Homes For Sale in Winter Haven 33881 - 280 homes

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

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

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

Remarks: Big Price Drops and Price to sell. Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. This property features a newer roof put on in 2023, a newer in-ground pool put in 2022, and a large backyard shed, offering the perfect blend of comfort, storage, and outdoor enjoyment. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.

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

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

Remarks: Welcome to this spacious and recently upgraded home sitting on a rare 0.40-acre corner lot with NO HOA and NO CDD, giving you the freedom and space you’ve been looking for. Major recent improvements include updated HVAC, electrical, and plumbing systems for added peace of mind, along with attractive interior upgrades featuring modern flooring, an updated kitchen with stylish cabinetry and stainless-steel appliances, and refreshed bathrooms with contemporary tile finishes. The oversized lot offers endless possibilities and plenty of room to park your RV, boat, jet ski, work vehicles, or recreational toys worry-free — something hard to find in today’s market. Conveniently located near major supermarkets, restaurants, schools, and main roads for easy commuting, this property is ideal for homeowners seeking space and flexibility or investors looking for a strong opportunity. Schedule your private showing today and discover the value, freedom, and potential this unique property has to offer!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Jose Hooker-Gomez (407-272-6986)

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

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

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

Remarks: One or more photo(s) has been virtually staged. Welcome to 265 Meadowbrook Blvd, Winter Haven, FL 33881—this well-maintained 3-bedroom, 2-bathroom residence features a comfortable and functional layout designed for everyday living and entertaining. The home features an open-concept floor plan with generous living and dining areas filled with natural light, creating an inviting atmosphere throughout. The kitchen provides ample cabinetry and counter space, along with modern appliances, making it both practical and efficient. The primary bedroom includes a private en-suite bathroom and a walk-in closet, while the additional bedrooms provide versatility for guests, a home office, or other needs. Step outside to a spacious backyard with plenty of room for outdoor activities, gardening, or relaxation. Conveniently located with easy access to major roadways, this property is just minutes from shopping and dining options at Posner Park and Eagle Ridge Mall, as well as outdoor recreation at Lake Shipp Park. Enjoy proximity to popular attractions like LEGOLAND Florida Resort and convenient travel via Orlando International Airport. This property presents a great opportunity to own a move-in ready home in a centrally located area close to everyday conveniences, entertainment, and recreation.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Michael Cruz Irizarry (407-530-7620)

Remarks: Fully Remodeled 3 Bed / 3 Bath with No HOA – Move-In Ready in Winter Haven! Welcome to 3420 Avenue T NW — a completely updated 3-bedroom, 3-bathroom home featuring a rare full-bath-for-every-bedroom layout, all-new appliances, and a brand-new 6-foot privacy fence. This home has been renovated with today’s buyer in mind, offering a clean, modern interior with updated flooring, a refreshed kitchen, and a seamless open-concept living space. The kitchen is equipped with brand-new stainless steel appliances and flows easily into the main living areas, making it perfect for both daily living and entertaining. Each bedroom offers direct access to a full bathroom, providing flexibility for families, guests, or multi-use living arrangements — a feature that sets this home apart from typical properties in this range. The fully fenced backyard adds another layer of value, giving you private outdoor space ready for pets, play, or relaxation. If you’re searching for a move-in-ready home with modern updates, functional layout, and strong value, this one checks the boxes.

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

Listing Agent: Don Jerue (863-259-9550)

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

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

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

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

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

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

Remarks: Under Construction. New construction home with 2819 square feet 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 3 and 4 share a jack-and-Jill bathroom. Plus, enjoy a 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 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 Construction. New construction home with 1819 square feet on one-story including 4 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with, Quartz countertops Samsung stainless steel appliances, a walk-in pantry, and a spacious counter height 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/photos 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: Turnkey quadplex investment opportunity in Winter Haven with seller financing available, creating flexible acquisition options for investors seeking leverage and immediate entry into a performing asset. This income-producing multifamily property features 4 of 5 units currently leased, delivering strong in-place cash flow with additional upside from one vacant unit. Recent capital improvements include a new metal roof, updated HVAC system, and multiple interior and exterior upgrades completed within the past year, reducing near-term maintenance exposure and supporting long-term returns. The property offers practical unit layouts, established tenancy, and is positioned in a high-demand rental corridor near retail, dining, schools, and major transportation routes. Continued growth and redevelopment throughout Winter Haven reinforce rental demand and long-term appreciation potential. An efficient addition to any rental portfolio, suited for investors pursuing passive income, portfolio expansion, or a structured value-add play. Seller financing terms enhance flexibility and can improve overall income depending on structure. Contact for financials, rent roll, and seller financing details.

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

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

Remarks: Under Construction. Brand-new 3-bedroom 2-bath home! The Ashlyn features an inviting and open living area under an airy volume ceiling. Relax in your private owner's suite featuring a large en-suite bath with a decorative tiled shower with glass enclosure, dual vanities, a closeted toilet, and walk-in wardrobe .Two secondary bedrooms share a hall bath. Plus, enjoy outdoor living on your covered lanai! This home includes features and finishes hand-selected by our professional designers to provide you with enduring style, move-in convenience, and easy home maintenance: Beautifully designed kitchen with: Breakfast bar. Quartz countertops. 36-in. espresso birch wood cabinets with decorative knobs/pulls. Stainless steel undermount sink with a pull-down faucet. Convenient pantry. Samsung stainless steel appliances: 5-burner smooth-top electric range with wi-fi smart controls. Fingerprint-resistant microwave with ventilation system. ENERGY STAR(R) quiet-operation dishwasher. ENERGY STAR(R)side-by-side refrigerator. . . Low-maintenance luxury vinyl plank flooring throughout the living areas, kitchen, laundry room, and bathrooms. Mohawk stain-resistant carpet in the bedrooms. Energy-efficient LED lighting in the kitchen and gathering room. Custom-fit 2-in. faux wood window blinds. Built-in pest control. Architectural shingles with limited-lifetime warranty. Fully sodded homesite with Florida friendly landscaping and irrigation system. ... and much more!. Save on utilities with energy-efficient R-30 insulation, foam-injected block insulation, double-pane Low-E windows, and a programmable thermostat. For more information about this beautiful, professionally designed move-in ready home in Winter Haven, FL, call or email us today!

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

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

Remarks: MAJOR PRICE IMPROVEMENT! Experience relaxed Florida living in this furnished 2-bedroom, 1-bath manufactured home located in the gated 55+ community of Lakeside Ranch. The home features laminate flooring with carpeted bedrooms, central A/C, and a roof that is only 2 years old, offering added peace of mind for the next owner. Residents enjoy an impressive array of amenities, including a heated pool, library, shuffleboard, horseshoes, billiards, scheduled community activities, trailer storage, and on-site laundry facilities. This privately owned community is supported by a self-contained water and sewer system with backup generators and offers a low monthly HOA fee of $145, which includes water, sewer, and lawn mowing. Enjoy direct access to beautiful Lake Henry, an 810-acre private lake, complete with a boat ramp available for resident use—perfect for peaceful days on the water. Buyer approval by the HOA is required, along with a $40 non-refundable background check. An easy, low-maintenance lifestyle awaits,ideal for enjoying the best of Florida living. This home is financeable. y

Listing is courtesy of: EXIT REALTY 4CORNERS (863-344-3948)

Listing Agent: Carlos Dejesus (407-818-6868)

Remarks: Under contract-accepting backup offers. Short Sale. One of the most sought-after floor plans, this 4-bedroom, 2-bathroom home boasts numerous charming features and is set on an oversized lot with no rear neighbors and a serene water view. As you enter, you'll find three spacious bedrooms and a modern bathroom. To the left, the inviting, contemporary kitchen showcases a large pantry offering ample storage space. The open dining area flows seamlessly into the airy living room, creating a perfect space for gatherings. Step outside to your private screened-in patio and enjoy the expansive yard with a tranquil, picturesque view. The luxurious Master Suite features dual sinks and a generous walk-in closet. The kitchen island and open layout are perfect for entertaining. This home comes complete with all major appliances, blinds, and is equipped with Smart Home Technology, including Alexa. Conveniently located near I-4, shopping, and entertainment, and offering access to a community pool. All of this at an unbeatable price in an up-and-coming location!

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

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

Remarks: HUGE price reduction! Lakefront Living in Hamilton Point! Discover this spacious 5-bedroom, 3-bath home located in the upscale Hamilton Point community, within the city limits of Winter Haven. Situated on just under one acre, this rare lakefront property offers space, privacy, and the perfect setting for enjoying Florida’s outdoor lifestyle. Start your summer right with direct access to Lake Hamilton, a beautiful 2,142-acre lake known as one of Central Florida’s premier fishing destinations. Whether you enjoy waterskiing, jet skiing, fishing, or relaxing boat rides, this lake has something for everyone. Even better, this property offers true chain access to two additional lakes, expanding your boating adventures. Take a short ride across the water to two of the area’s favorite spots—Port 27 for waterfront dining or the local favorite Floridino's Italian Kitchen, known for serving some of the best pizza around. You might even spend an afternoon simply relaxing on the water while watching seaplanes land and take off. Surrounded by mature vegetation and located in a quiet, well-established community, this home truly has so much to offer. Properties like this are a rare find—especially on true lakefront acreage in such a desirable location.

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

Listing Agent: Lamanda Jones (863-557-3627)

Remarks: LAKEFRONT 3 BEDROOM / 2 BATH HOME WITH PICTURESQUE OPEN WATER VIEWS AND PRIVATE 30 FT DOCK! Located directly on Lake Pansy in the gated subdivision of Hartridge Hills, a quaint lakefront community of approximately 60 homes. NEWER ROOF 2022 and NEWER GENERAC GENERATOR 2020. Lot size is 150 X 83 ft directly on Lake Pansy. Additional lot size in records of 2.44 acres includes riparian or water rights into the lake. Beautiful stone working fireplace with vaulted ceiling in the great room. Spacious kitchen with plenty of storage and breakfast area overlooking tranquil water views. Home was originally constructed with 2,247 sq ft and later the expansive back porch was enclosed bringing the total to 2,958 sq ft of air-conditioned living space under roof. Large windows and sliding glass doors frame panoramic vistas, infusing the space with a sense of tranquility and connection to nature. Attached 2-car garage with large storage room. HOA fees include lawn care, trimming and fertilizer to give you more time to relax. Access to Lake Hartridge and the ‘Chain of Lakes’, a navigable canal system connecting 15 lakes, is obtained from the private community boat ramp and dock. This community is well known and desired by aircraft owners and flying enthusiasts as it is near Gilbert Field-Winter Haven Regional Airport, a city-owned airport that supports over 80,000 flights a year. It is also home to the Jack Brown Seaplane Base renowned as the largest and one of the oldest seaplane training and base operations in the world. Conveniently located between Orlando and Tampa with great attractions, waterfront restaurants, shopping, and some of the best fishing and ski lakes available! Welcome home to endless days of sunshine and relaxation. Please see the interactive 3D virtual tour and floor plan. Virtually staged photos are included.

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

Listing Agent: Kay Szinegh (813-918-0624)

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: Great investor or first time home buyer opportunity. This house has new windows, a new roof, updated electric panel and an renovated bathroom. The LVP throughout the home with 5-1/4 baseboard. This property has a huge back yard for your family to enjoy. Built in laundry with washer and dryer included. This property is move in ready and won't last long at this price. Schedule your showing today

Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)

Listing Agent: Stephen Hubbell (863-559-5666)

Remarks: Another Great Listing brought to you by Paul Jacques, P.A. EveryThing Real Estate. Gated Community, Like New. Open floor plan. minutes from downtown Winter Haven. Low HOA, you’ll enjoy neighborhood security and amenities without the extra cost. Commuters will love the quick access to Hwy 27, providing an easy drive to area beaches, Orlando’s theme parks, and more. Price To Sell.

Listing is courtesy of: XCELLENCE REALTY INC. (866-595-6025)

Listing Agent: Paul Jacques (561-441-9695)

Remarks: HUGE $15,000 PRICE DROP! Welcome to this completely renovated 4-bedroom, 3-bath POOL home in the highly desirable Idylridge community of Winter Haven. No expense has been spared in transforming this home into a modern, move-in ready masterpiece with high-end upgrades inside and out. Inside, you’ll find a bright, open layout with all-new paint, luxury vinyl plank flooring, and luxury tile in the bathrooms. Each room features modern ceiling fans, and crown molding throughout, creating both comfort and style throughout the home. The stunning kitchen is a chef’s dream, featuring brand-new stainless steel appliances, granite countertops, a large new island, soft-close cabinet drawers, and a new walk-in pantry. A chef’s natural gas stove lets you cook while enjoying views of the pool and backyard, making this space perfect for entertaining or everyday living. The home offers TWO master suites, one with a large walk-in closet, plus two additional bedrooms and three fully updated bathrooms with contemporary fixtures and backlit mirrors for a sleek, contemporary feel. Step outside to your private backyard oasis with a refreshed pool featuring a brand-new liner, new screen enclosure, and new tile surrounding the deck. The large, fully fenced yard includes partially new fencing and three separate entrances with double gates, ideal for vehicles, boats, or recreational equipment. A 17 x 16 block shed on a slab with a brand-new metal roof provides extra storage or workshop space. Additional highlights include a brand-new roof with new soffit and fascia, two new AC units, new electrical including a 60-amp outdoor generator plug, a three-car carport, and a driveway that fits up to NINE vehicles. Conveniently located in Winter Haven, the home is minutes from shopping, dining, parks, and the Chain of Lakes, as well as attractions like LEGOLAND Florida Resort. This fully renovated, move-in ready pool home offers space, style, and unmatched upgrades—inside and out. Don’t miss your opportunity to own a truly exceptional property in one of Winter Haven’s most sought-after neighborhoods.

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

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