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$775,995 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 3,102 Sq. Ft.
  • Updated 2 days ago
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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.

Full Property Details for 644 Autumn Oaks Loop

General

  • Price: $775,995
  • HOA FEE: $146/month
  • Taxes: $8,987 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6429028
  • Updated: 8/5/2026
  • Added to Site: 2 day(s) ago

Rental Information

  • Min. Lease: 6 Months

Interior

  • Number of Rooms: 8
  • Interior Features: Ceiling Fan(s), Open Floorplan, Smart Home, Walk-In Closet(s), Window Treatments
  • Appliances: Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Ice Maker, Microwave, Refrigerator, Tankless Water Heater, Washer
  • Furnishings: Negotiable
  • Flooring: Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Inside

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground

Exterior

  • Exterior Features: Balcony, Irrigation System
  • Deck/Patio: Covered
  • Porch/Patio/Deck: Covered

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Alley Access

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: WINTER OAKS
  • Driving Directions: From downtown Orlando: Take FL-408 West. Merge onto FL-429 North toward Apopka. Take Exit 24 for Plant Street (FL-438) toward Winter Garden. Turn left (west) onto Plant Street and continue through downtown Winter Garden for about 2 miles. Turn right onto Sunset Oaks Road (entrance to the Winter Oaks community). Turn right onto Autumn Oaks Loop. Continue on Autumn Oaks Loop to 644 Autumn Oaks Loop, which will be on your right.
  • Direction Faces: South

School Information

  • Elementary School: Tildenville Elem
  • Middle School: Lakeview Middle
  • High School: West Orange High

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Association: Yes
  • Assoc. Name: Speciality Management Company

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Electricity Connected, Fiber Optics, Natural Gas Connected

Structural Information

  • Exterior Const.: Block, Metal Frame, Stucco
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 3,102
  • Sq. Ft. Source: Public Records
  • Year Built: 2005

Lot Features

  • Lot Size (Acres): 0.15
  • Lot Size (Sq. Ft.): 6,600
  • Lot Size: 6600
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Association Fee: $146
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $8,987
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WINTER OAKS 53/118 LOT 64
  • Flood Zone Info: X
  • APN: 222227939700640
  • Property ID: 222227939700640
  • Block/Lot/Section: 9397

Listed by Condo Metropolis, Llc

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— 644 Autumn Oaks Loop —

  • Condo Metropolis, Llc

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 644 Autumn Oaks Loop

School District:Orange County School District
NameGradesDistance
Tildenville Elementary School
1221 Brick Road, Winter Garden, FL 34787
PK-50.6 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-80.5 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-122.3 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 644 Autumn Oaks Loop Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/05/2026
Listed
$775,995
12.87%
MLS
11/17/2022
Sold
$687,500
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 644 Autumn Oaks Loop

Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,987
—
$589,840
-1%
2025
$8,987
5%
$597,730
4%
2024
$8,543
-1%
$575,369
6%
2023
$8,622
43%
$541,941
46%
2021
$6,032
9%
$370,869
-4%
2022
$5,521
-8%
$385,598
5%
2021
$6,032
2%
$368,294
4%
2019
$5,926
4%
$355,718
4%
2018
$5,687
12%
$342,575
13%
2017
$5,088
57%
$302,848
33%
2016
$3,251
-2%
$228,075
1%
2015
$3,308
-1%
$226,490
1%
2014
$3,330
2%
$224,692
2%
2013
$3,251
—
$221,371
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Condo Metropolis, Llc

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644 Autumn Oaks Loop, Winter Garden, FL 34787 (MLS# O6429028) is a Single Family property with 5 bedrooms and 3 full bathrooms. 644 Autumn Oaks Loop is currently listed for $775,995 and was received on August 05, 2026. Want to learn more about 644 Autumn Oaks Loop? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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