Real Estate for Sale

Browse all available properties in Winchester, MA and surrounding towns
(Lexington, Lincoln, Arlington, Belmont, Weston, Watertown).
Find your perfect home with our comprehensive listings and smart filters

Currently 342 properties in our database.

Last updated: July 14, 2025 at 01:40 PM

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18 Belknap Street Unit 2 - Winchester Real Estate

$1,249,900 -  Condominium

18 Belknap Street Unit 2 - Arlington, 02474

4 beds • 4.5 baths • 2,100 sqft

MLS ID: 73397474

Agent: O'Connor

Office: Berkshire Hathaway HomeServices Commonwealth Real Estate

837 Massachusetts Ave Unit 1 - Winchester Real Estate

$598,000 -  Condominium

837 Massachusetts Ave Unit 1 - Lexington, 02420

2 beds • 2 baths • 1,044 sqft

MLS ID: 73397422

Agent: Savage

Office: Berkshire Hathaway HomeServices Commonwealth Real Estate

1468 Massachusetts Ave - Winchester Real Estate

$1,535,000 -  Single Family Home

1468 Massachusetts Ave - Lexington, 02420

4 beds • 2.5 baths • 3,204 sqft

MLS ID: 73397196

Agent: The Murphy Group Lexington

Office: William Raveis R.E. & Home Services

225 Mystic St - Winchester Real Estate

$799,000 -  Single Family Home

225 Mystic St - Arlington, 02474

2 beds • 1 baths • 1,064 sqft

MLS ID: 73396405

Agent: Steve McKenna & The Home Advantage Team

Office: Gibson Sotheby's International Realty

131 Coolidge Ave. Unit 621 - Winchester Real Estate

$629,900 -  Condominium

131 Coolidge Ave. Unit 621 - Watertown, 02472

1 beds • 1 baths • 850 sqft

MLS ID: 73395996

Agent: Christine Norcross & Partners

Office: William Raveis R.E. & Home Services

16 Field Rd Unit 16 - Winchester Real Estate

$849,000 -  Condominium

16 Field Rd Unit 16 - Arlington, 02476

3 beds • 2 baths • 1,587 sqft

MLS ID: 73395751

Agent: Ryerson-Greeley

Office: Gibson Sotheby's International Realty

11 Nichols Road - Winchester Real Estate

$1,485,000 -  Single Family Home

11 Nichols Road - Lexington, 02420

4 beds • 3.5 baths • 2,627 sqft

MLS ID: 73395494

Agent: The Murphy Group Lexington

Office: William Raveis R.E. & Home Services

34 Lewis Ave Unit 34 - Winchester Real Estate

$1,200,000 -  Condominium

34 Lewis Ave Unit 34 - Arlington, 02474

4 beds • 2.5 baths • 2,748 sqft

MLS ID: 73394089

Agent: New England's Finest Real Estate Group

Office: Real Broker MA, LLC

65 Blake Rd - Winchester Real Estate

$1,995,000 -  Single Family Home

65 Blake Rd - Lexington, 02420

4 beds • 2.5 baths • 3,650 sqft

MLS ID: 73394050

Agent: The LIV Group

Office: Berkshire Hathaway HomeServices Commonwealth Real Estate

338 Forest St - Winchester Real Estate

$895,000 -  Single Family Home

338 Forest St - Arlington, 02474

3 beds • 2 baths • 1,691 sqft

MLS ID: 73393867

Agent: Steve McKenna & The Home Advantage Team

Office: Gibson Sotheby's International Realty

196 Old River Rd Unit 147 - Winchester Real Estate

$279,900 -  Condominium

196 Old River Rd Unit 147 - Lincoln, 02865

2 beds • 1 baths • 1,090 sqft

MLS ID: 73393244

Agent: Spectrum Real Estate Consultants

Office: Keller Williams Realty Leading Edge

24 Constitution Road - Winchester Real Estate

$1,980,000 -  Single Family Home

24 Constitution Road - Lexington, 02421

5 beds • 3.5 baths • 3,628 sqft

MLS ID: 73393184

Agent: Beth Sager Group

Office: Keller Williams Realty Boston Northwest

1437 Massachusetts Ave - Winchester Real Estate

$895,000 -  Single Family Home

1437 Massachusetts Ave - Lexington, 02420

3 beds • 1 baths • 1,212 sqft

MLS ID: 73393131

Agent: Savage

Office: Berkshire Hathaway HomeServices Commonwealth Real Estate

2 Third Street - Winchester Real Estate

$349,900 -  Single Family Home

2 Third Street - Belmont, 03220

2 beds • 1.5 baths • 1,120 sqft

MLS ID: 73390610

Agent: Gendron

Office: Berkshire Hathaway HomeServices Verani Realty

58 Aldrich Rd Unit A - Winchester Real Estate

$489,500 -  Condominium

58 Aldrich Rd Unit A - Watertown, 02472

2 beds • 1 baths • 744 sqft

MLS ID: 73390026

Agent: The Madden Team

Office: Keller Williams Realty Boston Northwest

14 Reiling Pond Rd - Winchester Real Estate

$3,195,000 -  Single Family Home

14 Reiling Pond Rd - Lincoln, 01773

5 beds • 5 baths • 8,066 sqft

MLS ID: 73389487

Agent: The Sarkis Team

Office: Douglas Elliman Real Estate - The Sarkis Team

14 Percy Rd - Winchester Real Estate

$3,650,000 -  Single Family Home

14 Percy Rd - Lexington, 02421

7 beds • 5 baths • 8,577 sqft

MLS ID: 73389244

Agent: The Kelleher Spalding Team

Office: Gibson Sotheby's International Realty

7 Broad St - Winchester Real Estate

$1,089,000 -  Single Family Home

7 Broad St - Belmont, 02478

3 beds • 1 baths • 1,153 sqft

MLS ID: 73389213

Agent: Jim & Mike Savas Team

Office: Berkshire Hathaway HomeServices Commonwealth Real Estate

342 Payson Rd - Winchester Real Estate

$1,625,000 -  Single Family Home

342 Payson Rd - Belmont, 02478

3 beds • 3.5 baths • 2,876 sqft

MLS ID: 73389209

Agent: Jim & Mike Savas Team

Office: Berkshire Hathaway HomeServices Commonwealth Real Estate

418 Mystic St - Winchester Real Estate

$1,795,000 -  Single Family Home

418 Mystic St - Arlington, 02474

4 beds • 4 baths • 3,446 sqft

MLS ID: 73388302

Agent: The North Star Group

Office: Keller Williams Realty Evolution

10 Williams Unit 39 - Winchester Real Estate

$449,000 -  Condominium

10 Williams Unit 39 - Watertown, 02472

2 beds • 1 baths • 950 sqft

MLS ID: 73381927

Agent: DelRose McShane Team

Office: Coldwell Banker Realty - Belmont

164 Galen St Unit 65 - Winchester Real Estate

$449,000 -  Condominium

164 Galen St Unit 65 - Watertown, 02472

2 beds • 1 baths • 950 sqft

MLS ID: 73381921

Agent: DelRose McShane Team

Office: Coldwell Banker Realty - Belmont

56 Marlboro St Unit 1 - Winchester Real Estate

$650,000 -  Condominium

56 Marlboro St Unit 1 - Belmont, 02478

2 beds • 1 baths • 1,049 sqft

MLS ID: 73378639

Agent: The Paradigm Team

Office: Coldwell Banker Realty - Newton

5 Walnut Street - Winchester Real Estate

$2,648,000 -  Single Family Home

5 Walnut Street - Lexington, 02421

5 beds • 4 baths • 5,198 sqft

MLS ID: 73378336

Agent: The Carter Team

Office: Barrett Sotheby's International Realty

52 Greenridge Ln Unit 52 - Winchester Real Estate

$574,000 -  Condominium

52 Greenridge Ln Unit 52 - Lincoln, 01773

2 beds • 1 baths • 990 sqft

MLS ID: 73377999

Agent: Middleman

Office: Berkshire Hathaway HomeServices Warren Residential

11 Windermere Park - Winchester Real Estate

$1,439,000 -  Single Family Home

11 Windermere Park - Arlington, 02476

4 beds • 2.5 baths • 2,070 sqft

MLS ID: 73377572

Agent: Steve McKenna & The Home Advantage Team

Office: Gibson Sotheby's International Realty

18 Belknap St Unit 3 - Winchester Real Estate

$1,349,000 -  Condominium

18 Belknap St Unit 3 - Arlington, 02474

4 beds • 4.5 baths • 2,145 sqft

MLS ID: 73376513

Agent: O'Connor

Office: Berkshire Hathaway HomeServices Commonwealth Real Estate

47 Mystic St Unit 4E - Winchester Real Estate

$475,000 -  Condominium

47 Mystic St Unit 4E - Arlington, 02474

2 beds • 1 baths • 850 sqft

MLS ID: 73375977

Agent: Scalisi

Office: CJL Rentals & Property Management Co., Inc.

55 Sandy Pond Rd - Winchester Real Estate

$7,995,000 -  Single Family Home

55 Sandy Pond Rd - Lincoln, 01773

7 beds • 7 baths • 8,423 sqft

MLS ID: 73374986

Agent: Senkler, Pasley & Whitney

Office: Coldwell Banker Realty - Concord

51 Lantern Rd - Winchester Real Estate

$2,195,000 -  Single Family Home

51 Lantern Rd - Belmont, 02478

6 beds • 5.5 baths • 4,289 sqft

MLS ID: 73371502

Agent: Hurley

Office: Berkshire Hathaway HomeServices Commonwealth Real Estate

15 Tyler Road - Winchester Real Estate

$4,395,000 -  Single Family Home

15 Tyler Road - Lexington, 02420

6 beds • 6.5 baths • 7,739 sqft

MLS ID: 73371175

Agent: Beth Sager Group

Office: Keller Williams Realty Boston Northwest

77 Forest St - Winchester Real Estate

$350,000 -  Single Family Home

77 Forest St - Watertown, 02472

1 beds • 1.5 baths • 1,040 sqft

MLS ID: 73371076

Agent: DelRose McShane Team

Office: Coldwell Banker Realty - Belmont

93 Spring Street Unit 29 - Winchester Real Estate

$779,000 -  Condominium

93 Spring Street Unit 29 - Watertown, 02472

3 beds • 2.5 baths • 1,380 sqft

MLS ID: 73370374

Agent: Real Estate Advisors Group

Office: Coldwell Banker Realty - Belmont

8 Conant Rd - Winchester Real Estate

$8,999,999 -  Single Family Home

8 Conant Rd - Weston, 02493

5 beds • 7 baths • 7,382 sqft

MLS ID: 73370239

Agent: The Sarkis Team

Office: Douglas Elliman Real Estate - The Sarkis Team

9 Stanley Road - Winchester Real Estate

$3,199,900 -  Single Family Home

9 Stanley Road - Belmont, 02478

6 beds • 5 baths • 6,794 sqft

MLS ID: 73367997

Agent: The Toland Team

Office: Berkshire Hathaway HomeServices Commonwealth Real Estate

147 Ridge Street - Winchester Real Estate

$2,500,000 -  Single Family Home

147 Ridge Street - Arlington, 02474

6 beds • 5.5 baths • 4,382 sqft

MLS ID: 73367583

Agent: Real Estate Advisors Group

Office: Coldwell Banker Realty - Belmont

135 Marsh St - Winchester Real Estate

$6,400,000 -  Single Family Home

135 Marsh St - Belmont, 02478

4 beds • 6 baths • 8,069 sqft

MLS ID: 73366675

Agent: Hurley

Office: Berkshire Hathaway HomeServices Commonwealth Real Estate

8 Blueberry Lane - Winchester Real Estate

$4,449,000 -  Single Family Home

8 Blueberry Lane - Lexington, 02420

6 beds • 7.5 baths • 7,653 sqft

MLS ID: 73364744

Agent: Beth Sager Group

Office: Keller Williams Realty Boston Northwest

311 Concord Avenue - Winchester Real Estate

$3,368,000 -  Single Family Home

311 Concord Avenue - Lexington, 02421

5 beds • 6 baths • 7,012 sqft

MLS ID: 73363717

Agent: Keystone Homes Group

Office: Keller Williams Realty Boston Northwest

286 Country Dr - Winchester Real Estate

$8,495,000 -  Single Family Home

286 Country Dr - Weston, 02493

6 beds • 7.5 baths • 8,421 sqft

MLS ID: 73359549

Agent: Ricardo Rodriguez & Associates Group

Office: Coldwell Banker Realty - Boston

217 Summer St - Winchester Real Estate

$1,795,000 -  Single Family Home

217 Summer St - Weston, 02493

0 beds • 0 baths 0

MLS ID: 73358873

Agent: Glassoff

Office: Coldwell Banker Realty - Brookline

77 Waverley Avenue Unit 77 - Winchester Real Estate

$1,229,000 -  Condominium

77 Waverley Avenue Unit 77 - Watertown, 02472

3 beds • 2.5 baths • 2,396 sqft

MLS ID: 73358039

Agent: The Sarkis Team

Office: Douglas Elliman Real Estate - The Sarkis Team

14 Center St Unit 3 - Winchester Real Estate

$1,100,000 -  Condominium

14 Center St Unit 3 - Watertown, 02472

5 beds • 2.5 baths • 2,709 sqft

MLS ID: 73357181

Agent: Divine

Office: Berkshire Hathaway HomeServices Commonwealth Real Estate

67 Crosby St Unit 67 - Winchester Real Estate

$1,470,000 -  Condominium

67 Crosby St Unit 67 - Arlington, 02474

5 beds • 3.5 baths • 2,943 sqft

MLS ID: 73357056

Agent: Max Dublin Team

Office: Gibson Sotheby's International Realty

383 Marrett - Winchester Real Estate

$2,250,000 -  Single Family Home

383 Marrett - Lexington, 02421

4 beds • 5 baths • 4,300 sqft

MLS ID: 73352138

Agent: Alina Wang Team

Office: Coldwell Banker Realty - Lexington

72 Walnut St Unit 1 - Winchester Real Estate

$1,449,900 -  Condominium

72 Walnut St Unit 1 - Arlington, 02476

5 beds • 4.5 baths • 3,290 sqft

MLS ID: 73347705

Agent: Santana Team

Office: Keller Williams Realty Boston Northwest

335 Mystic St - Winchester Real Estate

$2,695,000 -  Single Family Home

335 Mystic St - Arlington, 02474

4 beds • 2.5 baths • 3,912 sqft

MLS ID: 73344573

Agent: Steve McKenna & The Home Advantage Team

Office: Gibson Sotheby's International Realty

10 Bowker St - Winchester Real Estate

$1,999,900 -  Single Family Home

10 Bowker St - Lexington, 02421

5 beds • 4 baths • 3,012 sqft

MLS ID: 73338560

Agent: Alina Wang Team

Office: Coldwell Banker Realty - Lexington

5 Chatham Way Unit 5 - Winchester Real Estate

$1,249,000 -  Condominium

5 Chatham Way Unit 5 - Watertown, 02472

3 beds • 3.5 baths • 2,350 sqft

MLS ID: 73335193

Agent: The Sarkis Team

Office: Douglas Elliman Real Estate - The Sarkis Team

6 Stratford Way - Winchester Real Estate

$3,200,000 -  Single Family Home

6 Stratford Way - Lincoln, 01773

5 beds • 5 baths • 8,707 sqft

MLS ID: 73332918

Agent: The Levy Real Estate Group

Office: Barrett Sotheby's International Realty

12 Robin Rd - Winchester Real Estate

$8,500,000 -  Single Family Home

12 Robin Rd - Weston, 02493

6 beds • 6.5 baths • 8,800 sqft

MLS ID: 73329379

Agent: Mizner + Montero

Office: Gibson Sotheby's International Realty

863 Concord Ave. - Winchester Real Estate

$6,499,000 -  Single Family Home

863 Concord Ave. - Belmont, 02478

7 beds • 7.5 baths • 8,905 sqft

MLS ID: 73303600

Agent: The Sarkis Team

Office: Douglas Elliman Real Estate - The Sarkis Team