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33 Chestnut St, Milford MA 01757

Milford, MA 01757
$680,000
$659,000
Est. $4,020/month
9
Beds
2
Baths
2,392
Sq Ft
$276
Price/Sq Ft
0.09
Acres
1890
Year Built
4
Parking
212
Days on Market
Pending Price Drop -$21,000 Listed Nov 14, 2025 • MLS# 73455160 Copied! • Updated Jun 15, 2026

About this home

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.

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Recently Sold Nearby

Property History

Market Insights

1
Price Changes
3.1%
Price Range

Property Timeline

📋
Status: Active under contract
Jun 5, 2026
Active → Active Under Contract
Pending Sale
Jun 3, 2026
Offer accepted, sale pending
Price Reduced
Feb 20, 2026
$659,000 $21,000 (-3.09%)
From $680,000 to $659,000 (-3.1%)
🏠
Listed for Sale
Nov 14, 2025
$680,000
Original listing
Office: MIG

Tax History

Year Taxes Assessment
2025 $5,848 $456,900

Financial Details

Annual Property Tax
$5,848
Tax Year 2025
Assessed Value
$456,900

Facts & Features

Home Facts

Type Residential Income
Style Multi Family
Year Built 1890
Living Area 2,392 sq ft
Lot Size 0.09 acres
Bedrooms 9
Full Baths 2
Total Rooms 14

Investment Metrics

Units 2
Unit 1 Rent $2,200/mo · Y
Unit 2 Rent $1,750/mo · Y
Total Monthly Rent $3,950/mo
Gross Income $24,000
Net Operating Income $24,000
Cap Rate 3.64%
Heating None
Cooling None
Flooring Hardwood
Appliances None
Fireplace None
Basement Crawl Space, Unfinished
Laundry None
Features None
Construction None
Architecture None
Roof None
Features None
Pool None
Spa None
Fencing None
Patio/Porch None
Features Paved Drive, Off Street
Total Spaces 4
Electric 100 Amp Service
Water Public
Sewer Public Sewer
Gas None
Other For Electric Oven

Financial

Annual Tax $5,848
Assessed Value $456,900
Fee Includes None
Amenities None
Optional Fee Includes None
Seller Disclosures None
Possession None
Accepted Financing None
Structure Type []
Sq Ft Source Public Record
Documents None
County Worcester
Total market time (incl. prior listings) 213 days

Property Overview

Property Type
Multi Family
Listing Type
For Sale
Year Built
1890
Bedrooms
9
Full Bathrooms
2
Living Area
2,392 sq ft
Total Rooms
14
Stories
3
Levels
3

Room Details

Other Floor

Bathroom1
Bedroom5
Bedroom4
Bedroom3
Dining Room
Kitchen
Bathroom2
Bedroom2
Living Room
Bathroom3
Master Bedroom
Office
Family Room
Master Bathroom

Interior Features

Flooring: Hardwood
Appliances:
Interior Features:
Windows:
Basement: Crawl Space, Unfinished
Laundry:
Security:

Construction & Materials

Year Built: 1890
Structure Type:
Exterior Materials:
Roof:
Foundation: Stone
Stories: 3

Heating, Cooling & Utilities

Heating:
Heating Zones: 1
Cooling:
Hot Water: Oil
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features:
Road Surface:

Parking & Garage

Total Parking Spaces: 4
Parking Features: Paved Drive, Off Street
School District
Milford School District local
C+
School Safety 2024-25
3.8% Above Average
3.2% Suspensions 0.9% In-School 0.6% Emergency
1.7% below state avg
E

Elementary Schools

3 schools
Memorial School
0.7 mi
435 students Diverse
Diverse Student Body
Grades K-02
B+
Memorial School
0.8 mi | #328 of 824 | Score: 49.9
Improved 33 spots from last year
-8.3 below state avg
558 students Moderate
Rising School
Grades K-06
Brookside School
1.0 mi
578 students Diverse
Diverse Student Body
Grades K-02
M

Middle Schools

3 schools
C
Stacy Middle School
0.6 mi | #263 of 352 | Score: 35.3
Improved 32 spots from last year
-22.9 below state avg
989 students Diverse
Rising School
Grades 06-08
A-
Miscoe Hill School
2.7 mi | #99 of 352 | Score: 49.7
Improved 17 spots from last year
-8.5 below state avg
647 students Less Diverse
Strong Attendance
Grades 05-08
C+
Bellingham Memorial Middle School
4.9 mi | #231 of 352 | Score: 38.2
Improved 9 spots from last year
-20 below state avg
586 students Moderate
Grades 04-07
H

High Schools

3 schools
B
Hopedale Jr-Sr High School
1.0 mi | #150 of 346 | Score: 55.5
Dropped 64 spots from last year
-2.7 below state avg
456 students Moderate
15 sports • 874 athletes
Strong AP Program College Ready Curriculum Strong Athletics
Grades 07-12
B-
Milford High School
1.2 mi | #209 of 346 | Score: 50.8
Improved 32 spots from last year
-7.4 below state avg
1,316 students Diverse
17 sports • 1,698 athletes
Early College Program Rising School College Ready Curriculum Strong Athletics
Grades 09-12
Riverside School
1.5 mi
Grades 06-12
Learn about these ratings

Monthly Payment Calculator

Monthly Payment
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Loan Amount
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After down payment
Total Interest
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Over life of loan
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Including down payment
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Down: $0
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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $487
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

Rate Impact

-0.5% Rate
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Current Rate
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+0.5% Rate
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Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Location

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Neighborhood

33 Chestnut St, Milford MA 01757

Milford, MA 01757

Listing Information

Listing Agent Mauricio Florian
Listing Office MIG
Office Phone 617-651-5406
Agent MLS ID CN210316
Office MLS ID AN6265
Listing Data Updated Jun 15, 2026 1:12 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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