The 20 Most Expensive Homes in the Boston Area

Boston is the capital of one of Massachusetts, and is one of the oldest cities in the country. It is also one of the most popular cities in the country. Millions of people visit the historic city every year, and more than 673,184 residents live there.

It is not only known for its rich history, but its many colleges and universities that attract over 350,000 students every year from all over the world. Boston has rated as the top 30 of the most economically powerful cities in the world.

The Greater Boston metropolitan area is the sixth largest economy in the U.S., and it is the 12th-largest in the world, encompassing $363 billion dollars.

There are a lot of wealthy people to be found in Boston, and with the wealth, comes expensive single family homes. If you have ever been interested in the city of Boston and curious about the kinds of homes the wealthy purchase in the city, then take a look at these. We have a list of the 20 most expensive homes in the Boston area.

20. Four Seasons Boston, #1205/1209, Boston – $7.35M

Yes, residents also live in the Four Seasons here in Boston, in living spaces that have been developed into condos, including this beautiful 3 bedroom, 3 bath, 3,300 sq. ft., personal living space that sells for $7.35 million. The residence also includes Four Seasons hotel services, including being greeted by a doorman, 24 hour Concierge services and valet parking.

There are a total of 95 residence that live in the Four Seasons. Their condos and the Penthouse are all located above the hotel and have amazing views of the city. Residence may also enjoy spending time in the Bristol Lounge, a landmark for the city, and will love being so close to some of the city’s best shopping and dining on Boylston and Newbury Streets.

19. 100 Beacon St UNIT 7, Boston, MA 02116 – $7.9M

Beacon Street is a main vein in downtown Boston. The street name was used for the fictional pizza parlor, Beacon Street Pizza, in the first season of the hit show, Two Girls and a Guy, and the address, 112 1/2 is the address of the fictional bar, Cheers. Beacon street is also the location of many high-end homes. 100 Beacon is a luxurious, full-floor residence that overlooks the city, with breathtaking city and Charles River views.

The renovated, four thousand-plus square foot living space was renovated with lavish details and has a natural, effortless flow from room-to-room which is perfect for entertaining, including the formal living and dining rooms which are separated by an exquisitely designed, double-sided fireplace.

The home also boasts of a beautifully crafted wood-paneled library, a den/media room, wet bar, and a high-end eat-in kitchen. Imagine looking out your bedroom window and seeing a beautiful city view.

That’s what this home gives you since the master suite was conceived with the best luxuries in mind, starting with having corner exposure for wonderful, picturesque views and natural light. The two custom walk-in closets are spacious, while the master bath boasts two walk-in’s and a gorgeous limestone bath. This home is one of the most expensive in Boston, at $7.9 million.

18. 274 Beacon #9R, Boston – $8.995M

For $8.995 million, you can own 274 #9, an iconic residence that is said to be a one-of-a-kind in that it is a 6,000 sq. ft. penthouse duplex where you have breathtaking views of the city.

Take the private elevator up to this luxurious home and you will be greeted by a beautiful formal entrance before entering into the rest of the open living areas of a formal living room, as spacious as a banquet room with vast ceiling heights, and floor-to-ceiling windows that let in lots of natural light and offer beautiful scenery.

There is also a fetching study designed with wood paneling, a wet bar and fire place. Upstairs is outfitted with more than 6 bedrooms and 6 full baths. The laundry room is also conveniently on the upper level along with ample storage areas. You will be living in luxury in this spacious and elegant home that is both extremely private, yet close to everything you need easy access to.

17. 310 Beacon Street #3, Back Bay Neighborhood – $9.2M

Another Beacon Street address that offers you a luxurious living space that combines both an elegance of modern and high tech living with this spectacular, and well-designed Penthouse. You are not short of beautiful views with the Charles River from inside the home, also from the gorgeous landscaped roof-deck where you can enjoy spending time admiring your city and skyline, day or night.

The beautifully designed, full kitchen is perfect for preparing meals for entertaining your guests while they retreat to the grand living room that features soaring vaulted ceilings and a dual fireplace.

The marble master bath is outfitted with a his and her dressing room, and is luxurious in so many ways. The property features a state-of-the-art gym, club room a total of 6 fireplaces for an element of coziness throughout the living space, and 3+ bedrooms. You feel pampered from the moment the doorman opens the door and invites you in.

16. 4 Marlborough St, Boston, MA 02116 $9.5M

You are only steps away from Boston’s Public Garden when you live at 4 Marlborough St., downtown Boston. One of the most expensive homes in Boston is 4 Marlborough St., and it is a single family home that gives you a high scale of entertaining space while offering a high standard of comfort and high-end Smart Home features.

You will enjoy the immense space this five bedroom, and five full baths, plus three half baths residency has to offer. Take advantage of the private exercise room and direct elevator access to your home that boasts a sky-lit top level and walk-out access to two separate private roof decks where you can admire your views. The home offers so many amenities that make you feel you are living the life of luxury from the moment you step in the doorway. At $9.5 million, how could it not?

15. 200-202 Beacon #1 &; 3, Boston – $9.995M

This is an extremely large living space that spans two buildings on Beacon and has so many features, you won’t believe your eyes. The architect was complete by Gur Grassi, while interior designs were put together by designer Bunny Williams. Some of the best features include the second floor, 40′ wide living room, dining room, spectacular kitchen, the large library and breathtaking views of The Charles River.
Every bit of the living space is perfect for entertaining, especially the garden patio and rooftop deck that allows you take it all in. On the parlor level there is a private street entrance and it opens to a grand entrance which leads to the master suite. In the suite area you have access to a library, washer and dryer, kitchenette, and the master bedroom that boasts exceptionally large closets, with a fireplace and gorgeous Jacuzzi.
The space doesn’t stop there. On the connected garden level, you have entry through a separate access and it consists of a bedroom, full kitchen, living room, laundry and a beautifully designed private stone and landscaped garden. Now wonder this home sells for $9.995 million.

14.1 Franklin St #3703-04, Boston – $10M

As far as you can see from this amazing home in the Millennium Tower, are 4,300 sq. ft. of living space with panoramic views that wrap around the Boston Common, Boston Harbor, and Charles River. This is a very unique floor plan that boasts 11.8 foot ceilings plus grand corner living room that is perfect for entertaining, especially with views like this.
There is also a state-of-the-art, full eat-in kitchen designed with Poggenpohl Cabinets and Calacatta marble counters. A breakfast bar gives you added meal preparation and sitting space, and the adjacent dining room dons SW views of the Park and River. Inside the marble spa master bedroom, you will feel pampered with all the luxurious amenities, including his and hers walk-in-closets plus more. 
There are three guest bedrooms, all with en-suite marble baths and for your enjoyment, take advantage of the Residence only club lounge with private dining, a screening room, library, billiard parlor, fitness center and valet parking. Listed as one of the most expensive home in the city of Boston, 1 Franklin sells for $10 million.

13. 274 Beacon St #PH, Boston – $10.495M

If a Penthouse view is what you want from your Boston home, you will love this elegant, 9th floor penthouse duplex that gives you gorgeous views of the Charles River and beyond. Inside the penthouse are beautiful parquet floors in the dining room and floor-to-ceiling windows, crown moldings and high ceilings that make the home feel so much larger and spacious.
There is a large, eat-in kitchen, 6 beds and 6 full baths, plus a separate 1 bed, 1 bath condo that is included. You can’t beat this luxurious way of living with all the amenities and easy way of life with no yard work to worry about, and in close proximity to all you need in downtown Boston. This is one of the most costly properties in Boston at $10.495 million.

12. 344 Beacon St, Boston – $11.2M

This amazing townhouse hasn’t been on the market in over a decade and is an iconic townhome on Beacon St., built in 1880 and 1881. When it was listed, it was added among the most expensive homes in Boston at $11.2 million. The spacious townhouse boasts 7,500 sq. ft. of living space with sweeping staircases leading to the multiple levels, along with an elevator, gorgeous stained glass windows, a two-car garage, wood-paneled library and elegant dining room.
You’ll feel warm and cozy with the seven fireplaces that are dotted throughout the residence and enjoy vast views of the city from the two separate decks that are accessed via the sky-lighted rooftop mezzanine. There is no other home like it, a true rare find to own this piece of history.


11. 257 Commonwealth Ave APT 3, Boston, MA 02116 – $11.250M

The perfect entertaining home, the home features the original public restrooms which give you ample facilities for large entertainment events or small. The 5,930 sq. ft. residence gives you plenty of living space and lots of beautiful features that make it one of the most stunning properties in the city, and worthy of its $11.250 million dollar price tag.

The home features thoughtfully designed rooms that let in an abundance of natural light. The private deck is a great place to spend quality time relaxing with friends and family. The kitchen has been updated and the details of the architecture include beautiful wood and plaster details, pocket doors, elevated ceilings, and crown molding.

The keyed elevator or the elliptical staircase will take you to the second floor where you will find the luxurious master bed and marble bath en-suite. No matter where you turn once you enter the Great Hall, you will be delighted in this prominent luxury Boston home.


10. Beacon Street’s 25 Beacon Street Penthouse, Boston – $11.5M

This beautiful 4,044 sq. ft. penthouse reached an asking price of $11.5 million and features 3 bedroom and 3 and 1/2 baths that you have direct elevator access to. The penthouse is designed with gorgeous windows throughout that allow for an abundance of natural light and views of the city, a spacious eat-in kitchen in white with bar area for extra seating, a combination living and dining area with fireplace, wine cellar, and gorgeous bath with unique double vanities on opposite walls and sumptuous soaking tub. You are right where you have easy access to what you need in the heart of downtown on one of the most iconic streets in the city, Beacon Street.


9. 274 Beacon St #9R/9F, Boston – $11.995M

Another beautiful Beacon property that sits on the list of the most expensive homes in Boston, is 274 Beacon St., #9/9F. This home is estimated at $11.995 million and with the exquisite details and features you get with the home, there is no wonder. The home is elegantly designed and perfect for entertaining with the flow of space in the 8,000 sq. ft. home.
You will find high-soaring ceilings, crown molding walls, detailed fireplaces, parquet floors and gorgeous floor-to-ceiling windows that leave you awe-inspired with the views of the Charles River, Cambridge, and further out yet. You will love what you have access to when you live on Beacon, if you ever decide you want to leave your stunning home.

8. The Whitwell, #6AB, 32 Derne St, Boston, – $12.750M

The former Suffolk University building is now home to a the Whitewell residence that sells for $12.750 million and is a six bedroom and seven full bath, plus two-half bath home. It offers you 6,270 sq. ft. of living space and is luxury living at its best. In the boutique condo building, this condo offers you 12-foot ceilings , plus a private landscaped terrace that are perfect for soaking in the panoramic views and skyline of Boston. If you want luxurious details with lots of space, natural light and gorgeous views, you will get it all at The Whitwell.

7. 7 Mount Vernon Place #7, Boston – $13M

This is a five story Greek revival, single family home and is waiting for the right owners to come in and take the shell interior and finish the exterior. The home was built in the 1830’s and is designed with a private garden and wrap around deck off of the parlor level. It is a beautiful residence that has just been needing the right owners to work with the current developer to complete the revival of restoring the exterior: new shutters, brick repointing, windows and more.
There is 7,500 sq. ft. of living space when you get inside and comes with a valet garage or full parking space out front. This is said to be a true gem and just needing it’s new outer refurbished look. At $13 million, it tops the list of most expensive properties in Boston.


6. 776 Boylston St PH2-E – $13.2M

776 Boylston is one awe-inspiring penthouses in the Boston area. It sits 14 stories above Back Bay and boasts 8,000 sq. ft. of living space where you get unobstructed views of Boston’s magnificent skyline and the Charles River. You can take-in the views from within the home through the floor-to-ceiling windows or enjoy the views from either of the two oversized terrace and two large decks which you an reach the outdoor oasis via the private elevator.

The large family room is conveniently located next to the beautifully updated kitchen with all new, updated appliances. This is one of the most exquisite and most expensive penthouses in the city of Boston and it shows, with a price of $13.2 million dollars.



5. 6 Arlington St #PH, Boston – $14.350M

The 13-story building was built in 1929 and is located in one of the most historic areas of the city. If you love living high up above the Public Garden, this gorgeous penthouse has all you could ever want in estate living. With 4,789 sq. ft. of living space, you get direct access with the private elevator up to your four-plus bedroom home. Enjoy the views all around from your spacious walk-out private terraces and all the services the building has to offer, including doorman service, Concierge service, fitness center and management that is on-site for your convenience. This is one of the most expensive properties that sells for $14.350 million.

4. 85 Pickney St, Boston – $14.95M

Pickney is in the heart of the historic Louisburg Square and 85 Pickney is one of the most exquisite homes in the area. It features beautiful views of the south light and is currently constructed as two residences, the parlor and garden site and the main home. The formal living room gives you a wonderful view of Louisburg Square and boasts soaring ceilings with gorgeous, detailed crown molding as well as a detailed fireplace.
Cathedral ceilings garnish the open kitchen and breakfast area. On the upper level, you will find the library that was designed with custom paneling and cozy fireplace. There are also two bedrooms and en-suite baths and laundry room on the floor.
On the master floor, take in the gorgeous river and square views, delight in the roof top family room and access to the two-tiered roof deck for more spectacular views and relaxation with friends and family. There is no end to all the amazing features of this home and you know it, just by looking at its price tag of $14.95 million.


3.197 Marlborough St, Boston, MA 02116 – $15M

The townhouse at 197 Marlborough St, is $15 million, the third most expensive property in Boston. It is an exquisite home that gives you elevator access to all six levels of the home and all the smart home technology you can imagine. It is a very up-to-date, modern convenience home with a beautifully designed chef’s kitchen and the informal dining on the second level.

The home features a private level where you’ll find five beds, five baths and 2- half baths, including the luxurious master suite, pus and separate garden suite. Other features include a home office, mudroom, oversized laundry room and sky-lit media room. You’ll love to relax in the hot tub and sip on your cocktail from the wet bar while taking in beautiful views of the city.

2. 40 Beacon St., Boston – $20M

Beacon Hill is known for its privacy and the exclusive properties that encompass it. It is also the location of the prominent gated estate at 40 Beacon. With the home you get beautiful views of the Boston skyline and Charles River, plus Back Bay. What 40 Beacon has to offer is an elegant home with a combination of 19th century detail and the distinguishing city of Boston.

The home was designed by architect Alexander Parris and was originally the home of businessman Daniel Parker. It was designed with a stunning ballroom that you don’t find in many other homes in the area, along with a wine cellar, private garden terrace and roof deck. For entertaining, you can’t beat the space and elegance of this home that is the second most expensive home in Boston, at $20 million dollars.

1. 150 Woodland Rd, Brookline – $195M

This mega mansion is the most expensive home in Boston and is owned by Reebok founder and former CEO, Paul Fireman. It is heads above the second most expensive home in the area and features eight beds and seven full baths, plus five half baths. It is located just five miles from downtown, yet sprawls out over 14 acres and is a total retreat from the city activity.

With 26,623 sq. ft. of living space, the mansion is the epitome of luxury from the moment you enter the Grand foyer, to every perfected detail in every room. The opulent limestone mansion was built in 1940 and sits on 1,200 feet of private ocean property and boasts a 1,500 species botanic garden of tropical plants and trees. Also featured on the grounds is a sports complex, tree house, four-car garage, and much, much more.

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