Winter Haven Single Family Homes For Sale - 795 homes

Remarks: Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Country Club community of Winter Haven. Thoughtfully designed with a desirable split-bedroom floorplan, this residence offers both privacy and functionality for everyday living and entertaining. Plus, seller is currently in the process of installing a NEW ROOF! Step inside to find beautiful hardwood and tile flooring throughout, creating a warm yet low-maintenance living environment. The spacious primary suite serves as a private retreat, complete with direct access to the screen-enclosed pool deck — perfect for enjoying your morning coffee or an evening swim under the stars. The heart of the home flows seamlessly into a dedicated dining area, with an exciting bonus room just beyond featuring a fun wet bar — ideal for hosting gatherings, game nights, or creating your own lounge space. Two additional bedrooms are situated on the opposite side of the home, providing comfort and privacy for family or guests. Outdoors, the screened pool deck offers the perfect space for relaxing or entertaining year-round. The garage includes a dedicated workshop area, making it ideal for hobbyists, DIY enthusiasts, or extra storage needs. Beyond the home itself, residents enjoy an exceptional lifestyle within this premier community, featuring a championship 18-hole golf course, community pool, fitness center, clubhouse, on-site restaurant, and pro shop. Exciting new amenities are on the way, including lighted tennis courts, pickleball, and basketball courts — offering something for everyone. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando and Tampa International Airports, and the gulf-side beaches of Tampa/St. Pete! This is more than just a home — it’s a lifestyle. Schedule your private showing today!

Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)

Listing Agent: Kayly Malinas, Pa (863-258-1426)

Remarks: Short Sale. Welcome to this beautiful Winter Haven home! Villamar This property offers a spacious layout, abundant natural light, and comfortable living areas ideal for everyday living and entertaining. The backyard provides great outdoor potential. Conveniently located near shopping, dining, schools, and major highways. Short Sale opportunity — perfect for buyers looking for value and investment potential.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Yoja Mirabal (407-543-7789)

Remarks: Under Construction. New construction home with 2227 square feet on two-story including 4 bedrooms with loft, 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 2 and 3 share a jack-and-Jill bathroom. Plus, enjoy a covered lanai, 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 decor do not convey."

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

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

Remarks: *PRICE IMPROVEMENT*~2/2 Winter Haven residence Offered for Sale~ Great opportunity for a first-time home buyer or an investor! This adorable 2/2 property features 1396 square feet of living area, a split plan, two bonus rooms which could be used as bedrooms, vaulted ceilings, primary bedroom with walk-in closet and en-suite bath, wood burning fireplace, large, screened patio and a one car garage. Roof and A/C are less than 5 years old and water heater is newer. Convenient to fishing, dining, shopping, and medical/educational facilities. Monthly HOA fee covers grounds maintenance, streetlights and community pool care.

Listing is courtesy of: HOUSE OF GLASS REAL ESTATE PM (863-940-3756)

Listing Agent: Andrea Muzzy (863-430-1733)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this beautifully updated three-bedroom, two-bathroom home with a two-car garage, offering 1,866 square feet under roof in the desirable community of Winter Haven. From the moment you arrive, you’ll appreciate the freshly painted exterior and updated landscaping that create strong curb appeal, setting the tone for what awaits inside. Step through the front door into a bright and refreshed interior featuring newly painted walls, updated doors, and modern light fixtures. The great room is highlighted by new luxury vinyl plank flooring that continues into all bedrooms, offering both durability and a clean, contemporary feel. The kitchen is designed for both functionality and style, featuring brand-new stainless-steel appliances and a seamless flow into the main living space—perfect for everyday living and entertaining. The split-bedroom layout provides privacy, with a spacious primary suite that includes updated mirrors and finishes in the en suite bathroom. Two additional bedrooms and a second full bath offer flexibility for family, guests, or a home office. Throughout the home, you’ll find new ceiling fans, updated blinds for window treatments, and thoughtful upgrades that make this home truly move-in ready. Additional improvements include a Brand-new roof, new hot water heater, and a freshly painted garage floor, adding both value and peace of mind. Located in a sought-after area of Winter Haven, this home offers convenient access to shopping, dining, and local attractions, while still being tucked into a welcoming community known for its charm and proximity to the area’s beautiful lakes. This is a fantastic opportunity to own a fully updated home in one of Central Florida’s most desirable and growing locations.

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Jason Stone (863-838-8972)

Remarks: Experience refined lakefront living on the iconic Winter Haven Chain of Lakes, perfectly situated on the coveted shores of Lake Mirror—one of the most picturesque and desirable lakes in the chain. Known for its tranquility, stunning estate homes, and seamless access to the full chain, Lake Mirror offers a rare combination of privacy, beauty, and true waterfront lifestyle. This impeccably maintained 4-bedroom, 3.5-bath residence is a showcase of timeless architecture and elevated design, where every space has been thoughtfully curated to maximize comfort, light, and connection to the outdoors. From the moment you enter, you’re met with expansive living areas, soaring ceilings, and walls of French doors that line the back of the home, flooding the interior with natural light and creating a seamless transition to the outdoor living spaces. These multiple sets of French doors not only enhance the home’s elegance, but also provide direct access from several rooms to the patio, pool, and lakefront setting, blurring the line between indoor and outdoor living in the most effortless way. The outdoor experience is nothing short of exceptional. A resort-style screened pool and spa overlook the water, framed by peaceful lake views and designed for both quiet relaxation and unforgettable entertaining. Whether hosting guests, enjoying a sunset swim, or simply unwinding after a long day, this space delivers a level of serenity that is hard to replicate. Step beyond to your private dock and embrace everything the Chain of Lakes lifestyle has—boating to dinner, skiing across open water, fishing at sunrise, and cruising through one of Central Florida’s most connected and sought-after lake systems. Additional highlights include a brand-new seamless metal roof in 2025, an expansive 3-car garage, and meticulous pride of ownership throughout, ensuring both beauty and peace of mind. This is a rare opportunity to own a home where luxury, lifestyle, and location come together effortlessly—a true lakefront retreat in the heart of Winter Haven.

Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)

Listing Agent: Brock Jennings (863-990-5846)

Remarks: Welcome to this beautifully updated 4-bedroom, 2-bathroom pool home in desirable Southeast Winter Haven. This move-in ready residence sits on a spacious lot with fantastic curb appeal and an incredible backyard oasis. Extensively updated in 2019 and meticulously maintained, the home features an open, light-filled layout with fresh white walls, stylish luxury vinyl flooring, and a cozy brick fireplace. The kitchen offers white cabinetry, stainless steel appliances, quartz countertops, and a dining area perfect for entertaining. The property includes four generous bedrooms—including a primary suite with a walk-in closet—versatile spaces for work or play, and a charming entry gallery. Additionally, a new roof was installed in January 2021. The backyard was further enhanced in 2025 with a complete pool renovation, a new paver deck, and a screened patio. This large covered area with ceiling fans overlooks the refinished pool, while the fully privacy-fenced yard provides ample room for recreation. Conveniently located near local amenities, schools, LEGOLAND, and the Chain of Lakes, this home perfectly combines comfortable living with the Florida lifestyle. Call today to schedule your private tour, this is a gem you won't want to miss!

Listing is courtesy of: 1513 REALTY LLC (863-431-2000)

Listing Agent: David Craig (863-605-3437)

Remarks: Come and make this move-in ready three-bedroom, two-bathroom home your own in Central Pointe! The interior features two spacious living areas with vaulted ceilings and plenty of natural light, creating an airy atmosphere. The main living areas flow seamlessly with the kitchen and dining area, perfect for everyday living and entertaining. The primary bedroom offers ample storage space with a large walk-in closet and beautifully updated ensuite with large soaking tub and walk-in shower. Step outside to enjoy the privacy of a fully fenced-in backyard that overlooks serene waterfront views. Conveniently located near shopping, restaurants, schools, and medical facilities, this home also provides quick access to major highways for an easy commute to Tampa or Orlando. Schedule your private showing today!

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: Discover a truly unique architectural gem in the heart of Winter Haven. Inspired by the timeless design style of Frank Lloyd Wright, this beautifully maintained home offers character, warmth, and distinctive architectural details rarely found in today’s market. From the moment you arrive, you’ll appreciate the clean lines, natural light, and thoughtful design elements that create a seamless connection between indoor and outdoor living. The home has been exceptionally cared for and is in very good condition, offering both charm and peace of mind. Spacious living areas, inviting atmosphere, and a layout full of personality make this property stand out from the ordinary. Whether you are looking for a primary residence, a second home, or an investment opportunity, this home delivers style and timeless appeal. Roof replaced in 2004. Conveniently located near downtown Winter Haven, shopping, dining, parks, and the Chain of Lakes. Schedule your private showing today and experience the character and beauty of this one-of-a-kind property.

Listing is courtesy of: MBA REALTY GROUP, INC (407-291-4665)

Listing Agent: Paola Arias (407-969-9211)

Remarks: Located just minutes from the beautiful Chain of Lakes, public lake access, parks, restaurants, and the vibrant recreational areas of Winter Haven, this property offers both convenience and lifestyle. This 3-bedroom, 2-bath home features a very spacious kitchen with eat-in area, inside laundry, and an oversized family room that offers excellent flexibility and can easily be used as a guest space, office, or potential extra bedroom. Major updates include a metal roof, HVAC replaced in 2023/2024, and water heater from 2015. Currently tenant-occupied, this property also presents an immediate income-producing opportunity for investors or buyers looking for cash flow from day one.

Listing is courtesy of: MBA REALTY GROUP, INC (407-291-4665)

Listing Agent: Paola Arias (407-969-9211)

Remarks: PRICE ADJUSTMENT***Don't Miss This Opportunity! This home offers amazing potential and features 4 bedrooms and 1 full bath, making it ideal for homeowners or investors. The kitchen is just off from the spacious dining area, great for family gatherings, while the spacious living room and family room provides extra space to relax. The primary bedroom as well as the other rooms are generously sized, offering a built-in closets. This home is a great candidate to be transformed into your ideal living space or added to your rental portfolio. Property is being sold As-Is. All buyers MUST view the home in person before submitting an offer. Opportunities like this don't last long, schedule your showing today before it's gone! ** FURNISHINGS, WASHER, DRYER, OR REFRIGERATOR DOES NOT CONVEY WITH THE SALE OF HOME.

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

Listing Agent: Twanna Dewdney (863-207-1634)

Remarks: Welcome to this well-located single-family home situated in Winter Haven, offering a comfortable layout and enjoyable outdoor space. This home features 4 bedrooms and 2 bathrooms with a practical floor plan that supports everyday living, along with a 2-car garage and a large driveway. The property also includes a newer shingle roof (2023) and newer LVP flooring. Inside, the living area offers two living room areas, one at the entrance and another one by the kitchen, creating a welcoming space that makes it easy to stay connected whether you’re relaxing at home or entertaining guests. The bedrooms are nicely sized, and the primary suite provides added comfort with a walk-in closet and a private bathroom that features both a bathtub and a separate shower. The second full bathroom add convenience and functionality for the household. Whether you’re searching for a place to make your own or an investment opportunity, this home is worth a look. Schedule your showing today.

Listing is courtesy of: FLORIDA SPIRIT HOMES (407-396-4441)

Listing Agent: Gabriel Silva Andrada (321-666-0301)

Remarks: ALMOST PARADISE! Enjoy the peaceful surroundings and relaxing environment from this 2142 SF executive style home located in The Gates of Lake Region, a well maintained and GATED community close to the Winter Haven Country Club! NEED SPACE? This customized 4BR/2BA home was designed with an open floor plan with split bedrooms, formal dining room and living room ( which could be easily used as a study, library and/or den), family room and interior laundry room. Note the Curb Appeal of the landscaping, TILE ROOF and BRICK paver driveway and walkway! The inviting and covered front porch provides respite from inclement weather. As you enter the entry foyer, the living room will be to the immediate left and the dining room to the right. Straight ahead is the family room with a set of sliding glass doors that opens onto the screened in lanai. Settle back, listen to the birds singing and observe the cows on the adjacent ranch property! To the left of the family room are bedrooms #2 and #3 and to the right is the kitchen, dining nook, primary bedroom suite, bedroom #4 and the laundry room! The well planned kitchen has a breakfast bar, white cabinetry with neutral colored solid countertop and stainless steel appliances. The kitchen appliances have been updated from 2018-2025. The spacious primary suite has sliding glass doors leading to the lanai, two walk-in closets and an ensuite bathroom with dual vanities and sinks, jetted tub, separate shower and a water closet! Bedroom #4 is currently used as a home office. The floor plan allows creativity in use. Most recent updates include: Water Heater replaced Feb. 2026; AC/Heat system April 2025; garbage disposal and microwave 2025; and lanai screen & door 2025. The PERIMETER 90 X 120 lot is a generous in size. There is room to add a pool, outdoor kitchen, play area and/or garden! The HOA fee provides re-use irrigation water and maintenance of the gate and common areas. Perfect for a year round or winter residence, this home is a blank canvas just waiting for YOUR decorating touches! For those who enjoy golf and/or tennis, the Country Club of Winter Haven is just 2 Blocks away! Publix Supermarket is conveniently located within 0.8 mile with additional stores and a bank currently under construction! Easy access to downtown Winter Haven, HWY 27 and I-4. Legoland, Bok Tower, world-famous theme parks of Disney, Universal Orlando, Sea World, water adventure parks, downtown Orlando and various other nature parks are within a 7 to 60 mile drive. Be sure to make your appointment to view this outstanding property! Measurements are approximate. All information is believed to be accurate but not guaranteed.

Listing is courtesy of: JUDY B CLEAVES PROPERTIES INC (863-299-5878)

Listing Agent: Carol Jean Sheil (863-412-3801)

Remarks: The property you are viewing is comprised of four individual parcels all being sold together. Also see MLS B4901531. This property has two parcels with single family homes on it , two vacant parcels, and easement parcel. The two single family homes are both concrete block built, 2 bedrooms and 1 bath room The entire sale parcel is almost 1 acre. These parcels are zoned RL 3 but have the potential to have a future land use zoning change. The corner lot sits across from a commercial store. Located on the corner of Eagle Lake Loop and Rifle Range road this area is rapidly growing with both residential and commercial opportunities. Property location has great opportunities for potential land use change based on surrounding parcels.

Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)

Listing Agent: Craig Burke (863-899-5010)

Remarks: Under contract-accepting backup offers. ***UNDER CONTRACT ACCEPTING BACK UP OFFERS*** Tucked away on a oversized lot on a quiet cul-de-sac in Winter Haven, this BEAUTIFULLY RENOVATED POOL HOME offers the perfect blend of comfort, style, and outdoor living at an incredible value. Featuring 3 spacious bedrooms, 2 bathrooms, and walk-in closets, this home was thoughtfully designed for both everyday living and entertaining. Step inside and fall in love with the STUNNING RENOVATED MODERN KITCHEN and OPEN-CONCEPT FLOORPLAN, creating a bright and inviting atmosphere throughout the main living areas. The seamless flow between the kitchen, dining, and living spaces makes this home ideal for hosting family and friends. Outside, your PRIVATE BACKYARD OASIS awaits with a 16’ x 32’ pool, screened porch, expansive patio, and beautifully designed outdoor entertaining space overlooking a peaceful setting with no rear neighbors. The FULLY FENCED BACKYARD provides added privacy and security, perfect for pets, family gatherings, or simply relaxing in tranquility. Located in a quiet and desirable community, this home is one of the best-priced pool homes in the area. Sellers are offering a credit for pool repair, creating an incredible opportunity for the next owner. Whether you are looking for your first home, a vacation retreat, or the perfect place to entertain, this move-in-ready gem checks all the boxes and comes with a LOW ANNUAL HOA. Schedule your private showing today!

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

Listing Agent: Caroline Vansevenant (407-946-5675)

Remarks: Under contract-accepting backup offers. Welcome to true lakefront living on the renowned Chain of Lakes in Winter Haven, perfectly positioned on Lake Shipp with approximately 500 feet of waterfrontage, an extremely rare offering that creates the feel of your own private park right in your backyard. Built in 2021 with block-on-slab construction and a durable metal roof, this 3-bedroom, 3-bathroom home was designed to maximize water views and effortless indoor-outdoor living. Inside, you’ll find soaring ceilings and an open layout that flows seamlessly into the kitchen, featuring 42-inch cabinetry, quartz countertops, a large island, pantry, and a dine-in area—ideal for entertaining or everyday living. Large 8-foot sliding glass doors open out to a fully screened lanai that spans the entire width of the living area, creating a true extension of the home and the perfect place to relax while overlooking the water. The split floor plan offers privacy, with a spacious primary suite positioned to capture lake views, complete with a large walk-in closet and a spa-style en-suite bathroom featuring double vanities and a walk-in shower. One of the additional bedrooms also features its own en-suite bathroom, creating a secondary primary suite—ideal for guests or multi-generational living. The remaining bedroom is well-sized and positioned for convenience. Step outside and embrace the lifestyle this property was built for. With your own private dock, you can moor your boat and enjoy direct access to the Chain of Lakes. Cruise across to local favorites like Harborside Restaurant and take in some of the best sunsets Central Florida has to offer. Additional features include plantation shutters on the front of the home, a spacious indoor laundry room, a detached storage shed, and a rare drive-through 3-car garage with access from the front all the way to the backyard—perfect for boats, trailers, or additional vehicles. With no HOA and close proximity to downtown Winter Haven, this property delivers a unique combination of space, convenience, and true waterfront living. This is more than just a home—it’s a rare opportunity to own a standout piece of lakefront property on the Chain.

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

Listing Agent: David Small (407-601-8351)

Remarks: Under contract-accepting backup offers. Now is your chance! Come and be a part of this active, Golf Course community and live in this beautifully maintained, updated home. Enjoy the peaceful screened courtyard with your cup of coffee, or watch the gorgeous Florida sunsets. The inside of the home has been lovingly kept up and updated. You won't want for space in this well thought out layout. Plenty of room for entertaining, or a quiet read alone. The garage has been set up for your perfect workspace or storage, whatever suits your needs. You have unlimited options with the screen garage door and a mini split that keeps everything cool when you need it! This golf course community is gated with a guard 24/7. Even if you don't golf, there will be something for you to do. Jr Olympic size pool, tennis courts, soon to be pickleball courts and a full service clubhouse with live music every weekend. Enjoy peace of mind knowing that the AC is less than a year old and the roof was replaced in 2022! Schedule your viewing today and welcome home!

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Stacy Tuttle (863-602-9554)

Remarks: Auction Property. Ranch-style home offering 2 bedrooms and 1.5 bathrooms with a spacious living room and a good-sized yard. Features include a durable metal roof, RV electrical hookups, and a chicken coop. Some updates in the kitchen. Short Sale subject to lender approval.

Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)

Listing Agent: David Hartigan (407-955-1156)

Remarks: Welcome home to this beautifully updated 3-bedroom, 2-bath residence ideally situated in the heart of Winter Haven, just minutes from downtown and surrounded by the area’s picturesque lakes. This move-in ready home has been thoughtfully upgraded throughout, offering stylish vinyl flooring, refreshed bathrooms, modern light fixtures, and a beautifully renovated kitchen featuring granite countertops, updated cabinetry, a trendy backsplash, and stainless steel appliances. The inviting living room is anchored by a cozy fireplace, creating the perfect space to relax or entertain. Step outside to your private, fully fenced backyard complete with a fire pit—ideal for enjoying Florida evenings with family and friends. Additional highlights include a spacious two-car garage with laundry area, a convenient enclosed storage space, and a newer roof (2022) for added peace of mind. With no HOA and a prime location close to shopping, dining, and everything downtown Winter Haven has to offer, this home truly combines comfort, style, and convenience. Don’t miss your chance to make it yours!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Robert Johnson (813-364-2250)

Remarks: Under Construction. New construction home with 2227 square feet on 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 2 and 3 share a jack-and-Jill bathroom. Plus, enjoy a covered lanai, 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 decor do not convey."

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

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