1421 Chestnut AvenueWinter Park, FL 32789Price: $750,000

  • Price: $750,000
  • Est. Mortgage of $/month
  • 2 Days on Market
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Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
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1421 Chestnut Avenue Winter Park FL 327891421 Chestnut Avenue Winter Park FL 327891421 Chestnut Avenue Winter Park FL 327891421 Chestnut Avenue Winter Park FL 32789
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  • 3Bedrooms
  • 0.17Acreage
  • 1Bathrooms
  • 1952Year Built
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.
Listing Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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More Info

Location Information

  • Road Frontage DescriptionBrick

Rooms

  • Bedrooms3
  • Full Bath1

Location

  • Address1421 Chestnut Avenue
  • AreaWinter Park
  • CountyOrange
  • Exterior Features Sidewalk
  • StateFL
  • SubdivisionLake Knowles Terrace
  • TownWinter Park
  • Township 21
  • Zip32789

Property Information

  • Acreage0.17
  • Building Area Total 1,980
  • BuildingAreaUnitsSquare Feet
  • LivingAreaUnitsSquare Feet
  • Lot Size Square Feet 7,441
  • MFR Living Area Meters 123
  • MFR Lot Size Square Meters 691
  • MFR Total Acreage 0 to less than 1/4
  • Square Feet1,325

Basic Information

  • List Price$750,000
  • ListingContractDate2026-09-18
  • MLS NumberO6442587
  • Mls Status Active
  • OriginalListPrice750000
  • PostalCodePlus41603
  • PublicSurveyRange30
  • StatusACT

Property

  • ZoningR-1A

Interior

  • Flooring Wood
  • Furnished Unfurnished

Utilities

  • Cooling Central Air
  • Heating Electric
  • Laundry Features Other
  • Sewer Public Sewer
  • Utilities Public
  • Water Source Public

Water Body

  • MFR Water Access YN No
  • Water ViewNo

Other

  • Building Area Source Public Records
  • Date Listed09/18/2026
  • MFR Exist Lse Tenant YN No
  • MFR Flood Zone Code X
  • MFR Flood Zone Date 2009-09-25
  • MFR Minimum Lease No Minimum
  • Status Change Timestamp2026-09-18T10:36:09
  • View Count1

Tax Information

  • Tax Year 2025
  • Taxes$1,881

Basic Information

  • Property SubTypeSingle Family Residence
  • Property TypeResidential

Building

  • Bathroom1
  • Construction Materials Brick
  • FireplaceLiving Room
  • Fireplace YN Yes
  • Foundation Details Crawlspace
  • GarageYes
  • Garage Spaces1
  • Levels One
  • Property StyleTraditional
  • RoofShingle
  • Rooms3
  • Stories1
  • Year Built1952

Amenities

  • Appliances IncludedRange
  • Other AmenitiesFireplace

Legal

  • Listing Agreement Exclusive Right To Sell
  • Parcel Number 32-21-30-4536-01-250
  • Tax Legal Description LAKE KNOWLES TERRACE K/4 LOT 25 BLK 1
Fusilier Realty Group

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Fusilier Realty Group
Office: 407-281-8455
10016 Wellness Way
Orlando, FL 32832

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of September 19, 2026 8:04 AM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively 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. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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