$644,900
PENDING $5K PRICE DROP

39 Hillside Dr Sturbridge, MA 01566

Estimated payment $4,128/month

Total Views 3,629
4 Beds
2.5 Baths
2,851 Sq Ft
$226 Price per Sq Ft

Highlights

  • Community Stables
  • Medical Services
  • Scenic Views
  • Burgess Elementary School Rated A-
  • Property is near a beach
  • Open Floorplan

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!

Listing Agent

James Black

Real Broker MA, LLC Listed on: 05/18/2026

Real Broker MA, LLC

Co-Listing Agent

Richard Jenkins

Real Broker MA, LLC

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $7,978

Year Built

  • Built in 1987 | Remodeled

Lot Details

  • 1.05 Acre Lot
  • Cul-De-Sac
  • Level Lot
  • Cleared Lot
  • Garden

Parking

  • 2 Car Attached Garage
  • Parking Storage or Cabinetry
  • Side Facing Garage
  • Garage Door Opener
  • 4 Open Parking Spaces
  • Off-Street Parking

Home Design

  • Colonial Architecture
  • Frame Construction
  • Shingle Roof
  • Concrete Perimeter Foundation

Interior Spaces

  • Open Floorplan
  • Ceiling Fan
  • Insulated Windows
  • Insulated Doors
  • Living Room with Fireplace
  • Game Room
  • Scenic Vista Views
  • Storm Doors

Kitchen

  • Breakfast Bar
  • Range
  • Microwave
  • Plumbed For Ice Maker
  • Dishwasher
  • Solid Surface Countertops

Flooring

  • Wood
  • Wall to Wall Carpet
  • Ceramic Tile

Bedrooms and Bathrooms

  • 4 Bedrooms
  • Primary bedroom located on second floor
  • Walk-In Closet
  • Bathtub with Shower
  • Separate Shower
  • Linen Closet In Bathroom

Laundry

  • Laundry on main level
  • Electric Dryer Hookup

Partially Finished Basement

  • Walk-Out Basement
  • Basement Fills Entire Space Under The House
  • Interior Basement Entry

Outdoor Features

  • Property is near a beach
  • Balcony
  • Deck
  • Rain Gutters

Utilities

  • No Cooling
  • Wood Insert Heater
  • 3 Heating Zones
  • Heating System Uses Oil
  • Baseboard Heating
  • 200+ Amp Service
  • Private Water Source
  • Water Heater
  • Private Sewer

Additional Features

  • Energy-Efficient Thermostat
  • Property is near golf course and schools

Listing and Financial Details

  • Assessor Parcel Number M:340 B:000 L:3856039,1703078

Community Details

Overview

  • No Home Owners Association
  • Near Conservation Area

Amenities

  • Medical Services
  • Shops

Recreation

  • Tennis Courts
  • Community Pool
  • Park
  • Community Stables
  • Jogging Path

Home Details

Home Type

Single Family

Est. Annual Taxes

$7,978

Year Built

Built in 1987 | Remodeled

Lot Details

1.05 Acres

Parking

2

Listing Details

  • Property Type: Residential
  • Property Sub Type: Single Family Residence
  • Architectural Style: Colonial
  • Year Built: 1987
  • Year Built Details: Actual
  • Year Round: Yes
  • MLSPIN_ADU: N
  • MLSPIN_BEACHFRONT_FLAG: Yes
  • Special Features: None

Interior Features

  • Flooring: Tile, Carpet, Hardwood, Flooring - Wall to Wall Carpet
  • Interior Amenities: Closet, Game Room
  • Door Features: Insulated Doors, Storm Door(s)
  • Fireplace Features: Living Room
  • Fireplace YN: Yes
  • Fireplaces: 1
  • Appliances: Water Heater, Range, Dishwasher, Microwave, Plumbed For Ice Maker
  • Total Bedrooms: 4
  • Room Bedroom2 Level: Second
  • Room Bedroom2 Features: Closet, Flooring - Wall to Wall Carpet
  • Room Bedroom3 Features: Closet, Flooring - Wall to Wall Carpet
  • Room Bedroom3 Level: Second
  • Room Bedroom4 Level: Second
  • Room Bedroom4 Features: Closet, Flooring - Wall to Wall Carpet
  • Basement YN: Yes
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Total Bathrooms: 3
  • Room Master Bedroom Features: Bathroom - Full, Ceiling Fan(s), Walk-In Closet(s), Flooring - Wall to Wall Carpet
  • Room Master Bedroom Level: Second
  • Master Bathroom Features: Yes
  • Bathroom 1 Features: Bathroom - Full, Bathroom - With Shower Stall, Closet - Linen, Flooring - Stone/Ceramic Tile
  • Bathroom 1 Level: Second
  • Bathroom 2 Level: Second
  • Bathroom 2 Features: Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Remodeled
  • Bathroom 3 Features: Bathroom - Half, Closet, Flooring - Stone/Ceramic Tile
  • Bathroom 3 Level: First
  • Room Dining Room Features: Flooring - Hardwood
  • Room Dining Room Level: First
  • Room Family Room Level: First
  • Room Family Room Features: Flooring - Hardwood, Open Floorplan
  • Room Kitchen Level: First
  • Room Kitchen Features: Flooring - Stone/Ceramic Tile, Balcony / Deck, Countertops - Stone/Granite/Solid, Breakfast Bar / Nook, Exterior Access, Open Floorplan
  • Laundry Features: Flooring - Stone/Ceramic Tile, First Floor, Electric Dryer Hookup
  • Room Living Room Level: First
  • Room Living Room Features: Flooring - Hardwood, Open Floorplan
  • Basement: Full, Partially Finished, Walk-Out Access, Interior Entry, Concrete
  • Above Grade Finished Sq Ft: 2272
  • Below Grade Sq Ft: 579
  • Living Area: 2851
  • Spa YN: No
  • Window Features: Insulated Windows
  • MAIN LO: AN4866
  • Insulation: Full

Exterior Features

  • Exterior Features: Deck - Wood, Rain Gutters, Garden
  • Construction Materials: Frame
  • Foundation Details: Concrete Perimeter
  • Home Warranty YN: No
  • Patio And Porch Features: Deck - Wood
  • Road Frontage Type: Public
  • Roof: Shingle
  • View: Scenic View(s)
  • View YN: Yes
  • Waterfront Features: Lake/Pond, Unknown To Beach, Beach Ownership(Private)
  • Waterfront YN: No

Garage/Parking

  • Garage Spaces: 2
  • Attached Garage YN: Yes
  • Carport Y N: No
  • Covered Parking Spaces: 2
  • Garage YN: Yes
  • Open Parking Spaces: 4
  • Open Parking YN: Yes
  • Parking Features: Attached, Garage Door Opener, Storage, Garage Faces Side, Off Street, Paved
  • Total Parking Spaces: 6

Utilities

  • Sewer: Private Sewer
  • Utilities: for Electric Range, for Electric Oven, for Electric Dryer, Icemaker Connection
  • Cooling: None
  • Heating: Baseboard, Oil, Electric, Wood
  • Cooling Y N: No
  • Electric: Circuit Breakers, 200+ Amp Service
  • Heating YN: Yes
  • Water Source: Private
  • HEAT ZONES: 3
  • COOLING ZONES: 0

Condo/Co-op/Association

  • Association YN: No
  • Community Features: Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Conservation Area, Highway Access, House of Worship, Public School
  • Senior Community YN: No

Lot Info

  • Parcel Number: M:340 B:000 L:3856039,1703078
  • Zoning: .
  • Farm Land Area Units: Square Feet
  • Lot Features: Cul-De-Sac, Cleared, Level
  • Lot Size Acres: 1.05
  • Lot Size Sq Ft: 45738
  • Lot Size Units: Acres
  • Property Attached YN: No

Green Features

  • Green Energy Efficient: Thermostat

Tax Info

  • Tax Year: 2025
  • Tax Annual Amount: 7978

Multi Family

  • Basement Included Sq Ft: Yes

Map

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
Collateral Analytics

Collateral Analytics Collateral Analytics AVMs (Automated Valuation Model) employ a number of statistical approaches combined with neighborhood-specific comparable selection guarantees the most up-to-date and precise valuations.

Not Available

Collateral Analytics does not have data for the current month. Please view the chart for historical values.

ICE

ICE Mortgage Technology ICE Mortgage Technology’s AVM (Automated Valuation Model) is a state-of-the-art online residential property valuation tool that provides a quick and accurate estimate of the value of almost any home in the U.S.

Not Available

ICE Mortgage Technology does not have data for the current month. Please view the chart for historical values.

First American

First American First American Data & Analytics’ next-generation AVM combines unrivaled data assets with a blended ensemble of valuation models to produce highly accurate, reliable valuations you can trust.

Not Available

First American does not have data for the current month. Please view the chart for historical values.

Quantarium

Quantarium Quantarium’s valuation service, repeatedly proven the industry’s most accurate and comprehensive, is supercharged with a self-learning and auto-tuning AI engine that continually becomes smarter and more accurate as it processes daily inputs from the industry’s leading RE data lake.

Not Available

Quantarium does not have data for the current month. Please view the chart for historical values.

Average Value
Not Available
List Price
Sold Price
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area

Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $7,978 $500,800 $105,800 $395,000
2024 $7,825 $474,500 $103,700 $370,800
2023 $7,595 $420,300 $90,000 $330,300
2022 $7,304 $381,400 $81,300 $300,100
2021 $6,655 $349,900 $77,500 $272,400
2020 $6,655 $349,900 $77,500 $272,400
2019 $6,358 $332,000 $79,700 $252,300
2018 $6,264 $322,200 $75,900 $246,300
2017 $5,997 $309,100 $73,200 $235,900
2016 $5,744 $299,000 $71,000 $228,000
2015 $5,703 $296,400 $71,000 $225,400
Source: Public Records

Property History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft
07/01/2026 07/01/26 Pending -- -- --
06/08/2026 06/08/26 Price Changed $644,900 -0.8% $226 / Sq Ft
05/18/2026 05/18/26 For Sale $649,900 -- $228 / Sq Ft
Source: MLS Property Information Network (MLS PIN)

Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Type Sale Price Title Company
Deed $192,000 --
Deed $189,000 --
Deed $220,000 --
Source: Public Records

Mortgage History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Status Loan Amount Loan Type
Open $240,000 No Value Available
Closed $177,000 Purchase Money Mortgage
Previous Owner $148,000 No Value Available
Source: Public Records

Source: MLS Property Information Network (MLS PIN)

MLS Number: 73520572

MLS Property Information Network (MLS PIN)

APN: STUR-000340-000000-003856-000039

Your Personal Tour Guide

Ask me questions while you tour the home.