Under contract

$479,900

27 Hillside Dr, Sturbridge, MA 01566

3beds

2,209sqft

$3,479/mo

Get pre-qualified

Single Family Residence

Built in 1970

0.95 Acres Lot

$474,000 Zestimate^®

$217/sqft

$-- HOA

What's special

Brick walkwayFire pitLarge sunny backyardQuiet cul-de-sac streetInviting open-concept layoutDining areaAll hardwood flooring

Check out this gorgeous large sunny back yard with inviting IG pool! Welcome home to this spacious 3 BR 2 BA Home located in the desirable Hillside Drive Neighborhood! Situated on a quiet cul-de-sac street, this home offers a convenient location for commuters while being just minutes to shopping, dining and everyday amenities. The spacious main living level features all hardwood flooring and an inviting open-concept layout, for the Living Rm, Dining Area and Kitchen with a center island-perfect for entertaining. The Primary BR enjoys direct access to the recently renovated full Bath, while 2 additional Bedrooms complete this floor. The finished lower level offers additional living area with a Family Rm, and the 2nd Full Bath, ideal for guests, at home office or recreation area. Double French Doors from the main living area lead to an expansive 14 x 24 Deck overlooking the amazing level backyard. Additional highlights include a fire pit, brick walkway & a 2 car garage.

15 days
372
41

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 3
Bathrooms: 2
Full bathrooms: 2
Main level bathrooms: 1

Primary bedroom

Features: Bathroom - Full, Cedar Closet(s), Closet, Flooring - Hardwood
Level: First

Bedroom 2

Features: Closet, Flooring - Hardwood
Level: First

Bedroom 3

Features: Closet, Flooring - Hardwood
Level: First

Bathroom 1

Features: Bathroom - Full, Closet - Linen, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Remodeled
Level: Main,First

Bathroom 2

Features: Bathroom - Full, Flooring - Stone/Ceramic Tile, Countertops - Upgraded
Level: Basement

Dining room

Features: Flooring - Hardwood, French Doors, Deck - Exterior, Exterior Access, Open Floorplan
Level: Main,First

Family room

Features: Bathroom - Full, Flooring - Wall to Wall Carpet
Level: Basement

Kitchen

Features: Flooring - Hardwood, Pantry, Countertops - Stone/Granite/Solid, Kitchen Island, Open Floorplan, Recessed Lighting
Level: Main,First

Living room

Features: Flooring - Hardwood, Window(s) - Bay/Bow/Box, Open Floorplan, Recessed Lighting
Level: Main,First

Heating

Electric Baseboard, Electric

Cooling

Window Unit(s)

Appliances

Included: Electric Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer
Laundry: In Basement, Electric Dryer Hookup, Washer Hookup

Features

Central Vacuum
Flooring: Wood, Tile, Carpet, Hardwood
Windows: Insulated Windows, Screens
Basement: Finished,Walk-Out Access,Interior Entry,Garage Access,Concrete
Number of fireplaces: 2
Fireplace features: Family Room, Living Room

Interior area

Total structure area: 2,209
Total interior livable area: 2,209 sqft
Finished area above ground: 1,397
Finished area below ground: 812

Property

Parking

Total spaces: 8
Parking features: Under, Garage Door Opener, Paved Drive, Off Street, Paved
Attached garage spaces: 2
Uncovered spaces: 6

Accessibility

Accessibility features: No

Features

Patio & porch: Deck
Exterior features: Deck, Pool - Inground, Rain Gutters, Screens
Has private pool: Yes
Pool features: In Ground
Frontage length: 150.00

Lot

Size: 0.95 Acres
Features: Cul-De-Sac, Cleared

Details

Foundation area: 1512
Parcel number: M:0340 B:3846 L:0027,1703070
Zoning: SR

Construction

Type & style

Home type: SingleFamily
Architectural style: Split Entry
Property subtype: Single Family Residence

Materials

Frame
Foundation: Concrete Perimeter
Roof: Shingle

Condition

Year built: 1970

Utilities & green energy

Electric: Circuit Breakers
Sewer: Private Sewer
Water: Private
Utilities for property: for Electric Range, for Electric Dryer, Washer Hookup

Community & HOA

Community

Subdivision: Shepard Hills Neighborhood

HOA

Has HOA: No

Location

Region: Sturbridge

Financial & listing details

Price per square foot: $217/sqft
Tax assessed value: $435,100
Annual tax amount: $6,788
Date on market: 9/16/2026
Road surface type: Paved

Estimated market value

$474,000

$450,000 - $498,000

$3,471/mo

Price history

Date	Event	Price
9/26/2026	Contingent	$479,900$217/sqft
Source: MLS PIN #73536696 Report a problem
9/21/2026	Listed for sale	$479,900$217/sqft
Source: MLS PIN #73536696 Report a problem
7/5/2026	Pending sale	$479,900$217/sqft
Source: MLS PIN #73536696 Report a problem
6/26/2026	Listed for sale	$479,900+58.9%$217/sqft
Source: MLS PIN #73536696 Report a problem
11/14/2017	Sold	$302,000+2.4%$137/sqft
Source: Public Record Report a problem
9/20/2017	Listed for sale	$295,000+1.7%$134/sqft
Source: The Greene Realty Group #72231493 Report a problem
11/19/2004	Sold	$290,000$131/sqft
Source: Public Record Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$6,568 +3.7%	$412,300 +7.4%
2024	$6,332 +5.7%	$384,000 +15.8%
2023	$5,992 +14.1%	$331,600 +20.1%
2022	$5,251	$276,100
2021	$5,251	$276,100
2020	$5,251 +3.9%	$276,100 +4.6%
2019	$5,056 +14.6%	$264,000 +16.4%
2018	$4,411 +4.6%	$226,900 +4.4%
2017	$4,216 +1.2%	$217,300 +0.2%
2016	$4,167 +6.2%	$216,900 +6.4%
2015	$3,923 +0.2%	$203,900
2014	$3,915 -3.9%	$203,900 -10.1%
2013	$4,073 -3.1%	$226,900 -4.8%
2012	$4,203 +8.9%	$238,400
2011	$3,860 +7.4%	$238,400 -3.5%
2010	$3,594 +6.6%	$247,000 -7.2%
2009	$3,370 +7.6%	$266,200 -3.8%
2008	$3,133 +5%	$276,800 +1.5%
2007	$2,984 -3.3%	$272,800 +4.4%
2006	$3,085 +7.6%	$261,400 +12.6%
2005	$2,868 -5.2%	$232,200 +43.4%
2004	$3,024 +6.1%	$161,900
2003	$2,851 +12.4%	$161,900 +19.5%
2001	$2,537 +10.6%	$135,500 +1.7%
1997	$2,293	$133,300