39 Hillside Dr, Sturbridge, MA 01566
Property image
Property image
FOR SALE
1.05 ACRES

$599,900

Original price: $624,900
  • 4 Beds
  • 2.5 Baths
  • 2,851 sqft (on 1.05 acres)

39 Hillside Dr, Sturbridge, MA 01566

Est. Mortgage $3,884/mo*
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Home Highlights

Single-Family Home
Built in 1987
1.05 acre lot
$210/sqft
2 Car Garage

Local Information

  • Map ViewExplore the area around 39 Hillside Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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!
Last check for updates: about 6 hours ago
Listing courtesy of Jim Black Group, (314) 325-6474
Real Broker MA, LLC, (508) 365-3532
Richard Jenkins, (774) 243-2110
Source: MLS PIN, MLS#73520572
Also Listed on MLS PIN.

Home Details for 39 Hillside Dr

Interior Features

Interior Details
Basement: Full,Partially Finished,Walk-Out Access,Interior Entry,ConcreteNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2851 Square Feet
Appliances & Utilities
Utilities: for Electric Range, for Electric Oven, for Electric Dryer, Icemaker ConnectionAppliances: Water Heater, Range, Dishwasher, Microwave, Plumbed For Ice MakerDishwasherLaundry: Flooring - Stone/Ceramic Tile,First Floor,Electric Dryer HookupMicrowave
Heating & Cooling
Heating: Baseboard,Oil,Electric,WoodNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Living RoomHas a FireplaceNo Spa
Gas & Electric
Electric: Circuit Breakers, 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Insulated WindowsDoor: Insulated Doors, Storm Door(s)Flooring: Tile, Carpet, Hardwood, Flooring - Wall to Wall Carpet
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood, Flooring Wall To Wall Carpet
View
Has a ViewView: Scenic View(s)

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Deck - WoodExterior: Deck - Wood, Rain Gutters, GardenFoundation: Concrete PerimeterGarden
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Attached,Garage Door Opener,Storage,Garage Faces Side,Off Street,Paved
Frontage
Waterfront: Lake/Pond, Unknown To Beach, Beach Ownership(Private)Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadNot on Waterfront
Water & Sewer
Sewer: Private Sewer
Finished Area
Finished Area (above surface): 2272Finished Area (below surface): 579

Days on Market

Days on Market: 125

Property Information

Year Built
Year Built: 1987
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Not Included in Sale: Washer, Dryer And RefrigeratorParcel Number: M:340 B:000 L:3856039, 1703078

Price & Status

Price
List Price: $599,900Price Per Sqft: $210

Active Status

MLS Status: Active

Location

Direction & Address
City: SturbridgeCommunity: Westville

Agent Information

Listing Agent
Listing ID: 73520572

Building

Building Area
Building Area: 2851 Square Feet

Community

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

HOA

No HOA

Lot Information

Lot Area: 1.05 Acres

Energy

Energy Efficiency Features: Thermostat

Miscellaneous

BasementMls Number: 73520572Above Grade Unfinished Area: 2272

Additional Information

ShoppingPoolTennis Court(s)ParkWalk/Jog TrailsStable(s)GolfMedical FacilityConservation AreaHighway AccessHouse of WorshipPublic School

Around this home

What Locals Say about Sturbridge

At least 52 Trulia users voted on each feature.

  • 94 % Say car is needed

  • 88 % Say parking is easy

  • 83 % Say there's holiday spirit

  • 82 % Say it's dog friendly

  • 79 % Say yards are well-kept

  • 75 % Say it's quiet

  • 72 % Say there's wildlife

  • 67 % Say people would walk alone at night

  • 61 % Say kids play outside

  • 52 % Say they plan to stay for at least 5 years

  • 51 % Say neighbors are friendly

  • 44 % Say streets are well-lit

  • 38 % Say there are community events

  • 35 % Say it's walkable to restaurants

  • 28 % Say there are sidewalks

  • 25 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Pbbw9dhf4k
    "Farmers markets and social family events. Fun competitions. Music bingo. Trivia nights. Holiday events. "
    0
    Flag
  • Jim Meskauskas
    "You have to drive everywhere. There is no public transportation. I also work from home. There’s nothing else to say."
    0
    Flag
  • James Esterbrook
    "It’s an upper middle class area where people have pets and they walk them….nothing more, nothing less."
    0
    Flag
  • Betsy L.
    "Good town to raise kids in, school system is top notch. Been here for 25 years, never regretted our decision to move here."
    0
    Flag
  • Jfclancey
    "Excellent highway access. Can get to the Pike and i-84 in minutes. Easy to get to Hartford, Worcester, Marlboro, Boston and Springfield. "
    2
    Flag
  • Eyren L.
    "Very quiet, but close to the highway for the commuters. No public transportation beyond school buses, which isn't good for anyone who doesn't drive. Mainly restaurants and hotels are what keep the town thriving, but there are some great hole in the wall shops."
    2
    Flag
  • James E.
    "I love living here, moving here was one of the best decisions I’ve made. Great schools, restaurants, sense of community and lots of young families moving to the area. Excellent amenities like farmers market, farms, outdoor recreation spaces..... "
    0
    Flag
  • Jfgannon1
    "I don’t commute anymore. Work from home. Is an ideal location, though, at the junction of 2 interstate highways, 1US Route 20, SR 131."
    0
    Flag
  • Eva G.
    "Farmers market every Sunday on the Common during the Summer through early Fall. Senior Center on Main Street is well organized and offers daily exercise classes at minimal cost, linch everyday and a fantastic newsletter which outlines the month’s events."
    0
    Flag
  • Jfgannon1
    "Friendly families. Cup d sac. Well maintained yards. Rural. Wildlife abounds. Children in the neighborhood."
    0
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  • Elizabethlouisepotter
    "There’s a dance studio and a paint-and-sip. The school district is competitive and well-run. Great commuter town."
    0
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  • Carrina G.
    "Great school, and friendly people. Lots of walking trails. And amazing restaurants. And lots of history "
    1
    Flag
  • Carrina G.
    "Not much Francisco during the day. But a little bit of Traffic during morning and afternoon hours. Busses can be an issue during commute to work. "
    0
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  • Robert d.
    "Great restaurants. Extremely high taxes and very business unfriendly community. I think maintaining a high tax rate with little to no business opportunities helps to ensure that only the right type of demographic lives here!"
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  • Robert d.
    "Incredibly high taxes & a generally snobby attitude from most of the townspeople. The town is not at all business friendly."
    0
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  • skiross
    "This area, known as Walker Pond, is an "association" development centered on one side of a lake with a state park on the other side. The neighborhood is the greatest around for several reasons. The association dues are approx. $200/year and includes resident use of two beaches with playground equipment for children, boat docks, dedicated swimming areas, volleyball, a ball field, tennis courts, and a horse stable. The area has approx 125 homes and is extremely safe for chidren playing outside. (Cars do not pass through to get to anywhere else.) It is a wonderful family neighborhood! The association is also quite active with 4th of July events, lobster bakes, children's Christmas parties and last day of school picnics, neighborhood yard sales, etc. It is quiet, idyllic, friendly, and happy!"
    0
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Market trends in Sturbridge

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
38
9MoM

Home Value

Trulia Estimate
$596K
Since last month
Increased$7K (+1.2%)
Since last year
Increased$22K (+3.8%)
Since last sale
Increased$404K (+210.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +86% in the last 10 years
MonthEstimated value
2026
September 2026$596K
August 2026$589K
July 2026$614K
June 2026$661K
May 2026$670K
April 2026$625K
March 2026$613K
February 2026$595K
January 2026$589K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
8 Shepard Pl, Sturbridge, MA
0.33
Single-Family Home
$545,000
10/27/25
3
1.5
2,160
7 Orchard Rd, Sturbridge, MA
0.39
Single-Family Home
$487,500
11/21/25
3
2.5
2,607
6 Hillside Dr, Sturbridge, MA
0.28
Single-Family Home
$555,000
10/29/25
3
2
2,263
10 Orchard Rd, Sturbridge, MA
0.38
Single-Family Home
$595,000
12/12/25
4
3.5
2,388
170 Shepard Rd, Sturbridge, MA
0.31
Single-Family Home
$435,000
09/03/26
3
3
2,300
89 River Rd, Sturbridge, MA
0.49
Single-Family Home
$474,900
12/18/25
3
3
1,840
45 River Rd, Sturbridge, MA
0.74
Single-Family Home
$685,000
07/10/26
4
2.5
2,652
107 Wallace Rd, Sturbridge, MA
0.56
Single-Family Home
$455,000
02/20/26
3
2
2,237
18 South Rd, Sturbridge, MA
0.68
Single-Family Home
$600,000
10/16/25
3
2.5
2,404
69 Farquhar Rd, Sturbridge, MA
0.92
Single-Family Home
$599,000
03/13/26
4
2.5
2,908

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
50 Hillside Dr, Sturbridge, MA 01566
0.23
$1,075,000
4
2.5
2,688
For Sale
7 Shepard Pl, Sturbridge, MA 01566
0.28
$407,700
3
1
1,250
Off Market
6 Hillside Dr, Sturbridge, MA 01566
0.28
$571,500
3
2
2,263
Off Market
170 Shepard Rd, Sturbridge, MA 01566
0.31
$435,000
3
3
2,300
Recently Sold
8 Shepard Pl, Sturbridge, MA 01566
0.33
$561,300
3
1.5
2,160
Off Market
16-18 Curboy Rd, Sturbridge, MA 01566
0.35
$495,000
2
1
1,196
For Sale
10 Orchard Rd, Sturbridge, MA 01566
0.38
$595,000
4
3.5
2,388
Recently Sold
7 Orchard Rd, Sturbridge, MA 01566
0.39
$487,500
3
2.5
2,607
Recently Sold
108 Mashapaug Rd, Sturbridge, MA 01566
0.47
$475,900
3
2.5
1,822
Off Market
89 River Rd, Sturbridge, MA 01566
0.49
$474,900
3
3
1,840
Recently Sold
112 Mashapaug Rd, Sturbridge, MA 01566
0.50
$484,300
3
1.5
1,998
Off Market

Price and Tax history

DateEventPrice
Aug 12, 2026
Source: MLS PIN #73520572
PriceChange
$599,900
Price decreased by 4%
Jul 11, 2026
Source: MLS PIN #73520572
PendingToActive
$624,900
Jul 1, 2026
Source: MLS PIN #73520572
Contingent
$644,900
Jun 8, 2026
Source: MLS PIN #73520572
PriceChange
$644,900
Price decreased by 1%
May 18, 2026
Source: MLS PIN #73520572
Listed For Sale
$649,900

LGBTQ Local Legal Protections

Jim Black Group, Real Broker MA, LLC, (508) 365-3532
Agent Phone: (314) 325-6474
The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

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Frequently asked questions about 39 Hillside Dr

  • What is the estimated monthly payment for 39 Hillside Dr?
    Based on a $599,900 list price with 20% down at today's rates, the estimated monthly payment for 39 Hillside Dr in Sturbridge, MA is approximately $3,970 (about $3,285 principal & interest, $610 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Sturbridge?
    Residents describe Sturbridge, MA as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See homes for sale in Sturbridge, MA.
  • What are the closest schools to 39 Hillside Dr?
    The closest schools to 39 Hillside Dr in Sturbridge, MA are Burgess Elementary School (Pre-K, rated 7/10), Tantasqua Regional Jr High School (rated 5/10), Tantasqua Regional Sr High School (rated 8/10).
  • What is 39 Hillside Dr estimated to be worth?
    Trulia's estimated value for 39 Hillside Dr in Sturbridge, MA is $596,000.
  • Does 39 Hillside Dr have a pool?
    Yes, 39 Hillside Dr in Sturbridge, MA has a pool.
  • Does 39 Hillside Dr have laundry facilities?
    Yes, 39 Hillside Dr in Sturbridge, MA has laundry facilities.
39 Hillside Dr, Sturbridge, MA 01566 is a 4 bedroom, 3 bathroom, 2,851 sqft single-family home built in 1987. This property is currently available for sale and was listed by MLS PIN on May 18, 2026. The MLS # for this home is MLS# 73520572.