Winter Haven Homes For Sale & Real Estate - 1035 homes

Remarks: 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: Here we go, back to market, Buyer default! The property you are inquiring about is located in Winter Haven, FL, in the Winter Haven Harbour area of Polk County. Now conveniently located is this corner unit with beautiful window views from the third floor, and with recent updates. The A/C is newly installed (Dec 2025). Two bedrooms, 1 bath, with every square inch utilized for practical purposes. The community is a 55+ and is conveniently located in the heart of convenience. The HOA fees are low by comparison to what is included in the fee. Vacant and ready for occupancy. Text or call for your private viewing. *Agents, please read MLS remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: Virtually Staged. Welcome to this beautifully updated, 5-bedroom, 3-bath home built in 2022, located in the sought-after Pinnacle Point community of Winter Haven. This home offers a spacious open floor plan filled with natural light and designed for comfortable everyday living. The kitchen features sleek finishes, modern appliances, and a large island that opens seamlessly to the main living and dining areas, making it ideal for both daily life and entertaining. The downstairs includes a bonus room, a full guest bathroom, and a guest bedroom, adding excellent flexibility for visitors or multi-generational living. Upstairs, a versatile loft provides additional living space perfect for a media room, office, or play area. The primary suite offers a private retreat with a large walk-in closet and a well-appointed bathroom, while the additional bedrooms provide plenty of space and versatility. The home features durable vinyl flooring throughout with no carpet,Welcome to this beautifully updated 5-bedroom, 3-bath home in the sought-after Pinnacle Point community of Winter Haven. This home offers a spacious open floor plan filled with natural light and designed for comfortable everyday living. The kitchen features sleek countertops, modern appliances, and a large island that opens seamlessly to the main living and dining areas, making it ideal for both daily life and entertaining. Upstairs, a versatile loft provides additional living space for a media room, office, or play area. The primary suite offers a private retreat with a large walk-in closet and well-appointed bath, while the additional bedrooms provide plenty of space and flexibility. The home features durable vinyl flooring throughout with no carpet, adding to its clean and low-maintenance feel. Step outside to a generously sized backyard, perfect for outdoor gatherings, pets, or relaxing evenings under the Florida sky, with a soon-to-be fully fenced setup adding even more privacy and usability. Located close to LEGOLAND Florida Resort, shopping, dining, and medical facilities, and conveniently positioned between Tampa and Orlando, this home offers both comfort and convenience in a growing Central Florida location.

Listing is courtesy of: ROBERT SLACK LLC (954-448-4287)

Listing Agent: Garrett Miller (727-339-2439)

Remarks: This well-maintained 4-bedroom, 3-bathroom pool home is located in the sought-after gated community of Tuscany at Winterset, offering both comfort and style in a prime setting. Inside, you’ll find an inviting layout highlighted by solid surface countertops, elegant tray ceilings, and detailed crown molding that adds a refined touch throughout the living spaces. Major updates provide peace of mind, including new windows (2025), a newer roof (2021), kitchen remodel (2023) and an updated HVAC system (2023). Step outside to enjoy the brick-paved driveway and your own private pool (2020)—perfect for relaxing or entertaining. This home combines thoughtful upgrades, functional features, and a desirable location—an excellent opportunity in one of the area’s most desirable gated communities.

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

Listing Agent: Tony Insua, Jr (863-221-0656)

Remarks: Location is Key! NO HOA! New Roof, New AC, 3 New Bathrooms, New Front Door, New Floors etc. Next to Polk State College, Lake Elbert Walking Path, Boat Launch and only 2 miles from Downtown Winter Haven. Fresh paint inside and out. The West side of the house has its own access if you want to use the 3rd bedroom as a mother-in-law suite or rent it out privately. The house access is through the newly paved back alley with a large carport in a quiet neighborhood. This house is a great place for a family or someone looking to enjoy the lake, walking path, quiet neighborhood or outdoors.

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

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

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: ARE YOU LOOKING FOR A GATED COMMUNITY WITH A LOW HOA and NO CDD? At 116 Mandolin Dr in WINTER HAVEN, FL! This spacious 4-bedroom, 2-bathroom home offers 2,248 square feet of COMFORTABLE LIVING on a generous 0.26-acre lot! Step inside to soaring VAULTED CEILINGS in the living and dining areas—these ELEVATED CEILINGS create an open, airy feel that makes the home even larger than its footprint. The entire home features durable VINYL FLOORING, and all bedrooms are generously sized, offering FLEXIBILITY FOR FAMILIES, guests, or a home office. NATURAL LIGHT pours in throughout the home, creating a bright and welcoming atmosphere that’s perfect for new homeowners. Major updates include a NEW A/C SYSTEM (2025) and GUTTERS INSTALLED (2024), while the WATER HEATER was replaced in 2017. The roof and plumbing are original, but the seller is willing to NEGOTIATE A BRAND NEW ROOF — making this property an UNBEATABLE VALUE for the price. Situated in a quiet gated community, this property offers both privacy and security. The location is a standout—just a short walk from a newly constructed Publix set to open in the coming months, as well as nearby Dollar General and 7-Eleven for everyday convenience. You’re also just minutes away by car from Eagle Ridge Mall, LEGOLAND Florida Resort, and all the shopping, dining, and entertainment that downtown Winter Haven has! —making this home not only comfortable, but perfectly located.

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

Listing Agent: Nomar Rosa (646-673-3900)

Remarks: Located in the highly sought-after gated community of Lakewood, this beautifully maintained home offers 4 bedrooms and 3.5 bathrooms, set on a lush, manicured lot with mature trees and attractive landscaping. Inside, you’ll find rich wood flooring throughout the spacious living and dining areas, as well as the kitchen and family room—perfect for both everyday living and entertaining. A standout feature is the expansive 480 sq ft detached game room, included in the total living area, complete with a full bathroom and generous closet space—ideal for conversion into a private guest house, in-law suite, or home office. The primary suite boasts a recently renovated en-suite bathroom and direct access to the large screened lanai and pool area, creating a relaxing retreat. Major updates include a roof replacement in 2017. This exceptional property offers space, flexibility, and charm—don’t miss your opportunity to make it yours!

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

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: ANOTHER PRICE IMPROVEMENT. ONCE IN A LIFETIME OPPORTUNITY! CAN'T BEAT THIS PRICE IN THIS COMMUNITY!!! This is a charming 2-bedroom, 2-bath home in a desirable adult living gated community. This well-kept residence features a spacious master suite with a walk-in shower, a bright and open living area, and a functional kitchen perfect for everyday living. Step outside to a screened-in back porch—ideal for relaxing or entertaining in comfort. Enjoy the many amenities this active community has to offer, including a clubhouse, pool, fitness center, and social activities designed to enhance your lifestyle. Comfort, convenience, and community await you at Vienna Square!

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

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

Remarks: Virtually Staged. Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the desirable Winter Haven area! This move-in ready property offers a perfect blend of comfort, style, and modern updates throughout. From the moment you step inside, you’ll notice the upgraded accent wall paneling featured in the foyer, dining room, and spacious primary bedroom, adding warmth and custom character to the home. The dining room and foyer have also been enhanced with updated light fixtures that provide a fresh, elegant touch. Pride of ownership is evident throughout, as this home has been exceptionally well maintained and cared for. With inviting living spaces, a functional layout, and tasteful upgrades, this home is ideal for both relaxing and entertaining. Conveniently located near shopping, dining, schools, and major roadways, this property combines comfort and convenience in one attractive package. Don’t miss your opportunity to own this charming Winter Haven home — schedule your private showing today!

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

Listing Agent: Matt Everett (231-563-3176)

Remarks: Welcome to 287 Inman Blvd—where modern comfort meets effortless Florida living in the heart of Winter Haven. This beautifully maintained home truly feels like new, offering the peace of mind of recent construction with thoughtful upgrades already in place. In addition to the home’s like-new condition and thoughtful upgrades, qualified buyers may also have the rare opportunity to assume the seller’s existing 5.125% mortgage — potentially creating estimated monthly savings of more than $250 compared to many current market interest rates. From the moment you step inside, you’ll notice a clean, contemporary design paired with warm, inviting spaces. The open-concept layout flows seamlessly, making it perfect for both everyday living and entertaining. The kitchen is a standout feature, enhanced with a stylish backsplash on the island and throughout, complemented by upgraded light fixtures that add a polished, custom feel. The home also features low-maintenance quartz countertops as well as stainless steel appliances. This home has already been elevated beyond builder-grade with valuable improvements, including solar panels for energy efficiency, a vinyl privacy fence for added outdoor enjoyment, and upgraded ceiling fans and lighting throughout. Tile flooring in the wet areas offers durability and easy maintenance, while cozy carpeting in the bedrooms creates a comfortable retreat at the end of the day. Step outside and enjoy a backyard space that’s ready for relaxing evenings, pets, or gatherings—fully enclosed for privacy and convenience. Location is where this home truly shines. Situated just about one and a half miles from the soon-to-open Publix shopping plaza, you’ll have everyday essentials right around the corner. Plus, you’re only minutes from downtown Winter Haven, known for its charming local shops, dining, and access to the Chain of Lakes lifestyle. Commuters will appreciate the quick access to US-27, making travel to surrounding areas simple and efficient. If you’ve been searching for a move-in-ready home with upgrades already done, modern finishes, and a prime location, this is one you don’t want to miss.

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Chris Loschiavo (863-280-2201)

Remarks: NO HOA + POOL HOME + MINUTES TO THE CHAIN OF LAKES! This updated 4-bedroom, 3-bath Winter Haven home delivers the Florida lifestyle buyers are searching for — a heated private pool, oversized fenced backyard, flexible living space, and quick access to the Lake Summit boat ramp and the Winter Haven Chain of Lakes. Bring the boat, jet skis, trailer, golf cart, pets, and weekend plans because this property gives you room to enjoy it all. Inside, the home offers nearly 2,500 sq ft of living space with a bright, open feel, luxury vinyl flooring, oversized living and dining areas, and a beautifully updated kitchen featuring quartz countertops, custom soft-close cabinetry, stainless steel appliances, and a premium Ruvati workstation sink. The layout includes two private ensuite bedrooms, making it ideal for multigenerational living, guests, teenagers, extended family, or a private work-from-home setup. The spacious primary suite feels like its own retreat with tray ceilings, a large walk-in closet, dual vanities, soaking tub, and walk-in shower. Step outside to the screened lanai overlooking the heated inground pool and large backyard — perfect for cookouts, pool days, entertaining, or quiet evenings after a day on the lakes. Boat ramp is only 2 blocks away. Major updates include roof 2019, whole-house replumb 2019, AC handler 2019, water heater 2019, remodeled kitchen 2021, luxury vinyl flooring 2021, Raypak pool heater 2022, variable-speed pool pump 2024, irrigation system 2024, and guest bathroom remodel 2025. Located in desirable SE Winter Haven near Legoland, shopping, dining, medical, schools, and less than 2 minutes from Lake Summit boat ramp with access to the Chain of Lakes for boating, fishing, skiing, and waterfront dining. This is the kind of home that checks the boxes: updated, spacious, no HOA, pool, fenced yard, and close to the water.

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

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

Remarks: Virtually Staged. Fully refreshed and move-in ready, this Ruby Lake home delivers space, thoughtful upgrades, and a layout that stands out from the rest. Offering high ceilings and a well-designed flow from the L-shaped formal living room that transitions into the formal dining area, creating a defined yet open feel. The kitchen sits at the center with a dinette overlooking the family room. A standout feature is the seamless connection to the outdoor space, with three separate access points to the 33x10 screened-in lanai, from the dinette, formal dining area, and primary suite—creating true indoor-outdoor living. The kitchen has been tastefully updated with brand new granite countertops, new range, and new microwave, along with ample cabinetry, a closet pantry, and breakfast bar. The primary suite is generously sized and opens into an en-suite featuring dual walk-in closets, split vanities, a garden tub, walk-in tile shower, and a private water closet. The split-bedroom floor plan offers privacy, while all bedrooms include walk-in closets. Recent improvements make this one stand out from others in the neighborhood, including brand new carpet throughout, fresh interior paint, and a new water heater, giving buyers peace of mind from day one. Located in the gated Ruby Lake community in Southeast Winter Haven, just minutes from convenient access to shopping, dining, Publix, Walmart, Legoland, and Hwy 27 for an easy commute.

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Don’t miss this beautifully renovated 2-bedroom, 1-bath home conveniently located near downtown Winter Haven and just minutes from Polk State College. Whether you’re a first-time homebuyer, downsizing, or looking for a great investment property, this home offers exceptional value and is priced to sell. Recent updates provide a fresh, modern feel throughout, making this property truly move-in ready. Enjoy the convenience of a covered carport, a spacious screened patio perfect for relaxing or entertaining, and a large backyard with plenty of room for outdoor activities, pets, or future improvements. With its prime location, updated condition, and strong rental potential, this home is an excellent opportunity for both homeowners and investors alike. Schedule your private showing today before it’s gone! Some photos have been virtually staged

Listing is courtesy of: OFFERPAD BROKERAGE FL, LLC (813-534-6326)

Listing Agent: James Wible (813-440-0477)

Remarks: PRICE IMPROVEMENT & HOME WARRANTY INCLUDED! Now offered at an even better value, this beautifully maintained home in Brookhaven’s desirable 55+ community is the perfect opportunity to enjoy comfortable Florida living with owned land and low HOA fees. Located on a corner lot on a quiet dead-end street, this 2005 Homes of Merit double-wide manufactured home offers 1,440 sq. ft. of well-designed living space and comes fully furnished and move-in ready. The spacious open floor plan features 3 bedrooms, 2 bathrooms, an indoor laundry room, and abundant natural light throughout. Elegant tray ceilings enhance the main living area, while sliding glass doors lead to an additional porch overlooking a peaceful neighboring pasture—an ideal place to relax and enjoy the view. The large kitchen is designed for both functionality and entertaining, featuring a center island, ample cabinet and counter space, updated microwave, newer refrigerator (2024), and A/C unit (2024). Recent improvements provide added value and peace of mind, including a new shingle roof and carport (2023), updated siding, reinforced tie-downs, fresh interior paint, and new Parkay Endurance water-resistant laminate flooring. A versatile bonus room with French doors offers flexibility for a home office, hobby room, or third bedroom. The guest bedroom and bath are generously sized, while the oversized primary suite includes a private ensuite bathroom for added comfort and privacy. Additional features include an indoor laundry room with washer and dryer included, a spacious workshop/storage area, and valuable extras such as an 8,000-watt generator (gas or propane) with two propane tanks, mower, trimmer, and power washer. Surrounded by mature landscaping, this property offers both charm and tranquility. Brookhaven residents enjoy amenities including a community pool, clubhouse, and shuffleboard, all with a low HOA fee of just $34 monthly. Conveniently located near Hwy 27, shopping, restaurants, and medical facilities, this home is also approximately one hour from Disney and within easy driving distance to both Florida coasts. Don’t miss your opportunity to own this well-maintained, fully furnished home with owned land in one of Central Florida’s welcoming 55+ communities. Schedule your private showing today.

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

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

Remarks: Under Construction. Under Construction. Welcome to the Residences at Winter Haven, a new single-family community designed for those who value both quality and connection. This Key West model floor plan features a functional 4-bedroom, open-concept layout centered around a kitchen with a full waterfall countertop island. The home includes a covered lanai for outdoor living, a dedicated laundry room, and a smart home package.The estimated completion date is at the end of June.

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

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

Remarks: Under Construction. Under Construction. Welcome to the Residences at Winter Haven, a new single-family community designed for those who value both quality and connection. The Key West floor plan offers a functional, open-concept design that prioritizes modern convenience and high-end finishes. The layout includes a dedicated formal dining room and a kitchen anchored by a full waterfall countertop island. This 3-bedroom, 2-bathroom residence is equipped with a smart home package and a dedicated laundry room. The estimated completion date is at the end of June.

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

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

Remarks: Move-in Ready! Welcome to the Residences at Winter Haven, a premier new single-family community designed for those who value both quality and connection. Set within this inviting neighborhood, the Crystal River Gen Suite floor plan brings a versatile elegance to everyday living. The open layout is anchored by a stunning gourmet kitchen featuring a waterfall island, while a private Gen Suite offers ultimate flexibility and independence with its own entrance, bath, and kitchenette. It’s a lovely modern space that’s ready for you to make it your own.

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

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

Remarks: Move-in ready! Welcome to the Residences at Winter Haven, a premier new single-family community designed for those who value both quality and connection. Set within this inviting neighborhood, the Everglades floor plan brings a natural ease to everyday living, from its open layout to the thoughtful finishes. At the heart of the home is a stunning kitchen featuring a large waterfall island and 42” cabinetry. Designed for hosting, the living area flows effortlessly out to a covered lanai. It’s a clean, modern space ready for you to make your own.

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

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

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)