Explore Winter Garden, FL Homes for Sale Between $550,000 to $600,000

Winter Garden, FL Homes for Sale Between $550,000 to $600,000 Map Search

Homes for Sale in Winter Garden, FL Between $550,000 to $600,000

Welcome to your dedicated resource for Homes for Sale Between $550,000 to $600,000 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 a local Winter Garden, FL agent, The Nest 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 $550,000 to $600,000 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 $550,000 to $600,000

$595,000
4 Beds ⋅ 3 Baths ⋅ Cambridge Crossing Ph 1a SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to 12525 Scarlett Sage Ct, a beautifully renovated home in Winter Garden’s gated Cambridge Crossing community. With four bedrooms, three full bathrooms, and approximately 2,529 square feet of single-story living space, this home offers generous rooms and distinctive finishes throughout. Soaring ceilings, graceful archways, and large windows create a bright, welcoming feel from the moment you enter. Marble-look tile flooring extends through the main living areas, while separate living and dining rooms offer flexible space for everyday life and entertaining. At the heart of the home, the kitchen features natural marble countertops, solid wood cabinetry, and soft-close drawers and cabinet doors. A generous island with a gold-tone sink and faucet anchors the space, complemented by a hexagon tile backsplash, coordinating hardware, and contemporary lighting. The adjoining family room makes it easy to stay connected while cooking or hosting guests. A split-bedroom layout provides privacy, and the primary suite features a walk-in closet, garden tub, and separate shower. The covered patio opens to the backyard, offering a place to relax and enjoy Florida’s outdoor lifestyle. The home was renovated in 2021, and the roof and gutters were replaced that same year. A new A/C system and lawn irrigation system were installed in 2023, followed by a new garage door opener in 2026. Located near Winter Garden Village, historic downtown Winter Garden, shopping, dining, and convenient access to SR 429, SR 408, and the Florida Turnpike, this home has plenty to offer. Schedule your private showing today!

12525 Scarlett Sage Court, Winter Garden

$589,990
4 Beds ⋅ 4 Baths ⋅ Storey Grove Ph 2 SubDv. ⋅ 34787 Zip Code
Exceptional Location | Upgraded 4-Bedroom Home | Resort-Style Community Welcome to this beautifully maintained and thoughtfully upgraded 4-bedroom, 3.5-bathroom home offering nearly 2,500 square feet of living space in a highly desirable Central Florida location. Situated in an established community with excellent schools and convenient access to everyday amenities, this home offers an exceptional combination of comfort, convenience, and lifestyle. The home features a spacious and functional floor plan with generously sized bedrooms and inviting living areas. Numerous upgrades throughout the property add both style and functionality, including enhanced kitchen cabinetry, upgraded bedroom features, and other quality finishes that make this home truly move-in ready. Residents enjoy access to an impressive collection of community amenities, including a modern fitness center, resort-style swimming pool, elegant clubhouse, and dedicated young generation recreational areas. The community is designed to provide a comfortable and active lifestyle for families of all ages. The location is equally impressive. Grocery stores, banks, pharmacies, restaurants, convenience stores, and other daily necessities are just minutes away, providing the convenience of an established shopping and service area. Major roads and highways are easily accessible, making commuting and exploring Central Florida convenient. The home is also ideally positioned for easy access to Orlando’s world-famous theme parks and Orlando International Airport, while still offering the comfort and convenience of a well-established residential community. Homes offering this combination of size, condition, upgrades, community amenities, school access, and location are a rare find. Schedule your private showing today and discover everything this exceptional property as well.

14180 Title Way, Winter Garden

$569,900
4 Beds ⋅ 4 Baths ⋅ Belle Meade-Ph I B D & G SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful home in the desirable gated community of Belle Meade in Winter Garden. Offering four bedrooms, four full bathrooms, and a spacious upstairs bonus room. This thoughtfully designed floor plan provides plenty of room for family, guests, and entertaining. The main living areas feature beautiful tile flooring and an open, inviting feel. The well-appointed kitchen showcases 42-inch mahogany cabinetry, granite countertops, a double oven, and stainless steel appliances, creating a functional and attractive space for everyday living and entertaining. The split-bedroom layout provides privacy and flexibility. Two bedrooms and a full bathroom are conveniently located just off the family room, while additional bedrooms and a full bath are situated toward the rear of the home. Upstairs, a large bonus room with its own full bathroom offers a versatile space that can be used as a media room, office, playroom, guest area, or private retreat. The spacious primary suite is located on the opposite side of the first floor and features two walk-in closets along with a primary bathroom complete with a garden tub and enclosed shower. Outside, you’ll appreciate the paver driveway, three-car garage, and the added convenience of being directly across from a neighborhood park. Belle Meade is a gated Winter Garden community convenient located near highly rated schools, downtown Winter Garden, Fowler’s Grove shopping, and major highways. Interior pics will be published soon.

1630 Chandelle Lane, Winter Garden

$598,800
4 Beds ⋅ 3 Baths ⋅ Orchard Hills SubDv. ⋅ 34787 Zip Code
FIRST TIME EVER OFFERED FOR SALE! Welcome to 14543 Sabal Crest Way, an exceptionally maintained, original-owner home located in the highly sought-after Orchard Hills community of Winter Garden. Pride of ownership is evident around every corner of this beautiful single-story residence, offering 4 bedrooms, 3 full baths and 2,224 heated square feet with an ideal combination of comfort, efficiency and location. Just a block from the Orchard Hills clubhouse, fitness center and playground, this home puts some of the community’s best amenities practically at your doorstep. Inside, the heart of the home is an impressive kitchen designed for both everyday living and entertaining. Enjoy built-in double convection ovens, a vented cooktop, abundant cabinetry and an oversized center island overlooking the main living areas. The open, functional one-story floor plan provides excellent separation of space while remaining bright, inviting and easy to live in. The upgrades continue throughout the property, including custom closet systems, gutters, fully fenced backyard and a 220-volt outlet in the garage ready for EV charging. One of the biggest bonuses is the fully paid-off 8.19 kW solar panel system, providing significant dent in the monthly electric savings without the burden of a solar loan or lease. The HOA handles the lawn care too !!! Location of this home is remarkable. Orchard Hills is ideally positioned near the rapidly growing Hamlin retail, dining and commercial district, SR 429 Expressway, Walt Disney World, the new community park and library, and everything Horizon West and Winter Garden have to offer. The property is located within a sought-after K-12 public school district and is also just minutes from the campuses of Foundation Academy and Windermere Preparatory School. Homes combining this condition, one-story living, four bedrooms, three full baths, a fenced yard, community amenities, paid-off solar and an outstanding Winter Garden location are increasingly difficult to find at this value. Meticulously cared for by its original owners, this home is truly move-in ready and an absolute cream puff. You simply won't find more for less. Schedule your private showing and move quickly—14543 Sabal Crest Way is ready for its second owner!

14543 Sabal Crest Way, Winter Garden

$600,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 1c SubDv. ⋅ 34787 Zip Code
PRIVATE POOL & SPA. 3-CAR GARAGE. SINGLE-STORY LIVING. AND JUST 5.8 MILES FROM WALT DISNEY WORLD! Welcome to 16137 Hampton Crossing Drive, where your own private Florida retreat meets the resort-style lifestyle of WATERLEIGH in HORIZON WEST—Winter Garden’s highly desirable newer community corridor. This beautifully maintained DR Horton Arbor floor plan offers 3 BEDROOMS, 3 FULL BATHS and an OVERSIZED 3-CAR TANDEM GARAGE, all thoughtfully arranged across 2,040 square feet on one level. Step inside to a bright, OPEN, SPLIT-BEDROOM FLOOR PLAN with high ceilings, engineered HARDWOOD FLOORING and an easy flow from the kitchen through the dining and living areas. The SPACIOUS kitchen is truly the heart of the home, featuring STONE COUNTERS, abundant cabinetry, stainless steel appliances, a large island with seating and a farmhouse-style sink. The privately positioned PRIMARY SUITE features a tray ceiling, walk-in closet and spacious ENSUITE BATH with DUAL VANITIES and an oversized walk-in shower. Two additional bedrooms and two full baths provide plenty of flexibility for guests, a home office or whatever fits your lifestyle. Then step outside—and this home really starts to show off. The COVERED LANAI opens to a fully SCREENED OUTDOOR RETREAT with your own HEATED SALTWATER POOL AND SPA, generous pool deck and space to relax, entertain or simply ENJOY FLORIDA LIVING year-round. In WATERLEIGH, your backyard is only the beginning. Community amenities include a CLUBHOUSE, RESORT-STYLE POOL, FITNESS CENTER, DOG PARK, PLAYGROUND, sidewalks and access to LAKE HICKORY NUT with fishing opportunities and a community pier. EVEN BETTER—INDIVIDUAL HOMEOWNER LAWN CARE IS INCLUDED, leaving you more time to enjoy everything about this home and community. All of this in HORIZON WEST, one of Central Florida’s most desirable newer communities, and only 5.8 MILES FROM WALT DISNEY WORLD, with shopping, dining, entertainment and major roadways nearby. Your own PRIVATE POOL and SPA, resort-style community amenities AND someone else takes care of the lawn? WELCOME to Florida living!

16137 Hampton Crossing Drive, Winter Garden

$589,000
3 Beds ⋅ 2 Baths ⋅ Tuscany SubDv. ⋅ 34787 Zip Code
**GOLF CART COMMUNITY** Welcome to this charming home located at 1631 Charlemagne Ct in Winter Garden, FL. This beautiful house features three spacious bedrooms, a dedicated office, 2 full bathrooms, living room, dining room (currently using as a second office) laundry room and a two car garage, providing ample space for comfortable living. A beautifully maintained and thoughtfully upgraded home tucked away on a quiet cul-de-sac in one of Winter Garden’s most desirable residential neighborhoods. Sitting on a large, fully fenced lot, this property delivers privacy, peace, and timeless appeal, with mature Oak trees providing lots of shade for outdoor entertaining. With a generous living area of 2,035 square feet, this home accords an inviting layout appropriate for relaxation and entertaining. Step inside and you’re immediately greeted by cathedral ceilings in the living room and kitchen, creating an open, airy atmosphere filled with natural light. Tile flooring throughout the entire home adds a clean, cohesive look while offering durability and easy maintenance. The chef-inspired kitchen is the heart of the home, showcasing upgraded custom cabinetry, and granite countertops. The kitchen features abundant cabinet space and a large pantry offering exceptionally storage for all your kitchen essentials. Included are Bosch appliances and a charming nook overlooking the beautiful mature landscaping. The primary bedroom suite is a truly spacious sanctuary, complete with elegant plantation shutters, a Jacuzzi tub, dual sinks and his-and-her walk-in closets. Two additional bedrooms and a full bath provide comfort and flexibility for family or guests. The laundry room has built-in cabinetry, countertop and additional overhead shelf for added storage. A hall linen closet has extra-large storage providing plenty of space for additional household essentials. Major upgrades bring peace of mind and value including a new roof (2022), exterior freshly painted (2022), Brand-new AC (2024), Newly planted sod in back yard (2026) and upgraded Irrigation Control Panel (2026). Hop on your golf cart just minutes to historic downtown Winter Garden and enjoy your favorite restaurants, events and farmers market. Or take a relaxing nature walk or bike ride on the West Orange trial. This home is move in ready!

1631 Charlemagne Court, Winter Garden

$585,000
2 Beds ⋅ 2 Baths ⋅ N/A SubDv. ⋅ 34787 Zip Code
**Click the Link for Virtual Tour** RARE TURNKEY OPPORTUNITY IN THE HEART OF DOWNTOWN WINTER GARDEN! Just three blocks from Plant Street and located within the golf-cart district, this beautifully renovated 2-bedroom, 2-bathroom cottage combines one of Winter Garden?s most sought-after locations with the flexibility of a primary residence, second home or established short term rental. Thoughtfully renovated down to the studs in 2016, the home blends historic cottage character with extensive modern improvements including updated electrical and plumbing, engineered hardwood floors, renovated kitchen and baths, double-pane windows, natural gas tankless water heater, metal roof and A/C was replaced in 2022. The open floor plan features a charming window seat in the living room, while the primary suite offers a walk-in closet and en-suite bath with dual sinks and oversized shower. A second full bath provides direct exterior access to the backyard - convenient for outdoor entertaining or future pool. Outside, the nearly quarter-acre fenced property offers something increasingly difficult to find this close to downtown: room to enjoy. Relax on the restored rear deck beneath the mature shade tree, utilize the approximately 200-sq.-ft. powered shed as storage, workshop or hobby space, and enjoy the convenience of a carport and additional outdoor space. Leave the car at home and walk, bike or take your golf cart to Plant Street, the West Orange Trail, Plant Street Market, Crooked Can, restaurants, boutiques, the farmers market, festivals and downtown entertainment. Currently operated as a short-term rental and offered turn-key with furnishings and accessories included, with existing reservations extending through March 2027. Whether you're searching for a downtown residence, vacation home or investment property, this is an opportunity to own a distinctive piece of the Downtown Winter Garden lifestyle.

325 W Newell Street, Winter Garden

$575,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2d SubDv. ⋅ 34787 Zip Code
Virtually Staged. The appeal isn’t just the house—it’s the lifestyle that comes with the community. Welcome to 10625 Atwater Bay Drive, Winter Garden, FL 34787, where comfort, convenience, and resort-style living come together in the highly desirable Waterleigh community. The first floor features a private bedroom and full bathroom with a bathtub, ideal for guests, extended family, or convenient first-floor living. The kitchen offers a large center island, granite countertops, ample cabinetry, and a walk-in pantry, opening seamlessly to the living and dining areas. A rear lanai provides a relaxing outdoor space, while the alley-access garage helps maintain the home’s attractive streetscape. Upstairs, a spacious loft offers flexible space for a home office, media room, or playroom. The primary suite features an en-suite bath with dual sinks and a walk-in shower, while two additional bedrooms share another full bath. What truly sets this home apart is the Waterleigh lifestyle. Residents enjoy multiple resort-style pools, fitness centers, clubhouses, playgrounds, sports fields, tennis and pickleball courts, mini-golf, dog parks, walking trails, fishing areas, lakes, green spaces, and community activities. Conveniently located near SR 429, Waterleigh offers easy access to Disney, Orlando, shopping, dining, and entertainment—with Publix located right within the community. 10625 Atwater Bay Drive offers more than a home—it’s an opportunity to enjoy the resort-style lifestyle that makes Waterleigh such a desirable place to live.

10625 Atwater Bay Drive, Winter Garden

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