Winchester

Winchester is a picturesque town of 21,374 people located 8 miles north of downtown Boston and bordering the towns of Woburn, Stoneham, Medford, Arlington and Lexington. Winchester's charming downtown,  Middlesex Fells state park reservation, excellent public schools, and close proximity to Boston make it a very desirable and beautiful place to live. 

For Sale in Winchester:

All Listings Under $500,000 $500,000 - $750,000
$750,000 - $1,000,000 $1,000,000 - $1,500,000 $1,500,000 - $2,000,000
$2,000,000 - $2,500,000 $2,500,000 - $3,000,000
15 Lawson Road, Winchester
  • Single Family
  • 5 Beds
  • 5 Baths
  • 5,713 SqFt

15 Lawson Road, Winchester

$2,999,900
65 Myopia Road, Winchester
  • Single Family
  • 4 Beds
  • 5 Baths
  • 7,206 SqFt

65 Myopia Road, Winchester

$2,599,999
New
34 Everett Ave, Winchester
  • Single Family
  • 6 Beds
  • 4 Baths
  • 4,359 SqFt

34 Everett Ave, Winchester

$2,599,000
New
2 Edgewater Place, Winchester
  • Single Family
  • 4 Beds
  • 5 Baths
  • 3,945 SqFt

2 Edgewater Place, Winchester

$2,299,000
27 Gershon Way #27, Winchester
  • Condominium
  • 3 Beds
  • 3 Baths
  • 2,638 SqFt

27 Gershon Way #27, Winchester

$2,050,000
1 Stonefield Circle, Winchester
  • Single Family
  • 5 Beds
  • 5 Baths
  • 5,116 SqFt

1 Stonefield Circle, Winchester

$1,849,000 ↓ $50,000
248 Forest St, Winchester
  • Single Family
  • 5 Beds
  • 5 Baths
  • 5,200 SqFt

248 Forest St, Winchester

$1,799,900 ↓ $49,100
6-8 Richardson St, Winchester
  • Multi-Family
  • 4 Beds
  • 4 Baths
  • 3,615 SqFt

6-8 Richardson St, Winchester

$1,500,000
25 Gershon Way #25, Winchester
  • Condominium
  • 3 Beds
  • 4 Baths
  • 2,980 SqFt

25 Gershon Way #25, Winchester

$1,475,000
36 Elmwood Avenue #10, Winchester
  • Condominium
  • 2 Beds
  • 2 Baths
  • 1,580 SqFt

36 Elmwood Avenue #10, Winchester

$1,449,000 ↑ $20,000
New
8-10 Winter St, Winchester
  • Multi-Family
  • 6 Beds
  • 6 Baths
  • 4,395 SqFt

8-10 Winter St, Winchester

$1,399,000
37 Cambridge St, Winchester
  • Single Family
  • 4 Beds
  • 4 Baths
  • 3,298 SqFt

37 Cambridge St, Winchester

$1,350,000

For Rent in Winchester:

282 High Street Ext., Winchester
  • Rental
  • 6 Beds
  • 5 Baths
  • 6,500 SqFt

282 High Street Ext., Winchester

$14,000
New
846 Main Street #3a, Winchester
  • Rental
  • 3 Beds
  • 3 Baths
  • 3,450 SqFt

846 Main Street #3a, Winchester

$8,800
New
846 Main Street #3, Winchester
  • Rental
  • 3 Beds
  • 3 Baths
  • 2,900 SqFt

846 Main Street #3, Winchester

$7,500
New
846 Main Street #1, Winchester
  • Rental
  • 3 Beds
  • 3 Baths
  • 2,900 SqFt

846 Main Street #1, Winchester

$6,500
2 Rangeley Road #2, Winchester
  • Rental
  • 2 Beds
  • 3 Baths
  • 1,200 SqFt

2 Rangeley Road #2, Winchester

$4,600 ↓ $200
48 Spruce Street #48, Winchester
  • Rental
  • 4 Beds
  • 4 Baths
  • 2,500 SqFt

48 Spruce Street #48, Winchester

$4,500
New
4 Nassau #sf, Winchester
  • Rental
  • 3 Beds
  • 3 Baths
  • 2,261 SqFt

4 Nassau #sf, Winchester

$3,700
New
37 Loring Ave #1, Winchester
  • Rental
  • 3 Beds
  • 2 Baths
  • 1,800 SqFt

37 Loring Ave #1, Winchester

$3,595
New
77 Harvard St #sf, Winchester
  • Rental
  • 4 Beds
  • 2 Baths
  • 2,400 SqFt

77 Harvard St #sf, Winchester

$3,295
60 Lake St #d, Winchester
  • Rental
  • 2 Beds
  • 2 Baths
  • 1,460 SqFt

60 Lake St #d, Winchester

$2,850
666 Main St #403, Winchester
  • Rental
  • 2 Beds
  • 2 Baths
  • 1,170 SqFt

666 Main St #403, Winchester

$2,700 ↓ $100
200 Swanton St #403, Winchester
  • Rental
  • 2 Beds
  • 1 Bath
  • 822 SqFt

200 Swanton St #403, Winchester

$2,550 ↑ $550

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