O6443234
Type:
Single Family
Subdivision:
Peace Crk Reserve
Lot size:
0.13 Acres
Year built:
2024
A broker reciprocity listing Courtesy: RE/MAX ASSURED 800-393-8600
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ADDITIONAL INFORMATION

Welcome to this beautifully designed 4 bedroom, 2.5 bathroom two-story home, built in 2024, offering modern style, thoughtful upgrades, and easy maintenance living. Step inside to discover elegant tile flooring throughout the main level, creating a sleek and inviting atmosphere. The spacious kitchen features stunning quartz countertops, upgraded appliances, and beautiful gold accents that add a touch of sophistication to the heart of the home. Upstairs, you’ll find comfortable bedrooms with plush carpeting, including a spacious primary suite designed for relaxation. The open concept layout provides plenty of space for entertaining, everyday living, and making lasting memories. Step outside to enjoy the large paved backyard area, perfect for outdoor dining, entertaining, or creating your own private retreat. The backyard also features turf instead of traditional grass, providing a beautiful, low maintenance outdoor space without the hassle of regular mowing and upkeep. This move in ready home offers the perfect combination of comfort, style, and convenience.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,592
Status:
NEW LISTING
MLS#:
P4939917
Type:
Single Family
Subdivision:
Overlook Estates East
Lot size:
0.3 Acres
Year built:
1992
A broker reciprocity listing Courtesy: CROSBY & ASSOCIATES, INC. 863-293-5600
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ADDITIONAL INFORMATION

This Awesome 3 bedroom 3 bath home is ready for its you!!. Located in a GREAT gated community in off of Overlook Drive in SE Winter Haven this one has the perfect combination of location, and comfort. Check out the kitchen with nice countertops and wood cabinets. The rooms have great windows offering abundant natural light, and space for everyone. The 3 way split bedroom plan offers form, and function. The spacious yard offers peace, and privacy with no home in your back yard, Roof replaced in 2004.Check out this sweet property today. Step inside and you will love. Make it yours!!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,006
Status:
NEW LISTING
MLS#:
P4939900
Type:
Single Family
Subdivision:
Traditions Ph 02
Lot size:
0.13 Acres
Year built:
2015
A broker reciprocity listing Courtesy: CENTURY 21 MYERS REALTY LAKE WALES 863-676-4448
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ADDITIONAL INFORMATION

Discover exceptional Florida living in this fabulous Eco Smart 3-bedroom, 3-bath home with a den, ideally situated in the premier gated active-adult community of Traditions at Lake Ruby. Designed with comfort, efficiency, and entertaining in mind, this beautifully appointed home offers an impressive array of upgrades and thoughtful features. The desirable split-bedroom floor plan provides privacy and versatility, including a spacious Junior Bedroom Suite with its own ensuite bath—perfect for visiting family or guests. The well-equipped kitchen is a chef’s delight, featuring a center island with pendant lighting, fingerprint-resistant stainless-steel appliance package, recessed lighting, and 42-inch white upper cabinetry enhanced with crown molding, soft-close hinges, and brush nickel hardware. A generous walk-in pantry provides additional storage, while the pull-out cabinet organizers keep everyday items conveniently within reach. The spacious Living Room features wood laminate flooring and triple glass sliding doors that open to the extended lanai, seamlessly blending indoor and outdoor living. The open-concept design also incorporates a dedicated Dining Room and cheerful breakfast nook, providing plenty of space for family gatherings and entertaining. The generously sized Primary Bedroom Suite is enhanced with laminate flooring and dual walk-in closets featuring deluxe closet organizer systems. The luxurious Primary Bath offers a handicapped-accessible tiled shower with glass enclosure, comfort-height vanity with dual sinks, and linen closet for additional storage. Outdoor entertaining is effortless in the oversized screened lanai, featuring decorative stamped-concrete flooring, retractable solar screens and a built-in buffet and BBQ Grill—perfect for enjoying Florida’s year-round outdoor lifestyle. Additional amenities include a versatile Den/Office, Laundry Room with cabinetry, washer and dryer, ceiling fans with remote controls, and extensive storage throughout. Energy-efficient features include solar panels with a monthly solar expense of approximately $209, a 15-SEER HVAC system, AO Smith hybrid water heater, Low-E windows, radiant heat barrier, and architectural shingle roof installed in 2026. A stone facade, decorative stone curbing, and paved driveway add to the home’s impressive curb appeal. Additional upgrades include smart-lock entry, whole-house generator, retractable garage screen, keyless garage entry pad, and a two-car garage equipped with three overhead storage racks, workbench with matching cabinetry, and an overhead solar skylight. Traditions at Lake Ruby offers an exceptional active-adult lifestyle with an impressive selection of amenities and planned community activities. Residents enjoy a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting room, library, computer room, craft room, dog park, tennis courts, basketball court, bocce, shuffleboard, fitness center, aerobics studio, and so much more. Conveniently located near shopping, medical facilities, and major transportation routes, Traditions at Lake Ruby offers the perfect combination of resort-style amenities, energy-efficient living, and everyday convenience. HOME CAN BE PURCHASED FURNISHED

Beds:
4
Baths:
2.00
Sq.Ft.:
1,978
Status:
NEW LISTING
MLS#:
O6442966
Type:
Single Family
Subdivision:
Villamar
Lot size:
0.13 Acres
Year built:
2024
A broker reciprocity listing Courtesy: YOUR HOME SOLD GUARANTEED REALTY 407-566-2555
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ADDITIONAL INFORMATION

Welcome to this like-new, four-bedroom home in the desirable Villamar community! Built in 2024 and offering nearly 2,000 square feet of beautifully designed living space, this inviting home combines modern comfort, thoughtful design, and effortless Florida living. Step inside to discover a light-filled, open-concept floor plan where the kitchen, dining area, and great room flow seamlessly together—perfect for both relaxed everyday living and memorable gatherings. The heart of the home is the spacious kitchen, featuring stone countertops, a large center island with breakfast bar, stainless steel appliances, and a generous walk-in pantry. The desirable split-bedroom layout provides added privacy, while the spacious primary suite offers a walk-in closet and a private bath with dual sinks. Ceramic tile enhances the main living areas, with soft carpeting adding comfort to the bedrooms. Sliding glass doors open to the patio and backyard, creating a wonderful space to enjoy morning coffee, outdoor dining, or Florida’s year-round sunshine. Additional highlights include energy-efficient appliances, windows, insulation, HVAC, lighting, low-flow fixtures, an irrigation system, and an attached two-car garage. Villamar residents enjoy access to a community pool, playground, park, sidewalks, and recreational facilities. With four bedrooms, nearly 2,000 square feet, and the peace of mind that comes with a home that is only two years young, this is a truly special opportunity to settle into a beautiful home and begin making memories of your own.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,308
Status:
NEW LISTING
MLS#:
P4939887
Type:
Condo
Subdivision:
Winterset 03 A Condo Ph 01
Lot size:
0.02 Acres
Year built:
1989
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

Waterfront Living • Renovated Interior • Private Garage. Imagine ending your day with a beautiful Florida sunset over Lake Winterset. This beautifully renovated 2-bedroom, 2-bath condominium offers something that is hard to find in condo living—a private 1-car garage, expansive waterfront views, and the added character of a second-floor residence with vaulted ceilings and skylights. Located in the gated Winterset community, this home combines a relaxed lakefront lifestyle with a thoughtfully updated interior that is comfortable, stylish, and move-in ready. The kitchen is truly the centerpiece, featuring abundant cabinetry, granite countertops, stainless-steel appliances, a stylish tile backsplash, and an oversized counter with generous breakfast-bar seating. The open design creates a spacious connection between the kitchen and living area. The main living area features rich wood flooring and a striking built-in entertainment center with display shelving and architectural detail. Step through the sliding glass doors and enjoy the true highlight of this home—the enclosed waterfront lanai overlooking Lake Winterset. With room for both dining and comfortable seating, this becomes an extension of the living space and an ideal place to enjoy the beauty of Florida's nature. Imagine starting your morning with coffee overlooking the lake or relaxing at the end of the day as the sun sets across the water. The views aren't simply outside your door—they become part of everyday life. Renovated throughout, this home offers a cohesive blend of comfort and style. Plantation shutters, updated bathrooms, wood flooring, and carefully selected finishes create a polished feel throughout. The primary bedroom offers beautiful lake views, while the second bedroom provides flexibility for guests, an office, or additional living space. A unique feature of this residence is the installed stair chair, providing added convenience between the garage level and the second-floor home. A 1-car garage is an especially desirable feature for condo living, providing secure parking and valuable additional storage. Having your own garage adds a level of convenience that is not commonly found with condominium living. Set within the gated Winterset community, this home offers a welcoming waterfront lifestyle surrounded by beautiful lakes, mature landscaping, and green spaces. Residents can enjoy the waterfront clubhouse, pool and spa, along with an active and social community atmosphere. Winterset provides opportunities for boating, fishing, and enjoying the peaceful waterfront setting, while remaining conveniently close to shopping, dining, entertainment, theme parks, airports, and Florida's east and west coast beaches. Whether you're looking for a full-time residence, seasonal retreat, or an easy-to-maintain Florida getaway, 809 Magnolia Place offers the rare combination of lakefront views, thoughtful renovations, vaulted ceilings, a private garage, and a lifestyle centered around the water.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,515
Status:
NEW LISTING
MLS#:
R4912028
Type:
Single Family
Subdivision:
Villamar Ph 3
Lot size:
0.11 Acres
Year built:
2023
A broker reciprocity listing Courtesy: LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV 407-207-2220
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ADDITIONAL INFORMATION

WELCOME HOME TO VILLAMAR — where modern comfort meets the Florida lifestyle! Beautifully maintained and truly move-in ready, this single-story Winter Haven home offers the bright, open-concept design today's buyers are looking for, along with a fantastic location in the desirable VillaMar community. Step inside and you're immediately welcomed by an impressive open living space with high ceilings, abundant natural light and tile flooring throughout the main living areas. The spacious layout effortlessly connects the kitchen, dining and living areas, creating the perfect setting for everyday living, entertaining friends, or simply relaxing at home. The kitchen is truly the heart of this home and is designed to impress. Featuring shaker-style cabinetry, granite countertops, stainless-steel appliances, recessed lighting and an oversized center island with a double-basin sink, there's plenty of prep space, storage and room to gather. The expansive island also provides an ideal spot for casual seating and entertaining while keeping the kitchen completely connected to the living area. The private primary suite offers a relaxing retreat complete with a generous walk-in closet and an ensuite bathroom featuring dual vanities with granite countertops and a soaking tub. Additional bedrooms provide flexibility for family, guests, a home office, hobby room or whatever best fits your lifestyle. A second full bathroom features coordinating granite countertops and a tub/shower combination. Step outside to your covered lanai and backyard, giving you your own outdoor space to enjoy Florida's beautiful weather. Whether you envision morning coffee outside, weekend barbecues, a play area or a space for your four-legged companions, the backyard is ready to make your own. Additional highlights include an interior laundry room, recessed lighting, window blinds, ample storage and an attached 2-car garage. And the lifestyle doesn't stop at your front door. VillaMar brings resort-style living right to the neighborhood, with a community swimming pool, shaded seating areas, playground and park areas, green spaces, and beautiful water and conservation surroundings. The location is another standout. VillaMar sits in southeast Winter Haven with convenient access to US-27, US-17 and SR-60, putting shopping, dining, recreation and surrounding Central Florida destinations within easy reach. Even better, LEGOLAND Florida Resort and Peppa Pig Theme Park are approximately 4.4 miles away, while Winter Haven's famous lakes, outdoor recreation and charming downtown are also nearby. Walt Disney World is approximately 35 miles from the community. Why wait for new construction when you can have a beautiful, move-in-ready home in an established community with the amenities already waiting for you? Come experience the space, convenience and lifestyle VillaMar has in store. Schedule your private showing today and see why this Winter Haven home deserves to be at the top of your list!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,266
Status:
NEW LISTING
MLS#:
TB8549558
Type:
Single Family
Subdivision:
Lake Daisy Estates
Lot size:
0.14 Acres
Year built:
2005
A broker reciprocity listing Courtesy: CHARLES RUTENBERG REALTY INC 727-538-9200
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ADDITIONAL INFORMATION

Professionally remodeled and completely turnkey, this pristine 3-bedroom, 2-bathroom single-story home offers the ultimate in modern, low-maintenance living. Located approximately one mile from Cypress Gardens / LEGOLAND Florida, this property delivers an exceptional location paired with total peace of mind, featuring a brand-new roof, an attached two-car garage, and a private backyard with a convenient storage shed. Inside, the light-filled, open-concept floor plan showcases a spacious living and dining area with soaring vaulted ceilings, updated contemporary light fixtures, and brand-new wood-look luxury vinyl plank flooring that runs seamlessly throughout—completely carpet-free. The centerpiece of the home is the stunning, fully renovated kitchen equipped with premium quartz countertops, brand-new cabinetry, and a modern layout designed for entertaining. Both bathrooms have been completely updated, featuring new vanities, modern matte-black plumbing fixtures, and clean, bright wall tile surrounding the tub/shower combination. Finished with fresh paint inside and out, this high-end, zero-maintenance remodel is entirely move-in ready. Schedule your private showing today.

Beds:
6
Baths:
5.00
Sq.Ft.:
3,920
Status:
NEW LISTING
MLS#:
O6441688
Type:
Single Family
Subdivision:
Hart Lake Cove Ph 02
Lot size:
0.19 Acres
Year built:
2006
A broker reciprocity listing Courtesy: CFRP REALTY LLC 407-682-8686
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ADDITIONAL INFORMATION

"Looking for a large home at a reasonable price? This spacious 6-bedroom home in Hart Lake Cove could be the one for you! Freshly painted with new carpet throughout most of the home, this property offers an impressive amount of living space and flexibility. The first floor features a living room, family room, dining area, eat-in kitchen, half bath, and a generously sized bedroom with its own private bathroom—ideal for guests, extended family, or a private home office. The spacious kitchen offers plenty of room to cook and entertain and features a center island and stainless steel appliances. Upstairs, you’ll find a large loft, five additional bedrooms, and three bathrooms, providing plenty of room for everyone. The loft offers even more flexible space for a game room, media area, study space, or second family room. Outside, enjoy a large fenced backyard with plenty of room for outdoor activities, pets, entertaining, or simply relaxing. A 3-car garage provides excellent parking and additional storage space. With 6 bedrooms, multiple living areas, a large loft, 4.5 bathrooms, a 3-car garage, and a spacious fenced backyard, this home offers the room and versatility that can be difficult to find at this price point. Upgrades over the years include new roof installed in 2021; new electric water heater in 2022; new heat pump systems in 2019; exterior freshly painted in 2021; new gutters added in 2020. Whether you need space for a large household, extended family, guests, or multiple home offices, this Hart Lake Cove home has plenty to offer. Schedule your private showing today!"

Beds:
4
Baths:
2.00
Sq.Ft.:
1,840
Status:
NEW LISTING
MLS#:
TB8544819
Type:
Single Family
Subdivision:
Villamar
Lot size:
0.13 Acres
Year built:
2026
A broker reciprocity listing Courtesy: MERITAGE HOMES OF FL REALTY 813-703-8860
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ADDITIONAL INFORMATION

Under Construction. Brand new, energy-efficient home available by Sep 2026! Prepare dinner while catching up on the days events from this home's open kitchen which overlooks a spacious great room and dining area. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,840
Status:
NEW LISTING
MLS#:
TB8544818
Type:
Single Family
Subdivision:
Villamar
Lot size:
0.13 Acres
Year built:
2026
A broker reciprocity listing Courtesy: MERITAGE HOMES OF FL REALTY 813-703-8860
View additional info

ADDITIONAL INFORMATION

Under Construction. Brand new, energy-efficient home available by Sep 2026! Prepare dinner while catching up on the days events from this home's open kitchen which overlooks a spacious great room and dining area. Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Beds:
2
Baths:
2.00
Sq.Ft.:
823
Status:
NEW LISTING
MLS#:
O6442486
Type:
Condo
Subdivision:
Lake Kit Condo
Lot size:
0.01 Acres
Year built:
1982
A broker reciprocity listing Courtesy: BEYCOME OF FLORIDA LLC 804-656-5007
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ADDITIONAL INFORMATION

Welcome to this charming condominium located at 628 Pavare Ct in the beautiful city of Winter Haven, FL. Low HOA $284. This residence accords a cozy living space of 823 square feet, efficiently designed to provide comfort and functionality. With two spacious bedrooms, this home is appropriate for those seeking a comfortable and low-maintenance lifestyle. Renovated. Near shopping centers. The property is situated on a lot where you can enjoy all the benefits of condo living without the hassle of yard upkeep. The open floor plan allows for easy movement throughout the space, creating a warm and inviting atmosphere. The surrounding area accords a tranquil environment, making it a great place to unwind and relax.

Beds:
5
Baths:
4.00
Sq.Ft.:
2,701
Status:
NEW LISTING
MLS#:
L4965075
Type:
Single Family
Subdivision:
Villamar Ph 4
Lot size:
0.14 Acres
Year built:
2022
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY SMART 1 863-508-3000
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ADDITIONAL INFORMATION

Short Sale. Short Sale — Third Party Approval Required. Welcome to 2639 San Marco Way, a spacious 5-bedroom, 3.5-bathroom two-story home offering 2,701 square feet of flexible living space in Winter Haven, FL. This short sale opportunity presents an excellent chance to acquire a generously sized home at an improved price point in an established Winter Haven community. The two-story layout provides excellent separation of space, with room for large households, multigenerational living, home offices, or guest accommodations. Five bedrooms and three and a half bathrooms give the kind of flexibility that is increasingly difficult to find at this price point. Conveniently located near shopping, dining, medical facilities, and the beautiful Winter Haven Chain of Lakes, with easy access to US-27 and major routes to both Orlando and Tampa. This is a short sale subject to lender approval. Being sold as-is. Buyer and buyer's agent to verify all information including HOA fees, community details, restrictions, measurements, and permitted uses. A rare opportunity to own a large Winter Haven home — schedule your showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,893
Status:
NEW LISTING
MLS#:
TB8548427
Type:
Single Family
Subdivision:
Terranova Ph 03
Lot size:
0.24 Acres
Year built:
2004
A broker reciprocity listing Courtesy: KELLER WILLIAMS TAMPA CENTRAL 813-865-0700
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ADDITIONAL INFORMATION

Welcome home to this stunning 3-bedroom, 2-bathroom residence tucked into the sought-after, gated community of Terranova. From the moment you step inside, an open floor plan invites you through sun-filled living spaces accented by elegant crown moulding and custom built-ins. The chef-inspired kitchen anchors the home with generous counter space and a breakfast bar — perfect for casual mornings or entertaining guests. Plantation shutters throughout add a touch of timeless charm while offering privacy and light control in every room. Step outside to a spacious backyard, a blank canvas ready for weekend barbecues, a play area, or the pool of your dreams. Beyond your front door, Terranova's gated setting offers peace of mind just minutes from shopping, dining, and medical facilities — the perfect blend of tranquility and convenience. Don't miss this one — call today to schedule your private showing!

Beds:
2
Baths:
2.00
Sq.Ft.:
823
Status:
NEW LISTING
MLS#:
L4965031
Type:
Condo
Subdivision:
Lake Kit Condo
Lot size:
0.01 Acres
Year built:
1982
A broker reciprocity listing Courtesy: LOCKHART & ASSOCIATES INC 863-293-1234
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ADDITIONAL INFORMATION

2 Bedroom/2 Bathroom downstairs Condo in Orchid Springs. Laminate flooring throughout. Kitchen with gas stove, stackable washer/dryer, and pass thru window to Dining area. Primary Bedroom has a walk in closet. Close to shopping, Legoland, and minutes to HWY 27. Call today for an appointment to view.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,204
Status:
Active
MLS#:
TB8548086
Type:
Single Family
Subdivision:
Cypresswood
Lot size:
0.21 Acres
Year built:
1986
A broker reciprocity listing Courtesy: MARK SPAIN REAL ESTATE 855-299-7653
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ADDITIONAL INFORMATION

Welcome to The Meadows, a desirable community within Cypresswoods! This well-maintained home offers the perfect combination of comfort, convenience, and beautiful golf course views. Ideally situated along the golf course, you can enjoy your morning coffee while taking in the scenic views of the 13th hole. The home has been thoughtfully maintained and features a 2025 roof and 2023 HVAC system, providing added peace of mind for the next owner. The property also includes an oversized garage with a workbench. Schedule your showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,129
Status:
Active
MLS#:
L4964769
Type:
Single Family
Subdivision:
N/a
Lot size:
6.55 Acres
Year built:
2004
A broker reciprocity listing Courtesy: FLORIDA REAL ESTATE COMPANY 863-701-3487
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ADDITIONAL INFORMATION

Welcome to your slice of heaven in Winter Haven! Situated on just over 6.5 acres you will find this charming 3/2/2 Cassidy custom pool home surrounded by green meadows and mature oak trees. 4401 Chambliss Rd. offers space, freedom, and a lifestyle you simply won’t find inside typical neighborhoods. This expansive homestead provides room for horses, chickens, gardens, equipment, and future additions, all thanks to the no-HOA flexibility that lets you live the way you choose. There is a refreshing pool perfect for Florida summers and is surrounded by mature trees and wide-open land that create exceptional privacy. A large pond sits quietly among huge cypress trees on the property, adding a peaceful backdrop without dominating the landscape. Acreage of this size is almost unheard of in Winter Haven, making this a standout opportunity for anyone seeking space, seclusion, and the freedom to have a true country retreat while staying close to town conveniences. Updates include: HVAC 2018, Roof 2024, Water Heater 2018. 2 large sheds and large RV/Boat shed.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,666
Status:
Active
MLS#:
P4939773
Type:
Other
Subdivision:
Cypresswood
Lot size:
0.05 Acres
Year built:
1987
A broker reciprocity listing Courtesy: VILLAGE REALTY OF WINTER HAVEN 863-299-6767
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ADDITIONAL INFORMATION

BEAUTIFUL VILLA READY TO MOVE IN! A brand-new HVAC system (June 2026), along with new insulation throughout the attic. Features include cathedral ceilings, elegant detailed trimwork with decorative corner blocks throughout, new flooring, plantation shutters on the windows, and three sets of French doors. The upgraded kitchen features stainless steel appliances, double ovens, and a built-in pantry with pull-out shelves. A utility closet provides additional storage, and the interior laundry room includes a full-size washer and dryer. The primary bathroom features dual showers and two vanities with wood cabinetry, while the second bathroom includes a jetted bathtub and wood cabinet vanity. Both bathrooms also feature skylights. Golf course frontage and two outdoor patio areas, with one overlooking the 8th fairway, plus a second patio with concrete privacy walls. HOA fee includes roof replacement when needed, so you never have to worry about roof expenses. Cypresswood Country Club community offers golf, a Jr. Olympic-size pool, tennis courts, pickleball courts, a restaurant and bar, social events, live music three nights a week, and lush, well-maintained surroundings. Come take a look at this one!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,678
Status:
Active
MLS#:
O6441050
Type:
Single Family
Subdivision:
Gaines Cove
Lot size:
0.55 Acres
Year built:
2005
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 407-647-1211
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ADDITIONAL INFORMATION

Virtually Staged. Welcome to 3831 Gaines Dr, where beautifully updated interiors, exceptional outdoor living, and the best of the Winter Haven lifestyle come together. Situated on an impressive half-acre-plus homesite in the established Gaines Cove area, this immaculate 3-bedroom plus dedicated office home offers the space, privacy, and character that can be difficult to find. The location is a standout. Enjoy being just minutes from the Winter Haven Chain of Lakes, with multiple nearby options for boat ramps and lake access, making it easy to spend your days boating, fishing, skiing, or exploring Winter Haven’s interconnected lakes. LEGOLAND Florida Resort is also just minutes away, along with shopping, dining, and the everyday conveniences of the Cypress Gardens area. Inside, an inviting open floor plan welcomes you with spacious living areas designed for both everyday comfort and entertaining. Architectural details, abundant natural light, plantation shutters, and a fireplace with built-ins add warmth and character throughout. The beautifully updated kitchen features brand-new appliances and flows seamlessly into the main living area, while updated bathrooms and thoughtful improvements throughout create a polished, move-in-ready feel. A dedicated office with French doors provides the perfect space for working from home, studying, or additional flex space. The upgrades go well beyond what you immediately see. The home features a Kinetico water filtration system, allergen air filtration system, and a Tesla charging station, adding modern convenience and functionality to an already impressive property. Step outside and discover what truly sets this home apart. The expansive screened outdoor living area creates your own private Florida backyard retreat, centered around a heated saltwater pool with plenty of space for relaxing and entertaining. The substantial covered lanai features an impressive outdoor kitchen with built-in grill, vent hood, sink, and refrigeration, complemented by generous outdoor dining and seating areas. Remote-controlled power sun shades on the rear lanai provide added shade, privacy, and comfort at the touch of a button, making this incredible space even more enjoyable throughout the day. And unlike many pool homes, the backyard doesn't end at the screened enclosure. Beyond the pool is an expansive fenced yard with abundant usable green space, mature trees, and beautifully maintained landscaping. The combination of a large homesite, resort-style pool area, covered outdoor living, and substantial backyard creates a wonderful sense of openness and privacy. Curb appeal is equally impressive, with a large paver driveway, expansive front lawn, mature landscaping, and welcoming covered front porch creating a memorable first impression. Spend the morning boating on the Chain of Lakes, the afternoon relaxing in your heated saltwater pool, cook dinner in your outdoor kitchen, and finish the evening unwinding on the lanai. With LEGOLAND just minutes away and shopping, dining, recreation, and multiple lake-access options nearby, 3831 Gaines Dr offers more than a beautifully updated home—it offers the Winter Haven lifestyle.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,112
Status:
Active
MLS#:
O6441023
Type:
Single Family
Subdivision:
Villa Mar 40's
Lot size:
0.15 Acres
Year built:
2026
A broker reciprocity listing Courtesy: LENNAR REALTY 800-229-0611
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ADDITIONAL INFORMATION

Under Construction. The first floor of the stunning Edison two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,925
Status:
Active
MLS#:
L4964941
Type:
Single Family
Subdivision:
Fla Highlands Co Sub
Lot size:
0.23 Acres
Year built:
1971
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 863-294-7541
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ADDITIONAL INFORMATION

INVESTMENT OPPORTUNITY + PRIMARY RESIDENCE POTENTIAL! This spacious 4-bedroom, 2-bathroom home sits on a desirable corner lot with a fully fenced yard and a 20x30 metal building offering excellent storage, workshop, or hobby space. Currently operating as an active, income-producing Airbnb, this property offers the flexibility to continue as a short-term rental or make it your own primary residence. The fourth bedroom and primary bedroom feature added mini-split systems for enhanced comfort. The roof and flooring were replaced in 2021, providing an added bonus for the next owner. Whether you're looking for an income-producing investment or a home with room for your family, this property is ready to deliver.

Beds:
2
Baths:
1.00
Sq.Ft.:
826
Status:
Active
MLS#:
L4964839
Type:
Condo
Subdivision:
Orchid Spgs Village #300
Lot size:
0.01 Acres
Year built:
1974
A broker reciprocity listing Courtesy: FLORIDA REAL ESTATE COMPANY 863-701-3487
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ADDITIONAL INFORMATION

Available for immediate occupancy, this lovely condo is updated and features low maintenance lifestyle with superb location. Located close to golf, fishing and water sports, close to LegoLand and shopping. The location is private and off the beaten path, ideal for a starter home or winter retreat. Upon entering the unit, you will note the fresh interior, open living area, and updated kitchen featuring stainless appliances with gas range and all new cabinetry and butcher block countertops. The community features laundry facilities and private mailboxes for security. Designated parking spaces for each unit. Close to LegoLane and Highway 27 for ease of commutes to all things Central Florida including golf, water sports, theme parks, and much more.

Beds:
2
Baths:
2.00
Sq.Ft.:
989
Status:
Active
MLS#:
G5117624
Type:
Manufactured Home
Subdivision:
Orange Manor West Coop Inc
Lot size:
0.11 Acres
Year built:
1984
A broker reciprocity listing Courtesy: MOSAIC SERVICES LLC 352-617-7606
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ADDITIONAL INFORMATION

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 989 Square ft. 2 bedroom 2 bath 1984 Homes of Merit with an enclosed front facing Florida. The king size master bedroom has a walk-in closet and a private bathroom with a tub shower. The guest bedroom also has a walk-in closet. 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.

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Andrea Conner, License #BK3437731, Xome Inc., License #1043756, [email protected], 844-400-9663, 750 State Hwy 121 Bypass, Suite 100, Lewisville, TX 75067


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Winter Haven 33884 Real Estate

Winter Haven is located in Florida. Winter Haven, Florida 33884has a population of 48,707. Winter Haven 33884 is less family-centric than the surrounding county with 24.73% of the households containing married families with children. The county average for households married with children is 26.62%.

The median household income in Winter Haven, Florida 33884 is $50,842. The median household income for the surrounding county is $55,099 compared to the national median of $69,021. The median age of people living in Winter Haven 33884 is 41 years.

Winter Haven Weather

The average high temperature in July is 92.5 degrees, with an average low temperature in January of 49.7 degrees. The average rainfall is approximately 51.2 inches per year, with 0 inches of snow per year.

Winter Haven Map

Winter Haven Real Estate Market Conditions

  • Median sales price

    $295,990
    25.4%
    change since last quarter
  • # Active listings

    404
    30-day change

Winter Haven Schools and Demographics

Education near Winter Haven, FL

City County
High School Graduates 88.28 86.36
College Degree - 2 year 10 9.74
College Degree - 4 year 19.99 21.01
Graduate Degree 4.94 5.22
Expenditures per Student 10,984 10,984
Students per Teacher 17.8 17.8

Elementary Schools near Winter Haven, FL

Grades Students P/T Ratio ZIP
Chain of Lakes Elementary School PK - 05 1,077 17.4 33884
Davenport School of the Arts PK - 08 1,086 16 33837
Dundee Elementary Academy PK - 04 512 13.8 33838
Eagle Lake Elementary School PK - 05 473 15.8 33839
Eastside Elementary School PK - 05 1,040 16.3 33844
Elbert Elementary School PK - 05 638 15.6 33881
Frank E. Brigham Academy KG - 05 527 15.5 33880
Fred G. Garner Elementary School PK - 05 646 13.7 33881
Garden Grove Elementary School PK - 05 562 15.2 33884
Hartridge Academy KG - 05 237 18.2 33881
Horizons Elementary School PK - 05 1,059 16.8 33837
Inwood Elementary School PK - 05 412 15.3 33880
Jewett School of the Arts PK - 08 738 15.1 33881
John Snively Elementary PK - 05 467 15.6 33880
Lake Shipp Elementary School PK - 05 550 17.2 33880
Loughman Oaks Elementary School PK - 05 1,027 15.1 33837
Pinewood Elementary School PK - 05 678 14.7 33839
South McKeel Academy PK - 08 1,167 16.7 33803
Wahneta Elementary School PK - 05 502 16.2 33880
Winter Haven Head Start PK - PK 35 17.5 33881

Middle Schools near Winter Haven, FL

Grades Students P/T Ratio ZIP
Crystal Lake Middle School 06 - 08 942 15.4 33801
Denison Middle School 06 - 08 842 15.9 33880
Discovery Academy of Lake Alfred 06 - 08 1,040 18.3 33850
Dundee Ridge Middle Academy 05 - 08 677 15.4 33838
Jere L. Stambaugh Middle 06 - 08 851 17.7 33823
Lake Alfred-Addair Middle School 06 - 08 827 18.4 33850
Lake Gibson Middle School 06 - 08 1,130 16.6 33809
Lake Marion Creek Middle School 05 - 08 964 18.2 34759
Lakeland Highlands Middle School 06 - 08 1,217 18.4 33813
Mulberry Middle School 06 - 08 1,035 18.2 33860
Shelley S. Boone Middle School 06 - 08 923 17.4 33844
Southwest Middle School 06 - 08 852 16.4 33803

High Schools near Winter Haven, FL

Grades Students P/T Ratio ZIP
Auburndale Senior High School 09 - 12 1,640 19.5 33823
Bartow Senior High School 09 - 12 2,039 17 33830
George W. Jenkins Senior High 09 - 12 2,319 20 33813
Haines City Senior High School 09 - 12 2,422 20.4 33844
Kathleen Senior High School 09 - 12 2,124 19.9 33815
Lake Gibson Senior High School 09 - 12 1,834 19.9 33809
Lake Region High School 09 - 12 1,892 19.9 33839
Lake Wales Senior High School 09 - 12 1,439 22.1 33853
Lakeland Senior High School 09 - 12 2,139 18.3 33801
Ridge Community High School 09 - 12 2,462 20.9 33837
Tenoroc High School 09 - 12 1,170 16.3 33801
Winter Haven Senior High School 09 - 12 1,953 22.2 33880

Ungraded Schools near Winter Haven, FL

Grades Students P/T Ratio ZIP
* Davenport Community Campus 09 - 12 309 34.3 33837
* Highlands Youth Academy 09 - 12 80 7.3 33825
* Maynard A. Traviss Career Center 08 - 12 243 4 33803
* Polk County Sheriff's Central Center 07 - 12 32 16 33830
* Ridge Career Center 09 - 12 123 3.2 33881
* Transition School 11 - 12 59 33830
Bartow Youth Academy 06 - 12 22 11 33830
Bill Duncan Opportunity Center 06 - 12 169 12.1 33803
Davenport Adult and Career Education Center AE - AE 0 33837
Don E Woods Opportunity Center 06 - 12 127 9.1 33838
Doris A. Sanders Learning Center PK - 12 88 5.2 33801
East Area Adult School AE - AE 0 33823
ESE Countywide KG - 12 81 8.1 33801
Future School UG - UG 0 33830
Gause Academy of Leadership 06 - 12 240 12 33830
Jean O'Dell Learning Center PK - 12 77 7.7 33830
Karen M. Siegel Academy PK - 12 166 9.2 33850
McKeel Academy of Technology 06 - 12 1,166 16.2 33815
Mulberry Step Up Academy UG - UG 0 33860
New Horizons 06 - 12 16 16 33860
Pace Center for Girls 06 - 12 45 7.5 33815
Polk County Sheriffs Regional Detention Center 05 - 12 30 10 33830
Polk Full Time Eschool KG - 12 104 33801
Polk Halfway House 05 - 12 23 11.5 33830
Polk Pre-Collegiate Academy 09 - 10 109 33823
Polk Virtual Franchise 06 - 12 0 33801
Polk Virtual Instruction (Course Offerings) PK - 12 0 33801
Polk Virtual Instruction Program KG - 12 43 131 33801
Ridge Teen Parent Program 06 - 12 71 33881
Roosevelt Academy 06 - 12 290 11.6 33853
Sheriff's Youth Villa 05 - 12 7 3.5 33830
West Area Adult/Community School AE - AE 0 33815
Winter Haven Pace 01 - 12 5 33880

Demographics near Winter Haven, FL 33884

Zip Code City
Neighborhood Type Suburban
Population 48,707 713,148
Population Density 1,520 397
Median Age 41 40.1
People per Household 2.7 2.8
Median Household Income 50,842 55,099
Average Income per Capita 27,296 27,909

Real estate near Winter Haven