1421 CHESTNUT AVENUE Winter Park, FL $ 750,000
1421 CHESTNUT AVENUE
$ 750,000
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1421 CHESTNUT AVENUE

Winter Park, FL, 32789
$ 750,000
Bedrooms3 Baths1.0 Sq 1,325

Monthly Estimate*

$ 5,180

1421 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 1
1421 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 2
1421 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 3
1421 CHESTNUT AVENUE, Winter Park, FL 32789 - Image 4

Single Family Home for sale in Winter Park, FL

for $750,000 with 3 bedrooms and 1 full bath. This 1,325 square foot home was built in 1952 on a lot size of 0.17.

Under contract-accepting backup offers. 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.

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Single Family Contingent

Price

$ 750,000

Bedrooms

3

Full Bath

1

Property Type

Single Family

Taxes

$ 1,881

Style

Traditional

Lot Size

0.17

Year Built

1952

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6442587

Features
General
Sewer Public Sewer
Heating Electric
Cooling Central Air
Utilities Public
Roof Shingle
Appliances Range
Zoning R-1A
Garage Spaces 1
Architectural Style Traditional
Construction Materials Brick
Year Built 1952
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
County Orange
New Construction false
Property Type Residential
Attached Garage false
Subdivision Name LAKE KNOWLES TERRACE
Facing Direction South
Garage Y/N true
Total Rooms 3
Full Baths 1
Status Pending
Directions From Aloma and Lakemont proceed north on Lakemont onto Arbor Park Drive then left on Chestnut. Property is on Right.
City WINTER PARK
Senior Community Y/N false
MLS Area 32789 - Winter Park
Lot Size Units Square Feet
Lot Size Square Feet 7441
Carport Y/N false
Listing Terms Cash
Land Lease Y/N false
Tax Annual Amount 1881.82
Additional Parcels Y/N false
Lease Considered Y/N true
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active Under Contract
Occupancy Type Vacant
Tax Lot 25
Legal Description LAKE KNOWLES TERRACE K/4 LOT 25 BLK 1
Minimum Lease No Minimum
Water Access Y/N false
Water View Y/N false
Flood Zone Code X
In Law Suite YN false
Flood Zone Code X Y
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Interior
Interior Amenities Ceiling Fan(s)
Flooring Hardwood
Furnished Y/N Unfurnished
Fireplace Features Living Room
Total Stories 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 0
Laundry Features Other
Total Bedrooms 3
Total Baths 1
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Exterior
Exterior Amenities Sidewalk
Water Source Public
Lot Size Area 7441
Foundation Details Crawlspace
Building Area Total 1980
Lot Size Acres 0.17
Road Surface Type Brick
Private Pool false
Waterfront Y/N false
Covered Spaces 1
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* Excluded Features
List By
Charles Rutenberg Realty Orlando

Broker

barrypsanford@aol.com

Email

Affordability Calculator

$5,337
Per Month
97%
3%
0%
Monthly Principal & Interest
$5,180
Monthly Property Taxes
$157
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4827338 Elementary School
4827337 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
9/18/2026$750,000 Listed Price

Map


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1421 CHESTNUT AVENUE, Winter Park, FL, 32789 is a Single Family Home for sale at $750,000 with 1,325 sqft and a lot size of 0.17. 1421 CHESTNUT AVENUE has 3 bedrooms, 1.0 baths, and was built in 1952. The property's zip code is 32789 which is in Winter Park, FL