Active
115 Days on market
39 Hillside Dr Sturbridge — Photo 1 of 41

39 Hillside Dr Sturbridge — Photo 1 of 41

Recent Drop: $50,000

$649,900
$599,900

$599,900

39 Hillside Dr, Sturbridge, MA 01566

Sturbridge, MA 01566 — Westville

Beds

4

Baths

2.5

SqFt

2,851

Style

Single Family

Built

1987

Nestled on 1.05 acres in Sturbridge's desirable Westville neighborhood, this beautifully maintained single-family home offers the perfect blend of privacy, natural beauty, and everyday convenience! Set within a picturesque cul-de-sac, enjoy peaceful surroundings ideal for daily walks and a nature-inspired lifestyle, all while remaining just minutes from local amenities. Step inside to a fireplaced living room that flows into a formal dining room and an expansive, sun-filled family room. An eat-in kitchen with granite countertops provides direct access to the deck, creating an easy indoor-outdoor connection, along with a convenient half bath on the main level. Upstairs features a spacious primary suite with an ensuite bathroom, additional generously sized bedrooms, and a tastefully remodeled full bath. A partially finished basement adds versatile living space, while the private, level backyard is ideal for relaxing or entertaining. Notable upgrades include a newer boiler, storm doors, garage doors (2026), a new septic system (2025), and select Harvey replacement windows. An ideal commuter location with easy access to I-90, I-84, and Route 20. Welcome Home!

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$210/sqft
Local Avg (Sturbridge)$314/sqft
33% BelowMarket Average

* Analysis is based on 21 actively listed and recently sold comparable properties strictly within Sturbridge, MA.

Property Details

Financials

Original Price$649,900
Annual Taxes$7,978

Parking

Garage2
Off-Street6

Interior Specifications

Total Rooms9
Fireplaces1
FlooringTile, Carpet, Hardwood, Flooring - Wall to Wall Carpet
BasementFull, Partially Finished, Walk-Out Access, Interior Entry, Concrete

Climate & Utilities

HeatingBaseboard, Oil, Electric, Wood
CoolingNone
WaterPrivate
SewerPrivate Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
Zoning.

Property & Lot

Acres1.05
SqFt Lot45,738
Lot FeaturesCul-De-Sac, Cleared, Level

Amenities & Appliances

Water Heater • Range • Dishwasher • Microwave • Plumbed For Ice Maker

Neighborhood

Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails • Stable(s)

Geography

Floorplan Breakdown

Structural Layout

Second
Master BedroomBedroom 2Bedroom 3Bedroom 4Bathroom 1Bathroom 2
First
Living RoomDining RoomKitchenFamily RoomBathroom 3
Living Room
Lvl First

15 x 13

Flooring - Hardwood, Open Floorplan

Dining Room
Lvl First

14 x 10

Flooring - Hardwood

Kitchen
Lvl First

14 x 12

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

Family Room
Lvl First

21 x 15

Flooring - Hardwood, Open Floorplan

Master Bedroom
Lvl Second

15 x 15

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

Bedroom 2
Lvl Second

15 x 13

Bedroom 3
Lvl Second

15 x 12

Closet, Flooring - Wall to Wall Carpet

Bedroom 4
Lvl Second

11 x 10

Closet, Flooring - Wall to Wall Carpet

Bathroom 1
Lvl Second

11 x 5

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

Bathroom 2
Lvl Second

9 x 6

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

Bathroom 3
Lvl First

6 x 5

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

Property History

Price Drop
$599,900

Was $624,900

Aug 12, 2026

MLS® 73520572

Price Drop
$624,900

Was $644,900

Jul 11, 2026

MLS® 73520572

Price Drop
$644,900

Was $649,900

Jun 8, 2026

MLS® 73520572

Listed
$649,900

May 18, 2026

MLS® 73520572

Population

7,362

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$138K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

7.7%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Worcester County

1,806 housing units permitted in the last 12 months (-4% vs the prior 12 months) — 1,006 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 2,851 sq ft principal dwelling). Lot size: 45,738 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Listing Provided By

Listing Agent: Jim Black Group

Listing Office: Real Broker MA, LLC

MLS® Number: 73520572

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