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1421 CHESTNUT AVENUE

House For Sale
$750,000

BTC: 8.76680304

ETH: 300.00000000

3 days
3 bds
1 ba
1,325 sqft

Overview

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.

Location

Details

Type:
Residential
Parking:
No Data
Year Built:
1952
Lot:
0.17 Acres
Heating:
Electric
Price/sqft:
$566
Cooling:
Central Air
HOA:
No Data

Valuation

Our model vs. what's actually selling nearby.
Estimate
$429,950
$306K – $667K
Confidence Low
List vs. estimate
$320K above estimate
List $750,000 · +74.4%
Our model says this listing is priced above recent comparable activity. Room to negotiate.
Price per sq ft
$566
+30.0% vs. city median $435
Based on
54 MLS comparables
Median of recent comparable listings. Sold comps use closing price, active listings use list price.

Highlights

Annual tax
$1,881
2025
Garage
1 car garage
All facts and features
  • Flooring

    • Hardwood

    Heating

    • Electric

    Cooling

    • Central Air

    Appliances

    • Range

    Other interior features

    • Ceiling Fan(s)

    Bedrooms and bathrooms

    • Bedrooms: 3

    • Full bathrooms: 1

  • Property

    • Levels: One

    • Exterior Features: Sidewalk

    Lot

    • Lot: 0.17 Acres

    Other Property Information

    • Parcel Number: 322130453601250

    • Zoning: R-1A

  • Type and style

    • Property Type: Residential

    • Property Sub Type: Single Family Residence

  • Utility

    • Public

  • Other financial information

    • Annual tax amount: $1,882

  • Source details

    • MLS ID: O6442587

    Other facts

    • Construction Materials: Brick

    • Foundation Details: Crawlspace

    • Fireplace Features: Living Room

    • Laundry Features: Other

    • Direction Faces: South

    • Architectural Style: Traditional

    • Fireplace: Yes

    • Garage Spaces: 1

    • Garage: Yes

    • Living Area: 1325

    • Water Source: Public

    • Subdivision Name: LAKE KNOWLES TERRACE

Private inquiry
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The multiple listing information is provided by the Stellar MLS from a copyrighted compilation of listings. The compilation of listings and each individual listing are ©2026-present Stellar MLS. All Rights Reserved. The information provided is for consumers' personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Listing courtesy of: CHARLES RUTENBERG REALTY ORLANDO