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. 288 Chestnut Ave
Add to favoritesAdd to favorites (hover)
Save
leftArrow
Add to favoritesAdd to favorites (hover)

288 Chestnut Ave

288 Chestnut Avenue, Boston, MA, 02130

YEAR BUILT

1890

# STORIES

3

# TOTAL UNITS

6

UNIT SIZE RANGE

832-1,096 sqft

Description

288 Chestnut Ave is a distinctive, three-story condo building initially constructed in 1890. This property offers both 1 and 2-bedroom configurations, combining historic architecture with essential urban amenities. The building features a unique blend of classic design and modern living spaces, creating an inviting atmosphere for residents. The building’s amenities cater to a variety of lifestyles. Residents can enjoy the on-site tennis courts, perfect for tennis enthusiasts seeking regular practice opportunities. For those who favor golf, convenient access ensures leisurely outings. Fitness enthusiasts can take advantage of the nearby bike path, promoting active lifestyles, while the pool and garden area provide relaxation and enjoyment. Strategically located, the building benefits from easy access to public transportation, facilitating convenient commutes and city exploration. Highway access further enhances connectivity for drivers. The surrounding environment includes a house of worship and a conservation area, providing a tranquil atmosphere amidst the urban setting. Nearby parks offer green spaces for outdoor activities, while the vibrant local scene supports a dynamic lifestyle. 288 Chestnut Ave is ideally suited for individuals seeking a blend of historical charm and modern amenities within an accessible, urban context.

Building ImageMLS ID #72203184
Building ImageMLS ID #72203184
Building Image
Building ImageView Listing

288 Chestnut Ave

288 Chestnut Avenue, Boston, MA, 02130

YEAR BUILT

1890

# STORIES

3

# TOTAL UNITS

6

UNIT SIZE RANGE

832-1,096 sqft

Description

288 Chestnut Ave is a distinctive, three-story condo building initially constructed in 1890. This property offers both 1 and 2-bedroom configurations, combining historic architecture with essential urban amenities. The building features a unique blend of classic design and modern living spaces, creating an inviting atmosphere for residents. The building’s amenities cater to a variety of lifestyles. Residents can enjoy the on-site tennis courts, perfect for tennis enthusiasts seeking regular practice opportunities. For those who favor golf, convenient access ensures leisurely outings. Fitness enthusiasts can take advantage of the nearby bike path, promoting active lifestyles, while the pool and garden area provide relaxation and enjoyment. Strategically located, the building benefits from easy access to public transportation, facilitating convenient commutes and city exploration. Highway access further enhances connectivity for drivers. The surrounding environment includes a house of worship and a conservation area, providing a tranquil atmosphere amidst the urban setting. Nearby parks offer green spaces for outdoor activities, while the vibrant local scene supports a dynamic lifestyle. 288 Chestnut Ave is ideally suited for individuals seeking a blend of historical charm and modern amenities within an accessible, urban context.

Next

Description

288 Chestnut Ave is a distinctive, three-story condo building initially constructed in 1890. This property offers both 1 and 2-bedroom configurations, combining historic architecture with essential urban amenities. The building features a unique blend of classic design and modern living spaces, creating an inviting atmosphere for residents. The building’s amenities cater to a variety of lifestyles. Residents can enjoy the on-site tennis courts, perfect for tennis enthusiasts seeking regular practice opportunities. For those who favor golf, convenient access ensures leisurely outings. Fitness enthusiasts can take advantage of the nearby bike path, promoting active lifestyles, while the pool and garden area provide relaxation and enjoyment. Strategically located, the building benefits from easy access to public transportation, facilitating convenient commutes and city exploration. Highway access further enhances connectivity for drivers. The surrounding environment includes a house of worship and a conservation area, providing a tranquil atmosphere amidst the urban setting. Nearby parks offer green spaces for outdoor activities, while the vibrant local scene supports a dynamic lifestyle. 288 Chestnut Ave is ideally suited for individuals seeking a blend of historical charm and modern amenities within an accessible, urban context.

288 Chestnut Ave Market Stats Last 12 months

Avg. Listed Price-
Avg. Sale Price-
Year over year list price0.00%
Year over year sale price 0.00%
Total Listings0 Listed
Total sold0 Sold
Average Days on Market0 days
Average HOA fees per sqft-
Next

Market Stats

Year over year list price0.00%
Year over year sale price0.00%
Total Listings0 Listed
Total sold0 Sold
Average Days on Market0 days
Average HOA fees per sqft-

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

288 Chestnut Ave Inventory & Sale History

UnitSize (sqft)BedsBathsDays On MarketDateStatusPrice
Unit 22109622702017-10-03
MLS#: 72203184 		Closed$735,000
Unit 3383211682017-07-17
MLS#: 72161844 		Closed$445,000
Unit 22109622492016-06-15
MLS#: 71995307 		Closed$672,000
Unit 2
2

2 Beds

2 Baths

1096 sqft

DateStatusPrice
2017-10-03Closed$735,000
MLS#: 72203184
Days On Market70
Unit 2
2

2 Beds

2 Baths

1096 sqft

DateStatusPrice
2016-06-15Closed$672,000
MLS#: 71995307
Days On Market49
Unit 3
3

1 Beds

1 Baths

832 sqft

DateStatusPrice
2017-07-17Closed$445,000
MLS#: 72161844
Days On Market68
View Complete Unit Listing HistorySource By: MLSPIN

Amenities

One of the significant perks of living at 288 Chestnut Ave is the array of amenities right at your fingertips. Imagine spending warm summer evenings at the on-site tennis court or enjoying the pool on hot days. For those who love staying active, the nearby bike path offers great options for outdoor exercise, while the garden area and parks provide serene spots to unwind. Excellent highway access and public transportation options make commuting a breeze, whether you’re headed to work or exploring all that Boston has to offer. Plus, with a house of worship nearby, you can find both community and convenience in your daily life.

Next

Amenities Description

One of the significant perks of living at 288 Chestnut Ave is the array of amenities right at your fingertips. Imagine spending warm summer evenings at the on-site tennis court or enjoying the pool on hot days. For those who love staying active, the nearby bike path offers great options for outdoor exercise, while the garden area and parks provide serene spots to unwind. Excellent highway access and public transportation options make commuting a breeze, whether you’re headed to work or exploring all that Boston has to offer. Plus, with a house of worship nearby, you can find both community and convenience in your daily life.

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

Amenities

Tennis Court(s)

Tennis Court(s)

Storage

Storage

Pool

Pool

Policies

Every building has its policies, and 288 Chestnut Ave is no different. This property has certain restrictions that help maintain its charm and serenity, ensuring a comfortable living environment for all residents. It's always good to know these before settling in, and our friendly community ensures that everyone respects these guidelines.

Next

Amenities Description

Every building has its policies, and 288 Chestnut Ave is no different. This property has certain restrictions that help maintain its charm and serenity, ensuring a comfortable living environment for all residents. It's always good to know these before settling in, and our friendly community ensures that everyone respects these guidelines.

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)
288 Chestnut Ave--
42 Rockview St$823/sqft.$4 /sqft.
111-121 Green St$778/sqft.$2 /sqft.
38 Rockview St$662/sqft.$6 /sqft.
13 Oakdale$781/sqft.$4 /sqft.
12 Clive St$813/sqft.$4 /sqft.

Nearby Schools

Discover top-rated schools located close to 288 Chestnut Ave.

Hollow Reed School

--
Private|Grades PK–KG
93 Sedgwick St|0.44 miles away

Meridian Academy

--
Private|Grades 6–12
54 Brookside Ave|0.46 miles away

Community Academy

--
Public|Grades 9–12
25 Glen Rd|0.57 miles away

Curley K-8 School

D+
Public|Grades PK–8
493 Centre St|0.58 miles away

Mission Hill K-8 School

D
Public|Grades PK–8
20 Child St|0.58 miles away

Margarita Muniz Academy

D-
Public|Grades 9–12
20 Child St|0.6 miles away
Next

Schools

Hollow Reed School

--
Private|Grades PK–KG
93 Sedgwick St|Less than 1 Mile Away

Meridian Academy

--
Private|Grades 6–12
54 Brookside Ave|Less than 1 Mile Away

Community Academy

--
Public|Grades 9–12
25 Glen Rd|Less than 1 Mile Away

Curley K-8 School

D+
Public|Grades PK–8
493 Centre St|Less than 1 Mile Away

Mission Hill K-8 School

D
Public|Grades PK–8
20 Child St|Less than 1 Mile Away

Margarita Muniz Academy

D-
Public|Grades 9–12
20 Child St|Less than 1 Mile Away

The English High School

F
Public|Grades 9–12
144 McBride St|Less than 1 Mile Away

Ellis Mendell Elementary School

C-
Public|Grades PK–5
164 School St|Less than 1 Mile Away

Greater Egleston Community High School

--
Public|Grades 9–12
3134 Washington St...|Less than 1 Mile Away

Rafael Hernandez K-8 School

D+
Public|Grades PK–8
61 School St|Less than 1 Mile Away

John F. Kennedy Elementary School

C+
Public|Grades PK–5
7 Bolster St|Less than 1 Mile Away

Nativity Preparatory School

--
Private|Grades 4–8
39 Lamartine St|Less than 1 Mile Away

David A. Ellis Elementary School

F
Public|Grades PK–5
302 Walnut Ave|1.21 Miles Away

James W Hennigan

C
Public|Grades KG–8
200 Heath St|1.25 Miles Away

West Zone Early Learning Center

--
Public|Grades EE–1
200 Heath St|1.25 Miles Away

Higginson K-2 School

--
Public|Grades PK–2
160 Harrishof St|1.32 Miles Away

Roxbury Preparatory Charter School

C+
Public|Grades 5–12
120 Fisher Ave|1.43 Miles Away

Italian Home for Children

--
Private|Grades 1–8
1125 Centre St|1.51 Miles Away

British International School of Boston

--
Private|Grades PK–12
416 Pond St|1.51 Miles Away

William Monroe Trotter K-8 School

C-
Public|Grades PK–8
135 Humboldt Ave|1.55 Miles Away

Joseph P. Manning Elementary School

B-
Public|Grades PK–5
130 Louders Ln|1.64 Miles Away

Boston Teachers Union K-8 School

C
Public|Grades PK–8
25 Walk Hill St|1.75 Miles Away

Higginson / Lewis K-8 School

F
Public|Grades PK–8
131 Walnut Ave|1.75 Miles Away

The Park School

--
Private|Grades PK–8
171 Goddard Ave|1.76 Miles Away

Nathan Hale Elementary School

B+
Public|Grades PK–5
51 Cedar St|1.76 Miles Away

Boston Latin Acadeny

A-
Public|Grades 7–12
205 Townsend St|1.79 Miles Away

Fenway High School

D+
Public|Grades 9–12
67 Alleghany St|1.83 Miles Away

City on a Hill Charter Public School Circuit Street

D-
Public|Grades 9–12
58 Circuit St|1.83 Miles Away

Mother Caroline Academy & Education Center

--
Private|Grades 4–8
515 Blue Hill Ave|1.86 Miles Away

Bridge Boston Charter School

C+
Public|Grades PK–8
435 Warren St|1.88 Miles Away

The Lynch Center

--
Public|Grades PK–PK
599 Brookline Ave|1.98 Miles Away

William H. Lincoln School

A-
Public|Grades KG–8
19 Kennard Rd|2.01 Miles Away

Jeremiah E. Burke High School

C-
Public|Grades 9–12
60 Washington St|2.03 Miles Away

Malik Academy

--
Private|Grades 1–8
100 Malcolm X Blvd|2.05 Miles Away

Maurice J. Tobin K-8 School

C-
Public|Grades PK–8
40 Smith St|2.05 Miles Away

Brookline Early Education Program at Clark Road

--
Public|Grades PK–PK
333 Washington St ...|2.08 Miles Away

James P. Timilty Middle School

D
Public|Grades 6–8
205 Roxbury St|2.11 Miles Away

Maimonides School Elementary Section

--
Private|Grades KG–5
34 Philbrick Rd|2.15 Miles Away

Haynes Early Education Center

--
Public|Grades EE–1
263 Blue Hill Ave|2.16 Miles Away

Maimonides

--
Private|Grades PK–12
34 Philbrick Rd|2.18 Miles Away

Pierce School

A
Public|Grades KG–8
50 School St|2.22 Miles Away

Madison Park High

F
Public|Grades 9–12
75 Malcolm X Blvd|2.23 Miles Away

Apple Orchard School

--
Private|Grades PK–KG
282D Newton St|2.24 Miles Away

John D. O'Bryant School of Mathematics and Science

A-
Public|Grades 7–12
55 Malcolm X Blvd|2.26 Miles Away

Brookline High School

B+
Public|Grades 9–12
115 Greenough St|2.29 Miles Away

Martin Luther Jr. King K-8 School

C-
Public|Grades PK–8
77 Lawrence Ave|2.32 Miles Away

Boston Day & Evening Academy

F
Public|Grades 9–12
20 Kearsarge Ave|2.35 Miles Away

Henry Dearborn STEM Academy

D-
Public|Grades 6–12
36 Winthrop St|2.38 Miles Away

Boston Latin School

A-
Public|Grades 7–12
78 Avenue Louis Pa...|2.41 Miles Away

Lilla G. Frederick Middle School

D-
Public|Grades 6–8
270 Columbia Rd|2.42 Miles Away

Transit

Experience convenience and connectivity with premium transit options just moments away.

775 Centre St

0.46 miles away|9 min walk

Arborway opp Courthouse

1.05 miles away|21 min walk

Arborway @ Courthouse

1.07 miles away|21 min walk

177 Heath St opp Walden St

1.31 miles away|26 min walk

34 Heath St opp Bromley St

1.36 miles away|27 min walk

107 Heath St opp Bickford Ave

1.38 miles away|27 min walk
Next

Transit

775 Centre St

0.46 miles away|9 min walk

Arborway opp Courthouse

1.05 miles away|21 min walk

Arborway @ Courthouse

1.07 miles away|21 min walk

177 Heath St opp Walden St

1.31 miles away|26 min walk

34 Heath St opp Bromley St

1.36 miles away|27 min walk

107 Heath St opp Bickford Ave

1.38 miles away|27 min walk

106 Heath St opp Bickford Ave

1.38 miles away|27 min walk

105 S Huntington Ave

1.55 miles away|30 min walk

Back of the Hill

1.55 miles away|30 min walk

100 S Huntington Ave

1.55 miles away|30 min walk

3867 Washington St opp Tollgate Way

1.61 miles away|31 min walk

Blue Hill Ave @ Castlegate Rd

1.88 miles away|36 min walk

Blue Hill Ave @ Franklin Park Rd

1.92 miles away|37 min walk

835 Huntington Ave opp Parker Hill Ave

1.92 miles away|37 min walk

Blue Hill Ave @ Ellington St

1.95 miles away|38 min walk

Blue Hill Ave @ Devon St

1.98 miles away|38 min walk

American Legion Hwy opp Franklin Hill Ave

1.99 miles away|39 min walk

Blue Hill Ave @ Brunswick St

1.99 miles away|39 min walk

American Legion Hwy @ Franklin Hill Ave

2.01 miles away|39 min walk

Blue Hill Ave @ Charlotte St

2.02 miles away|39 min walk

42A John Eliot Sq

2.06 miles away|40 min walk

205 Roxbury St

2.07 miles away|40 min walk

American Legion Hwy @ Blue Hill Ave

2.07 miles away|40 min walk

Blue Hill Ave @ Gaston St

2.09 miles away|41 min walk

75 St. Alphonsus St

2.11 miles away|41 min walk

Blue Hill Ave @ American Legion Hwy

2.11 miles away|41 min walk

American Legion Hwy opp Kingbird Rd

2.11 miles away|41 min walk

American Legion Hwy @ Kingbird Rd

2.13 miles away|41 min walk

1200 Centre St opp VFW Pkwy

2.14 miles away|42 min walk

677 Huntington Ave

2.15 miles away|42 min walk

Blue Hill Ave @ Angell St

2.21 miles away|43 min walk

Blue Hill Ave @ Harvard St

2.23 miles away|43 min walk

Blue Hill Ave @ Edgewood St

2.24 miles away|43 min walk

170 Walter St

2.28 miles away|44 min walk

Blue Hill Ave @ Clifford St

2.3 miles away|45 min walk

185 Columbia Rd

2.35 miles away|45 min walk

69 Annunciation Rd

2.35 miles away|46 min walk

American Legion Hwy @ Walk Hill St

2.36 miles away|46 min walk

144 Walter St opp Mendum St

2.37 miles away|46 min walk

Ave Louis Pasteur @ Longwood Ave

2.4 miles away|47 min walk

Annunciation Rd & Albert St

2.46 miles away|48 min walk

30 Annunciation Rd

2.49 miles away|48 min walk

American Legion Hwy @ Canterbury St

2.51 miles away|49 min walk

Blue Hill Ave @ Greenock St

2.57 miles away|50 min walk

Blue Hill Ave @ Callender St

2.59 miles away|50 min walk

Ave Louis Pasteur @ The Fenway

2.63 miles away|51 min walk

Ames St @ Westview St

2.64 miles away|51 min walk

1437 Centre St opp Ardale St

2.64 miles away|51 min walk

Blue Hill Ave @ Dudley St

2.65 miles away|51 min walk

Blue Hill Ave @ Arbutus St

2.7 miles away|52 min walk

The Neighbourhood: 288 Chestnut Ave

Jamaica Plain, a diverse and vibrant district in Suffolk County, MA, is renowned for its eclectic mix of attractions and natural beauty. The area boasts the lush Arnold Arboretum and the scenic Jamaica Pond, perfect for leisurely strolls and outdoor activities. Residents enjoy a thriving arts scene with numerous galleries and live music venues, as well as a variety of dining options ranging from cozy cafes to international cuisine. Public transportation is easily accessible with several bus lines and the Orange Line, providing convenient commuting options throughout the greater Boston area.

Next

Neighbourhood Description

Jamaica Plain, a diverse and vibrant district in Suffolk County, MA, is renowned for its eclectic mix of attractions and natural beauty. The area boasts the lush Arnold Arboretum and the scenic Jamaica Pond, perfect for leisurely strolls and outdoor activities. Residents enjoy a thriving arts scene with numerous galleries and live music venues, as well as a variety of dining options ranging from cozy cafes to international cuisine. Public transportation is easily accessible with several bus lines and the Orange Line, providing convenient commuting options throughout the greater Boston area.

Similar Buildings Nearby

Add to favoritesAdd to favorites (hover)
172-178 Green St
172-178 Green St, Boston, MA
Click to see listings
Add to favoritesAdd to favorites (hover)
172-178 Green St
172-178 Green Street, Boston, MA
Click to see listings
Add to favoritesAdd to favorites (hover)
996 Centre St
996 Centre St, Boston, MA
Click to see listings
Add to favoritesAdd to favorites (hover)
643 Chestnut Hill Ave
643 Chestnut Hill Avenue, Brookline, MA
Click to see listings
Add to favoritesAdd to favorites (hover)
172-178 Green St
172-178 Green St, Boston, MA
Click to see listings
Add to favoritesAdd to favorites (hover)
172-178 Green St
172-178 Green Street, Boston, MA
Click to see listings
Add to favoritesAdd to favorites (hover)
996 Centre St
996 Centre St, Boston, MA
Click to see listings
View All Similar Buildings

288 Chestnut Ave Demographics

Age Demographics

0–14 Years

15.19%

15–29 Years

22.94%

30–44 Years

27.23%

45–59 Years

16.11%

60+ Years

18.53%

Commute

34.33%

Transit

6.31%

Walk

35.79%

Drive

5.89%

Bike

Housing Ownership

38.22%

Owner Occupied

61.78%

Rental Units

Household Types

Single Family
28.86%
Multi Family
4.14%
Single Person
34.44%
Multi Person
65.56%

Average Income

Household:$9,745,465.75 /yr

Individual:$5,149,474.45 /yr

Education

Bachelors Degree26.89%
High School College14.66%
Diploma3.13%
Post Graduate32.58%
Others22.74%
Next

Education

Diploma3.13%
Post Graduate32.58%
Others22.74%
Get the HelloCondo Newsletter
Real-estate tips, insights, and market reports in your inbox.
Newsletter
  1. Home
  2. /Jamaica Plain, MA
  3. /
    288 Chestnut Ave
Nearby Cities
Newton Upper Falls
Buildings
1 Chestnut St
1 Louisburg Sq
10 Otis Pl
101 Chestnut St
101 Chestnut Street
101 Mount Vernon
17 Merrimac Way
185 Bussey St
19 Glade Condominiums
200-r Market St
24 Commonwealth Ave
24 Commonwealth Ave. 8
42 Belknap St
5 Washington St
51 VINE ROCK ST
9 Washington St
Edgewater Place
Jamaicaway Place
Tba
Neighborhoods
AuburndaleBeverly CoveBoston Common / Park Square
Castle HillCentral LynnChinatownCrow PointDowntown LowellFramingham CentreGloucester CrossingHillsideIsland HillLogan International AirportLower BelvidereMcIntire Historic DistrictSpring HillThe HighlandsWabanWest PeabodyWinthrop Highlands
ZIP Codes
014600146401867
0202602032020500206602071021280213602188021900219902201023240236702370024600247602558
Community
10-14 Park Vale Avenue Apartments10-14 Sydney Street Condominiums10-32A Glenville Avenue Apartments
100 Boatswains Way100 Captains Row100 Commandants Way100 High Street Condominiums100 Main Street100 Pond Street100 Riverway101 Prince Street101-107 Winthrop Road1022 Hancock Street103 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 2025. All Rights Reserved.