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Boston's Biggest Price-Chops

October 2011 may best be remembered in Boston Real Estate Land as the month Tom Brady and Gisele Bundchen dropped a $400,000 price-chop on the Back Bay penthouse they've been trying to unload, on and off, since 2009.

These are the 10 biggest price-chops by dollar amount of homes currently on the Boston market (we'll give Tomsele a pass—technically, they had taken their home off the market before putting it back on chopped).

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10) 96 Beacon Street, #1

Original Asking Price: $1,975,000
Price-Chop: $125,000 on Oct. 1
Square Feet: 1,634
The Skinny: This 2-BR, 2-BA Beacon Hill bombshell has nothing to be ashamed of: gourmet kitchen with breakfast bar; fireplace in the living room; large master suite with lots of closet space; even deeded parking. Regardless, according to Trulia, it's still asking a bit much when compared to similar homes in the neighborhood.

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marlborough.jpg9) 249 Marlborough Street, #2
Original Asking Price: $1,424,000
Price-Chop: $126,000 on Sept. 28
Square Feet: 1,810
The Skinny: This Back Bay condo seems a perfectly suitable gem, price to move compared to similar homes that have, in fact, moved recently. The only thing holding it back perhaps is that it was once a 2-BR and is now, thanks to renovations, what the listing describes as "1+."

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8) 135 Marlborough Street, #8
Original Asking Price: $799,000
Price-Chop: $50,000 on Sept. 2; a further $150,000 on Oct. 11
Square Feet: 805
The Skinny: The listing for this Back Bay condo in a beautiful brownstone makes much of being on the sunny side of Marlborough. But it can't overcome the size—similar homes seem to move at about $100K less than what this one's at now, even after two chops. Another to come?

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7) 9 Lime Street
Original Asking Price: $2,850,000
Price-Chop: $155,000 on Oct. 8
Square Feet: 3,404,000
The Skinny: No denying that this 4-BR, 4-BA Beacon Hill townhouse is a savory one. Gawk on! But it's still way overpriced, according to the numbers, with an asking price nearly $1 million more than the average for Beacon Hill.

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63atlanticave.jpg6) 63 Atlantic Avenue, #5B
Original Asking Price: $1,190,000
Price-Chop: $191,000 on Sept. 13
Square Feet: 1,268
The Skinny: This 2-BR, 2-BA has Harbor views out the wazoo; high ceilings; custom molding; two private balconies (for the views); a stone fireplace; and floor-to-ceiling windows (again with the views!). But it's asking just a tad much, compared to similar homes in the North End. Another $8K or thereabouts and move it does.

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5) 300 Commercial Street, #710
Original Asking Price: $2,799,000
Price-Chop: $200,000 on May 5; a further $200,000 on July 30
Square Feet: 1,654
The Skinny: This North End 2-BR, 2-BA is willing to play ball, with $400,000 in total price-chops in just six months. As it stands now, it's price to move, compared with other homes in the area that have. Plus, it's got 2,000 square feet of deck space. Come on, people! Two thousand square feet of deck space!

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4) 220 B Allandale, #B
Original Asking Price: $1,650,000
Price-Chop: $255,000 on Oct. 5
Square Feet: 4,743
The Skinny: We're honestly baffled by this one in West Roxbury. On the one hand, this 4-BR, 4.5-BA on the Brookline-Boston line unfolds in true mansion-like fashion, complete with a library and membership within a carefully lubricated gated community. On the other, it's way overpriced, even with the $255K chop.

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3) 66 Mount Vernon Street, #1
Original Asking Price: $2,950,000
Price-Chop: $151,000 on April 21; a further $300,000 on July 8
Square Feet: N/A
The Skinny: This 3-BR, 3.5-BA Beacon Hill condo has had a rough go of it—$451,000 in chops since late April and still no suitor. Maybe it really is a "hidden gem on the Hill," as the listing says. But it's now more inline with other luxury sales prices in the area, so this could be its autumn.

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2) 347 Commonwealth Avenue, #PH
Original Asking Price: $3,150,000
Price-Chop: $160,000 on July 30; a further $340,000 on Oct. 4
Square Feet: 1,956
The Skinny: Tomsele have nothing on this 3-BR, 2.5-BA condo in Back Bay, with its staggeringly precipitous half-million in price-chops in barely the last three months. What now for it? A sale, probably, at least according to Trulia's comps for similar homes in the area. This one, with its last price-chop three weeks ago, may have found its proper place in line.

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1) 65 East India Row, #28B-F
Original Asking Price: $3,399,000
Price-Chop: $351,000 on Sept. 7
Square Feet: 6,119
The Skinny: We know what's holding this Downtown Crossing knockout back—it needs serious renovations (don't let the photo fool you!), meaning the hefty price tag's only the beginning. Of course, we imagine that anyone playing in this rarefied air can afford whatever needs to be done on top of the $3.399M.

· Tom Brady and Gisele Bundchen Downsizing in Back Bay? [Curbed Boston]
· Tom Brady, Gisele Busting a Move in Back Bay [Herald]
· Tom Brady Manor Marked Down [Herald]
· Tom Brady, Gisele Bundchen Price-Chop Back Bay Manse [Curbed Boston]
· Tom Brady and Gisele Bundchen's Very Exclusive Condo Club [Curbed Boston]