Luxury Homes

10 Most Expensive Homes in Boston This Fall

The most expensive homes in Boston are still in Back Bay and Beacon Hill.

There’s now a $37.5 million penthouse on the market — a price unprecedented in Boston. The 60th floor penthouse suite in the to-be-built Millennium Tower in Downtown Crossing is a whopping 13,000 square feet. That’s only 1,000 square feet smaller than Tom Brady and Gisele Bundchen’s new Brookline mansion.

Luxury is popping up in unexpected neighborhoods these days (think Chinatown, the West End, the Seaport), but the priciest properties are still the classic row houses in Back Bay and Beacon Hill.

1. 74 Beacon Street

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This townhouse offers up some of the best vantage points in the city: it has a large infinity pool on the roof, a second rooftop deck, and three other balconies. Inside, there’s a wine cellar with cigar humidor, a wood paneled library, and a gym, and it stays warms with its — wait for it — eight fireplaces.

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Listed price: $13,950,000

Rooms: 6 bedrooms, 6 full bathrooms, 3 partial bathrooms

Square feet: 8,450

Price per square foot: $1,651

2. 130 Commonwealth Avenue

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This is the place for wine enthusiasts — it has a 2,200-bottle wine cellar. The limestone façade of this Back Bay building makes it stand out from the rest of the neighborhood’s brownstone buildings. The unit also comes with six parking spaces, which are probably worth a ton by themselves. We’re in Boston, after all.

Listed price: $13,400,000

Rooms: 5 bedrooms, 6 full bathrooms, 2 partial bathrooms

Square feet: 9,908

Price per square foot: $1,352

3. 56 Beacon Street

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Floor to ceiling windows let in ample natural light in this Beacon Hill townhouse. This one is probably good for parties — there’s an enormous dining room that fits a 14-person dining table.

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Listed price: $11,900,000

Rooms: 5 bedrooms, 6 full bathrooms, 2 partial bathrooms

Square feet: 8,682

Price per square foot: $1,371

4. 314 Commonwealth Avenue

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You walk into this penthouse, and it’ll look and feel like a sleek art gallery. That’s what the designer and owner were going for — Zen. There’s a hot tub and a meditation nook on the first floor. Upstairs, there’s a deck with a hot tub and awesome views of the Prudential and John Hancock towers.

Listed price: $10,700,000

Rooms: 5 bedrooms, 3 full bathrooms, 1 partial bathroom

Square feet: 5,865

Price per square foot: $1,824

5. 14 Walnut Street

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This home comes with a large garden (questionable how useful it is in the winter months). The inside is designed with period detail, high ceilings, and some cool looking fireplaces.

Listed price: $10,000,000

Rooms: 6 bedrooms, 9 full bathrooms, 2 partial bathrooms

Square feet: 7,122

Price per square foot: $1,404

6. 410 Beacon Street

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Twenty first century comfort meets 19th century grandeur here. There’s a sky-lit rooftop mezzanine and the private garden off of the kitchen. Great views.

Listed price: $8,990,000

Rooms: 5 bedrooms, 5 full bathrooms, 3 partial bathrooms

Square feet: 9,107

Price per square foot: $987

7. 448 Beacon Street

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This condo in Back Bay’s Hooper Mansion has an elegant and sleek finish inside. Check out this bathroom: it looks to be all marble. The building offers a concierge, direct elevator access, parking, and a rooftop garden.

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Listed price: $8,500,000

Rooms: 4 bedrooms, 4 full bathrooms, 1 partial bathroom

Square feet: 4,057

Price per square foot: $2,094

8. 163-165 Marlborough Street

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Fun fact: This building used to belong to William Endicott, President Grover Cleveland’s secretary of war. Its four bedrooms and four and a half bathrooms span three levels. Lots of period detail throughout the interior design of the home.

Listed price: $6,995,000

Rooms: 4 bedrooms, 4 full bathrooms, 1 partial bathroom

Square feet: 4,856

Price per square foot: $1,440

9. 5 Byron Street

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This architectural gem was designed by the acclaimed Graham Gund. One of the decks is a Zen garden, and the other is a smaller garden off of the master suite.

Listed price: $6,950,000

Rooms: 3 bedrooms, 4 full bathrooms, 1 partial bathroom

Square feet: 5,323

Price per square foot: $1,306

10. 14 Chestnut Street

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Dine with a view: this triplex has a dining room opening up to a private deck. The large library is pretty incredible with all original woodwork.

Listed price: $6,895,000

Rooms: 8 bedrooms, 5 full bathrooms, 1 partial bathroom

Square feet: 7,308

Price per square foot: $943

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