Winter Garden Real Estate

Homes for Sale in Winter Garden, FL Between $400,000 to $500,000

Welcome to your dedicated resource for Homes for Sale Between $400,000 to $500,000 in Winter Garden, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Winter Garden, FL agents, Zen Home Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $400,000 to $500,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Winter Garden, FL Homes for Sale Between $400,000 to $500,000

5522 New Independence Parkway, Winter Garden
$499,900
3 Beds ⋅ 2 Baths ⋅ Signature Lakes, Independence SubDv. ⋅ 34787 Zip Code
Independence ** Rare floor plan for Independence with 3 bedrooms and +/-17x12' DEN or living room space ** FRESHLY painted neutral soft white interior and BRAND NEW LAMINATE FLOORING in the 3 bedrooms ** 19x10' Florida Room with AC and heat ** Primary bedroom has 2 walk in closets with built in white shelving & ensuite primary bath with two sinks, granite counters, garden tub and separate shower ** The kitchen has a large cooking island with granite counters and includes the stainless steel stove, refrig and dishwasher ** Laundry room with built in white shelving and washer and dryer included ** Ceiling fans in every room ** Great completely fenced back yard with Florida room and brick paver patio area 2018 ** 2 car attached garage ** Lovely front porch with brick patio pavers ** Beautiful Florida Room Other upgrades include: NEW Trane A/C SYSTEM 10/2025, NEW white vinyl fence and gates 2/2024, NEW exterior brass whole house water shutoff valve 3/2026, NEW garage door system, SPRINGS 2/2021 and garage door opener 10/2024 ** LOW HOA fees $194.69 incl cable & internet which currently includes HBO and Max! Incredible amenities including 2 community pools, play areas, a lg community park plus other neighborhood green space and play areas thru-out the neighborhood, loads of sidewalks & conservation thru-out... All room measurements are approximate from the Builder floor plan. Buyer to verify measurements. Square footage is from Orange County Appraiser records ** Refrigerator ice maker is not working **

5522 New Independence Parkway, Winter Garden
17138 Arrowhead Boulevard, Winter Garden
$499,900
2 Beds ⋅ 2 Baths ⋅ Arrowhead Lakes SubDv. ⋅ 34787 Zip Code
Prime location! Spring fed lakefront charm. Well-built and maintained 2 bedrooms, 2 baths home high and dry. Nice layout inside out with private pond and lake access. Outdoor pet enclosure for your furry friends. The enclosed metal garage can protect all your toys. Mature landscaping. Established neighborhood. Tons of natural life with fishing opportunities. 11 minutes to Disney World. 14 minutes to Orange County National Golf Center and Lodge. Close proximity to all major amusement parks. A2 zoning, A schools and No HOA.

17138 Arrowhead Boulevard, Winter Garden
1396 Roxy Lane, Winter Garden
$499,900
4 Beds ⋅ 3 Baths ⋅ Waterside/Johns Lake Ph 2c SubDv. ⋅ 34787 Zip Code
Welcome home to Waterside on Johns Lake, a highly sought-after community in Winter Garden! This 4-bedroom, 3-full-bath, 2,030 sq. ft. single-family home offers an open-concept floor plan with a great blend of functionality and living space. The first floor features the great room that flows seamlessly into the dining area and kitchen, which features 42-inch grey shaker cabinetry, quartz countertops, and a pantry. Also on the first floor is a full bathroom and a bedroom, making it ideal for guests, a home office, or flexible living needs. A convenient mudroom with generous storage provides additional functionality. Step outside to a private patio with a dedicated seating and entertaining area, along with a large fenced-in side yard. The rear of the property features a detached 2-car garage and a private driveway with additional parking for two vehicles. Upstairs, the split-bedroom layout provides privacy and flexibility. The spacious primary suite features an oversized bedroom, walk-in closet, and private en-suite bathroom. Two additional bedrooms, a third full bathroom, and a dedicated laundry room complete the second floor. The location is hard to beat, with convenient access to Winter Garden Village, Hamlin, Horizon West, Downtown Winter Garden, and SR-429. Enjoy an easy drive to Central Florida's major attractions, including Disney, SeaWorld, and Universal Studios, as well as an abundance of shopping, dining, and entertainment options. Waterside on Johns Lake features resort-style amenities including a community pool and clubhouse, playground, park, fitness center, and community dock on Johns Lake. The home is also zoned for highly regarded A-rated schools, including Hamlin Elementary, Hamlin Middle, and West Orange High.

1396 Roxy Lane, Winter Garden
11030 Folklore Street, Winter Garden
$499,900
3 Beds ⋅ 3 Baths ⋅ Storey Grove Ph 1b 1 SubDv. ⋅ 34787 Zip Code
Welcome to 11030 Folklore Street in Storey Grove, where everyday living comes with more to enjoy! This twoStorey Winter Garden home offers 3 bedrooms, 2.5 bathrooms, and a detached garage. Enjoy the neighborhood's pool, clubhouse, fitness center, playground and walking paths. Located near Avalon Road in Horizon West, the home offers convenient access to SR-429, Hamlin Town Center, Flamingo Crossings, Walt Disney World, and Winter Garden shopping and dining. Come explore the home and the community for yourself!

11030 Folklore Street, Winter Garden
13953 Easdale Alley, Winter Garden
$499,900
3 Beds ⋅ 3 Baths ⋅ Westhaven/Ovation SubDv. ⋅ 34787 Zip Code
BACK ON THE MARKET WITH A PRICE IMPROVEMENT! Don’t miss this highly upgraded Toll Brothers townhome in Westhaven at Ovation. Built in 2024, this popular floor plan that is NO LONGER AVAILABLE FROM THE BUILDER. The open-concept main level features a beautifully upgraded kitchen with quartz countertops, designer cabinetry and backsplash, stainless steel appliances, and an oversized island. Step outside to your private courtyard featuring a hot tub that can come along—perfect for relaxing and enjoying the Florida lifestyle. Additional upgrades include upgraded finishes throughout. Upstairs, the spacious primary suite offers a walk-in closet and upgraded en-suite bath, plus two additional bedrooms. Located approximately 2 MINUTES FROM THE NEARBY ELEMENTARY SCHOOL and close to Horizon West, Hamlin, shopping, dining, entertainment, and major roadways. Multiple upgrades, included spa, prime Winter Garden location, and a floor plan you can no longer purchase from the builder!

13953 Easdale Alley, Winter Garden
14075 Lochend Way, Winter Garden
$499,900
4 Beds ⋅ 3 Baths ⋅ Westhaven/Ovation SubDv. ⋅ 34787 Zip Code
Almost New & Move-In Ready! Built in 2024, this beautifully maintained corner-unit townhome offers the perfect combination of modern style, comfort, and functionality. Featuring 4 full bedrooms and 3 full bathrooms, the thoughtfully designed floor plan includes a convenient first-floor bedroom, ideal for a home office, guest suite, or private bedroom. The home showcases upgraded tile flooring throughout the main living areas and stylish granite countertops, creating a clean and contemporary feel. The spacious kitchen comes fully equipped with stainless steel appliances, including refrigerator, microwave, and dishwasher, plus a washer and dryer for added convenience. Enjoy Florida living from the screened-in back porch, perfect for relaxing or entertaining while enjoying the outdoors. A private 2-car garage located at the rear of the home provides secure parking and additional storage. Residents enjoy an impressive selection of community amenities, including a resort-style pool, fitness center, gathering area, playground, and community mailbox. With its desirable corner-unit location, modern finishes, flexible first-floor bedroom, and excellent amenities, this almost-new townhome is an exceptional opportunity for both homeowners and investors. Come see why this beautiful 2024 townhome is the perfect place to call home!

14075 Lochend Way, Winter Garden
14099 Frasier Street, Winter Garden
$499,900
3 Beds ⋅ 3 Baths ⋅ Highland Rdg Ph 2 SubDv. ⋅ 34787 Zip Code
*Price reduction* ready to sell! Welcome to this bright and inviting 3 BEDROOMS, 2 and 1/2 Bathrooms home in the Highland Ridge community of Winter Garden. It feels open and comfortable the moment you walk in. The beautiful CERAMIC TILE throughout the first floor already gives the perspective of the open floor plan. Right off the entry is a flexible room currently used as a HOME OFFICE — a great spot for work or study that connect to the kitchen. The HIGH CEILINGS in the DINNING ROOM AREA makes the space feel bigger and brighter, and it's by the LIVING ROOM AND GOURMET KITCHEN. The kitchen is a real highlight, with WHITE CABINETS, a LARGE ISLAND COUNTER for cooking, COOKTOP STOVE other stainless steel appliances, and those nice geometric pendant lights. Sliding glass doors open out to the backyard, so the whole main floor feels connected to the outdoors. With EXTENDED PAVER AND FENCED in the back, turning the outdoor space into a finished patio area that’s ready for grilling and relaxing and plus a covered area that goes to the 2 CAR GARAGE DETACHED. Upstairs you’ll find a SPACIOUS primary suite bedroom, plus two more comfortable bedrooms, LAUNDRY ROOM and LOFT . Everything feels clean, light, and MOVE IN READY. Highland Ridge has some really nice amenities right in the neighborhood: a pool with a cabana, playground, basketball court, and pickleball. It’s the kind of place where families can unwind without getting in the car. The location is convenient too. You’re just minutes from Disney World and Flamingo Crossings for shopping and restaurants, with easy access to the 429. Nearby schools include Water Spring Elementary and Middle, and Horizon High. Downtown Winter Garden, with its farmers market and Plant Street shops, is a short drive away. This home offers a good mix of modern comfort, useful living spaces, and a friendly community feel. If you’re looking for something that already feels like home, this one is worth seeing.

14099 Frasier Street, Winter Garden
15101 Purple Martin Street, Winter Garden
$499,900
3 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 3b SubDv. ⋅ 34787 Zip Code
Virtually Staged. *** SUMMERLAKE WINTER GAREN/HORIZON WEST MOVE-IN READY HOME * PERFECT LOCATION * TOP GRADE SCHOOLS * HOA INCLUDES LAWNCARE AND RESORT-STYLE AMENITIES *** Welcome to this well-maintained, move-in-ready two-story home in the sought-after Summerlake community of Horizon West at Winter Garden. Low-maintenance living with HOA-included lawn care. Beautiful home featuring living space with 3 bedrooms, 2.5 bathrooms, 1 versatile main-level den/office/flex room, 2-car garage and covered patio. A-rated school zone. The functional open floor plan features a modern kitchen that flows into the dining and living areas. Downstairs main-level den/office is ideal for remote work, guests, or a home gym. Upstairs spacious primary suite with en-suite bath. Two additional bedrooms upstairs. Covered patio. Summerlake is an amazing Resort-Style Lifestyle community amenities including a resort-style pool with splash pad, clubhouse with lake views, state-of-the-art fitness center, tennis & basketball courts, zipline, dog park, playgrounds, sports fields, walking trails, and more. Conveniently located in the heart of Horizon West, minutes from Orange County National Golf Center, Hamlin Town Center (shopping, dining, cinema), Winter Garden Village, major highways (SR 429, 535, US 192), Walt Disney World, and Universal Orlando. Schedule a showing today!

15101 Purple Martin Street, Winter Garden
12792 Sunset Walk Drive, Winter Garden
$499,000
4 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to the Autumn Elite Farmhouse by Toll Brothers in Westhaven at Ovation. This new construction townhome offers 4 bedrooms, 3 bathrooms, and 1,930 square feet of thoughtfully designed living space with an open-concept layout ideal for everyday living and entertaining. As a Design Studio Ready home, buyers can personalize finishes and selections to match their style. Conveniently located in Winter Garden, just 15 minutes from Walt Disney World, with easy access to shopping, dining, and major roadways. Don't miss this opportunity to own a new Toll Brothers home in one of Central Florida's most desirable communities.

12792 Sunset Walk Drive, Winter Garden
12253 S Bracco Street, Winter Garden
$499,000
3 Beds ⋅ 3 Baths ⋅ Highland Rdg Ph 2 SubDv. ⋅ 34787 Zip Code
BRAND NEW CONSTRUCTION – NEVER LIVED IN – MOVE-IN READY! This is a rare opportunity to own a truly brand-new home that has never been occupied since the day it closed. No previous residents, no wear and tear, no surprises. Just a fresh start in a home that feels exactly as the builder intended. Be the very first person to live here, create memories here, and even peel the protective plastic off the brand-new appliances! Located in the highly sought-after Highland Ridge community, this stunning energy-efficient home offers a spacious open-concept design perfect for today's lifestyle. The beautifully appointed kitchen features a large center island that flows seamlessly into the dining and living areas, creating the ideal space for entertaining and everyday living. Upstairs, a versatile loft provides endless possibilities: home office, media room, game room, fitness area, or additional family space. Built by Meritage Homes in 2024, this home showcases advanced energy-efficient construction designed to provide year-round comfort, healthier indoor air quality, and lower utility costs. Ideally located in the heart of Winter Garden, you'll enjoy convenient access to top-rated schools, shopping, dining, major employment centers, and world-famous Disney attractions just minutes away. Why wait months for new construction when you can move into a never-lived-in home today? Schedule your private tour and experience what "brand new" truly means!

12253 S Bracco Street, Winter Garden
9354 Meadow Hunt Way, Winter Garden
$499,000
3 Beds ⋅ 3 Baths ⋅ Watermark SubDv. ⋅ 34787 Zip Code
MOVE-IN READY, ENERGY-EFFICIENT HOME WITH TILE ROOF, SOLAR, AND 4TH BEDROOM POTENTIAL IN WATERMARK! Located in one of Horizon West’s most desirable resort-style communities, this beautifully maintained, original-owner home offers over 2,000 square feet of thoughtfully designed living space, designer upgrades, and standout curb appeal with a MEDITERRANEAN-STYLE TILE ROOF. Built to last decades longer than a standard shingle roof, the tile roof offers long-term peace of mind. A 9-PANEL SOLAR SYSTEM adds to the home’s efficiency, helping to REDUCE MONTHLY UTILITY COSTS year after year. Inside, a spacious upstairs BONUS LOFT offers the potential to be converted into a 4TH BEDROOM. Currently configured with 3 bedrooms and 2.5 baths, the versatile loft can also serve as a home office, media room, playroom, or additional living area. The bright, open-concept floor plan is ideal for everyday living and entertaining, featuring a gourmet kitchen with DOUBLE OVENS, cooktop, designer backsplash, under-cabinet lighting, upgraded cabinetry, and an oversized island overlooking the dining and living areas. Interior upgrades include WOOD FLOORING in the main living areas, oak tread stairs with wood spindles, upgraded baseboards, eight-foot first-floor doors, and DOUBLE FRENCH DOORS opening to a covered lanai. The spacious PRIMARY SUITE features a tray ceiling, TWO WALK-IN CLOSETS, and a spa-inspired bath with dual vanities, extended countertop, walk-in shower with DUAL SHOWER HEADS, linen closet, and private water closet. Both secondary bedrooms also feature walk-in closets, providing exceptional storage. Built with efficiency in mind from the roof down, the home combines its SOLAR SYSTEM with SPRAY FOAM INSULATION and DOUBLE-PANE WINDOWS, a package designed to keep energy bills low and comfort high in the Florida climate. Enjoy WATERMARK’S RESORT-STYLE AMENITIES, including two community pools, a splash pad with water slides, fitness center, clubhouse, tennis and basketball courts, community events, food truck nights, and a rooftop observation deck with views of Disney’s nightly fireworks. Conveniently located near HAMLIN TOWN CENTER, Walt Disney World, shopping, dining, parks, trails, and major highways. Zoned for A-rated schools. Discover the flexibility, upgrades, savings, and lifestyle this exceptional Watermark home offers.

9354 Meadow Hunt Way, Winter Garden
14280 Braemar Street, Winter Garden
$499,000
3 Beds ⋅ 3 Baths ⋅ Highland Rdg SubDv. ⋅ 34787 Zip Code
PRICE IMPROVEMENT – NOW OFFERED AT $499,000! Exceptional opportunity to own a nearly new home in the highly sought-after Highland Ridge community of Winter Garden. Built in 2023, this beautifully maintained 3-bedroom, 2.5-bath residence offers a modern open-concept floor plan with stylish finishes throughout. The spacious kitchen features granite countertops, stainless steel appliances, ample cabinet space, and opens seamlessly to the living and dining areas, making it ideal for everyday living and entertaining. Upstairs, you’ll find a generous primary suite, two additional bedrooms, and a versatile loft space. At just $499,000, this home presents one of the best values in Winter Garden for a newer construction property. Conveniently located near Downtown Winter Garden, Hamlin Town Center, shopping, dining, entertainment, major highways, and top-rated schools. Community amenities include a playground, pool, and beautifully maintained common areas. Move-in ready and priced to sell—schedule your private showing today before this opportunity is gone!

14280 Braemar Street, Winter Garden
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