Winter Haven Single Family Homes For Sale - 806 homes

Remarks: Short Sale. Over a half-acre fenced in lot with a 4 bedroom 2 1/2 bath home with an office or den. Large family room with a separate formal dining room. Eat in kitchen with 2 pantry's. New roof in 2017-2018 and a new air conditioner in 2019. Great location minutes from State Road 60 and close to all the dining and theme parks and spring baseball field in Winter Haven.

Listing is courtesy of: BROOKS REALTY GROUP LLC (813-653-7291)

Listing Agent: Erica Ranson (863-934-3510)

Remarks: Welcome to your next chapter in beautiful Winter Haven! This charming home offers the perfect blend of comfort, convenience, and value—an ideal opportunity whether you're a first-time buyer, downsizing, or looking to invest. Step inside to discover a bright and inviting layout designed for everyday living. The home features well-proportioned living spaces filled with natural light, creating a warm and welcoming atmosphere from the moment you walk in. The kitchen offers ample cabinet space and functionality, perfect for both casual meals and entertaining guests. Enjoy relaxing mornings or peaceful evenings in your private outdoor space, with room to personalize and make it your own. Nestled in a desirable location, this property provides easy access to shopping, dining, schools, and major roadways—making your daily commute and errands a breeze. Offered at just $210,000, this is an incredible opportunity to own a home in a growing and sought-after area of Winter Haven. Don’t miss your chance to make this property yours—schedule your private showing today!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Belkis Garcia (407-994-5885)

Remarks: "Welcome to this charming 3-bedroom, 3-full-bath home nestled in the heart of Winter Haven! One of the bedrooms features a private entrance, making it perfect as an IN-LAW SUITE, home office/studio, or an income-producing rental opportunity. The spacious Florida room with screen enclosure is ideal for relaxing and entertaining, while the front screened porch adds extra curb appeal and a cozy outdoor living space. The generous backyard offers endless possibilities, plenty of room to add a pool, create your dream outdoor oasis, or simply enjoy the open space. A storage shed with electricity in the back provides additional convenience and storage. Enjoy pure, clean water throughout the entire home with a whole-house reverse osmosis filtration system. Located on a quiet dead-end street with no through traffic. No HOA, No CDD, low taxes, public water and sewer. Just minutes from Downtown Winter Haven, shopping, restaurants, and the beautiful Winter Haven Chain of Lakes. This home has so much to offer, don't miss this opportunity! Equal Housing Opportunity."

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Romina Peragine, Pllc (407-288-4595)

Remarks: Located in the desirable Harrington subdivision of Winter Haven, this beautifully single-family home offers the perfect blend of comfort, style, and value. Featuring 3 spacious bedrooms and 1 bathroom, the home showcases a bright open-concept layout ideal for modern living. The kitchen boasts granite countertops, stainless steel appliances, and ample cabinet space. Enjoy durable vinyl plank flooring throughout, generously sized bedrooms, and an abundance of natural light. Step outside to a large backyard, perfect for entertaining or relaxing. Conveniently situated near schools, parks, hospitals, dining, and entertainment. Priced to sell, schedule your showing today!

Listing is courtesy of: PREMIUM PROPERTIES R.E. SERVICE (407-380-2800)

Listing Agent: Hamid Dghirni (407-575-2891)

Remarks: Under contract-accepting backup offers. Under Construction. UNDER CONSTRUCTION:Welcome to the Residences at Winter Haven, a new single-family community focused on high-quality construction and modern design. This Key West model features a spacious three-bedroom, two-bathroom layout, centered around an open-concept living area. The interior is highlighted by premium finishes, including vinyl flooring and kitchen island with a fullwaterfall countertop. Large glass sliders lead out to a covered lanai, extending the living space and emphasizing a bright and functional environment.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Rodrigo Gomes De Almeida (407-837-8173)

Remarks: Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this immaculately maintained 3-bedroom, 2-bath home awaits. From the stone on the front elevation and bronze screened front entry to the 32’ x 18’ bronze screened veranda, the home impresses in every way. It is situated on a quiet cul-de-sac with views of a large pond and golf course in the distance. Step inside and you’ll immediately notice how clean, crisp, and welcoming the home feels, offering the perfect setting for both comfortable, relaxed living and gracious entertaining. Tasteful 18” x 18” tile flooring provides a uniform flow throughout the house. Plantation shutters adorn all windows. Six interior and 2 exterior veranda fans (total of 8 fans) are remote controlled, high-end Minka ceiling fans. The living room is accented by a coffered ceiling. The kitchen is highlighted by maple cabinets in Toffee color, and feature rollout trays, a corner lazy-susan, refrigerator cabinet and bump ups and bump outs. Identical cabinets and granite counters are found in both baths. The chef’s kitchen appliances are fingerprint resistant stainless steel. A large walk-in pantry offers ample storage space off the kitchen. Multiple pocket doors afford smooth flow room to room. The granite kitchen counters are accented with pendant lighting above the island. Identical cabinets with granite counter and desk/work area are located in the laundry room. Tranquil views from the living room, kitchen and expanded veranda are stunning. The master bath provides dual vanities, one with makeup station, and a spacious, glass-enclosed shower with custom fixtures. The garage features parking for two vehicles and a separate golf cart garage. In addition to the Green Home features built into the house, extra insulation was blown in the attic, providing added energy savings. Plus, the CDD DEBT IS PAID IN FULL on this property, saving you over $10,000! With so many outstanding features, this property must be seen in person to be appreciated. Beyond your doorstep, Lake Ashton’s unmatched amenities invite you to enjoy two championship 18-hole golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, theater, pickleball courts, bowling alley, on-site restaurant, and so much more, ensuring an active and fulfilling lifestyle. This special property is the perfect blend of comfort, convenience, and community—schedule your private showing today and experience the very best of Florida living.

Listing is courtesy of: GLOBAL LIFESTYLE LLC (727-455-2709)

Listing Agent: Brad Kirwan (863-280-0390)

Remarks: Welcome to this refined sanctuary where timeless elegance meets Florida’s tranquil landscape. On a premium golf-adjacent lot within the guarded, gated community, 2964 Plantation Road blends gracious scale, luminous living and multi-generational flexibility in one seamless layout. Upon arrival, you are greeted by mature landscaping, a circular drive and side-entry access to a three-car garage, with stunning views of golf course fairways and water views. Enter inside to discover over 3,600 square feet of thoughtfully designed space. Formal living and dining rooms flow with grace and purpose, while a custom wet bar offers effortless entertaining. The split floor plan is crafted for privacy and connection. The primary suite is complete with dual vanities, walk-in closets, a garden tub, separate shower and private pool access. On opposite wing rests an en-suite bedroom, complete with full bath and independent access. Ideal for multigenerational living, guest privacy or an upscale in-law suite. Two additional bedrooms share a dual bath, while a half bath serves daily living or poolside use. Gourmet gathering begins in the kitchen, including a center island with gas range, generous counter space and views out toward the lanai. The breakfast nook offers a comfortable space for everyday dining, complemented by a nearby utility room and a flexible bonus room. Going outside, this home’s soul lives in its outdoor realm. A pool and spa, and a summer kitchen complete with built-in grill, sink and prep station, invite all-day alfresco living. A covered lanai frames those golf and pond vistas beautifully, offering shade and breeze for lounging or entertaining. Cypresswood is a full-amenity, guard-gated community with an 18-hole golf course, clubhouse with restaurant and lounge, tennis and pickleball, fitness/wellness center, and social programming. A $10,000 seller concession and one-year home warranty.

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-480-5014)

Listing Agent: Audrey Christman (516-547-5343)

Remarks: "OWNER WILL CREDIT UP TO $15,000 FOR THE COST OF ROOF REPLACEMENT AT CLOSING" FOR SALE: Attractive 3-Bedroom, 2-Bathroom Single-Family Home in Winter Haven! Discover your dream home in Osprey Pointe, where comfort meets style. This home is designed for modern living and entertaining. An open floor plan connects the eat-in kitchen and breakfast bar seamlessly to the living and dining areas, perfect for gatherings. Equipped kitchen with an eat-in area and a breakfast bar, ready for family meals and casual dining. Luxurious Master Suite: Retreat to your sanctuary featuring an elegant tray ceiling, a generous walk-in closet, double vanities in the primary bathroom, and a large glass shower stall. Enjoy the Florida lifestyle on your covered and screened rear porch. A paver driveway and an attached 2-car garage add to the curb appeal. The home includes inside laundry with washer and dryer hook-ups. Tiled common areas and bathrooms offer easy maintenance, while plush carpet in the bedrooms provides comfort. Exceptional Community Amenities: Live like you're on vacation every day! Enjoy access to a community clubhouse and a sparkling pool. Plus, take advantage of the private waterfront dock on beautiful Lake Ned for fishing and recreational activities. Lawncare included in HOA. Don't miss this opportunity to own a piece of paradise in Winter Haven. Schedule your showing today!

Listing is courtesy of: FLORIDA REALTY RESULTS LLC (407-498-3838)

Listing Agent: Debbie Browning (407-908-9060)

Remarks: Under contract-accepting backup offers. Welcome to 3108 Buckeye Point Dr — where comfort meets convenience in the heart of Winter Haven. From the moment you arrive, this home invites you in with a layout designed for the way you truly live. With 4 bedrooms and 2 full bath and a brand new A/C system the living spaces feel open yet connected, creating an easy flow for both everyday routines and weekend gatherings. Natural light enhances the home’s warmth, while thoughtful design elements make each space feel intentional and livable. The kitchen serves as the hub of the home, seamlessly connecting to the main living areas — ideal for hosting, relaxing, or simply enjoying a quiet night in. The primary suite offers a private retreat, while additional rooms provide flexibility for guests, work-from-home needs, or hobbies. Step outside and imagine morning coffee, evening unwinding, and effortless Florida living in your own outdoor space. Located in a desirable Winter Haven community, you’ll appreciate the convenience to shopping, dining, medical facilities, schools, and major roadways — all while enjoying the feel of a tucked-away neighborhood setting. Homes that combine layout, location, and livability like this don’t stay available for long. Schedule your private showing and experience 3108 Buckeye Point Dr for yourself.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Jp Phillips (863-670-7923)

Remarks: Welcome to this immaculately maintained 4-bedroom, 3-bathroom home with a spacious 3-car garage, perfectly situated in the highly desirable Country Club area of Northeast Winter Haven. Located within a gated community, this home offers both privacy and peace of mind. Backing up to an 11-acre jurisdictional wetland, the property provides complete rear privacy with a beautiful natural landscape—no rear neighbors, just serene views and tranquil surroundings. Inside, you’ll find a thoughtfully designed split floor plan with upgraded flooring, modern cabinetry, and stylish countertops throughout. The layout offers both functionality and comfort, ideal for those who love to entertain. Step outside to your private screened back porch retreat and fully fenced yard—perfect for relaxing evenings or weekend gatherings while enjoying the quiet, natural backdrop. This home truly combines luxury, privacy, and location—don’t miss the opportunity to make it yours.

Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)

Listing Agent: Joshua Taylor (863-651-5471)

Remarks: Move-in ready, this charming 3-bedroom, 1-bath block home sits on a spacious lot with no rear neighbors, offering added privacy and peaceful surroundings. Inside, you’ll find updated flooring in the bedrooms and bathroom, creating a fresh and inviting feel. The home also features two versatile bonus rooms—perfect for a home office, in-law space, or even a possible 4th bedroom to suit your needs. Enjoy Florida living at its best with a screened lanai off the back, ideal for relaxing in the sunshine or entertaining guests year-round. With its flexible layout and generous outdoor space, this property offers both comfort and opportunity. Whether you're a first-time buyer or looking to expand, this home is ready for you to move right in and make it your own!

Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)

Listing Agent: Anne Halbert (402-460-1352)

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. 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. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails.  Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. 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. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails.  Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: **Location, Location, Location! Seller offering $10,000 toward buyer closing costs, prepaid items, or interest rate buy-down with acceptable offer!** Beautifully maintained 3-bedroom, 2-bath home situated on an expansive oversized corner lot in desirable Southeast Winter Haven with **no city taxes — county taxes only**. Major updates have already been completed, including a **2024 A/C**, **2019 roof**, **new drain field**, and recent **septic inspection/pump-out** for added peace of mind. Inside, you'll find luxury laminate flooring throughout the main living areas with ceramic tile in wet areas, creating a clean and modern feel. Enjoy outdoor living in the private rear courtyard shaded by mature landscaping and beautiful trees, plus a stunning oak tree that enhances the curb appeal of this spacious corner homesite. A rare bonus is the **704 sq. ft. detached garage/workshop**, offering endless possibilities for storage, hobbies, vehicles, or workspace. Conveniently located near shopping, dining, schools, **only 2.1 miles from LEGOLAND Florida Resort**, close to Chain of Lakes access, near Freedom Boat Club, and just minutes from the new Chain of Lakes Baseball Complex. Don’t miss this opportunity!

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: John Calhoun (863-528-7973)

Remarks: Spacious single-family home featuring 4 bedrooms and 2.5 bathrooms with approximately 3,160 sq ft of living space, offering a functional and flexible floor plan. The main level includes a private office with French doors, ideal for use as a home office or optional fifth bedroom. Generous interior spaces provide comfortable living and well-sized bedrooms throughout. Conveniently located in Winter Haven, with easy access to major roads, shopping, dining, and everyday conveniences. This property offers an excellent opportunity for buyers seeking space, versatility, and a well-established residential setting.

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Maria Chavez (407-866-4682)

Remarks: Welcome to your dream home in the heart of Winter Haven's sought-after Peace Creek Reserve community! This stunning two-story Atlanta Plan offers 4 bedrooms, 2.5 bathrooms, and 1,933 square feet of thoughtfully designed living space that perfectly balances comfort with style with custom built-in blinds, custom closets in bedrooms & designer touches such as accent wall in living room with floating shelf that will be staying with the home! Step inside to discover an open floor plan that flows seamlessly from the great room to the dining area and into a chef's dream kitchen. The heart of the home features a large island perfect for morning coffee or evening entertaining, complemented by gleaming quartz countertops, stainless steel appliances, and a generous pantry. The casual dining area opens to a covered lanai through sliding glass doors, creating an effortless indoor-outdoor living experience. Yard is fenced in with built in gazebo and kids playground that are staying with the home! Upstairs, the primary bedroom retreat awaits with a luxurious en-suite bathroom featuring a spacious walk-in shower, dual vanity, and a walk-in closet that could double as a small boutique. Three additional bedrooms, a full bathroom, and a versatile loft provide plenty of space for family, guests, or that home office you've been dreaming about. The convenient second-floor laundry room means no more hauling baskets up and down stairs. Throughout the home, beautiful tile flooring graces the main living areas while cozy carpet warms the bedrooms. Peace Creek Reserve offers the perfect blend of small-town charm and modern convenience, nestled near Winter Haven's famous chain of lakes connected by scenic canals. With abundant shopping, dining, and bike paths nearby, this community delivers everything you've been searching for in your next home.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Maritza Saint Hilaire (407-953-6765)

Remarks: Don't miss out on this amazing 4/3 single-family home with a pool near Lake Eloise in winter Haven! the seller has recently spent 15k upgrading the St Augustine grass, pavers in front and around the pool, gutters as well as new duct work and dryer duct clean out, tree service and more! This remarkable home features a newer roof, HVAC, Water heater, Pool screen enclosure, pool pump, Flooring, Cabinets, Paint, Pool Solar, Granite counter tops, Walk in shower, a marcite pool, Pool deck coating, new flooring in several rooms, the garage has epoxy flooring, resurfaced showers and more. This home sits on a well-manicured lot that is almost 1/2 acre in size. Seeing is believing with this home so hurry and make your appointment soon!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: John Carter (863-529-7488)

Remarks: Welcome to a move-in ready villa in the desirable 55+ Oakview community of Winter Haven—now strategically repositioned to reflect today’s market and create immediate opportunity. This well-maintained 2-bedroom, 2-bath home offers 1,220 sq ft of comfortable living with a functional open layout, spacious bedrooms with walk-in closets, and a screened lanai designed for relaxed Florida mornings and evenings. Major updates are already done for you, including a NEW ROOF (2024) and HVAC (2019), giving buyers confidence where it matters most. The kitchen has been refreshed with brand-new appliances, making this a truly easy transition with no extra projects needed. A standout feature is the garage screen system, allowing you to enjoy fresh air and added flexibility during the day—an underrated benefit for Florida living. The HOA covers lawn care and exterior maintenance, supporting a low-maintenance, lock-and-leave lifestyle many buyers are actively seeking. Now repositioned to align with current market conditions—creating one of the most compelling opportunities in Oakview today. With recent activity in the community, buyers are moving quickly when the value makes sense—schedule your showing today.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Vanessa Aybar Badillo (352-557-1682)

Remarks: Take a look at this beautifully upgraded 3-bedroom, 2-bathroom home located in the desirable gated community of Sanctuary by the Lake in Winter Haven. Nestled along the shores of Lake Rochelle part of the renowned Chain of Lakes this property offers the perfect blend of comfort, style, and serene lakeside living. Step inside to an inviting open-concept layout featuring a bright and spacious living and dining area with glass sliding doors that overlook a large, fully fenced backyard. With plenty of room to add a pool, the outdoor space is ideal for relaxation and entertaining. A double-car garage provides ample parking and additional storage. The modern kitchen is designed for both functionality and style, boasting stainless steel appliances, rich wood cabinetry, a spacious pantry, and a large island perfect for casual dining and gatherings. The primary suite serves as a private retreat, complete with an oversized walk-in closet and a luxurious en-suite bathroom featuring a walk-in tiled shower. Two additional bedrooms bring comfort and versatility for family, guests, or a home office. Residents of Sanctuary by the Lake enjoy exclusive access to Lake Rochelle for kayaking and water sports, as well as scenic walking trails, private docks, and a playground. All of this comes with low HOA fees and no CDD. Conveniently located near shopping, dining, medical centers, and major attractions including LEGOLAND®, Walt Disney World®, and Universal Studios® this home offers the best of Central Florida living.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Gaby Murillo (863-668-1914)

Remarks: One or more photo(s) has been virtually staged. Welcome to this thoughtfully designed single-story home in a growing Winter Haven community, where modern comfort meets everyday convenience. Positioned on a corner lot with clean curb appeal and a fully fenced backyard, this property offers both functionality and a polished presentation from the moment you arrive. Inside, the home opens to a bright, open-concept living space anchored by durable tile flooring and enhanced by natural light. The living room flows seamlessly into the kitchen and dining area, creating an ideal layout for both daily living and entertaining. A large center island provides additional seating and workspace, complemented by white cabinetry, sleek countertops, and stainless steel appliances for a clean, contemporary look. The layout is designed with efficiency and comfort in mind, offering a practical flow between living spaces and private areas. Finishes throughout the home reflect a well-maintained, move-in-ready condition, with neutral tones that allow for easy personalization. Step outside to a fully fenced backyard featuring a paved patio area—perfect for outdoor dining, relaxing, or creating your own backyard retreat. The yard offers a balance of usable green space and lowmaintenance design, with room to enhance further if desired. Additional features include a two-car garage, modern fixtures, and solar panels visible on the roof, which may contribute to energy efficiency. Beyond the home itself, the community offers amenities such as a resort-style pool with lounge seating, providing a convenient option for recreation without the upkeep. The neighborhood is designed with sidewalks and a cohesive feel, contributing to an organized and accessible environment. Located in Winter Haven, this property benefits from proximity to everyday essentials including grocery stores, retail centers, restaurants, and healthcare services. The area is also known for its chain of lakes, parks, and outdoor recreation opportunities. Major roadways nearby allow for convenient travel to Lakeland, Orlando, and surrounding Central Florida employment hubs. This home presents a strong combination of modern living, outdoor space, and community amenities in a well-connected location.

Listing is courtesy of: NEXTHOME MY WAY (407-544-4545)

Listing Agent: Angel Pabon (407-544-4545)