1421 Chestnut Avenue, Winter Park, FL 32789

Winter Park
Local realty services provided by:Better Homes and Gardens Real Estate Lifestyles Realty
1421 Chestnut Avenue,Winter Park, FL 32789
$750,000
  • 3 Beds
  • 1 Baths
  • 1,325 sq. ft.
  • Single family
  • Active
Listed by: barry sanford pa
Office: charles rutenberg realty orlando
MLS#:O6442587
Source:MFRMLS

Price summary

  • Price:$750,000
  • Price per sq. ft.:$378.79

About this home

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...

Contact an agent

contact an agent

Yes, I would like more information. Please use and/or share my information with a BHGRE®  affiliated agent to contact me about my real estate needs. By clicking Send message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a BHGRE®  affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (CENTURY 21® , Coldwell Banker® , Corcoran® , ERA® , Sotheby's International Realty® ). I acknowledge that I have read and agree to theTerms of useandPrivacy notice

Home facts

  • Year built:1952
  • Subdivision & Development:LAKE KNOWLES TERRACE
  • Listing ID #:O6442587
  • Added:3 day(s) ago
  • Updated:September 21, 2026 at 07:54 PM

Rooms and interior

  • Bedrooms:3
  • Total bathrooms:1
  • Full bathrooms:1
  • Flooring:Wood
  • Kitchen Description:Range
  • Basement Description:Crawlspace
  • Living area:1,325 sq. ft.

Heating and cooling

  • Cooling:Central Air
  • Heating:Electric
  • Central air:Yes

Structure and exterior

  • Roof:Shingle
  • Year built:1952
  • Building area:1,325 sq. ft.
  • Lot area:0.17 Acres
  • Architectural Style:Traditional
  • Construction Materials:Brick
  • Exterior Features:Sidewalk
  • Levels:1 Story

Utilities

  • Water:Public
  • Sewer:Public, Public Sewer

Finances and disclosures

  • Price:$750,000
  • Price per sq. ft.:$378.79
  • Tax amount:$1,882 (2025)

Features and amenities

  • Appliances:Range
  • Amenities:Ceiling Fans(s)
  • Pool features:Public Pool

Parking

  • Garage:Yes
  • Garage spaces:1
MLS LogoThe information being provided by Stellar Mls is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Stellar Mls. Better Homes and Gardens Real Estate Lifestyles Realty is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Better Homes and Gardens Real Estate Lifestyles Realty, a broker participant of Stellar Mls. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Stellar Mls and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited. Properties in listings may have been sold or may no longer be available. Copyright 2026 Stellar Mls. All rights reserved.

New listings near 1421 Chestnut Avenue