Winter Haven Homes For Sale & Real Estate - 969 homes

Remarks: NATURE CALLS, flies, and strolls by this beautiful NEW CONSTRUCTION Villa. Complete, and ready for its 1st happy homeowner. Bright, fresh, and relaxing 2 bedroom 2 bath with 2 car garage. The beautifully finished kitchen comes complete with a full stainless steel appliance package, granite tops, and modern gray cabinets. These lovely cabinets, and countertops also complement both the primary bath, and the guest bathroom. Neutral colors offer a nice finish to this well designed floor plan. Enjoy the privacy from your screened patio with no back door neighbors. Easy living awaits without the big worries. Exterior paint, roof replacement, irrigation water, yard maintenance, and Spectrum Internet/TV package is included in the reasonable monthly fees. Enjoy the social activities with the neighbors, splash in the community pool, or make a hit on the tennis/pickleball courts. The convenient location, and reasonable monthly fees makes this 55+ community an easy choice. Step inside, fall in love. Make it yours!

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: Marti Sutton (863-206-0563)

Remarks: UNDER MARKET VALUE!!! Brand NEW AC Fan motor, AC Amp Fuse and AC capacitor installed May 2026. Brand NEW fire/carbon monoxide detector alarms throughout the home. Welcome home to this beautiful 2-bedroom, 2-bathroom golf villa nestled within the beautiful Cypresswood Golf and Country Club in Winter Haven, Florida. Property is steps away from the golf clubhouse!!! Home features a stunning Florida room, ready for relaxation. Dry bar with sink in living room perfect for entertaining your guests. Step out to your outside patio for even more enjoyment. With access to golf, clubhouse, Restaurant, pool and recreational facilities, this home offers a low-maintenance lifestyle in an active and vibrant community. Legoland attraction is approximately 5 miles. Disney World, Orlando and Tampa attractions are within 30-60 minute driving distance. Opportunities like this don’t last long, Just buy and move in!!! CLEAN TITLE WITH NO LIENS. Property being sold AS-IS. ALL interior contents and furniture convey with the property.

Listing is courtesy of: SUCCESS INVESTMENT REALTY (407-304-0490)

Listing Agent: Bill Sprys (407-574-9724)

Remarks: Perfectly situated on a beautiful pond lot, this stunning 4-bedroom, 2-bath home offers over 2,000 square feet of thoughtfully designed living space and was JUST BUILT IN 2024. PAID OFF SOLAR PANELS! Why wait to build when you can move right into a like-new home with upgrades already done? Villamar is a wonderful new home community in Southeast Winter Haven offering a impressive resort-style community pool and playground. Location is key, this home is convenient to everything Winter Haven has to offer including a brand new Publix store opening soon just about 2 miles away! Step inside to discover an open and inviting floor plan with beautiful vinyl plank flooring, featuring a spacious kitchen with a large center island that overlooks the dining and living areas—perfect for entertaining family and friends. The kitchen is also upgraded with granite countertops and attractive stainless-steel appliances. The private owner's suite is tucked away at the rear of the home and features a generous walk-in closet and a spacious en-suite bathroom. The owner has added FULLY PAID OFF SOLAR PANELS AND A WHOLE HOME WATER FILTER AND SOFTENER! Enjoy Florida living year-round from the covered and screened lanai, an ideal space for relaxing while taking in your scenic pond views. The two car garage features an ELECTRIC CAR CHARGER AND EPOXY FLOORING! The fully fenced backyard provides privacy and plenty of room for outdoor enjoyment, making this home the perfect blend of function and style. Schedule your private showing today!

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

Listing Agent: Zachary Lay Llc (407-988-6342)

Remarks: Fully Renovated! Discover the perfect blend of modern upgrades and timeless charm in this beautifully updated 5-bedroom, 3-bathroom home. Featuring a brand-new kitchen, updated living spaces, new flooring throughout, and completely renovated bathrooms, this property is truly move-in ready. Recent upgrades include a new roof (2024), new electrical panel, new water heater, fresh interior and exterior paint, and all-new lighting and ceiling fans. The kitchen is a standout, showcasing quartz countertops, new cabinetry, stainless steel appliances, and modern finishes. Enjoy the warmth of a cozy wood-burning fireplace or step outside to your private oasis with a resurfaced pool and a spacious, fully fenced backyard—perfect for entertaining or relaxing. Located between Orlando and Tampa with no HOA or CDD, this home offers flexibility, freedom, and excellent investment potential. Conveniently close to major highways, theme parks, shopping, and dining. Short-term rentals are allowed, making this a great opportunity for both homeowners and investors.

Listing is courtesy of: GARCIA REALTY GROUP (407-920-3616)

Listing Agent: Erika Pinto (407-460-4097)

Remarks: Sitting on Lake Jessie and on a beautiful lot along the Winter Haven Chain of Lakes, this property offers an incredible opportunity to own waterfront living at an affordable price point. Known as the “Chain of Lakes City,” Winter Haven features dozens of interconnected lakes perfect for boating, fishing, watersports, and enjoying the true Florida lifestyle. Whether you’re looking for a full-time residence, seasonal snowbird retreat, or a smart long-term investment opportunity, this home is priced right for someone ready to make a few updates while securing a spot on the highly desirable main Chain of Lakes. Opportunities like this are becoming harder and harder to find. The home includes a metal roof, updated AC system, and updated plumbing, giving you a solid foundation to make it your own. The oversized lot provides plenty of extra driveway space and room to add a large garage or additional storage for boats, trailers, or recreational vehicles. Relax and unwind in the screened-in area while enjoying the peaceful lake breeze and beautiful waterfront surroundings. With endless potential and a low price, this property is a rare chance to create your dream lakefront getaway without breaking the bank.

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

Listing Agent: Keith St. Onge (863-651-1397)

Remarks: Under contract-accepting backup offers. Check out this well-maintained 4-bedroom, 2-bath home featuring a desirable split floor plan, built in 2002 and situated on a spacious half acre fully fenced lot. The home offers vinyl plank flooring throughout, providing a modern look and easy maintenance. The roof was replaced just 3 years ago adding peace of mind for the next owner. The property is on septic, offering lower utility costs. Enjoy plenty of outdoor space for pets, entertaining, or future additions. Conveniently located close to public transportation, shopping, dining, and everyday amenities, this home offers both space and accessibility. A great opportunity for homeowners or investors alike.

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

Listing Agent: Harold Baker (863-604-6272)

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)

Remarks: Seller offering $10,000 toward buyer closing costs or interest rate buy-down with full price offer. Welcome to 1985 Sarah Street, a 2025-built home in Winter Haven that perfectly blends modern design, functional space, and move-in-ready convenience. Situated on a premium corner lot with a fully fenced backyard, this 4-bedroom, 2.5-bathroom home offers 1,874 square feet of thoughtfully designed living space—ideal for both everyday living and entertaining. Step inside and immediately feel the difference. The entire first floor is designed for connection, featuring a bright, open-concept layout where the kitchen, dining, and living areas flow seamlessly together. The kitchen is bright and spacious—complete with upgraded stone countertops, modern finishes, and a clean, fresh look that feels straight out of a model home. Tile flooring throughout the main level adds both style and durability. Upstairs, the home continues to impress. A cozy loft space creates the perfect flex area—ideal for a second living room, home office, media space or home gym. The spacious bedrooms deliver comfort for everyone, while the owner’s suite provides a true retreat with a walk-in closet and an upgraded modern shower door in the primary bathroom. Step outside and you’ll find one of this home’s standout features—a large, fully fenced backyard, offering privacy, space to play, entertain, or simply unwind. The corner lot positioning adds extra breathing room and curb appeal that’s hard to find. Located in the desirable Peace Creek Reserve community, you’ll enjoy the benefits of newer construction living in a growing area known for its natural beauty and proximity to Winter Haven’s famous Chain of Lakes, shopping, and dining. Why wait for new construction when you can have better than new—right now? This home is upgraded and move-in-ready immediately.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Tyler Wampler (863-577-1234)

Remarks: Short Sale. APPROVED SHORT SALE AT PRICE! CHAPTER 7 BANKRUPTCY - Located In The Country Walk Community, This 2019 Built Home At 3180 Country Club Cir, Winter Haven, FL 33881 Features The Popular DR Horton Aria Floor Plan Offering 3 Bedrooms, 2 Bathrooms, & 1,672 Sq Ft Of Living Space. This Home Offers an Open Concept Layout With A Spacious Living Area, Split Bedroom Floor Plan, & a Functional Kitchen Overlooking The Main Living Space. Fenced Yard. Ideal For Everyday Living And Entertaining. Built In 2019, Conveniently Located Near Shopping, Dining, Schools, And Major Roadways With Easy Access Throughout Winter Haven. Bankruptcy Short Sale — Third-Party Approval Required. Property Sold As-Is. Great Opportunity For Owner-Occupants Or Investors Seeking Value In A Growing Area. Call Today For Details Or To Schedule A Private Showing.

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

Listing Agent: Jon Mccall, Pa (352-725-7206)

Remarks: One or more photo(s) has been virtually staged. Welcome to 718 Eagle Landing Blvd, where privacy, peaceful views, and modern living come together beautifully. Built in 2023 and sitting on one of the most desirable lots in the community, this home offers something that’s becoming harder and harder to find, open green space behind your home instead of another row of back windows. No rear neighbors. No cramped feeling. Just peaceful views and room to breathe. Recently refreshed with fresh interior paint, pressure washing, updated landscaping, and new mulch, this home is completely move-in ready and shows beautifully from the moment you arrive. Inside, natural light pours throughout the open-concept layout, creating a space that feels bright, welcoming, and comfortable all day long. The design is modern without feeling cold, offering the perfect balance of style and everyday livability. The spacious primary suite serves as a relaxing retreat with dual closets and a large walk-in shower, while the additional bedrooms offer flexibility for family, guests, a home office, playroom, or hobby space. But what truly makes this home special is the backyard potential. Whether you dream of adding a pool, building the ultimate outdoor entertaining space, creating a peaceful garden retreat, or simply enjoying wide open views without staring directly into another home, this property gives you the space and flexibility to make it happen. Rear fencing is permitted, giving future owners even more possibilities. Located in a growing area near shopping, dining, the Chain of Lakes, LEGOLAND Florida Resort, and the future SEA LIFE Florida Aquarium, this is a home positioned in an area that continues to grow in popularity and convenience. Homes with this combination of privacy, newer construction, natural light, and backyard potential rarely come available at this price point. Schedule your private showing today before someone else grabs one of the best lots in the community.

Listing is courtesy of: M2M REALTY (407-401-2275)

Listing Agent: Micaela Navarra (407-761-5501)

Remarks: This updated 3-bedroom, 2-bath home offers comfort, functionality, and plenty of outdoor space to enjoy Florida living. Inside, you’ll love the spacious open floor plan featuring a Great Room, dining area, and family room combination with cathedral ceilings, wood burning fireplace, laminate wood flooring, and abundant recessed lighting. French doors from the dining room lead to an open patio and a large backyard—ideal for entertaining or relaxing outdoors. This home is light and bright and move-in ready just for you! The kitchen features white raised-panel PVC cabinetry, black tile countertops, a closet pantry, and updated appliances including a refrigerator (2026) and stove (2022). Major system upgrades include a new 3.5-ton A/C system with new ductwork and a roof replaced in 2022. The split-bedroom layout offers privacy, with both bathrooms very nicely updated. The spacious primary suite includes a beautiful bath with stone floors, a quartz vanity with integral sink and wall-mounted faucet, and a walk-in shower with new tile, glass doors, and drain pan—part of a $15,000 renovation. Additional highlights include a garage with mini-split A/C, insulated garage door, pull-down ladder for attic access, washer/dryer hookup, and laundry sink. Outside you will have a 10’x12’ shed with electric, and a well house with a Culligan water softener system. A new black aluminum fence surrounds the property, with vinyl PVC privacy fencing along the left side, 12-foot gates on both sides plus a 6-foot front gate—perfect for storing a boat, RV, or extra vehicles. A covered rear carport adds even more flexibility. Conveniently located on a large corner lot near lakes, parks, recreation areas, LEGOLAND, Hwy 27 & I-4, and all that Central Florida has to offer. Welcome home!

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

Listing Agent: Russ Rhoads (863-604-1570)

Remarks: PRICE TO SELL!!!UP TO $5,000 IN BUYER INCENTIVES AVAILABLE! This property may qualify for up to $5,000 in closing cost credit when using the seller's preferred lender. Ask us how to qualify! Welcome to Sanctuary by the Lake — one of Winter Haven's most sought-after gated lakefront communities, built by Southern Homes along the stunning shores of Lake Rochelle, part of Florida's renowned Chain of Lakes. Whether you're looking for your forever home or a high-demand investment property, this one checks every box. This move-in ready, beautifully upgraded 3-bedroom, 2-bathroom home seamlessly blends modern design with relaxed lakeside living. Step inside to a spacious foyer that opens into a bright, open-concept living and dining area filled with natural light. Glass sliding doors lead to a generous, fully fenced backyard with room to add a pool — perfect for families and a future value-add for investors. The show-stopping kitchen is designed to impress, featuring stainless steel appliances, a mosaic tile backsplash, white shaker cabinets, a large center island with sink, and a full pantry. Designer touches throughout — bold accent walls, custom pendant lighting, and wood-look tile flooring — give this home a distinctive, upscale feel that stands out in any market. The primary suite is a true retreat with a walk-in closet and a spa-inspired en-suite bath complete with a soaking tub, walk-in glass shower, dual-sink vanity, and elegant tile finishes. Two additional bedrooms offer flexibility for family, guests, or a home office. A stylishly updated second bath rounds out the interior. Outside, enjoy a covered patio and lush backyard — your own private piece of Florida paradise. The 2-car garage adds convenience and storage. Community amenities include exclusive access to Lake Rochelle for kayaking and water sports, scenic walking trails, private docks, and a playground — all with low HOA fees and absolutely NO CDD. Ideally located near US-27, major shopping, dining, medical centers, and Central Florida's top destinations including LEGOLAND®, Walt Disney World®, and Universal Studios®. This is a limited opportunity — priced to sell and incentives won't last long. Call today to schedule your private showing!

Listing is courtesy of: REMAX PREMIER PROPERTIES (407-343-4245)

Listing Agent: Julio Salgado (407-791-0265)

Remarks: PRICE REDUCTION! Spacious 2,336 SF pool home in the gated, tranquil Overlook Estates. This 4BR/2BA floorplan features a split-bedroom layout and generous living space including an eat-in kitchen, 17x18 vaulted family room, 10x16 dining room with bay window, and a large foyer. The master suite includes a dressing alcove and walk-in closet; an adjacent bedroom makes an ideal office or nursery. High-traffic areas feature tile flooring; sliding glass doors in three rooms recess into the wall and open to a 31x50 pool deck — perfect for indoor/outdoor living. Additional highlights: 95x130 lot, terraced front walkway, 7x8 laundry with cabinetry and utility sink, 22x23 garage with built-in storage, tankless water heater, and leaf filter gutter guards. Ready for your finishing touches!

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

Listing Agent: Amy Reynolds (863-412-2279)

Remarks: NEW ROOF OCTOBER 2025!!! NEW HVAC 2025!!! PLUS...SELLERS ARE OFFERING SIX MONTHS FREE HOA DUES TO BE PAID FOR BUYER. Won't find these newbies on very many homes. Fully furnished 2 bedroom/2 bath home in Orange Manor West. Enjoy your mornings/evenings on your spacious, enclosed lanai. Located in Southeast Winter Haven this park offers easy access to a variety of local restaurants, grocery stores and attractions. This fully furnished home comes with one share of Orange Manor West Co-Op. Monthly fees include cable, internet and trash pick up. Residents enjoy community pool, clubhouse, horseshoes billiards, mini gold, shuffleboard, fishing, bingo, arts and crafts and MORE. Another great feature is recently installed HVAC. NO PETS, ONLY EMOTIONAL AND SERVICE DOGS

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

Listing Agent: Darlene Bice (863-557-6439)

Remarks: Under contract-accepting backup offers. Beautifully maintained 4-bedroom, 2-bathroom home with a 2-car garage, situated on a spacious corner lot of over a quarter acre in desirable Winter Haven. The primary suite features an en suite bathroom with a walk-in shower, while three additional generously sized bedrooms and a second full bath provide comfortable accommodations for family or guests. The inviting kitchen offers ample space with a breakfast bar and adjacent dining area, perfect for everyday living and entertaining. An inside laundry room adds convenience. Enjoy outdoor living in the fully fenced backyard, complete with plenty of room to relax, play, or entertain, and a perfectly sized patio for gatherings. Ideally located close to shopping, dining, entertainment, medical facilities, and the world-famous Plant City Strawberry Festival

Listing is courtesy of: JT REALTY & ASSOCIATES (352-279-2640)

Listing Agent: Lindsey Funderburk (352-606-9639)

Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully fully remodeled home, where modern design meets everyday comfort. Featuring a brand-new roof, this property offers peace of mind and long-term value from the moment you arrive. Step inside to discover stunning modern bathrooms thoughtfully updated with sleek finishes and contemporary style. The heart of the home is the open-concept kitchen, designed to impress with elegant wood cabinetry, convenient soft-close features, luxurious quartz countertops, and a full suite of stainless steel appliances—perfect for both daily living and entertaining. With its seamless layout and high-quality upgrades throughout, this move-in-ready home is ideal for buyers seeking style, functionality, and worry-free living.

Listing is courtesy of: FUTURE HOME REALTY INC (800-921-1330)

Listing Agent: Constantin Florean (407-953-7810)

Remarks: New Price! Move-in ready Central Florida home featuring an open-concept floor plan, high ceilings, and fresh interior paint. Recent upgrades include luxury vinyl plank flooring throughout the main living areas and durable vinyl flooring in all bedrooms—no carpet. The modern kitchen offers quartz countertops, espresso cabinets with crown molding, a center island, and Samsung stainless steel appliances. The spacious primary suite includes dual vanities, a walk-in closet, and a private en-suite bath. Additional features include a whole-home water softener and filtration system, custom blinds, ceiling fans, washer and dryer, programmable thermostat, and Ring doorbell system. Enjoy a fully fenced backyard with updated landscaping and irrigation, plus a covered patio for outdoor living. Built with energy-efficient windows and insulation, this home also offers a two-car garage, architectural shingles, and access to community amenities including a pool and playground. Conveniently located and ready for its next owner—schedule your private showing today.

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

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

Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. New construction home with 2005 square feet on one-story including 3 bedrooms plus a den, 2 baths, and an open living area. Enjoy an open kitchen with Silestone 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, a tiled shower, and a closeted toilet. 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 showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey!

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

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

Remarks: Under contract-accepting backup offers. Welcome to 22 Lake Link in Winter Haven, where space, lifestyle, and location come together in one exceptional opportunity. Situated on a large corner lot, this 4-bedroom, 2-bathroom home with a 2-car garage offers the perfect combination of comfort, functionality, and Florida living. Step inside to a bright and open floor plan designed for modern living and entertaining. The spacious layout flows seamlessly from the living and dining areas to the kitchen, creating the perfect environment for hosting family and friends. Enjoy your mornings on the front balcony and unwind in the evenings on the screened-in patio, overlooking your huge fenced-in backyard—ideal for pets, gatherings, or even adding a pool. Additional highlights include a durable metal roof for long-term value and a large driveway with plenty of space for multiple vehicles, guests, or recreational toys. This home is perfectly positioned to give you access to everything that makes Central Florida one of the most desirable places to live. Convenient access to major highways including Interstate 4, US Route 27, and Florida State Road 540 for easy commuting to Orlando, Tampa, and beyond. Just a short drive to world-famous attractions like Walt Disney World, Universal Orlando Resort, and LEGOLAND Florida Resort. Enjoy weekend trips to Florida’s beautiful beaches including Clearwater & St. Pete Beach (west coast) and Cocoa Beach (east coast). Living in Winter Haven means you’re close to a growing scene of local favorites and everyday conveniences such as, Coffee spots like Richard's Fine Coffees and Starbucks. Popular dining options including Harborside, Tanners Lakeside Restaurant & Bar, Aria and Azteca D'Oro. Shopping and entertainment nearby at Winter Haven Central Park and Eagle Ridge Mall. Minutes from Lake Link and the Chain of Lakes of Winter Haven, Florida.

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

Listing Agent: Omar Andreasen (407-883-2989)

Remarks: Welcome home to this newer 3-bedroom, 2-bath residence built in 2020, offering 1,672 square feet of thoughtfully designed living space. The open-concept layout creates a bright and inviting atmosphere, with the living, dining, and kitchen areas flowing together to accommodate both everyday living and entertaining. The primary suite features a walk-in closet, while the primary bathroom is equipped with dual sinks and a walk-in shower for added convenience. With a functional floor plan and modern design, this home provides the ideal blend of comfort and practicality. The home is ready to be converted into your ideal living space. Don't miss your opportunity to make this home yours—schedule your private showing today! The home is being sold in as is condition. All buyers must view the home before submitting an offer.

Listing is courtesy of: REALTYCITY INC (863-438-6605)

Listing Agent: Jesse Carriedo (863-438-6605)