Homes for Sale Near Westwood Middle in Winter Haven - 97 homes

Remarks: This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.

Listing is courtesy of: THE URBAN GROUP, INC. (954-522-6226)

Listing Agent: Ashlee Morrell (941-740-9134)

Remarks: 2 Lots and 2 Homes for the price of One. Attention investors and those looking for a great deal! Seize a truly unique opportunity to own two homes for the price of one. This property includes a single-family home with 2 bedrooms and 1 bathroom address 215 10th Wahneta St W Winter Haven FL, as well as a single-wide mobile home from 1988 with 2 bedrooms and 1 bathroom address 213 10th Wahneta St W Winter Haven FL 33880. The single-family & Mobile home needs Lot's TLC but has great potential. It could be perfect for someone willing to put in some work or an investor looking to flip or rent it out. Also included on the property is a detached garage offering an extra 480 square feet of storage space. This unique setup offers flexibility depending on your needs. This is truly a rare find at this price point. Don't miss out on this fantastic investment opportunity! Dual Rental Income, Fix-and-Flip Potential, Multi-Generational Living

Listing is courtesy of: J&T PROPERTY SOLUTIONS GROUP LLC (863-440-3603)

Listing Agent: Jennifer Daniell (863-440-3603)

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 check out this like-new 4-bedroom, 2-bathroom home with unbeatable value, priced to sell under $300k! If that's not enough, this newer community has absolutely NO CDD fees and a very low HOA, making this a great starter or investment home. Get instant equity on day one! Watch gorgeous sunsets over the water right from your private, covered lanai, and fully Fenced back yard with a high-quality, durable metal fence. Inside, this meticulously maintained home features the highly sought-after open-concept Valeria floor plan, complete with a spacious 2-car garage, contemporary kitchen finishes, sleek solid-surface quartz countertops, and included appliances. The large primary suite is tucked away for ultimate quiet, featuring an oversized walk-in closet and a dual-vanity bath. Located in a pristine, quiet community just minutes from Legoland, top schools, and major roadways. Turn-key, and priced for an immediate sale—schedule your private tour today.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Richard Rung (727-272-0267)

Remarks: Welcome to your perfect slice of Florida living! This solid concrete block home combines durability, comfort, and modern updates - making it an exceptional opportunity whether you're searching for your next residence or an investment property. Step inside to discover brand-new vinyl plank flooring that flows beautifully throughout, complemented by newer stainless steel appliances that bring a fresh, modern feel to the home. Major systems have already been taken care of for you, including a 2022 HVAC system and 2022 water heater, plus a metal roof installed in 2012 for long-term peace of mind. Outside, enjoy a fully fenced yard - perfect for pets, entertaining, or simply relaxing under the canopy of mature shade trees. The carport and additional parking pad provide plenty of space for vehicles, guests, or even a boat. Nestled in an established neighborhood, this home offers the rare advantage of NO HOA or CDD fees, giving you both freedom and affordability. You'll love the convenient location - just minutes from lakes, parks, shopping, and vibrant downtown Winter Haven. Whether you're looking to settle in or invest, this property checks all the boxes. Don't miss your chance to own this move-in-ready gem - schedule your private showing today before it's gone!

Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)

Listing Agent: John Evans (813-992-3483)

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

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

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

Remarks: Step inside this well-designed single-family home offering comfort, functionality, and a layout that truly makes sense. You’re welcomed by a screened front porch and a beautifully landscaped front yard, setting the tone before you even walk through the door. Inside, you’ll find engineered wood flooring throughout the main living areas with ceramic tile in both bathrooms. The living and dining rooms flow together in one open space, creating an easy layout for everyday living or entertaining. At the heart of the home sits the open kitchen, featuring granite countertops and a central location that keeps you connected to everything happening in the home. The split bedroom floorplan provides privacy, and the spacious primary suite includes a garden tub for unwinding at the end of the day. Enjoy added convenience with an inside laundry room located just off the kitchen as you enter from the two-car garage. The backyard has been thoughtfully designed with low-maintenance rock landscaping instead of grass and is framed by a vinyl privacy fence along both sides and across the back. Additional highlights include high ceilings, approximately 1,716 heated square feet, and about 2,400 square feet under roof—giving you plenty of room to spread out. A comfortable, well-kept home with smart updates and a layout that works for today’s lifestyle—this one is ready for its next chapter.

Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)

Listing Agent: Julie Sutphin (407-414-4024)

Remarks: ***PRICE DECREASE*** This unique 2-story home in Winter Haven is full of character and charm, located just three houses down from scenic Lake Elbert. Thoughtfully updated while preserving its warm, rustic appeal, this property offers a welcoming atmosphere from the moment you arrive. Outdoor enthusiasts will love the 2.4-mile paved loop trail surrounding Lake Elbert, complete with boardwalks and beautiful landscaping—perfect for morning walks, bike rides, or peaceful evening strolls. The home is in walking distance to Downtown Winter Haven, the public boat ramp and park, and Polk State College’s Winter Haven Fine Arts Building, offering exceptional convenience and lifestyle amenities. Inside, you’ll find live-edge wood countertops, natural wood trim, and an open kitchen overlooking the family and dining rooms. The kitchen features stainless steel appliances, newer cabinets, and a rustic flair originally crafted by an Amish family. The spacious family room includes a large picture windows that frame the beautiful front yard and mature oak tree. The primary bedroom and bathroom are conveniently located downstairs, while the second floor offers two additional bedrooms, a bonus room, a full bathroom, and a loft area with generous storage closets. Both bathrooms have been updated with newer cabinets, newer countertops, and newer tile. Additional interior upgrades include newer luxury vinyl plank flooring, newer windows, newer light fixtures and ceiling fans, and fresh interior paint. The home also features a newer A/C system. Outside, the home offers a covered front porch perfect for evening relaxation, mature landscaping, and a fenced yard on nearly a quarter-acre, with most of the outdoor space located in the front of the home. Ideally situated near Lake Elbert, Downtown Winter Haven, Polk State College, shopping, dining, parks, and medical facilities, this home offers both convenience and character. Schedule your private showing today!

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

Listing Agent: Lisa Ford (863-510-3890)

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: Welcome home! Located in the heart of Winter Haven, this BEAUTIFULLY RENOVATED POOL HOME offers the perfect blend of comfort, style, and outdoor living at an incredible value. Featuring 3 spacious bedrooms and 2 bathrooms, this move in ready home was thoughtfully designed for both everyday living and entertaining .Step inside and immediately fall in love with the STUNNING FULLY RENOVATED MODERN KITCHEN featuring newer stainless appliances, all-new cabinetry, gorgeous granite countertops, and a custom coffee bar perfect for your morning routine. The OPEN CONCEPT FLOORPLAN creates a bright and inviting atmosphere with seamless flow between the kitchen, dining, and living spaces, making this home ideal for hosting family and friends. Additional interior upgrades include NEW TILE FLOORING THROUGHOUT, fresh interior paint, and beautifully remodeled bathrooms complete with updated vanities and toilets. Every detail has been thoughtfully updated to provide a clean, modern, and stylish feel throughout the entire residence. Outside, your PRIVATE BACKYARD OASIS awaits! The stunning pool and spa, installed in 2025, features all equipment still under warranty, creating a worry free opportunity for the next owner. Enjoy relaxing or entertaining year-round on the EXTRA LARGE SCREENED IN LANAI featuring new double insulated roof panels, three oversized ceiling fans, installed power access, and a mounted TV bracket ready for game days or outdoor movie nights. The FULLY FENCED BACKYARD with privacy fencing provides the perfect space for pets, family gatherings, or simply relaxing in peace and tranquility. Located in a quiet and desirable community with a LOW ANNUAL HOA, this home truly checks all the boxes whether you are looking for your first home, a vacation retreat, or the perfect place to entertain. Schedule your private showing today!

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

Listing Agent: Eli Medina (863-797-5183)

Remarks: Discover this unique Spanish/Mediterranean-inspired estate on an oversized lot across from Lake Jessie on the Chain of Lakes. Featuring a 3BR/2BA main home plus a private 1BR/2BA casita/in-law suite, this property is ideal for multi-generational living, vacation rentals, or income-producing opportunities. The versatile floor plan provides the flexibility to function as a triplex-style investment property. Recent upgrades include a NEW roof, NEW AC, NEW water heater, new casita flooring, and more. Inside, enjoy vaulted ceilings, a fireplace, abundant natural light, and spacious living areas designed for entertaining. Step outside to a resort-style screened saltwater heated pool with new heating, cooling, and saltwater systems. Located on a quiet street with no rear neighbors and NO HOA, there’s plenty of room for boats, RVs, and extra vehicles—just steps from the community boat ramp on Lake Jessie. A rare blend of privacy, flexibility, and investment potential. Don't miss this opportunity! Book your appointment today.

Listing is courtesy of: META ONE REALTY GROUP LLC (407-223-3678)

Listing Agent: Aline Oliveira (407-300-7123)

Remarks: Under contract-accepting backup offers. 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: Under contract-accepting backup offers. 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 3006 Elm Street in beautiful Winter Haven — a charming home full of potential and perfectly positioned for convenience! This 3-bedroom, 1.5-bath home also features a flexible office space that could easily serve as a 4th bedroom, playroom, hobby room, or home gym. Step inside to find new tile flooring, a remodeled bathroom, a newer roof, and updated ceilings that give the home a fresh and modern feel. The spacious kitchen offers plenty of room to cook, gather, and get creative with your dream design ideas. Outside, the backyard is a blank canvas ready for your personal touch — create the garden, outdoor kitchen, pool area, or entertaining space you've always wanted! Conveniently located near shopping, dining, attractions, and with easy access for commuting to both Tampa and Orlando, this property offers the perfect blend of comfort, opportunity, and location. Whether you're looking for your first home, investment property, or extra space to grow, this Winter Haven gem is ready to welcome you home!

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

Listing Agent: Michele Elchin (863-514-6880)

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: Welcome to this beautifully upgraded 2024 Richmond American Ruby model in sought-after Sutton Preserve! This 4-bedroom, 2-bath home offers nearly 1,900 sq ft of open-concept living with quartz countertops, solid wood cabinetry, tile flooring throughout the main areas, and carpet in the bedrooms. The spacious kitchen features a large island, pantry, and stainless steel appliances, flowing seamlessly into the living and dining spaces. Enjoy premium upgrades including epoxy garage floors, rain gutters, security cameras that convey, and assumable leased solar panels with a transferable 25-year warranty, offering energy efficiency and average electric bills under $20/month. Relax year-round in the enclosed screened patio with added shades and a fully fenced backyard for privacy. Conveniently located near shopping, dining, schools, and major roadways with low HOA and no CDD—this move-in ready home is a must-see!

Listing is courtesy of: HOMESMART (407-476-0451)

Listing Agent: Nan Seelall Llc (352-978-1050)