Brookline Homes with Colonial Style

Welcome to Brookline, Massachusetts—a charming town nestled in Norfolk County that beautifully blends suburban serenity with urban convenience. Just a stone’s throw away from downtown Boston, Brookline boasts a rich history, vibrant culture, and a welcoming community that makes it a sought-after destination for families, professionals, and retirees alike.

Brookline is renowned for its picturesque streets lined with lush trees, historic landmarks, and an array of local shops and eateries. The town is home to some of the best schools in the state, making it an ideal place for families looking to invest in their children's future. With its proximity to public transportation, residents enjoy easy access to the bustling heart of Boston while still relishing the tranquility of suburban life.

One of the standout features of Brookline’s real estate market is its stunning collection of Colonial-style homes. These timeless residences exude elegance and charm, characterized by their symmetrical facades, classic gabled roofs, and inviting porches. Many Colonial homes in Brookline have been meticulously maintained or thoughtfully renovated, showcasing original woodwork, hardwood floors, and spacious layouts that cater to modern living.

Whether you’re seeking a cozy family home or a stylish residence to entertain guests, Brookline’s Colonial-style properties offer a perfect blend of historical allure and contemporary comfort. Experience the warmth of this vibrant community and the beauty of its architectural gems—Brookline is not just a place to live, but a place to truly call home.

Newest Brookline Homes with Colonial Style

$1,295,000

3 Beds ⋅ 2 Baths ⋅ 73574339 MLS

A rare opportunity to own a beautifully updated home in one of Brookline’s most sought-after locations! This charming 3-bedroom, 2-bath residence offers a wonderful blend of classic character, modern updates, and versatile living space. The thoughtfully renovated kitchen features contemporary finishes and functionality, while both bathrooms have been beautifully updated for today’s lifestyle. Gleaming hardwood floors throughout add warmth and timeless appeal. A flexible bonus room provides endless possibilities as a fourth bedroom, home office, guest space, or creative studio—perfect for adapting to your needs. The inviting layout offers comfortable everyday living while providing plenty of space for entertaining. Location is truly exceptional. Situated just a few blocks from the Brookline Hills Green Line T station for quick access to downtown Boston and surrounding neighborhoods are easily accessible without sacrificing the charm and convenience of Brookline living. Enjoy close proximity to local to all the major hospital at Longwood Medical, shops, restaurants, parks, hospitals, and everyday amenities. Adding to the home's unique appeal, the property directly abuts Lincoln School, offering an uncommon level of convenience and connection to the surrounding neighborhood. With its prime location, renovated kitchen and baths, beautiful hardwood floors, flexible bonus space, and easy access to Boston, this is an opportunity you won't want to miss. Come see why 428 Boylston Street could be the perfect place to make home!

428 Boylston St, Brookline

Listing courtesy of Listing Agent: Victor Divine from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$3,995,000

4 Beds ⋅ 5 Baths ⋅ 73573585 MLS

Welcome to this stunning center-entrance Colonial in Brookline's Chestnut Hill estate area, set on a level half-acre lot. This expansive home features 4+ bedrooms, 4 full and 1 half baths & offers over 4,895 square feet across three finished levels. The foyer opens to a fireplaced living room and a formal dining room that seats 12. The Chef’s kitchen features a Wolf range, Sub-Zero refrigerator, double wall ovens including steam, Cove dishwashers, two sinks, custom cabinetry & granite counters. A library with built-ins cabinetry sits off the dining room & kithcen. The family room, with gas fireplace opens through French doors to a bluestone patio and a broad, fenced, level yard. Upstairs, the primary suite includes a private balcony, Carrara marble bath, dressing area, and two walk-in closets. Three additional bedrooms and two full baths & laundry complete the floor. The lower level consists of a media/playroom, gym, wet bar, beautiful full bath with glass enclosed shower + another set of laundry. Central air & Sonos throughout, EV charging & 2-car garage. Close proximity to the D Line at Chestnut Hill, shops and restaurants at The Street at Chestnut Hill, Soule Playground, and Dane Park.

17 Glenoe Rd, Brookline

Listing courtesy of Listing Agent: Jamie Genser from Listing Office: Coldwell Banker Realty - Brookline.

$5,150,000

4 Beds ⋅ 5 Baths ⋅ 73573266 MLS

An elegant English-inspired Gothic Revival residence in Brookline’s coveted Fisher Hill neighborhood, distinguished by steep slate roofs, dramatic gables and arched architectural and copper details. Designed for Mrs. Harold Hammond by noted architects Kilham, Hopkins & Greeley, whose work also includes the Devotion School (Florida Ruffin Ridley School) and Brookline High School (source: Brookline Preservation Commission), this stately home offers 5,744 sq. ft. of living space across four finished levels, with 4 bedrooms, 3 full and 2 half baths, 5 fireplaces and an attached 2-car garage.The main level features a welcoming kitchen with convenient side entry, dining room with fireplace, gracious living room with fireplace, a light-filled sunroom overlooking the serene garden, two offices and powder room. The exceptional walk-out garden level is designed for both everyday living and entertaining, anchored by a dramatic two-story family room with fireplace, custom built-in bookcases, wet bar, floor-to-ceiling windows and French doors opening to a stone patio and private backyard. A wine cellar and lounge, exercise room, powder room and direct garage access complete this level.Upstairs, the generously scaled primary suite features a fireplace, walk-in closet and private outdoor balcony. Two additional bedrooms, a full bath and laundry complete the second floor. The finished top floor offers two spacious and versatile rooms—ideal for bedrooms, offices, hobbies or recreation—along with a full bath and abundant storage.Set on .35 acres, the beautifully landscaped private grounds offer mature specimen trees, stone walls, lawns and peaceful spaces for outdoor dining, entertaining and play. Meticulously maintained and thoughtfully updated over the years, the home combines period character with comfortable, move-in-ready living and exceptional storage throughout.A quiet and secluded setting on a tree-lined street, yet remarkably convenient to Washington Square, Cleveland Circle, schools, parks, public transportation (C & D lines), shopping and Boston.

67 Hyslop Rd, Brookline

Listing courtesy of Listing Agent: Ingvild Brown from Listing Office: Keller Williams Realty.

$1,199,000

2 Beds ⋅ 3 Baths ⋅ 73572983 MLS

Tucked away in a peaceful setting, yet just moments from Brookline Village, this charming and beautifully maintained condominium lives like a single-family home. The welcoming first level offers an open yet cozy layout with living and dining areas, a well-appointed kitchen, and a powder room. High ceilings, beautiful wood floors, and large windows fill the space with natural light and enhance its inviting character. The second floor is comprised of a generously sized bedroom and an updated marble-accented bathroom with a double vanity. On the third floor, you’ll find a second bedroom along with a bonus area ideal for an office, exercise space, reading nook, or creative retreat. The finished lower level provides excellent guest accommodations complete with a lovely full bathroom. A standout feature of this special home is the private 400+ sf patio—an exceptional outdoor space for relaxing, entertaining, or enjoying a morning coffee. Secure rental parking is just outside the front door.

50 Cameron Street, Brookline

Listing courtesy of Listing Agent: Lynette Glover from Listing Office: Hammond Residential Real Estate.

$2,765,000

5 Beds ⋅ 4 Baths ⋅ 73572599 MLS

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 built-ins flows into bright conversatory. Opposite is a family room with fireplace, which opens to a bright dining room. Classic butler’s pantry connects to the kitchen. With ample counter space and a cozy eat-in area, the kitchen serves as the heart of the home with direct access to deck and yard. Mudroom and half bath complete floor. Upstairs has bright en-suite primary, 4 additional bedrooms, office, and 2 full baths. Walkout lower level with playroom and laundry. Attached garage. Landscaped grounds create a true sense of privacy. Close to “The Street”, top schools, and Green D line train.

401 Heath Street, Brookline

Listing courtesy of Listing Agent: Hilary Maddox Team from Listing Office: Compass.

$1,790,000

4 Beds ⋅ 3 Baths ⋅ 73572511 MLS

Captivating colonial tastefully designed for elegant entertaining and comfort in mind. Privacy + nature abound in this 4 bedrooms, 3 bathrooms + 2450 square feet of refined living space in a premier Chestnut Hill location. Near Baker Elementary school (grades K-8) + close proximity to Putterham Shops, tennis, golf, wildlife sanctuary, Longwood Medical Area, Arnold Arboretum + Jamaica Pond. First floor has living room with wood burning fireplace, family room, bedroom with full bath + access to expansive outdoor deck. In the heart of the residence is a beautifully renovated kitchen with custom white shaker cabinets, sleek black granite countertops, stainless steel appliances + generous center island. Upper level has a sprawling primary bedroom suite complimented by majestic sunset views + an abundance of attributes such as walk-in closet, separate sitting area + spa-like bath with dual sink vanity, glass enclosed shower + soaking tub/jacuzzi. Additional finished lower level provides versatile space for a fitness gym, home theatre or home office to meet today's evolving lifestyle needs. One car garage, one carport + plenty of additional driveway parking make this an ideal residence to call home.

133 Wolcott Road, Brookline

Listing courtesy of Listing Agent: Mary Lochner from Listing Office: Coldwell Banker Realty - Brookline.

$2,999,000

4 Beds ⋅ 4 Baths ⋅ 73565107 MLS

Located on coveted Fisher Hill, this charming residence set on 14,550 square feet of beautifully landscaped grounds, offers thoughtfully designed modern updates, newer systems, and the convenience of an attached garage. The gracious main level features a welcoming living room with fireplace, formal dining room, powder room, and a chef’s eat-in kitchen featuring custom cabinetry outfitted with a Thermador gas cooktop and warming drawer, GE Monogram double ovens, two Bosch dishwashers, two sinks, and a Sub-Zero refrigerator. The kitchen opens to a spacious, sun-filled family room with skylights and direct access to the lush, private backyard. A flag stone patio and gas hookup for grilling create an ideal setting for relaxed indoor-outdoor living. The second level features a generous primary suite with a newly renovated en-suite bath, complete with luxurious heated radiant floors and a skylight, along with three generous closets. Three additional well-proportioned bedrooms with substantial closet space and a full bath complete this level. The finished lower level provides versatile flex space for a gym, office/guest accommodations, playroom/den, along with a full bath, laundry area with refrigerator/freezer, and extra storage, all with 1- car garage access and additional 2 outdoor spaces. Ideally situated near Runkle School, Brookline High School, the Longwood Medical Area, Chestnut Hill Reservoir, and the MBTA Green Line C and D branches, with easy access to nearby shops, restaurants, and Route 9.

52 Clinton Road, Brookline

Listing courtesy of Listing Agent: Maxine Malka Freedman from Listing Office: Hammond Residential Real Estate.

$14,995,000

6 Beds ⋅ 8 Baths ⋅ 73537408 MLS

Designed to be admired and built to be enjoyed, 33 Sears Rd is a custom residence set on 1.6 acres of manicured, private grounds. The home makes an immediate statement with a grand two-story foyer that introduces soaring ceilings, refined detailing, and beautifully scaled living spaces throughout. Built by one of Boston's premier female builders, the craftsmanship is evident in every threshold, finish, and room proportion. The open-concept main level was thoughtfully designed to offer grand room sizes without sacrificing warmth. A custom chef's kitchen appointed with top-tier appliances anchors the heart of the home, complemented by a separate, fully equipped prep kitchen. The primary suite features a dramatic two-story walk-in closet, a rare offering that quietly separates this residence from others on the market. Elevator infrastructure is already in place. Outdoor living is equally compelling, w/ ample acreage to accommodate a future pool, sport court, or other lifestyle amenities.

33 Sears Rd, Brookline

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.

$8,200,000

6 Beds ⋅ 9 Baths ⋅ 73526856 MLS

Set on over 1.2 acres with a 1.62-acre experience via a neighboring easement, this exceptional Chestnut Hill estate offers a tranquil oasis on one of the area’s most coveted and secluded streets. Originally built in 1900 and thoughtfully renovated over time, the residence spans more than 9,300 square feet with six bedrooms, six full bathrooms, and three half bathrooms. Its richly detailed living spaces were designed for both elegant entertaining and everyday comfort. Gracious formal rooms, soaring ceilings, and exquisite millwork overlook beautifully landscaped grounds featuring a heated, in-ground pool, a basketball court, and ample parking. Once home to Alvan T. Fuller, the 50th Governor of Massachusetts, the property carries remarkable historic provenance. The grounds were originally designed by Frederick Law Olmsted, further contributing to the property’s timeless character. This is a rare opportunity to own a historic estate of this scale in an unbeatable location.

40 Singletree Rd, Brookline

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$3,495,000

5 Beds ⋅ 5 Baths ⋅ 73517349 MLS

Handsomely poised overlooking the Brookline Reservoir and nestled back from the street, this distinguished period home offers four finished levels and seasonal water views on nearly a half-acre with bluestone patio and pool. The gracious entry opens into a grand foyer flanked by sun-drenched rooms. Bay windows in the living room, dining room, family room, and primary suite frame reservoir and garden views. Four fireplaces, high ceilings, crown molding, and custom woodwork throughout. Well-equipped kitchen for serious cooks with breakfast area and counter seating. Private first-floor study. Enchanting screened porch access the dining and living rooms for al fresco dining. Second floor: three bedrooms, two baths, and a primary suite with large dressing room, ensuite bath, and private deck. Third floor: two additional bedrooms and full bath. Lower level: exercise room, sauna, wine cellar and lav. Two-car garage. Minutes from Chestnut Hill shopping, Longwood Medical Area, and universities.

68 Dudley Street, Brookline

Listing courtesy of Listing Agent: Friedler / Marchant Living Group from Listing Office: Hammond Residential Real Estate.

$5,950,000

4 Beds ⋅ 4 Baths ⋅ 73508634 MLS

Unique opportunity to have your dream home built in the heart of Fisher Hill! 11,338 sf level lot with foundation and plans for a 4 bedroom, 3.5 bath classic brick colonial home with 4,825 square feet of space (on 3 levels) and a 2 car detached garage with shed. Gourmet kitchen opens to the den, dining and living room. First floor covered porch and terrace, perfect for al fresco dining. Exceptional location, close to Fisher Hill Park, Runkle School, public transportation, shopping, dining, an easy commute to Boston, Longwood medical area and Cambridge. Modifications to the plans subject to review and approval. Buyer to verify all information. Photos are renderings.Also available as a lot with foundation for $2,950,000.

9 Willard Road, Brookline

Listing courtesy of Listing Agent: Celine Sellam from Listing Office: Coldwell Banker Realty - Brookline.

$14,850,000

6 Beds ⋅ 8 Baths ⋅ 73507123 MLS

Privately set off Warren St, this exceptional Brookline estate spans over 3.6 acres of beautifully landscaped grounds and over 9,000 SF across four levels, with 6 bedrooms, 6 full and 2 half baths. A striking entry with a sweeping staircase leads to expansive, light-filled living and entertaining spaces rich with charm and detailed moldings. The main level features a mix of formal and informal spaces, multiple offices, and a beautifully designed kitchen with high-end appliances, custom cabinetry, and an eat-in dining area overlooking the grounds. Upstairs, the primary suite includes a luxurious bath and generous dressing rooms, along with five additional bedrooms, family room, and laundry. The serene third floor offers flexible space for a gym, studio, or additional living. Outside, the grounds are unmatched - a pond, patios, firepit, and hot tub perfect for entertaining and everyday living. A one-of-a-kind offering in one of Brookline's most sought-after neighborhoods.

280 Warren St, Brookline

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

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