286 Front St
Winchendon, MA 01475
3 Beds
2 Baths
3,614 sqft (on 1.90 acres)
3 Beds
2 Baths
3,614 sqft
(on 1.90 acres)
Local Information
- Map ViewExplore the area around 286 Front St.
- Schools2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1904
Lot Size
1.9 acres
Living Area
3,614 sqft
Price/Sqft
$120
Parking
Garage
About this House
ONE OF A KIND SINGLE FAMILY HOME: Privacy Galore, Unique Floor Plan, Almost 2 Acres of Land. 1st Level Includes Eat in Kitchen, Dining Room, Living Room & Bedroom with Loft Space/Office, Full Bath, 2nd Bedroom & Laundry Area. Top Level Includes Master Bedroom with Full Bath, Family Room, Storage, Utility Room. LOTS OF SPACE for EVERYONE. Custom Features Include Beamed Ceiling, Custom Cabinets/Storage, Root Cellar, Built-In Book Cases, Multi Level Loft Space, Wood Burning Fireplace. LOVE the 4 CAR GARAGE with Storage and Work Area. LOVE the Private Yard with Garden Area, Plenty of Parking & Surrounded by Trees. First Time on the Market in Over 50+ Years. This Is A Great Place to Call Home, Come See...
286 Front St, Winchendon, MA 01475 is a 3 bedroom, 2 bathroom, 3,614 sqft single-family home built in 1904. It last sold for $275,000 on Nov 3, 2020. It is currently off market. The Trulia Estimate is $433,100, with a rent estimate of $3,203/month.
Home Details for 286 Front St
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Interior Details BasementNumber of Rooms: 9Ceiling Fan |
Heating & Cooling Heating: Forced Air, OilHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 1Floors: Hardwood, Linoleum Vinyl |
Appliances & Utilities Cable ReadyDishwasherRefrigerator |
Fireplace & Spa Fireplace |
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Exterior Home Features Roof: OtherDeckExterior: Stone, Wood, BrickPatioPorch |
Parking & Garage GarageParking Spaces: 4Parking: Garage Attached |
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Year Built Year Built: 1904 |
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional |
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Units in Building: 1 |
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Lot Area: 1.90 acres |
Price History for 286 Front St
| Date | Price | Event | Source |
|---|---|---|---|
| 11/03/2020 | $275,000 | Sold | N/A |
| 08/25/2020 | $249,900 | Pending | Agent Provided |
| 08/13/2020 | $249,900 | Listed For Sale | Agent Provided |
Market trends in Winchendon
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
27
1MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $3,808 |
| Assessment | $324,100 |
Home facts updated by county records
Comparable Sales for 286 Front St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.16 | Single-Family Home | $190,000 | 03/12/26 | 4 | 2 | 3,360 | |
0.18 | Single-Family Home | $406,000 | 09/08/25 | 4 | 2 | 1,700 | |
0.20 | Single-Family Home | $369,900 | 12/04/25 | 3 | 1.5 | 1,344 | |
0.32 | Single-Family Home | $465,000 | 08/29/25 | 3 | 1.5 | 2,494 | |
0.27 | Single-Family Home | $282,000 | 07/10/26 | 2 | 1 | 1,001 | |
0.60 | Single-Family Home | $415,000 | 01/13/26 | 3 | 2.5 | 1,400 | |
0.74 | Single-Family Home | $485,000 | 06/12/26 | 4 | 2 | 2,667 | |
0.60 | Single-Family Home | $455,000 | 09/23/25 | 4 | 2 | 1,668 | |
0.62 | Single-Family Home | $315,000 | 04/09/26 | 4 | 1.5 | 1,868 | |
0.60 | Single-Family Home | $440,000 | 02/06/26 | 3 | 2.5 | 1,400 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
FOR SALENEWOPEN SAT, 10-12PM0.25 ACRESLeanne Roy, Keller Williams Realty North Central
OFF MARKETBrenda Albert, LAER Realty Partners
FOR SALE2.3 ACRESJason Saphire, www.HomeZu.com
OFF MARKETMichelle Peterson, Elm Grove Realty, LLC
OFF MARKETBlock Capital Realty Team, Block Capital Realty LLC
OFF MARKETJohn Keefe, Results Realty
OFF MARKETPowerhouse Team, Keller Williams Realty-Merrimack
SOLDMAR 12, 2026Eugene L. Clements, Clements Realty Group
FOR SALE0.38 ACRESTina Keith, Leading Edge Real Estate
SOLDJAN 16, 2026Michelle Peterson, Elm Grove Realty, LLC
Assigned Schools
These are the assigned schools for 286 Front St.
- Toy Town Elementary School
- 3-5
- Public
- 309 Students
4/10GreatSchools RatingParent Rating AverageThe entire school only cares about kids who have parents that work in the school. Also filthy moldy germ infested.most kids are also Lice infested.Parent Review3y ago - Memorial Elementary School
- K-2
- Public
- 245 Students
NAGreatSchools RatingParent Rating AverageMy son and daughter both have attended this wonderful little gem of a school. They both liked their teachers and were always learning and excited for school- especially excited on P.E. days! The P.e teacher makes learning fun and she does an unbelievable job running the "fun day" at the end of the year. Send your kids here! You won't regret it!Parent Review13y ago - Murdock High School
- 9-12
- Public
- 238 Students
3/10GreatSchools RatingParent Rating Average
No reviews available for this school. - Murdock Middle School
- 6-8
- Public
- 272 Students
5/10GreatSchools RatingParent Rating AverageIf I could give 0 stars I wouldOther Review2y ago 
Check out schools near 286 Front St.
What Locals Say about Winchendon
At least 32 Trulia users voted on each feature.
87 % Say parking is easy
85 % Say it's dog friendly
81 % Say kids play outside
80 % Say car is needed
75 % Say yards are well-kept
74 % Say there's holiday spirit
64 % Say people would walk alone at night
63 % Say it's quiet
59 % Say there are sidewalks
55 % Say neighbors are friendly
50 % Say there's wildlife
50 % Say they plan to stay for at least 5 years
45 % Say streets are well-lit
36 % Say there are community events
34 % Say it's walkable to restaurants
14 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
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Homes for sale near 286 Front St
- 0.38 ACRESTina Keith, Leading Edge Real Estate
0.68 ACRESHometown Team, Real Broker MA, LLC
OFF MARKET
OPEN SAT, 12-3PM1.28 ACRESCory Gracie, LAER Realty Partners
0.36 ACRESMichelle Peterson, Elm Grove Realty, LLC
OPEN SAT, 1-3PM1.25 ACRESDarlene Rossi, Morin Real Estate
FOR SALE BY OWNER0.68 ACRES
See more homes for sale inWinchendon
Off Market Homes Near 286 Front St
SOLDJUL 29, 2026Paul Collette, Keller Williams Realty North Central
SOLDJUL 24, 2026Lisa Saulnier, Keller Williams Realty North Central
SOLDJUL 24, 2026Elizabeth Purdy, DeVries Dolber Realty, LLC
SOLDJUL 23, 2026Piyarat Intachim-Kaufman, Excelsior Realty
SOLDJUL 22, 2026Knox Real Estate Group, William Raveis R.E. & Home Services
SOLDJUL 20, 2026Robert Matewsky, Keller Williams Realty North Central
SOLDJUL 16, 2026Charlotte Marrocco-Mohler, Berkshire Hathaway HomeServices Verani Realty
SOLDJUL 16, 2026Bascom Group, eXp Realty LLC
SOLDJUL 16, 2026Matthew Bodanza, Bodanza Realty LLC- See more homes for sale inWinchendon