Refine Search
Sort by
$199,900
3 Beds 2 Baths Inwood SubDv. 33881 Zip Code
Virtually Staged. Welcome to 1725 31st St. NW in Winter Haven—where thoughtful updates, stylish finishes, and exceptional value come together! Offering an impressive amount of living space for the price, this beautifully renovated 3-bedroom, 1.5-bath home is the perfect opportunity for first-time buyers, downsizers, or investors looking for a move-in-ready property. Step inside to discover brand-new luxury vinyl plank flooring throughout, complemented by a fresh coat of paint inside and out, creating a bright, modern feel from the moment you enter. The fully renovated kitchen is the heart of the home, featuring new cabinetry, solid surface countertops, stainless steel appliances, and plenty of workspace for everyday living and entertaining. Additional upgrades include new doors, new ceiling fans, and modern light fixtures throughout, giving the home a polished, cohesive look. A dedicated laundry area adds convenience, while the freshly landscaped front yard provides great curb appeal and a welcoming first impression. If you're searching for a home that delivers more living space and more value than you'd expect, this Winter Haven gem is one you won't want to miss. Schedule your private showing today!

1725 31st Street Nw, Winter Haven

$274,990
3 Beds 2 Baths Leisure Shores SubDv. 33881 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bath home offering approximately 1,627 square feet of comfortable living space in the established Leisure Shores community of Winter Haven. Situated on a spacious 0.22-acre lot, this property is packed with features both inside and out. Step inside to an open floor plan with easy-to-maintain laminate flooring throughout, an updated kitchen featuring granite countertops, newer cabinetry, stainless steel appliances, and plenty of space for everyday living and entertaining. Energy-efficient double-pane windows and an updated sliding glass door help enhance comfort throughout the home. The backyard is designed for enjoying Florida living, complete with a screened lanai, an above-ground pool, a large side deck, and a fully fenced yard that’s perfect for relaxing or hosting family and friends. Need extra space? This property offers multiple detached structures, including a spacious air-conditioned shed that’s ideal for a home office, hobby room, gym, studio, or workshop, plus an additional storage shed for tools and equipment. For those with recreational vehicles or extra toys, you’ll appreciate the dedicated RV parking area with electrical hookup, along with a covered carport for everyday parking. Conveniently located near shopping, dining, schools, and everything Winter Haven has to offer, this home combines comfort, versatility, and outdoor living in one exceptional package. Schedule your private showing today!

2021 Oliver Place, Winter Haven

$150,000
2 Beds 1 Baths Inwood SubDv. 33881 Zip Code
Investor special in the heart of the Inwood neighborhood — solid block construction, new roof (2024), and a location that puts you minutes from everything Winter Haven has to give. This two-bedroom (possibly could be a 3 bedroom), one-bath home sits on a fenced lot with mature shade trees, and the covered, screened front porch gives the place a real homey feel the moment you pull up. Inside you'll find ceramic tile throughout the bedrooms and living areas, ceiling fans in every room, and a converted single-car garage that works well as an additional bedroom or possibly a den, home office, or storage space. The layout is straightforward and functional — living room, eat-in kitchen, two bedrooms with built-in closets, and a full bath with pedestal sink and tiled shower. There's also a linen closet in the hall. A shed out back adds extra storage. And the size of the backyard allows for endless possibilities. The home currently has window AC units but no central air or heat system — a definite opportunity for a buyer to update to their preference and immediately add equity. Dual septic system on site. Water is public. The property is being sold as-is. Convenient to US-17, shopping, dining, Polk State College, the Chain of Lakes trail system, and downtown Winter Haven. No HOA. Great bones, priced to move.

3319 Avenue U Nw, Winter Haven

$215,000
3 Beds 3 Baths Hartridge Landing SubDv. 33881 Zip Code
Check out this wonderful opportunity to own a spacious 3-bedroom, 2.5-bath home in the desirable 55+ community of Hartridge Landings! This well-maintained community offers a low HOA fee that includes access to the community pool and a private boat ramp on Lake Hartridge, providing access to Winter Haven's renowned Chain of Lakes. Step inside to an open and versatile floor plan featuring two expansive living areas that have endless possibilities for entertaining, relaxing, or creating a dedicated den, formal living room, or family room. The spacious first-floor primary suite serves as a private retreat, complete with an en-suite bathroom featuring dual sinks and a walk-in shower. The galley-style kitchen is conveniently located just off the dining area and offers the perfect space for a cozy breakfast nook. Also on the first floor are a half bath, a generously sized laundry room with built-in shelving, and a flexible office/bonus room with a built-in desk. Both the kitchen and office provide direct access to the private courtyard, creating a great space for outdoor relaxation or entertaining. Upstairs, you'll find two generously sized guest bedrooms and a full bathroom, providing plenty of space for family and visitors. Conveniently located near shopping, dining, medical facilities, and everyday conveniences, this home offers the perfect combination of comfort, functionality, and low-maintenance living. Schedule your private showing today!

2216 Starboard, Winter Haven

$195,000
3 Beds 2 Baths Biltmore Shores SubDv. 33881 Zip Code
BACK ON THE MARKET! No fault of the seller! Welcome to 3006 Elm Street in beautiful Winter Haven — a charming home full of potential and perfectly positioned for convenience! This 3-bedroom, 1.5-bath home also features a flexible office space that could easily serve as a 4th bedroom, playroom, hobby room, or home gym. Step inside to find new tile flooring, a remodeled bathroom, a newer roof, and updated ceilings that give the home a fresh and modern feel. The spacious kitchen offers plenty of room to cook, gather, and get creative with your dream design ideas. Outside, the backyard is a blank canvas ready for your personal touch — create the garden, outdoor kitchen, pool area, or entertaining space you've always wanted! Conveniently located near shopping, dining, attractions, and with easy access for commuting to both Tampa and Orlando, this property offers the perfect blend of comfort, opportunity, and location. Whether you're looking for your first home, investment property, or extra space to grow, this Winter Haven gem is ready to welcome you home!

3006 Elm Street, Winter Haven

$309,000
4 Beds 2 Baths St James Xing SubDv. 33881 Zip Code
This 4/2 home has a renovated interior showcasing modern upgrades throughout. The home features stunning new 36" x 24" porcelain tile flooring, offering a sleek, contemporary look with durability and easy maintenance. Move-in ready and designed for comfortable, stylish living. Dual access bedroom and bath provides the bedroom with private ensuite access while allowing the bathroom to serve as a main or guest bathroom from the hall, featuring two doors to maximize access and functionality. Large kitchen with island and lots of cabinet space and large pantry. Sliding doors leading to covered screened in porch with additional concreted tiled patio area that leads to a large backyard. Seller will consider contributing toward buyer’s closing costs.

4669 Osprey Way, Winter Haven

$75,000
Inwood SubDv. 33881 Zip Code
Great vacant lot for sale. Owner wishes to sell adjoining lot at same time. Adjoining lot is 3790 Avenue U NW. 3790 is.68/acre. Total land available is 1.11 acres. Pretty trees on both lots! No structure on property; however, a footer is present from a previous owner who started to build a house on this lot. 3790 Avenue U NW is a beautiful lakefront lot, across the street from Lake Blue. There is a public park on the actual lake frontage. The park has a boat ramp, fishing dock, picnic tables, playground and grills available. There is a great paved walking trail that runs through the park. The park will never be built on, so the lakeview is permanent. What a wonderful future homesite this could be for you! Please call agent with any questions!

3799 Avenue T Nw, Winter Haven

$425,000
3 Beds 3 Baths East View Pkwy SubDv. 33881 Zip Code
One or more photo(s) has been virtually staged. Welcome to a place where everyday life feels like a getaway. Set along the peaceful shores of Lake Jessie, part of Winter Haven’s renowned Chain of Lakes, this lakefront retreat is more than just a home, it’s a lifestyle defined by water, sunshine, & unforgettable experiences. Start your mornings with breathtaking sunrises shimmering across the lake, coffee in hand from your private dock or patio. Spend your days exactly how you choose, cruising the Chain of Lakes by boat, casting a line in some of Central Florida’s best freshwater fishing, or enjoying world-class watersports like skiing, wakeboarding and paddleboarding right from your backyard. With nearby slalom courses & open water, this is truly a paradise for water enthusiasts. Lake Jessie is especially cherished for its tranquil atmosphere, offering a rare sense of calm while still being full of life. One of its most unique features is the seaplane activity, where you can watch planes gracefully land and take off across the water, an experience that never gets old and adds to the charm of lakeside living. Nature lovers will also appreciate the frequent sightings of all kinds of birds & other beautiful wildlife. The home itself offers a thoughtfully designed single-story layout with over 1,800 square feet, featuring 3 bedrooms & 3 bathrooms. An open-concept living space is filled with natural light and showcases stunning lake views, while a split-bedroom design provides comfort & privacy. A private in-law suite with its own entrance adds flexibility for guests, multi-generational living, or additional income potential. This residence offers plenty of parking space with its oversized driveway & an additional carport providing covered parking as well. The home has been updated with modern finishes and includes a metal roof installed in 2019. This home would make a perfect full time residence, investment property or second home. Beyond the water, the location is just as appealing. You’re right around the corner from a brand new Publix store and minutes from the heart of Winter Haven, where you’ll find charming local restaurants, shops, parks, and community events. Legoland Florida Resort is just a short drive away and there is convenient access to both Tampa and Orlando, so world-class attractions, dining & entertainment are always within reach. Whether you're seeking adventure, relaxation, or a smart investment, this Lake Jessie property delivers it all, offering the rare opportunity to live, play & unwind in one of Florida’s most iconic lakefront settings. Book your showing today!

900 Lake Jessie Drive, Winter Haven

$210,000
4 Beds 3 Baths Carefree Cove SubDv. 33881 Zip Code
Short Sale. This property presents a great opportunity for buyers looking to renovate and add value. With a functional floor plan and generous living areas, it offers a solid starting point for updates and improvements. The layout provides flexibility to reimagine the space to suit your needs and design preferences. Spacious rooms allow for creative customization throughout. The kitchen area offers ample space to redesign and enhance. Bedrooms are well sized and provide potential to create comfortable retreats. There is opportunity to refresh both the interior and exterior to maximize appeal. Outdoor space allows room for landscaping or additional enhancements. Ideal for investors or buyers seeking a renovation project. Schedule your showing today and explore the possibilities.

125 Edgewater Drive, Winter Haven

$634,900
4 Beds 3 Baths Sanctuary By The Lake Ph One SubDv. 33881 Zip Code
Welcome to this exceptional custom-built 2023 luxury residence located within the gated community of Sanctuary by the Lake, where modern elegance, thoughtful design, & everyday comfort come together seamlessly. Perfectly positioned on a spacious corner lot directly across from the lake, this stunning home immediately impresses with its commanding presence & refined architectural detail. Step through the beautiful double front doors & experience an immediate sense of openness, highlighted by soaring ceilings, abundant natural light, & expansive living spaces designed to feel both grand & inviting. With over 3,600 square feet of living space, the thoughtfully designed open layout effortlessly connects formal & casual living areas, creating an ideal setting for both entertaining & relaxed daily living. At the heart of the home lies a beautifully appointed chef’s kitchen, featuring Granite countertops, upgraded Stainless-Steel appliances, a breakfast bar, walk-in pantry & a generous prep space, perfect for hosting gatherings or enjoying quiet mornings at home. The kitchen flows naturally into the impressive great room & dining areas, enhancing the home’s seamless indoor living experience. One of the standout features is the oversized covered and enclosed Florida room, custom added by the owners to extend the living space year-round. Whether hosting celebrations, entertaining guests, or simply unwinding while enjoying peaceful surroundings, this space truly elevates the lifestyle this home offers. Designed with privacy in mind, the desirable triple split floor plan includes 4 spacious bedrooms, 3 full bathrooms & a dedicated private office, ideal for remote work or flexible living needs. The luxurious primary suite serves as a private retreat, complete with dual vanities, a garden tub, separate walk-in shower, makeup vanity & a very generous walk-in closet. Beautiful luxury vinyl plank flooring flows throughout the main living areas, complemented by tasteful finishes & quality craftsmanship that reflect the home’s custom construction. A well-equipped laundry room with cabinetry, countertop workspace & sink adds everyday convenience. A 50-amp generator port was added for peace of mind. Beyond the home itself, the location offers the best of Central Florida living. Just minutes from downtown Winter Haven, residents enjoy award-winning restaurants, local boutiques, parks & year-round entertainment, while nearby access to Lakeland & I-4 provides an easy commute to both Tampa and Orlando. Florida’s Atlantic and Gulf beaches are approximately 90 minutes away, making weekend coastal escapes effortlessly accessible. This is more than a home, it is a refined living experience combining space, luxury, and lifestyle within one of Winter Haven’s most desirable gated communities.

530 Sanctuary Boulevard, Winter Haven

$257,999
4 Beds 2 Baths Inwood SubDv. 33881 Zip Code
Welcome to this spacious and recently upgraded home sitting on a rare 0.40-acre corner lot with NO HOA and NO CDD, giving you the freedom and space you’ve been looking for. Major recent improvements include updated HVAC, electrical, and plumbing systems for added peace of mind, along with attractive interior upgrades featuring modern flooring, an updated kitchen with stylish cabinetry and stainless-steel appliances, and refreshed bathrooms with contemporary tile finishes. The oversized lot offers endless possibilities and plenty of room to park your RV, boat, jet ski, work vehicles, or recreational toys worry-free — something hard to find in today’s market. Conveniently located near major supermarkets, restaurants, schools, and main roads for easy commuting, this property is ideal for homeowners seeking space and flexibility or investors looking for a strong opportunity. Schedule your private showing today and discover the value, freedom, and potential this unique property has to offer!

1701 36th Street Nw, Winter Haven

$265,000
3 Beds 1 Baths Biltmore Shores SubDv. 33881 Zip Code
This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.

3022 Hickory Street Nw, Winter Haven

$295,700
4 Beds 2 Baths Inwood SubDv. 33881 Zip Code
BACK ON MARKET — NOW PRICED UNDER $300K! Seller offering a $5,000 buyer closing cost credit. Occupied Winter Haven duplex generating $2,550/month in gross rental income. Both units are 2 bed / 1 bath and feature stone countertops, laminate flooring, and separate living spaces. No carpet. No HOA. No current vacancy. This property offers immediate income from day one with a practical two-unit setup for long-term rental demand. Located in a quiet residential area less than 2 miles from public schools, near Winter Haven’s Chain of Lakes, Lake Shipp Park, public boat ramps, trails, shopping, dining, and approximately 20 minutes from LEGOLAND Florida. Investors looking for an income-producing asset under $300K should take a serious look. Schedule your showing today.

3356 Avenue Q Nw, Winter Haven