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$899,000

1621 Chestnut Avenue

Winter Park, FL 32789

Listing updated: August 21, 2026 at 6:52 AM ET

Active

Listing courtesy of Kelly Price & Company Llc · Kelly Price · MLS #O6435086 · Active · 407-645-4321

Beds

Baths

2,022

Sq Ft

0.17

Acres

1970

Built

◆$445/sqft

Single Family Residence

Property type

1970

Year built

7,512 sqft

Lot size

$445

Price / sq ft

No HOA

HOA dues

Day on market

Garage spaces

Flood zone

About this home

Welcome to 1621 Chestnut Avenue, ideally situated in the heart of Winter Park's coveted "Tree Streets" neighborhood. Offered at $899,000, this single-story block home sits on a generous 50x150' lot and offers 2,022 square feet of living space with 3 bedrooms and 2.5 baths. Whether you envision a thoughtful remodel or a ground-up new build, this property presents outstanding potential in one of Winter Park's most desirable pockets, where similar transformations are already reshaping the streetscape. Inside, tile flooring flows through the main living areas, complementing a versatile layout that includes a formal living room, a combined kitchen and dining area, and a separate den with pocket doors perfect for a home office or media room. The oversized bedrooms offer generous space throughout, including a primary suite with a private en suite bath. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, ideal for family or guests. At the rear of the home, an enclosed sunroom provides a peaceful retreat overlooking the well-manicured backyard, a tranquil spot to relax and unwind. With its prime location, solid bones, and abundant possibilities, 1621 Chestnut Avenue is ready for its next owner to make it their own.

Estimated monthly payment

Principal & interest$4,546

Property taxes$276

Home insurance (est.)$412

Down payment

20%

$179,800 downRate

6.5%

Term

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 history1 days on market

Status: Active
Aug 20, 2026
Listed$899,000
Aug 20, 2026
Price increased$899,000

Facts & features

Property type: Residential
Sub type: Single Family Residence
Status: Active
Days on market: 1
Subdivision: Lake Knowles Terrace
County: Orange
Year built: 1970
Living area: 2,022 sq ft
Price/sq ft: $445
Building area: 2,715 sq ft (Public Records)
Lot size: 7,512 sq ft
Lot category: 0 to less than 1/4
Flood zone: X (12095C0255F)
Garage: 2 spaces
Annual taxes: $3,312 (2025)
Parcel #: 32-21-30-4536-01-090
Zoning: R-1A
MLS #: O6435086

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Interior Details

Bedrooms: 3
Full bathrooms: 2
Half bathrooms: 1
Flooring: Carpet, Tile, Wood
Appliances: Built-In Oven, Cooktop, Dishwasher, Refrigerator
Interior features: Ceiling Fans(s)
Laundry: Laundry Room
Stories / Levels: One
Direction faces: South

Heating & Cooling

Heating: Central, Electric
Cooling: Central Air

Parking

Garage spaces: 2
Attached garage: Yes
Parking features: Driveway

HOA & Financial

Total monthly fees: $0/mo
Total annual fees: $0
CDD: No
Homestead exemption: Yes
Min lease term: No Minimum
Ownership: Fee Simple
Available for lease: Yes
Lease restrictions: No
Additional lease restrictions: Buyer to verify and and all lease restrictions with local municipality

Exterior & Construction

Exterior features: Sidewalk
Construction materials: Block
Roof: Shingle
Foundation: Slab
Road surface: Brick

Utilities

Sewer: Public Sewer
Water source: Public
Utilities: BB/HS Internet Available, Cable Available

Schools

ElementaryBLakemont ElemGreatSchools ↗

MiddleBMaitland MiddleGreatSchools ↗

High SchoolAWinter Park HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

Room	Level	Dimensions
Living Room	First	12x17
Dining Room	First	17x11
Kitchen	First	14x11
Den	First	16x12
Primary Bedroom	First	14x12
Bedroom 2	First	16x12
Bedroom 3	First	16x15
Laundry	First	8x12

Listing Details

Listing date: 2026-08-20
On market date: 2026-08-20
Original list price: $899,000
Occupant type: Owner
MLS area: 32789 - Winter Park
Listing AOR: Orlando Regional
Status changed: 2026-08-20
Tax legal description: LAKE KNOWLES TERRACE K/4 LOT 9 BLK 1

Flood risk

Minimal riskFEMA Zone XPanel 12095C0255F

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 Temple: Head East on Chestnut. Home is on left.

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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 August 21, 2026 at 6:52 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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