Reduced: Nestled in the sought-after golf cart district just minutes from Historic Downtown Winter Garden, this spacious 5-bedroom, 3-bath smart home in Winter Oaks offers the perfect blend of comfort, style, and convenience. A rear-entry garage enhances the home’s exceptional curb appeal, while the thoughtfully designed floor plan is ideal for both everyday living and entertaining.
The first floor features formal living and dining rooms, a bedroom that also makes an ideal home office, a full bath, a separate laundry room, and a beautifully appointed kitchen with 42-inch cabinetry, granite countertops, stainless steel appliances, and a sunny breakfast area.
Upstairs, the private primary suite provides a peaceful retreat with tray ceilings, a private balcony, an oversized walk-in closet, dual vanities, a garden tub, and a separate walk-in shower. Three additional bedrooms complete the second floor.
Step outside to enjoy the fenced backyard featuring an expansive screened outdoor living area and a private plunge pool/spa, creating your own backyard oasis. Additional highlights include a new roof, tankless water heater, 16-camera security system, landscape lighting, and optional furnishings, including a baby grand piano.
Residents of Winter Oaks enjoy exceptional community amenities, including a resort-style pool, playground, scenic walking trail, tranquil ponds with fountains, and a charming entrance highlighted by a restored historic water tower. Just one mile from the award-winning Winter Garden Farmers Market, Plant Street’s popular shops and restaurants, the West Orange Trail, and convenient SR-429 access, this home offers an exceptional opportunity to enjoy one of Central Florida’s most desirable lifestyles.
The first floor features formal living and dining rooms, a bedroom that also makes an ideal home office, a full bath, a separate laundry room, and a beautifully appointed kitchen with 42-inch cabinetry, granite countertops, stainless steel appliances, and a sunny breakfast area.
Upstairs, the private primary suite provides a peaceful retreat with tray ceilings, a private balcony, an oversized walk-in closet, dual vanities, a garden tub, and a separate walk-in shower. Three additional bedrooms complete the second floor.
Step outside to enjoy the fenced backyard featuring an expansive screened outdoor living area and a private plunge pool/spa, creating your own backyard oasis. Additional highlights include a new roof, tankless water heater, 16-camera security system, landscape lighting, and optional furnishings, including a baby grand piano.
Residents of Winter Oaks enjoy exceptional community amenities, including a resort-style pool, playground, scenic walking trail, tranquil ponds with fountains, and a charming entrance highlighted by a restored historic water tower. Just one mile from the award-winning Winter Garden Farmers Market, Plant Street’s popular shops and restaurants, the West Orange Trail, and convenient SR-429 access, this home offers an exceptional opportunity to enjoy one of Central Florida’s most desirable lifestyles.
Property Details
Price:
$749,995
MLS #:
O6429028
Status:
Active
Beds:
5
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINTER OAKS
Neighborhood:
34787wintergardenoakland
Listed Date:
Aug 5, 2026
Finished Sq Ft:
3,102
Total Sq Ft:
3,874
Lot Size:
6,600 sqft / 0.15 acres (approx)
Year Built:
2005
See this Listing
Schools
Elementary School:
Tildenville Elem
Middle School:
Lakeview Middle
High School:
West Orange High
Interior
Appliances
Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Ice Maker, Microwave, Refrigerator, Tankless Water Heater, Washer
Bathrooms
3 Full Bathrooms
Cooling
Central Air
Flooring
Ceramic Tile
Heating
Central
Interior Features
Ceiling Fan(s), Open Floorplan, Smart Home, Walk-In Closet(s), Window Treatments
Laundry Features
Inside
Levels
Two
Exterior
Attached Garage YN
1
Construction Materials
Block, Metal Frame, Stucco
Covered Spaces
2
Direction Faces
South
Exterior Features
Balcony, Irrigation System
Garage Spaces
2
Parking Features
Alley Access
Patio And Porch Features
Covered
Roof
Shingle
Financial
HOA Fee
$146
HOA Fee Frequency
Monthly
HOA Name
Speciality Management Company
HOA Phone
407-647-2622
Tax Year
2025
Taxes
$8,987
Map
Community
- Address644 AUTUMN OAKS LOOP WINTER GARDEN FL
- SubdivisionWINTER OAKS
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of Aug 29, 2026
826
Single Family Listed
112
Avg DOM
279
Avg $ / SqFt
$758,304
Avg List Price
Property Summary
- Located in the WINTER OAKS subdivision, 644 AUTUMN OAKS LOOP WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $749,995 and features 5 beds, 3 baths, and has approximately 3,102 square feet of living space, and was originally constructed in 2005. The current price per square foot is $242. The average price per square foot for Single Family listings in WINTER GARDEN is $279. The average listing price for Single Family in WINTER GARDEN is $758,304. To schedule a showing of MLS#o6429028 at 644 AUTUMN OAKS LOOP in WINTER GARDEN, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of CONDO METROPOLIS, LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 644 AUTUMN OAKS LOOP
WINTER GARDEN, FL
