5 Bedroom Homes for Sale in Brookline, MA

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1-41 of 58 Homes
5+ beds
a front view of a house with a yard
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5
Bedrooms
7,700
Square Feet
Unavailable
Acres

60 Lyman Road, Chestnut Hill, MA 02467

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$5,900,000 | 97-103 University Road, Brookline, MA 02445
1/8
Listed By Compass

$5,900,000

12
Bedrooms
7,308
Square Feet
0.28
Acres

97-103 University Road, Brookline, MA 02445

$2,280,000 | 77 Jordan Road, Brookline, MA 02446
1/29
Listed By Compass

$2,280,000

5
Bedrooms
3,213
Square Feet
0.23
Acres

77 Jordan Road, Brookline, MA 02446

$3,699,998 | 17 Chesham Road, Brookline, MA 02445
1/33
Listed By CompassOpen: 6/21 11:30AM - 12:30PM

$3,699,998

6
Bedrooms
5,487
Square Feet
0.26
Acres

17 Chesham Road, Brookline, MA 02445

$3,545,000 | 90 Columbia Street, Unit U90, Brookline, MA 02446
1/26
Listed By Compass

$3,545,000

5
Bedrooms
3,533
Square Feet
22.96
Acres

90 Columbia Street, Unit U90, Brookline, MA 02446

a front view of a house with a yard
1/24
Listed By Compass

$3,545,000

5
Bedrooms
3,533
Square Feet

90 Columbia Street, Unit U90, Brookline, MA 02446

$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
1/18
Listed By Compass

$4,250,000

5
Bedrooms
6,419
Square Feet
1.03
Acres

540 Chestnut Hill Avenue, Brookline, MA 02445

$4,650,000 | 50 Sumner Road, Brookline, MA 02445
1/32
Listed By Compass

$4,650,000

5
Bedrooms
5,423
Square Feet
0.41
Acres

50 Sumner Road, Brookline, MA 02445

$3,295,000 | 185 Warren Street, Brookline, MA 02445
1/25
Listed By CompassOpen: 6/20 12:00PM - 01:00PM

$3,295,000

5
Bedrooms
2,834
Square Feet
0.92
Acres

185 Warren Street, Brookline, MA 02445

$2,550,000 | 16 Kennard Road, Brookline, MA 02445
1/10
Listed By Compass

$2,550,000

8
Bedrooms
5,076
Square Feet
0.21
Acres

16 Kennard Road, Brookline, MA 02445

$4,995,000 | 40 Heath Hill, Brookline, MA 02445
1/40
Listed By Compass

$4,995,000

7
Bedrooms
6,560
Square Feet
0.72
Acres

40 Heath Hill, Brookline, MA 02445

$2,765,000 | 401 Heath Street, Brookline, MA 02467
1/27
Listed By CompassOpen: 6/20 01:30PM - 02:30PM

$2,765,000

5
Bedrooms
4,028
Square Feet
0.30
Acres

401 Heath Street, Brookline, MA 02467

$11,750,000 | 0 Sears Road, Brookline, MA 02445
1/16

$11,750,000

6
Bedrooms
10,000
Square Feet
2.03
Acres

0 Sears Road, Brookline, MA 02445

$14,995,000 | 33 Sears Road, Brookline, MA 02445
1/42
New

$14,995,000

6
Bedrooms
13,200
Square Feet
1.64
Acres

33 Sears Road, Brookline, MA 02445

$5,250,000 | 18 Naples Road, Brookline, MA 02446
1/40

$5,250,000

5
Bedrooms
5,198
Square Feet
0.12
Acres

18 Naples Road, Brookline, MA 02446

$2,500,000 | 128 Dudley Street, Brookline, MA 02445
1/21

$2,500,000

5
Bedrooms
3,219
Square Feet
0.30
Acres

128 Dudley Street, Brookline, MA 02445

a living room with furniture a fireplace and a large window
1/40

$8,995,000

7
Bedrooms
7,080
Square Feet
0.52
Acres

39 Worthington Road, Brookline, MA 02446

a front view of a house with yard and green space
1/42

$5,500,000

5
Bedrooms
7,058
Square Feet
Unavailable
Acres

15 Catlin Road, Brookline, MA 02445

an aerial view of a house with a garden
1/41
Virtual Tour

$4,350,000

7
Bedrooms
6,227
Square Feet
0.37
Acres

269 Kent Street, Brookline, MA 02446

a view of a city with a building in the background
1/42

$3,699,000

5
Bedrooms
5,068
Square Feet
0.32
Acres

71 Grove Street, Brookline, MA 02467

$5,100,000 | 129 Rangeley Road, Brookline, MA 02467
1/36
Virtual Tour

$5,100,000

6
Bedrooms
5,530
Square Feet
0.38
Acres

129 Rangeley Road, Brookline, MA 02467

a front view of a house with a yard
1/42

$2,749,999

5
Bedrooms
4,585
Square Feet
0.37
Acres

171 Shaw Road, Brookline, MA 02467

$14,850,000 | 280 Warren Street, Brookline, MA 02445
1/39

$14,850,000

6
Bedrooms
9,065
Square Feet
3.68
Acres

280 Warren Street, Brookline, MA 02445

an aerial view of a house
1/23

$8,200,000

6
Bedrooms
9,301
Square Feet
1.24
Acres

40 Singletree Road, Brookline, MA 02467

$1,850,000 | 184 Rawson Road, Unit 184, Brookline, MA 02445
1/27

$1,850,000

5
Bedrooms
2,460
Square Feet

184 Rawson Road, Unit 184, Brookline, MA 02445

a view of a brick building next to a road
1/42

$2,500,000

6
Bedrooms
4,404
Square Feet
0.08
Acres

293 Cypress Street, Brookline, MA 02445

$3,399,000 | 476 Heath Street, Brookline, MA 02467
1/39
Open: 6/20 11:00AM - 12:00PM

$3,399,000

9
Bedrooms
6,292
Square Feet
0.42
Acres

476 Heath Street, Brookline, MA 02467

a front view of a house with garden
1/35

$3,295,000

7
Bedrooms
4,493
Square Feet
0.13
Acres

100 Beals Street, Brookline, MA 02446

$3,295,000 | 100 Beals Street, Brookline, MA 02446
1/35

$3,295,000

7
Bedrooms
4,493
Square Feet
0.13
Acres

100 Beals Street, Brookline, MA 02446

$2,399,000 | 121 Thorndike Street, Brookline, MA 02446
1/39
Open: 6/20 12:30PM - 02:00PM

$2,399,000

5
Bedrooms
3,195
Square Feet
0.14
Acres

121 Thorndike Street, Brookline, MA 02446

a front view of a house with a yard and trees
1/32

$9,500,000

7
Bedrooms
9,500
Square Feet
0.86
Acres

355 Buckminster Road, Brookline, MA 02445

$3,995,000 | 68 Dudley Street, Brookline, MA 02445
1/29

$3,995,000

5
Bedrooms
5,234
Square Feet
0.46
Acres

68 Dudley Street, Brookline, MA 02445

$5,950,000 | 19 Linden Street, Brookline, MA 02445
1/34

$5,950,000

6
Bedrooms
4,253
Square Feet
0.41
Acres

19 Linden Street, Brookline, MA 02445

$4,250,000 | 53 Winslow Road, Brookline, MA 02446
1/20

$4,250,000

6
Bedrooms
4,865
Square Feet
0.14
Acres

53 Winslow Road, Brookline, MA 02446

a front view of a house with garden
1/36

$1,990,000

5
Bedrooms
3,000
Square Feet
0.11
Acres

303 Russett Road, Brookline, MA 02467

$2,995,000 | 2 Mason Terrace, Brookline, MA 02446
1/38

$2,995,000

6
Bedrooms
5,748
Square Feet
0.26
Acres

2 Mason Terrace, Brookline, MA 02446

$6,250,000 | 300 Warren Street, Brookline, MA 02445
1/35

$6,250,000

7
Bedrooms
7,327
Square Feet
0.97
Acres

300 Warren Street, Brookline, MA 02445

a front view of a house with a yard
1/8

$2,400,000

5
Bedrooms
3,161
Square Feet
0.14
Acres

79 Winthrop Road, Brookline, MA 02445

a aerial view of a house with a yard and large trees
1/27

$6,800,000

7
Bedrooms
6,000
Square Feet
0.92
Acres

75 Goddard Avenue, Brookline, MA 02445

$869,000 | 16 Garrison Road, Unit 7, Brookline, MA 02445
1/33

$869,000

5
Bedrooms
1,413
Square Feet

16 Garrison Road, Unit 7, Brookline, MA 02445

$1,350,000 | 23 Netherlands Road, Unit 1, Brookline, MA 02445
1/35
Open: 6/20 02:00PM - 03:30PMVirtual Tour

$1,350,000

7
Bedrooms
2,237
Square Feet

23 Netherlands Road, Unit 1, Brookline, MA 02445

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Surrounded by greenery, Brookline is a haven for nature-lovers with a tight local community. The town has thriving small businesses and a grassroots arts scene, with all the attractions of Boston and Cambridge just next door.

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