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$377,500 -$2,400 (-0.63%) Price Reduced

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 1 Full Bath
  • 1 Partial Bath
  • 2,128 Sq. Ft.
  • 0.26 Acres
  • 2 Car Garage
  • Updated 1 day ago
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WELL LOVED AND CARED FOR FAMILY HOME JUST 15 MINUTES FROM ROUTE 2! This gorgeous colonial holds 100+ years of beautiful memories and history. There is original woodwork that features bulls-eye molding through out the house. The first floor features a spacious eat-in kitchen, newer stainless steel appliances, cozy pantry, laundry room &1/2 bath-all freshly painted. A large mudroom off the kitchen offers extra storage. Open, Sun-filled living & dining room with beautiful hardwood & built in cabinets. Office off the dining room/kitchen leads into the impressive foyer with extra wide staircase original molding, & stain glass window. Upstairs features 3 charming,freshly painted & carpeted bedrooms with plenty of walk in closet space. New 30 year roof in 2019, new gutters and freshly painted side deck.The detached oversize, 2 car garage has new insulated, steel doors and a 30 year roof replaced in 2023. Located on a quiet side street. Close to schools, shopping, parks and downtown.

Full Property Details for 29 Winter St

General

  • Price: $377,500
  • Taxes: $4,470 (2025)
  • Status: Active
  • Type: Single Family
  • MLS ID: 73455962
  • Updated: 1/14/2026
  • Added to Site: 58 day(s) ago

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 1
  • Half Bathrooms: 1
  • Bathroom 1: Second
  • Bathroom 2: First

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: 14.00 x 14.00, Second
  • Bedroom 2: 13.00 x 11.00, Second
  • Bedroom 3: Second

Other Rooms

  • Living Room: 16.00 x 14.00, First
  • Family Room: 14.00 x 13.00, Main, First
  • Kitchen: 17.00 x 12.00, First
  • Dining Room: 17.00 x 14.00, Main, First

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking Features: Detached, Off Street

Location

  • County: Worcester

Structural Information

  • Architectural Style: Colonial
  • Basement: Yes
  • Square Feet: 2,128
  • Year Built: 1914

Lot Features

  • Lot Size (Acres): 0.26

Financial Considerations

  • Tax Amount: $4,470
  • Tax Year: 2025

Disclosures and Reports

  • Disclosures/Rstr.: Main house roof is 6 years & garage is 2. Both have a 30 year warranty.
  • Property ID: M:5A3 B:0 L:49, 3493743

Listed by Tammy Morrison Real Estate, Tammy C. Morrison

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Listing agent

— 29 Winter St —

  • Tammy C. Morrison

    Tammy Morrison Real Estate

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 29 Winter St

School District:Winchendon School District
NameGradesDistance
Memorial Elementary School, Winchendon, MA
32 Elmwood Road, Winchendon, MA 01475
K-20.4 mi
Toy Town Elementary School
175 Grove Street, Winchendon, MA 01475
3-50.6 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 29 Winter St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/10/2026
Price Reduced
$377,500
-0.63%
MLS
11/18/2025
Listed
$379,900
295.73%
MLS
7/15/1998
Sold
$96,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 29 Winter St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,470
5%
$380,400
12%
2024
$4,275
-5%
$340,900
2%
2023
$4,490
10%
$335,100
24%
2022
$4,071
12%
$269,400
16%
2021
$3,636
3%
$231,300
6%
2020
$3,541
6%
$217,500
9%
2019
$3,332
7%
$199,400
11%
2018
$3,109
10%
$179,200
14%
2017
$2,830
3%
$157,500
—
2016
$2,756
4%
$158,100
—
2015
$2,643
7%
$158,100
2%
2014
$2,479
—
$155,300
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 29 Winter St

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Tammy Morrison Real Estate, Tammy C. Morrison

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29 Winter St, Winchendon, MA 01475 (MLS# 73455962) is a Single Family property with 3 bedrooms, 1 full bathroom and 1 partial bathroom. 29 Winter St is currently listed for $377,500 and was received on November 18, 2025. Want to learn more about 29 Winter St? Do you have questions about finding other Single Family real estate for sale in Winchendon? You can browse all Winchendon real estate or contact a Coldwell Banker agent to request more information.

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