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1421 CHESTNUT AVENUE, WINTER PARK, FL - photo 1

$750,000

1421 CHESTNUT AVENUE

WINTER PARK, FL 32789

LAKE KNOWLES TERRACE

Estimated payment $4,500/month

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3Beds
1Baths
1,325Sq Ft
$566Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

No HOA
Hardwood Flooring
Central Air
South Facing Home
Fireplace
1-Car Garage

About This Home

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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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:3
  • •Bathrooms:1
  • •Full bathrooms:1

Heating

  • •Has Heating:Electric

Cooling

  • •Has Cooling:Central Air

Appliances

  • • Range

Interior area

  • •Total structure area:1,325 sqft
  • •Total interior livable area:1,325 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:1
  • •Has attached garage:No

Lot

  • •Size:0.17 Acres

Details

  • •Parcel number:322130453601250

Type & style

  • •Home type:Residential
  • •Property subtype:Single Family Residence

Materials

  • • Brick

Condition

  • •Year built:1952

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Price history

DateEventPrice
2026-09-18Listed for sale$750,000$566/sqft

Listing Agent

Barry Sanford PA

CHARLES RUTENBERG REALTY ORLANDO

Brokerage Phone: 407-622-2122

License #261009260

Source: STELLAR MLS · MLS #O6442587

Data Powered by Home Junction, Inc.

Nearby

Schools

LAKEMONT ELEMENTARY

Elementary · 0.6 mi

CREALDE SCHOOL OF ARTS

1.1 mi

HERZING UNIVERSITY-WINTER PARK

1.3 mi

Supermarkets

Opportunities-Smg

0.8 mi

Mkt

0.9 mi

Sprouts Farmers Market

1.0 mi

Dining

Patio At Luma

0.3 mi

Asia Kitchen

0.4 mi

Winter Park Racquet Club

0.5 mi

Parks

Sunset/Chestnut Mini Park

0.0 mi

Lake Knowles Park

0.2 mi

Phelps Park

0.4 mi

Beaches

Lake Baldwin Park Beach

2.7 mi

Conrad Beach

18.4 mi

East Beach

18.5 mi

Nearby amenity locations include data © OpenStreetMap contributors.