21 Simpson St, Sturbridge, MA 01566
Property image
Property image
OFF MARKET

$428,100

Trulia Estimate
  • 3 Beds
  • 1 Bath
  • 1,248 sqft (on 0.31 acres)

21 Simpson St, Sturbridge, MA 01566

Est. Refi. Payment $2,675/mo*
Refinance Your Home
Currently Off Market - Sold Dec 24, 2020 for $302,000

Home Value

Trulia Estimate
$428K
Since last month
Decreased$8K (-1.8%)
Since last year
Increased$20K (+5%)
Since last sale
Increased$125K (+41.5%)
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 +139% in the last 10 years
MonthEstimated value
2026
August 2026$427K
August 2026$427K
July 2026$435K
June 2026$436K
May 2026$431K
April 2026$429K
March 2026$421K
February 2026$416K
January 2026$405K
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
1 Leslie Ln, Sturbridge, MA
0.33
Single-Family Home
$425,000
12/31/25
3
1
1,341
64 Shepard Rd, Sturbridge, MA
0.44
Single-Family Home
$220,000
11/18/25
3
1
2,042
75 Fairview Park Rd, Sturbridge, MA
0.34
Single-Family Home
$412,000
07/07/26
2
1
1,404
86 Old Sturbridge Rd, Southbridge, MA
0.76
Single-Family Home
$395,000
02/27/26
3
1
1,232
52 Crestwood Dr, Southbridge, MA
0.70
Single-Family Home
$270,000
08/17/26
3
1
840
26 Roosevelt Dr, Southbridge, MA
0.79
Single-Family Home
$380,000
05/07/26
3
1
1,244
57 Old Sturbridge Rd, Southbridge, MA
0.81
Single-Family Home
$319,900
04/24/26
4
1
1,664
85 Idlewood St, Southbridge, MA
0.62
Single-Family Home
$378,500
06/02/26
3
2
1,092
38 Glenwood Ave, Southbridge, MA
0.73
Single-Family Home
$395,000
11/19/25
3
2
1,960
6 Berry Farms Rd #2, Sturbridge, MA
0.51
Single-Family Home
$441,700
09/18/25
2
2
1,493

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
6 Plimpton Ave, Sturbridge, MA 01566
0.05
$397,400
3
1.5
1,120
Off Market
3 Gedeon Ave, Sturbridge, MA 01566
0.07
$442,600
4
2
1,980
Off Market
6 Fairview Park Rd, Sturbridge, MA 01566
0.10
$396,600
2
1
1,344
Off Market
42 Fairview Park Rd, Sturbridge, MA 01566
0.07
$533,600
4
2.5
1,938
Off Market
5 Fairview Park Rd #10, Sturbridge, MA 01566
0.12
$224,298
2
1
800
Recently Sold
5 Fairview Park Rd #12, Sturbridge, MA 01566
0.12
$256,100
2
1
800
Off Market
16 Gedeon Ave, Sturbridge, MA 01566
0.10
$522,100
3
2
2,162
Off Market
3 Newton Pl, Sturbridge, MA 01566
0.12
$529,100
3
3
1,534
Off Market
7 McGregory Rd, Sturbridge, MA 01566
0.14
$556,100
4
2
2,400
Off Market
21 McGregory Rd, Sturbridge, MA 01566
0.21
$610,300
3
1.5
2,210
Off Market
42 McGregory Rd, Sturbridge, MA 01566
0.23
$592,200
4
2.5
2,049
Off Market
6 Wallace Rd, Sturbridge, MA 01566
0.28
$438,700
3
1.5
1,678
Off Market

Local Information

  • Map ViewExplore the area around 21 Simpson St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1956
Lot Size
0.31 acres
Living Area
1,248 sqft
Price/Sqft
$343
Parking
Garage

About this House

Move in and relax in this beautiful, well-maintained ranch-style home with many newer updates on a quiet Sturbridge Street. Gorgeous maple cabinets, quartz countertops, new LifeProof floor in kitchen, an updated bathroom, lots of closet space, and beautiful hardwood floors. Buderus furnace, new oil tank, and newer roof and windows. Relax with your morning coffee or tea in your peaceful screen-in porch or your sun-filled living room. The large walkout basement offers tons of storage, and is heated with its own zone, just waiting to be finished. A great yard for entertaining with a fire pit, lots of privacy, and a second driveway leading to a shed/workshop. Great commuter location; just minutes from major highways - Mass pike, Rt. 84 and Rt. 20. Sought after Tantasqua/Burgess school system! This house won't last.
21 Simpson St, Sturbridge, MA 01566 is a 3 bedroom, 1 bathroom, 1,248 sqft single-family home built in 1956. It last sold for $302,000 on Dec 24, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $428,100, with a rent estimate of $2,827/month.

Home Details for 21 Simpson St

Interior Features

Interior Details
BasementNumber of Rooms: 5Ceiling Fan
Heating & Cooling
Heating: Baseboard, OilHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Concrete, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Stone, VinylPorch
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1956
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.31 acres

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Dec 24, 2020
Source: N/A
Sold
$302,000
Nov 5, 2020
Source: Agent Provided
Pending
$279,900
Oct 29, 2020
Source: Agent Provided
Listed For Sale
$279,900
Dec 24, 2012
Source: Agent Provided
ListingRemoved
$229,800
Dec 1, 2012
Source: Agent Provided
PriceChange
$229,800
Price decreased by 0%

Market trends in Sturbridge

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
29
2MoM

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 21 Simpson St

  • What is 21 Simpson St estimated to be worth?
    Trulia's estimated value for 21 Simpson St in Sturbridge, MA is $428,100.
  • What is the price history for 21 Simpson St?
    21 Simpson St in Sturbridge, MA last sold for $302,000 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.
  • Does 21 Simpson St have laundry facilities?
    Yes, 21 Simpson St in Sturbridge, MA has in-unit laundry.
  • How big is the lot at 21 Simpson St?
    The lot at 21 Simpson St in Sturbridge, MA is about 0.31 acres (13,503 sq ft).

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