M
Landlord's Agent in 2026
Matthew Kirsch
REAL PROPERTY MANAGEMENT AND REALTY
(407) 897-3366
71 Total Sales
1641 Chestnut Ave Winter Park, FL 32789
Estimated Value: $735,000 - $874,000
3
Beds
3
Baths
1,750
Sq Ft
$457/Sq Ft
Est. Value
Highlights
- 1 Car Attached Garage
- Central Heating and Cooling System
- 1-Story Property
- Winter Park High Rated A
- Ceiling Fan
About This Home
As of January 2026Welcome to your new home nestled along Winter Park’s coveted tree-lined Chestnut Avenue. This beautiful 3 bedroom, 3 bathroom home blends classic charm with modern updates and is perfectly situated near Park Avenue, Phelps Park, the YMCA, Winter Park golf course, and Lakemont Elementary School. Upon entering, you’ll be greeted by gleaming hardwood floors flowing through an inviting, light-filled layout. The heart of the home is the window-lined kitchen, thoughtfully refreshed with newer cabinetry, appliances, and a cozy eat-in bar, perfect for casual dining or morning coffee. The peaceful primary suite offers a serene retreat, complete with elevated ceilings and direct views of the outdoors. Step outside onto the private brick patio and enjoy the fenced backyard. With its delightful updates, prime location near schools, parks, and Park Avenue’s vibrant shops and restaurants, this home is sure to capture your heart. Schedule a showing or submit an application online. All Real Property Management & Realty residents enjoy convenience and well-maintained homes, with our safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, and a 24/7 emergency maintenance response team. Please note the listed amenities may not be accurate.
Last Agent to Rent the Property
REAL PROPERTY MANAGEMENT AND REALTY Brokerage Phone: 407-897-3366 License #3289680 Listed on: 08/26/2025
Home Details
Home Type
- Single Family
Year Built
- Built in 1959
Lot Details
- 7,520
Parking
- 1 Car Attached Garage
Interior Spaces
- 1,750 Sq Ft Home
- 1-Story Property
- Ceiling Fan
- Washer and Electric Dryer Hookup
Kitchen
- Range
- Microwave
- Dishwasher
Bedrooms and Bathrooms
- 3 Bedrooms
- 3 Full Bathrooms
Additional Features
- 7,520 Sq Ft Lot
- Central Heating and Cooling System
Community Details
- Property has a Home Owners Association
- Lake Knowles Terrace Subdivision
Listing and Financial Details
- Residential Lease
- Security Deposit $3,245
- Property Available on 8/26/25
- 12-Month Minimum Lease Term
- Available 1/8/26
- $85 Application Fee
- Assessor Parcel Number 32-21-30-4536-01-070
Ownership History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Mar 16, 2013
Closed on
Aug 16, 2013
Sold by
Bought by
Buyer's Agent
Kathryn McCrea
MCCREA REALTY LLC
List Price
$319,000
Sold Price
$290,000
Premium/Discount to List
-$29,000
-9.09%
Current Estimated Value
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
$509,455
Avg. Annual Appreciation
8.21%
Original Mortgage
$232,000
Outstanding Balance
$169,422
Interest Rate
4.48%
Mortgage Type
New Conventional
Estimated Equity
$630,033
Purchase Details
Closed on
Jan 26, 2006
Sold by
Bought by
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$260,000
Interest Rate
6.08%
Mortgage Type
New Conventional
Purchase Details
Closed on
Apr 22, 2002
Sold by
Bought by
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$200,000
Interest Rate
6.89%
Mortgage Type
New Conventional
Purchase Details
Closed on
Apr 10, 2000
Sold by
Bought by
Purchase Details
Closed on
Mar 2, 1999
Sold by
Bought by
Purchase Details
Closed on
Jan 18, 1994
Sold by
Bought by
Purchase Details
Closed on
Jun 29, 1993
Sold by
Bought by
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Home Values in the Area
Average Home Value in this Area
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| $290,000 | None Available | ||
| -- | None Available | ||
| $266,500 | -- | ||
| $217,000 | -- | ||
| $99,000 | -- | ||
| $80,500 | -- | ||
| $1,000 | -- |
Source: Public Records
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Borrower | Loan Amount |
|---|---|---|---|
| Open | $232,000 | ||
| Previous Owner | $260,000 | ||
| Previous Owner | $235,000 | ||
| Previous Owner | $200,000 | ||
| Previous Owner | $25,000 |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 01/08/2026 01/08/26 | Rented | $3,295 | 0.0% | -- | |
| 12/10/2025 12/10/25 | Under Contract | -- | -- | -- | |
| 11/10/2025 11/10/25 | Price Changed | $3,295 | -5.7% | $2 / Sq Ft | |
| 10/13/2025 10/13/25 | Price Changed | $3,495 | -2.8% | $2 / Sq Ft | |
| 09/29/2025 09/29/25 | Price Changed | $3,595 | -2.7% | $2 / Sq Ft | |
| 09/11/2025 09/11/25 | Price Changed | $3,695 | -7.5% | $2 / Sq Ft | |
| 08/26/2025 08/26/25 | For Rent | $3,995 | 0.0% | -- | |
| 05/26/2015 05/26/15 | Off Market | $290,000 | -- | -- | |
| 08/16/2013 08/16/13 | Sold | $290,000 | -1.7% | $166 / Sq Ft | View Prior Sale |
| 07/03/2013 07/03/13 | Pending | -- | -- | -- | |
| 06/28/2013 06/28/13 | Price Changed | $295,000 | -1.3% | $169 / Sq Ft | |
| 06/05/2013 06/05/13 | Price Changed | $299,000 | -3.5% | $171 / Sq Ft | |
| 05/10/2013 05/10/13 | Price Changed | $309,900 | -1.6% | $177 / Sq Ft | |
| 04/13/2013 04/13/13 | Price Changed | $315,000 | -1.3% | $180 / Sq Ft | |
| 03/16/2013 03/16/13 | For Sale | $319,000 | -- | $182 / Sq Ft |
Source: Stellar MLS
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2026 | $4,207 | $581,010 | $400,000 | $181,010 |
| 2025 | $4,207 | $641,880 | $400,000 | $241,880 |
| 2024 | $3,903 | $300,737 | -- | -- |
| 2023 | $3,903 | $283,749 | $0 | $0 |
| 2022 | $3,646 | $275,484 | $0 | $0 |
| 2021 | $3,598 | $267,460 | $0 | $0 |
| 2020 | $3,457 | $263,767 | $0 | $0 |
| 2019 | $3,569 | $257,837 | $0 | $0 |
| 2018 | $3,544 | $253,029 | $0 | $0 |
| 2017 | $3,507 | $318,184 | $230,720 | $87,464 |
| 2016 | $3,433 | $309,978 | $224,000 | $85,978 |
| 2015 | $3,515 | $297,055 | $197,000 | $100,055 |
| 2014 | $3,543 | $239,128 | $150,000 | $89,128 |
Source: Public Records
Agents Affiliated with this Home
-
Matthew Kirsch
-
Shelby Kirsch
S
Tenant's Agent in 2026
Shelby Kirsch
REAL PROPERTY MANAGEMENT AND REALTY
(941) 735-0819
18 Total Sales
-
Kathryn McCrea
K
Buyer's Agent in 2013
Kathryn McCrea
MCCREA REALTY LLC
(321) 303-3578
6 Total Sales
Map
Source: Stellar MLS
MLS Number: O6338990
APN: 32-2130-4536-01-070
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
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. Some IDX listings have been excluded from this website. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Listings courtesy of Stellar MLS as distributed by MLS GRID.
Based on information submitted to the MLS GRID
Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
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