Homes For Sale in Winter Haven 33881 - 308 homes

Remarks: BACK ON MARKET — NOW PRICED UNDER $300K! Seller offering a $5,000 buyer closing cost credit. Occupied Winter Haven duplex generating $2,550/month in gross rental income. Both units are 2 bed / 1 bath and feature stone countertops, laminate flooring, and separate living spaces. No carpet. No HOA. No current vacancy. This property offers immediate income from day one with a practical two-unit setup for long-term rental demand. Located in a quiet residential area less than 2 miles from public schools, near Winter Haven’s Chain of Lakes, Lake Shipp Park, public boat ramps, trails, shopping, dining, and approximately 20 minutes from LEGOLAND Florida. Investors looking for an income-producing asset under $300K should take a serious look. Schedule your showing today.

Listing is courtesy of: BANERSY REAL ESTATE, LLC (407-962-6201)

Listing Agent: Enrique Ojeda (321-946-8241)

Remarks: Lakefront living on the Winter Haven Chain of Lakes takes on a completely different feel at The Guest House , a rare Mid-Century Modern residence designed and built by internationally recognized architect Gene Leedy. Quietly tucked away at the end of a cul-de-sac on the crystal-clear waters of Lake Mirror, the setting feels surprisingly hidden despite being just minutes from shopping, dining, and convenient access to Lakeland, the Polk Parkway, and Interstate 4 for an easy commute between Tampa and Orlando. Originally commissioned for Thelma Guest, "The Guest House" is a striking example of Leedy’s signature architectural style, blending precast concrete construction, dramatic cantilevered forms, walls of glass windows and doors, deep overhangs, and natural light in a way that still feels timeless today. From the street, the design sits perfectly among mature trees and lush landscaping, setting the stage for what awaits inside. The layout was thoughtfully designed around openness, symmetry, and connection to the outdoors. A towering two-story glass entry and interior atrium create an immediate architectural focal point, while the open staircase and original vintage elevator add both character and functionality between levels. The main living spaces are positioned upstairs to maximize natural light and elevated lake views, with expansive glass overlooking the pool, shoreline, and towering oaks draped in Spanish moss. Nearly every upstairs bedroom and living area opens onto long covered balconies, creating seamless indoor and outdoor living. Downstairs offers an entirely different experience with additional flexible living areas surrounding the central atrium and opening directly to the lakefront grounds and pool area . The heated salt-filtered pool feels perfectly integrated into the original architecture, framed by Leedy’s iconic double “T” beam design and expansive covered patios that naturally extend the living space outdoors. The clean geometry, broad overhangs, and shaded entertaining areas create a resort-like atmosphere that feels both private and connected to the lakefront setting. The property itself offers direct frontage on beautiful Lake Mirror , known for its clear water, scenic shoreline, and access to the larger Winter Haven Chain of Lakes — a connected system of more than 20 lakes popular for boating, skiing, fishing, waterfront dining, and exploring by water. A lightly used public boat ramp located immediately next door makes launching effortless without sacrificing usable shoreline space on the property itself. Additional highlights include solar panels, tasteful modern updates, integrated storage and closet systems true to the Mid-Century aesthetic, two covered carports, circular drive, low-maintenance landscaping, and no HOA restrictions. Rarely does a home combine architectural significance, true Chain of Lakes waterfront living, privacy, and Central Florida convenience in such a compelling way. The Guest House is more than a lakefront residence — it is a piece of Winter Haven architectural history.

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

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

Remarks: 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: Rent-to-Own Opportunity! Experience easy Florida living with serene lake views right from the front of this charming home. Bright and welcoming, the home is filled with natural light and features a comfortable, functional layout designed for both everyday living and effortless entertaining. The thoughtfully planned interior offers low-maintenance living without sacrificing comfort or style. A standout feature is the fully fenced yard, providing privacy and versatility—perfect for pets, outdoor gatherings, gardening, or creating your own personal retreat. Combined with the tranquil water views, the outdoor space offers a peaceful and inviting setting. Ideal for first-time buyers, downsizers, seasonal residents, or investors, this property blends charm, flexibility, and scenic surroundings—along with a unique path to ownership in one of Central Florida’s most desirable areas.

Listing is courtesy of: IAD FLORIDA LLC (407-720-0020)

Listing Agent: Catherine Torres (863-632-4177)

Remarks: ** Back to market and reviewing multiple offers: submit all offers by Monday 5:00 pm 5/25/26** Spacious 3-bedroom, 2-bathroom home in Winter Haven priced to sell! This fixer-upper is perfect for investors, flippers, FHA 203(k) buyers, or first-time homeowners looking to build instant equity. With 2,182 sq ft of living space on an 8,442 sq ft lot, this property offers plenty of room for cosmetic and structural improvements. Priced well below market, buyers can capitalize on a significant value-add opportunity in a growing neighborhood. Renovate to create your dream home, or take advantage of strong resale and rental potential.

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

Listing Agent: Daryl Ash, Ii (863-934-1548)

Remarks: Welcome to this beautifully reimagined 4-bedroom, 2-bathroom pool home, perfectly positioned on a premium corner lot. Thoughtfully updated with a new roof (2021), HVAC (2024), and fresh interior paint throughout—including ceilings and the pool deck—this residence offers effortless, move-in-ready living. Inside, a refined layout unfolds with a formal dining space and a flexible bonus room, ideal for a private office or curated living area. The heart of the home showcases an open-concept design, where the living room flows seamlessly into a sophisticated kitchen and breakfast space, perfect for both intimate gatherings and entertaining. The kitchen is appointed with quartz countertops, high-end appliances, a built-in bar fridge, and a convenient pot filler, blending style with function. A desirable three-way split floor plan ensures privacy and comfort throughout. Outdoors, enjoy a screened-in patio overlooking a sparkling pool, complemented by a generously sized, fully fenced backyard, your own private retreat designed for the Florida lifestyle. Experience the perfect blend of modern upgrades and timeless comfort. Schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Kevin Asenjo (407-844-5252)

Remarks: Welcome to 292 Krenson Bay Loop, a 2024-built block home located in a gated Winter Haven community with NO CDD! This 4-bedroom, 2-bath home offers 1,820 square feet of living space, a 2-car garage, irrigation system, and a desirable split floor plan designed for comfort and functionality. Inside, you’ll find tile throughout the main living areas and kitchen, with carpet in the bedrooms. The modern kitchen features stainless steel appliances, subway tile backsplash, a large pantry, and an oversized peninsula with bar seating, opening nicely to the breakfast nook and main living area. A formal dining room provides additional space for gatherings or flexible use. The primary suite includes a walk-in closet and private bath with dual sinks, a garden tub, and a separate shower. Enjoy Florida living from the covered lanai, perfect for relaxing outdoors. Located in Winter Haven, this home offers convenient access to local lakes, shopping, dining, medical facilities, and nearby attractions including LEGOLAND Florida Resort. With easy routes to Lakeland, Tampa, and Orlando, this location provides a great balance of Central Florida living and regional convenience.

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

Listing Agent: Garrett Robinson (863-838-5210)

Remarks: Prepare to be captivated by this beautifully updated lakefront estate on Lake Hartridge, perfectly positioned along the highly sought-after Winter Haven Chain of Lakes. Situated on approximately 1.3 acres with an impressive 115 feet of waterfront, this exceptional property offers a rare combination of luxury, privacy, and breathtaking panoramic water views, all tucked away on a peaceful dead-end street. Mature oak trees and lush tropical landscaping create a timeless Old Florida ambiance while blending seamlessly with the home’s fresh, modern updates. A long private driveway welcomes you to the property, leading to an oversized detached two-car garage complete with a private apartment above—ideal for guests, multigenerational living, rental income, or a secluded home office—and a convenient full bathroom below. Inside the main residence, an expansive and thoughtfully designed floor plan features four spacious bedrooms and 4.5 beautifully appointed bathrooms. One bedroom is currently styled as a cozy movie room, creating the perfect entertainment space for relaxing evenings or family gatherings. The luxurious first-floor primary suite serves as a true retreat, offering a spacious sitting area with stunning views overlooking the sparkling screened pool and tranquil lakefront setting. The spa-inspired primary bathroom showcases a soaking tub, oversized walk-in shower, elegant dual vanities, and generous space designed for comfort and relaxation. At the center of the home is the beautifully updated gourmet kitchen, featuring sleek quartz countertops, modern cabinetry, stainless steel appliances, and abundant prep and storage space sure to impress any chef. Elegant porcelain flooring flows throughout the main living areas, while plush carpeting adds warmth and comfort to the bedrooms. Recent upgrades, including a new roof and new AC system, provide peace of mind and enhance the home’s fresh, move-in-ready appeal. Designed to maximize the spectacular lake views, the expansive lanai and private screened-in pool area with an in-ground hot tub create the ultimate outdoor oasis for year-round Florida living. Newly refreshed pool and lanai screening further elevate the experience, seamlessly blending indoor and outdoor entertaining spaces. For boating enthusiasts, the property truly stands out with a private covered dock featuring a metal roof and boat lift, offering direct access to the renowned Winter Haven Chain of Lakes, known for boating, fishing, watersports, and unforgettable sunset cruises. Additional highlights include dedicated RV parking with electrical, water, and sewer hookups, making this property ideal for those seeking adventure without sacrificing luxury and convenience. Located in the heart of Winter Haven, known as the “Chain of Lakes City,” residents enjoy easy access to over 50 interconnected lakes, waterfront dining, boutique shopping, recreational trails, and convenient access to both Tampa and Orlando attractions. This extraordinary lakefront estate perfectly combines modern updates, timeless elegance, and resort-style living—offering a truly rare opportunity to own a one-of-a-kind waterfront retreat.

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

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

Remarks: Discover the best of retirement living in Brookhaven, a welcoming 55+ community! This partially furnished and well-maintained home sits on a desirable lot with OWNED LAND, offering a peaceful and private retreat.Featuring 1,596 sq. ft. of living space, this home boasts a spacious open-concept layout with 2 bedrooms and 2 bathrooms. Recent updates include a new shingle roof (2024), new A/C unit (2025), and hot water heater (2023). The kitchen offers ample counter space and cabinetry, perfect for everyday living and entertaining.Enjoy plenty of storage throughout, along with sliding doors that lead to the porch—ideal for relaxing or hosting guests. The guest bedroom and bathroom are generously sized, while the oversized primary suite features a private ensuite bath complete with a double-sink vanity, garden tub, and walk-in shower.The laundry area is conveniently located in the spacious workshop and includes a washer, dryer, and utility sink. This home also features two porches—one screened and one enclosed—providing additional living space to enjoy year-round.Surrounded by mature landscaping, the property offers both charm and tranquility. Additional perks include an irrigation system and lawn maintenance already paid through February. This home has recently had a 4-point inspection.Brookhaven residents enjoy fantastic amenities including a pool, clubhouse, and shuffleboard—all with a low HOA fee of just $34 per month. Conveniently located near Hwy 27, shopping, medical facilities, and restaurants, you’re also just about an hour from Disney and 1.5–2 hours from both Florida coasts.Don’t miss your opportunity to own this beautiful home at 6561 Chinaberry Dr NE — schedule your private showing today!

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

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

Remarks: One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 2-bath home in Winter Haven offering 1,334 sqft of comfortable living space; this well-designed home features a functional layout for everyday living, with a bright and inviting living area that flows seamlessly into the dining and kitchen spaces; the bedrooms provide flexibility for family, guests, or a home office, while the 1-car garage adds convenience and additional storage; whether you’re a first-time buyer or looking to downsize, this home offers great potential in a desirable location—don’t miss out, schedule your private showing today!

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

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

Remarks: LAKEFRONT COMMUNITY...Welcome home to Lakeside Ranch, a gated 55+ community with NO LOT RENT! This 2 Bedroom/2 Bath home features a large living room that leads to the lovely Florida room.This open concept home has a tastefully renovated kitchen with lots of counterspace and cabinets, a dining room with built-in cabinetry, a large living room with lighted ceiling fan, luxury vinyl plank flooring throughout. Utility shed all offers additional storage space and includes washer and dryer. Sold Furnished or Vacant, your choice. HOA inscludes water, sewer, lawn service and security. The community features a large clubhouse with a variety of scheduled activities and holiday events, library, meeting space, a boat ramp and fishing dock on Lake Henry, trailer storage area, heated swimming pool, shuffleboard, horseshoe area, and a billiards room. Are you ready for an active lifestyle? Or just relax and fish the day away? This is the place for you either way! Live here year-round or escape the cold winters in sunny Florida!

Listing is courtesy of: HOME WISE REALTY GROUP, INC. (407-712-2000)

Listing Agent: Chanmarlie Lim (407-376-1813)

Remarks: This approximately 1,730-square-foot home offers three bedrooms and two bathrooms in a gated community close to bike trail. The home features a clean and bright interior with almost new condition, ready for immediate move-in. The property has no CDD fees and is conveniently located close to various amenities. The home also has solar panels and a lower assumable mortgage interest rate, providing potential cost-saving benefits for the next owner. Ask me how! The three bedrooms provide comfortable living spaces, with the primary bedroom offering seclusion and ample square footage. The two bathrooms are well-appointed and maintained, catering to the needs of the household. The open floor plan creates a seamless flow throughout the living areas, enhancing the sense of space and natural light. The exterior of the home presents a well-kept and inviting appearance, with the lot size providing a manageable outdoor space complete with covered patio. The convenient location of the home allows easy access to various services, shops and other community resources, making it an ideal choice for those seeking a practical and comfortable living situation.

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

Listing Agent: Susan Brown (863-640-5722)

Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning Winston floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 5-bedroom, 3-bath home offers 2,531 square feet of living space, and providing excellent curb appeal in it's elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz counter tops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarena on the Lakes. This well-designed home offers an impressive blend of indoor and outdoor living spaces. The main level features a formal living room with a fireplace and wet bar, a dining area, a functional kitchen with breakfast bar, a guest half bath, and two private outdoor living areas. An attached two-car garage provides added convenience. Upstairs, you’ll find two spacious bedroom suites each with a private en-suite bath, as well as a versatile loft area. Step out to the screened balcony or the open upper deck, perfect for enjoying tranquil lake views and evening breezes. Community amenities include a swimming pool with spa, tennis court, lakeside dock, beach area, and a gated entry with electronic access. Whether you're seeking a seasonal retreat or a full-time residence, this unique property offers comfort, style, and a desirable location.

Listing is courtesy of: DREAM BUILDERS REALTY (407-847-5428)

Listing Agent: Tim Weisheyer (407-847-5428)

Remarks: This 4/2 home has a renovated interior showcasing modern upgrades throughout. The home features stunning new 36" x 24" porcelain tile flooring, offering a sleek, contemporary look with durability and easy maintenance. Move-in ready and designed for comfortable, stylish living. Dual access bedroom and bath provides the bedroom with private ensuite access while allowing the bathroom to serve as a main or guest bathroom from the hall, featuring two doors to maximize access and functionality. Large kitchen with island and lots of cabinet space and large pantry. Sliding doors leading to covered screened in porch with additional concreted tiled patio area that leads to a large backyard. Seller will consider contributing toward buyer’s closing costs.

Listing is courtesy of: EASY REALTY (321-895-4636)

Listing Agent: Greg Owen (321-360-4434)

Remarks: One or more photo(s) has been virtually staged. Welcome to the Mulberry floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2.5-bath home offers 1,938 square feet of living space and provides excellent curb appeal in its elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: One or more photo(s) has been virtually staged. Charming single-story home located in Winter Haven with a functional layout and comfortable living spaces throughout. This 3-bedroom, 1-bath property features an inviting living area filled with natural light, a spacious kitchen with ample cabinet and counter space, and tile flooring throughout for easy maintenance. The home also offers a covered parking area, paved driveway, and a generously sized yard with room to enjoy outdoor living. Conveniently located near shopping, dining, parks, lakes, and major roadways for an easy commute throughout Polk County.

Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)

Listing Agent: Raquel Littlejohn (470-279-6333)

Remarks: One or more photo(s) has been virtually staged. Welcome to 306 Ave P NW – a fantastic opportunity for first-time home buyers or savvy investors! Now offered as separate units for added affordability and flexibility, this property is perfect for buyers looking to own instead of rent. This well-maintained home features bright living spaces, functional layouts, and great potential to personalize and build equity. Whether you’re looking for your first home, a mortgage helper opportunity, or an affordable investment, this property checks all the boxes. Located in a convenient neighborhood close to schools, parks, shopping, and everyday amenities, you’ll love the value and potential this property offers. Why rent when you can own? Don’t miss your chance to get into the market with this affordable and versatile property. Quick possession available — motivated seller!

Listing is courtesy of: TRUE FLORIDA REALTY LLC (863-337-9667)

Listing Agent: Ricky Miller, Jr (407-453-8679)

Remarks: Welcome to 2213 Rose Blvd in Winter Haven—a beautifully maintained and like-new 4 bedroom, 2 bath home offering over 1850 square feet of comfortable living within the Buckeye Ridge community. Perfectly positioned on a corner lot, this home showcases outstanding curb appeal and evident pride of ownership, enhanced by a freshly painted exterior accents, well cared for landscaping, decorative gable vents and carriage-style garage hardware for a custom look. A thoughtfully designed split-bedroom layout with open-concept living at its core, offering a seamless flow for everyday living and entertaining while maintaining privacy with a well-separated primary suite and generously sized secondary bedrooms. Tile flooring leads from the foyer into the great room and kitchen area, where brand-new wood laminate flooring and roomy dimensions provide an ideal level of easy living. The kitchen features an abundance of cabinetry and counter space, breakfast bar/center island, a walk-in pantry and included appliances. Dining space sits just off the kitchen with tranquil backyard views. The triple split-bedroom layout provides privacy and flexibility, highlighted by a generously sized primary suite with brand-new carpeting, a walk-in closet, and an en-suite bath complete with dual vanities, walk-in shower, large linen closet and private water closet. All guest bedrooms also have brand new carpeting and are spacious with easy access to the full guest bath. Step outside to your private outdoor oasis—featuring a screened patio that opens to a fully fenced backyard with vinyl fencing and irrigation system with timer to keep the yard green and lush—perfect for relaxing or hosting gatherings year-round. Additional notable features include an inside laundry room, double-pane windows, two-car garage, warranties on the new flooring, both gas and battery generator connections and a transfer switch for added peace of mind. Location is everything, and this home delivers—just minutes from vibrant downtown Winter Haven, Polk State College, medical facilities, shopping, restaurants as well as multiple golf courses and lakes to fully enjoy the Central Florida lifestyle. Centrally located between Orlando and Tampa, Winter Haven offers the perfect balance of small-town charm with convenient access to major roadways, shopping, dining, and world-class attractions. Homes in this condition with an ideal combination of upgrades and location are hard to find—schedule your private showing today!

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

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

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)