There are multiple listings for this address:
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.
Property Details
Price:
$750,000
MLS #:
O6442587
Status:
Active Under Contract
Beds:
3
Baths:
1
Type:
Single Family
Subdivision:
LAKE KNOWLES TERRACE
Neighborhood:
32789winterpark
Listed Date:
Sep 18, 2026
Finished Sq Ft:
1,325
Lot Size:
7,441 sqft / 0.17 acres (approx)
See this Listing
Schools
Interior
Exterior
Direction Faces
South
Financial
Tax Year
2025
Taxes
$1,882
Map
Community
- Address1421 CHESTNUT AVENUE WINTER PARK FL
- SubdivisionLAKE KNOWLES TERRACE
- CityWINTER PARK
- CountyOrange
- Zip Code32789
Subdivisions in WINTER PARK
Market Summary
Current real estate data for Single Family in WINTER PARK as of Oct 18, 2026
281
Single Family Listed
83
Avg DOM
476
Avg $ / SqFt
$1,330,538
Avg List Price
Property Summary
- Located in the LAKE KNOWLES TERRACE subdivision, 1421 CHESTNUT AVENUE WINTER PARK FL is a Single Family for sale in WINTER PARK, FL, 32789. It is listed for $750,000 and features 3 beds, 1 baths, and has approximately 1,325 square feet of living space.The current price per square foot is $566. The average price per square foot for Single Family listings in WINTER PARK is $476. The average listing price for Single Family in WINTER PARK is $1,330,538. To schedule a showing of MLS#o6442587 at 1421 CHESTNUT AVENUE in WINTER PARK, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
Similar Listings Nearby
Courtesy of CHARLES RUTENBERG REALTY ORLANDO. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 1421 CHESTNUT AVENUE
WINTER PARK, FL
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.
Property Details
Price:
$750,000
MLS #:
O6442995
Status:
Active Under Contract
Beds:
0
Baths:
0
Type:
Land
Subdivision:
LAKE KNOWLES TERRACE
Neighborhood:
32789winterpark
Listed Date:
Sep 18, 2026
Lot Size:
7,441 sqft / 0.17 acres (approx)
See this Listing
Schools
Interior
Exterior
Direction Faces
South
Financial
Tax Year
2025
Taxes
$1,882
Map
Community
- Address1421 CHESTNUT AVENUE WINTER PARK FL
- SubdivisionLAKE KNOWLES TERRACE
- CityWINTER PARK
- CountyOrange
- Zip Code32789
Subdivisions in WINTER PARK
Market Summary
Current real estate data for Land in WINTER PARK as of Oct 18, 2026
281
Land Listed
83
Avg DOM
476
Avg $ / SqFt
$1,330,538
Avg List Price
Property Summary
- Located in the LAKE KNOWLES TERRACE subdivision, 1421 CHESTNUT AVENUE WINTER PARK FL is a Land for sale in WINTER PARK, FL, 32789. It is listed for $750,000 and features 0 acres. To schedule a showing of MLS#o6442995 at 1421 CHESTNUT AVENUE in WINTER PARK, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
