Amy Caffrey
Compass
(781) 404-3530
54 Total Sales
3 in Needham
$510K - $1.6M Price Range
Estimated Value: $2,099,000 - $2,432,000
20 Windsor Road is a charming home situated on an acre of land in Needham’s desirable estate neighborhood. As you enter, you'll be welcomed by the spacious entryway, the bright and oversized living and dining rooms, and an eat-in kitchen offering views of the spacious yard and new deck leading to the patio and backyard. The first floor also features a home office with its own deck and separate entrance. A few steps down, the large family room offers a bar, billiard area, and ample space for entertaining. This level also connects to the patio, yard, mudroom, and 2-car garage. Upstairs, enjoy new wood floors and three spacious bedrooms, one en suite and the other two sharing a renovated bathroom. Up a level, the oversized primary suite offers views of the yard, new California Closets, and a luxurious spa-like bathroom. The private, sprawling backyard is perfect for a pool, sports court, or any custom addition you desire.
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Amy Caffrey
Compass
(781) 404-3530
54 Total Sales
3 in Needham
$510K - $1.6M Price Range
The Young Group
Leopold & McMasters Realty
(339) 333-8140
77 Total Sales
3 in Needham
$1.2M - $3.6M Price Range
Connie Levine
Keller Williams Realty Boston Northwest
(978) 759-4315
8 Total Sales
1 in Needham
$2,315,000 Price
Brian McMahon
Rutledge Properties
(781) 381-4314
31 Total Sales
2 in Needham
$1.4M - $1.8M Price Range
Kathy Halley
Hammond Residential Real Estate
(857) 567-9109
72 Total Sales
1 in Needham
$1,550,000 Price
S & O Greater Boston Group
Smith and Oak Real Estate Co.
(857) 858-4445
2 Total Sales
1 in Needham
$2,800,000 Price
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 |
|---|---|---|---|
| $2,289,000 | None Available | ||
| Vaczy Daniel | $1,800,000 | None Available | |
| Gillen Maxine | -- | -- |
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 | $600,000 | ||
| Previous Owner | -- | $1,440,000 | |
| Previous Owner | Gillen Maxine | $200,000 | |
| Previous Owner | Gillen Maxine | $230,000 | |
| Previous Owner | 20 Windsor Road Rt | $200,000 |
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 |
|---|---|---|---|---|---|
| 05/02/2025 05/02/25 | Sold | $2,289,000 | +9.1% | $503 / Sq Ft | |
| 03/03/2025 03/03/25 | Pending | -- | -- | -- | |
| 02/26/2025 02/26/25 | For Sale | $2,099,000 | +16.6% | $461 / Sq Ft | |
| 07/30/2021 07/30/21 | Sold | $1,800,000 | +5.9% | $409 / Sq Ft | View Prior Sale |
| 06/14/2021 06/14/21 | Pending | -- | -- | -- | |
| 06/09/2021 06/09/21 | For Sale | $1,699,000 | -- | $386 / Sq Ft |
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 |
|---|---|---|---|---|
| 2025 | $18,878 | $1,780,900 | $797,800 | $983,100 |
| 2024 | $21,497 | $1,717,000 | $719,700 | $997,300 |
| 2023 | $21,543 | $1,652,100 | $719,700 | $932,400 |
| 2022 | $19,276 | $1,441,700 | $547,200 | $894,500 |
| 2021 | $16,783 | $1,288,000 | $547,200 | $740,800 |
| 2020 | $16,632 | $1,331,600 | $547,200 | $784,400 |
| 2019 | $16,453 | $1,327,900 | $547,200 | $780,700 |
| 2018 | $15,775 | $1,327,900 | $547,200 | $780,700 |
| 2017 | $14,690 | $1,235,500 | $547,200 | $688,300 |
| 2016 | $13,294 | $1,152,000 | $547,200 | $604,800 |
| 2015 | $13,006 | $1,152,000 | $547,200 | $604,800 |
| 2014 | $13,286 | $1,141,400 | $547,200 | $594,200 |
Seller's Agent in 2025
The Samantha Eisenberg Group
Compass
124 Total Sales
Seller Co-Listing Agent in 2025
Jared Wilk
Compass
(617) 817-3827
63 Total Sales
Seller Co-Listing Agent in 2025
Samantha Eisenberg
Compass
(917) 952-9966
55 Total Sales
GK
Seller's Agent in 2021
Gary Kaufman
Keller Williams Realty
(617) 721-0785
32 Total Sales
Buyer's Agent in 2021
Gregory Cumings
Prevu Real Estate LLC
(212) 203-2016
58 Total Sales
Source: MLS Property Information Network (MLS PIN)
MLS Number: 73338878
APN: NEED-000211-000056
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