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Homes for Sale in Winchendon, MA

18 results

Property at 21 Munroe St, Winchendon, MA 01475
1 / 29
Active Under Contract

$250,000

21 Munroe St, Winchendon, MA 01475

2 bds
|
1 ba
|
808 sqft
MLS® 73563755Single Family Residence
LAER Realty Partners - Olivia Paras
Property at 114 Glenallen Street, Winchendon, MA 01475
1 / 31
Active

$390,000

114 Glenallen Street, Winchendon, MA 01475

4 bds
|
1 ba
|
1802 sqft
MLS® 73563203Single Family Residence
Lamacchia Realty, Inc. - Edwin Ahearn
Property at 142 Pleasant St, Winchendon, MA 01475
1 / 42
Active

$445,000

142 Pleasant St, Winchendon, MA 01475

5 bds
|
2.5 ba
|
2763 sqft
MLS® 73563079Multi Family
Lamacchia Realty, Inc. - Noelle Medugno
Property at 10 Jackson Ave., Winchendon, MA 01475
1 / 32
Active

$325,000

10 Jackson Ave., Winchendon, MA 01475

4 bds
|
2 ba
|
1464 sqft
MLS® 73559752Single Family Residence
Coldwell Banker Realty - Leominster - Kenton Jacobs
Property at 399 Maple St, Winchendon, MA 01475
1 / 29
Active Under Contract

$359,000

399 Maple St, Winchendon, MA 01475

3 bds
|
1 ba
|
1178 sqft
MLS® 73562470Single Family Residence
Coldwell Banker Realty - Leominster - Sara Garcia

What's actually happening in Winchendon right now?

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Property at 263 Front St., Winchendon, MA 01475
1 / 40
Active
Open

$418,000

263 Front St., Winchendon, MA 01475

6 bds
|
2 ba
|
2289 sqft
MLS® 735585122 Family - 2 Units Side by Side
Keller Williams Realty North Central - Leanne Roy
Property at 33 W Shore Drive, Winchendon, MA 01475
1 / 20
Active

$449,000

33 W Shore Drive, Winchendon, MA 01475

3 bds
|
2.5 ba
|
2080 sqft
MLS® 73554607Single Family Residence
Roman Deych - Roman Deych
Property at 179 Front St, Winchendon, MA 01475
1 / 25
Active

$299,000

179 Front St, Winchendon, MA 01475

7 bds
|
4 ba
|
4234 sqft
MLS® 73554552Multi Family
Keller Williams Realty - Merrimack - Blood Team
Property at M-2 L-94 School St, Winchendon, MA 01475
1 / 21
Active

$180,000

M-2 L-94 School St, Winchendon, MA 01475

0 bds
|
0 ba
|
-- sqft
MLS® 73545020Other
RE/MAX Town Square - Vicki Christiansen
Property at 90 Royalston Rd N, Winchendon, MA 01475
1 / 42
Active
Price

$599,900

90 Royalston Rd N, Winchendon, MA 01475

3 bds
|
2.5 ba
|
1828 sqft
MLS® 73544803Single Family Residence
Tessa Parziale Real Estate - Tessa Parziale Rigattieri
Property at 101 Royalston Rd N, Winchendon, MA 01475
1 / 42
Active Under Contract

$600,000

101 Royalston Rd N, Winchendon, MA 01475

3 bds
|
1.5 ba
|
1992 sqft
MLS® 73541111Single Family Residence
EXIT New Options Real Estate - Laura Rice
Property at 5 Island Rd, Winchendon, MA 01475
1 / 27
Active
Price

$625,000

5 Island Rd, Winchendon, MA 01475

3 bds
|
2 ba
|
1624 sqft
MLS® 73540320Single Family Residence
Karin Anderson Real Estate LLC - Karin Anderson
Property at 155 River St, Winchendon, MA 01475
1 / 36
Active
Price

$454,000

155 River St, Winchendon, MA 01475

5 bds
|
3 ba
|
2075 sqft
MLS® 73530513Single Family Residence
Leading Edge Real Estate - Tina Keith
Property at 6 Loon Road, Winchendon, MA 01475
1 / 35
Active
Price

$539,000

6 Loon Road, Winchendon, MA 01475

3 bds
|
2.5 ba
|
1924 sqft
MLS® 73520335Single Family Residence
LAER Realty Partners - Cory Gracie
Property at 0 Lot 2 Stoddard Rd, Winchendon, MA 01475
1 / 8
Active
Price

$130,000

0 Lot 2 Stoddard Rd, Winchendon, MA 01475

0 bds
|
0 ba
|
-- sqft
MLS® 73522930Residential
Keller Williams Realty North Central - Team Molet
Property at 10-12 School Sq., Winchendon, MA 01368
1 / 17
Active

$659,000

10-12 School Sq., Winchendon, MA 01368

10 bds
|
4 ba
|
3818 sqft
MLS® 735001664 Family
www.HomeZu.com - Jason Saphire
Property at 0 Mellen Rd, Winchendon, MA 01475
1 / 6
Active
Price

$110,000

0 Mellen Rd, Winchendon, MA 01475

0 bds
|
0 ba
|
-- sqft
MLS® 73491734Residential
LAER Realty Partners - Kristen Dodge
Property at 16 Maple Place B, Winchendon, MA 01475
1 / 15
Active
Price

$309,900

16 Maple Place B, Winchendon, MA 01475

3 bds
|
1 ba
|
1340 sqft
MLS® 73461917Single Family Residence
Cameron Real Estate Group - Bob Devito

Brokerage Information

Gundersheim Group Real Estate

10 Lincoln St, Newton, MA, 02461

(617) 997-8272

Market Area Served

Boston, Brookline, Needham, Newton, Wellesley, Somerville and many more.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Data last updated: 8/17/2026 at 1:12:00 PM

Melanie Gundersheim

Buy or sell in Boston, Newton, Needham, Brookline, Wellesley, and Somerville with clear guidance, local insight, and a calm, strategic process.

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  • 10 Lincoln St, Newton, MA, 02461
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© 2026 Melanie Gundersheim. All rights reserved.
Equal Housing Opportunity. Information deemed reliable but not guaranteed.