Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$749,995

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 3,102 Sq. Ft.
See This Home
Save This Home
See This Home
Save This Home
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.

Full Property Details for 644 Autumn Oaks Loop

General

  • Price: $749,995
  • HOA FEE: $146/month
  • Taxes: $8,987 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6429028
  • Updated: 8/26/2026
  • Added to Site: 47 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

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 644 Autumn Oaks Loop —

  • Condo Metropolis, Llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

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
8/26/2026
Price Reduced
$749,995
-1.32%
MLS
8/14/2026
Price Reduced
$759,995
-2.06%
MLS
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.

Estimate the Cost for 644 Autumn Oaks Loop

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Condo Metropolis, Llc

Similar Properties near 644 Autumn Oaks Loop

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

418 Covered Bridge Dr, Ocoee, FL 34761 - Photo 1
$765,000

418 Covered Bridge Dr  Ocoee, FL 34761

  • Single Family
  • Active
  • 5
    Beds
  • 3
    Total Baths
  • 2,859
    Sq. Ft.
Listed by Creegan Group
2470 Standing Rock Cir, Oakland, FL 34787 - Photo 1 Just Listed
$730,000

2470 Standing Rock Cir  Oakland, FL 34787

  • Single Family
  • Active
  • Updated 2 days ago
  • 5
    Beds
  • 3
    Total Baths
  • 3,430
    Sq. Ft.
Listed by Homevest Realty
7409 Fairgrove Ave, Windermere, FL 34786 - Photo 1
$745,990

7409 Fairgrove Ave  Windermere, FL 34786

  • Single Family
  • Active
  • 5
    Beds
  • 3
    Total Baths
  • 3,285
    Sq. Ft.
Listed by Sunstar Realty Fl Inc
6208 Talaria Dr, Windermere, FL 34786 - Photo 1
$750,000

6208 Talaria Dr  Windermere, FL 34786

  • Single Family
  • Active
  • 5
    Beds
  • 4
    Total Baths
  • 3,373
    Sq. Ft.
Listed by Olympus Executive Realty Inc

Just Listed near 644 Autumn Oaks Loop

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

15607 Vetta Dr, Montverde, FL 34756 - Photo 1 Just Listed
$1,325,000

15607 Vetta Dr  Montverde, FL 34756

  • Single Family
  • Active
  • Updated 5 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,038
    Sq. Ft.
Listed by Selecta Realty Llc
16825 Bay Ave, Montverde, FL 34756 - Photo 1 Just Listed
$119,000

16825 Bay Ave  Montverde, FL 34756

  • Mobile Home
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,350
    Sq. Ft.
Listed by Arellano Realty & Investments
16139 Volterra Point, Montverde, FL 34756 - Photo 1 Just Listed
$965,000

16139 Volterra Point  Montverde, FL 34756

  • Single Family
  • Active
  • Updated 2 days ago
  • 5
    Beds
  • 4
    Total Baths
  • 2,960
    Sq. Ft.
Listed by Bella Collina Real Estate Co
15551 Vinola Ct, Montverde, FL 34756 - Photo 1 Just Listed
$799,000

15551 Vinola Ct  Montverde, FL 34756

  • Single Family
  • Active
  • Updated 13 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,232
    Sq. Ft.
Listed by Lpt Realty, Llc

Price Reduced near 644 Autumn Oaks Loop

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

16401 Pendio Dr, Montverde, FL 34756 - Photo 1 Price Reduced
-$30,000 (-2.17%)
$1,350,000

16401 Pendio Dr  Montverde, FL 34756

  • Lots/Land
  • Active
  • Updated 6 days ago
  • 1.02
    Acres
Listed by Bella Collina Real Estate Co
15950 Vetta Dr, Montverde, FL 34756 - Photo 1 Price Reduced
-$85,000 (-18.48%)
$375,000

15950 Vetta Dr  Montverde, FL 34756

  • Lots/Land
  • Active
  • Updated 6 days ago
  • 0.16
    Acres
Listed by Bella Collina Real Estate Co
17529 Palm Dr, Montverde, FL 34756 - Photo 1 Price Reduced
-$30,000 (-21.58%)
$109,000

17529 Palm Dr  Montverde, FL 34756

  • Mobile Home
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,440
    Sq. Ft.
Listed by Morgan Property Solutions Inc
16300 County Rd 455, Montverde, FL 34756 - Photo 1 Price Reduced
-$20,000 (-5.56%)
$340,000

16300 County Rd 455  #305  Montverde, FL 34756

  • Condo
  • Active
  • Updated 5 days ago
  • 2
    Beds
  • 3
    Total Baths
  • 1,402
    Sq. Ft.
Listed by Bhhs Florida Realty

Recent Sales near 644 Autumn Oaks Loop

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

337 Sunset Oaks Rd, Winter Garden, FL 34787 - Photo 1 Sold
$640,000

337 Sunset Oaks Rd  Winter Garden, FL 34787

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,186
    Sq. Ft.
Listed and Sold by Real Living R E Solutions
615 Lake Cove Pointe Cir, Winter Garden, FL 34787 - Photo 1 Sold
$842,500

615 Lake Cove Pointe Cir  Winter Garden, FL 34787

  • Single Family
  • Closed
  • 4
    Beds
  • 2
    Total Baths
  • 2,465
    Sq. Ft.
Listed by Homevest Realty
Sold by Peyton Blanton
327 S Lakeview Ave, Winter Garden, FL 34787 - Photo 1 Sold
$850,000

327 S Lakeview Ave  Winter Garden, FL 34787

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,225
    Sq. Ft.
Listed by Charles Rutenberg Realty Orlando
Sold by Summerhill Realty Group Llc
408 S Boyd St, Winter Garden, FL 34787 - Photo 1 Sold
$750,000

408 S Boyd St  Winter Garden, FL 34787

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,295
    Sq. Ft.
Listed by Re/Max Prime Properties
Sold by Compass Florida Llc

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 $749,995 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.

Tour this property