HeaderIcon
  1. Agent Logo

Explore by Metro

  • Atlanta
  • Baltimore
  • Boston
  • Bronx
  • Brooklyn
  • Chicago
  • Los Angeles
  • Manhattan
  • Miami
  • Nashville
  • Orlando
  • Philadelphia
  • Phoenix
  • Queens
  • San Diego
  • San Jose
  • Tampa
  • Washington
HeaderIcon

Explore by Metro

  • Atlanta
  • Baltimore
  • Boston
  • Bronx
  • Brooklyn
  • Chicago
  • Los Angeles
  • Manhattan
  • Miami
  • Nashville
  • Orlando
  • Philadelphia
  • Phoenix
  • Queens
  • San Diego
  • San Jose
  • Tampa
  • Washington
leftArrowBack to Search
  1. Home
  2. /
  3. Boston, MA
  4. /
  5. 249 Chestnut Hill Ave
Add to favoritesAdd to favorites (hover)
Save
leftArrow
Add to favoritesAdd to favorites (hover)

249 Chestnut Hill Ave

249 Chestnut Hill Ave, Boston, MA, 02135

YEAR BUILT

1920

# STORIES

1

# TOTAL UNITS

29

UNIT SIZE RANGE

322-763 sqft

Description

249 Chestnut Hill Ave sits in Boston and is a low-rise building with just 1 story. This condo building has a total of 29 units, featuring a size range from 322 to 763 square feet. Constructed in 1920, the building reflects a classic style that fits well in the neighborhood. Unit prices range from $200,000 to $137,000, with the lowest sold price in the last 12 months around $475,000. The average closed price for recent sales is also $475,000, translating to about $623 per square foot. Homes in this building typically spend around 31 days on the market. The building offers several amenities like laundry facilities, hot water, and an elevator. Residents can enjoy a pool as well. Public transportation options are nearby, connecting easily to the B, C, and D Green Train Lines. This makes it straightforward to travel around Boston. Local restaurants, such as Fins Sushi & Grille, are within reach for dining out. Grocery needs can be met at places like Aden Convenience and Deli Inc and 7-Eleven. Scenic paths around the Chestnut Hill Reservoir are nearby, providing nice areas for walking or jogging. The layout of the units is thoughtfully designed, with options for 1 and 2 bedrooms. Some units might have hardwood floors, adding charm to the living space. This property combines basic urban living with access to local parks and transportation, making it a comfortable option for various lifestyles.

Building ImageMLS ID #73338147
Building ImageMLS ID #73338147
Building Image
Building ImageView Listing

249 Chestnut Hill Ave

249 Chestnut Hill Ave, Boston, MA, 02135

YEAR BUILT

1920

# STORIES

1

# TOTAL UNITS

29

UNIT SIZE RANGE

322-763 sqft

Description

249 Chestnut Hill Ave sits in Boston and is a low-rise building with just 1 story. This condo building has a total of 29 units, featuring a size range from 322 to 763 square feet. Constructed in 1920, the building reflects a classic style that fits well in the neighborhood. Unit prices range from $200,000 to $137,000, with the lowest sold price in the last 12 months around $475,000. The average closed price for recent sales is also $475,000, translating to about $623 per square foot. Homes in this building typically spend around 31 days on the market. The building offers several amenities like laundry facilities, hot water, and an elevator. Residents can enjoy a pool as well. Public transportation options are nearby, connecting easily to the B, C, and D Green Train Lines. This makes it straightforward to travel around Boston. Local restaurants, such as Fins Sushi & Grille, are within reach for dining out. Grocery needs can be met at places like Aden Convenience and Deli Inc and 7-Eleven. Scenic paths around the Chestnut Hill Reservoir are nearby, providing nice areas for walking or jogging. The layout of the units is thoughtfully designed, with options for 1 and 2 bedrooms. Some units might have hardwood floors, adding charm to the living space. This property combines basic urban living with access to local parks and transportation, making it a comfortable option for various lifestyles.

Next

Description

249 Chestnut Hill Ave sits in Boston and is a low-rise building with just 1 story. This condo building has a total of 29 units, featuring a size range from 322 to 763 square feet. Constructed in 1920, the building reflects a classic style that fits well in the neighborhood. Unit prices range from $200,000 to $137,000, with the lowest sold price in the last 12 months around $475,000. The average closed price for recent sales is also $475,000, translating to about $623 per square foot. Homes in this building typically spend around 31 days on the market. The building offers several amenities like laundry facilities, hot water, and an elevator. Residents can enjoy a pool as well. Public transportation options are nearby, connecting easily to the B, C, and D Green Train Lines. This makes it straightforward to travel around Boston. Local restaurants, such as Fins Sushi & Grille, are within reach for dining out. Grocery needs can be met at places like Aden Convenience and Deli Inc and 7-Eleven. Scenic paths around the Chestnut Hill Reservoir are nearby, providing nice areas for walking or jogging. The layout of the units is thoughtfully designed, with options for 1 and 2 bedrooms. Some units might have hardwood floors, adding charm to the living space. This property combines basic urban living with access to local parks and transportation, making it a comfortable option for various lifestyles.

249 Chestnut Hill Ave Market Stats Last 12 months

Avg. Listed Price$449,900($590/Sqft.)
Avg. Sale Price$475,000($623/Sqft.)
Year over year list priceUp Arrow46.31%
Year over year sale priceUp Arrow 47.29%
Total Listings1 Listed
Total sold1 Sold
Average Days on Market31 days
Average HOA fees per sqft$2 /monthly
Next

Market Stats

Year over year list priceUp Arrow46.31%
Year over year sale priceUp Arrow47.29%
Total Listings1 Listed
Total sold1 Sold
Average Days on Market31 days
Average HOA fees per sqft$2 /monthly

Glen Gardens Estate Availability & Demand

Unit Availability

-
High availability buildings list units frequently.

Unit Availability helps to understand how often units in a particular building are listed for sale as compared with the neighborhood average. Units are rarely listed in buildings with low availability.

Unit Demand

-
Units in high-demand buildings sell quicker.

Unit Demand is a measure of quickly units in a particular building sell as compared with other buildings in the neighborhood. Units in high-demand buildings sell more quickly.

For Sale 0 For Sale

249 Chestnut Hill Ave Inventory & Sale History

UnitSize (sqft)BedsBathsDays On MarketDateStatusPrice
Unit 212176321312025-03-28
MLS#: 73338147 		Closed$475,000
Unit 414176321282020-10-01
MLS#: 72719865 		Closed$409,500
Unit 242456011502020-02-29
MLS#: 72606614 		Closed$377,000
Unit 21
21

2 Beds

1 Baths

763 sqft

DateStatusPrice
2025-03-28Closed$475,000
MLS#: 73338147
Days On Market31
Unit 24
24

1 Beds

1 Baths

560 sqft

DateStatusPrice
2020-02-29Closed$377,000
MLS#: 72606614
Days On Market50
Unit 41
41

2 Beds

1 Baths

763 sqft

DateStatusPrice
2020-10-01Closed$409,500
MLS#: 72719865
Days On Market28
View Complete Unit Listing HistorySource By: MLSPIN

Amenities

Living in Chestnut Hill Arms means enjoying a suite of amenities that enhances your urban lifestyle. Elevators make it easy to access various floors, and laundry facilities mean you won't have to trek far to handle your chores. Hot water is provided, which is always a plus in chilly Boston. For those fond of outdoor activities, you can unwind at the nearby park or take a refreshing dip in the pool. Additionally, public transportation is easily accessible, making commuting a breeze.

Next

Amenities Description

Living in Chestnut Hill Arms means enjoying a suite of amenities that enhances your urban lifestyle. Elevators make it easy to access various floors, and laundry facilities mean you won't have to trek far to handle your chores. Hot water is provided, which is always a plus in chilly Boston. For those fond of outdoor activities, you can unwind at the nearby park or take a refreshing dip in the pool. Additionally, public transportation is easily accessible, making commuting a breeze.

Parking
Parking
Locker
Locker
Concierge
Concierge
Elevator(s)
Elevator(s)
Check Icon
Central AC
Central AC
Pool
Pool
Check Icon
Fitness Center
Fitness Center
-
Visitors Parking
Visitors Parking
Next

Amenities

Elevator(s)

Elevator(s)

Laundry

Laundry

Balcony

Balcony

Pool

Pool

Policies

Before making a purchase, it’s handy to be aware of building policies. Chestnut Hill Arms does have restrictions in place, which is common in condo living. These ensure that the community stays harmonious and well-maintained, giving you peace of mind as you settle into this beautiful enclave.

Pet Allowed
Pet Allowed
BBQ Permitted
BBQ Permitted
Sublet Allowed
Sublet Allowed
Short-term Rental Allowed
Short-term Rental Allowed

Compare with Buildings in the Neighbourhood (Last 12 Months)

Compare building's average price/sq. ft. and HOA fees/sq. ft. to buildings nearby

Building NameAvg price per square footAVG HOA FEE per square foot (Monthly)
249 Chestnut Hill Ave$623/sqft.$2 /sqft.
Chestnut Hill Arms$821/sqft.$2 /sqft.
Chestnut Hill Condo Trust$719/sqft.$2 /sqft.
247 Chestnut Hill Ave$719/sqft.$2 /sqft.
137 Englewood Ave$707/sqft.$2 /sqft.
145 Englewood$793/sqft.$2 /sqft.

Nearby Schools

In Brighton, 249 Chestnut Hill Ave benefits from nearby schools within easy reach. Educational institutions within 2 miles reduce travel time for families. This convenient access supports balanced daily routines. The location promotes comfortable urban living.

Yeshiva Ohr Yisrael High School for Boys

--
Private|Grades 9–12
325 Reservoir Rd|0.4 miles away

Yeshiva Ohr Yisroel

--
Private|Grades 9–12
74 Corey Rd|0.67 miles away

Thomas Edison K-8 School

C-
Public|Grades PK–8
60 Glenmont Rd|0.68 miles away

John D. Runkle School

A-
Public|Grades PK–8
50 Druce St|0.68 miles away

Heath School

A
Public|Grades PK–8
100 Eliot St|0.68 miles away

Winship Elementary School

C+
Public|Grades PK–5
54 Dighton St|0.75 miles away
Next

Schools

arrow rightWhat to know about schoolsarrow right
Next

Description

In Brighton, 249 Chestnut Hill Ave benefits from nearby schools within easy reach. Educational institutions within 2 miles reduce travel time for families. This convenient access supports balanced daily routines. The location promotes comfortable urban living.

Yeshiva Ohr Yisrael High School for Boys

--
Private|Grades 9–12
325 Reservoir Rd|Less than 1 Mile Away

Yeshiva Ohr Yisroel

--
Private|Grades 9–12
74 Corey Rd|Less than 1 Mile Away

Thomas Edison K-8 School

C-
Public|Grades PK–8
60 Glenmont Rd|Less than 1 Mile Away

John D. Runkle School

A-
Public|Grades PK–8
50 Druce St|Less than 1 Mile Away

Heath School

A
Public|Grades PK–8
100 Eliot St|Less than 1 Mile Away

Winship Elementary School

C+
Public|Grades PK–5
54 Dighton St|Less than 1 Mile Away

The Chestnut Hillschool

--
Private|Grades PK–6
428 Hammond St|Less than 1 Mile Away

Brimmer & May School

--
Private|Grades PK–12
69 Middlesex Rd|Less than 1 Mile Away

Baldwin Early Learning Center

--
Public|Grades EE–1
121 Corey Rd|Less than 1 Mile Away

Torah Academy

--
Private|Grades PK–8
11 Williston Rd|Less than 1 Mile Away

Brighton High School

F
Public|Grades 9–12
25 Warren St|Less than 1 Mile Away

Mount Alvernia Academy

--
Private|Grades PK–6
20 Manet Rd|Less than 1 Mile Away

Michael Driscoll School

A
Public|Grades PK–8
64 Westbourne Ter|Less than 1 Mile Away

Mesivta High School of Greater Boston

--
Private|Grades 9–12
34 Sparhawk St|1.02 Miles Away

Boston Green Academy

D+
Public|Grades 6–12
20 Warren St|1.04 Miles Away

Mary Lyon K-8 School

--
Public|Grades KG–8
50 Beechcroft St|1.05 Miles Away

Kennedy Day School

--
Private|Grades PK–12
30 Warren St|1.11 Miles Away

Lyon Upper 9-12 School

D-
Public|Grades 9–12
95 Beechcroft St|1.11 Miles Away

St Columbkille Partnership School

--
Private|Grades PK–8
25 Arlington St|1.12 Miles Away

St Joseph Preparatory High School

--
Private|Grades 9–12
617 Cambridge St|1.21 Miles Away

John Ward

B
Public|Grades KG–5
10 Dolphin Rd|1.28 Miles Away

Maimonides

--
Private|Grades PK–12
34 Philbrick Rd|1.31 Miles Away

Maimonides School Elementary Section

--
Private|Grades KG–5
34 Philbrick Rd|1.32 Miles Away

Brookline High School

B+
Public|Grades 9–12
115 Greenough St|1.34 Miles Away

Brookline Early Education Program at Clark Road

--
Public|Grades PK–PK
333 Washington St ...|1.40 Miles Away

Beaver Country Day School

--
Private|Grades 6–12
791 Hammond St|1.39 Miles Away

William H. Lincoln School

A-
Public|Grades KG–8
19 Kennard Rd|1.40 Miles Away

Horace Mann School For The Deaf

--
Public|Grades PK–12
40 Armington St|1.41 Miles Away

Jackson Mann K-8 School

D+
Public|Grades PK–8
40 Armington St|1.41 Miles Away

St Herman of Alaska Christian School

--
Private|Grades KG–8
62 Harvard Ave|1.67 Miles Away

Edward Devotion School

B
Public|Grades KG–8
345 Harvard St|1.69 Miles Away

Bay Cove Academy

--
Private|Grades 8–12
156 Lawton St|1.69 Miles Away

Pierce School

A
Public|Grades KG–8
50 School St|1.74 Miles Away

The Park School

--
Private|Grades PK–8
171 Goddard Ave|1.74 Miles Away

Bigelow Middle School

B
Public|Grades 6–8
42 Vernon St|1.80 Miles Away

German International School Boston

--
Private|Grades PK–12
57 Holton St|1.89 Miles Away

Mt Alvernia High School

--
Private|Grades 7–12
790 Centre St|1.90 Miles Away

Underwood

A-
Public|Grades KG–5
101 Vernon St|1.96 Miles Away

Gardner Pilot Academy

D+
Public|Grades PK–8
30 Athol St|1.96 Miles Away

Bowen

A+
Public|Grades KG–5
280 Cypress St|1.99 Miles Away

Transit

249 Chestnut Hill Ave is located in a well-connected part of Brighton, Boston, supported by nearby public transportation. Transit options within a 2-mile radius improve accessibility for daily commuting. Residents enjoy convenient travel across surrounding neighborhoods and downtown areas. This connectivity enhances overall quality of urban living.

1079 Commonwealth Ave

1.92 miles away|37 min walk

239 N Beacon St

1.39 miles away|27 min walk

280 Boylston St

1.75 miles away|34 min walk

325 Boylston St

1.82 miles away|35 min walk

367 Western Ave opp Brighton Mills Mall

1.98 miles away|38 min walk

445 Western Ave

1.9 miles away|37 min walk
Next

Transit

arrow rightWhat to know about transitarrow right
Next

Description

249 Chestnut Hill Ave is located in a well-connected part of Brighton, Boston, supported by nearby public transportation. Transit options within a 2-mile radius improve accessibility for daily commuting. Residents enjoy convenient travel across surrounding neighborhoods and downtown areas. This connectivity enhances overall quality of urban living.

1079 Commonwealth Ave

1.92 miles away|37 min walk

239 N Beacon St

1.39 miles away|27 min walk

280 Boylston St

1.75 miles away|34 min walk

325 Boylston St

1.82 miles away|35 min walk

367 Western Ave opp Brighton Mills Mall

1.98 miles away|38 min walk

445 Western Ave

1.9 miles away|37 min walk

450 Western Ave

1.88 miles away|36 min walk

495 Western Ave

1.82 miles away|35 min walk

684 Washington St

1.05 miles away|21 min walk

785 Centre St

1.91 miles away|37 min walk

790 Centre St

1.9 miles away|37 min walk

7 Winship St

0.86 miles away|17 min walk

850 Boylston St

0.77 miles away|15 min walk

Allston Street

1.19 miles away|23 min walk

Arsenal St @ Arlington St

1.79 miles away|35 min walk

Arsenal St @ Bond St

1.83 miles away|36 min walk

Arsenal St @ Forge Rd

1.77 miles away|34 min walk

Arsenal St opp School St

1.96 miles away|38 min walk

Arsenal St opp Talcott Ave

1.91 miles away|37 min walk

Arsenal St @ School St

1.99 miles away|39 min walk

Arsenal St @ Talcott Ave

1.89 miles away|37 min walk

Arsenal St @ Watertown Mall

1.84 miles away|36 min walk

Beaconsfield

0.68 miles away|14 min walk

Beaconsfield - Beaconsfield Rd

0.75 miles away|15 min walk

Beaconsfield - Clark Rd

0.75 miles away|15 min walk

Beaconsfield - Dean Rd Beacon St

0.68 miles away|13 min walk

Beaconsfield - Parking Lot

0.73 miles away|14 min walk

Birmingham Pkwy @ Soldiers Field Rd

1.53 miles away|30 min walk

Boston College

0.67 miles away|13 min walk

Boston College - Commonwealth Ave @ Lake St

0.64 miles away|13 min walk

Boston Landing

1.58 miles away|31 min walk

Boston Landing - Guest St @ Arthur St

1.51 miles away|29 min walk

Boylston St @ Chestnut Hill Ave

0.9 miles away|18 min walk

Boylston St @ Clark Rd

1.42 miles away|28 min walk

Boylston St @ Hammond St

1.02 miles away|20 min walk

Boylston St @ Heath St

0.94 miles away|19 min walk

Boylston St @ Kennard Rd

1.43 miles away|28 min walk

Boylston St @ Norfolk Rd

0.86 miles away|17 min walk

Boylston St @ Randolph Rd

0.86 miles away|17 min walk

Boylston St @ Reservoir Rd

0.76 miles away|15 min walk

Boylston St @ Star Market - Service Rd

1.12 miles away|22 min walk

Boylston St @ Sumner Rd

1.24 miles away|24 min walk

Boylston St @ Tully St

1.2 miles away|23 min walk

Boylston St @ Warren St

1.23 miles away|24 min walk

Boylston St @ White Ave

0.84 miles away|17 min walk

Brandon Hall

1.33 miles away|26 min walk

Brighton Ave @ Allston St

1.54 miles away|30 min walk

Brighton Ave @ Cambridge St

1.47 miles away|29 min walk

Brighton Ave @ Commonwealth Ave

1.8 miles away|35 min walk

Brighton Ave @ Harvard Ave

1.61 miles away|31 min walk

The Neighbourhood: Brighton

Brighton is a lively Boston neighborhood with a mix of shops, parks, and dining. The area offers riverside paths, parks, and places for walking and biking. It includes grocery stores, cafes, specialty shops, and varied restaurants. The district hosts community markets, seasonal fairs, and local events. Schools, clinics, libraries, and basic services sit close to homes and shops. The area links to downtown by MBTA Green Line, bus routes, and bike lanes. It provides easy road access and public transportation for daily trips.

Next

Neighbourhood Description

Brighton is a lively Boston neighborhood with a mix of shops, parks, and dining. The area offers riverside paths, parks, and places for walking and biking. It includes grocery stores, cafes, specialty shops, and varied restaurants. The district hosts community markets, seasonal fairs, and local events. Schools, clinics, libraries, and basic services sit close to homes and shops. The area links to downtown by MBTA Green Line, bus routes, and bike lanes. It provides easy road access and public transportation for daily trips.

Similar Buildings Nearby

Add to favoritesAdd to favorites (hover)
Chestnut Hill Arms
249 Chestnut Hill Avenue, Boston, MA
Click to see listings
Add to favoritesAdd to favorites (hover)
19 Colliston Rd
19 Colliston Rd, Boston, MA
Click to see listings
Add to favoritesAdd to favorites (hover)
88 Gordon St
88 Gordon St., Boston, MA
Click to see listings
Add to favoritesAdd to favorites (hover)
88 Gordon St
88 Gordon St, Boston, MA
Click to see listings
Add to favoritesAdd to favorites (hover)
Chestnut Hill Arms
249 Chestnut Hill Avenue, Boston, MA
Click to see listings
Add to favoritesAdd to favorites (hover)
19 Colliston Rd
19 Colliston Rd, Boston, MA
Click to see listings
Add to favoritesAdd to favorites (hover)
88 Gordon St
88 Gordon St., Boston, MA
Click to see listings
View All Similar Buildings

249 Chestnut Hill Ave Demographics

Age Demographics

0–14 Years

5.69%

15–29 Years

47.03%

30–44 Years

20.48%

45–59 Years

10.01%

60+ Years

16.79%

Commute

38.35%

Transit

7.3%

Walk

34.95%

Drive

3.03%

Bike

Housing Ownership

22.27%

Owner Occupied

77.73%

Rental Units

Household Types

Single Family
17.17%
Multi Family
3.04%
Single Person
39.18%
Multi Person
60.82%

Average Income

Household:$9,620,507.63 /yr

Individual:$5,731,611.01 /yr

Education

Bachelors Degree39.68%
High School College7.79%
Diploma2.51%
Post Graduate37.69%
Others12.33%
Next

Education

Diploma2.51%
Post Graduate37.69%
Others12.33%
Get the HelloCondo Newsletter
Real-estate tips, insights, and market reports in your inbox.
Newsletter
  1. Home
  2. /Brighton, MA
  3. /
    249 Chestnut Hill Ave
Nearby Cities
Avon
Buildings
126 Englewood
137 Englewood Ave
145 Englewood
1868 Commonwealth
1870 Commonwealth Ave
1872 Commonwealth Ave
1874 Commonwealth Ave
1880 Commonwealth
1880 Commonwealth Ave
247 Chestnut Hill Ave
249 Chestnut Hill Ave
Chestnut Hill Arms
Chestnut Hill Condo Trust
Chestnut Hill Condominiums
Chestnut Hill Park Condominium...
CHESTNUT MANOR
Englewood Heights
Turn Of The Century Condo
Neighborhoods
AnglesideBabson ParkBank Square
Boston Common / Park SquareBridge Street NeckBrightonCedarwoodCliff EstatesCoburnvilleCottage ParkCummingsvilleDana HallDuck VillageLinden HighlandsLynn EnglishMishawumMission HillOak GrovePorter SquareSuffolk Square
ZIP Codes
014320146301821
0183001832018330183501854018620186301879018890192901945020210219902339023500246002762
Community
10 Beaufort Road Condominiums10-14 Park Vale Avenue Apartments10-14 Sydney Street Condominiums
10-32A Glenville Avenue Apartments100 Boatswains Way100 Captains Row100 Commandants Way100 High Street Condominiums100 Main Street100 Pond Street100 Riverway101 Prince Street101-107 Winthrop Road103 Alban Street105 Beacon Street105 West 3rd Street107 Chestnut Street108 Mount Vernon Street108 Washington Street109 Beach Street
HelloCondo Logo
HelloCondo Logo
HelloCondo Is The #1 Condo Search Platform And Real Estate Recommendation Engine. Search, Find And Buy The Perfect Condo And Get Matched With The Best Agents. Finding A Condo Has Never Been So Easy.

HelloCondo is a division of HelloCasa, LLC

FacebookIconInstagramIconXIconRedditIcon

HelloCondo

Find A RealtorTerms of UsePrivacy PolicyCalifornia Privacy NoticeAccessibility PolicyCCPA Notice on CollectionDMCABrowseNYS Standard Operating ProcedureNYS Fair Housing Notice

Contact

LocationIcon
300 Galleria Pkwy SE, Suite 1500,
Atlanta, GA 30339
PhoneICon
(855) 625-0319
EmailIConhello@hellocondo.com
Contact Us

For Sale

Condos for saleTownhomes for sale
AgentIcon
LocationIcon

The Market

Lindsay Higgins

PO Box 290148 Boston, MA 02129

PhoneICon781-789-2740
EmailIConLindsay@TheMarket.Properties
© HelloCondo 2026. All Rights Reserved.