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

101 Shepard Rd
Sturbridge, MA 01566

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

$566,700

Trulia Estimate
as of Jul 31, 2026
Est. Refi. Payment $3,552/mo*
Refinance Your Home

$566,700

Trulia Estimate
as of Jul 31, 2026
Est. Refi. Payment $3,552/mo*
Refinance Your Home
4 Beds
3 Baths
2,300 sqft
(on 0.75 acres)

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

Property Type
Single-Family Home
Year Built
1996
Lot Size
0.75 acres
Living Area
2,300 sqft
Price/Sqft
$246
Parking
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. It is currently off market. The Trulia Estimate is $566,700, with a rent estimate of $3,795/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 History for 101 Shepard Rd

DatePriceEventSource
12/18/2020$385,000Sold
EXIT Realty solds #2345676755750373103
08/31/2020$370,000PendingAgent Provided
08/24/2020$370,000Listed For SaleAgent Provided
03/30/2009$260,000Sold
N/A
10/31/2008$269,900Listed For SaleAgent Provided
07/10/1998$176,000Sold
N/A
07/10/1996$136,283Sold
N/A

Market trends in Sturbridge

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
27
6MoM
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Property Tax and Assessment

Year2025
Tax$7,790
Assessment$489,000
Home facts updated by county records

Comparable Sales for 101 Shepard Rd

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
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
42 McGregory Rd, Sturbridge, MA
0.79
Single-Family Home
$572,000
09/05/25
4
2.5
2,049
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
69 Farquhar Rd, Sturbridge, MA
0.71
Single-Family Home
$599,000
03/13/26
4
2.5
2,908

Nearby homes

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Assigned Schools

These are the assigned schools for 101 Shepard Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
    Flag
  • 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!"
    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
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Apartments for Rent

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Explore by feature - Pet Friendly

6 pet-friendly rentals in Sturbridge, MA

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7 rentals with air conditioning in Sturbridge, MA

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8 rentals with a washer/dryer in Sturbridge, MA

Homes for sale near 101 Shepard Rd

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Off Market Homes Near 101 Shepard Rd

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