Winter Haven Homes For Sale & Real Estate - 922 homes

Remarks: Under contract-accepting backup offers. Short Sale. Don’t miss the opportunity to own this one-of-a-kind, 3-bedroom, 2-bathroom, 2-car garage custom home. Upon arriving at the property, you are greeted by an oversized lot and mature trees in a quiet, well-established neighborhood. Inside, the home offers an open and split floor plan, cathedral ceilings, and an indoor/outdoor pool that flows from the back patio into the living room, adding a unique feature to this property—perfect for entertaining and allowing you to take a dip in any weather. On the left side of the home are two spacious bedrooms with large closets and a shared bathroom featuring a single vanity and a shower/tub combo. Moving to the right side of the house, you’ll find the master suite, loft, and kitchen. The master suite offers ample space and direct access to the pool area. The en-suite bathroom includes a garden tub and walk-in shower. The loft overlooks the living room and pool area and also contains two large storage spaces on either side, making storage accessible while serving as a great spot to watch a show and unwind. The kitchen features tile countertops and a small bar for additional seating. Right out back, the pool is enclosed in a full-screen cage with a large deck. The yard also boasts a shed for storage and plenty of space for activities. This home has so much to offer. Don’t wait—schedule your private showing today!

Listing is courtesy of: LPT REALTY LLC (386-388-7877)

Listing Agent: Trent Shackelford (941-518-7875)

Remarks: One or more photo(s) has been virtually staged. This is a 4 bedroom, 2 bathroom single family home with approximately 2,355 square feet on about 0.34 acres, a 2 car garage, a wood burning fireplace, and a screen enclosed pool and jacuzzi inside a gated community just minutes from Legoland. This home stands out for buyers who want strong square footage, a functional layout, and outdoor features that are already in place. The floor plan gives plenty of room for daily living, guests, or flexible use, and the 2 car garage adds practical storage and parking that matters for long term ownership. The gated setting brings added privacy and neighborhood appeal while keeping the property close to shopping, dining, schools, and the main conveniences that make this part of Winter Haven attractive. Inside, the home gives a buyer a solid starting point with the chance to update key finish areas over time. The kitchen and bathrooms are the main spaces where a future owner may choose to remodel, making this a value add opportunity for someone who wants to improve the home around an already desirable footprint. The wood burning fireplace adds character to the living area and helps give the interior more presence than a basic builder layout. This is the kind of house that works well for a buyer who wants size, location, and lifestyle features first, then the freedom to make design changes at their own pace. The outdoor setup is a major part of the appeal. The screen enclosed pool and jacuzzi create a more complete Florida living experience and give the backyard a true entertaining and relaxation element. The screened enclosure adds usability and helps the pool area feel like an extension of the home rather than just an extra feature. The pool is reported to be working, with the main noted item being a light, and seller will have the pool fully cleaned and ready to go. For buyers searching online for a Winter Haven pool home, a gated community home near Legoland, a house with jacuzzi and screened pool, or a Polk County property with indoor and outdoor living space, this home checks multiple search points that matter. Major system notes also help frame the opportunity clearly. The AC is reported at about 10 years old, the water heater about 2 years old, and the roof about 10 years old, with a prior note that inspection suggested roof replacement due to age and mentioned one small leak in a closet. The septic system was replaced, which is an important update for future maintenance planning. HOA is reported at approximately $550 a year, and rental restrictions are reported as no. For buyers looking for a 4 bedroom 2 bathroom home in Winter Haven, a gated neighborhood property near Legoland, or a Florida home with pool, fireplace, garage, and room to personalize, 215 Santa Rosa Dr presents a strong opportunity. SOME PHOTOS HAVE BEEN VIRTUALLY EDITED.

Listing is courtesy of: SILVER DOOR REALTY LLC (954-993-0696)

Listing Agent: Michelle Paez (954-589-0144)

Remarks: One or more photo(s) has been virtually staged. Welcome to this beautiful home in peace creek reserve! this thoughtfully designed single-story residence offers 4 bedrooms and 2.5 bathrooms, combining comfort and functionality. The open-concept floor plan seamlessly connects the family room, dining area, and kitchen—complete with a central island—creating the perfect space for everyday living and entertaining. Located in the desirable peace creek reserve community, residents enjoy a serene setting surrounded by nature, including a picturesque creek. situated in winter haven—known as the chain of lakes city with over 26 connected lakes—this area offers a variety of shopping, dining, and outdoor activities such as biking and water recreation. Peace creek reserve provides the perfect balance of a peaceful, small-town atmosphere with everyday convenience—an ideal place to call home.

Listing is courtesy of: GLASSTONE GROUP INC (321-988-4663)

Listing Agent: Barbara Cunha De Freitas (617-458-0838)

Remarks: Just reduced approx. $30,000 below appraised value to allow for remodeling! This 2 Bedroom, 2 Bath home is located in Brandy Chase Village, a well-maintained 55+ community with clubhouse and heated pool. This home is surrounded on each side by green space views and conveniently located directly across from the community center. Open floor plan. Large, screened porch on back with utility room as well as screened porch at entry. Includes assigned covered parking in front. NEW ROOF 2022 and home RE-PIPED in 2024. Residents can take advantage of the clubhouse for social gatherings and events plus enjoy the heated community pool. Besides the recreational facilities, the HOA includes lawn maintenance, trash, water and sewage. Schedule a tour today to see this charming home and community.

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

Listing Agent: Donna Sealy (863-206-5328)

Remarks: As you walk into this beautiful home, you are welcomed by a den/office on the right with double doors, which can easily be used as a third bedroom if desired. Continuing through the home, you’ll find a spacious formal dining room separate from the main living area. As you exit the dining room, the home opens up into a bright open-concept space featuring the living room, kitchen, and a cozy coffee/breakfast area, perfect for everyday living and entertaining. The gourmet kitchen features upgraded Kraft Maid cabinetry, Cambria quartz countertops, newer KitchenAid appliances, and a gas convection range, all overlooking the spacious living room with large windows and sliding glass doors that bring in plenty of natural light. The home offers three sliding glass doors that lead out to a large screened-in lanai, perfect for relaxing and enjoying the Florida lifestyle. The lanai also features an extended screened area with artificial turf. The spacious primary bedroom includes a walk-in California closet system and an en-suite bathroom with dual sinks, comfort-height vanity, separate toilet room, and a walk-in tiled shower. Throughout the home you will find crown molding, imported Italian tile flooring, engineered wood flooring, plantation shutters, and Hunter Douglas remote-control shades. Additional features include a laundry room with washer and dryer, double-pane low-E windows, an AO Smith hybrid water heater, Pelican salt-free water filtration system, gutters, and a stone exterior façade with a brick paver driveway and extended front walkway. The two-car garage features an insulated garage door, garage door opener, overhead storage racks, and a workbench area with pegboard and additional workspace. Located in the desirable Traditions 55+ gated community, residents enjoy resort-style amenities including a clubhouse, heated pool and hot tub, ballroom, craft room, meeting rooms, library, computer room, fitness center, tennis and pickleball courts, dog park, and more. Monthly HOA fees include lawn service, cable TV, internet, and exterior house painting.

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

Listing Agent: Stephanie Class Cordero (321-208-0378)

Remarks: Pre-Construction. To be built. Discover a home where modern comfort meets effortless style in the beautiful VillaMar community of Winter Haven. Surrounded by scenic lake views and resort-style amenities, this is more than a place to live—it’s a place to truly enjoy life. The Ventura floor plan offers up to 1,562 square feet of thoughtfully designed living space with 4 bedrooms and 2 bathrooms. At the heart of the home, the open-concept layout creates a bright and welcoming atmosphere. The beautifully designed kitchen features a large island with quartz countertops—perfect for gathering, entertaining, or enjoying everyday meals. It flows seamlessly into the spacious great room, where natural light pours in through upgraded windows, creating a warm and airy feel throughout. Your private primary suite, located at the rear of the home, offers a peaceful retreat. Enjoy a spacious walk-in closet, dual sinks, and a walk-in shower designed for both relaxation and ease. There are three other bedrooms and a full bath are tucked away at the front of the home, creating a private and functional space. Built with today’s lifestyle in mind, The Ventura includes smart home features such as a Ring Video Doorbell, Smart Thermostat, Keyless Entry Door Lock, and customizable DEAKO light switches—giving you control and peace of mind at your fingertips. Enjoy the amenities offered in the community with a resort style pool, playground and dog park. Experience the perfect blend of style, convenience, and community living at VillaMar. Your future home is waiting—make The Ventura your own and start creating lasting memories.

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: Vilmari Caraballo (407-583-9870)

Remarks: Very clean and well-maintained 4 bedroom, 2.5 bathroom two-story home located in desirable SE Winter Haven! Roof is only 2 years old!! This spacious property offers a functional layout perfect for both everyday living and entertaining. The large kitchen opens seamlessly to the family room, creating a welcoming central gathering space, and features ample oak cabinetry for plenty of storage. Ceramic tile flooring is featured in all wet areas for easy maintenance. Step outside to enjoy the fully fenced backyard—ideal for pets, play, or relaxing in your own private outdoor space. Conveniently located with quick access to Hwy 27 and a straight drive to I-4, making commuting a breeze. Just minutes from shopping, dining, and entertainment, including Eagle Ridge Mall, the Cypress Gardens area, and Legoland. Don’t miss this opportunity to own a spacious home with room to grow in a great location!

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Tony Acosta (863-224-5956)

Remarks: Under Construction. 2-story new construction townhome with 1,604 square feet, 3 bedrooms, and a covered lanai, located in the brand-new Harbor of Lake Henry community. Downstairs, enjoy an open layout(optional first floor layout with den)and a gourmet kitchen with, shaker-style wood cabinets, Samsung stainless steel appliances, including a pantry. The spacious gathering room opens to your covered lanai. The entire lower level and upstairs baths are finished with luxury vinyl plank flooring, with stain-resistant carpet in the bedrooms. Upstairs, you'll find three spacious bedrooms including your owner's suite complete with a walk-in wardrobe, linen closet, and a private en-suite bath with dual vanities and a tiled shower. Additional features for your convenience include a half bath downstairs, upstairs hall bath for the secondary bedrooms, energy-efficient insulation and windows, and a full builder warranty.

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

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

Remarks: The property you are inquiring about is located in Winter Haven, FL, in the Park Lake area of Polk County. This is an amazing opportunity for anyone wanting to be close in one single floor, walkable distance to almost everything, and is ready to move into. This is a 2-bedroom, 2-bath home with 1,224 sq.ft. plus a single-car garage, and has been updated. Text, call, and see it today. *Agents, please MLS remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: Under contract-accepting backup offers. Discover this charming 4-bedroom, 2-bath home with 1,840 sqft of comfortable living space in the highly desirable Ruby Lake neighborhood in Southeast Winter Haven. Located near LEGOLAND®, this home offers both convenience and a great sense of community. Enjoy the generous bedrooms, including a comfortable primary suite, plus a backyard ready for play or entertaining! With a fantastic location near schools, shopping, and parks, everything you need is just minutes away. Don’t miss the chance to make this lovely Ruby Lake home yours—schedule a tour today!

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

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: Short Sale. MAKE AN OFFER ON This better than new construction stunning 4-bedroom, 3-bathroom home is just 2 years young and beautifully maintained—ready for you to move right in! Step into a bright and spacious open-concept layout featuring luxury vinyl flooring throughout, soaring high ceilings, and a seamless flow between the living room and kitchen. The kitchen boasts elegant cabinetry, sleek countertops, and modern finishes. Energy-efficient solar panels help keep utility costs low, and the property is fully enclosed with a new vinyl fence for added privacy. The master suite offers a spacious walk-in closet and a spa-like bathroom complete with an extended walk-in shower, dual sink vanity, and a dedicated towel closet. A second bedroom features its own private ensuite, while a third full bathroom is ideal for guests or inlaws. Relax in your fenced in back patio and enjoy the peace and privacy of your surroundings. Conveniently located near shopping where more stores are being built like a new Target, dining, hospitals, schools and top Central Florida attractions—Legoland is 15 minutes away--this home has it all and more. Don’t miss the opportunity to make it yours!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Marisol Rivera (407-607-5201)

Remarks: Under contract-accepting backup offers. Discover the potential of this 3-bedroom, 2-bathroom home in Winter Haven, offering a versatile layout with a combined living and dining room perfect for everyday living or entertaining. The property features a fenced-in backyard, a spacious yard with room to customize, an empty pool ready for renovation or removal, and an enclosed back porch that adds extra flexible living space. With solid bones and plenty of opportunity to make it your own, this home is ideal for buyers looking to personalize a property in a desirable location.

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: Jana Lutz (863-602-8992)

Remarks: ***PRICE REDUCTION*** Refined luxury meets modern efficiency in this stunning 4-bedroom, 3-bath home located in the private gated community of Hampton Cove, tucked away on a peaceful cul-de-sac, accented by elegant brick exterior detailing. Designed for both sophistication and comfort, this meticulously upgraded home offers timeless finishes, flexible living spaces, and exceptional energy efficiency. Inside, luxury vinyl plank flooring flows throughout, complemented by granite countertops in every space. The chef-inspired kitchen is beautifully appointed with stainless steel appliances, rich granite surfaces, a designer backsplash, deep drawer storage, and soft-close cabinetry, a breakfast bar, and a sunlit dinette-creating a space that is as functional as it is striking. A dedicated dining room provides the perfect setting for hosting and formal gatherings. The primary suite serves as a serene retreat, featuring a private sitting area and a spa-style en-suite bath with a soaking tub and walk-in shower. Bedrooms two, three, and four are generously sized, offering comfort and flexibility for family, guests, or additional work-from-home needs. Both guest bathrooms are thoughtfully designed with walk-in showers, offering elevated comfort for family and guests alike. A versatile flex room allows effortless customization—ideal for a private office, fitness studio, or creative space. Outdoors, the expansive fenced backyard provides abundant room for a resort-style pool, with a strategically located bathroom perfectly suited for future pool access. This home is enhanced with top-tier systems and energy-conscious upgrades, including: • Lennox 19.5 SEER high-efficiency A/C (2018) with damper system and four thermostats • Fully paid solar panels • 16kW whole-home Generac generator powered by natural gas • Hybrid water heater (2018) • Roof, A/C, and water heater replaced in 2018 • Energy Recovery Ventilator (ERV) in the garage for improved air quality and humidity balance • Double-pane windows throughout • Backyard fencing added in 2023 • Washer and dryer (2025) included. This exceptional home delivers luxury, resilience, and efficiency in one elegant package—an opportunity rarely found.

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

Listing Agent: Jessica Willaford (863-662-8549)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2018, offering the perfect blend of modern comfort and Florida lifestyle living. From the moment you step inside, you’ll appreciate the open-concept layout, ideal for both everyday living and entertaining. The spacious kitchen flows seamlessly into the living and dining areas, featuring contemporary finishes, ample cabinetry, and plenty of natural light throughout. The living area is enhanced by a stylish built-in electric fireplace, creating a warm and inviting focal point. This thoughtfully designed single-story home features a spacious primary suite with a private bath and walk-in closet, along with three additional bedrooms that offer flexibility for family, guests, or a home office. Step outside and enjoy your private backyard space—perfect for relaxing evenings or weekend gatherings. The garage is equipped with a mini-split air conditioning system, adding comfort and versatility for a workspace, gym, or additional storage. Located in a desirable community with private access to Lake Eloise, part of the renowned Winter Haven Chain of Lakes, you’ll have endless opportunities for boating, fishing, and enjoying the water just minutes from your doorstep. Plus, you’re just 10 minutes from LEGOLAND Florida Resort, making this location perfect for both everyday convenience and fun-filled weekends. Conveniently situated near shopping, dining, and major roadways, this move-in-ready home offers the ideal combination of location, lifestyle, and value. Schedule your private showing today and experience everything this home has to offer!

Listing is courtesy of: CLARK REALTY LLC (863-345-2155)

Listing Agent: Ty Dennis (863-651-8328)

Remarks: Lake Ashton is a 55+ golf community with all the amenities you could ask for including movie theatre, bowling alley, pickle ball, tennis, bocce, fitness centers, two clubhouses and so much more! This highly upgraded 3-bedroom, St John floor plan home is breathtaking! Once inside the elegant beveled double French glass door entry you will be amazed at the impeccably executed home finish. Such as, round columns frame the dining area, while raised archways lead to the kitchen and breakfast nook. The great room features coffered ceilings with recessed lighting, 8’ triple sliders that open to the lanai, a ceiling fan, and crown molding that flows throughout the home. The kitchen boasts a bank of drawers, 42" raised-panel custom cabinets with crown molding, stainless steel appliances, granite countertops, pendant lighting, and a breakfast bar. This home has split plan for privacy. Wake up to serene views from your primary bedroom, complete with sliding doors to the lanai. The en-suite bath features two walk-in closets, a walk-in shower, double vanities, a soaking tub, and a linen closet. The large, screened lanai overlooks the 13th hole has pond and nature views. There is also the Health and Fitness center which has an indoor pool, sauna, racquet ball and basketball, for your enjoyment. There are so many more amenities, clubs, activities, dances, and entertainment. Don't miss out on the opportunity to live in Lake Ashton, Central Florida's premier 55+ active adult resort style living community. This is a must see to appreciate home and community! SELLER MOTIVATED!!!

Listing is courtesy of: HEROES REAL ESTATE GROUP LLC (407-947-6420)

Listing Agent: Armando Perez (407-947-6420)

Remarks: One or more photo(s) has been virtually staged. Discover this exceptional investment opportunity in the thriving city of Winter Haven! This spacious and well-maintained 2-bedroom, 1.5-bath apartment offers the perfect blend of comfort, location, and long-term rental potential. Ideal for investors seeking stable returns, this unit comes equipped with all appliances, including an in-unit washer and dryer, providing added convenience and desirability for future tenants. Perfectly situated, the property is only 5 minutes (approx. 3 miles) from the world-renowned Legoland Theme Park, making it highly attractive for families and professionals relocating to the area. You’ll also be just minutes from Port 27, Winter Haven’s newest lifestyle and entertainment destination located on Lake Hamilton, featuring waterfront dining, recreation, and a growing selection of family-friendly activities. Inside, the unit offers a functional layout with comfortable living spaces, natural light, and low-maintenance living—an excellent advantage for landlords. Whether the intended use is long-term leasing or adding a turnkey property to an investment portfolio, this apartment checks all the boxes. Winter Haven continues to experience strong residential growth, fueled by its central location, access to major highways, beautiful chain of lakes, and expanding entertainment and commercial developments. This upward trend makes the area highly appealing for long-term renters and a promising market for investors. Don’t miss the chance to secure a property in one of Central Florida’s most dynamic and fast-growing communities. This is a solid investment you’ll want to add to your portfolio!

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

Listing Agent: Yuliescar Mendoza (321-402-6564)

Remarks: Under contract-accepting backup offers. Turnkey Duplex Investment, reliable Income, renovated, & low maintenance. Excellent opportunity to acquire a fully rented, income-producing duplex in a convenient Winter Haven location. This solid block construction property features two spacious 2-bedroom, 1-bath units, each with a well designed, functional layout that tenants love. The property has been recently renovated, including fresh interior paint and new appliances, offering a clean, modern feel and minimizing near-term maintenance expenses. Both units are occupied by reliable, long term tenants, providing immediate and steady cash flow from day one. Strong rental demand in the area, combined with the property's durable block construction, great location, and updated interiors, makes this an ideal addition to an investor's portfolio, whether you're a seasoned buyer or looking for your next low-hassle income property. To respect tenant privacy, property may be previewed once under contract. Do not disturb tenants. Key Highlights: Duplex with 2 bed / 1 bath on each side Fully occupied with dependable tenants in place, Newly renovated: paint & appliances, Block construction for durability and longevity, Nice, efficient layouts, Great location with continued renter demand. Turnkey investment with steady income

Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (727-898-6800)

Listing Agent: Mary Lannin (231-883-2286)

Remarks: NEW PRICE POINT, REDUCED!!! HURRY TO SEE THIS TRUE LAKEFRONT ON THE BEAUTIFUL CHAIN OF LAKES!!! Sunsets are magnificent from the screened & tiled lanai! Lake Lulu is a quiet lake on the Chain with wildlife and an abundant array of birds in a serene & tranquil setting. You can pull your boat up directly behind your 2bedroom 2.5 bath waterfront townhome! This home has been remodeled and offers two large primary suites with remodeled en-suite bathrooms. The kitchen is open & bright with a newer refrigerator, newer hot water heater, new windows. All of these items have been replaced within the past 6 months. You'll like the tile floors throughout for easy maintenance, an electric fireplace and the home is tastefully decorated with a neutral color scheme. Enjoy boating, fishing & lakefront living from this centrally located gem! The property also has a one-car garage and is close to the community pool for swimming and recreation. Walk to Publix and shopping and just minutes to medical and LEGOLAND. Call today for an appointment to see all this townhome has to enjoy!!

Listing is courtesy of: THE K TEAM REAL ESTATE SERVICES LLC (863-604-1601)

Listing Agent: Cathy Kluytenaar (863-604-6220)

Remarks: One or more photo(s) has been virtually staged. Under Construction. The first floor of the stunning Edison two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom. 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: ***Price Adjustment***Gated Community! Welcome to this Beautiful 4BR/3BA Home with Hardwood throughout, with ceramic tile in wet areas, HEATED Inground Swimming Pool with Water Fountain! NEW Roof (2023); Recent A/C, Water Heater, Pool Motor and Hot Water System Replacements; also, Interior and Exterior Recently Painted. New TECO Sensi Smart Digital Thermostat to save you energy and by using the Sensi App you can manage your home's temperature from anywhere. It is nestled in the gated Terranova community, this beautiful home features well-maintained landscaping, extra High Ceilings with crown molding in Foyer, Living Room, Dining Room, Kitchen Nook and Family Room, 4 bedrooms, 3 full bathrooms, with a good size master suite with a walk-in closet, jacuzzi, and shower; Other highlights include a screened-in deck and an oversized lot with a PVC privacy fence. At .29 acres, the backyard is one of the largest in the community, offering significant flexibility for future use. The formal living and dining areas, cozy breakfast nook, and family room are spacious and perfect for gatherings. Additionally, the water well sprinkler system provides year-round savings, particularly during the summer months. Note: "Some Furniture is available for sale".

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Raquel Hernandez (863-662-0910)