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$675,000

  • Sold
  • Closed
  • Single Family
  • 3 Beds
  • 1 Full Bath
  • 1,325 Sq. Ft.
See This Home
Save This Home
See This Home
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Prime Winter Park builder and luxury custom home opportunity with rare dual access! Nestled in this Winter Park enclave just one block from the Via Streets, this location offers a massive competitive advantage and features a dedicated rear easement providing direct vehicle or construction access to the adjacent side street (Sunset). Whether you are an investor looking for a high-end project or designing your private sanctuary, this unique dual-access point is a designer's dream-opening up incredible architectural flexibility, private rear-loading/garage options, or seamless construction staging. The property boasts an unobstructed view of the serene park setting at the intersection of Chestnut and Sunset, providing a picturesque backdrop for custom luxury home architecture. Surrounding properties are rapidly redeveloping into spectacular modern estates. Bring your custom builder and your vision to claim one of Winter Park's unique footprints. Property is being sold As-Is with value in the land. One car garage at rear of property with access thru deeded easement. Shed next to garage.

Full Property Details for 1421 Chestnut Ave

General

  • Sold For: $675,000
  • Taxes: $1,881 (2025)
  • Status: Closed
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6442587
  • Added to Site: 56 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 3
  • Interior Features: Ceiling Fan(s)
  • Fireplace: Yes
  • Fireplace(s): Living Room
  • Appliances: Range
  • Furnishings: Unfurnished
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 1
  • Full Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Other

Exterior

  • Exterior Features: Sidewalk

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Covered Spaces: 1

Location

  • Area: 32789 - Winter Park
  • County: Orange
  • Development Name: 32789 - Winter Park
  • Subdivision: LAKE KNOWLES TERRACE
  • Driving Directions: From Aloma and Lakemont proceed north on Lakemont onto Arbor Park Drive then left on Chestnut. Property is on Right.
  • Direction Faces: South

Community

  • Community Name: 32789 - Winter Park

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Public

Structural Information

  • Architectural Info: Traditional
  • Architectural Style: Traditional
  • Exterior Const.: Brick
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,325
  • Sq. Ft. Source: Public Records
  • Living Area: 1,325 Sq. Ft.
  • Year Built: 1952

Lot Features

  • Lot Size (Acres): 0.17
  • Lot Size (Sq. Ft.): 7,441
  • Lot Size: 7441
  • Street/Road Desc.: Brick

Financial Considerations

  • Tax Amount: $1,881.82
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LAKE KNOWLES TERRACE K/4 LOT 25 BLK 1
  • Flood Zone Info: X
  • APN: 322130453601250
  • Property ID: 322130453601250
  • Block/Lot/Section: 1

Listed by Charles Rutenberg Realty Orlando
Sold by Fannie Hillman & Associates

Listing agent

— 1421 Chestnut Ave —

  • Charles Rutenberg Realty Orlando

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 1421 Chestnut Ave

School District:Orange County School District
NameGradesDistance
Lakemont Elementary School
901 North Lakemont Avenue, Winter Park, FL 32792
K-50.6 mi
Maitland Middle School
701 North Thistle Lane, Maitland, FL 32751
6-81.5 mi
Winter Park High School
2100 Summerfield Road, Winter Park, FL 32792
9-122.1 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 1421 Chestnut Ave

Date
Details
Price
Change
Source
10/22/2026
Sold
$675,000
-10%
MLS
9/18/2026
Listed
$750,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Charles Rutenberg Realty Orlando
Sold by Fannie Hillman & Associates

1421 Chestnut Avenue, Winter Park, FL 32789 (MLS# O6442587) is a Single Family property that was sold at $675,000 on October 22, 2026. Want to learn more about 1421 Chestnut Avenue? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.