For sale

Price cut: $21K (2/20)

$659,000

33 Chestnut St, Milford, MA 01757

9beds

2,392sqft

Est.:

Multi Family

Built in 1890

-- sqft lot

$653,100 Zestimate^®

$276/sqft

$-- HOA

What's special

Family roomEat in kitchenHardwood floorsLow maintenance lotGood natural light

Welcome to 33 Chestnut St, a large two family right in the heart of Milford. This property offers 2,392 sq ft of living area, 14 total rooms and 9 bedrooms, giving you the size and flexibility you don’t usually find at this price point.Unit 1 is a spacious first floor 4 bedroom with hardwood floors, good natural light and an eat in kitchen. Unit 2 is spread across two levels with 5 bedrooms, a family room, an eat in kitchen and extra flex rooms that work well for office or storage. Perfect setup for an investor or an owner occupant who needs more space.The home sits on a low maintenance lot with parking for 4 cars, vinyl siding, town water and town sewer. Unit 1 is rented at $2,000 per month and Unit 2 will be delivered vacant, so the next owner can move in or bring rents to market.Close to downtown, shops and public transportation. Strong rental potential and a lot of upside in a growing area of Milford.

109 days

1,689

66

Tour with a local agent

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 9
Bathrooms: 2
Full bathrooms: 2

Features

Flooring: Hardwood
Basement: Crawl Space,Unfinished
Has fireplace: No

Interior area

Total structure area: 2,392
Total interior livable area: 2,392 sqft
Finished area above ground: 2,392

Property

Parking

Total spaces: 4
Parking features: Paved Drive, Off Street
Uncovered spaces: 4

Lot

Size: 3,798 Square Feet

Details

Parcel number: M:48 B:000 L:156,1617570
Zoning: RA

Construction

Type & style

Home type: MultiFamily
Property subtype: Multi Family

Materials

Foundation: Stone

Condition

Year built: 1890

Utilities & green energy

Electric: 100 Amp Service
Sewer: Public Sewer
Water: Public
Utilities for property: for Electric Oven

Community & HOA

Community

Features: Public Transportation

Location

Region: Milford

Financial & listing details

Price per square foot: $276/sqft
Tax assessed value: $456,900
Annual tax amount: $5,848
Date on market: 11/14/2025
Total actual rent: 2000

Estimated market value

$653,100

$620,000 - $686,000

$2,260/mo

Price history

Date	Event	Price
2/20/2026	Price change	$659,000-3.1%$276/sqft
Source: MLS PIN #73455160 Report a problem
11/14/2025	Listed for sale	$680,000+525.3%$284/sqft
Source: MLS PIN #73455160 Report a problem
7/1/2010	Sold	$108,750-12.9%$45/sqft
Source: Public Record Report a problem
5/12/2010	Price change	$124,900-10.7%$52/sqft
Source: Fatima Afonso #71040861 Report a problem
4/3/2010	Price change	$139,900-6.7%$58/sqft
Source: Fatima Afonso #71040861 Report a problem
3/4/2010	Listed for sale	$149,900+66.6%$63/sqft
Source: Fatima Afonso #71040861 Report a problem
12/10/1990	Sold	$90,000$38/sqft
Source: Public Record Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$5,848 +2.7%	$456,900 +6.7%
2024	$5,693 +8.7%	$428,400 +18.2%
2023	$5,235 +2.5%	$362,300 +9.2%
2022	$5,106 +6.6%	$331,800 +10.6%
2021	$4,792 +2.4%	$299,900 +2.3%
2020	$4,679 +10.1%	$293,200 +14.1%
2019	$4,249 +10.5%	$256,900 +10.6%
2018	$3,845 +2.9%	$232,200 +4.4%
2017	$3,736 +2.5%	$222,500 +4.9%
2016	$3,646 +3.1%	$212,200 +5.3%
2015	$3,536 +3.2%	$201,500 +4%
2014	$3,428 +2.5%	$193,800 -1.7%
2013	$3,343 +2.7%	$197,200 -2%
2012	$3,255 -1%	$201,300 -6.8%
2011	$3,289 +2.4%	$216,100 -5.3%
2010	$3,213 -9.5%	$228,200 -19.5%
2009	$3,551 +0.2%	$283,400 -5.6%
2008	$3,544 +4.8%	$300,300 -3.3%
2007	$3,383 +11.8%	$310,400 +16.4%
2006	$3,026 +2.5%	$266,600 +6.9%
2005	$2,952 +2.6%	$249,500 +3.5%
2004	$2,878 +40.9%	$241,000 +57.6%
2003	$2,043 +1.3%	$152,900 +8.3%
2002	$2,016 +19.8%	$141,200 +36.7%
1998	$1,683	$103,300