Winter Haven Homes For Sale & Real Estate - 969 homes

Remarks: Mediterranean Revival residence combining historic charm, remarkable updates, and an ideal Central Florida location. Welcome to 1806 17th St NW in the "Chain of Lakes City" of Winter Haven. Discover this beautifully restored and extensively renovated Spanish bungalow, thoughtfully updated in 2021–2022 while preserving its timeless character. Major system improvements include a new roof, new electrical, new plumbing, new HVAC systems with ductwork, and a well-fed sprinkler system—rare peace of mind for a historic home. Additional upgrades include refinished hardwood floors, replastered and retextured walls, remodeled kitchen and baths, fresh interior and exterior paint, Tiffany-style fans, and period-inspired lighting. With city water and sewer, this historic property offers the charm of another era without sacrificing modern convenience. Ideally positioned across from Lake Cannon and near Lake Mirror on the scenic Winter Haven Chain of Lakes, the home is surrounded by tree-lined streets, beautifully preserved residences, and refreshing lake breezes. Curb appeal shines with textured stucco, arched windows, mature palms, and an oversized double lot. A covered two-car carport, new concrete driveway, detached workshop, and professional landscaping complete the exterior setting. Inside, warm and inviting living spaces are filled with architectural detail and authentic character. The formal living room features Saltillo tile floors, beadboard ceilings, and arched windows overlooking lush gardens. Nearby, the family room showcases original hardwood floors, a coved ceiling, and a gas-burning brick fireplace. A cozy computer nook creates the perfect work or study space. The formal dining room highlights softly curved ceilings, arched transitions, and charming glass-front corner built-ins. The updated kitchen blends vintage styling with modern function, featuring wood cabinetry, soft-close drawers, granite countertops, stainless steel appliances, and a walk-in pantry with laundry connections. Three bedrooms and two beautifully remodeled baths include a private primary suite with French doors opening directly to the rear patio. Outdoor living is equally impressive, offering a secluded patio and expansive backyard ideal for entertaining, gardening, or simply relaxing beneath the shade of mature landscaping. The detached 18x19 workshop with roll-up door, electricity, and concrete slab provides exceptional flexibility for woodworking, hobbies, storage, or creative space. Located just minutes from downtown Winter Haven, shopping, dining, medical facilities, and major highways, this move-in-ready historic residence also offers convenient access to public boat ramps and the full Chain of Lakes lifestyle. A rare opportunity to own a thoughtfully restored Spanish bungalow where timeless architecture and modern upgrades blend seamlessly.

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

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

Remarks: **MOTIVATED SELLER** FRESH INTERIOR PAINT (2026) NEW WATER HEATER (2026) NEW A/C COMPRESSOR (2026) NEW ROOF (2025) NEW A/C (2020). This charming Devon Pool home is ready to welcome you HOME! The freshly painted interior offers a blank canvas just waiting for your personal touch. The inviting landscaping catches your eye as you arrive, and inside you’re greeted by bright, open spaces with views of the beautifully maintained pool "JUST IN TIME FOR SUMMER". Located in the Lake Ashton community, this home blends comfort, accessibility, and resort-style living. Enjoy the versatile den that can serve as an office, craft room, or more add to its appeal. The extended kitchen features a bay window with scenic pond views, while the primary bedroom has private lanai access and an en suite with dual vanities, a walk-in shower with grab bars, and pocket doors for convenience. Outside, relax in your screened-in solar-heated pool, overlooking peaceful green space and the pond. Hurricane shutters surround the home, with two motorized screens on the lanai for added safety. Have peace of mind with two gated entrances with 24/7 guard service and a stunning clubhouse with a grand ballroom, movie theater, bowling lanes, and on-site dining at Charm City and Eagle Nest. Stay active with indoor and outdoor pools, fitness centers, racquetball, tennis, pickleball, bocce, shuffleboard, and more. Whether relaxing or staying active, this home has it all.

Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)

Listing Agent: Candra Alston (407-257-5204)

Remarks: Significant price improvement and a highly motivated seller make this an exceptional opportunity in the sought-after 55+ Brookhaven Village community. This well-maintained manufactured home is truly move-in ready and offers both comfort and value. Major updates provide peace of mind, including a new roof installed in October 2024, fresh interior paint completed in March 2025, and an HVAC system replaced in 2022. Inside, you’ll find a bright and spacious layout featuring two bedrooms and two full bathrooms, a generous living area, and a welcoming enclosed Florida room — perfect for relaxing or entertaining year-round. The home also includes updated tie-downs and sits on a desirable corner lot, offering additional space and privacy. Residents enjoy low HOA fees and access to community amenities such as a heated pool, clubhouse, shuffleboard courts, and RV parking area. Conveniently located near I-4, with easy access to Legoland, Disney, shopping, dining, and medical facilities, this home combines lifestyle, location, and affordability. Opportunities like this don’t last — schedule your private showing today.

Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)

Listing Agent: Adriana Morales (407-860-8867)

Remarks: Welcome to this spacious home Located in the gated community of The Gardens, this spacious 4-bedroom, 2-bath home offers an open layout designed for comfortable living and entertaining. The large primary suite features a tray ceiling, two walk-in closets, dual sinks, a tile shower, and a garden tub. Step outside to enjoy a generous backyard with an outdoor kitchen/BBQ area, above-ground pool, storage shed, and plenty of room to relax or entertain.

Listing is courtesy of: ORCHARD BROKERAGE, LLC (844-515-9880)

Listing Agent: Ray Garza (407-607-9382)

Remarks: Welcome to this move-in-ready home 3 Bedroms, 2 Bathrooms. This beautifully maintained residence offers a spacious and functional floor plan, featuring modern finishes and an abundance of natural light throughout. The heart of the home boasts a contemporary kitchen with ample cabinetry and sleek appliances, overlooking an expansive living area perfect for entertaining. Retreat to the generous primary suite, complete with a private en-suite bath and walk-in closet. Step outside to find a sizable backyard, offering endless possibilities for outdoor living and relaxation in the Florida sun. Situated in the growing city of Winter Haven, you are just minutes away from world-class attractions like LEGOLAND, premier golf courses, and the famous Chain of Lakes. This home combines comfort, style, and a prime location—schedule your private showing today and discover your Florida dream!

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

Listing Agent: Maria Gomez Arevalo, Pa (407-705-7203)

Remarks: Move-in Ready! Welcome to the Residences at Winter Haven, a premier new single-family community designed for those who value both quality and connection. Set within this inviting neighborhood, the Crystal River Gen Suite floor plan brings a versatile elegance to everyday living. The open layout is anchored by a stunning gourmet kitchen featuring a waterfall island, while a private Gen Suite offers ultimate flexibility and independence with its own entrance, bath, and kitchenette. It’s a lovely modern space that’s ready for you to make it your own.

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

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

Remarks: Welcome to 2235 Lakeridge Estates, your opportunity to enjoy the Florida lifestyle in one of Winter Haven's growing and desirable communities near scenic Lake Hartridge and the Beautiful Winter Haven Chain of Lakes. An exceptional opportunity to own a beautifully designed home in the heart of Winter Haven. Nestled within the desirable Lakeridge Estates community near scenic Lake Hartridge, this well-maintained 3-bedroom, 2-bathroom residence offers nearly 1,893 square feet of thoughtfully designed living space, blending comfort, functionality, and Florida lifestyle appeal. From the moment you arrive, you’re greeted by a welcoming entry that opens into a bright, open-concept floor plan featuring vaulted ceilings and a seamless flow between the living and dining areas—perfect for both everyday living and entertaining. The spacious kitchen is a standout, complete with stainless steel appliances, ample cabinetry, a center island, and a pantry, making it as practical as it is stylish. The split-bedroom layout offers privacy and comfort, with a generously sized primary suite featuring a walk-in closet and an en-suite bath with dual features designed for relaxation. Two additional bedrooms provide flexibility for guests, family, or a home office. Step outside to one of this home’s most desirable features—a spacious backyard, ideal for outdoor gatherings, pets, or creating your own private oasis. The covered rear porch extends your living space outdoors, capturing the essence of Florida indoor-outdoor living. Location is key, and this home delivers. You’re just minutes from everyday conveniences including shopping destinations, along with casual dining options. Beyond daily conveniences, Winter Haven is known for its vibrant charm and attractions. Enjoy weekends exploring the nearby Chain of Lakes, or take a short drive to world-renowned destinations like LEGOLAND Florida Resort, a major area highlight for entertainment and recreation. The revitalized downtown district offers local boutiques, dining, and community events, adding to the area’s growing appeal. Whether you’re a first-time buyer, growing household, or investor, 2235 Lakeridge Drive presents a compelling blend of space, location, and lifestyle—an inviting place to call home in one of Central Florida’s most steadily growing markets.

Listing is courtesy of: LA ROSA REALTY CENTRAL FLORIDA LLC (407-861-8009)

Listing Agent: Maria Elena Fernandez (407-704-0732)

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: Under contract-accepting backup offers. Hidden gem with upgrades you won’t expect! First-floor condo for easy access and numerous updates throughout. The kitchen features a new backsplash, new sink and faucet, freshly painted cabinets, and newer appliances, including the refrigerator and dishwasher. A new water heater adds additional peace of mind. Both bathrooms have been updated with new vanities, faucets, and tile backsplashes. Custom wood shelving has been installed throughout the home—no wire shelving—along with custom closet organizers in both bedrooms. The spacious primary bedroom features beautiful plantation shutters. Stylish barn doors enclose the laundry area with a washer and dryer, and the hall closet. Covered parking included. Situated on scenic Lake Howard, part of the famous Winter Haven Chain of Lakes, this community offers boat dock access. Residents also enjoy a sparkling pool, gazebo with grilling area, shuffleboard courts, and a quiet, secure atmosphere. Even better, the HOA covers cable, internet, water, sewer, trash, exterior maintenance, and lawn care—you only pay for electricity. Truly affordable, maintenance-free Florida living.

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

Listing Agent: Nancy Cini (727-612-0375)

Remarks: One or more photo(s) has been 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: NEW CONSTRUCTION! This brand-new single-story, two bedroom, two bath Villa is located in Vienna Square, a 55+ gated community in Winter Haven. Live a low maintenance lifestyle with tranquil views from your screened lanai which is accessible from the villa’s open floor plan. This villa features a two car garage, paver driveway, granite counter tops, shaker cabinets, new Whirlpool appliances, Delta fixtures, designer lighting, inside laundry and more. In the owners retreat, there is a walk-in closet and tiled walk-in shower. The guest bathroom has a tub/shower combo. Lawn maintenance and most exterior maintenance are included in the monthly HOA dues, along with Spectrum basic cable/internet, access to the clubhouse, heated pool, fitness center, and more. This new home comes with a structural warranty. Call today!

Listing is courtesy of: DGCF REALTY ADVISORS LLC (877-791-9907)

Listing Agent: Austin Schreiber (863-287-8877)

Remarks: Beautifully Maintained Home in Winter Haven! This stunning property shows just like a model home! The owners have kept it immaculately maintained and spotlessly clean. Built in 2023, everything is practically brand new, offering true peace of mind. This 4 bedroom 2.5 bath home has an Open-Concept Living area, Kitchen and Dinning that are perfect for everyday living and entertaining. Modern Kitchen: Features up-to-date finishes, including beautiful granite countertops and durable tile flooring. Move-In Ready: All appliances, including the washer and dryer, stay with the home! Brinks home security system for added peace of mind. All bedrooms and laundry including the spacious primary suite, are conveniently located upstairs. The primary bedroom floods with natural light and features a beautiful en-suite bathroom with a walk-in shower and a generous walk-in closet. Situated on a large corner lot, the backyard is completely fenced-in and features a double gate for easy access. The Lanai is ideal for hosting family and friends for a cookout. Best of all, this community has NO CDD and a low HOA fee! Prime Location Located in a highly desirable area of Winter Haven, you'll be just minutes away from the new Target, excellent shopping, dining, and LEGOLAND! Priced to move, Welcome Home!

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

Listing Agent: Rose Cayson (863-559-4360)

Remarks: Short Sale. $50,000 PRICE REDUCTION! Welcome to your perfect retreat in this exclusive gated community, where tranquility meets convenience! Enjoy easy access to shopping, dining, and the exciting attractions of Winter Haven, including Legoland Theme Park, all just minutes away. This charming three-bedroom, two-bathroom home features a modern open-concept layout and a split bedroom design for added privacy. You'll love the luxury vinyl flooring throughout the living areas, with cozy carpet in the bedrooms. Step outside to your large, fully fenced backyard—perfect for relaxation without any rear neighbors. Unwind in your spacious screened-in lanai, ideal for enjoying the outdoors year-round! Additional highlights include an 8 x 5 fireproof storage closet in the garage, providing peace of mind for your valuables, as well as a well-maintained irrigation system and beautiful landscaping that enhances the curb appeal. With quick access to the Polk Parkway and Interstate 4, Central Florida adventures are at your fingertips. Don’t miss out on this fantastic opportunity—schedule your showing today!

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

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

Remarks: 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: Under contract-accepting backup offers. Short Sale. Packed with potential! This spacious two-story home, featuring 4 bedrooms, 2.5 baths, and a versatile bonus room needs some repairs, cleaning, and TLC, but that’s where the attractive price comes in! The main floor includes a large great room, white kitchen with granite countertops, front living room/den, laundry, enclosed bonus room and a 3-car garage. The lanai offers a great outdoor entertaining space. Upstairs, the primary suite offers dual sinks, tub and separate shower, and dual walk-in closets, and the other bedrooms. Not in a flood zone and low HOA fees of $165/year ensure long-term low cost of ownership. Trustee Sale, must sell!

Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)

Listing Agent: Tanja Cisliek (727-480-4155)

Remarks: NOW OFFERING A HOME WARRANTY! Your opportunity to own in the highly sought-after Cypresswood Golf & Country Club just became even more appealing. Welcome to The Tennis Villas, where gated security, resort-style amenities, and maintenance-friendly living come together in one of Central Florida’s premier golf communities. A charming wrought iron gate welcomes you into a private front courtyard patio, creating the perfect space to enjoy morning coffee, entertain guests, or simply relax in privacy. Inside, this well-maintained 2-bedroom, 2-bath villa offers spacious living and dining areas with laminate flooring, an open-concept layout, and thoughtful features designed for comfortable Florida living. The bright kitchen features updates, ceramic tile flooring, and flows seamlessly into the main living space, complete with a wet bar and additional cabinet storage—ideal for entertaining. A bonus Florida room with air conditioning overlooks a peaceful open field and pond, providing tranquil views and additional year-round living space. The primary suite offers direct access to the enclosed lanai through sliding glass doors, creating a relaxing retreat with serene backyard views. Recent improvements include a NEW metal roof for added value and peace of mind. Enjoy truly low-maintenance living with HOA services that include exterior painting, roof maintenance, lawn care, and pest control, allowing you more time to enjoy everything Cypresswood has to offer.Community amenities include:?• 18-hole championship golf course designed by Ron Garl?• Junior Olympic-sized swimming pool?• Lighted tennis courts?• Fitness center and clubhouse with pro shop?• On-site restaurant and event space Whether by golf cart, bicycle, or a short walk, all amenities are conveniently nearby. Ideally located just minutes from Highway 27, I-4, Legoland Florida Resort, the Polk Parkway, shopping, dining, and medical facilities, this villa offers both convenience and lifestyle. Don’t miss your chance to enjoy affordable country club living in a secure, beautifully maintained community. Schedule your private showing today and experience the Cypresswood lifestyle for yourself.

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

Listing Agent: Corinna Weaver (863-258-2901)

Remarks: Under contract-accepting backup offers. 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: One or more photo(s) has been virtually staged. Behind the gates of Winterset, one of Winter Haven’s most sought-after lakefront communities, this 3-bedroom, 2-bath home built in 2006 offers 1,994 SF of comfortable living space. A covered, screened front porch welcomes you into a spacious great room that opens to a 550 SF screened rear porch with beautiful porcelain tile, ideal for indoor-outdoor living. NO Carpeting throughout, durable laminate flooring in 2020 was placed in the entire house. The split floor plan includes secondary bedrooms, sharing a hall bath with tub and linen closet. Inside laundry room includes washer and dryer, new water heater (2026), HVAC is 2021. Additional features include a tile roof with a brick paver driveway, 2-car garage and a garage screen door, offering added ventilation and flexible use of the garage. Situated on a large corner lot, this home provides added space and privacy.. Winterset community amenities include a lakefront clubhouse overlooking Lake Winterset, heated pool and spa, tennis and pickleball courts, shuffleboard, and a private boat ramp with access to Lake Winterset, part of the renowned Winter Haven Chain of Lakes. HOA fees include exterior maintenance, grounds maintenance, security, and access to all community amenities. Conveniently located near LEGOLAND® Florida, shopping, dining, and medical facilities. Centrally positioned between Tampa and Orlando with easy access to theme parks, beaches, and airports, this home offers comfort, natural beauty, and resort-style living in a peaceful, gated community.

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

Listing Agent: Laura Slocumb (863-660-7000)

Remarks: Short Sale. Short Sale. Looking for a nice home with amazing potential and opportunity to gain equity? This one may be IT for you! Welcome to this 3-bedroom, 2-bath move-in ready home located in the peaceful and sought-after SE Winter Haven area! Situated on an OVERSIZED corner lot, this home features a fully fenced backyard, high ceilings, and ceramic tile flooring throughout the main living spaces. You’ll love the screened-in lanai and Private Pool—perfect for relaxing or entertaining year-round. The kitchen boasts custom cabinetry, a cozy dinette with wraparound windows, and direct access to an oversized garage. The spacious master bedroom features a walk-in closet, while the additional bedrooms are ideal for family or guests. This home has AMAZING POTENTIAL and nestled in a quiet, well-kept neighborhood, just minutes from Legoland and all of Central Florida’s top attractions. Call today to schedule your private showing—this home is priced to sell and won’t last long!

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

Listing Agent: Krichely Gonzalez Rodriguez (407-953-4377)

Remarks: Spacious Single-Story Block Home with Endless Potential! Nestled in a quiet, established neighborhood close to Polk State College with no HOA, this solid single-story block home immediately catches the eye with its charming blend of stucco and natural multi-colored stone accents. Boasting 1,678 square feet of comfortable living space (2,527 square feet total), the interior features a generously sized layout including three spacious bedrooms and two bathrooms. The primary suite is a true retreat, complete with a walk-in closet for ample storage. At the heart of the home, a large kitchen and dining area provides the perfect setup for family gatherings and entertaining. Step outside onto the oversized 0.26-acre lot, where the backyard offers a private oasis featuring mature, producing fruit trees, a handy detached storage shed, and a solid privacy fence running across the rear property line. Perfectly situated in a desirable community zoned for great local schools, this property has incredible bones and just needs some updating and TLC to truly shine. The seller is highly motivated and ready to see your offers—bring your design ideas and schedule your private showing today to unlock this home's immense potential!

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

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