101 Shepard Rd, Sturbridge, MA 01566
Property image
Property image
OFF MARKET

$554,300

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,300 sqft (on 0.75 acres)

101 Shepard Rd, Sturbridge, MA 01566

Est. Refi. Payment $3,610/mo*
Refinance Your Home
Currently Off Market - Sold Dec 18, 2020 for $385,000

Home Value

Trulia Estimate
$554K
Since last month
Decreased$4K (-0.8%)
Since last year
Increased$23K (+4.4%)
Since last sale
Increased$169K (+43.8%)
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$554K
August 2026$558K
July 2026$564K
June 2026$570K
May 2026$564K
April 2026$565K
March 2026$556K
February 2026$546K
January 2026$536K
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
7 Orchard Rd, Sturbridge, MA
0.16
Single-Family Home
$487,500
11/21/25
3
2.5
2,607
10 Orchard Rd, Sturbridge, MA
0.10
Single-Family Home
$595,000
12/12/25
4
3.5
2,388
8 Shepard Pl, Sturbridge, MA
0.08
Single-Family Home
$545,000
10/27/25
3
1.5
2,160
6 Hillside Dr, Sturbridge, MA
0.24
Single-Family Home
$555,000
10/29/25
3
2
2,263
170 Shepard Rd, Sturbridge, MA
0.43
Single-Family Home
$435,000
09/03/26
3
3
2,300
107 Wallace Rd, Sturbridge, MA
0.61
Single-Family Home
$455,000
02/20/26
3
2
2,237
45 River Rd, Sturbridge, MA
0.63
Single-Family Home
$685,000
07/10/26
4
2.5
2,652
64 Shepard Rd, Sturbridge, MA
0.34
Single-Family Home
$220,000
11/18/25
3
1
2,042
89 River Rd, Sturbridge, MA
0.67
Single-Family Home
$474,900
12/18/25
3
3
1,840
71 Shepard Rd, Sturbridge, MA
0.26
Single-Family Home
$260,000
09/21/26
3
1
1,069

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
8 Shepard Pl, Sturbridge, MA 01566
0.08
$561,300
3
1.5
2,160
Off Market
10 Orchard Rd, Sturbridge, MA 01566
0.10
$595,000
4
3.5
2,388
Recently Sold
7 Shepard Pl, Sturbridge, MA 01566
0.12
$409,100
3
1
1,250
Off Market
7 Orchard Rd, Sturbridge, MA 01566
0.16
$501,000
3
2.5
2,607
Off Market
85 Shepard Rd, Sturbridge, MA 01566
0.15
$354,900
2
1
816
Off Market
6 Hillside Dr, Sturbridge, MA 01566
0.24
$571,500
3
2
2,263
Off Market
71 Shepard Rd, Sturbridge, MA 01566
0.26
$260,000
3
1
1,069
Recently Sold
27 Hillside Dr, Sturbridge, MA 01566
0.30
$479,900
3
2
2,209
For Sale
39 Hillside Dr, Sturbridge, MA 01566
0.38
$599,900
4
2.5
2,851
For Sale
170 Shepard Rd, Sturbridge, MA 01566
0.43
$435,000
3
3
2,300
Recently Sold
36 Wallace Rd, Sturbridge, MA 01566
0.42
$299,100
2
1
1,248
Off Market
47 Shepard Rd, Sturbridge, MA 01566
0.46
$389,800
3
1
1,112
Off Market

Local Information

  • Map ViewExplore the area around 101 Shepard Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1996
0.75 acre lot
2,300 sqft
$241/sqft
Garage

About this House

HIGHEST & BEST BY 5pm 8/30/20 - STUNNING open contemporary cape with 4 bedrooms (3 on first floor) & 3 full baths. Vaulted ceilings in dining & living area with deep built-ins and wood burning fireplace, hardwood floors throughout, tons of natural lighting. Master bedroom and master bath on first floor, private loft area for in-home office and 4th bedroom upstairs. Country kitchen with lots of counter space, breakfast bar, tile floor and stainless appliances. Finished walk-out basement with family room, office, exercise room and full bath. Slider off living room to nice size deck overlooking large flat private back yard. 1 car attached garage and cute farmer's porch on front. Conveniently located close to all the shopping conveniences and major routes yet hidden away set back from the road in a tranquil location. Passing title v in hand, nicely landscaped with mature plantings. Possible in-law or 5th bedroom in finished basement. Subject to sellers finding suitable housing.
101 Shepard Rd, Sturbridge, MA 01566 is a 4 bedroom, 3 bathroom, 2,300 sqft single-family home built in 1996. It last sold for $385,000 on Dec 18, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $554,300, with a rent estimate of $3,846/month.

Home Details for 101 Shepard Rd

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: Baseboard, Electric, OilHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood, Laminate
Appliances & Utilities
DishwasherRefrigerator

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Vinyl
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.75 acres

Price and Tax history

DateEventPrice
Dec 18, 2020
Source: EXIT Realty solds #2345676755750373103
Sold
$385,000
Aug 31, 2020
Source: Agent Provided
Pending
$370,000
Aug 24, 2020
Source: Agent Provided
Listed For Sale
$370,000
Mar 30, 2009
Source: N/A
Sold
$260,000
Oct 31, 2008
Source: Agent Provided
Listed For Sale
$269,900

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

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
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  • 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
    Flag
  • 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!"
    0
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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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 101 Shepard Rd

  • What is 101 Shepard Rd estimated to be worth?
    Trulia's estimated value for 101 Shepard Rd in Sturbridge, MA is $554,300.
  • What is the price history for 101 Shepard Rd?
    101 Shepard Rd in Sturbridge, MA last sold for $385,000 in December 2020.
  • Is Sturbridge a buyer's or seller's market?
    Sturbridge is currently a seller's market, based on recent for-sale activity.
  • 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 recently sold homes in Sturbridge, MA.
  • How big is the lot at 101 Shepard Rd?
    The lot at 101 Shepard Rd in Sturbridge, MA is about 0.75 acres (32,670 sq ft).
  • Does 101 Shepard Rd have a garage?
    Yes, 101 Shepard Rd in Sturbridge, MA has a garage.

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