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

Remarks: Short Sale. Great opportunity to own this spacious home! Please note this is a short sale and purchase is subject to lender/bank approval. Property is being sold strictly in As-Is condition, and buyer is responsible for all municipal inspections. Bring your vision and custom touches to make this home your own! Opportunity meets value in this 3-bedroom, 2-bath home located in a well-established Winter Haven neighborhood. NO HOA. Positioned on a spacious, fully fenced corner lot, this property offers exceptional outdoor space and includes an above-ground pool, perfect for cooling off on hot Florida days, entertaining guests, or enjoying your own private backyard retreat. Inside, you’ll find a functional, comfortable layout with great natural light and flexible living space. This home presents an excellent opportunity for buyers looking to add personal style, build equity, or secure a solid investment property in a growing area. Whether you’re a first-time buyer, downsizing, or expanding your investment portfolio, this home offers strong potential, location convenience, and everyday livability. Ideally located near shopping, dining, Downtown Winter Haven, and the Polk Parkway, with easy access to both Orlando and Tampa for commuting or weekend travel. If you’re looking for space, flexibility, and long-term value with NO HOA restrictions, this is one you don’t want to miss. Schedule your private showing today and explore the possibilities.

Listing is courtesy of: SIGNATURE INTERNATIONAL REAL E (561-404-7263)

Listing Agent: Barbi Rodriguez, Llc (352-404-2377)

Remarks: Filled with potential and flexibility, this home is perfect for buyers looking to add their own style and create value. "A great opportunity for buyers or investors to customize and build equity. The layout includes 4 bedrooms, 2 full bathrooms, a living room, kitchen, den, And a laundry room. Ideal for a family with a growing household. This home offers 1,437 sq ft of living space on a 7,148 sq ft lot, with a new roof installed in 2023 and HVAC updated in 2022. Make this home yours today!

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

Listing Agent: Mikisha Joseph (813-810-8576)

Remarks: Virtually Staged. Welcome to this beautiful home in peace creek reserve! this thoughtfully designed single-story residence offers 4 bedrooms and 2.5 bathrooms, combining comfort and functionality. The open-concept floor plan seamlessly connects the family room, dining area, and kitchen—complete with a central island—creating the perfect space for everyday living and entertaining. Located in the desirable peace creek reserve community, residents enjoy a serene setting surrounded by nature, including a picturesque creek. situated in winter haven—known as the chain of lakes city with over 26 connected lakes—this area offers a variety of shopping, dining, and outdoor activities such as biking and water recreation. Peace creek reserve provides the perfect balance of a peaceful, small-town atmosphere with everyday convenience—an ideal place to call home.

Listing is courtesy of: GLASSTONE GROUP INC (321-988-4663)

Listing Agent: Barbara Cunha De Freitas (617-458-0838)

Remarks: Welcome home to this beautifully updated 3-bedroom, 2-bath single-family pool home offering 1,860 square feet of living space with NO HOA! This well-maintained property features a desirable floor plan with formal living and dining rooms, family room with cathedral ceiling and 2 car garage with opener. The spacious kitchen has tons of counter space and is equipped with a center island, quartz countertops, newer cabinetry, and matching Whirlpool stainless steel appliances. Just off the kitchen, you'll find a convenient inside laundry closet with washer and dryer hookups. The large family room features a cozy fireplace and ceiling fan while overlooking the screened pool lanai. The primary bedroom offers a private retreat with an en-suite bath, step-in closet, and sliding glass doors providing direct access to the pool lanai. Recent updates include newer luxury vinyl flooring throughout, recessed lighting, renovated bathrooms and a 2019 roof & A/C system. Step outside to enjoy the screened lanai with a large in-ground pool and a nice-sized partially fenced backyard, providing plenty of space for relaxation and outdoor activities. Conveniently located near the Polk Parkway with easy access to I-4, this home is just a short drive from Legoland, Orlando theme parks, shopping, dining, and a variety of recreational amenities. Don't miss this opportunity to own a move-in ready pool home in a prime Central Florida location!

Listing is courtesy of: VIEWPOINT VALUE REALTY (863-617-7015)

Listing Agent: Pat Pearson (908-295-7970)

Remarks: Welcome to this exceptional custom-built 2023 luxury residence located within the gated community of Sanctuary by the Lake, where modern elegance, thoughtful design, & everyday comfort come together seamlessly. Perfectly positioned on a spacious corner lot directly across from the lake, this stunning home immediately impresses with its commanding presence & refined architectural detail. Step through the beautiful double front doors & experience an immediate sense of openness, highlighted by soaring ceilings, abundant natural light, & expansive living spaces designed to feel both grand & inviting. With over 3,600 square feet of living space, the thoughtfully designed open layout effortlessly connects formal & casual living areas, creating an ideal setting for both entertaining & relaxed daily living. At the heart of the home lies a beautifully appointed chef’s kitchen, featuring granite countertops, upgraded Stainless Steel appliances, a breakfast bar, walk-in pantry, and generous prep space, perfect for hosting gatherings or enjoying quiet mornings at home. The kitchen flows naturally into the impressive great room and dining areas, enhancing the home’s seamless indoor living experience. One of the standout features is the oversized covered and enclosed Florida room, custom added by the owners to extend the living space year-round. Whether hosting celebrations, entertaining guests, or simply unwinding while enjoying peaceful surroundings, this space truly elevates the lifestyle this home offers. Designed with privacy in mind, the desirable triple split floor plan includes 4 spacious bedrooms, 3 full bathrooms, and a dedicated private office, ideal for remote work or flexible living needs. The luxurious primary suite serves as a private retreat, complete with dual vanities, a garden tub, separate walk-in shower, makeup vanity, and a very generous walk-in closet. Beautiful luxury vinyl plank flooring flows throughout the main living areas, complemented by tasteful finishes and quality craftsmanship that reflect the home’s custom construction. A well-equipped laundry room with cabinetry, countertop workspace, and sink adds everyday convenience. A 50 amp generator port was added for peace of mind. Beyond the home itself, the location offers the best of Central Florida living. Just minutes from downtown Winter Haven, residents enjoy award-winning restaurants, local boutiques, parks, and year-round entertainment, while nearby access to Lakeland & I-4 provides an easy commute to both Tampa and Orlando. Florida’s Atlantic and Gulf beaches are approximately 90 minutes away, making weekend coastal escapes effortlessly accessible. This is more than a home, it is a refined living experience combining space, luxury, and lifestyle within one of Winter Haven’s most desirable gated communities.

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

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

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: Winter Haven home near Chain of Lakes featuring 5 bedrooms, 3 bathrooms, and 2 flexible bonus rooms offering exceptional convenience and a lifestyle close to everything Central Florida buyers love. This move in ready property provides effortless access to major commuter routes, grocery stores, shopping, dining, scenic walking trails, LEGOLAND Florida Resort, and Florida’s beautiful beaches just about 90 minutes away. Step into your own private outdoor sanctuary designed for both relaxation and entertainment. The caged saltwater pool includes a 6×10 sun shelf perfect for in water lounging along with a 3 to 6 foot depth range ideal for both play and leisurely floating. Enjoy the luxury of a heated spa with priority Jacuzzi jet action creating the perfect setting for evening unwinding, stress relief, muscle relaxation, or hosting friends for cozy nights under the stars. The spacious gazebo offers a shaded retreat for outdoor dining, socializing, or simply enjoying the Florida breeze. Practical upgrades elevate this property as it is equipped to support a home generator, has a warrantied water softener for supreme taste, two 5-ft gates that create a wide 10-ft entry to the backyard and a on-site shed adding valuable extra storage keeping everything tidy and easy to access. Inside, the home feels bright, modern, and truly move in ready. The open concept layout creates an inviting flow throughout, and the generous kitchen is perfectly suited for gatherings, meal prep, and everyday connection. With its flexible floor plan, this home easily accommodates large families, multi generational living, or hosting guests with comfort and privacy. A standout property offering both lifestyle and practicality. This home is a must see!

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

Listing Agent: Andrea Friedmann (863-661-6535)

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: 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: 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: 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: 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: 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)