Vintage homes for sale & real estate in Chestnut Hill, MA

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OPEN SUN, 12:30PM TO 1:30PM

ABOUT THIS HOME
Vintage Home for sale in Chestnut Hill, MA:
New to Market! Don’t miss this rare opportunity to own a beautifully maintained, sun-filled 3BR, 1.5BA condo in one of Brookline’s most sought-after locations. This inviting home features an open and airy floor plan with high ceilings, oversized windows, and abundant natural light throughout. Well-appointed kitchen boasts maple cabinetry, granite countertops, stainless steel appliances, gas cooking, and a spacious island with bar seating—perfect for both everyday living and entertaining. Additional highlights include two deeded side-by-side parking spaces (a true rarity in Brookline), low condo fees, new siding, roof, and gutters, fully deleaded. Enjoy an unbeatable locati

$799,000

3 beds1.5 baths1,087 sq ft

55 Reservoir Rd #2, Chestnut Hill, MA 02467

High ceilings • Oversized windows • Maple cabinetry

ABOUT THIS HOME
Vintage Home for sale in Chestnut Hill, MA:
Chestnut Hill, Brookline. Designed in 1905 by Chapman & Frazer, this Spanish Colonial estate unites house and garden across approx 1.3 acres. About 9,400 sq ft on four finished levels with 8 beds and 6.5 baths. Chef’s kitchen with oversized island, walk-in pantry, and pro appliances opens to dining and a stone terrace. Formal living and dining pair with a quiet library and a large family room. The serene primary suite offers a spa bath and custom dressing closets. Upper levels add flexible rooms for guests, work, and play. The finished lower level provides media, fitness, recreation, and storage. Courtyards, terraces, and defined garden rooms create a private setting. Historic 1

$8,750,000

8 beds6.5 baths9,400 sq ft

142 Crafts Rd, Chestnut Hill, MA 02467

Large family room • Quiet library • Stone terrace

ABOUT THIS HOME
Vintage Home for sale in Chestnut Hill, MA:
SPACIOUS AND BRIGHT CONDO WITH TERRIFIC LOCATION!! This home offers a welcoming entrance into a spacious living room with a bank of windows and gleaming hardwood floors. The living room leads to a well equipped kitchen with ample counterspace and cabintry, built-in micro and outdoor access. A spacious bonus room off of the kitchen can be a dining room, office or (add a door) a second bedroom! The primary bedroom is well-proportioned with hardwood floors and offers a comfortable and private retreat. The art deco bathroom features original black and white tile work. The covered porch off the kitchen provides an inviting outdoor space, allowing you to enjoy the beautifully landscaped grounds.

$410,000

1 bed1 bath710 sq ft

33 Hammond Pond Pkwy #2, Chestnut Hill, MA 02467

Covered porch • Welcoming entrance • Ample counterspace

ABOUT THIS HOME
Vintage Home for sale in Chestnut Hill, MA:
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, elegant formal sunken living room overlooking the picturesque gardens, fireplaced dining room, gourmet chef's kitchen, family room, handsome wood paneled library and an expansive great room. 6 bedrooms include the luxurious primary suite complete with separate bathrooms and dressing rooms and balcony. Ad

$19,000,000

7 beds9.5 baths13,343 sq ft

1014 Boylston St, Chestnut Hill, MA 02467

Grand entry hall • Sunken living room • Expansive great room

ABOUT THIS HOME
Vintage Home for sale in Chestnut Hill, MA:
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 five 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 terrace. House features a chef’s kitchen with high-end appliances and two spacious first-floor primary suites offering serene terrace views. The second floor has two bedrooms and a full bathroom. There is also a fifth bedroom with private entrance, perfect for au pai

$5,000,000

5 beds4.5 baths6,419 sq ft

540 Chestnut Hill Ave, Brookline, MA 02445

Inviting foyer • Acre of land • Serene terrace views

Property at 3 Glenoe Rd, Chestnut Hill, MA 02467, 4 beds, 4 baths

$2,295,000

4 beds4 baths4,855 sq ft

3 Glenoe Rd, Chestnut Hill, MA 02467

Property at 88 Essex Rd, Chestnut Hill, MA 02467, 5 beds, 6.5 baths

$9,700,000

5 beds6.5 baths8,750 sq ft

88 Essex Rd, Chestnut Hill, MA 02467

Property at 59 Ackers Ave #1, Brookline, MA 02445, 2 beds, 1 bath

$825,000

2 beds1 bath1,128 sq ft

59 Ackers Ave #1, Brookline, MA 02445

Property at 85 Gate House Rd, Chestnut Hill, MA 02467, 5 beds, 5.5 baths

$4,375,000

5 beds5.5 baths8,000 sq ft

85 Gate House Rd, Chestnut Hill, MA 02467

Property at 27-29 Commonwealth Ave #5, Chestnut Hill, MA 02467, 1 bed, 1 bath

$580,000

1 bed1 bath724 sq ft

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

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ABOUT THIS HOME
Vintage Home for sale in Chestnut Hill, MA:
This stunning ten-room residence offers 3,838 square feet of elegant living space in the heart of Washington Square. Gut renovated down to the studs by Rincon Development, the home seamlessly blends modern amenities with exquisite period details. The open floor plan is enhanced by soaring ten-foot ceilings and top-of-the-line finishes throughout. Featuring five bedrooms and four bathrooms, the property includes a luxurious primary bedroom suite with a vaulted ceiling, multiple closets, and a spa-inspired bathroom. Within the primary suite is a lofted room that can be an office, gym, private den area. Additional highlights include beautiful outdoor space, three-car parking and radiant heat o

$3,150,000

5 beds4.5 baths3,838 sq ft

757 Washington St Unit 2 - PH, Brookline, MA 02446

Gut renovated • Open floor plan • Period details

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Chestnut Hill, MA:
Beautifully renovated grand Victorian combining modern luxury with timeless architectural character. Sun-filled open layout with high ceilings, custom millwork, and a designer kitchen with high-end appliances. The home offers 5 bedrooms, 4 full bathrooms, 2 half bathrooms, a home office, playroom, and den across three spacious levels. Corner lot setting with a circular driveway in front and a second driveway in back. Prime Newton Corner location close to schools, parks, shops, transit, and major commuter routes.

$2,890,000

6 beds5 baths6,420 sq ft

686 Centre St, Newton, MA 02458

Designer kitchen • Open layout • Circular driveway

ABOUT THIS HOME
Vintage Home for sale in Chestnut Hill, MA:
Experience exceptional value in this beautifully refreshed top-floor penthouse in Brookline, where contemporary style blends seamlessly with comfort. This renovated 3-bedroom, 3-bath home offers an impressive layout enhanced by warm, natural light from its desirable south-facing exposure. The open living area welcomes you with a bright, airy feel perfect for relaxing or hosting. A standout chef’s kitchen features refined quartz counters, a generous island, and premium GE Café appliances, including a double oven ideal for everyday meals or entertaining. Each bathroom is thoughtfully designed with spa-like elements, heated smart mirrors, and elegant tile detailing. Modern touches

$1,275,000

3 beds3 baths1,814 sq ft

37 Englewood Ave #3, Brookline, MA 02445

Quartz counters • Top-floor penthouse • Double oven

ABOUT THIS HOME
Vintage Home for sale in Chestnut Hill, MA:
A one of one in Brookline – immerse yourself in this sun-filled penthouse that seamlessly blends timeless character with modern luxury. Upon entering, one is instantly impressed by the ultra-high ceilings, grand staircase, exposed brick wall, and modern lighting fixture. The open-concept layout provides a spacious living, dining, and kitchen area. The fully renovated kitchen features an oversized island, stainless steel appliances, quartz countertops, and a wine fridge. The recently renovated bathroom features an oversized steam shower, timeless vanity, and in-unit laundry. The two bedrooms offer custom closets, high ceilings, and storage space. A private roof deck—complete with

$1,157,000

2 beds1 bath1,157 sq ft

1778 Beacon St #302, Brookline, MA 02445

Grand staircase • Ultra-high ceilings • Exposed brick wall

ABOUT THIS HOME
Vintage Home for sale in Chestnut Hill, MA:
Beautifully renovated 1 bedroom in Brownstone. Fantastic Brookline location! Great layout with no wasted space! This condo has many nice features including a Stylish kitchen with quartz countertops and stainless steel appliances. The bathroom has lovely tile and a custom glass shower as well as a heated floor. Additional amenities include great closet space, a fireplace, and air conditioning. There are high ceilings, large windows, & hardwood floors throughout. Professionally managed association. Convenient location! Easy access to the 3 trainlines on the Greenline T and the MBTA buses. Neighborhood has lots of lively perks including restaurants, supermarkets, shops and the Cleveland

$489,000

1 bed1 bath474 sq ft

1880 Beacon St #6, Brookline, MA 02445

Quartz countertops • Custom glass shower • Heated floor

ABOUT THIS HOME
Vintage Home for sale in Chestnut Hill, MA:
Perched on an elevated corner lot in Brighton, this beautifully maintained home combines classic craftsmanship w/ modern comfort. Inside, you’ll find gleaming hardwood floors, rich woodwork, & sun-filled rooms that radiate warmth & character. The main level features a ornamental fireplaced living room & dining room w/ a built-in hutch, ideal for both everyday living & entertaining. The spacious kitchen offers a walk-through pantry & generous storage. Upstairs includes four beds, & a full bath, providing comfort & flexibility for today’s lifestyle. The lower level adds laundry, ample storage & even a hot tub, creating a relaxing retre

$879,000

4 beds1 bath1,324 sq ft

21 Glenmont Rd, Brighton, MA 02135

Elevated corner lot • Hot tub • Walk-through pantry

Property at 255 Tappan St, Brookline, MA 02445, 7 beds, 5 baths

$2,999,999

7 beds5 baths4,171 sq ft

255 Tappan St, Brookline, MA 02445

Property at 1763 Beacon St Unit A, Brookline, MA 02445, 1 bed, 1 bath

$499,900

1 bed1 bath585 sq ft

1763 Beacon St Unit A, Brookline, MA 02445

Property at 3 Englewood Ave #9, Brookline, MA 02445, 1 bed, 1 bath

$559,000

1 bed1 bath680 sq ft

3 Englewood Ave #9, Brookline, MA 02445

Property at 159-161 Allston, Allston, MA 02134, 25 beds, 8 baths

$5,800,000

25 beds8 baths6,690 sq ft

159-161 Allston, Allston, MA 02134

Property at 19 Westbourne #2, Brookline, MA 02446, 1 bed, 1 bath

$489,000

1 bed1 bath670 sq ft

19 Westbourne #2, Brookline, MA 02446

Property at 155 Kilsyth Rd, Brighton, MA 02135, 8 beds, 6 baths

$2,500,000

8 beds6 baths5,093 sq ft

155 Kilsyth Rd, Brighton, MA 02135

Property at 266 Langley Rd #1, Newton, MA 02459, 3 beds, 2.5 baths

$1,550,000

3 beds2.5 baths2,035 sq ft

266 Langley Rd #1, Newton, MA 02459

Property at 97 Strathmore Rd #4, Brighton, MA 02135, 1 bed, 1 bath

$499,000

1 bed1 bath719 sq ft

97 Strathmore Rd #4, Brighton, MA 02135

Property at 39 Union St, Brighton, MA 02135, 9 beds, 3 baths

$2,099,000

9 beds3 baths3,615 sq ft

39 Union St, Brighton, MA 02135

Property at 40 Orkney Rd #1, Brighton, MA 02135, 2 beds, 1 bath

$545,000

2 beds1 bath800 sq ft

40 Orkney Rd #1, Brighton, MA 02135

Property at 33 Shannon St #3, Brighton, MA 02135, 3 beds, 2.5 baths

$749,999

3 beds2.5 baths1,371 sq ft

33 Shannon St #3, Brighton, MA 02135

Property at 39 South St Unit B, Brighton, MA 02135, 2 beds, 1 bath

$569,000

2 beds1 bath1,040 sq ft

39 South St Unit B, Brighton, MA 02135

Property at 1789 Commonwealth, Brighton, MA 02135, 14 beds, 6 baths

$3,700,000

14 beds6 baths6,206 sq ft

1789 Commonwealth, Brighton, MA 02135

Property at 100 Lanark Rd Unit A, Brighton, MA 02135, 2 beds, 1 bath

$399,000

2 beds1 bath730 sq ft

100 Lanark Rd Unit A, Brighton, MA 02135

Vintage Homes for Sale in Chestnut Hill

There are currently 10 vintage homes for sale in Chestnut Hill at a median listing price of $1.39M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chestnut Hill stay on the market for 83 days and receive 1 offers. Popular neighborhoods include Jamaica Plain, Roslindale, Brighton, Allston, and West Roxbury. This map is refreshed with the newest listings in Chestnut Hill every 15 minutes.

In the past month, 4 homes have been sold in Chestnut Hill. In addition to houses in Chestnut Hill, there were also 13 condos, 1 townhouse, and 1 multi-family unit for sale in Chestnut Hill last month. Chestnut Hill is a moderately walkable neighborhood in Middlesex County with a Walk Score of 52. Chestnut Hill is home to approximately 9,146 people. Find your dream home in Chestnut Hill using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chestnut Hill are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chestnut Hill. If you're looking to sell your home in the Chestnut Hill area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chestnut Hill with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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