21 Cheapside St, Greenfield, MA 01301
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Property image
OFF MARKET

21 Cheapside St
Greenfield, MA 01301

  • 2 Beds
  • 1 Bath
  • 1,500 sqft (on 0.50 acres)

$296,900

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $1,914/mo*
Refinance Your Home

$296,900

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $1,914/mo*
Refinance Your Home
2 Beds
1 Bath
1,500 sqft
(on 0.50 acres)

Home Value

Trulia Estimate
$297K
Since last month
Increased$200 (+0.1%)
Since last year
Increased$5K (+1.5%)
Since last sale
Increased$73K (+32.2%)
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 +166% in the last 10 years
MonthEstimated value
2026
August 2026$298K
July 2026$297K
June 2026$301K
May 2026$302K
April 2026$297K
March 2026$293K
February 2026$289K
January 2026$284K
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
298 Deerfield St, Greenfield, MA
0.60
Single-Family Home
$220,000
12/17/25
3
1
1,216
221 Hope St, Greenfield, MA
0.52
Single-Family Home
$244,000
10/09/25
3
2
1,480
109 Montague City Rd, Greenfield, MA
0.59
Single-Family Home
$389,000
01/09/26
3
1.5
1,454
71 Washington St, Greenfield, MA
0.73
Single-Family Home
$227,000
06/17/26
2
1
887
62 Peabody Ln, Greenfield, MA
0.44
Single-Family Home
$510,000
05/14/26
3
1.5
1,700
73 Washington St, Greenfield, MA
0.72
Single-Family Home
$139,900
06/29/26
2
1
843
292 Deerfield St, Greenfield, MA
0.62
Single-Family Home
$280,000
09/16/25
4
1.5
1,369
44 Russell St, Greenfield, MA
0.80
Single-Family Home
$160,000
10/10/25
2
2
1,280
227 Deerfield St, Greenfield, MA
0.73
Single-Family Home
$160,000
01/23/26
3
2
1,496
407 Montague City Rd, Turners falls, MA
0.98
Single-Family Home
$327,000
08/29/25
3
1
1,550

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
427-429 Deerfield St, Greenfield, MA 01301
0.15
$195,000
4
2
2,668
For Sale
44 Briar Way #44, Greenfield, MA 01301
0.29
$267,800
2
1.5
1,152
Off Market
81 Briar Way, Greenfield, MA 01301
0.35
$295,000
2
1.5
1,127
For Sale
194 Briar Way #194, Greenfield, MA 01301
0.39
-
2
2
1,152
Off Market
250-252 Hope St, Greenfield, MA 01301
0.40
-
6
5
2,536
Off Market
62 Peabody Ln, Greenfield, MA 01301
0.44
$510,000
3
1.5
1,700
Recently Sold
255 Briar Way #255, Greenfield, MA 01301
0.47
-
2
1.5
1,132
Off Market
231 Hope St, Greenfield, MA 01301
0.48
$364,600
4
2
1,664
Off Market
332 Deerfield St, Greenfield, MA 01301
0.49
$318,800
4
2
1,582
Off Market
10 Southern Ave, Greenfield, MA 01301
0.51
$280,600
2
1
1,082
Off Market
221 Hope St, Greenfield, MA 01301
0.52
$256,400
3
2
1,480
Off Market
122 James St, Greenfield, MA 01301
0.54
$281,400
4
1
1,669
Off Market

Local Information

  • Map ViewExplore the area around 21 Cheapside St.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1790
Lot Size
0.5 acres
Living Area
1,500 sqft
Price/Sqft
$198
Parking
Garage

About this House

This single-family home is located at 21 Cheapside St, Greenfield, MA. 21 Cheapside St is in Greenfield, MA and in ZIP code 01301. This property has 2 bedrooms, 1 bathroom and approximately 1,500 sqft of floor space. This property has a lot size of 0.50 acres and was built in 1790.
21 Cheapside St, Greenfield, MA 01301 is a 2 bedroom, 1 bathroom, 1,500 sqft single-family home built in 1790. It last sold for $225,000 on Sep 17, 2021. It is currently off market. The Trulia Estimate is $296,900, with a rent estimate of $2,196/month.

Home Details for 21 Cheapside St

Interior Features

Interior Details
BasementAtticNumber of Rooms: 6Types of Rooms: WorkshopCeiling Fan
Heating & Cooling
Heating: Oil, Wood PelletHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood, Laminate
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: MetalExterior: WoodLawnPatio
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1790
Property Type / Style
Property Type: Single Family HomeArchitecture: cottage

Community

Units in Building: 1

Lot Information

Lot Area: 0.50 acres

Price and Tax history

DateEventPrice
Jan 31, 2023
Source: MLS PIN #73063811
ListingRemoved
$249,900
Dec 8, 2022
Source: MLS PIN #73063811
Listed For Sale
$249,900
Sep 17, 2021
Source: MLS PIN #72869861
Sold
$225,000
Aug 9, 2013
Source: N/A
Sold
$100,000
Feb 25, 2005
Source: N/A
Sold
$5,000

Market trends in Greenfield

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
24
5MoM

Around this home

What Locals Say about Greenfield

At least 90 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 86 % Say parking is easy

  • 82 % Say car is needed

  • 82 % Say yards are well-kept

  • 79 % Say there are sidewalks

  • 77 % Say people would walk alone at night

  • 74 % Say kids play outside

  • 72 % Say there's wildlife

  • 69 % Say there's holiday spirit

  • 66 % Say it's walkable to restaurants

  • 64 % Say streets are well-lit

  • 63 % Say they plan to stay for at least 5 years

  • 61 % Say neighbors are friendly

  • 49 % Say it's quiet

  • 46 % Say it's walkable to grocery stores

  • 31 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • 9w49nts5bg
    "Just a great place to live "
    0
    Flag
  • Pete Smith
    "It’s a great dog neighborhood—lots of people with pups, great walking routes including through highland park. "
    0
    Flag
  • James Shultis
    "Inclusive, family oriented community with lots of different things to do (live music, block parties, restaurants, a beautiful library, and more)! "
    0
    Flag
  • Davepays
    "Large yards, Well lit sidewalks, parks with poop bags and receptacles, nice local trails, plenty of dogs around"
    2
    Flag
  • Kasha D.
    "We, moved in 2013 . We, love it. Our neighbors became our close friends our kids play together all the time. Lots of kids on our street. We, have a mini “green monsta “ ball field to make it look like the one Boston across our street. "
    3
    Flag
  • Jessyknorr
    "it's a family/pet friendly hometown. I would recommend this town over most other towns near this area."
    0
    Flag
  • Desiree S.
    "Winter carnival and franklin county fair. Along with other events that is put on through the year including 4th of July event of fireworks."
    3
    Flag
  • JosieB
    "It's filled with helpful and kind people. I always have someone I can turn to here. It's beautiful and there is a lot to do. Hawks and Reed in particular is an amazing spot for live music."
    1
    Flag
  • Davepays
    "Always people waking dogs in the neighborhood. Trash cans and poop bag dispensers at the local parks."
    0
    Flag
  • Mae T.
    "I see people frequently walking their dogs around. I do not personally own a dog but I do see that people have them and enjoy having their pets in public areas. "
    0
    Flag
  • Barbarajeancurzi
    "I've lived here for 7 years... Came here from Boston... and I love it! It's a great combination of friendliness and privacy, enough space between houses to let You do Your own thing, but not so much that one feels lonely or afraid of being out in the woods too far. Yet we get to see the beauty of nature all around us all the time! The hills (that I call mountains!😉), lots of rivers and beautiful bridges that when one crosses, one can't help but be captured by the amazing views... It's just lovely... The air is good, People are friendly, there's access to great music and cultural events, huge variety of educational resources nearby, creative Fairs of many kinds, access to tons of fresh, healthy, affordable foods, great neighborhood eateries, surprisingly good health care, and all within a short ride which is practically traffic-free, especially if compared to City traffic. There's a wide variety of Peoples, many with a common thread of extreme decency and a caring attitude toward the immediate community, as well as the World Community. I love it here! "
    0
    Flag
  • Charlie H.
    "This area is out of town just far enough to gave good sized yards a safe feeling. But you can be downtown in just a few minutes. Just rural enough. We do not have any public transit out here, but it is a quick trip to Big Y, Staples or Home Depot. We have lots of kids around as well. "
    0
    Flag
  • Alaine B.
    "though there are no "dog parks" we do have other parks for dogs and owners to play in. sidewalks on almost all streets make it easy to walk your dog anywhere. "
    0
    Flag
  • Abigail C.
    "Depending on where you live in town, the traffic can be pretty annoying at times. Just watch out at heavy traffic times. I’ve seen people rip up and down the street plenty of times going way too fast. "
    0
    Flag
  • RoRoTotts
    "We have a safe, quiet neighborhood with an annual neighborhood tag sale and concerts! Greenfield has events for children and adults throughout the year and is a vibrant and upcoming community!"
    1
    Flag
  • Roseeferrari
    "We have a neighborhood tag sale every other year. As a town we have the Franklin County Fair. Every year there is a winter carnival and local businesses sponsor ice sculptures along Main Street. We have two weekly farmers markets. Free community events, such as Dinofest and trunk or treat, happen year round. All this and so much more make agree field a wonderful community to live in! "
    2
    Flag
  • Davepays
    "It’s culturally diverse with a mix of owner occupied and rental units. I have some excellent neighbors and some really wacky ones."
    1
    Flag
  • Alaine B.
    "it's close enough to walk to beacon field, the hospital or downtown, which is ridiculous to pay to park in."
    0
    Flag
  • barbcurzi
    "I moved to Greenfield just over two years ago and really love it. There is a great combination of People of all ages and many varied and unique backgrounds, with encouraging access to Community and Educational opportunities, with an emphasis on Health and Wellness as well as Justice and Caring. There is also a lively World of Music and The Arts. The bright stars at night and the constant views of Nature's Magnificence by day, make it a place never to tire of. The easy access to all amenities and necessities is a wonder, when combined with its Natural Beauty. There are a variety of places to buy locally grown and organic foods at affordable and sometimes, great prices. There is nothing to complain about except that recycling is collected every two weeks instead of weekly!! (I will be working on that :) Great place to live and the value of my house is already more than two times what I paid for it two years ... I Love it here in Greenfield!"
    2
    Flag
  • Shawn K.
    "Greenfield is fantastic town on the verge of becoming a center piece of Western Massachusetts. With easy access to Vermont recreation, local biking fishing hiking and water sports. The Deerfield River and Connecticut River are minutes from my door. The new County Court House and Hospital will be ready in no time. Greenfield is host to the GreenRiver Festival of Music and this year will star Nora Jones. Most importantly there are the best private schools in the country right at your door step with Deerfield Academy, Northfield Mountain Herman, and amazing elementary schools like the world reknown Greenfield Center School. Research it yourself and see how my little house could be a great place to be in the heart of everything for just pennys on the dollar. The five Colleges are just 30 minutes away, Hartford, Boston, New York, Cape Cod just a few hours drive. You can't beat it... "
    0
    Flag
  • Helen
    "neighborhood needs to be cleaned up junk yard across the street"
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 21 Cheapside St

  • What is 21 Cheapside St estimated to be worth?
    Trulia's estimated value for 21 Cheapside St in Greenfield, MA is $296,900.
  • What is the price history for 21 Cheapside St?
    21 Cheapside St in Greenfield, MA last sold for $225,000 in September 2021.
  • Is Greenfield a buyer's or seller's market?
    Greenfield is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Greenfield?
    Residents describe Greenfield, MA as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Greenfield, MA.
  • Does 21 Cheapside St have laundry facilities?
    Yes, 21 Cheapside St in Greenfield, MA has in-unit laundry.
  • How big is the lot at 21 Cheapside St?
    The lot at 21 Cheapside St in Greenfield, MA is about 0.50 acres (21,567 sq ft).

Explore by feature - Air Conditioning

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