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

Brookline’s prestigious Chestnut Hill neighborhood and within one of the town’s top-rated school districts, this 1899 estate seamlessly combines timeless architecture with a full modern renovation. The home offers 6,292 square feet of refined living space across three finished levels, featuring nine bedrooms, four full and three half baths, and two well-appointed kitchens ideal for entertaining

Andrew Haddad Northeast Development & Investment, Inc.

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 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. The formal

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

Experience luxury in this newly completed custom home by a renowned local builder. Ideally situated in the highly desirable Brookline/Chestnut Hill neighborhood, this residence offers the perfect blend of upscale living and everyday comfort. The sun splashed main level features an open & airy layout with soaring ceilings & oversized windows that fill the space with natural light. An elegant

Rjp Sells Coldwell Banker Realty - Brookline

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

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

Step into this stunning, completely renovated contemporary condo that perfectly blends designer style with serene golf course views. This is not your typical cookie-cutter unit; every inch has been transformed within the last five years. The open floorplan features engineered hardwood floors throughout, a modern kitchen with shaker cabinets, quartz countertops, subway tile backsplash, and gas

Paul Shao REMAX Executive Realty

Bright and inviting, this move-in ready home sits at the end of a quiet cul-de-sac, offering privacy, and a peaceful setting. Minutes to bus lines and the Green Line for easy access to Longwood, Harvard Square, and downtown Boston.This 4-bed, 3.5-bath home features an open layout with a spacious living room with fireplace, dining area, and updated kitchen with stone countertops and stainless

Celine Sellam Coldwell Banker Realty - Brookline

Elegant brick center-entrance Colonial on a desirable tree-lined street, offering 10 rooms, 4–5 bedrooms, and 4.5 baths. Front-to-back living room with fireplace and great natural light, formal dining room, and eat-in kitchen open to a large family room. First-floor study/office. Central air. Two-car garage plus additional storage garage that accommodates a small car . The lower level includes a

Eileen Strong O'Boy Hammond Residential Real Estate

If you're dreaming of effortless living in a vibrant neighborhood, this Chestnut Hill condo will steal your heart. Picture mornings on your private deck overlooking lush landscaping, afternoons strolling to local favorite spots at The Street, and evenings enjoying nearby restaurants or a newly released movie. With a bright, open layout, this 2-bed, 2-bath condo features sleek wood floors, a

Cheryl Cotney 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

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 beautifully situated 3-Family Home in one of Brookline’s most desirable neighborhoods. 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 units has its own individual

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

Elegant Colonial ideally located between the coveted Fisher Hill and Chestnut Hill neighborhoods. This classic home offers gracious living spaces including a welcoming living room with fireplace, formal dining room, and a charming butler’s pantry leading to the eat-in kitchen. The kitchen opens to a spacious sun-filled family room with vaulted ceilings and access to a sunroom, stone patio, and

Celine Sellam Coldwell Banker Realty - Brookline

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

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

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