$750,000
1421 Chestnut Avenue
Winter Park, FL 32789
Listing updated: September 18, 2026 at 7:04 AM ET
Listing courtesy of Charles Rutenberg Realty Orlando · Barry Sanford PA · MLS #O6442587 · Active · 407-622-2122Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage space
Flood zone
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 value in the land. One car garage at rear of property with access thru deeded easement. Shed next to garage.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history0 days on market
- Status: ActiveSep 18, 2026
- Listed$750,000Sep 18, 2026
- Price increased$750,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 0
- Subdivision
- Lake Knowles Terrace
- County
- Orange
- Year built
- 1952
- Living area
- 1,325 sq ft
- Price/sq ft
- $566
- Building area
- 1,980 sq ft (Public Records)
- Lot size
- 7,441 sq ft
- Lot category
- 0 to less than 1/4
- Flood zone
- X (12095C0255F)
- Garage
- 1 spaces
- Annual taxes
- $1,882 (2025)
- Parcel #
- 32-21-30-4536-01-250
- Zoning
- R-1A
- MLS #
- O6442587
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Interior Details
- Bedrooms
- 3
- Full bathrooms
- 1
- Flooring
- Wood
- Appliances
- Range
- Interior features
- Ceiling Fans(s)
- Laundry
- Other
- Stories / Levels
- One
- Direction faces
- South
- Fireplace
- Yes
Heating & Cooling
- Heating
- Electric
- Cooling
- Central Air
Parking
- Garage spaces
- 1
- Attached garage
- No
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- No Minimum
- Listing terms
- Cash
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
Exterior & Construction
- Exterior features
- Sidewalk
- Construction materials
- Brick
- Roof
- Shingle
- Foundation
- Crawlspace
- Road surface
- Brick
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Public
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | First | |
| Living Room | First | |
| Kitchen | First |
Listing Details
- Listing date
- 2026-09-18
- On market date
- 2026-09-18
- Original list price
- $750,000
- Occupant type
- Vacant
- MLS area
- 32789 - Winter Park
- Listing AOR
- Orlando Regional
- Status changed
- 2026-09-18
- Tax legal description
- LAKE KNOWLES TERRACE K/4 LOT 25 BLK 1
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
From Aloma and Lakemont proceed north on Lakemont onto Arbor Park Drive then left on Chestnut. Property is on Right.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of September 18, 2026 at 7:04 AM ET. 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.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
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