Winter Haven Single Family Homes For Sale - 776 homes

Remarks: Virtually Staged. Welcome to 3228 Country Walk Club Cir in Winter Haven! This spacious two-story home features 5 bedrooms and 3 bathrooms, offering plenty of room for family and entertaining. The home has been updated with fresh interior paint, brand-new carpet and vinyl flooring throughout, and modern lighting fixtures. The kitchen comes equipped with new stainless steel appliances and opens to the dining and living area for a comfortable, functional layout. One bedroom is conveniently located on the first floor, with four additional bedrooms upstairs. The master suite features two walk-in closets and an updated bathroom with dual vanities and a newly tiled walk-in shower. The second upstairs bathroom also includes dual vanities for added convenience. A bonus area upstairs provides flexible space perfect for a playroom, home office, or media room, along with an upstairs laundry room for easy access. Outside, enjoy a large backyard and an attached two-car garage. Schedule your showing today! Some photos in this listing have been virtually staged to help illustrate the property’s potential. No physical changes have been made to the property.

Listing is courtesy of: PALM ISLAND REALTY (813-843-2233)

Listing Agent: James Nagy, Pa (813-843-2233)

Remarks: Take advantage of an incredible builder promotion featuring low down payment options and builder paid closing costs, rate promotions, with a low 4.25% available making homeownership more accessible than ever. Inside you'll find premium upgrades throughout, from high end finishes and designer details to an open concept layout built for both everyday living and entertaining. Why wait to build when you can move right in? This quick move in home gives you the best of both worlds brand new construction without the wait plus incentive that make it an opportunity you don't want to miss. Welcome to the Summit model in Peach Crossings a beautifully designed, brand-new home offering four bedrooms, two bathrooms, and a bright open-concept layout. High ceilings create an airy feel throughout, while the spacious living area flows seamlessly into a stylish kitchen featuring ample counter space and brand new Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave. A large hall closet adds valuable storage for everyday convenience. The owner’s suite provides a relaxing retreat with a generously sized bedroom and a private en-suite bathroom complete with dual sinks and a sleek step-in shower. The family room is perfect for entertaining or unwinding, with plenty of space for a sectional and media setup ideal for movie nights or casual gatherings. Step outside to your private lanai, perfect for enjoying Florida evenings, while the professionally landscaped front yard adds great curb appeal. Located in Polk County, Peach Crossings offers a peaceful setting with convenient access to shopping, dining, and local attractions. Residents also enjoy community amenities like a playground and picnic area, along with access to highly rated Polk County schools. With all upgrades included, this home is truly move-in ready. Schedule your private tour today!

Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)

Listing Agent: Chris Courtney (407-406-0506)

Remarks: Welcome to this inviting 3BR/2BA home with a 2-car garage and 2,128 sq. ft. in a gated Winter Haven community. Features include tile in the main living areas, carpet in the bedrooms, an open kitchen with pantry and dining area, and a primary suite with walk-in closet, dual sinks, garden tub, and separate shower. Enjoy no rear neighbors and backyard views of Lake Maude Natural Park, with convenient access to downtown Winter Haven, Polk State Diamond Plex, and the Chain of Lakes Trail.

Listing is courtesy of: OPTIMA ONE REALTY, INC. (352-243-6784)

Listing Agent: Alexis Ortiz Mendez (321-624-3951)

Remarks: Charming and inviting, this 3-bed, 2-bath home sits in a lovely Winter Haven community with a very low HOA. Built in 2015, it offers a modern design, a comfortable one-level layout, a 2-car garage, and all appliances included. Tucked into the vibrant Chain of Lakes region, you’re surrounded by peaceful views, leafy lakes, and plenty of outdoor fun from boat cruises to paddle boarding. And when it’s time for entertainment, you couldn’t be better located: you’re just 20 minutes from LEGOLAND Florida Resort, and only about 30 miles from Walt Disney World, making magical Orlando day trips effortless.

Listing is courtesy of: MARZUCCO REAL ESTATE (813-679-1365)

Listing Agent: Clarisa Moody (813-446-2003)

Remarks: Relaxed golf community living inside the gated and guarded Cypresswood Golf & Country Club. Welcome to 460 Pinehurst Ct in Winter Haven, Florida — an updated and spacious 2 bedroom, 2 bath patio home tucked away on a quiet cul-de-sac street with no through traffic. A private walled walkway leads to a charming front porch with sitting area, creating a warm and welcoming approach. Step inside the foyer to discover a clean, updated interior offering more than 1,600 square feet of comfortable living space, highlighted by beautiful new flooring, a freshly painted interior, and a long list of thoughtful improvements. All carpeting has been removed, the outdated popcorn ceilings have been scraped and refinished for a more modern look, and the overgrown landscaping has been cleared away to create a clean, attractive, and easy-to-maintain property. The roof was replaced in 2020 for added peace of mind, and gutters have also been installed for convenience and functionality. The great room design creates a spacious and open feel, accentuated by built-in shelving and large glass sliders that bring in natural light while offering the perfect space to showcase personal décor and seasonal accents. Sliding glass doors open to the enclosed, air-conditioned Florida room, seamlessly expanding the living area and creating an easy indoor-outdoor lifestyle that can be enjoyed year-round. The great room also offers space for formal dining in addition to the casual eat-in area found within the kitchen. The generously sized kitchen features abundant real wood cabinetry, a large breakfast bar, closet pantry, and an inviting dining area ideal for casual meals and everyday living. The primary suite offers comfortable dimensions, a walk-in closet, and an en-suite bath complete with a tiled walk-in shower. The guest bedroom is also nicely sized and features its own walk-in closet along with convenient access to the full guest bathroom with tub and shower. Storage is abundant throughout the home with multiple interior closets, garage storage closets, and a spacious 2-car garage with laundry connections, helping keep everything neatly organized and out of sight. Additional features include an irrigation system and low-maintenance exterior living. Beyond the home, Cypresswood delivers one of Winter Haven’s most enjoyable golf community lifestyles. Residents enjoy access to the 18-hole championship golf course, originally opened in 1969 and designed by award-winning architect Ron Garl. Known for its rolling fairways and mature landscaping, the course also features a pro shop, driving range, putting green, and dedicated short-game practice areas. Just a short stroll from the home, residents can enjoy the recently refurbished junior Olympic-sized swimming pool, tennis courts, pickleball courts, and Wellness Center. The Cypresswood Pub & Restaurant serves as the social heart of the community, offering planned events, a full bar, great food, and live weekend music in a relaxed setting overlooking the golf course. Whether you are searching for a full-time residence, winter retreat, or low-maintenance golf community home, 460 Pinehurst Ct offers an exceptional opportunity to enjoy the Florida lifestyle in one of Winter Haven’s most established gated golf communities.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Michael Stone (863-412-9733)

Remarks: This 2 BR, 2 BA home is located near Rotary Park and Kiwanis Park, which is on Lake Martha, both public parks. Each park has room for games and family gatherings. Rotary Park has a baseball field with backstop and other outside activity areas. This home is located near schools, the Winter Haven downtown post office, the Winter Haven (Bay Care Hospital) and several doctors offices and medical clinics. The Winter Haven Public Library is also 6+/- blocks to the west of this property. The home has a metal roof which offers a long life and better storm protection than typical asphalt shingles. The windows have been replaced and the central A/c - Heat system has recently been inspected. A detached storage building provides room for lawn equipment or other items not needed inside the residence, but are more easily accessed than typical attic space provides. The interior of the home has been extensively renovated with both bathrooms remodeled.

Listing is courtesy of: TOWN & COUNTRY REAL ESTATE (863-293-1141)

Listing Agent: Timothy Irby (863-206-4464)

Remarks: Welcome to your dream home in the highly desirable community of Emily Estates! This stunning, move-in-ready 4-bedroom, 2-bath,stainless steel appliances, and upgraded plumbing fixtures throughout—giving it the crisp, clean feel of a brand-new build. You will love the light and bright open-concept floor plan, which perfectly channels natural sunlight across the spacious main living areas. The kitchen is a chef's delight, boasting ample cabinet and counter space, a convenient breakfast bar, and durable ceramic tile flooring throughout for effortless maintenance. Step outside in the backyard with endless possibilities—perfect for a playground, hosting weekend BBQs, or simply relaxing in the Florida sunshine. Nestled in a fantastic, quiet neighborhood just minutes from premier shopping, dining, and the excitement of Legoland, this turnkey home offers the perfect blend of comfort and convenience. schedule your tour today!

Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-531-2006)

Listing Agent: Octavia Cheveresan (727-403-8948)

Remarks: Looking for space, character, and the opportunity to add value? This long-time family home, lovingly owned since 1973, offers over 1,600 square feet and is located in desirable Northwest Winter Haven, just one block from a public park and only minutes from a neighborhood boat ramp with access to Lake Howard and the Winter Haven Chain of Lakes. Several updates have already been completed on one side of the home, including improvements to the kitchen and main bathroom, allowing buyers to move in and enjoy while completing additional projects over time. The half bath, den, workshop, and patio area provide excellent opportunities to customize and build equity. Whether you're a homeowner with a vision or an investor seeking a property with renovation potential, this home offers flexibility and room for creativity. The spacious floor plan includes a large den with built-in shelving, a generous workshop, and a sizable patio area, all situated on a .23-acre lot. With no HOA and endless possibilities, this property is ideal for buyers looking to create a personalized residence, multi-purpose living space, or investment opportunity. Cash or Renovation Loan financing makes this a fantastic option for those seeking value, space, and the chance to make a property their own while enjoying everything Winter Haven's Chain of Lakes lifestyle has to offer.

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Kimberly Davis (850-625-8855)

Remarks: Need space? This private gated 2.38-acre Winter Haven property with NO HOA offers room to live, play, and grow—bring your RV, boat, ATV, and all your toys. Set well back from the road behind a remote-operated gated entry, this property delivers the privacy and convenience buyers are actively searching for in Winter Haven and throughout Polk County. The fully fenced acreage gives you the freedom to create the lifestyle you want—whether it’s kids playing football or volleyball, evenings around a fire-pit, playground, space for a future pool, or planting your own fruit trees and garden. Inside, the home features an open floor plan with a desirable split-bedroom layout, offering both functionality and comfort. Enjoy formal living and dining spaces for hosting, plus a spacious family room that flows into the kitchen—perfect for everyday living and gatherings. The kitchen is equipped with abundant cabinetry, hardwood flooring, a breakfast bar overlooking your private backyard. The owner’s suite is a peaceful retreat, featuring French doors leading to the screened back porch, a large walk-in closet, and a spa-style bathroom with soaking tub and separate shower. A flexible fourth bedroom near the primary suite provides the ideal space for a home office, nursery, or hobby room. Step outside and experience true Florida living from your 42’ covered front porch or 34’ screened back porch, surrounded by mature trees and open space. This property offers the perfect balance of cleared land for activities and wooded areas for added privacy. Additional features include: * Remote-operated gate for easy access and security * New roof in 2023 * Side-entry 2-car garage + metal carport * Inside laundry room * Well for irrigation & water softener * High and dry acreage *New AC, Well Pump & Water Heater in 2018 *Septic Pumped 2026 Located just minutes from the Polk Parkway, with convenient access to Lakeland, Tampa, and Orlando, this home combines privacy, land, and accessibility—a rare opportunity in today’s market. If you’ve been searching for a gated acreage property in Winter Haven with no HOA and true outdoor living potential, this one checks all the boxes.

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Kimberly Davis (850-625-8855)

Remarks: Welcome to this FULLY renovated, beautiful and large 3Bed 2bath home in Winter Haven!! Property has been fully renovated to 2026 standards in and out. Fresh pain in and out. Brand new 6" baseboards throughout the home. Crown molding throughout the main living space. Brand new water resistant LVP tile. Pool has been repainted. Walls have been refreshed and smoothened out. Popcorn ceiling through the main home has been sanded down and smoothened. Garage has been given a fresh coating of pain and the floors smoothened. Both Florida rooms have been renovated as well. Roof (2020) A/C (2020) New Water-heater installed (2026) Stainless Steel Samsung Dishwasher (2026) Stainless Steel Samsung Fridge (2026) Stainless Steel Whirlpool Electric Range (2026) Stainless Steel Broan-NuTone Range Hood (2026). Solar Panels are fully owned. Full 3D property walk-through video available upon request. PLEASE NOTE - I AM NOT AVAILABLE ON THE SABBATH/SATURDAYS

Listing is courtesy of: CARDINAL REALTY GROUP, LLC. (305-910-2902)

Listing Agent: Meir Tenenbaum (305-721-7408)

Remarks: Under Construction. This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. 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.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Winter Haven home near Chain of Lakes featuring 5 bedrooms, 3 bathrooms, and 2 flexible bonus rooms offering exceptional convenience and a lifestyle close to everything Central Florida buyers love. This move in ready property provides effortless access to major commuter routes, grocery stores, shopping, dining, scenic walking trails, LEGOLAND Florida Resort, and Florida’s beautiful beaches just about 90 minutes away. Step into your own private outdoor sanctuary designed for both relaxation and entertainment. The caged saltwater pool includes a 6×10 sun shelf perfect for in water lounging along with a 3 to 6 foot depth range ideal for both play and leisurely floating. Enjoy the luxury of a heated spa with priority Jacuzzi jet action creating the perfect setting for evening unwinding, stress relief, muscle relaxation, or hosting friends for cozy nights under the stars. The spacious gazebo offers a shaded retreat for outdoor dining, socializing, or simply enjoying the Florida breeze. Practical upgrades elevate this property as it is equipped to support a home generator, has a warrantied water softener for supreme taste, two 5-ft gates that create a wide 10-ft entry to the backyard and a on-site shed adding valuable extra storage keeping everything tidy and easy to access. Inside, the home feels bright, modern, and truly move in ready. The open concept layout creates an inviting flow throughout, and the generous kitchen is perfectly suited for gatherings, meal prep, and everyday connection. With its flexible floor plan, this home easily accommodates large families, multi generational living, or hosting guests with comfort and privacy. A standout property offering both lifestyle and practicality. This home is a must see!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Andrea Friedmann (863-661-6535)

Remarks: Under Construction. Brand new, energy-efficient home available by May 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home providing plenty of privacy and features a spacious walk-in closet and shower. 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.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: Welcome to your perfect slice of Florida living! This solid concrete block home combines durability, comfort, and modern updates - making it an exceptional opportunity whether you're searching for your next residence or an investment property. Step inside to discover brand-new vinyl plank flooring that flows beautifully throughout, complemented by newer stainless steel appliances that bring a fresh, modern feel to the home. Major systems have already been taken care of for you, including a 2022 HVAC system and 2022 water heater, plus a metal roof installed in 2012 for long-term peace of mind. Outside, enjoy a fully fenced yard - perfect for pets, entertaining, or simply relaxing under the canopy of mature shade trees. The carport and additional parking pad provide plenty of space for vehicles, guests, or even a boat. Nestled in an established neighborhood, this home offers the rare advantage of NO HOA or CDD fees, giving you both freedom and affordability. You'll love the convenient location - just minutes from lakes, parks, shopping, and vibrant downtown Winter Haven. Whether you're looking to settle in or invest, this property checks all the boxes. Don't miss your chance to own this move-in-ready gem - schedule your private showing today before it's gone!

Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)

Listing Agent: John Evans (813-992-3483)

Remarks: Under contract-accepting backup offers. Short Sale. Lender has provided preliminary net guidance based on a recent appraisal. Offers will be reviewed in accordance with lender and VA guidelines. Buyer is encouraged to submit highest and best offer. Final approval subject to lender review.This is the kind of home that just feels right the moment you pull in. Set on an oversized .29-acre lot with no rear neighbors and peaceful conservation views behind you, this spacious 4-bedroom, 2-bath home offers room to breathe, grow, and truly settle in. Inside, you’ll find more than 2,200 square feet of comfortable living space—plus a converted garage that gives you even more flexibility. Need a fifth bedroom? A home office? A workout room or game space? This home easily adapts to whatever stage of life you’re in. The heart of the home is the open kitchen, breakfast nook, and family room, designed for everyday living and easy entertaining. Large windows over the kitchen sink flood the space with natural light, while ample cabinetry and a charming barn-door pantry add both function and personality. The living room’s feature wall gives the space character, and luxury vinyl flooring throughout keeps things both stylish and practical. Every bedroom has ceiling fans, making the home comfortable year-round. One of the hidden gems here is the oversized laundry room—complete with built-in cabinets and direct access to the backyard—perfect for storage, projects, or keeping life organized. Major updates mean peace of mind: newer windows and sliding glass doors installed in 2023, updated insulation, a replaced sewer line, newer appliances, a 2021 roof, and solar panels installed in 2022. Even better? The solar panels often result in credits from the power company, helping keep monthly utility costs surprisingly low. Step outside and you’ll see where this home really shines. The backyard feels private and inviting, with a large screened porch, fire pit for cozy evenings, and two storage sheds for all your tools and toys. Whether you’re hosting friends, enjoying a quiet morning coffee, or winding down after a long day, there’s space here to enjoy Florida living your way. The wide driveway easily fits four or more vehicles, making gatherings easy. Located in a quiet non-HOA neighborhood, you’ll enjoy the freedom to live how you want—no HOA or CDD fees—while still being close to shopping, dining, schools, and local attractions. And if you love boating or an active outdoor lifestyle, you’ll appreciate the flexibility this neighborhood offers. This home isn’t just about square footage or upgrades—it’s about comfort, flexibility, and the feeling of finally finding the one. Come see it in person and imagine the life you could build here. Some photos have been virtually staged/enhanced using AI to help buyers visualize the home’s potential with minimal updates or decorating.

Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)

Listing Agent: Katie Sweet (863-990-5141)

Remarks: Welcome to a home that makes everyday living simple and enjoyable. Located in the established Country Club community, this property offers a practical layout, comfortable spaces, and a setting that supports an easy Florida lifestyle. Inside, you’ll find well-proportioned living areas with plenty of natural light, creating an open and functional feel. The kitchen connects seamlessly to the main living space, ideal for daily routines and casual gatherings. Bedrooms are arranged for privacy, with a primary suite that provides a comfortable place to recharge. The interior bedrooms also feature new carpets and a double primary bedroom closet space for his and hers. Outdoors, enjoy an above-ground pool with a screened enclosure—perfect for Florida afternoons, weekend gatherings, or low-maintenance relaxation year-round. The yard still offers space for outdoor seating, play, or gardening without excessive upkeep. Conveniently located near shopping, dining, medical facilities, and major roadways, this home offers easy access to everything Winter Haven has to offer, including local lakes and recreation. A solid choice for buyers seeking comfort, convenience, and value in a well-located neighborhood.

Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)

Listing Agent: Jeremy Ortiz (863-944-5754)

Remarks: **PRICE IMPROVEMENT** Welcome to the community of Eagle Landing in beautiful SE Winter Haven, Florida. This newer home features 4 Bedrooms/2.5 Bathrooms with a spacious two-story layout that maximizes space and natural light perfect for any lifestyle with Low HOA and NO CDD. The modern kitchen design with Island and Breakfast Bar complete with Granite countertops. The primary bedroom with en-suite bathroom with dual sinks, walk in shower and walk-in closet and 3 additional bedrooms offers plenty of space for a growing family or multi-general family. Needs a little TLC on the inside. The solar panels feature a great savings to help keep your energy cost down. Conveniently located in a quiet neighborhood, this property is ideally situated close to Publix, Legoland, schools and the Winter Haven Chain of Lakes. If you're looking for a modern, quiet neighborhood, this is your chance. Schedule your showing today before it's gone!

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Cheryl Brewer (863-224-0045)

Remarks: BACK ON MARKET!! Welcome to the lakefront community of Edgewater Manor! Come see this awesome custom built 2017 4 bed 3 bath corner lot (1/3 ac.) home with fenced backyard! Located just off Cypress Gardens Blvd., this bright, open floorplan includes combo living and dining area, an office, and a spacious kitchen with white wood cabinets and grey granite counter tops, stainless steel appliances, gas stove, and eat-in area. There is a large family room off the kitchen, crown molding throughout the home, vinyl fencing, and much more, including: gas tankless WH, vinyl planking floor everywhere but bedrooms, plantation shutters, double pane low E windows, a screened lanai. There is even a plug for an electric car built into garage wall, and a shallow well for lawn irrigation. Plus, close to Legoland, restaurants, shopping, and the chain of lakes. A great find!

Listing is courtesy of: STORMS REALTY (813-293-4652)

Listing Agent: Steve Storms (813-293-4652)

Remarks: Under Construction. New construction home with 2819 square feet two-story including 5 bedrooms, 3.5 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, and a tiled shower. Bedrooms 3 and 4 share a jack-and-Jill bathroom. Plus, enjoy a 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. “Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey."

Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)

Listing Agent: George Lindsey, Iii (863-797-4999)

Remarks: Nestled on a beautifully landscaped and tree shaded lot this well maintained 3 bedroom 2 bathroom home features split bedrooms with ample closets, formal living and dining areas, an expansive family room, breakfast bar in the kitchen and an attached 2 car garage. Additional amenities include an oversized rear screened lanai overlooking a serene kidney-shaped screen-enclosed pool with southerly exposure. Cypresswood Golf & Country Club offers a variety of amenities, including an 18-hole golf course, clubhouse with pro shop and lounge, Jr Olympic swimming pool and a soon-to-be-completed tennis, pickleball and recreation area. Located in close proximity to HWY 27 affords easy access to I-4 and within 1.5 hours of either coast. This ideal location is just a mile down the road from a brand new Publix as well as being conveniently close to shopping, restaurants, and Legoland.

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Steven Smith, Pa (863-224-2297)