Active
118 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

Investment Analysis — 39 Hillside Dr

Sturbridge, MA 01566 — Westville

Based on HUD Small Area Fair Market Rent for Worcester, MA HUD Metro FMR Area, a 4-bedroom in 01566 carries an estimated $3,160/mo in gross rent — about a 3.47% cap rate and $20,841/yr in estimated NOI at the $599,900 list price. Adjust every assumption in the calculator below.

View Standard Listing

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!

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.

Estimates — not financial advice

These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.

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
Primary 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

Primary 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

Listing Provided By

Listing Agent: Jim Black Group

Listing Office: Real Broker MA, LLC

MLS® Number: 73520572