Recently Viewed Properties
See This Home
Save This Listing
Close

$230,000

  • Sold
  • Closed
  • Commercial Investment
See This Home
Save This Home
See This Home
Save This Home
The Winchester Building is one the most iconic properties in downtown Winchester. Exceptional opportunity to own a mixed-use commercial building with first floor retail and two apartments above. Situated in the heart of town, the building currently has a successful short-term rental investment residence. Close proximity to Keene to the north and Massachusetts and the I-91 corridor to the south.

Full Property Details for 144 Main St

General

  • Sold For: $230,000
  • Taxes: $3,320 (2023)
  • Status: Closed
  • Type: Commercial Investment
  • Source: PrimeMLS
  • MLS ID: 5021165
  • Added to Site: 436 day(s) ago

Parking

  • Parking: On Street

Location

  • County: Cheshire

Utilities

  • Sewer: Public

Structural Information

  • Basement Entrance: Interior
  • Basement Desc.: Unfinished
  • Square Feet: 2,080
  • Year Built: 1887

Unit Information

  • Units in Building: 3

Lot Features

  • Lot Size (Acres): 0.03
  • Lot Size (Sq. Ft.): 1,307
  • Frontage: Yes Road Frontage
  • Frontage Feet: 77
  • Zoning: Central Business District

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Type: River
  • Water Front Name: Yes
  • Water Front Shared: 1

Financial Considerations

  • Price Per Sq. Ft.: $110.58
  • Tax Amount: $3,320
  • Tax Year: 2023

Listed and Sold by RE/MAX Town & Country, Vincent Dolan

Listed and Sold by RE/MAX Town & Country, Vincent Dolan

Listing agent

— 144 Main St —

  • Vincent Dolan

    RE/MAX Town & Country

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 144 Main St

School District:Winchester School District, Winchester, NH
NameGradesDistance
Winchester School
85 Parker Street, Winchester, NH 03470
PK-80.5 mi
Keene High School
43 Arch Street, Keene, NH 03431
9-1212 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 144 Main St

Date
Details
Price
Change
Source
7/28/2025
Sold
$230,000
-8%
MLS
4/02/2025
Price Reduced
$250,000
-12.28%
MLS
11/05/2024
Listed
$285,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed and Sold by RE/MAX Town & Country, Vincent Dolan

Just Listed near 144 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

182 Main Rd, Gill, MA 01354 - Photo 1 Just Listed
$539,000

182 Main Rd  Gill, MA 01354

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,856
    Sq. Ft.
10 Center Rd, Gill, MA 01354 - Photo 1 Just Listed
$259,900
Open House

10 Center Rd  Gill, MA 01354

  • Single Family
  • Active
  • Updated 2 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 936
    Sq. Ft.
0 State Rd, Erving, MA 01344 - Photo 1 Just Listed
$250,000

0 State Rd  Erving, MA 01344

  • Lots/Land
  • Active
  • Updated 5 hours ago
  • 6.71
    Acres
43 Winchendon Rd, Royalston, MA 01368 - Photo 1 Just Listed
$349,900

43 Winchendon Rd  Royalston, MA 01368

  • Single Family
  • Active
  • Updated 2 days ago
  • 5
    Beds
  • 2
    Total Baths
  • 3,112
    Sq. Ft.

Price Reduced near 144 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

12 Todd Hl Rd, Hinsdale, NH 03451 - Photo 1 Price Reduced
-$74,000 (-18.55%)
$325,000

12 Todd Hl Rd  Hinsdale, NH 03451

  • Single Family
  • Active
  • Updated 1 day ago
  • 5
    Beds
  • 4
    Total Baths
  • 3,128
    Sq. Ft.
Listed by RE/MAX Town & Country
Lots 1-4 North St, Erving, MA 01344 - Photo 1 Price Reduced
-$50,000 (-15.38%)
$275,000

Lots 1-4 North St  Erving, MA 01344

  • Land Residential
  • Active
  • Updated 3 days ago
  • 20.07
    Acres
4 Elm Ave, Royalston, MA 01368 - Photo 1 Price Reduced
-$25,100 (-3.72%)
$649,900
Open House

4 Elm Ave  Royalston, MA 01368

  • Single Family
  • Active
  • Updated 5 hours ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,481
    Sq. Ft.
62 E Main St, Erving, MA 01344 - Photo 1 Price Reduced
-$10,000 (-3.85%)
$249,900
Open House

62 E Main St  Erving, MA 01344

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,219
    Sq. Ft.

Recent Sales near 144 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

100 Main St, Winchester, NH 03470 - Photo 1 Sold
$202,500

100 Main St  Winchester, NH 03470

  • Multi-Family
  • Closed
  • 2
    Units
  • 0.06
    Acres
Listed by RE/MAX Town & Country
Sold by The Neighborhood Realty Group
102 Keene Rd, Winchester, NH 03470 - Photo 1 Sold
$218,500

102 Keene Rd  Winchester, NH 03470

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 3,603
    Sq. Ft.
Listed by BHG Masiello Keene
Sold by Brattleboro Area Realty
128 Keene Rd, Winchester, NH 03470 - Photo 1 Sold
$225,000

128 Keene Rd  Winchester, NH 03470

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,320
    Sq. Ft.
Listed by BHG Masiello Keene
Sold by Duston Leddy Real Estate
12 Miner Ct, Winchester, NH 03470 - Photo 1 Sold
$259,000

12 Miner Ct  Winchester, NH 03470

  • Single Family
  • Closed
  • 3
    Beds
  • 1
    Total Bath
  • 1,416
    Sq. Ft.
Listed by BHG Masiello Keene
Sold by Greenwald Realty Group

144 Main Street, Winchester, NH 03470 (MLS# 5021165) is a Commercial Investment property that was sold at $230,000 on July 28, 2025. Want to learn more about 144 Main Street? Do you have questions about finding other Commercial Investment real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.