Winter Haven FL Real Estate & Homes for Sale

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,077
Status:
NEW LISTING
MLS#:
A11975721
Type:
Single Family
Subdivision:
356715
Lot size:
0.14 Acres
Year built:
1996
Courtesy: Miami New Realty Cristina De Oliveira 305-909-3536
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ADDITIONAL INFORMATION

Charming furnished 3-bedroom, 1.5-bath block home in a well-established Winter Haven neighborhood with NO HOA. Features include an updated eat-in kitchen with shaker cabinets, granite countertops, and stainless-steel appliances. A/C replaced in 2022 and roof updated in 2016. Tile flooring in main areas, carpet in bedrooms, a separate laundry room, and a 1-car garage. Enjoy a private backyard with mature mango and kumquat trees and no rear neighbors. Currently operating as a successful Airbnb, generating approximately $4,000 in monthly profit, this is an excellent opportunity for investors or homeowners seeking income potential.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,502
Status:
NEW LISTING
MLS#:
O6388091
Type:
Single Family
Subdivision:
Garden Grove South Add
Lot size:
0.2 Acres
Year built:
1980
A broker reciprocity listing Courtesy: CARDINAL REALTY GROUP, LLC. 305-910-2902
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ADDITIONAL INFORMATION

Welcome to this well-maintained 3-bedroom, 2-bathroom home located in Winter Haven! Offering 1,502 square feet of living space, this property features a functional layout with plenty of potential for personalization. Major systems have been updated for peace of mind, including a roof, A/C, and water heater all approximately 5 years old. The home is equipped with impact windows and doors installed about 8 years ago, providing added protection and energy efficiency. The kitchen includes a refrigerator and dishwasher that are only 1 year old, along with a stove that is approximately 7 years old. While the home is in good overall condition, it presents a great opportunity for cosmetic updates to match your personal style. Full 3D walk-through video available upon request. PLEASE NOTE - I AM NOT AVAILABLE ON THE SABBATH/SATURDAYS

Beds:
2
Baths:
2.00
Sq.Ft.:
1,647
Status:
NEW LISTING
MLS#:
O6388012
Type:
Single Family
Subdivision:
Gates Lake Region
Lot size:
0.19 Acres
Year built:
2004
A broker reciprocity listing Courtesy: BEYCOME OF FLORIDA LLC 804-656-5007
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ADDITIONAL INFORMATION

Lovely 2 bedroom and 2 bathroom home located in a private gated community of just over 100 homes in Winter Haven, FL. Situated between Tampa and Orlando with easy access to both international airports. Short distance to theme parks, Legoland, Bok Tower Gardens. New Publix grocery store opening soon is a short drive away. New HVAC installed in 2022. Freshly painted interior and exterior. House overlooks a community park which makes a nice setting for relaxing afternoons and visiting with neighbors. Unique lot shape reveals a beautiful, secluded backyard for gardening and plant enthusiasts. Backyard patio area is a great spot to relax and enjoy quiet evenings.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,030
Status:
NEW LISTING
MLS#:
L4959894
Type:
Condo
Subdivision:
Imperial Harbours
Lot size:
0.01 Acres
Year built:
1974
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY SMART 1 863-508-3000
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ADDITIONAL INFORMATION

Welcome to 333 Lake Howard Dr NW, Unit 313A — a beautifully updated 2-bedroom, 2-bath condo located on the top (3rd) floor of a well-maintained 55+ community. The building offers elevator access and is wheelchair accessible, providing both comfort and convenience. This move-in ready unit features large windows in the living room overlooking the community pool, filling the space with natural light and offering peaceful views. Recent updates include all new kitchen cabinets and countertops, a new lanai cabinet, upgraded bathrooms, a new walk-in shower, new carpet throughout, fresh interior paint, new light fixtures, and new vent covers. The roof has also been replaced, adding additional value and peace of mind. Residents enjoy a variety of amenities including a community pool, fitness center, and direct lake access to Lake Howard. The private dock and boat parking make it easy to enjoy fishing, relaxing by the water, or docking your boat — all included in the HOA dues. Additional features include assigned covered carport parking and a 4x4x4 extra storage space located on the 2nd floor. Enjoy low-maintenance living with resort-style amenities in a prime location.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,334
Status:
NEW LISTING
MLS#:
L4959772
Type:
Condo
Subdivision:
Casa Del Sol Condo Village Ph 02
Lot size:
0.03 Acres
Year built:
1976
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 863-294-7541
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ADDITIONAL INFORMATION

Welcome to Casa Del Sol, a desirable lakefront community on Lake Hartridge with access to the Winter Haven Chain of Lakes. This spacious 2bd/2.5 bath condo offers 1,334 sq. ft. of comfortable living with a smart two-story layout—main living areas downstairs and both bedrooms upstairs. The home incorporates rustic farmhouse design elements throughout, including decorative farmhouse wall paneling that adds warmth, texture, and character to the living spaces. Natural wood furnishings and neutral tones complement the farmhouse aesthetic, blending comfort with timeless style. This bedroom features a relaxed coastal design with soothing blue tones and nautical accents that create a bright, airy retreat. A bold navy accent wall highlights the space, complemented by decorative fishing net wall art and seaside décor. Large windows dressed in sheer navy curtains allow natural light to fill the room, enhancing the breezy coastal vibe. A second bedroom showcases a soft coastal palette with tranquil turquoise walls and light, breezy window treatments. The rustic whitewashed headboard adds a beach-cottage feel while coordinating with the natural textures and pastel bedding. The room’s calming color scheme and light-filled atmosphere create a peaceful, seaside-inspired retreat perfect for guests or family. The bathroom is enhanced with a sliding barn door, a popular farmhouse feature that combines charm with functionality. The door’s rustic wood finish and exposed hardware create a stylish focal point while maximizing space and adding a touch of modern farmhouse appeal. Enjoy low-maintenance living with HOA fees covering city water, sewer/garbage, exterior building maintenance, grounds care, and pool service. Community amenities include a clubhouse, two pools, tennis courts, shuffleboard, and a community dock with direct Lake Hartridge access. A rare bonus in condo living—an attached 2-car garage. Centrally located near major roadways for easy commuting to Lakeland, Auburndale, and the I-4 corridor, yet tucked into a peaceful residential setting close to downtown events, waterfront paths, and local dining. Ideal as a primary residence, seasonal home, or investment property. Opportunities like this don’t last—schedule your private showing today.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,158
Status:
NEW LISTING
MLS#:
O6386232
Type:
Single Family
Subdivision:
Queens Cove Ph 02
Lot size:
0.14 Acres
Year built:
1994
A broker reciprocity listing Courtesy: ENTERA REALTY LLC 888-216-6364
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ADDITIONAL INFORMATION

This traditional 3-bedroom, 2-bathroom home is located in the established Queens Cove Ph 02 neighborhood. Designed with a functional and classic layout, this residence offers a comfortable living environment perfectly suited for a variety of lifestyles. The heart of the home features a traditional floor plan that provides a clear and smart separation of living spaces. The kitchen is beautifully updated with sleek quartz countertops and Stainless steel appliances, creating a modern and stylish space for meal preparation and entertaining. Situated in a prime location, this home is just minutes away from local essentials, including shopping, dining, and parks. Whether you are searching for a forever home or a smart investment opportunity, this property offers both convenience and potential. Schedule your private showing today!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,080
Status:
NEW LISTING
MLS#:
O6387580
Type:
Single Family
Subdivision:
Inman Grvs Ph 2
Lot size:
0.13 Acres
Year built:
2023
A broker reciprocity listing Courtesy: MY REALTY GROUP, LLC. 786-847-7421
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ADDITIONAL INFORMATION

Welcome to 652 Grove St, a versatile and spacious 'Freedom' model home in the heart of Winter Haven! This unique property has a main residence featuring 3 bedrooms, 2 bathrooms, a dedicated office space, and a private laundry room. The open-concept layout includes a 2-car garage and plenty of natural light throughout. What sets this home apart is the fully independent Annex/Guest House. This additional living space includes 1 bedroom, 1 bathroom, a semi-equipped kitchen, and its own laundry area—perfect for a mother-in-law suite, a private guest retreat. Conveniently located with easy access to US-27 and local amenities. Schedule your private tour today.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,836
Status:
NEW LISTING
MLS#:
S5144475
Type:
Single Family
Subdivision:
Emily Estates
Lot size:
0.15 Acres
Year built:
2005
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

Welcome to 1805 Emily Drive—where space, comfort, and outdoor living come together to create a home that truly stands apart in today’s market. Nestled in a well-positioned area of Winter Haven, this 4-bedroom, 2.5-bath pool home delivers the flexibility today’s buyers are actively seeking. Step inside and immediately notice the expansive layout designed to adapt to your lifestyle. The main level showcases ceramic rustic tile and luxury vinyl plank flooring, while the staircase and entire upper living areas have also been upgraded with durable, modern luxury vinyl—offering both style and easy maintenance. Upstairs, the oversized primary suite creates a true owner’s retreat, highlighted by soaring cathedral ceilings, a spacious en-suite bath, and the rare advantage of two walk-in closets. Each additional bedroom offers impressive dimensions, providing the kind of space that’s increasingly difficult to find in newer construction. The real showstopper awaits outdoors. Enjoy your own private backyard oasis featuring full vinyl fencing, a generous covered lanai, and a screened pool built for year-round enjoyment. Whether you’re hosting weekend gatherings, creating memorable family moments, or simply unwinding in your own peaceful setting, this outdoor space delivers the Florida lifestyle buyers dream about. This property has been meticulously maintained, reflecting pride of ownership throughout and offering peace of mind for its next owner. Opportunities to secure a move-in-ready pool home with this combination of condition, space, and location are becoming increasingly scarce. Positioned just minutes from major shopping, dining, schools, and commuter routes, this property also presents strong long-term value and investment appeal. This home will not last long in the market. Schedule your private showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,302
Status:
NEW LISTING
MLS#:
O6387742
Type:
Single Family
Subdivision:
Harmony On Lake Eloise Phase 4
Lot size:
0.13 Acres
Year built:
2026
A broker reciprocity listing Courtesy: DR HORTON REALTY OF CENTRAL FLORIDA LLC 407-250-7299
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ADDITIONAL INFORMATION

Under Construction. Welcome to Harmony at Lake Eloise, a new home community in Winter Haven. This community is currently offering 14 floorplans that range from single-story to two-story with 3 to 5 bedrooms, up to 3 bathrooms, and 2-3 car garages. Step inside and be greeted by an open floorplan meant for modern living. In the kitchen, you'll find shaker-style cabinets for that elegant touch, along with stainless-steel Whirlpool appliances including a cooktop, oven, and dishwasher. The house's exterior has block-on-block construction, architectural shingles, and stucco for a stylish and durable finish. Inside, smart home technology has been thoughtfully integrated, offering convenience and safety at your fingertips Homes in this neighborhood also come equipped with smart home technology, allowing you to easily control various aspects of your home. Whether it's adjusting the temperature or turning on the lights, convenience is at your fingertips. Living in Harmony at Lake Eloise, you'll enjoy access to all nearby amenities, including the chain of lakes, shopping centers, and golf courses. The convenient location also gives you easy access to major highways, so your commute is a breeze. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Beds:
5
Baths:
3.00
Sq.Ft.:
2,470
Status:
NEW LISTING
MLS#:
TB8482823
Type:
Single Family
Subdivision:
Villa Mar
Lot size:
0.1 Acres
Year built:
2025
A broker reciprocity listing Courtesy: CASA FRESCA REALTY 813-343-4383
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Under Construction. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,077
Status:
NEW LISTING
MLS#:
O6384870
Type:
Single Family
Subdivision:
Harmony On Lake Eloise
Lot size:
0.14 Acres
Year built:
2026
A broker reciprocity listing Courtesy: DR HORTON REALTY OF CENTRAL FLORIDA LLC 407-250-7299
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ADDITIONAL INFORMATION

Under Construction. Welcome to the Lakeside, one of our one-story floorplans featured in our Harmony at Lake Eloise community in Winter Haven, Florida. Take your pick between two artfully designed exteriors. Inside this beautiful 5 bedroom, 3 bathroom home, you'll find 2,077 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space perfect for everyday living and entertaining. The kitchen features modern cabinets, quartz countertops, and sleek stainless-steel appliances, which are sure to both turn heads and make meal prep easy. You'll never be too far from the action with the living and dining area right there. Find luxury vinyl plank flooring throughout a majority of the home including the family room, primary bedroom, kitchen, bathrooms, laundry and foyer. Bedrooms 2,3,4 and 5 will have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Privacy is guaranteed with a separate door for the toilet and shower. Contact us today and find your home at Harmony at Lake Eloise. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Beds:
2
Baths:
2.00
Sq.Ft.:
840
Status:
NEW LISTING
MLS#:
L4959920
Type:
Single Family
Subdivision:
Winter Haven Harbour Apts Condo
Lot size:
0.01 Acres
Year built:
1964
A broker reciprocity listing Courtesy: HARPER REALTY FL, LLC 863-687-8020
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ADDITIONAL INFORMATION

Discover your serene retreat at Winter Haven Harbour Condos—a charming 55+ community featuring this delightful third-floor, two-bedroom, one-and-a-half-bath residence. Recently refreshed 3 years ago with a brand-new roof, fresh paint, and plush new carpeting in both bedrooms and the living space, this home is move-in ready. The kitchen is bright and functional, with plenty of cabinetry that extends into the dining area and ceramic tile flows seamlessly through the kitchen and baths. Enjoy a screened front porch, perfect for morning coffee. The community offers a large heated pool, a clubhouse, shuffleboard, and a grilling area—ideal for gatherings. Conveniently located near shopping, medical centers, and with easy access to both Tampa and Orlando, this is a rare opportunity. Schedule your private tour today!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,464
Status:
NEW LISTING
MLS#:
P4938027
Type:
Single Family
Subdivision:
Revised Map Of Fernwood Add
Lot size:
0.27 Acres
Year built:
1936
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY SMART 1 863-508-3000
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ADDITIONAL INFORMATION

Located in the heart of Winter Haven, this property offers a great opportunity to own in a convenient and well-established area of Polk County. Situated on Ave B NE, the home is just minutes from downtown Winter Haven, local shops, restaurants, parks, and the city’s beautiful chain of lakes. The property provides easy access to major roads, making commuting simple while still enjoying a quiet residential setting. Whether you’re a first-time buyer, investor, or looking for a centrally located property, this location offers both convenience and potential. Enjoy being close to schools, grocery stores, medical facilities, and popular attractions, including nearby lakes and recreational areas that make Winter Haven known as the Chain of Lakes City. A solid opportunity in a growing Central Florida market.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,526
Status:
NEW LISTING
MLS#:
L4959890
Type:
Other
Subdivision:
Cypresswood Enclave Ph 01
Lot size:
0.05 Acres
Year built:
1995
A broker reciprocity listing Courtesy: LOCKHART & ASSOCIATES INC 863-293-1234
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ADDITIONAL INFORMATION

New to the market is this "one owner" villa located in the sought-after Enclave neighborhood located in Cypresswood Golf and Country Club in SE Winter Haven. This 3 bedroom 2 bathroom end unit is in the midst of a professional interior paint job. (new photos will be loaded after painting is complete) Enjoy Easterly pasture views from the lanai. Ideal for sunrise viewing. The country club amenities include access to the clubhouse with bar and grill, jr. olympic swimming pool and soon to be completed pickleball courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix is opening a brand new location just a mile down the road which is sure to attract other needed businesses.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,073
Status:
NEW LISTING
MLS#:
O6387453
Type:
Condo
Subdivision:
Winter Ridge Condo
Lot size:
0.03 Acres
Year built:
2000
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

Welcome to 350 Winter Ridge Blvd, Winter Haven, FL 33881 — a beautifully updated 2-bedroom, 2-bath condo offering 1,073 SQFT of comfortable living with a STUNNING WATER VIEW that truly shines when the sun is out. This move-in-ready gem features MODERN VINYL FLOORING and FRESH INTERIOR PAINT completed just over a year ago, a NEW ROOF in 2025, and a NEWER WATER HEATER replaced within the last three years for added peace of mind. Enjoy relaxing in the SCREENED-IN COVERED PATIO, the perfect spot to take in the peaceful water views and FLORIDA SUNSHINE. Ideal for a first-time homebuyer or a SEASONAL SNOW BIRD RETREAT the property also includes two parking spaces (one covered carport), a VERY LOW HOA, and community amenities such as a pool and access to Lake Smart. Conveniently located just minutes from Downtown Winter Haven, shopping, dining, and entertainment, this home offers the perfect blend of comfort, value, and location.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,846
Status:
NEW LISTING
MLS#:
L4959598
Type:
Single Family
Subdivision:
Coventry Cove Ph Ii
Lot size:
0.17 Acres
Year built:
2020
A broker reciprocity listing Courtesy: LA ROSA REALTY PRESTIGE 863-940-4850
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ADDITIONAL INFORMATION

This home delivers the perfect blend of comfort and style with an open concept design and thoughtfully defined spaces. The heart of the home is the kitchen featuring plenty of cabinetry and counter space that connects seamlessly to the dining and living areas. Large windows fill the home with natural light creating an airy feel throughout. The primary suite offers a spacious layout and ensuite bath. Additional bedrooms provide flexibility for guests, a home office, or growing needs. Enjoy outdoor living in the backyard with room to personalize and make it your own.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,143
Status:
NEW LISTING
MLS#:
P4938016
Type:
Single Family
Subdivision:
Whisper Lake 01
Lot size:
0.14 Acres
Year built:
1986
A broker reciprocity listing Courtesy: STAR REALTY OF WINTER HAVEN 863-299-7827
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ADDITIONAL INFORMATION

Imagine coming home to peaceful cul-de-sac living, easy-care tile floors, and a refreshed kitchen ready for everyday life — welcome to your next chapter! Step inside to the living room featuring subtle vaulted ceilings and a decorative fireplace. The kitchen has been tastefully refreshed within the past year with newer cabinetry, countertops, and appliances, creating a functional space for everyday cooking and entertaining. It flows seamlessly into the dedicated dining area with sliding glass doors leading to the 17x8 screened-in lanai — perfect for enjoying Florida evenings. Just outside, an additional open concrete slab provides the ideal grilling or outdoor seating area. The primary bedroom features two closets and a private en-suite bath complete with a tub/shower combination and extended vanity. A long foyer off the garage leads to the second bedroom and guest bath. The third bedroom, located off the living room with French doors, provides flexible space ideal for a home office, den, or additional bedroom. Additional highlights include washer/dryer hookup in the garage and a convenient location just off Recker Highway with quick access to the Polk Parkway, making commutes to Lakeland, Tampa, or Orlando a breeze. Whether you're a first-time buyer, downsizing, or investing — this one checks the boxes for location, layout, and value!

Beds:
2
Baths:
1.00
Sq.Ft.:
768
Status:
NEW LISTING
MLS#:
L4959885
Type:
Single Family
Subdivision:
Westwood Sub
Lot size:
0.23 Acres
Year built:
1949
A broker reciprocity listing Courtesy: BHHS FLORIDA PROPERTIES GROUP 863-701-2350
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ADDITIONAL INFORMATION

Affordable 2-bedroom, 1-bath home with a spacious yard and excellent potential! This property offers a functional layout with a comfortable living area, dedicated kitchen and dining space, and well-sized bedrooms. The large fenced backyard provides plenty of room for outdoor activities, pets, gardening, or future improvements. Mature trees offer shade and added privacy. Additional storage sheds are located in the backyard for extra convenience. Solar panels are already installed, offering potential energy savings. No HOA. Whether you’re a first-time buyer, investor, or someone looking for an affordable property with room to add value, this home presents a great opportunity at $104,900. Schedule your showing today.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,682
Status:
NEW LISTING
MLS#:
L4959887
Type:
Other
Subdivision:
Cypresswood Golf Villas
Lot size:
0.05 Acres
Year built:
1990
A broker reciprocity listing Courtesy: CROSBY & ASSOCIATES, INC. 863-293-5600
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ADDITIONAL INFORMATION

Welcome to 2813 Wingfoot Court in the sought-after Cypresswood Golf Villas! Perfectly positioned along the 8th fairway of Cypresswood Golf & Country Club, this guard-gated community offers peaceful golf course views and a relaxed Florida lifestyle.This beautifully maintained 2-bedroom, 2-bathroom villa is being sold fully furnished and truly turn-key — just bring your suitcase. The professionally designed interior gives the home a polished, cohesive feel that stands out from the moment you walk in. Vaulted ceilings highlight the spacious living and dining areas, creating a light and airy atmosphere. The kitchen features updated appliances, including a newer stove and microwave. With exception of the guest room, all windows throughout the home have been updated for improved efficiency and style. A tankless hot water heater adds modern convenience and energy savings. The primary suite offers a generous walk-in closet and private bath, while the guest bedroom also includes a walk-in closet and easy access to the second full bathroom — ideal for visitors. One of the standout features is the beautiful Florida room, perfect for morning coffee or evening relaxation. Step outside to enjoy the stained and stamped patio overlooking the fairway — a wonderful space for entertaining or simply soaking in the view. Major updates include a roof replacement in 2019 and a new A/C system in 2018, offering peace of mind. Covered parking adds everyday convenience. Residents enjoy access to community amenities including a pool, tennis courts, clubhouse, and on-site restaurant, all within minutes of shopping, dining, and major roadways. Whether you're looking for a full-time residence or a seasonal retreat, 2813 Wingfoot Court delivers comfort, style, and effortless golf course living.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,602
Status:
NEW LISTING
MLS#:
B4902197
Type:
Single Family
Subdivision:
Cypress Wood
Lot size:
0.05 Acres
Year built:
1987
A broker reciprocity listing Courtesy: FAITH AND FAMILY REALTY LLC 863-712-1991
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ADDITIONAL INFORMATION

Fully Renovated Golf Course Home – Perfect for Full or Part-Time Living Located directly on the golf course in Cypress Woods Golf & Country Club, this beautifully renovated home is a 2 bedroom, 2-bath home with an optional 3rd bedroom or sunroom. Home showcases quality craftsmanship and modern upgrades throughout — ideal for both full-time residents and seasonal owners. The open floor plan features updated flooring, designer lighting, and a completely remodeled kitchen with premium cabinetry, Corian countertops, stainless-steel appliances, new hot water heater and air conditioning system. Both bathrooms have been tastefully renovated with stylish, high-end finishes. The spacious primary suite offers a beautifully updated en-suite bath and its own private porch, creating a peaceful retreat. Positioned on the golf course, the home enjoys a prime setting within this desirable Central Florida community. Community amenities include championship golf, clubhouse dining, fitness center, and a resort-style pool. This move-in ready home offers comfort, quality, and convenience in a highly sought-after location.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,118
Status:
NEW LISTING
MLS#:
L4959863
Type:
Single Family
Subdivision:
Terranova Ph 01
Lot size:
0.17 Acres
Year built:
2003
A broker reciprocity listing Courtesy: LOCKHART & ASSOCIATES INC 863-293-1234
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ADDITIONAL INFORMATION

POOL Home on Pond in TERRANOVA! Located in desirable southeast Winter Haven, this home has it all! Large areas overlooking screened pool and pond frontage and views! Enjoy the security of a gated community close to schools, shopping, churches and LEGOLAND! Call for your private showing today!

Beds:
2
Baths:
2.00
Sq.Ft.:
792
Status:
NEW LISTING
MLS#:
S5143953
Type:
Manufactured Home
Subdivision:
Carefree Rv Country Club
Lot size:
0.07 Acres
Year built:
1986
A broker reciprocity listing Courtesy: THREE MOUNTAINS REALTY 407-674-0220
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ADDITIONAL INFORMATION

Welcome to Carefree Country Club - one of Winter Haven't best kept secrets! Tucked away off of Cypress Gardens Boulevard, when you approach the GATED community, you know you're entering a really special place. Driving through, you're encompassed by the community's 9-hole golf course. Continuing on, you'll pass a stunning two-story clubhouse, plus all of the amenities (large thermal heated swimming pool; bocce ball courts; tennis and pickle ball courts; boat docks and boat launch). And finally, you'll pass by Lake Bess, which the community has over 3,000 private feet of shoreline on! This home sits just a few homes up from the lake, and there is no need to worry about flooding, as the home pitches down toward the lake! Believe it or not, this is actually a single wide home with a large addition! Entering through the sliding glass doors, you'll find yourself in the open living space, where the kitchen, dining area, and living room flow together. You get great views of the lake through the windows as well! The original structure also has a guest bathroom (with a shower / tub combo) and guest bedroom. The addition has the primary suite, with a nice sized closet, and ensuite bathroom with a walk-in shower. In here you will also find the washer. Out back is a storage shed that can fit a golf cart (as you will see one currently in there), as well as the dryer. The home was re-piped, so no need to worry about polybutylene (grey) pipes! The monthly fees include the following: lawn care; internet access in the clubhouse and golf center; garbage disposal and recycling; all of the amenities! This is a great home in a great community; schedule your showing today!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,488
Status:
NEW LISTING
MLS#:
P4938000
Type:
Single Family
Subdivision:
Heather Glen Ph 02
Lot size:
0.18 Acres
Year built:
2001
A broker reciprocity listing Courtesy: THE HOME COMPANY 863-268-8157
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ADDITIONAL INFORMATION

Welcome to 511 Heather Glen Drive. This beautifully maintained home is in move in ready condition. Offering 4 bedrooms and 2 bathrooms, the home has new interior and exterior paint. This is a split floor plan with a large family room looking out to the screened in patio. Off the kitchen is a dinette. The guest bathroom has been remodeled. Both bathrooms have new toilets. The A/C is brand new with a HALO system that purifies the air in the house. The roof is 9 years old. There is an inside laundry room leading out to the garage. Riding lawnmower is included! The home is centrally located close to Legoland, dining, shopping and major highways and in between Orlando and Tampa. This home shows pride of ownership! Make your appointment today!

Open House:

Saturday, 3/7 12:00-2:00PM

More Open House Info >

Beds:
3
Baths:
2.00
Sq.Ft.:
1,111
Status:
NEW LISTING
MLS#:
O6386616
Type:
Single Family
Subdivision:
Jan Phyl Village #1
Lot size:
0.38 Acres
Year built:
1962
A broker reciprocity listing Courtesy: REAL BROKER, LLC 855-450-0442
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ADDITIONAL INFORMATION

NEW AC (2025), NEW INTERIOR & EXTERIOR PAINT (2026), ROOF ONLY 6-7 YEARS, LARGE CORNER LOT, ATTACHED 2 CAR AND CAR PORT GARAGE........a beautifully updated 3 bedroom, 1.5 bath home positioned on a spacious corner lot with room to breathe. This home has already had the big-ticket items handled. The roof is less than 6-7 years old and the AC unit is brand new, giving you peace of mind from day one. Even better, the home features brand new interior and exterior paint, giving it a fresh, clean, move-in-ready feel from the moment you arrive. Inside, you’ll find updated tile countertops, modern appliances, and a layout designed for comfortable everyday living. The kitchen offers durability and style, while the freshly painted interior brightens the entire home and creates a crisp, updated atmosphere. Outside is where this property truly shines. Covered and enclose lanai, Sitting on a large corner lot, you get added privacy, extra yard space, and flexibility for entertaining, storage, or future possibilities. The brand new exterior paint adds curb appeal and a polished first impression. Parking and storage will never be an issue with: • Attached 2-car garage • Additional 2-car carport • Large corner lot • Roof less than 6 years old • Brand new AC Whether you're a first-time buyer, downsizing, or looking for a solid investment in a growing Winter Haven location, this home checks all the boxes. Schedule your private showing today. (One or more photos is virtually staged)

Beds:
3
Baths:
3.00
Sq.Ft.:
1,848
Status:
NEW LISTING
MLS#:
W7883481
Type:
Single Family
Subdivision:
Villa Mar
Lot size:
0.1 Acres
Year built:
2025
A broker reciprocity listing Courtesy: MALTBIE REALTY GROUP 813-819-5255
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ADDITIONAL INFORMATION

Quick Move-in! Introducing Villa Mar in Winter Haven, Florida. Master-planned amenities including a pool with cabana that is walking distance from your home, a playground, and shaded seating area. Highway 27, less than 10 minutes away, has everything you are looking for. Grocery stores, movie theaters, shopping centers, golf courses, restaurants, and so much more. The Glen Ridge single-family home is your key to great living. An open floor plan makes entertaining a breeze. Play a game in the family room or gather round the dining room table for a delicious meal, home cooked in the gorgeous gourmet kitchen with large island and walk-in pantry. The 2-car garage offers convenient extra storage. Upstairs, 2 bedrooms and a full bath give guests plenty of privacy. Make the most of your loft by using it as a second living space or media center. Your luxury owner’s suite includes dual walk-in closets and double vanities. You’re going to love The Glen Ridge. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

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Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Use of search facilities of data on the site, other than a consumer looking to purchase real estate, is prohibited. © 2026 MIAMI Association of REALTORS®, all rights reserved.


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


Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of {{last updated}}. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Copyright 2026, My Florida Regional MLS DBA Stellar MLS.



Winter Haven Real Estate

Winter Haven is located in Florida. Winter Haven, Florida has a population of 48,707. Winter Haven is less family-centric than the surrounding county with 26.09% 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 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 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

    $271,501
    25.4%
    change since last quarter
  • # Active listings

    919
    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
Eagle Lake Elementary School PK - 05 473 15.8 33839
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
Highland City Elementary School PK - 05 428 13.8 33846
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
Pinewood Elementary School PK - 05 678 14.7 33839
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
Denison Middle School 06 - 08 842 15.9 33880
Jewett Middle Academy Magnet 06 - 08 606 18.4 33881
Westwood Middle School 06 - 08 821 15.5 33881

High Schools near Winter Haven, FL

Grades Students P/T Ratio ZIP
Chain of Lakes Collegiate High School 11 - 12 291 32.3 33881
Lake Region High School 09 - 12 1,892 19.9 33839
New Beginnings High School 07 - 12 382 27.3 33881
Polk State College Collegiate High School 11 - 12 281 40.1 33881
Winter Haven Senior High School 09 - 12 1,953 22.2 33880

Ungraded Schools near Winter Haven, FL

Grades Students P/T Ratio ZIP
Ridge Teen Parent Program 06 - 12 71 33881
Winter Haven Pace 01 - 12 5 33880

Demographics near Winter Haven, FL

City County
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