Homes For Sale in Winter Haven 33881 - 312 homes

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 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: 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: 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: 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)

Remarks: Best Deal in Polk County!!!! Highly desirable 55+ Brookehaven Village community! This charming 2-bedroom, 2-bathroom manufactured home offers comfortable Florida living with a spacious Florida room, a versatile cabana room, and a convenient laundry/utility room. The home includes some furnishings, making your move even easier. With just a little dusting and cleaning, this property is ready to shine and become the perfect full-time residence, seasonal Florida retreat, or investment opportunity. Conveniently located near shopping, dining, medical facilities, and everyday amenities, while also featuring exceptionally low HOA fees. Priced for a quick sale, this is an opportunity you won't want to miss. Schedule your private tour today!

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

Listing Agent: Steve Donahue (863-251-9943)

Remarks: Investors Only. Leased through August 31, 2027, at $2,575/month. Landlord provides lawn care. No rear neighbors and entirely fenced for privacy! Low HOA dues and bonus room/loft plus office space. Open concept with luxury laminate flooring throughout including stairs. Full-sized kitchen island with seating and plenty of counter space for food prep. Stainless steel appliances. The dining and family room combo offers plenty of natural lighting with slider glass doors leading to your outdoor patio overlooking the conservation area. The master bathroom features two (2) walk-in closets. Enjoy the early morning sunrises sitting under your custom-built pergola in back. Screened front porch. Located 6 miles from Legoland Theme Park and Water Park.

Listing is courtesy of: 3% REAL E$TATE (407-479-0076)

Listing Agent: Ray Guenther (407-479-0076)

Remarks: Welcome to 1716 Terry Circle NE, Winter Haven, FL 33881, a beautifully maintained and fully furnished home offering the perfect blend of comfort, convenience, and investment potential. This move-in-ready property features ceramic tile flooring throughout, updated bathrooms, and a bright, open floor plan with spacious living and dining areas that flow seamlessly into a large kitchen with breakfast bar seating and all stainless steel appliances included. The thoughtfully designed layout provides privacy for the primary bedroom, separating it from the additional bedrooms to create a peaceful retreat. Tasteful furnishings and décor are included, making this a truly turnkey opportunity for homeowners, seasonal residents, or investors alike. The neutral color palette, abundant natural light, and functional layout create a warm and inviting atmosphere ideal for everyday living or entertaining guests. One of the home's most attractive features is the absence of HOA fees and restrictions, offering greater flexibility and freedom for the new owner. Conveniently located in the heart of Winter Haven, the property is just minutes from LEGOLAND Florida Resort and Peppa Pig Theme Park Florida, making it an excellent choice for vacation home buyers and visitors. Residents will also enjoy easy access to the Winter Haven Chain of Lakes, offering endless opportunities for boating, fishing, and outdoor recreation. Nearby shopping, dining, schools, medical facilities, and the vibrant downtown district provide everything needed for comfortable Florida living. With convenient access to major highways connecting Orlando and Tampa, this fully furnished home presents a rare opportunity to own a turnkey property in one of Central Florida’s fastest-growing and most desirable locations. Schedule your private showing today and discover all that this exceptional home has to offer.

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

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

Remarks: Welcome Home to your 3 bedroom/2 bath home! NEW luxury vinyl plank flooring and freshly painted throughout, granite in the kitchen and baths, new lighting, 6-panel doors and ceiling fans. Kitchen has new cabinets and newer stainless-steel appliances. The Primary Suite features lots of light, double vanities and walk-in shower. The flex room connected to the Primary Suite would be perfect for an office, reading room, playroom, craft room or a nursery. Two additional bedrooms and hall bath round out this concrete block home located just west of Winter Haven and within minutes from numerous lakes. Close to major thoroughfares, restaurants, and shopping.

Listing is courtesy of: POWERS REAL ESTATE SOLUTIONS LLC (904-703-0905)

Listing Agent: Lynne Powers (904-703-0905)

Remarks: Experience luxury living in this newly built (2023) modern style home featuring breathtaking views of Lake Jessie and no HOA! This spacious 4-bedroom, 4-bath single-family residence offers an expansive open floor plan, soaring ceilings, and porcelain tile throughout. The elegant living room features a dramatic porcelain tile fireplace, creating a warm and stylish focal point. The chef’s kitchen is designed to impress with quartz countertops, stainless steel appliances, sleek modern cabinetry, and ample storage. A spacious indoor laundry room adds everyday convenience. Additional highlights include a 3-car garage, durable tile roof, whole-home water filtration system, and pre-wiring for a security camera system. Enjoy year-round outdoor living with a fully enclosed porch and large paver patio—perfect for relaxing or entertaining. Conveniently located directly across from a public boat ramp, offering easy access to boating and recreation without the upkeep of lakefront ownership. An exceptional opportunity to own a move-in-ready home with thoughtful upgrades, modern design, and a prime location near the water. Schedule your private showing today!

Listing is courtesy of: LANTES REAL ESTATE LLC (813-408-0980)

Listing Agent: Asley Garcia (813-613-2666)

Remarks: LEASE to OWN option available!!! Welcome to 2826 Ave Q NW in Winter Haven — a beautifully remodeled 3-bedroom, 1-bath home designed for comfort, functionality, affordable and modern living. This move-in-ready property features a brand-new roof, updated HVAC system, and new energy-efficient windows, new stainless steel appliances, new granite countertops, new porcelain tile flooring, and so much more! This home offers both peace of mind and long-term value. Inside, you’ll find a thoughtfully refreshed interior with clean finishes and a layout that maximizes space and natural light. Ample storage is a standout feature throughout the home, making it easy to stay organized and clutter-free. The attached carport provides convenient parking along with additional storage space, ideal for tools, equipment, or seasonal items. Situated in a well-connected area of Winter Haven, this home places you close to a variety of everyday conveniences and lifestyle destinations. Enjoy easy access to shopping, dining, and local favorites, as well as major roadways for commuting. Nearby attractions include LEGOLAND Florida Resort, offering entertainment and recreation just a short drive away. The property is also located near reputable healthcare facilities such as Winter Haven Hospital, ensuring accessibility to medical services when needed. A variety of restaurants, parks, and outdoor spaces are within reach, providing options for dining and leisure. Whether you're looking for a primary residence or an investment opportunity, this updated home offers a solid combination of location, upgrades, and everyday convenience. Schedule your private showing today.

Listing is courtesy of: OPULENT REALTY INTERNATIONAL (863-323-7778)

Listing Agent: Alicia Self (863-450-8394)

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: Come see 1100 Carefree Cove Dr, recently improved with a new roof, fresh exterior paint, and fresh interior paint, presenting a comprehensively refreshed presentation. Partial flooring replacement further updates the interior living spaces, while a fenced in backyard provides practical outdoor areas. This property embodies a fresh approach to comfortable living. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: One or more photo(s) has been virtually staged. Beautifully remodeled in 2024, this move-in ready home offers modern updates, energy efficiency, and timeless comfort—all with no HOA. Step inside to an open-concept floor plan featuring high ceilings and abundant natural light. The brand-new kitchen impresses with contemporary finishes, while the updated bathrooms offer a fresh, stylish feel. A desirable split floor plan provides added privacy, making the home ideal for both families and guests. Major improvements include a newer roof and full re-plumbing, giving peace of mind for years to come. The home is also equipped with solar panels for low-cost energy, along with a natural-gas stove and gas water heater—perfect for efficiency and everyday convenience. Outside, enjoy great curb appeal, a fully fenced backyard for pets or play, and a spacious attached 2-car garage. With no HOA restrictions, you have the freedom to personalize, park, and use your property exactly the way you want. This beautifully updated home truly checks every box—style, function, efficiency, and freedom.

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

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

Remarks: Under contract-accepting backup offers. Enclosed Saltwater Pool | Corner Lot | 4 Bedrooms in Winter Haven - New Roof May 2026! Welcome to 310 17th St NE in Winter Haven, FL — a charming 4-bedroom, 2.5-bath pool home set on a spacious 0.28-acre corner lot in an established neighborhood. This home offers a blend of character, space, and opportunity for the next owner. Inside, you'll find nearly 1,800 sq ft of living space with a functional layout that includes four bedrooms, 2 full bathrooms and a convenient half bath, offering flexibility for guests, home office space, or everyday living. The kitchen and bathrooms retain their original style, giving buyers the chance to update and personalize over time. Step outside and enjoy the enclosed saltwater pool (installed in 2018), creating a private outdoor space for relaxing or gathering with friends. The fenced backyard and large corner lot provide room to spread out and enjoy outdoor living. Major systems have already been updated, including AC (2020) and water heater (2018). The home also offers 2,267 total square feet under roof, adding additional usable space. FHA Appraisal came in at $322k! Conveniently located near shopping, dining, schools, and major roadways, this property combines the charm of an established Winter Haven neighborhood with everyday convenience.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Jenelle Grabowicz (863-604-0834)

Remarks: Welcome to refined Florida living in the serene, gated, 55+ community of Preserve at Lakeside Landings. This community designed with enjoying your Florida lifestyle, is home to 44 residences, 2 pools, a playground, and sidewalks to keep you active. HOA includes lawn maintenance which allows you to relax in your stunning new home! Thoughtfully designed with a triple-split floorplan, this residence offers exceptional privacy and versatility—ideal for multi-generational living. Manicured tropical landscaping and pristine sidewalks lead you inside, where the first split features two guest bedrooms and a shared bathroom. Continuing into the main corridor, you’ll find the third bedroom or office along with the conveniently located laundry room.The home then opens into a bright, airy living space with 9-foot ceilings and tile flooring. An elegant dining area overlooks the pool, while the beautifully appointed kitchen showcases solid wood cabinetry, granite countertops, stainless steel appliances, and a generous island perfect for entertaining. The primary suite serves as a peaceful retreat with updated flooring, a walk-in closet, and a spa-inspired bath complete with dual sinks, granite, and a glass walk-in shower. Outdoors, the property transforms into a true tropical sanctuary. A stunning saltwater pool with a cascading waterfall is framed by lush landscaping that is home to several citrus trees. This secluded, spa-like atmosphere is ideal for relaxation or entertaining. With a tranquil natural backdrop and effortless indoor-outdoor flow, this home blends elegance, comfort, and resort-style appeal. Fresh interior paint, an immaculate garage, energy-efficient insulation, and lawn care included in the HOA make this home truly move-in ready—offering a lifestyle of ease, beauty, and authentic Florida living. Upgrades include kitchen appliances 2025, new disposal, Pentair salt system is 4 years old. Pool deck was sealed one year ago. Don't hesitate, opportunities like this are rare, so make your appointment today!

Listing is courtesy of: FLORIDA REAL ESTATE COMPANY (863-701-3487)

Listing Agent: Cyleste Goodson (863-701-3487)

Remarks: Charming 3-bedroom, 1-bath home with no HOA, offering a great opportunity for investors or first-time buyers alike. Conveniently located in Winter Haven with easy access to shopping, dining, schools, major roadways, and everyday amenities. This property offers plenty of potential and is ideal for those looking to expand their portfolio or create a place to call home.

Listing is courtesy of: JOSEPH WALTER REALTY LLC (248-294-7850)

Listing Agent: Scott Fader (248-294-7850)

Remarks: OWNER FINANCING AVAILABLE ~ 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: Motivated Seller. Introducing a beautifully maintained home offering an excellent and functional layout. The first floor features a welcoming open concept with a half bathroom, living, dining, and kitchen areas, and a well-appointed kitchen with granite countertops, stylish backsplash, and elegant lighting fixtures. A sliding glass door brings in natural light and provides direct access to the backyard, enhancing the indoor-outdoor connection. The entire main level is finished with tile flooring, providing durability and easy maintenance. Upstairs, you will find three generously sized bedrooms and a versatile loft area, ideal for a playroom, home office, or study space. The primary suite offers a comfortable retreat with a barn door leading into the bathroom, which is also well-designed and spacious. The second and third bedrooms are well sized and highly versatile. This home has been very well cared for and is move-in ready. Enjoy a large backyard, perfect for entertaining, family gatherings, or simply relaxing outdoors. A great opportunity to own a home with space, comfort, and thoughtful design throughout. Schedule your private showing today.

Listing is courtesy of: HOMETRUST REALTY GROUP (813-444-5777)

Listing Agent: Barbara Prins (407-361-6061)