Homes For Sale in Winter Haven 33880 - 235 homes

Remarks: Under contract-accepting backup offers. 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: Short Sale. **SHORT SALE** BANK APPROVED PRICE** CAN CLOSE QUICKLY*** Welcome to this beautiful 3-bedroom, 2-bathroom block home perfectly positioned at the end of a quiet cul-de-sac in Winter Haven's sought-after Cypress Gardens neighborhood. With 1,400 square feet of interior living space and a layout designed for both comfort and connection, this home checks every box. Step inside and you're immediately greeted by a bright, open floor plan where the living room, dining area, and kitchen flow together seamlessly ideal for everyday living and effortless entertaining. The kitchen is generously sized, featuring an abundance of cabinetry and two lazy Susan's that maximize every inch of storage. Natural light floods the home through an impressive array of windows, and sliding glass doors in the main bedroom, middle bedroom, and living room all open directly onto the crown jewel of this property: a stunning 47 x 15 screened-in patio complete with a bar area, built-in grill, refrigerator, and cabinetry. Whether you're hosting guests or simply enjoying a quiet Florida evening, this outdoor space delivers. Both bathrooms have been tastefully updated. The guest bath features a brand-new tub and shower installed by Westshore Homes in October 2025, along with a new vanity, mirrored medicine cabinet, cabinet above the toilet, and new toilet. The main bathroom has also been refreshed with a new mirrored medicine cabinet, cabinet above the toilet, and new toilet. Major systems are all squared away brand-new roof in 2025, A/C replaced in 2021, and water heater from 2018 offering true peace of mind from day one. The home is also pre-wired for a generator, a smart bonus for Central Florida living. The attached garage includes a dedicated laundry and storage room with extensive shelving, and the washer and dryer convey with the home. Set on an 8,537 square foot lot at the end of a tucked-away cul-de-sac, this property offers the rare combination of privacy, space, and convenience. Just minutes from US-27, LEGOLAND Florida Resort, Winter Haven Hospital, Polk State College, and the renowned Chain of Lakes, everything Central Florida has to offer is right at your doorstep. Homes this move-in ready, this well-maintained, and this well-located don't stay on the market long schedule your private showing today!

Listing is courtesy of: NEW HEIGHTS REALTY GROUP (407-934-0305)

Listing Agent: Daniel Rodriguez (407-934-0305)

Remarks: Saltwater pool. Boat parking. Private community boat ramp. Welcome to 315 Lanceolate Drive, a beautifully updated 4-bedroom, 2-bath home located in the gated community of The Village at Spirit Lake. Inside, you'll find a completely renovated kitchen and beautifully remodeled bathrooms, creating a fresh, modern feel while maintaining a comfortable and functional layout. Step outside to your own private retreat featuring a sparkling saltwater pool, screened lanai, and a fully fenced backyard—perfect for relaxing, entertaining, or enjoying Florida's year-round sunshine. The second bathroom provides direct access to the pool area, adding convenience for family and guests. Need extra space? The garage has been converted into two air-conditioned bonus rooms, offering incredible flexibility for a home office, gym, hobby room, playroom, or additional storage to fit your needs. The extended driveway provides the perfect place to park your boat, and residents of The Village at Spirit Lake enjoy exclusive access to a private community boat ramp on Spirit Lake. The neighborhood also features a brand-new playground, pickleball courts, a basketball court, clubhouse, gated entrance, and a very reasonable HOA. Ideally located just minutes from the Polk Parkway, commuting to Lakeland, Tampa, or Orlando is a breeze. The home is also located in unincorporated Polk County, allowing you to enjoy the benefit of county taxes only. Conveniently close to shopping, dining, schools, and Legoland Florida Resort, this move-in-ready home offers the perfect blend of updated finishes, flexible living space, and the Florida lifestyle you've been looking for. Schedule your private showing today and discover everything this exceptional home has to offer.

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

Listing Agent: Veronica Bard (863-670-7526)

Remarks: Virtually Staged. Welcome to this updated 4-bedroom, 2-bath home offering 1,750 square feet of bright, open living space in the desirable Queens Cove community of Winter Haven. Step inside to discover vaulted ceilings, abundant natural light, and an open-concept floor plan designed for comfortable everyday living and effortless entertaining. Luxury vinyl plank flooring flows throughout the house, while the spacious kitchen features granite countertops, white cabinetry, stainless steel appliances, extensive counter space, a breakfast bar, and a seamless connection to the living and dining areas. The split-bedroom layout provides added privacy, with a generous primary suite offering a walk-in closet and an en-suite bath. Three additional bedrooms provide flexibility for family, guests, or a home office. Sliding glass doors lead to the backyard with plenty of space to create your own outdoor oasis, add a pool, or simply enjoy Florida living. Additional highlights include a two-car garage, an inside laundry area, and a roof replaced in 2018 and new HVAC in 2022. Conveniently located just minutes from Legoland Florida Resort, shopping, restaurants, schools, medical facilities, and major roadways including the Polk Parkway and US-27, this home offers easy access to both Tampa and Orlando while enjoying the charm of Winter Haven's renowned Chain of Lakes. Whether you're searching for your primary residence, a second home, or an investment property, this move-in-ready home offers exceptional value in a convenient Central Florida location.

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

Listing Agent: Cindy Greco (813-240-8300)

Remarks: Discover the perfect blend of style, comfort, and peace of mind in this beautifully updated 3-bedroom, 2-bath home that’s ready for you to move right in. Thoughtfully refreshed with fresh interior and exterior paint, this home offers a bright, welcoming atmosphere from the moment you arrive. The heart of the home is the stunning kitchen, featuring gorgeous granite countertops, sleek stainless steel appliances, and ample cabinet and counter space—perfect for preparing family meals, entertaining guests, or enjoying your morning coffee. The open and functional layout creates a warm, inviting flow that’s ideal for both everyday living and special gatherings. Enjoy the confidence that comes with major recent upgrades, including a brand-new roof and new energy-efficient A/C system, providing comfort and peace of mind for years to come. Retreat to the spacious primary suite, while two additional bedrooms allows for flexibility for family, guests, a home office, or hobby space. Every room has been thoughtfully refreshed, making this home truly move-in ready. Step outside and fall in love with the oversized backyard—just under a quarter acre—offering endless possibilities. Whether you envision weekend barbecues, kids play area, a flourishing garden, or simply relaxing under the Florida sunshine, this outdoor space is ready to bring your vision to life. The bonus storage shed provides valuable extra space for lawn equipment, tools, seasonal décor, or even your favorite DIY projects. Conveniently located near shopping, restaurants, schools, parks, and major roadways, this home combines everyday convenience with the charm of a quiet neighborhood. Whether you’re a first-time homebuyer, growing family, downsizing, or searching for a fantastic investment opportunity, this exceptional property checks all the boxes. Don’t miss your chance to own this beautifully updated Winter Haven gem. Schedule your private showing today and experience everything 362 Holly Ridge Road has for you!

Listing is courtesy of: MILLSHIRE REALTY (863-815-8000)

Listing Agent: Katrina Asher (863-934-0575)

Remarks: Excellent investment opportunity with leaseback in place. This featured Everglades model home by Laref Homes is being offered with a 2-year leaseback through April 30, 2028, at $2,570/month, providing immediate rental income. There is an effortless style to this stunning 2,032 sq. ft. home, featuring three bedrooms plus a versatile den and an open-concept layout. Premium vinyl flooring flows seamlessly throughout, leading to a beautifully designed kitchen with a striking waterfall island. The spacious living area connects naturally to a covered lanai, creating a bright and modern living environment. Loaded with upgrades, this model home offers a unique combination of design and functionality. Furniture not included.

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

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

Remarks: New - New - New! This 3 bedroom 2 bath features a beautiful lake view and has been completely remodeled. Updates include a new HVAC system, new metal roof, new kitchen with granite counters, new bathrooms, new flooring, and new septic system. No HOA means you can store your boat.

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Dwight Head (863-965-0207)

Remarks: Welcome to your dream home, a charming 2-bedroom, 2-bath retreat with a versatile bonus room that can be used as a 3rd bedroom or a separate home office featuring its own private exterior entrance! This inviting home has been thoughtfully refreshed and is move-in ready, offering fresh interior paint, a new smart thermostat, recent tree removal, and a brand-new shingle roof (03/24) for peace of mind! Inside, you’ll find a spacious kitchen with a breakfast bar that opens to a bright living room, ideal for everyday living and entertaining. The large dining room or secondary family room is conveniently located next to the kitchen and provides plenty of space for gatherings. Relax in the cozy Florida room, featuring warm wood walls and ceilings and an abundance of windows where you can enjoy views of Lake Elbert! Outside you will find your large paver patio, perfect for entertaining or unwinding, and enjoy the privacy of a newly built fully fenced backyard. Additional updates include a new AC (2022), blown attic insulation (2022), water heater (2019), all kitchen appliances (2021), and Exterior Front Porch paint along with a new front door (2025). Conveniently located just minutes from Downtown Winter Haven, Polk State College, HWY 27, and medical facilities, this home blends comfort, flexibility, and an excellent location. Schedule your showing today!

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

Listing Agent: Jenna Henderson (850-524-3843)

Remarks: Under contract-accepting backup offers. Welcome to your own private backyard retreat in the heart of Winter Haven! This beautifully maintained 3-bedroom, 2-bath pool home sits on a spacious .31-acre lot with NO HOA and offers the perfect blend of comfort, convenience, and Florida living. The true showstopper is the incredible approximately *983-square-foot covered lanai*, creating an expansive outdoor living space rarely found in homes of this size. Perfect for entertaining, relaxing, outdoor dining, or even a home gym, this massive covered retreat overlooks the sports-style pool, oversized fenced backyard, custom playground, firepit, raised irrigated garden beds, and turf-and-tile entertaining area. Best of all, enjoy spectacular *LEGOLAND fireworks* views right from your own backyard. Inside, you'll find a bright and inviting floor plan with generous living spaces, comfortable bedrooms, and a well-appointed kitchen that flows seamlessly into the living and dining areas. Recent updates provide peace of mind, including a New Roof (2023), New Covered Lanai (2023), whole-home re-plumbing (2024), reverse osmosis system in the kitchen (2024), stainless steel dishwasher (2021), gas water heater (2021), irrigation system for yard (2023), updated light fixtures throughout, Ring security system with automatic flood lights, and added recessed lighting in the living room and kitchen. The outdoor space was thoughtfully enhanced in 2024 with stained fencing, rocked and irrigated landscape borders, a fully sealed playground, and beautifully designed gathering spaces that make this property ideal for everyday living and entertaining alike. Conveniently located just minutes from Downtown Winter Haven, LEGOLAND Florida Resort, major hospitals, shopping, dining, and everyday conveniences, this move-in-ready home offers the perfect combination of location, lifestyle, and value. Don't miss this rare opportunity to own a beautifully updated pool home with an extraordinary outdoor living experience. Schedule your private showing today!

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

Listing Agent: Jenna Henderson (850-524-3843)

Remarks: Under Construction. Under construction. This new construction build sits on almost an acre (.72) and is a comfortable and cozy home with 3 bedrooms, 2 bathrooms and 1,467 square feet of living space. The foyer opens to the spacious dining and great rooms, with raised ceilings throughout the home, and there's convenient access to the outdoor patio from the living space. The kitchen features a large island. The primary bathroom boasts a separate shower and tub, and this home comes equipped with ample storage space including two oversized primary walk-in closets, a pantry in the kitchen, a linen closet and a coat closet. The spacious (413 sq ft) 2-car garage provides additional storage and laundry space. This home is located in a quiet neighborhood off Winter Lake Rd, close to all of the amenities Lakeland or Winter Haven have to offer! With no HOA, there's room for your boat, RV, or other outdoor vehicles. USDA FINANCING AVAILABLE FOR ELIGIBLE BUYERS, WITH NO MONEY DOWN. CALL TODAY FOR MORE DETAILS.

Listing is courtesy of: PORCHLIGHT HOMES LLC (863-529-3369)

Listing Agent: Angie Reynolds (863-838-1090)

Remarks: This charming 4-bedroom, 2-bathroom new construction build features an open floor plan and 1,778 square feet of living space, all while sitting on a .73 acre lot. The spacious great room, with high vaulted ceilings is perfect for family movie nights in, with convenient access to the back patio. The large open kitchen caters to family living as well as entertaining with its lengthy seated bar for that delicious morning breakfast, and is located perfectly in between the great room and dining area. The ample primary bedroom is enhanced by its dual-sink vanity bathroom and walk-in closet featuring a linen closet within. Additionally, the spacious garage provides additional storage and leads directly into the home’s designated laundry space. This home is located in a quiet neighborhood off Winter Lake Rd, close to all of the amenities Lakeland or Winter Haven have to offer! With no HOA, there's room for your boat, RV, or other outdoor vehicles. USDA FINANCING AVAILABLE FOR ELIGIBLE BUYERS, WITH NO MONEY DOWN. CALL TODAY FOR MORE DETAILS.

Listing is courtesy of: PORCHLIGHT HOMES LLC (863-529-3369)

Listing Agent: Angie Reynolds (863-838-1090)

Remarks: Picture yourself in this top-floor, 3-bedroom, 2-bathroom condo with a Sun/Florida room, nestled in the desirable Imperial Harbor community of Winter Haven. With easy access via an elevator, this is the peaceful 55+ retreat you’ve been searching for!Imagine waking up and enjoying a morning stroll to the private community dock on Lake Howard, where you can cast a fishing line or set off on a boat ride—and yes, boat docking is INCLUDED in your HOA dues! Spend your afternoons soaking in the heated pool, staying active in the fitness center, or playing a friendly round of shuffleboard or billiards. This is truly resort-style living at its finest. Centrally located only about 45 minutes to Tampa or Orlando.Step inside to discover a bright, open layout with a spacious kitchen, perfect for entertaining. The primary suite boasts a walk-in closet, while the additional bedrooms provide plenty of space for guests, hobbies, or a home office. Plus, the in-unit laundry closet comes equipped with a washer and dryer for ultimate convenience.Best of all, your water, basic cable, and internet are included, making for effortless, low-maintenance living. This is the dream lifestyle you deserve—schedule your private tour today and make it yours!

Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)

Listing Agent: Justin Cans (347-238-0790)

Remarks: Don't miss this move-in ready, recently updated 3 bedroom, 2 bathroom block home with a 2-car garage, situated on a spacious 7,370 sq ft lot in Winter Haven. This 1994 built home features a recently remodeled kitchen with quartz countertops, shaker cabinets, stainless steel appliances, luxury vinyl plank flooring, updated bathrooms, and fresh paint throughout! Major components like the roof and A/C have both been updated in recent years, with plenty of life remaining for added peace of mind. The open living room features a shiplapped fire place. Out back, enjoy the newly installed paver patio, perfect for grilling, relaxing, or entertaining in the spacious yard. This is a great value for a well-updated home with both indoor and outdoor space at an affordable price point with a low HOA! FHA and VA friendly! *Some photos have been virtually staged*

Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)

Listing Agent: Philip Bach, Pa (786-351-2294)

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: Under contract-accepting backup offers. This expansive property is a true diamond in the rough, perfectly positioned for the savvy investor looking for a great return on a "buy and hold" scenario or a strategic value-add project. Boasting a generous 0.41-acre lot, this property is designed for versatility. With a massive layout featuring 6 bedrooms and 4 bathrooms, the home offers the unique potential for 3 or even 4 separate doors (units), making it an ideal candidate for a multi-generational living setup or a high-performing rental portfolio addition. Only 12 minutes away from LEGOLAND!

Listing is courtesy of: MARZUCCO REAL ESTATE (813-679-1365)

Listing Agent: Clarisa Moody (813-446-2003)

Remarks: Short Sale. Investor opportunity in Winter Haven. Welcome to this 3 bedroom, 2 bath home offering an open and inviting layout with vaulted ceilings and a spacious family room designed for comfortable everyday living. Tile flooring flows seamlessly through the main living areas and into the galley kitchen, creating a bright and cohesive feel throughout the home. Built with durable block construction, this property also features a single car garage. Step outside to enjoy a beautifully shaded lot, perfect for relaxing or entertaining guests in a private outdoor setting. This is a Short Sale. Professionally processed by ARII SOLUTIONS, LLC. Buyer Responsible Short Sale Processing Fee of $5,000. Please review ''Presentation of Offers'' document before submitting offer. Property sold as-is

Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)

Listing Agent: Robert Arnold, Jr (407-389-7318)

Remarks: Amazing potential. This 2-bedroom, 2-bathroom townhouse features a spacious 1,252 square foot floor plan and is located in the established Stonebridge community.

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

Listing Agent: Sarah Armstrong (863-287-0252)

Remarks: NO HOA. NO CDD. IN GROUND POOL. NEW HVAC. NEW ROOF. Welcome to 2230 W Central Ave, where timeless character meets modern updates on an oversized double lot in the heart of Winter Haven. This well-maintained 3-bedroom, 2-bath home offers comfortable living with inviting spaces designed for everyday life and entertaining. Step inside to a welcoming parlor that flows into the dining room, creating a warm and functional layout. The kitchen features a picturesque window overlooking the backyard and includes Samsung stainless steel appliances. Just off the kitchen, the spacious family room provides a cozy retreat with direct access to the LARGE screened porch. The backyard is the true centerpiece of this property. Enjoy Florida living year-round with a large screened enclosure surrounding the sparkling in-ground pool, offering plenty of space for outdoor dining, relaxing, and entertaining family and friends. Recent improvements provide added value and peace of mind, including a NEW ROOF installed in November 2024, a NEW HVAC Carrier system installed in 2022, and an A.O. Smith water heater. Outdoor enthusiasts will appreciate the public boat ramp to Lake Howard just two blocks away, along with ample driveway parking for your boat, trailer, or additional vehicles. With its spacious lot, major updates, fantastic outdoor living space, and convenient location close to shopping, dining, parks, and the Chain of Lakes, this move-in-ready home is a wonderful opportunity. Come see this gem today!

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

Listing Agent: Andrea Baker (407-516-9697)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully remodeled 3-bedroom, 2-bathroom residence situated on a generous lot of nearly one-third of an acre. Offering an abundance of flexible living space, the interior features fresh neutral paint, brand-new porcelain tile flooring, and fully upgraded finishes throughout. The updated kitchen is equipped with granite countertops, stainless steel appliances, and brand-new cabinetry. A welcoming, oversized sunken living room offers an ideal space for relaxation, featuring French doors that open to a spacious enclosed Florida room overlooking the fenced backyard. The primary suite provides a private retreat, complete with an en-suite bathroom, a walk-in closet, and direct access to the Florida room. Additional functional spaces include a dedicated private office and a fully air-conditioned bonus room with a closet, professionally constructed inside the garage space. Outside, the large yard offers ample space for a pool, while the extra-wide driveway and double-gate side access accommodate boat or RV parking. Major mechanical updates include a roof replaced approximately 6 years ago and a new water heater installed in 2024. Located with quick access to major roadways and featuring no HOA fees, this solid, well-maintained home offers exceptional functionality and everyday convenience.

Listing is courtesy of: HOUWZER INC (267-765-2080)

Listing Agent: Daniel Robinson (904-447-8922)

Remarks: Welcome to this charming and versatile 4-bedroom, 2.5-bath home nestled on a quiet cul-de-sac in sought-after Southeast Winter Haven, offering the perfect combination of comfort, functionality, and thoughtful updates. Inside, you'll find a flexible floor plan featuring TWO SPACIOUS LIVING AREAS plus an additional FLEX SPACE that can easily serve as a home office, playroom, fitness room, or media room to fit your lifestyle. The kitchen, remodeled in 2004, offers abundant wood cabinetry and generous counter space while flowing seamlessly into the dining area, making everyday living and entertaining a breeze. The spacious primary suite features its own ensuite bathroom, providing a private retreat, while the additional bedrooms offer flexibility for family, guests, or a home office. Carpet flooring adds warmth and comfort in all bedrooms. Enjoy even more living space in the large screened-in patio overlooking the backyard, complete with a detached storage shed that's ideal for extra storage, hobbies, or lawn equipment. Recent updates provide added peace of mind, including a 2020 ROOF, approximately 2020 A/C system and air handler installed by Tradition Air, NEW PLUMBING (2026), and an electrical panel updated within the last 10 years. The home is connected to city water and city sewer, with electric service provided by TECO. Vacant and ready for its next owner, this property presents an excellent opportunity for a primary residence, seasonal home, or investment. Conveniently located just minutes from downtown Winter Haven, you'll enjoy easy access to shopping, dining, medical facilities, parks, and the city's renowned Chain of Lakes. Commuters will appreciate the proximity to US-17, Cypress Gardens Boulevard, and the Polk Parkway, while nearby attractions, including LEGOLAND® Florida Resort, add to the area's appeal. The peaceful cul-de-sac setting combined with its desirable Southeast Winter Haven location offers the perfect balance of privacy, convenience, and the Florida lifestyle.

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

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