108 Homes for Sale in Wellesley
$10,995,000
5
Beds
5/1
Baths
7,200
Sqft
45 White Oak Rd
Wellesley, MA 02481
Year Built:
2025
HOA:
None
$6,950,000
8
Beds
6/3
Baths
9,662
Sqft
200 Pond Road
Wellesley, MA 02482
Year Built:
1990
HOA:
None
$6,665,000
6
Beds
5/3
Baths
8,093
Sqft
222 Grove Street
Wellesley, MA 02482
Year Built:
2025
HOA:
None
$6,350,000
6
Beds
6/1
Baths
7,569
Sqft
9 Bellevue Road
Wellesley, MA 02481
Year Built:
2023
HOA:
None
$5,995,000
6
Beds
4/2
Baths
7,738
Sqft
43 Monadnock Road
Wellesley, MA 02481
Year Built:
1937
HOA:
None
$5,950,000
6
Beds
5/2
Baths
7,040
Sqft
25 Kenilworth Road
Wellesley, MA 02482
Year Built:
1929
HOA:
None
$5,950,000
7
Beds
7/2
Baths
7,600
Sqft
45 Longmeadow Rd
Wellesley, MA 02482
Year Built:
2018
HOA:
None
$5,695,000
5
Beds
6/1
Baths
9,400
Sqft
196 Pond Road
Wellesley, MA 02482
Year Built:
2021
HOA:
None
$5,497,000
5
Beds
5/2
Baths
6,377
Sqft
48 Marshall Rd
Wellesley, MA 02482
Year Built:
2017
HOA:
None
$5,495,000
6
Beds
5/3
Baths
9,848
Sqft
182 Winding River Road
Wellesley, MA 02482
Year Built:
2006
HOA:
None
$5,350,000
5
Beds
5/2
Baths
5,230
Sqft
14 Bristol Road
Wellesley, MA 02481
Year Built:
2013
HOA:
None
$5,100,000
7
Beds
5/2
Baths
7,262
Sqft
200 Cliff Rd
Wellesley, MA 02481
Year Built:
1938
HOA:
None
$4,999,000
6
Beds
6/2
Baths
9,036
Sqft
12 Winding River Cir
Wellesley, MA 02482
Year Built:
2004
HOA:
None
$4,995,000
6
Beds
5/3
Baths
7,254
Sqft
1 Stonefield Lane
Wellesley, MA 02482
Year Built:
2004
HOA:
None
$4,870,000
6
Beds
6/2
Baths
7,197
Sqft
179 Oakland St
Wellesley, MA 02481
Year Built:
2010
HOA:
None
$4,395,000
6
Beds
6/1
Baths
6,975
Sqft
8 Valley Road
Wellesley, MA 02481
Year Built:
2006
HOA:
None
$4,350,000
6
Beds
5/2
Baths
8,038
Sqft
22 Plymouth Road
Wellesley, MA 02481
Year Built:
2005
HOA:
None
$4,295,000
5
Beds
5/1
Baths
5,210
Sqft
17 Midland Road
Wellesley, MA 02482
Year Built:
1924
HOA:
None
$3,850,000
6
Beds
5
Baths
6,990
Sqft
151 Oakland Street
Wellesley, MA 02481
Year Built:
1748
HOA:
None
$3,800,000
5
Beds
6/1
Baths
6,511
Sqft
11 Skyline Drive
Wellesley, MA 02482
Year Built:
2026
HOA:
None
$3,795,000
6
Beds
5/1
Baths
7,047
Sqft
201 Lowell Road
Wellesley, MA 02481
Year Built:
2025
HOA:
None
$3,500,000
5
Beds
5/1
Baths
5,800
Sqft
144 Washington Street
Wellesley, MA 02481
Year Built:
2026
HOA:
None
$3,495,000
5
Beds
4/1
Baths
4,936
Sqft
7 Massasoit Road
Wellesley, MA 02481
Year Built:
2022
HOA:
None
$3,398,500
6
Beds
5/1
Baths
5,080
Sqft
28 Parker Rd
Wellesley, MA 02482
Year Built:
2026
HOA:
None
$3,325,000
2
Beds
2/1
Baths
1,937
Sqft
580 Washington Street #304
Wellesley, MA 02482
Year Built:
2015
HOA:
None
$3,299,000
6
Beds
4/1
Baths
4,424
Sqft
209 Bristol Rd
Wellesley, MA 02481
Year Built:
1962
HOA:
None
$3,295,000
6
Beds
4/1
Baths
6,034
Sqft
1 Kenilworth Circle
Wellesley, MA 02482
Year Built:
1931
HOA:
None
$3,295,000
5
Beds
4/1
Baths
5,105
Sqft
18 Rockland Street
Wellesley, MA 02481
Year Built:
2026
HOA:
None
$3,250,000
4
Beds
3/1
Baths
3,712
Sqft
25 Hundreds Cir
Wellesley, MA 02481
Year Built:
1930
HOA:
None
$3,245,000
5
Beds
4/1
Baths
4,416
Sqft
38 Parker Rd
Wellesley, MA 02482
Year Built:
2026
HOA:
None
$3,195,000
5
Beds
4/2
Baths
5,735
Sqft
31 Alba Rd
Wellesley, MA 02481
Year Built:
1950
HOA:
None
$3,150,000
4
Beds
4/1
Baths
5,200
Sqft
35 Marshall Rd
Wellesley, MA 02482
Year Built:
2016
HOA:
None
$2,899,000
6
Beds
3/3
Baths
5,806
Sqft
42 Edmunds Road
Wellesley, MA 02481
Year Built:
1933
HOA:
None
$2,885,000
5
Beds
4
Baths
4,110
Sqft
100 Albion Rd
Wellesley, MA 02481
Year Built:
1978
HOA:
None
$2,865,000
5
Beds
5/1
Baths
5,172
Sqft
265 Weston Rd
Wellesley, MA 02482
Year Built:
2024
HOA:
None
$2,600,000
2
Beds
2
Baths
1,475
Sqft
148 Weston Rd #304
Wellesley, MA 02482
Year Built:
2021
HOA:
None
$2,599,000
5
Beds
3/1
Baths
5,428
Sqft
22 Tanglewood Road
Wellesley, MA 02481
Year Built:
1958
HOA:
None
$2,495,000
4
Beds
3/1
Baths
4,201
Sqft
283 Walnut Street
Wellesley, MA 02481
Year Built:
1874
HOA:
None
$2,380,000
5
Beds
4/1
Baths
3,600
Sqft
37 Oakland St
Wellesley, MA 02481
Year Built:
2026
HOA:
None
$2,349,000
4
Beds
3/1
Baths
3,776
Sqft
38 Upwey Rd
Wellesley, MA 02481
Year Built:
1993
HOA:
None
$2,250,000
8
Beds
4/2
Baths
5,559
Sqft
9-11 Hampden Street
Wellesley, MA 02482
Year Built:
1920
HOA:
None
$2,200,000
3
Beds
1/1
Bath
1,595
Sqft
53 Elmwood Rd
Wellesley, MA 02481
Year Built:
1900
HOA:
None
$2,150,000
5
Beds
3/1
Baths
3,704
Sqft
77 Cedar Street
Wellesley, MA 02481
Year Built:
2011
HOA:
None
$2,150,000
5
Beds
3
Baths
2,628
Sqft
33 Linden Street
Wellesley, MA 02482
Year Built:
1899
HOA:
None
$1,925,000
4
Beds
2/1
Baths
2,896
Sqft
40 Kimlo Rd
Wellesley, MA 02481
Year Built:
1878
HOA:
None
$1,895,000
4
Beds
3/1
Baths
3,200
Sqft
126 Walnut St #126
Wellesley, MA 02481
Year Built:
2014
HOA:
None
$1,799,999
5
Beds
3/1
Baths
4,643
Sqft
7 Garden Rd
Wellesley, MA 02481
Year Built:
1985
HOA:
None
$1,799,000
4
Beds
2/1
Baths
2,791
Sqft
98 Brook Street
Wellesley, MA 02482
Year Built:
1922
HOA:
None
$1,747,200
2
Beds
2/1
Baths
1,792
Sqft
16 Stearns Rd #208
Wellesley, MA 02482
Year Built:
2026
HOA:
None
$1,699,000
5
Beds
4
Baths
2,267
Sqft
29 Cottage St
Wellesley, MA 02482
Year Built:
1869
HOA:
None
$1,625,000
3
Beds
2/1
Baths
2,212
Sqft
20 Shaw Rd
Wellesley, MA 02481
Year Built:
1936
HOA:
None
$1,625,000
3
Beds
3/1
Baths
2,377
Sqft
63 OAk Street #A
Wellesley, MA 02482
Year Built:
2025
HOA:
None
$1,599,000
4
Beds
2/1
Baths
2,200
Sqft
127 Prospect St
Wellesley, MA 02481
Year Built:
1935
HOA:
None
$1,599,000
2
Beds
2
Baths
1,591
Sqft
16 Stearns Rd #304
Wellesley, MA 02482
Year Built:
2025
HOA:
None
$1,595,000
3
Beds
2/1
Baths
3,012
Sqft
30 S River St
Wellesley, MA 02482
Year Built:
1862
HOA:
None
$1,500,000
3
Beds
3
Baths
2,447
Sqft
44 Windemere Rd
Wellesley, MA 02481
Year Built:
1958
HOA:
None
$1,498,000
2
Beds
2/1
Baths
1,604
Sqft
16 Stearns Rd #203
Wellesley, MA 02482
Year Built:
2026
HOA:
None
$1,490,000
4
Beds
3
Baths
2,218
Sqft
32 Bobolink Rd
Wellesley, MA 02481
Year Built:
1955
HOA:
None
$1,399,000
3
Beds
1/1
Bath
1,320
Sqft
10 Wilde Rd
Wellesley, MA 02481
Year Built:
1937
HOA:
None
$1,399,000
4
Beds
2/1
Baths
1,800
Sqft
560 Worcester Street
Wellesley, MA 02481
Year Built:
1938
HOA:
None
$1,398,000
3
Beds
2
Baths
1,457
Sqft
16 Stearns Rd #207
Wellesley, MA 02482
Year Built:
2025
HOA:
None
$1,395,000
3
Beds
2
Baths
1,640
Sqft
30r Morses Pond Road
Wellesley, MA 02428
Year Built:
1930
HOA:
None
$1,349,000
3
Beds
2/1
Baths
2,140
Sqft
63 Russell Rd
Wellesley, MA 02482
Year Built:
1969
HOA:
None
$1,348,000
3
Beds
1/1
Bath
2,384
Sqft
41-a Hunnewell Street
Wellesley, MA 02481
Year Built:
1965
HOA:
None
$1,299,000
4
Beds
2
Baths
2,233
Sqft
31 Lantern Lane
Wellesley, MA 02481
Year Built:
1910
HOA:
None
$1,275,000
3
Beds
3
Baths
1,848
Sqft
22 Cedar St
Wellesley, MA 02482
Year Built:
1920
HOA:
None
$1,198,000
3
Beds
1/1
Bath
1,813
Sqft
296 Linden St
Wellesley, MA 02481
Year Built:
1910
HOA:
None
$1,195,000
2
Beds
2/1
Baths
1,909
Sqft
286 Linden Street #286
Wellesley, MA 02482
Year Built:
1986
HOA:
None
$1,160,000
4
Beds
1/1
Bath
1,400
Sqft
2 Marigold Ave
Wellesley, MA 02482
Year Built:
1983
HOA:
None
$1,100,000
3
Beds
2/1
Baths
2,165
Sqft
6 Willow Street
Wellesley, MA 02481
Year Built:
1920
HOA:
None
$1,068,000
2
Beds
2
Baths
1,739
Sqft
26 Pleasant St #B
Wellesley, MA 02482
Year Built:
1988
HOA:
None
$1,045,000
1
Bed
1/1
Bath
1,205
Sqft
63 Garden Rd #C5
Wellesley, MA 02481
Year Built:
1986
HOA:
None
$999,900
2
Beds
2
Baths
1,057
Sqft
16 Stearns Rd #302
Wellesley, MA 02482
Year Built:
2025
HOA:
None
$839,000
2
Beds
1/1
Bath
1,171
Sqft
11 Oak Street #33
Wellesley, MA 02482
Year Built:
1967
HOA:
None
$839,000
2
Beds
1/1
Bath
1,500
Sqft
21 Westerly Street #1
Wellesley, MA 02482
Year Built:
1971
HOA:
None
$795,000
1
Bed
1
Bath
1,230
Sqft
202 WAshington Street #A
Wellesley, MA 02481
Year Built:
2023
HOA:
None
$39,000/mo
6
Beds
4/1
Baths
5,091
Sqft
28 Longfellow Rd
Wellesley, MA 02481
Year Built:
--
HOA:
None
$16,999/mo
6
Beds
5
Baths
5,220
Sqft
28 Maurice Rd #28
Wellesley, MA 02482
Year Built:
2019
HOA:
None
$16,800/mo
5
Beds
3/3
Baths
6,400
Sqft
23 Bellevue Road
Wellesley, MA 02481
Year Built:
1983
HOA:
None
$12,000/mo
4
Beds
4/1
Baths
3,071
Sqft
15 Waban St #15
Wellesley, MA 02481
Year Built:
1910
HOA:
None
$11,000/mo
5
Beds
5
Baths
3,480
Sqft
3 Sprague Rd
Wellesley, MA 02481
Year Built:
1955
HOA:
None
$10,500/mo
4
Beds
3/1
Baths
4,502
Sqft
10 Larch Rd #10
Wellesley, MA 02482
Year Built:
2012
HOA:
None
$9,000/mo
4
Beds
3
Baths
3,400
Sqft
3 Sprague Rd
Wellesley, MA 02482
Year Built:
1955
HOA:
None
$8,500/mo
4
Beds
2/1
Baths
2,466
Sqft
124 Pilgrim Rd
Wellesley, MA 02481
Year Built:
1953
HOA:
None
$8,400/mo
3
Beds
2/1
Baths
1,772
Sqft
144 Linden Street #3
Wellesley, MA 02482
Year Built:
2023
HOA:
None
$8,400/mo
3
Beds
2/1
Baths
1,770
Sqft
144 Linden Street #2
Wellesley, MA 02482
Year Built:
1910
HOA:
None
$8,200/mo
5
Beds
3
Baths
2,875
Sqft
20 Donizetti St
Wellesley, MA 02482
Year Built:
1905
HOA:
None
$8,000/mo
2
Beds
2/1
Baths
1,805
Sqft
16 Stearns Rd #108
Wellesley, MA 02482
Year Built:
2025
HOA:
None
$7,300/mo
4
Beds
2/1
Baths
2,256
Sqft
52 Riverdale Road #52
Wellesley, MA 02481
Year Built:
1927
HOA:
None
$7,250/mo
3
Beds
2
Baths
1,435
Sqft
16 Stearns Rd #207
Wellesley, MA 02482
Year Built:
2025
HOA:
None
$6,900/mo
4
Beds
3/1
Baths
3,352
Sqft
141 Westgate Road
Wellesley, MA 02481
Year Built:
1979
HOA:
None
$6,600/mo
4
Beds
2/1
Baths
2,408
Sqft
2 Minuteman Ln
Wellesley, MA 02481
Year Built:
1995
HOA:
None
$6,500/mo
2
Beds
2/1
Baths
1,457
Sqft
16 Stearns Rd #106
Wellesley, MA 02482
Year Built:
2025
HOA:
None
$6,000/mo
2
Beds
2/1
Baths
1,906
Sqft
286 Linden Street #286
Wellesley, MA 02482
Year Built:
1986
HOA:
None
$5,750/mo
4
Beds
1/1
Bath
2,100
Sqft
12 Leighton Road #2
Wellesley, MA 02482
Year Built:
--
HOA:
None
$5,600/mo
3
Beds
2
Baths
1,416
Sqft
85 Alba Rd
Wellesley, MA 02481
Year Built:
1955
HOA:
None
$5,200/mo
4
Beds
2
Baths
2,340
Sqft
749 Worcester Street
Wellesley, MA 02481
Year Built:
1986
HOA:
None
$5,000/mo
4
Beds
2/1
Baths
1,572
Sqft
71 Curve St #71
Wellesley, MA 02482
Year Built:
1904
HOA:
None
$4,695/mo
3
Beds
1/1
Bath
1,625
Sqft
22 Cleveland Rd
Wellesley, MA 02481
Year Built:
1925
HOA:
None
$4,500/mo
4
Beds
1/1
Bath
1,616
Sqft
15 Ledyard St #15
Wellesley, MA 02481
Year Built:
1928
HOA:
None
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