Chestnut Hill Homes for Sale

Location, Location, Location! 41,000+ square feet of land! Great opportunity to live in this unique contemporary home, add on or build your dream home on this site! The current home features 4 levels of living space with windows galore, many opening to patios, decks or balconies. 3 ensuite-bedrooms, 3 full and 1 half bath. The home offers 3 fireplaces adding warmth and a comforting glow. The

Bobby Morgenstern Gibson Sotheby's International Realty

Once-in-a-lifetime opportunity in Olde Chestnut Hill - this grand turn of the century victorian home is situated on almost 1 acre and offers mature trees and plantings, a large private back yard, and a separate 2+ car barn. Walking distance to many area amenities and public transportation, this elegant home is perfectly sighted away from the street and offers supreme privacy. Many restored

Michael Harper Coldwell Banker Realty - Boston

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 Serhant

This custom-designed Mid-Century Modern home, inspired by Frank Lloyd Wright, sits on a private 0.92-acre lot on coveted Singletree Road. A four-season breakfast room with 4 skylights fills the home with natural light and offers a seamless connection to the outdoors. The chef’s kitchen features top-of-the-line appliances, three ovens, two dishwashers, and lacquered burled wood cabinetry. Walls of

Sharon Katz Sky Realty, LLC

This elegant European-style country home is located in one of Old Chestnut Hill’s most desirable neighborhoods, ideal for modern family living and entertaining. The chef’s kitchen opens to a sun-filled family room and connects to both indoor and outdoor dining areas. The first floor also features a spacious living room and cozy library, both with fireplaces. Upstairs, the expansive primary suite

Michael & Conor Chamberlain Coldwell Banker Realty - Brookline

Beautifully restored 1900s French-style residence on an acre of land in Brookline’s coveted Fisher Hill. Over 6,000 sq ft of living space featuring 5 bedrooms and 4.5 bathrooms. Inviting foyer with fireplace & custom bookshelves, an impressive great room with 15’ ceilings & fireplace, an elegant living room with period details including a fireplace, and a dining room with French doors to a stone

The Duffy Group Compass

OPEN HOUSE Saturday May 9. 11 AM - 2PM and Sunday May 10. 1 PM - 2:30 PM. Well-located Chestnut Hill home set on a corner lot at the end of a dead-end street, offering privacy and a quiet residential setting. Convenient to Boston College, the Chestnut Hill Reservoir, and downtown Boston. The home includes 3 bedrooms and 3 bathrooms with a practical, well-proportioned layout. Main living spaces

Edmund Wong New Year Realty

**Call for Offers this week - Now vacant and easy to show.** Rarest of rare spacious 3-family home in prime Chestnut Hill location in Brookline, across from the Longwood Cricket Club and just moments to the MBTA Green Line and the premier shopping and dining at The Street at Chestnut Hill. Each unit offers a spacious three-bedroom layout with formal living and dining rooms and spacious kitchens,

Todd Glaskin Coldwell Banker Realty - Newton

Come see this sun-drenched condo with 1 bedroom, 1 bathroom and 1 deeded parking space located across from The Street in Chestnut Hill. Featuring stunning cathedral ceilings, beautiful woodwork and a lovely loft space perfect for a home office or second bedroom area, this inviting home offers both charm and functionality. Included in the purchase is an additional assigned storage unit. A large

Tina DiMonda Gibson Sotheby's International Realty

Experience modern luxury and timeless elegance at 321 Hammond Pond Pkwy, Unit 103 in Chestnut Hill, Brookline. This stunning condo features two spacious bedrooms, two elegant bathrooms, and a large open-concept living area with gleaming hardwood floors and high-end finishes. The gourmet kitchen dazzles with stainless steel appliances, granite countertops, and ample cabinetry, while the private

The Ridick Revis Group Compass

Classic brick-front, center-entrance Colonial in a well-established neighborhood. This 4 bed, 3.5 bath home is ready for a full renovation or potential gut, an ideal canvas to create your dream home. A gracious entry leads to a front-to-back living room with fireplace, formal dining room, and a family room with picture window overlooking a level backyard. Upstairs offers three spacious bedrooms

AJ Arstamyan Coldwell Banker Realty - Boston

Nestled in the sought-after community of Chestnut Hill, Brookline. Hammondswood is an upscale, professionally managed elevator building that offers concierge and fitness facilities. Pristine 2 Bed 2 Bath plus Den/Office, 2 Deeded Garage Parking with extra storage and in-unit laundry. Spacious, sun-filled unit with a 9" ceiling. Open layout with a large living room and dining room area that

Kate Kittipanthopas Lux Realty, LLC

Perfectly situated in the prestigious Chestnut Hill Historic District, this sun-drenched 1930s Tudor offers a seamless blend of timeless character and modern luxury. The open-concept layout features a granite kitchen with custom cabinets and a breakfast bar, flowing into an sun filled living area with classic coffer ceilings, a fireplace, and custom built-ins. Host elegant dinners in the formal

Karen Yu Phoenix Real Estate Partners, LLC

Welcome to 8 WHITE AVE, a 3-FAMILY Home in one of Brookline’s most desirable neighborhoods, offering 5 PKG SPACES & LETTERS OF COMPLIANCE !! This property offers the perfect blend of classic charm and modern convenience just minutes from Boston. The property features a thoughtfully designed layout with abundant natural light, spacious living areas, and timeless architectural details. Each of

The Caceda Team Coldwell Banker Realty - Lynnfield

Charming 1927 Tudor located in the highly desirable Chestnut Hill area of Brookline! This beautifull home offers timeless character with modern amenities. The first floor features a spacious living room with fireplace, formal dining room, eat-in kitchen, and a convenient half bath—perfect for everyday living and entertaining. The second floor includes four generously sized bedrooms, two full

Kevin Gingras Conway - West Roxbury

Sun-filled first-floor 2-bedroom residence in the Hammond Gardens community of Chestnut Hill. Set within a landscaped courtyard, this well-maintained home sits back from the direct traffic flow of Hammond Pond Parkway and Route 9. The layout features a spacious living room, a separate dining area, hardwood floors, an efficient kitchen, and in-unit laundry. The rear entrance opens to a covered

Plato Asadov Steve Bremis Realty Group

First time available in over 30 years. This Spanish Colonial estate was designed in 1905 by Chapman & Frazer and sits on 1.33 acres in Chestnut Hill, Brookline, MA. Approx 9,400 sq ft across four finished levels with 8 beds and 6.5 baths. Chef's kitchen with oversized island, pro appliances, and walk-in pantry opens to dining and a stone terrace. Formal living and dining rooms, quiet library, and

Paul Neavyn Gibson Sotheby's International Realty

Introducing Paine Estate, a grand Georgian Revival architectural treasure located in the highly coveted Chestnut Hill neighborhood of Brookline. This outstanding property has been extensively renovated, now combining traditional style and modern amenities with a thoughtful floor plan ideal for comfortable family living and grand entertaining. Exceptional features include a grand entry hall,

Tracy Campion Campion & Company Fine Homes Real Estate

Come fall in love with this storybook 5-bed, 3.5-bath Colonial Revival set on 0.3AC in Brookline’s Chestnut Hill. Built in 1926, this charming 4,028SF residence offers a layout tailored for modern living. Streaming southern sunshine, timeless architecture, 3 fireplaces, and oversized windows define the home. Welcoming entry connects the main living spaces. Gracious living room w/ fireplace and

Hilary Maddox Team Compass

Welcome to Hammond Pond Place! This bright and spacious 2 bed, 2 bath condo offers modern living in the heart ofChestnut Hill. The open floor plan features high ceilings, hardwood floors, and a sun-splashed living/dining area with asliding glass door that fills the space with natural light. The kitchen is equipped with stainless steel appliances, granitecounters, and an oversized breakfast bar —

Jiajia Xin LPT Realty, LLC

Nearly $700k below assessed value, this 4855 sq ft colonial in one of Brookline’s most sought after neighborhoods, and on one of its most desirable and picturesque streets, is a rare find. Create tremendous value with a smart renovation, or if preferred, build new now that the demolition hold has expired.Properties in close proximity are priced from $4-12m+ range. Survey, existing condition and

Jason Gell RE/MAX On the Charles

Welcome to the Covenant Residences on Commonwealth. This enticing corner one bedroom, one bathroom condo with 1 garage parking space and in-unit laundry, offers an open concept floor plan offers oversized windows that stream natural light. The home enjoys an open floor plan which is perfect for entertaining; fully applianced kitchen with a breakfast countertop,a generous living room showcases

Eric Holmes Meridian Realty Group LLC

Attention developers, builders, and end-users: Rare opportunity to create something truly special in one of Brookline’s most coveted Chestnut Hill neighborhoods. Sited on an expansive 18,000+ sq ft lot, this property offers exceptional potential for renovation, expansion, or new construction. The existing 3 bed, 2 bath ranch is sited on level land, with gentle slopes at the front and rear - ideal

The Gillach Group William Raveis R. E. & Home Services

Located on a quiet and desirable street in North Brookline, this exceptional Arts and Crafts home, designed in 1920 by esteemed architect Charles Donagh Maginnis as his own residence, ranks among the finest of its kind in the United States. Carefully restored, modernized, and meticulously maintained, the house displays outstanding craftsmanship from its era and is featured in several books on

Rachel Goldman MGS Group Real Estate LTD