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Brookline's 10 Priciest Mansions for Sale Right Now

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Brookline is obviously no stranger to big-time mansions and their big-time asking prices. The town currently hosts two of the biggest big-time (big!) listings in the entire Greater Boston region: the 23-room estate at 39 Sears Road asking $17,000,000 and the 12-room spread with private pond at 101 Fernwood Road asking $18,000,000 (pictured). There are so many others, though, many of them fairly recent to the market. They may not be as gobsmackingly priced as 39 Sears and 101 Fernwood, but they are each nothing to sneeze at in that department.


· This $17M Brookline Estate Is Nothing But Second-Best Now [Curbed Boston]
· Yegads! Greater Boston's Priciest Listing From the Air [Curbed Boston]

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1. 101 Fernwood Road

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101 Fernwood Road
Chestnut Hill, MA 02467

Price: $18,000,000
This 3.72-acre estate, featuring a 10,000-square-foot house, is the priciest listing in Greater Boston in at least a decade. It hit the market two months ago.

2. 39 Sears Road

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39 Sears Road
Brookline, MA 02445

Price: $17,000,000
This more than 3-acre estate, with a 15,453-square-foot mansion, has been on the market almost a year now.

3. 407 Warren Street

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407 Warren Street
Brookline, MA 02445

Price: $6,200,000
Yup, a steep drop-off in price between Nos. 2 and 3 here. This nearly 1.5-acre estate, with a 7,500-square-foot house, has been on the market for two months.

4. 75 Sargent Road

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75 Sargent Road
Brookline, MA 02445

Price: $5,650,000
This 1.2-acre estate, featuring not only a 6,028-square-foot house but one of the largest Japanese maples in North America, has been on the market for just shy of 100 days.

5. 10 Lyman Road

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10 Lyman Road
Chestnut Hill, MA 02467

Price: $5,250,000
On the market for barely seven weeks, this 6,777-square-foot house sits on just under 1 acre.

6. 64 Dudley Street

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64 Dudley Street
Brookline, MA 02445

Price: $4,995,000
This 9,581-square-foot spread, which covers nearly the nearly 1-acre site its on, has been up for grabs since late April.

7. 290 Warren Street

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290 Warren Street
Brookline, MA 02445

Price: $4,800,000
The 5,581-square-foot house on nearly 1.5 acres has been on the market for just over a month.

8. 30 Clyde Street

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30 Clyde Street
Chestnut Hill, MA 02467

Price: $4,800,000
This 7,048-square-foot house on nearly nine-tenths of an acre has been on the market since late September.

9. 324 Heath Street

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324 Heath Street
Chestnut Hill, MA 02467

Price: $4,250,000
The 6,000-square-footer was newly built on about 1 acre. It's been on the market since November.

10. 22 Worthington Road

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22 Worthington Road
Brookline, MA 02446

Price: $4,200,000This 8,175-square-foot mansion, which has been on the market for just over a month, basically eats up the quarter-acre it's on.

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1. 101 Fernwood Road

101 Fernwood Road, Chestnut Hill, MA 02467

Price: $18,000,000
This 3.72-acre estate, featuring a 10,000-square-foot house, is the priciest listing in Greater Boston in at least a decade. It hit the market two months ago.

101 Fernwood Road
Chestnut Hill, MA 02467

2. 39 Sears Road

39 Sears Road, Brookline, MA 02445

Price: $17,000,000
This more than 3-acre estate, with a 15,453-square-foot mansion, has been on the market almost a year now.

39 Sears Road
Brookline, MA 02445

3. 407 Warren Street

407 Warren Street, Brookline, MA 02445

Price: $6,200,000
Yup, a steep drop-off in price between Nos. 2 and 3 here. This nearly 1.5-acre estate, with a 7,500-square-foot house, has been on the market for two months.

407 Warren Street
Brookline, MA 02445

4. 75 Sargent Road

75 Sargent Road, Brookline, MA 02445

Price: $5,650,000
This 1.2-acre estate, featuring not only a 6,028-square-foot house but one of the largest Japanese maples in North America, has been on the market for just shy of 100 days.

75 Sargent Road
Brookline, MA 02445

5. 10 Lyman Road

10 Lyman Road, Chestnut Hill, MA 02467

Price: $5,250,000
On the market for barely seven weeks, this 6,777-square-foot house sits on just under 1 acre.

10 Lyman Road
Chestnut Hill, MA 02467

6. 64 Dudley Street

64 Dudley Street, Brookline, MA 02445

Price: $4,995,000
This 9,581-square-foot spread, which covers nearly the nearly 1-acre site its on, has been up for grabs since late April.

64 Dudley Street
Brookline, MA 02445

7. 290 Warren Street

290 Warren Street, Brookline, MA 02445

Price: $4,800,000
The 5,581-square-foot house on nearly 1.5 acres has been on the market for just over a month.

290 Warren Street
Brookline, MA 02445

8. 30 Clyde Street

30 Clyde Street, Chestnut Hill, MA 02467

Price: $4,800,000
This 7,048-square-foot house on nearly nine-tenths of an acre has been on the market since late September.

30 Clyde Street
Chestnut Hill, MA 02467

9. 324 Heath Street

324 Heath Street, Chestnut Hill, MA 02467

Price: $4,250,000
The 6,000-square-footer was newly built on about 1 acre. It's been on the market since November.

324 Heath Street
Chestnut Hill, MA 02467

10. 22 Worthington Road

22 Worthington Road, Brookline, MA 02446

Price: $4,200,000This 8,175-square-foot mansion, which has been on the market for just over a month, basically eats up the quarter-acre it's on.

22 Worthington Road
Brookline, MA 02446