Winter Haven Homes For Sale & Real Estate - 917 homes

Remarks: 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: Under contract-accepting backup offers. Charming 3-bedroom, 2-bath home located in a desirable HOA community in Winter Haven! This well-maintained residence offers 1,148 square feet of comfortable living space with a functional layout designed for everyday living. Enjoy the convenience of an interior laundry area and a spacious living room that flows into the dining and kitchen areas. The primary suite features a private bathroom, while two additional bedrooms provide flexibility for family, guests, or a home office. Step outside and take advantage of the community amenities, including a refreshing community pool perfect for relaxing and enjoying Florida living year-round. Conveniently located near shopping, dining, schools, and major roadways. Great opportunity for homeowners or investors alike!

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

Listing Agent: Marisela Quintero (863-605-1566)

Remarks: One or more photo(s) has been virtually staged. Short Sale. Back on the market with renewed opportunity! Enjoy peaceful lakefront living in this beautiful updated 2 bedroom, 2 bath condo located in the gated Winterset community. Featuring an open floor plan granite countertops, stainless steel appliances, upgraded cabinetry, and a cozy breakfast nook, this home offers both comfort and style. The enclosed balcony showcases stunning views of Garden Lake, perfect for quiet mornings or relaxing evenings. Recent updates include plumbing, electrical, lighting, bathroom vanities, and updated flooring throughout, making this home truly move-in ready. Winterset offers resort - style amenities including pool, spa, clubhouse, tennis and pickleball courts, and a private lakefront pier. Conveniently located just minutes from LEGOLAND and under an hour to Orlando attractions. Short sale- priced in alignment with lender expectations. A great opportunity for buyers looking for value, a primary residence, or an investment property.

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

Listing Agent: Valerie Howze (863-604-9080)

Remarks: This is a very well maintained home which is priced to sell! The property has many upgrades; a new roof in 21, new AC coil in 25, and newer countertops. It is also located close to the side entrance gate for easy access. No rear neighbors provides for a more serene atmosphere and the north facing rear screened porch is pleasantly shady and backyard has room to be expanded. This is truly Central Florida's retirement living at its best. Located in a master planned community with most exterior maintenance included for easy living and full resort-like amenities. The beautifully maintained on-site managed lakefront community clubhouse offers many opportunities for an active lifestyle. This home is move-in ready.

Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)

Listing Agent: Scott Kline (863-287-0204)

Remarks: Conveniently located in the heart of Winter Haven, this 5 Bedroom 3 Bathroom home with two Flex Rooms is move in ready and close to everything loved, including: Easy commuting, Grocery Stores, Shopping, Dining, Chain of Lakes, Boat Ramps, Scenic Walking Trails, Legoland Florida Resort, and Beaches just an hour and a half away! Step outside to your private oasis featuring a Caged Saltwater Pool with a Safety Alarm System, perfect for peace of mind. The spacious Gazebo adds a relaxing shaded retreat for outdoor dining, lounging, or entertaining. Unique Bonus Room with a Sound Proofing wall, ideal for Recording Studios, Podcasters, Musicians, Content Creators or any Work from home professionals needing their quiet space. This home shows like new with Fresh interior paint, New Luxury Laminate flooring, Carrara porcelain tile for a sleek modern finish, Bright open concept living spaces and a Spacious Kitchen perfect for gatherings. With this home offering flexibility for Large Families, Multi Generational living or hosting guests comfortably, it is a must see! Schedule your showing soon!

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

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

Remarks: Under contract-accepting backup offers. Central Florida Lakefront home for sale now with a HUGE PRICE IMPROVEMENT! Move in ready 4BR/2BA with Office on Private-Access Lake Bess complete with a Slalom Ski Course! Enjoy direct connection to Lake Ruby! You access to TWO beautiful lakes featuring white sandy bottoms, tranquil waters. These lakes are ideal for water sports (private access) and serene lakeside living. The open layout and large glass sliding doors create a seamless connection between Indoor Elegance and Outdoor Beauty, making every arrival feel like a moment of escape! Enjoy Updated Features including ROOF 2019, NEW EPOXY GARAGE FLOORING, Stunning Views, Resurfaced Pool, Covered Lanai for Outdoor Living, NEWLY PAINTED Dock with Boat Lift, Large Windows for Natural Light, Formal Dining Room, Lake View Breakfast Nook and Inside Laundry Room with Utility Sink and Cabinets. The Kitchen offers Lake Views, Granite and a Full Appliance Package, while the Spacious Primary Suite includes a Walk-In Closet and a Luxurious En-Suite Bathroom. This lakefront Split Floor Design not only enhances privacy for you and guests but also creates a more spacious, balanced flow throughout the home, ideal for both everyday living and entertaining. Enjoy lush landscaping with an eco-friendly irrigation system that draws from the lake. Come see why Ruby Lake with barely over 200 homes is ideal with Manicured landscaping, Underground Utilities and quiet streets for evening or morning strolls. Located less then two miles from a Golf Course, less than five to Legoland, shopping, dining, and medical facilities plus easy access to both Tampa and Orlando. Florida's Beautiful Gulf and Atlantic Beaches less then two hours away in either direction! Cruise enthusiasts, Port Canaveral is only 70 miles away! Whether you're seeking adventure on the water or peaceful evenings by the dock, Ruby Lake offers a lifestyle that’s both vibrant and serene!

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

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

Remarks: Under contract-accepting backup offers. This beautifully updated split floor plan home in the desirable Eloise Woods subdivision offers the perfect blend of comfort, quality upgrades, and incredible outdoor living. Nearly every part of this home has been improved, making it truly move-in ready. Inside, the home features updated flooring throughout, renovated bathrooms, redone ceilings, updated electrical and plumbing, new interior doors and trim, and an updated kitchen with new counters, custom backsplash, stainless appliances, and a large wrap-around bar that makes the kitchen the true heart of the home. The layout flows nicely with a spacious living area and flexible dining space that could also be used as an additional den or sitting room. The primary bedroom includes an en-suite bathroom, walk-in closet, and sliding glass doors that lead directly to the pool area. The secondary bedrooms are generously sized with great closet space, and the guest bathroom offers convenient access to the pool patio—perfect for when family and friends come over to enjoy the backyard. Step outside and you’ll immediately see what makes this home special. The pool area has been extensively upgraded with an extended deck finished with beautiful travertine tile, creating an incredible space for entertaining. Multiple pergolas, a built-in bar area, paver walkways, and private fencing create a backyard that truly feels like your own personal retreat. Additional improvements include updated windows and sliding glass doors with built-in custom blinds, custom closet systems, updated garage with epoxy flooring and storage, new soffit and fascia, gutters with screens, irrigation system, and a new drain field. Major mechanical updates give peace of mind with a full home re-pipe completed in 2014, new A/C and ductwork in 2019, and a brand new roof installed in April 2024. From the interior upgrades to the incredible outdoor entertaining space, this home offers a rare opportunity to own a fully updated property in Eloise Woods where the list of improvements is truly extensive.

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

Listing Agent: Sam Daniels (863-412-8218)

Remarks: Rare opportunity! Exceptional home with 4 bedrooms, 2 baths, and 2-car attached garage. Open-concept living with quarz kitchen, center island, and ceramic tile floors. Primary suite with walk-in closet and en-suite bath. Features include covered screened lanai, fully fenced yard, gutters, irrigation, and inside laundry. Desirable location, this home won’t last!

Listing is courtesy of: MIHOUSE REALTY LLC (407-286-2690)

Listing Agent: Martha Leighton, Pa (407-223-7767)

Remarks: Under contract-accepting backup offers. WELCOME TO THIS AMAZING POOL HOME SITUATED ON AN OVERSIZED (.43) ACRE LOT LOCATED IN HAMILTON POINTE, AN ESTALISHED LAKEFRONT COMMUNITY IN WINTER HAVEN, FL! As you enter, you will immediately notice the NATURAL LIGHT, HIGH CEILINGS, OPEN CONCEPT FLOORPLAN and BEAUTIFUL POOL VIEW. The spacious eat-in kitchen features lots of built-in cabinetry, granite countertops, stone backsplash, double ovens, island with cooktop, large double sink and another great view of the pool area! The primary en-suite has an oversized soaking tub for relaxing, double sinks, large walk-in-shower with built-in-seating, 2 huge walk-in closets with custom shelving, and plantation shutters. The 2 additional bedrooms are very spacious and feature built-in closet shelving. The second full bath has been tastefully updated with granite countertops, canned lighting and large walk-in shower with corner seating. The oversized and fully screened pool and patio area is perfect for all your entertaining! Thanks to the solar/electric heated pool, you will be able to enjoy swimming year-round. The 1/2 bath is conveniently located just in from the screened lanai, making it convenient for guests. Don't forget about the spacious 3 car (25 x 35) garage and circle drive for visitor parking. The inside laundry room has cabinetry for extra storage and also features a utility sink. Save $$ on your water bill with your very own irrigation well. A newer hot water heater installed (2024) will also add to the home's efficiency. Don't miss out on this meticulously maintained property centrally located between Tampa International and Orlando International Airport! The Country Club of Winter Haven, shopping, medical and LEGOLAND, FL are just minutes from this wonderful property that has been lovingly cared for.

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

Listing Agent: Wanda Dicks (863-287-7846)

Remarks: Come enjoy the beautiful Florida sunsets, In this beautiful, furnished home. You can relax in the enclosed Florida room, Carport is long enough to put two cars in. floors have the beautiful laminate wood flooring, all through out the livingroom,and dining areas. All located in a beautiful gated 55 plus park. Two heated pools, two clubhouses, tennis ,fishing pier, minature golf, shuffle board, plus much more. this home want last, act fast.

Listing is courtesy of: SOUTHERN BELLE REALTY (863-299-7800)

Listing Agent: Reta Stead (863-299-7800)

Remarks: CORNER UNIT WITH VAULTED CEILINGS AND PRIVATE BALCONY- Welcome to your new retreat in the highly sought-after chain of lakes community of Park Lake — where comfort, style, and location come together beautifully. Step inside this charming one-bedroom, one-bath home and you’ll immediately notice the open feel created by vaulted ceilings and luxury vinyl flooring throughout the main living areas. The kitchen is a true highlight, featuring quartz countertops, sleek cabinets, stylish backsplash a modern tile floor, and all-new stainless steel appliances — including a five-burner stove, low-profile microwave, and refrigerator with exterior ice-maker. Thoughtful upgrades like new sinks, faucets, a garbage disposal, and modern lighting add both function and sophistication. The bathroom feels spa-like with a sleek tile shower, coordinating tile floor, quartz countertop, new sink, fixtures, and an elegant multi-illuminating with anti fog mirror that provides perfect lighting for any time of day. Two sliding glass doors — one from the living room and another from the bedroom — open to your private screened balcony, filling the home with natural light and offering peaceful outdoor views. The spacious bedroom includes a large closet, providing plenty of storage. This home also features a 2026 hot water heater, 2021 roof, and 2017 AC- offering peace of mind for years to come. Updated blinds, modern ceiling fans, and an inside utility with a washer/dryer combo add even more comfort and convenience. Just five minutes from vibrant downtown Winter Haven and next door to the state-of-the-art Advent Health Field House — complete with basketball courts and an Olympic-size swimming pool — this home’s location can’t be beat. Park Lake sits on the shores of beautiful Lake Lulu, where residents can fish from the pier or enjoy skiing right on the water. Perfectly centered near shopping, dining, and grocery stores, this prime location truly offers it all — comfort, convenience, and the best of the Florida lifestyle. Listing agent is owner. Seller Financing Available.

Listing is courtesy of: LIONHEART BROKERS (321-214-4640)

Listing Agent: Claudia Centesimo (407-383-8882)

Remarks: Welcome to this charming three-bedroom, two-bath home nestled in the desirable Lake Daisy Wood neighborhood. Featuring a practical open concept floor plan with tile throughout, this residence is designed for comfortable living. The inviting living room seamlessly connects to a screened porch lanai through sliding glass doors, providing a perfect view of the spacious, fenced backyard—ideal for gatherings or relaxation. The kitchen boasts a convenient breakfast bar and a separate eating area, while a dedicated laundry room connects the garage to the home for added convenience. The generous primary bedroom offers an en suite bath complete with a tub, separate shower, and a large walk-in closet, with its own sliding glass doors leading to the screened lanai. As an added benefit, with a full-price offer, the seller will pay off the solar system in full. This home combines functionality with a welcoming atmosphere, perfect for everyday living.

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

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

Remarks: PRICE REDUCTION!!! MOTIVATED SELLER!!! Discover this exceptional income-producing property perfectly situated on a spacious 0.48-acre lot in the heart of Winter Haven. This versatile property features two separate living spaces, one currently rented—providing immediate income and excellent long-term investment potential. The main home which is now vacant and ready for it's new owners or tenants offers 3 bedrooms and 2 bathrooms, including a generous master suite with an en-suite bath. The open and functional layout makes it ideal for families or long-term tenants. Attached to the main residence is a 484 sq. ft. in-law suite currently rented, complete with a full kitchen, bedroom, bathroom, and private entrance. This flexible space can serve as an additional rental unit, private guest quarters, or be seamlessly integrated into the main living area for multi-generational living. This home was recently appraised above the asking price, giving buyers instant equity and outstanding value. Whether you’re an investor seeking steady cash flow or a homeowner looking for flexibility, this property is a rare find. Take advantage of strong rental demand, potential appreciation, and the benefits of owning in one of Florida’s fastest-growing counties, consistently rated among the best places to live. Don’t miss your chance to own this unique multi-unit property—schedule your private showing today!

Listing is courtesy of: BRIGHT REALTY (941-552-6036)

Listing Agent: Jen Victor (941-587-2787)

Remarks: Welcome to resort-style living in the highly sought-after gated waterfront community of Winterset, where convenience meets comfort in this charming 2-bedroom, 2-bathroom downstairs condo. Step inside to discover a spacious living and dining room combo that creates an inviting atmosphere for relaxation and entertaining. The well appointed kitchen features stainless steel appliances and a convenient breakfast bar, perfect for causal dining or morning coffee. The master bedroom suite features a generous walk-in closet, providing ample storage space. For your convenience, a stackable washer and dryer are included. This professionally managed community boasts a plethora of amenities, including a clubhouse, fishing pier, heated pool, hot tub, and tennis courts—all overlooking the serene Lake Winterset, part of the renowned "Chain of Lakes." Enjoy peace of mind with state-of-the-art security in this well-maintained environment. You’re just minutes away from Lego Land and conveniently located near Disney and other Florida amusement parks, shopping, dining, and more. Alternatively, relish the numerous community offerings, including a fitness center, shuffleboard, and expansive green spaces perfect for walking your family pet. Additionally, most furniture is negotiable, providing a seamless transition into your new home. Experience the perfect blend of leisure and lifestyle at Winterset!

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

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

Remarks: PRICE ADJUSTMENT....Located within a desirable gated community, this beautifully maintained home at 455 Majestic Gardens Blvd offers both comfort and functionality. Featuring a 1-year-old roof and an open floor plan, the home is designed for effortless everyday living and entertaining. The kitchen is appointed with granite countertops and flows seamlessly into a spacious family room. Tile and laminate flooring run throughout the home, adding durability and style. A bonus room provides flexible space ideal for a home office or additional sitting area. Step outside to your private backyard oasis with a fully fenced yard, inground swimming pool with spa, and a paver deck—perfect for relaxing or hosting gatherings. This home combines modern updates, versatile living spaces, and resort-style outdoor living in a secure, gated setting. This home boasts a 30 panel solar system that generates 16,447 kwz per year. The pool is heated by a separate propane system.

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

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

Remarks: Looking for a peaceful lakefront pool home or well appointed AibBnB property? This beautiful 3-bedroom, 2-bath home sits on Lake Connie in Winter Haven’s northern Chain of Lakes and has been completely renovated to include a brand new roof, 4-ton A/C, luxury vinyl plank flooring, interior / exterior paint, and new water heater all installed in 2025. The interior living area includes new fixtures, new front and rear sliding glass doors. The kitchen features tons of solid wood cabinets, all new stainless steel appliances, and granite countertops. It includes both a breakfast area and a picturesque cutout with a stunning view of the pool area and lakefront! The laundry room is also built into the kitchen area and includes a unique custom built porthole window that provides both natural light and views to the Florida room and beyond. The kitchen flows into a large enclosed porch (Florida room) with tons of potential! It can include a second living room space, dining room, and even space for a game room or office area! The Florida room includes additional cabinets and a bar area with a granite countertop. From the Florida room you can access the screened open porch where you can enjoy views of boats cruising the lake, skiers cutting through the water, and bald eagles, ospreys, and herons scooping up fish! The primary bedroom features an en suite bathroom with jetted tub/shower, new vanity & fixtures, as well as a large closet. The 2nd bedroom also includes new ceiling fan and a large closet. The garage has been converted into the 3rd bedroom which is oversized with a very large closet and shiplap feature wall. Both bathrooms have been fully renovated with gorgeous subway tile in the showers, new ceramic tile floors and vanities with solid surfaces, as well a new toilets, and exhaust fans. Outside the house has been completely repainted including newly painted concrete from the front to the back of the property. The home features new screen in the pool cage, a brand new pool liner, with new multi-color LED pool light, as well as new light and fan fixtures on the back porch. There is a carport and large outdoor storage closet out front, and also a second driveway to park an extra vehicle or boat. The boathouse, which includes a roll-up door has also been newly painted is wired with electricity and could also function as a workshop. It features new lights, a new side door. The boathouse / workshop is approximately 10x20 feet and has tons of room for all your toys! The property includes its own large dock and a concrete slab along the beach area for launching your own boat. Furnishings in listing are available for separate purchase. As a potential AirBnB, the unit currently sleeps 7 including the pull out couch in the living room, but could potentially sleep 10 with the addition of a second bed in the 3rd bedroom and a second pull out couch in the enclosed porch area.

Listing is courtesy of: HOMECOIN.COM (888-400-2513)

Listing Agent: Jonathan Minerick (888-400-2513)

Remarks: Under contract-accepting backup offers. Spacious and well-maintained 4-bedroom, 2-bath home with a private pool, offering 2,160 square feet of living space on an oversized 0.24-acre lot. Inside, vaulted ceilings create an open, airy feel throughout the main living areas, enhancing both natural light and functionality. The home also features a brand new HVAC system for added peace of mind. Step outside to a generous backyard with plenty of space beyond the pool to relax, entertain, or customize to your needs. Located in Winter Haven, this property offers convenient access to major roadways, shopping, dining, and the area’s well-known chain of lakes, making it easy to enjoy both everyday living and weekend recreation.

Listing is courtesy of: SOUTH CEDAR REAL ESTATE, INC (813-374-7907)

Listing Agent: Caylee Decleene Llc (920-639-2241)

Remarks: Seller financing available on this Income-producing 5-unit property located just minutes from downtown Winter Haven in a high-demand rental corridor. This asset is positioned for strong cash flow, operational upside, and long-term appreciation in one of Central Florida’s most active growth markets. The property offers a diversified unit mix with clear value-add potential through rent optimization and continued area development. Ideal for investors seeking to scale a performing portfolio with stable income and future equity growth. Proximity to a planned townhome development introduces an additional demand catalyst, reinforcing long-term rental stability. Convenient access to retail, dining, major thoroughfares, and ongoing redevelopment enhances tenant appeal and occupancy consistency. Units 3 and 4 feature a shared second-floor balcony overlooking the rear grounds, adding a desirable lifestyle element for residents. Located in a high-growth submarket of Winter Haven experiencing sustained residential expansion and increasing rental demand, this is a strategic acquisition opportunity with measurable upside. Contact for full financials, rent roll, and investment details.

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

Listing Agent: Michael Hochadel (863-604-0018)

Remarks: Turnkey quadplex investment opportunity in Winter Haven with seller financing available, creating flexible acquisition options for investors seeking leverage and immediate entry into a performing asset. This income-producing multifamily property features 4 of 5 units currently leased, delivering strong in-place cash flow with additional upside from one vacant unit. Recent capital improvements include a new metal roof, updated HVAC system, and multiple interior and exterior upgrades completed within the past year, reducing near-term maintenance exposure and supporting long-term returns. The property offers practical unit layouts, established tenancy, and is positioned in a high-demand rental corridor near retail, dining, schools, and major transportation routes. Continued growth and redevelopment throughout Winter Haven reinforce rental demand and long-term appreciation potential. An efficient addition to any rental portfolio, suited for investors pursuing passive income, portfolio expansion, or a structured value-add play. Seller financing terms enhance flexibility and can improve overall income depending on structure. Contact for financials, rent roll, and seller financing details.

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

Listing Agent: Michael Hochadel (863-604-0018)

Remarks: Welcome to 4717 Magnolia Preserve Ave, a beautifully upgraded home nestled in the desirable Magnolia Preserve community of Winter Haven. Built in 2016, this thoughtfully designed home features 3 bedrooms, 2 bathrooms, and a versatile formal dining room that can easily serve as a home office or potential 4th bedroom. Inside, you’ll find an open and inviting floor plan with high ceilings and an extended living area, creating a bright and spacious feel throughout. The kitchen is a standout, showcasing granite countertops, 44-inch cabinetry, stainless steel appliances, and a charming bay window that fills the space with natural light. A breakfast bar seamlessly connects the kitchen to the living area—perfect for entertaining or everyday living. The primary suite offers a true retreat with elegant tray ceilings, dual closets, and a well-appointed en suite bathroom featuring dual vanities and a relaxing garden tub. Step outside through the French doors to your covered patio and enjoy one of this home’s most sought-after features—a fully fenced backyard overlooking a peaceful, picturesque pond. Whether you're hosting gatherings or enjoying a quiet evening, this outdoor space delivers both privacy and a beautiful view. Perfectly positioned in Central Florida, this location offers the best of both worlds—convenient access to world-famous theme parks and an easy drive to Florida’s stunning Gulf and Atlantic beaches. With its ideal layout, scenic backyard, and convenient location, this home offers the perfect blend of comfort and Florida lifestyle living. Come see it for yourself—you won’t want to leave!

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

Listing Agent: Stephen Novak (863-409-3635)