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21 Chestnut Street Boston MA 02108

Boston, MA21 Chestnut Street, Beacon Hill

Sale Price$10,400,000The price has recently decreased

Sold

MLS Number 73337575

  • Residential
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 6,653

Exquisitely marrying historic Beacon Hill character with contemporary design, this 2017 gut renovated 4 bedroom + 2 office townhouse has been thoughtfully designed and expertly crafted! 6 levels of living connected by an elegantly draping oval staircase, this home boasts a parlor level eat in kitchen with concealed top-of-the-line appliances & storage, walk in pantry and breakfast room that are accessible to the enclosed garden. Ideal for formal entertaining the parlor also offers formal living with South facing views of Chestnut St and a large formal dining room. A 2nd floor double parlor features dual gas fireplaces, a fully equipped bar, floor to ceiling windows and a juliet balcony. A private office with access to the deck is also located on this level. A serene primary suite with dressing room, and ultra luxurious marble bath. Separate entrance with enormous mudroom, home gym, A/V system, concealed storage throughout, many custom built-ins, and excellent southern sun light!

Listed by Michael Harper of Coldwell Banker Realty - Boston

Listing Sold by Coldwell Banker Realty - Boston

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.67% last updated on 2026-08-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

430 Stuart Boston MA 02116

Boston, MA430 Stuart, Unit PH35D, Back Bay

Sale Price$10,400,000The price has recently decreased

Sold

MLS Number 73321306

  • Condo
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,297
  • Neighborhood Back Bay

Raffles Boston, this iconic 35-story tower seamlessly blends luxury residential living with impeccable 5 star hotel service, in the heart of Boston's Back Bay. This architectural marvel boasts an extensive suite of 16 world-class amenities, dining experiences led by Michelin-starred chef George Mendez and Boston’s own chef Jody Adams. Indulge in the renowned Guerlain Spa, a state-of-the-art fitness center with a 20-meter indoor pool.This exquisite 3 BR, 2.5-BATH PH offers breathtaking views spanning Downtown to the Harbor Islands, enhanced by a 324 sq ft terrace. The grand foyers cove lighting sets an elegant tone, leading to a spacious kitchen adorned with Modello Riservato Walnut cabinetry, Wolf & Subzero appliances, opulent marble countertops, backsplash & wet bar. The primary BR suite is a sanctuary, featuring 2 expansive walk-in closets, a spa-inspired 5 fixture ensuite bath, with an oversized soak tub on window. This home is a statement of sophistication, redefining luxury.

Listed by Manuel Davis of The Collaborative Companies

Listing Sold by The Collaborative Companies

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.67% last updated on 2026-08-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

29 Commonwealth Avenue Boston MA 02116

Boston, MA29 Commonwealth Avenue, Unit 6, Back Bay

Sale Price$10,350,000The price has recently decreased

Sold

MLS Number 72929815

  • Condo
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3,097
  • Neighborhood Back Bay

Introducing Haddon Hall, Boston's landmark building offering 9 luxury residences. Originally built in 1894 as apartments, the eleven-story structure was famous for being the first high-rise in Back Bay. With its storied history and unrivaled views, this is a once-in-a-lifetime opportunity to restore this building to its former glory. The spectacular views, large floor plate and exceptional location make Haddon Hall unique in the Back Bay housing market. Haddon Hall provides a luxury experience in a boutique building with the convenience of garage parking and a 24-hour concierge. The building’s location at the corner of Berkeley Street – on the sunny side of Commonwealth Avenue – affords it three sides of views on all floors, and four sides of windows on the higher levels. This floor-through residence is over 3,000 square feet on a single level of living offering 3-bedrooms, 3-bathrooms with at least 15 oversized windows making for a very light and spacious home.

Listed by Tracy Campion of Campion & Company Fine Homes Real Estate

Listing Sold by Campion & Company Fine Homes Real Estate

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.67% last updated on 2026-08-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

166 Edmunds Road Wellesley MA 02481

Wellesley, MA166 Edmunds Road

Sale Price$10,305,000The price has recently decreased

Sold

MLS Number 72829319

  • Residential
  • Bedrooms 4
  • Bathroom 8
  • Square Feet 9,656
  • High School Wms

One of Wellesley’s finest estates, this iconic Tudor-style residence sits proudly on an elevated 2.45-acre site in the sought-after Cliff Estates. Transformed by a spectacular Dream Team of design professionals including LDA Architects, Sea-Dar Construction, Landscape Architect Dan Gordon and New York designer Vivian Hedges, the result offers refreshing Contemporary design. The residence works beautifully for family activities or for entertaining. The internal views of this private property take in the spectacular swimming pool pavilion with a summer kitchen and expansive terraced lawn. Floor-to-ceiling windows running the length of the house affords abundant natural light that fills the house. The residence offers a principal bedroom suite with separate his and her dressing rooms and baths. The residence also includes a home office, library, exercise room, three-car garage, and lower level rec room. This is a property that your most discerning clients will want to experience.

Listed by Terrence Maitland of LandVest,Inc.

Listing Sold by Pinnacle Residential

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.67% last updated on 2026-08-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

28 Wendell Street Cambridge MA 02138

Cambridge, MA28 Wendell Street

Sale Price$10,300,000The price has recently decreased

Sold

MLS Number 73103993

  • MultiFamily
  • Bedrooms 27
  • Bathroom 18
  • Square Feet 12,204

*Offers on this property are due 5/16* Presenting 28 Wendell Street, a 12,204 SF, 3-story building located in the Harvard Square area of Cambridge, Massachusetts. 28F Wendell is a traditional apartment building featuring 14 market-rate studios. 28R Wendell is currently licensed for 13 rooms as a lodging house and college dormitory. Institutionally owned and maintained, and offered unencumbered by long-term lease commitments, this property presents immense value-add potential through the potential redevelopment to multifamily residential and condominium conversions, among other options and strategies. 28 Wendell Street is situated in one of the most esteemed locations in the world with unmatched access to many of the nation’s top colleges and universities, technology and bio-tech employers and many of the region’s best shopping and dining amenities. The property is located within a 10-minute walk of a MBTA Redline station, as well as Harvard and Lesley University.

Listed by Christopher Sower of Cushman & Wakefield

Listing Sold by Cushman & Wakefield

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.67% last updated on 2026-08-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

169-181 South Road Bourne MA 02559

Bourne, MA169-181 South Road, Wings Neck

Sale Price$10,300,000The price has recently decreased

Sold

MLS Number 72673958

  • Residential
  • Bedrooms 15
  • Bathroom 13
  • Square Feet 12,567

This unparalleled waterfront estate, a piece of Cape Cod history, consists of a 10-bedroom residence, a pool house, a guesthouse, a carriage house, native flora threaded with trails, private shoreline, colorful landscaping, a pool and spa, a tennis court, and views of the Wings Neck Lighthouse and the waters of Buzzard's Bay. The iconic Shingle-style main residence has been painstakingly rejuvenated, with particular attention paid to preserving the home's irreplaceable vintage style. A sense of enduring grandeur is apparent in deeply hued wide-plank hardwoods, French doors admitting glorious natural light, and classical moldings, millwork, and trim. The kitchen, baths, windows, fixtures, and mechanical systems have been thoughtfully updated. The grounds are lush with grass, flowering plants, and mature trees. Paths link each residence and lead to a tennis court with a viewing pavilion. Careful planning has rendered the estate self-sufficient, with three wells, underground propane tanks

Listed by Kerrie Marzot of Sotheby's International Realty

Listing Sold by Berkshire Hathaway HomeServices Robert Paul Properties

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

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Do not fill in this field:

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.67% last updated on 2026-08-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

269 Commonwealth Avenue Boston MA 02116

Boston, MA269 Commonwealth Avenue, Back Bay

Sale Price$10,280,000The price has recently decreased

Sold

MLS Number 73290917

  • Residential
  • Bedrooms 8
  • Bathroom 10
  • Square Feet 8,508

Introducing 269 Commonwealth Avenue, ideally located on the sunny side of the Commonwealth Avenue Mall with Newbury Street and Back Bay's finest shops and restaurants at its doorstep. Available for the first time in over sixty years, this magnificent residence offers 8,500 square feet of living space across five floors with an exceptionally wide floor plate. The property retains several original architectural details that have not been compromised, making for a unique and historic townhome in one of Boston's most desirable neighborhoods. Outstanding features include cathedral ceiling heights, intricate millwork, elegant fireplaces, and beautiful, oversized windows with stained-glass panels. The building is currently configured as 8 apartments with 3 full outdoor parking spaces. This storied home presents an exceedingly unique opportunity for a trophy single-family residence, luxury condo conversion, or investment property in the heart of Back Bay.

Listed by Tracy Campion of Campion & Company Fine Homes Real Estate

Listing Sold by Campion & Company Fine Homes Real Estate

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Ask A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.67% last updated on 2026-08-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

88 Garden Street Cambridge MA 02138

Cambridge, MA88 Garden Street, Harvard Square

Sale Price$10,250,000The price has recently decreased

Sold

MLS Number 73154281

  • Residential
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 7,588

The historic Asa Gray house is an iconic property showcasing meticulous preservation work and state of the art interior design, carpentry & modern amenities for a luxury lifestyle. Fine features throughout include custom mill work, opulent stonework, built-ins, many fireplaces, high-end appliances, Lutron lighting, a comprehensive security system, plus so much more. The home was remodeled with an emphasis on seamless indoor-outdoor entertaining, highlighted by the gorgeous eat-in chef's kitchen & a massive Brazilian wood deck that is accessed by three sets of glass French doors. The huge studio with a wet-bar, en-suite bath & 5 skylights can be used as a 1st floor guest suite, gym & more. Upstairs, the lavish primary suite showcases an expansive custom dressing room fully outfitted in custom cabinetry & a spa-like 4-piece bath with radiant heat as well as three additional bed/bath suites. Lower level contains a large media room, guest room & bath. An absolutely exquisite home.

Listed by Gail Roberts,Ed Feijo & Team, Edmund Feijo and Gail Roberts of Coldwell Banker Realty - Cambridge

Listing Sold by Barrett Sotheby's International Realty

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Ask A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.67% last updated on 2026-08-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

160 Peppercorn Lane Barnstable MA 02635

Barnstable, MA160 Peppercorn Lane, Cotuit

Sale Price$10,250,000The price has recently decreased

Sold

MLS Number 73197493

  • Residential
  • Bedrooms 5
  • Bathroom 8
  • Square Feet 7,504

Experience the ultimate lifestyle in this custom designed waterfront home with expansive views of Popponesset Bay, being offered with 166 Vineyard Road, an adjacent 5.8 acre waterfront buildable lot. This new and stunning residence, sited on 3.79 acres, incorporates elegant and functional architecture and offers 7,500 square feet of uniquely designed living space. This estate property, with western exposure to capture stunning sunsets and over 700' of water frontage, is a unique offering that will captivate the most discerning buyer.

Listed by Robert Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties

Listing Sold by Kinlin Grover Compass

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Ask A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.67% last updated on 2026-08-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

74-75 Viking Road Orleans MA 02653

Orleans, MA74-75 Viking Road

Sale Price$10,250,000The price has recently decreased

Sold

MLS Number 73244028

  • Residential
  • Bedrooms 8
  • Bathroom 7
  • Square Feet 6,597

Experience unparalleled tranquility at this legacy waterfront estate. Spanning two lots and seven acres, once part of the classic sailing camp Camp Viking, this exquisite private property is nestled in a serene and picturesque setting, offering multiple residences, a private dock, a boathouse, and a tennis/pickleball court. 995 feet of pristine beach frontage along Little Pleasant Bay and the Namequoit River, you'll enjoy excellent boating opportunities or simply a peaceful day on the beach. The primary residence features single-floor living with an open floor plan that exudes classic elegance, with fantastic indoor and outdoor areas for entertaining. Meticulously maintained, the estate includes multiple guest houses loaded with Cape Cod charm and beautifully landscaped grounds. This exceptional property is ideal for the discerning buyer seeking ultimate privacy in a luxurious,nature-filled environment. Seller welcomes offers with requests for buyer concessions.

Listed by The Eva Scott Group of Gibson Sotheby's International Realty

Listing Sold by Gibson Sotheby's International Realty

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Ask A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.67% last updated on 2026-08-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

50 Winsor Way Weston MA 02493

Weston, MA50 Winsor Way

Sale Price$10,200,000The price has recently decreased

Sold

MLS Number 72904167

  • Residential
  • Bedrooms 6
  • Bathroom 10
  • Square Feet 15,028
  • High School Weston Hs

Presenting 50 Winsor Way, a distinguished gated estate perched atop an elevated & secluded 2+ acre lot. Perfect for those with discerning taste, this exquisite 15,000+/- SF property, built by the reputable Thoughtforms, has been thoroughly restored to blend its traditional aesthetic with timeless modern flair. Experience the grandeur of its impeccably manicured picturesque grounds which boast expansive terraces, matured landscaping, and a luxurious swimming pool with stunning fountains. This resplendent property offers 6+ bedrooms, 7 full + 3 half baths, a 4 car garage, and a sprawling open floor plan crafted with every luxury in mind. A fully finished lower level features a recreation room, wine cellar, theatre room, wet bar, and more. On the 2nd floor, 4 bedrooms boast en suite bathrooms. This refined home is a one of a kind, quintessential colonial estate just waiting for you to call it home.

Listed by The Sarkis Team and George Sarkis of Douglas Elliman Real Estate - Park Plaza

Listing Sold by Blue Ocean Realty, LLC

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Ask A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.67% last updated on 2026-08-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

39 Union Park Boston MA 02118

Boston, MA39 Union Park, South End

Sale Price$10,200,000The price has recently decreased

Sold

MLS Number 73273806

  • Residential
  • Bedrooms 5
  • Bathroom 8
  • Square Feet 6,830

Impeccably renovated and restored, 39 Union Park is a sophisticated townhome that masterfully combines classical detailing with contemporary elegance. Spanning over 6,800 sqft across 6 levels, the home offers 5 beds, 6 full + 2 half baths, alongside multiple expansive living and dining spaces perfect for entertaining or family life. A grand parlor level offers formal spaces and a butler's pantry, while the upper family level features a custom kitchen with SubZero/Gaggenau appliances and a family room with rear deck. A full-floor primary suite provides unparalleled luxury and the top floor boasts two bedroom suites and laundry room. Lower levels offer a stunning guest suite, study/5th bed, and a garden-level entertainment area with full kitchen that seamlessly transitions to a tiered, landscaped garden. Designed with integrity and set in Boston's most vibrant neighborhood, 39 Union Park boasts generous proportions and views of the private park and fountains. Includes 1 garage pkg space.

Listed by Hanneman Gonzales Penney Gould, Chris Gonzales, John Gould, Nick Hanneman and Daisy Penney of Compass

Listing Sold by William Raveis R.E. & Home Services

{$office->Name}

Levi Real Estate Inc.
444 South Union Street
Burlington VT, 05401
Office: 444-444-4444

Do not fill in this field:

Do not fill in this field:

Ask A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.67% last updated on 2026-08-13

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLSPIN and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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