39 Hillside Dr, Sturbridge MA 01566

Sturbridge, MA 01566

$649,900

$624,900

Est. $4,025/month

4

Beds

2.5

Baths

2,851

Sq Ft

$219

Price/Sq Ft

1.05

Acres

1987

Year Built

2

Garage Spaces

Single Family Residence

Type

53

Days on Market

Active Price Drop -$25,000 Listed May 18, 2026 • MLS# 73520572 Copied! • Updated Jul 10, 2026

About this home

Nestled on 1.05 acres in a cul-de-sac neighborhood in Sturbridge, this beautifully maintained single-family home offers comfort, space, & thoughtful updates throughout! Step inside to a fireplaced living room that flows into a formal dining room & an expansive, sun-filled family room. An eat-in kitchen w/ granite countertops provides direct access to the deck, creating an easy indoor-outdoor connection, along w/ a convenient half bath on the main level. Upstairs features a spacious primary suite w/ ensuite bathroom, add'l great-sized bedrooms, & a tastefully-remodeled full bath. A partially finished basement adds versatile living space, while the private, flat backyard is ideal for outdoor enjoyment. Notable upgrades & features include a newer boiler, storm doors, garage doors (2026), new septic system (2025) & some windows have been updated w/ Harvey replacement windows. Ideal commuter location w/ ready access to I-90, I-84 and Rt 20 + minutes away from amenities! Home Sweet Home!

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Recently Sold Nearby

Property History

Market Insights

2

Price Changes

3.8%

Price Range

Property Timeline

•

Back On Market

Jul 11, 2026

Active

↓

Price Reduced

Jul 11, 2026

$624,900 $20,000 (-3.1%)

From $644,900 to $624,900 (-3.1%)

📋

Status: Active under contract

Jul 1, 2026

Active → Active Under Contract

↓

Price Reduced

Jun 8, 2026

$644,900 $5,000 (-0.77%)

From $649,900 to $644,900 (-0.8%)

👁️

Showing Instructions Updated

Jun 8, 2026

New showing requirements

🏠

Listed for Sale

May 18, 2026

$649,900

Original listing

Agent: Jim Black Group Office: Real Broker MA, LLC

Date	Event	Price	Change	$/sqft	Details
07/11/2026	• Back On Market	-	-	-	Active
07/11/2026	↓ Price Reduced	$624,900	$20,000	-	From $644,900 to $624,900 (-3.1%)
07/01/2026	📋 Status: Active under contract	-	-	-	Active → Active Under Contract
06/08/2026	↓ Price Reduced	$644,900	$5,000	-	From $649,900 to $644,900 (-0.8%)
06/08/2026	👁️ Showing Instructions Updated	-	-	-	New showing requirements
05/18/2026	🏠 Listed for Sale	$649,900	-	-	Original listing

Tax History

Year	Taxes	Assessment
2025	$7,978	$500,800

Financial Details

Annual Property Tax

$7,978

Tax Year 2025

Assessed Value

$500,800

Facts & Features

2 Car Garage

Home Facts

Type Residential

Style Single Family Residence

Year Built 1987

Living Area 2,851 sq ft

Lot Size 1.05 acres

Bedrooms 4

Full Baths 2

Half Baths 1

Total Rooms 9

Interior

Heating Baseboard, Oil, Electric, Wood

Cooling None

Flooring Tile, Carpet, Hardwood, Flooring - Wall To Wall Carpet

Appliances Water Heater, Range, Dishwasher, Microwave, Plumbed For Ice Maker

Fireplace Living Room

Fireplaces 1

Basement Full, Partially Finished, Walk-out Access, Interior Entry, Concrete

Laundry Flooring - Stone/ceramic Tile, First Floor, Electric Dryer Hookup

Features Closet, Game Room

Exterior

Construction Frame

Architecture Colonial

Roof Shingle

Features Deck - Wood, Rain Gutters, Garden

Pool None

Spa None

Fencing None

Patio/Porch Deck - Wood

Parking

Garage Spaces 2

Has Garage Yes

Features Attached, Garage Door Opener, Storage, Garage Faces Side, Off Street, Paved

Total Spaces 6

Utilities

Electric Circuit Breakers, 200+ Amp Service

Water Private

Sewer Private Sewer

Gas None

Other For Electric Range, For Electric Oven, For Electric Dryer, Icemaker Connection

Financial

Annual Tax $7,978

Assessed Value $500,800

HOA & Community

Fee Includes None

Amenities None

Optional Fee Includes None

Down Payment Resource Eligible

MA Disclosures

Seller Disclosures All Measurements Are Approximate, Buyer Agent To Confirm.

Exclusions Washer, Dryer And Refrigerator

Additional Details

Possession None

Accepted Financing None

Structure Type []

Sq Ft Source Measured

Sq Ft Disclosures Disclosed below-grade living area consists of the finished portion of the basement, approx. 579 sqft

Documents None

County Worcester

Total market time (incl. prior listings) 53 days

Property Overview

Property Type

Single Family Residence

Listing Type

For Sale

Year Built

1987

Bedrooms

4

Full Bathrooms

2

Half Bathrooms

1

Living Area

2,851 sq ft

Total Rooms

9

Room Details

First Floor

Dining Room

14 x 10

Flooring - Hardwood

Kitchen

14 x 12

Flooring - Stone/Ceramic Tile, Balcony / Deck, Countertops - Stone/Granite/Solid, Breakfast Bar / Nook, Exterior Access, Open Floorplan

Living Room

15 x 13

Flooring - Hardwood, Open Floorplan

Bathroom3

6 x 5

Bathroom - Half, Closet, Flooring - Stone/Ceramic Tile

Family Room

21 x 15

Flooring - Hardwood, Open Floorplan

Second Floor

Bathroom1

11 x 5

Bathroom - Full, Bathroom - With Shower Stall, Closet - Linen, Flooring - Stone/Ceramic Tile

Bedroom4

11 x 10

Closet, Flooring - Wall to Wall Carpet

Bedroom3

15 x 12

Closet, Flooring - Wall to Wall Carpet

Bathroom2

9 x 6

Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Remodeled

Bedroom2

15 x 13

Closet, Flooring - Wall to Wall Carpet

Master Bedroom

15 x 15

Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Flooring - Wall to Wall Carpet

Other Floor

Bedroom5

Office

Master Bathroom

Yes

Interior Features

Flooring: Tile, Carpet, Hardwood, Flooring - Wall to Wall Carpet

Appliances: Water Heater, Range, Dishwasher, Microwave, Plumbed For Ice Maker

Interior Features: Closet, Game Room

Windows: Insulated Windows

Basement: Full, Partially Finished, Walk-Out Access, Interior Entry, Concrete

Laundry: Flooring - Stone/Ceramic Tile, First Floor, Electric Dryer Hookup

Security:

Construction & Materials

Style: Colonial

Year Built: 1987

Structure Type:

Exterior Materials: Frame

Roof: Shingle

Foundation: Concrete Perimeter

Heating, Cooling & Utilities

Heating: Baseboard, Oil, Electric, Wood

Heating Zones: 3

Cooling: None

Hot Water:

Water Source: Private

Sewer: Private Sewer

Energy Features: Thermostat

Exterior & Lot

Exterior Features: Deck - Wood, Rain Gutters, Garden

Patio & Porch: Deck - Wood

Fencing:

Other Structures:

Lot Features: Cul-De-Sac, Cleared, Level

Road Surface:

Parking & Garage

Garage Spaces: 2

Garage Type: Attached

Total Parking Spaces: 6

Parking Features: Attached, Garage Door Opener, Storage, Garage Faces Side, Off Street, Paved

Special Features

Fireplaces: 1

Fireplace Type: Living Room

View: Yes

View Type: Scenic View(s)

Community Amenities: Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Conservation Area, Highway Access, House of Worship, Public School

Nearby Schools

School District

Sturbridge School District local

B

✓ School Safety 2024-25

0.0% Very Low (Safest)

↓ 5.5% below state avg

E

Elementary Schools

2 schools

C

Old Sturbridge Academy Charter Public School

2.5 mi | #284 of 352 | Score: 32.8

Improved 33 spots from last year

-25.4 below state avg

356 students Diverse

Rising School

Grades K-08

B+

Burgess Elementary School

2.8 mi | #330 of 824 | Score: 49.9

Improved 87 spots from last year

-8.4 below state avg

842 students Moderate

Rising School

Grades PK-06

M

Middle Schools

1 school

B+

Tantasqua Regional Junior High School

4.1 mi | #143 of 352 | Score: 44.9

Dropped 10 spots from last year

-13.3 below state avg

576 students Less Diverse

Grades 07-08

H

High Schools

2 schools

C+

Tantasqua Regional Vocational High School

6.6 mi | #231 of 346 | Score: 48.4

Improved 19 spots from last year

-9.8 below state avg

542 students Less Diverse

Strong AP Program Career Tech Programs

Grades 09-12

A

Tantasqua Regional Senior High School

6.6 mi | #40 of 346 | Score: 68.4

Improved 65 spots from last year

+10.2 above state avg

632 students Less Diverse

18 sports • 1,532 athletes

Strong AP Program Rising School College Ready Curriculum Strong Athletics

Grades 09-12

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39 Hillside Dr, Sturbridge MA 01566

Sturbridge, MA 01566

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39 Hillside Dr, Sturbridge MA 01566

About this home

Public Records & Permits

BMN Estimate

Recently Sold Nearby

Property History

Market Insights

Property Timeline

Back On Market

Price Reduced

Status: Active under contract

Price Reduced

Showing Instructions Updated

Listed for Sale

Detailed History Table ▼

Tax History

Financial Details

Facts & Features

Home Facts

Interior

Exterior

Parking

Utilities

Financial

HOA & Community

MA Disclosures

Additional Details

Property Overview

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First Floor

Second Floor

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Interior Features

Construction & Materials

Heating, Cooling & Utilities

Exterior & Lot

Parking & Garage

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