1421 CHESTNUT AVENUE,Winter Park,Orange,Land

$750,000
1421 CHESTNUT AVENUE, Winter Park, LAKE KNOWLES TERRACE

Overview

  • October 2, 2026
  • Updated On:
  • 45492
  • Property ID

Description

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.

Address: 1421 CHESTNUT AVENUE
State/County:
Zip: 32789
Country: United States

Property Id: 45492
Price: $750,000
Property Lot Size: 0 ft2
ContractStatusChangeDate: 2026-09-23
Country: United States
CumulativeDaysOnMarket: 5
CurrentUse: Residential
DaysOnMarket: 5
DirectionFaces: South
Directions: From Aloma and Lakemont proceed north on Lakemont onto Arbor Park Drive then left on Chestnut. Property is on Right.
InternetAddressDisplayYN: 1
InternetAutomatedValuationDisplayYN: 1
InternetConsumerCommentYN: 1
InternetEntireListingDisplayYN: 1
Latitude: 28.61386
ListAOR: Orlando Regional
ListAgentAOR: Orlando Regional
ListAgentEmail: barrypsanford@aol.com
ListAgentFullName: Barry Sanford PA
ListAgentKey: 769fc1b49963783516a61a1b1bccaf6e
ListAgentMlsId: 261009260
ListAgentPreferredPhone: 407-694-5598
ListOfficeKey: 7990d74b24680e390c6afbfd23d9689a
ListOfficeMlsId: 50096
ListOfficeName: CHARLES RUTENBERG REALTY ORLANDO
ListPrice: 750000
ListOfficePhone: 407-622-2122
ListingContractDate: 2026-09-18
ListingId: O6442995
ListingTerms: Cash
LivingAreaUnits: Square Feet
Longitude: -81.334242
LotSizeAcres: 0.17
LotSizeArea: 7441
LotSizeDimensions: 50 x 150
LotSizeSquareFeet: 7441
LotSizeUnits: Square Feet
MLSAreaMajor: 32789 - Winter Park
MlsStatus: Pending
ModificationTimestamp: 2026-09-24T00:18:31.107Z
OnMarketDate: 2026-09-18
OriginalEntryTimestamp: 2026-09-18T19:18:06.773Z
OriginalListPrice: 750000
OriginatingSystemKey: stellar
OriginatingSystemName: Stellar MLS
Ownership: Fee Simple
ParcelNumber: 322130453601250
PhotosChangeTimestamp: 2026-09-18T19:30:29.179Z
PhotosCount: 4
PostalCode: 32789
PostalCodePlus4: 1603
RoadSurfaceType: Brick
Sewer: Public Sewer
SourceSystemKey: 811736573
SpecialListingConditions: None
StateOrProvince: FL
StatusChangeTimestamp: 2026-09-24T00:18:31.107Z
StreetName: CHESTNUT
StreetNumber: 1421
StreetNumberNumeric: 1421
StreetSuffix: AVENUE
TaxAnnualAmount: 1881.82
TaxBlock: 1
TaxBookNumber: K-4
TaxLegalDescription: LAKE KNOWLES TERRACE K/4 LOT 25 BLK 1
TaxLot: 25
TaxYear: 2025
UnparsedAddress: 1421 CHESTNUT AVENUE
Utilities: Public
WaterSource: Public
Zoning: R-1A

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$3,845.40
per month
  • Principal and Interest
  • Property Tax
  • HOA fee
  • Private Mortgage Insurance
$ 2,907.90

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