Middlesex, MA Homes

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  /33

  $5,950,000 Pending

  • 6 Beds
  • 8 Baths
  • 7,016 Sq Ft

  9 Woodman Rd, Chestnut Hill, MA 02467

  Nestled on a beautiful tree-lined street in Olde Chestnut Hill, this spectacular home offers an open and elegant floor-plan perfect for living and entertaining. Thoughtfully renovated in 2012, this home masterfully blends timeless architectural charm with modern amenities. High ceilings, abundant natural light, and beautifully crafted moldings and millwork create a sense of warmth throughout.The

  Taylor Blacker Luxury Residential Group, LLC

  9 Woodman Rd, Chestnut Hill, MA 02467
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  /29

  $5,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  15 Loveland Rd, Brookline, MA 02445

  Rare Rental Opportunity – Spacious 3BR Townhouse in Prime Hayes School DistrictWelcome to this beautifully maintained 2,000 sq ft townhouse located in the highly sought-after Hayes school district, just steps from Warren Field Park. This bright and spacious home offers a flexible layout ideal for families or professionals.Key Features:- 3 Bedrooms & 2.5 Bathrooms- Full

  15 Loveland Rd, Brookline, MA 02445
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  /36

  $2,010,000 Sold Jun 26, 2025

  • 2,527 Sq Ft
  • $795/SF
  • 8 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1930

  14 Meigh Rd, Chestnut Hill, MA 02467

  Perched on historic Chestnut Hill, one of Greater Boston’s most renowned and sought after neighborhoods, at the end of a private way, this delightful center-entrance colonial blends timeless charm with modern comfort. The 3rd floor offers views of the Chestnut Hill Reservoir and city skyline while hardwood floors, skylights, and central A/C enhance the bright, airy feel. 3+ bedrooms and 3.5 baths

  Matt Bless Thrive Realty Partners

  14 Meigh Rd, Chestnut Hill, MA 02467
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  /14

  Est $1,050,602 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,160 Sq Ft

  629 Hammond St Unit E215, Chestnut Hill, MA 02467

  629 Hammond St Unit E215, Chestnut Hill, MA 02467
• 

  

  

  /22

  $669,000

  • 1 Bed
  • 1 Bath
  • 786 Sq Ft

  35 Commonwealth Ave Unit 404, Chestnut Hill, MA 02467

  Enjoy the best of city and suburban living in this beautiful 1-bed, 1-bath condo in the heart of Chestnut Hill, Newton. Just 2 minutes walk from Boston College, top shopping, scenic trails, and golf courses, this home is in one of Newton’s most sought-after neighborhoods.The condo features a bright, open living space with large windows overlooking the golf course, a modern kitchen with stainless

  Kyle Chen LPT Realty, LLC

  35 Commonwealth Ave Unit 404, Chestnut Hill, MA 02467
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  /12

  $3,800 per month

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft
  • Condo for Rent

  629 Hammond St Unit E201, Chestnut Hill, MA 02467

  Highly desirable community of Chestnut Hill, Brookline. Hammondswood is a professionally managed elevator building that offers concierge andfitness facilities. 2009 Construction 2 Bed 2 Bath, 2 Deeded Garage Parking with extra storage and in-unit laundry. Open layout with a large livingroom and dining room area and 9" ceilings . Plenty of closet space throughout the unit. Ideally situated near

  Thomas Giblin Greater Boston Property Group

  629 Hammond St Unit E201, Chestnut Hill, MA 02467
• 

  

  /36

  $790,000 Sold Jun 25, 2025

  • 1,070 Sq Ft
  • $738/SF
  • 21 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2007

  35 Commonwealth Ave Unit 407, Chestnut Hill, MA 02467

  Welcome to this stunning two-bedroom, two-bathroom condominium located in a modern elevator building. Designed with an open floor plan, this bright and airy home is flooded with natural light from expansive windows throughout with beautiful views of the neighboring golf course. The spacious layout includes generous closet space.Enjoy the convenience of in-unit laundry, central air conditioning,

  Eileen Kibrick O Grady Coldwell Banker Realty - Brookline

  35 Commonwealth Ave Unit 407, Chestnut Hill, MA 02467
• 

  

  /23

  Est $3,842,486 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 5,292 Sq Ft

  20 Reservoir Rd, Chestnut Hill, MA 02467

  20 Reservoir Rd, Chestnut Hill, MA 02467
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  /38

  $2,800,000

  • 10 Beds
  • 4.5 Baths
  • 4,112 Sq Ft

  30 Ackers Ave, Brookline, MA 02445

  Exceptional two-family home with over 4,112 sq. ft. of living space, combining comfort and rental potential. Unit 1 features a newly renovated kitchen, one and a half baths with washer/dryer, 2 spacious bedrooms, and a sunroom perfect for a home office. The full basement offers expansion possibilities. Unit 2 is a renovated upper two-level unit with 5 bedrooms and 2 offices. The open floor plan

  Eileen Kibrick O Grady Coldwell Banker Realty - Brookline

  30 Ackers Ave, Brookline, MA 02445
• 

  

  /23

  $6,000 per month

  • 6 Beds
  • 3 Baths
  • 2,500 Sq Ft
  • Condo for Rent

  31 Heath St Unit 2, Brookline, MA 02445

  31 Heath St Unit 2, Brookline, MA 02445
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  /28

  $3,550,000 Sold Jun 20, 2025

  • 5,772 Sq Ft
  • $615/SF
  • 26 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 1920

  533 Hammond St, Chestnut Hill, MA 02467

  Welcome to the epitome of Chestnut Hill living.This renovated 5-bedroom, 5.5-bathroom single-family residence is a true architectural masterpiece, seamlessly blending modern elegance with timeless charm. This 5,772 sq ft. Brick English Colonial is tucked away on a serene 1/3 acre lot off a private road directly across from Longwood Tennis Club. As you enter, you're greeted by a welcoming foyer

  Jamie Genser Coldwell Banker Realty - Brookline

  533 Hammond St, Chestnut Hill, MA 02467
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  /24

  Est $1,565,765 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,055 Sq Ft

  630 Hammond St Unit 305, Chestnut Hill, MA 02467

  630 Hammond St Unit 305, Chestnut Hill, MA 02467
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  /37

  $599,000

  • 1 Bed
  • 1 Bath
  • 724 Sq Ft

  27-29 Commonwealth Ave Unit 5, Chestnut Hill, MA 02467

  Charming corner residence featuring double exposures of natural light! This sun-splashed one bedroom condominium offers gleaming hardwood flooring, recessed lighting and a kitchen that boasts granite countertops, newer stainless appliances and a breakfast bar with pendulum lighting. A spacious bedroom, ample storage, updated bath and in-unit laundry complete this turnkey gem. Heat & hot water

  Frank Celeste Gibson Sotheby's International Realty

  27-29 Commonwealth Ave Unit 5, Chestnut Hill, MA 02467
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  /21

  $7,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  28 Eliot St, Chestnut Hill, MA 02467

  FOR RENT - Stunning renovated single family home with fenced yard. FIRST FLOOR: living room, dining room, half bath. CHEF's kitchen with stainless appliances (WOLF stove, ASKO dishwasher), stunning Calcutta white QUARTZ island + countertops, hanging pendant lighting and surround sound speakers. SECOND FLOOR: 3 bedrooms + 2 full modern baths. Master bedroom with en suite spa-like bath.

  Mary Lochner Hurwitz Coldwell Banker Realty - Brookline

  28 Eliot St, Chestnut Hill, MA 02467
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  /27

  $1,194,000 Sold Jun 20, 2025

  • 1,638 Sq Ft
  • $729/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1910

  675 Hammond St Unit 3, Chestnut Hill, MA 02467

  Located in the heart of Chestnut Hill, this charming 3-bed, 2-bath home offers 2 levels of living with treetop views. The 1st floor features a spacious, fireplaced living room with soaring ceilings, a modern eat-in kitchen with updated appliances, sleek cabinetry, and a peninsula island-ideal for enjoying your morning coffee. The dining room provides a cozy space for meals and entertaining. This

  Scott Goldsmith Gibson Sotheby's International Realty

  675 Hammond St Unit 3, Chestnut Hill, MA 02467
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  /17

  Est $1,028,562 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  630 Hammond St Unit 209, Chestnut Hill, MA 02467

  630 Hammond St Unit 209, Chestnut Hill, MA 02467
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  /27

  $2,295,000

  • 5 Beds
  • 3.5 Baths
  • 2,692 Sq Ft

  30 Edge Hill Rd, Chestnut Hill, MA 02467

  Nestled in the heart of prestigious Chestnut Hill, this stately 5 bedroom, 3.5 bath Colonial residence offers timeless elegance & undeniable curb appeal. A gracious front entry welcomes you into a well proportioned living room, w/ a classic fireplace. Just beyond, an inviting family room provides views of lush, professionally landscaped gardens—an idyllic retreat for morning coffee. The home's

  Kennedy Lynch Gold Team Hammond Residential Real Estate

  30 Edge Hill Rd, Chestnut Hill, MA 02467
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  /20

  $4,100 per month

  • 4 Beds
  • 1 Bath
  • 1,800 Sq Ft
  • Condo for Rent

  759 Boylston St Unit 2, Chestnut Hill, MA 02467

  Available 9/1/25! Heat is included! Come and see this Large 4 or 5 bedroom 1 bathroom, with a bonus office, second-floor unit in Brookline Chestnut Hill. Located right on Boylston Street, Near Heath School! convenient to multiple grocery stores, Shops at Chestnut Hill, restaurants, and more! Easy highway access and easy commute to the Longwood medical area one bus the 60, 15-minute walk to The D

  759 Boylston St Unit 2, Chestnut Hill, MA 02467
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  /24

  $2,270,000 Sold Jun 19, 2025

  • 2,894 Sq Ft
  • $784/SF
  • 5 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1928

  41 Edge Hill Rd, Chestnut Hill, MA 02467

  Nestled in the heart of prestigious Chestnut Hill, this enchanting brick Center Entrance Colonial exudes timeless charm and classic elegance. Step inside to discover a gracious front-to-back living room adorned with a beamed ceiling and a stately fireplace. The formal dining room, graced with chair rail detailing, invites festive dinners and intimate celebrations alike. The sun-kissed eat-in

  Kennedy Lynch Gold Team Hammond Residential Real Estate

  41 Edge Hill Rd, Chestnut Hill, MA 02467
• 

  

  /31

  Est $998,676 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft

  630 Hammond St Unit 205, Chestnut Hill, MA 02467

  630 Hammond St Unit 205, Chestnut Hill, MA 02467
• 

  

  /21

  $1,099,000

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft

  321 Hammond Pond Pkwy Unit 103, Chestnut Hill, MA 02467

  Sunny and luxury 2 beds & 2 baths condo built in 2012 with open floor plan. Fabulous chef's kitchen equipped with cherry cabinets, stainless steel appliances and granite countertops. Private balcony overlooks a quiet landscaped yard. Master Bedroom has double walk-in closets and en-suite bath with marble walk-in shower and double vanity. Guest bedroom has large closets, modern guest bath. In-unit

  Dan Li Keller Williams Realty

  321 Hammond Pond Pkwy Unit 103, Chestnut Hill, MA 02467
• 

  

  /17

  $3,700 per month

  • 3 Beds
  • 1 Bath
  • 1,800 Sq Ft
  • Apartment for Rent

  51 Algonquin Rd Unit 1, Chestnut Hill, MA 02467

  Charming 3-Bedroom Apartment in Prime Chestnut Hill Location – $3,750/month | Available 9/1/25 Welcome to 51 Algonquin Road, Unit 1, a spacious and beautifully maintained 3-bedroom, 1-bath apartment ideally located in the heart of Chestnut Hill, just steps from the Boston College Green Line T stop and nestled alongside the 12th hole of the Newton Commonwealth Golf Course. This bright and airy

  Matt Mackin TKM Capital LLC

  51 Algonquin Rd Unit 1, Chestnut Hill, MA 02467
• 

  

  /20

  $2,650,000 Sold Jun 17, 2025

  • 3,430 Sq Ft
  • $773/SF
  • 2 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1943

  37 Randolph Rd, Chestnut Hill, MA 02467

  Ideally situated on an enchanting tree-lined block in Brookline's Chestnut Hill, this stately slate-roof, cedar-clad Colonial exudes classic architectural elegance. High ceilings, hardwood floors and exquisite millwork distinguish the main level living spaces, from the gracious entry foyer and expansive living room with a fireplace and built-in bookshelves to the luminous formal dining room. The

  Elisabeth Preis Compass

  37 Randolph Rd, Chestnut Hill, MA 02467
• 

  

  /28

  Est $1,229,225 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,515 Sq Ft

  630 Hammond St Unit 104, Chestnut Hill, MA 02467

  630 Hammond St Unit 104, Chestnut Hill, MA 02467
• 

  

  /22

  $3,800,000

  • 5 Beds
  • 4.5 Baths
  • 4,711 Sq Ft

  15 Glenland Rd, Chestnut Hill, MA 02467

  Experience luxury in this newly completed custom home by a renowned local builder known for exceptional craftsmanship & exquisite finishes. Located in the sought-after Brookline/Chestnut Hill area, this residence offers sophistication and comfort. The main level boasts an open concept layout with abundant natural light from expansive windows. An elegant fireplaced great room flows into a chef’s

  Rjp Sells Coldwell Banker Realty - Brookline

  15 Glenland Rd, Chestnut Hill, MA 02467
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  /18

  $2,999 per month

  • 2 Beds
  • 1 Bath
  • 999 Sq Ft
  • Condo for Rent

  1160 Boylston St Unit 26, Boston College, MA 02467

  This fantastic apartment is in a prime location to food shopping, specialty stores, dining and entertainment, as well as other consumer services. So is access to public transport, which footsteps away. On-street permit parking is available to residents. Back Bay, Longwood, many Universities and schools and the fabled Fenway Park are right outside your door. MBTA Accessible!

  1160 Boylston St Unit 26, Boston College, MA 02467
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  /39

  $4,650,000 Sold Jun 13, 2025

  • 5,410 Sq Ft
  • $860/SF
  • 17 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1880

  355 Hammond St, Chestnut Hill, MA 02467

  Nestled in one of Chestnut Hill, Newton's most sought-after neighborhoods, this residence was fully renovated in 2017 and offers an exceptional blend of classic elegance and modern convenience. The spacious and thoughtfully designed layout feature large windows that flood the rooms with natural light. The beautiful chef's kitchen has stone countertops, high-end appliances and ample storage. The

  Maggie Gold Seelig MGS Group Real Estate LTD

  355 Hammond St, Chestnut Hill, MA 02467
• 

  

  /19

  Est $1,305,446 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,545 Sq Ft

  630 Hammond St Unit 102, Chestnut Hill, MA 02467

  630 Hammond St Unit 102, Chestnut Hill, MA 02467
• 

  

  /22

  $3,849,000

  • 5 Beds
  • 3.5 Baths
  • 6,196 Sq Ft

  460 Heath St, Chestnut Hill, MA 02467

  Ideally situated on a private cul-de-sac in Chestnut Hill, this stunning architectural gem offers timeless elegance & modern luxury. Just minutes to the T, restaurants, coffee shops, & shopping, it boasts unobstructed park views from a Bluestone patio with a luxury outdoor kitchen and 8' gas fireplace perfect for entertaining. Inside, enjoy a sauna, home gym, wine cellar, billiards room, & a

  Samantha Stumpo New Brook Realty Group, LLC

  460 Heath St, Chestnut Hill, MA 02467
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  /8

  $2,750 per month

  • 1 Bed
  • 1 Bath
  • 9,999 Sq Ft
  • Apartment for Rent

  219 Commonwealth Ave Unit 5, Chestnut Hill, MA 02467

  1 bed- 1 bath - Delight in a state-of-the-art kitchen equipped with stainless steel appliances, granite countertops, and a convenient dishwasher. The interiors showcase gleaming hardwood floors, presenting a warm ambiance in a spacious layout. For your convenience, utilities such as heat, hot water, and gas are included in your rent. Beyond the comfort of the apartment, you'll benefit from a

  Yanis Benyamina Concept Properties

  219 Commonwealth Ave Unit 5, Chestnut Hill, MA 02467
• 

  

  /11

  $2,600,000 Sold Jun 12, 2025

  • 3,568 Sq Ft
  • $729/SF
  • 6 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1935

  21 Woodchester Dr, Chestnut Hill, MA 02467

  Surrounded by lush landscaping, this elegant Tudor in the desirable Ward School neighborhood combines timeless charm with contemporary features.Once inside the distinctive stone-arched entry, admire the classic foyer with its graceful staircase. Flow smoothly between rooms via arched doorways into the spacious step-down living room w/sculpted bas relief fireplace, elegant dining room, bright &

  Ilene Solomon Coldwell Banker Realty - Newton

  21 Woodchester Dr, Chestnut Hill, MA 02467
• 

  

  /22

  Est $4,915,624 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,895 Sq Ft

  19 Pine Rd, Chestnut Hill, MA 02467

  19 Pine Rd, Chestnut Hill, MA 02467
• 

  

  /41

  $1,225,000

  • 2 Beds
  • 2.5 Baths
  • 1,527 Sq Ft

  321 Hammond Pond Pkwy Unit 301, Chestnut Hill, MA 02467

  Perfectly situated third floor corner unit at Hammond Pond Place Condominium, a 12-year young 27-unit luxury building located just steps from Route 9 / Chestnut Hill shopping, dining, movie and outdoor recreation / activity...This 3rd floor corner unit has abundant windows on two sides and sliders from master bedroom to 350+ sq ft private terrace, allowing natural light to stream in...the terrace

  Mark Linsky At Home Realty, Inc.

  321 Hammond Pond Pkwy Unit 301, Chestnut Hill, MA 02467
• 

  

  /45

  $5,900 per month

  • 6 Beds
  • 3 Baths
  • 2,495 Sq Ft
  • Townhouse for Rent

  31 Heath St, Brookline, MA 02445

  NO BROKERS FEE!Spectacular, all-new, luxury gut renovation in 2019. No expense has been spared to create this homeowner-quality apartment. Ultra high-end finishes are throughout the apartment. The open-concept living room and dining area give way to a gourmet kitchen with stainless Bosch appliances, 5-burner gas range, quartz countertops, soft-close cabinets and drawers, and a spacious

  31 Heath St, Brookline, MA 02445
• 

  

  /25

  $2,750,000 Sold Jun 11, 2025

  • 3,819 Sq Ft
  • $720/SF
  • 4 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1926

  401 Heath St, Chestnut Hill, MA 02467

  Located in Chestnut Hill, this beautiful south facing Colonial Revival-style residence has a magnificent yard and gardens with a patio. The front entrance opens to an elegant foyer leading to an living room with exquisite original detail and fireplace, and conservatory with windows on all sides. The dining room, also with fireplace opens to a sun-filled sitting room. The updated kitchen

  Debby Belt Hammond Residential Real Estate

  401 Heath St, Chestnut Hill, MA 02467
• 

  

  /23

  Est $2,341,008 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 3,923 Sq Ft

  3 Glenoe Rd, Chestnut Hill, MA 02467

  3 Glenoe Rd, Chestnut Hill, MA 02467
• 

  

  /24

  $1,975,000

  • 6 Beds
  • 4 Baths
  • 3,088 Sq Ft

  752 Boylston St, Chestnut Hill, MA 02467

  Rare opportunity for investors/developers to own Chestnut Hill brick two family located near Longwood Medical area, Northeastern U, BU, BC, VA Medical Hospital and bustling shops/restaurants. Public transportation via bus 60 (Boylston/Route 9) is right outside and with close proximity to train (green line D train). Scenic Brookline Reservoir and Jamaica Pond nearby. Both units are currently

  Mary Lochner Hurwitz Coldwell Banker Realty - Brookline

  752 Boylston St, Chestnut Hill, MA 02467
• 

  

  /14

  $3,650 per month

  • 2 Beds
  • 1 Bath
  • 9,999 Sq Ft
  • Apartment for Rent

  219 Commonwealth Ave Unit 12, Chestnut Hill, MA 02467

  2 beds - 1 bath - Delight in a state-of-the-art kitchen equipped with stainless steel appliances, granite countertops, and a convenient dishwasher. The interiors showcase gleaming hardwood floors, presenting a warm ambiance in a spacious layout. For your convenience, utilities such as heat, hot water, and gas are included in your rent. Beyond the comfort of the apartment, you'll benefit from a

  Yanis Benyamina Concept Properties

  219 Commonwealth Ave Unit 12, Chestnut Hill, MA 02467
• 

  

  /40

  $4,500,000 Sold Jun 11, 2025

  • 5,744 Sq Ft
  • $783/SF
  • 67 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1914

  265 Dean Rd, Brookline, MA 02445

  Nestled between Fisher Hill & Chestnut Hill, 265 Dean offers the perfect blend of urban convenience & suburban comfort. This 6+ bedroom Colonial Revival was fully gutted in 2021 to meet modern family needs while preserving its historic charm. Expansive chef's kitchen features Sub-Zero & Thermador appliances. It opens to a bright family room with custom built-ins. A larger formal living room

  Jeff Hamilton Columbus and Over Group, LLC

  265 Dean Rd, Brookline, MA 02445
• 

  

  /20

  Est $1,363,910 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  695 Hammond St Unit 2, Chestnut Hill, MA 02467

  695 Hammond St Unit 2, Chestnut Hill, MA 02467

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