66 Shepard Rd, Sturbridge, MA 01566
OFF MARKET

$483,100

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,814 sqft (on 0.37 acres)

66 Shepard Rd, Sturbridge, MA 01566

Est. Refi. Payment $3,155/mo*
Refinance Your Home
Currently Off Market - Sold Mar 23, 2016 for $215,000

Home Value

Trulia Estimate
$483K
Since last month
Increased$2K (+0.3%)
Since last year
Increased$21K (+4.4%)
Since last sale
Increased$268K (+124.7%)
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 +120% in the last 10 years
MonthEstimated value
2026
September 2026$483K
August 2026$481K
July 2026$488K
June 2026$491K
May 2026$484K
April 2026$483K
March 2026$477K
February 2026$469K
January 2026$458K
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
64 Shepard Rd, Sturbridge, MA
0.02
Single-Family Home
$220,000
11/18/25
3
1
2,042
71 Shepard Rd, Sturbridge, MA
0.07
Single-Family Home
$260,000
09/21/26
3
1
1,069
6 Hillside Dr, Sturbridge, MA
0.42
Single-Family Home
$555,000
10/29/25
3
2
2,263
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
0.28
Single-Family Home
$487,500
11/21/25
3
2.5
2,607
8 Blueberry Ln, Sturbridge, MA
0.57
Single-Family Home
$545,000
03/12/26
4
2
2,367
10 Blueberry Ln, Sturbridge, MA
0.56
Single-Family Home
$600,000
06/29/26
4
3
2,040
10 Orchard Rd, Sturbridge, MA
0.28
Single-Family Home
$595,000
12/12/25
4
3.5
2,388
1 Leslie Ln, Sturbridge, MA
0.65
Single-Family Home
$425,000
12/31/25
3
1
1,341
170 Shepard Rd, Sturbridge, MA
0.74
Single-Family Home
$435,000
09/03/26
3
3
2,300

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
71 Shepard Rd, Sturbridge, MA 01566
0.07
$260,000
3
1
1,069
Recently Sold
85 Shepard Rd, Sturbridge, MA 01566
0.16
$354,900
2
1
816
Off Market
47 Shepard Rd, Sturbridge, MA 01566
0.16
$389,800
3
1
1,112
Off Market
10 Orchard Rd, Sturbridge, MA 01566
0.28
$595,000
4
3.5
2,388
Recently Sold
7 Orchard Rd, Sturbridge, MA 01566
0.28
$501,000
3
2.5
2,607
Off Market
8 Shepard Pl, Sturbridge, MA 01566
0.33
$561,300
3
1.5
2,160
Off Market
5 Fairview Park Rd #10, Sturbridge, MA 01566
0.34
$231,300
2
1
800
Off Market
5 Fairview Park Rd #12, Sturbridge, MA 01566
0.34
$256,100
2
1
800
Off Market
6 Fairview Park Rd, Sturbridge, MA 01566
0.36
$396,600
2
1
1,344
Off Market
7 Shepard Pl, Sturbridge, MA 01566
0.39
$409,100
3
1
1,250
Off Market
3 Gedeon Ave, Sturbridge, MA 01566
0.38
$441,300
4
2
1,980
Off Market
6 Plimpton Ave, Sturbridge, MA 01566
0.40
$396,700
3
1.5
1,120
Off Market

Local Information

  • Map ViewExplore the area around 66 Shepard Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1957
0.37 acre lot
1,814 sqft
$266/sqft

About this House

Extensively remodeled home is ready for you to move right in! Gorgeous new kitchen with new granite countertops and the latest tiled backsplash. You love the new cabinets and stainless steel appliances! New washer & dryer now included! Formal dining room and living room are open and sunny. There are two bedrooms with hardwood floors on the first floor and the master suite is the entire second floor. It has vaulted ceilings and it's own brand new bath! The basement has high ceilings and is a walk-out right to the back yard. There are kitchen cabinets here so it's ready for you to convert it to a summer kitchen or a workshop. Wait until you see the backyard! It is wide open for possibilities. The new septic system is in and makes for a level play area. The owners have diligently upgraded this home so it is an easy choice for you. Its so quiet here you won't believe how close it is to stores! Immediate close is possible. Drive in garage with basement access.
66 Shepard Rd, Sturbridge, MA 01566 is a 3 bedroom, 2 bathroom, 1,814 sqft single-family home built in 1957. It last sold for $215,000 on Mar 23, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $483,100, with a rent estimate of $3,492/month.

Home Details for 66 Shepard Rd

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: OilHeating Fuel: Oil

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other

Property Information

Year Built
Year Built: 1957
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.37 acres

Price and Tax history

DateEventPrice
Mar 23, 2016
Source: N/A
Sold
$215,000
Jan 29, 2016
Source: Agent Provided
Pending
$219,900
Nov 29, 2015
Source: Agent Provided
PriceChange
$219,900
Price decreased by 4%
Oct 5, 2015
Source: Agent Provided
PriceChange
$229,900
Price decreased by 4%
Jul 22, 2015
Source: Agent Provided
PriceChange
$239,900
Price decreased by 3%

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
    Flag
  • Jfgannon1
    "Friendly families. Cup d sac. Well maintained yards. Rural. Wildlife abounds. Children in the neighborhood."
    0
    Flag
  • 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
    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
    Flag
  • Robert d.
    "Incredibly high taxes & a generally snobby attitude from most of the townspeople. The town is not at all business friendly."
    0
    Flag
  • 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 66 Shepard Rd

  • What is 66 Shepard Rd estimated to be worth?
    Trulia's estimated value for 66 Shepard Rd in Sturbridge, MA is $483,100.
  • What is the price history for 66 Shepard Rd?
    66 Shepard Rd in Sturbridge, MA last sold for $215,000 in March 2016.
  • 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 66 Shepard Rd?
    The lot at 66 Shepard Rd in Sturbridge, MA is about 0.37 acres (16,117 sq ft).

Explore by feature - Air Conditioning

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