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281 Chestnut Avenue # 3, Boston MA 02130 - Preview 1 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 2 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 3 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 4 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 5 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 6 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 7 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 8 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 9 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 10 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 11 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 12 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 13 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 14 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 15 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 16 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 17
281 Chestnut Avenue # 3, Boston MA 02130 - Preview 1 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 2 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 3 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 4 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 5 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 6 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 7 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 8 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 9 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 10 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 11 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 12 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 13 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 14 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 15 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 16 281 Chestnut Avenue # 3, Boston MA 02130 - Preview 17

281 Chestnut Avenue # 3, Boston MA 02130

Boston, MA 02130 • Jamaica Plain
$3,850/mo
2
Beds
1
Baths
993
Sq Ft
993
Lot Sq Ft
1905
Year Built
Condominium
Type
11 hours 37 minutes
Time on Market
Active Open House Listed Jul 21, 2026 • MLS# 73552515 Copied! • Updated Jul 21, 2026

Open House Schedule

22
Jul
Wednesday, July 22
4:00 PM - 6:00 PM EDT

About this home

Beautifully renovated penthouse condominium in the heart of Jamaica Plain, offering a rare combination of architectural charm, modern updates, and exceptional outdoor living. This sun-filled 2-bedroom residence features soaring ceilings, exposed brick details, hardwood floors, updated kitchen, and in-unit laundry. The inviting open layout creates an ideal space for both everyday living and entertaining. Enjoy the luxury of a private roof deck and additional rear deck—perfect for morning coffee, gardening, or relaxing under the stars. Located on one of Jamaica Plain’s most desirable residential streets, this home is steps from Centre Street’s restaurants, shops, and cafés, with easy access to Jamaica Pond, the Arnold Arboretum, Green Street T Station, and Forest Hills. A truly special opportunity to experience the best of JP living in a distinctive condominium setting. Parking available on street and for a fee next door.

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Property History

Market Insights

99.4%
Price Range
1
Previous Sales

Property Timeline

🏠
Listed for Sale
Jul 21, 2026
$3,850
Original listing
Office: LandVest, Inc.
Previous Transaction - MLS #72739116
Full transaction history available when tracking began
🏷️
Previously Sold
Nov 30, 2020
$650,000
MLS #72739116
View Listing →

Tax History

Year Taxes Assessment
Tax history not available

Facts & Features

Home Facts

Type Residential Lease
Style Condominium
Year Built 1905
Living Area 993 sq ft
Lot Size 993 sq ft
Bedrooms 2
Full Baths 1
Total Rooms 4

Rental Details

Available Aug 15, 2026
Lease Term Term of Rental(12)
Rent Includes Water, Sewer
Security Deposit $3,850
Required First MonthLast MonthDepositReferencesInsurance
Pets Yes w/ Restrictions
Pet Policy Dogs OKCats OKRestrictions Apply
Heating Natural Gas, Baseboard
Cooling None
Flooring None
Appliances Range, Dishwasher, Refrigerator, Washer, Dryer
Fireplace None
Basement None
Laundry In Unit
Features None
Construction None
Architecture None
Roof None
Features Deck, Deck - Roof
Pool None
Spa None
Fencing None
Patio/Porch Deck, Deck - Roof
Features None

Utilities

Electric None
Water None
Sewer None
Gas None
Other None

Building & Pet Policy

Fee Includes None
Amenities None
Optional Fee Includes None
Possession None
Accepted Financing None
Structure Type []
Unit/Building 3
Sq Ft Source Other
Sq Ft Disclosures Additional storage unit in basement.
Documents None
County Suffolk

Property Overview

Property Type
Condominium
Listing Type
For Rent
Year Built
1905
Bedrooms
2
Full Bathrooms
1
Living Area
993 sq ft
Total Rooms
4
Entry Level
3

Room Details

Other Floor

Bathroom1
Bedroom5
Bedroom4
Bedroom3
Dining Room
Kitchen
Bathroom2
Bedroom2
Living Room
Bathroom3
Master Bedroom
Office
Family Room
Master Bathroom
No

Interior Features

Flooring:
Appliances: Range, Dishwasher, Refrigerator, Washer, Dryer
Interior Features:
Windows:
Basement:
Laundry: In Unit
Security:

Construction & Materials

Year Built: 1905
Structure Type:
Exterior Materials:
Roof:
Foundation:

Heating, Cooling & Utilities

Heating: Natural Gas, Baseboard
Cooling:
Hot Water:
Water Source:
Sewer:
Energy Features:

Exterior & Lot

Exterior Features: Deck, Deck - Roof
Patio & Porch: Deck, Deck - Roof
Fencing:
Other Structures:
Lot Features:
Road Surface:

Parking & Garage

Parking Features:
School District
Boston School District local
C-
🎓 Where Graduates Go Class of 2021
52% attend college
38% 4-Year 14% 2-Year 7% Out of State 7% Working
⚠ School Safety 2024-25
3.7% Above Average
3.2% Suspensions 0.3% In-School 0.5% Emergency
↓ 1.8% below state avg
E

Elementary Schools

10 schools
C
Curley K-8 School
0.4 mi | #268 of 352 | Score: 34.7
Dropped 57 spots from last year
-23.5 below state avg
902 students Very Diverse
Diverse Student Body
Grades PK-08
C-
Mendell Elementary School
0.5 mi | #674 of 824 | Score: 37.2
Dropped 147 spots from last year
-21 below state avg
309 students Very Diverse
Diverse Student Body
Grades PK-06
Neighborhood School
0.5 mi
Grades PK-06
C-
Hernandez Elementary School
0.6 mi | #692 of 824 | Score: 36.2
Dropped 88 spots from last year
-22 below state avg
372 students Moderate
Grades PK-06
C
John F Kennedy School
0.6 mi | #633 of 824 | Score: 39.2
Dropped 58 spots from last year
-19 below state avg
399 students Diverse
Grades PK-06
Parkside Christian Academy/Cross Factor Academy
0.7 mi
Grades PK-12
F
Ellis Elementary School
0.9 mi | #817 of 824 | Score: 24.7
Dropped 57 spots from last year
-33.5 below state avg
391 students Moderate
Grades PK-06
F
Hennigan Elementary School
0.9 mi | #811 of 824 | Score: 26.0
Improved 2 spots from last year
-32.2 below state avg
472 students Diverse
Grades PK-06
F
Trotter Elementary School
1.1 mi | #794 of 824 | Score: 29.2
Dropped 6 spots from last year
-29 below state avg
352 students Diverse
Grades PK-06
Italian Home For Children
1.1 mi
Grades PK-09
M

Middle Schools

10 schools
Nativity Prep School
0.7 mi
Grades 05-08
F
Higginson/Lewis K-8 School
1.3 mi | #349 of 352 | Score: 23.6
Improved 3 spots from last year
-34.6 below state avg
213 students Diverse
Grades 03-08
Mother Caroline Academy
1.4 mi
Grades 05-08
Dearborn Middle School
1.5 mi
A
Uncommon Schools - Roxbury Preparatory Dorchester Campus Middle School
1.9 mi | #4 of 16 | Score: 41.9
Improved 187 spots from last year
-16.3 below state avg
1,126 students Diverse
Rising School College Ready Curriculum
Grades 05-08
Epiphany School
2.6 mi
Grades 05-08
Middle School Academy
3.4 mi
C
Ohrenberger School
4.1 mi | #265 of 352 | Score: 34.9
Improved 20 spots from last year
-23.3 below state avg
477 students Diverse
Rising School Diverse Student Body
Grades 03-08
Timilty Middle
1.5 mi
Frederick Pilot Middle
1.8 mi
H

High Schools

10 schools
Meridian Academy
0.3 mi
Grades 06-09
B-
Margarita Muniz Academy
0.5 mi | #14 of 25 | Score: 31.3
Improved 349 spots from last year
-26.9 below state avg
428 students Less Diverse
Strong AP Program Rising School
Grades 07-12
D
English High School
0.5 mi | #324 of 346 | Score: 29.7
Improved 34 spots from last year
-28.5 below state avg
720 students Moderate
8 sports • 332 athletes
Rising School Career Tech Programs
Grades 07-12
A+
Boston Latin Academy
1.3 mi | #2 of 25 | Score: 63.9
Improved 214 spots from last year
+5.7 above state avg
1,693 students Very Diverse
17 sports • 1,298 athletes
High Graduation Rate Rising School Strong Athletics Diverse Student Body
Grades 07-12
A-
O'Bryant School of Math & Science
1.6 mi | #90 of 346 | Score: 61.1
Improved 94 spots from last year
+2.9 above state avg
1,509 students Very Diverse
High Graduation Rate Rising School College Ready Curriculum Diverse Student Body
Grades 07-12
B
Dearborn STEM Academy
1.7 mi | #13 of 25 | Score: 31.7
Improved 356 spots from last year
-26.6 below state avg
565 students Diverse
10 sports • 242 athletes
Early College Program Rising School
Grades 07-12
A+
Boston Latin School
1.8 mi | #19 of 346 | Score: 73.3
Improved 61 spots from last year
+15.1 above state avg
2,424 students Very Diverse
18 sports • 2,006 athletes
Strong AP Program High Graduation Rate Rising School Strong Athletics
Grades 07-12
B+
TechBoston Academy
2.6 mi | #11 of 25 | Score: 34.1
Improved 349 spots from last year
-24.1 below state avg
850 students Diverse
Rising School
Grades 07-12
F
Albert D Holland School of Technology
2.7 mi | #333 of 346 | Score: 25.8
Improved 28 spots from last year
-32.4 below state avg
399 students Diverse
Rising School
Grades 07-12
Cathedral High School
2.8 mi
9 sports • 430 athletes
Grades 07-12
Learn about these ratings
School data provided by BMN Schools

Location

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Neighborhood

Jamaica Plain

281 Chestnut Avenue # 3, Boston MA 02130

Boston, MA 02130

Listing Information

Listing Agent Leslye Fligor
Listing Office LandVest, Inc.
Office Phone 617-723-1800
Agent MLS ID BB985511
Office MLS ID C03800
Listing Data Updated Jul 21, 2026 8:09 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

Contact Us

BMN Boston Real Estate
BMN Boston Real Estate
Douglas Elliman
(617) 800 - 9008 contact@bmnboston.com
Ask about this property — free, no obligation.

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281 Chestnut Avenue # 3, Boston MA 02130 - Photo 1 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 2 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 3 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 4 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 5 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 6 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 7 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 8 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 9 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 10 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 11 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 12 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 13 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 14 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 15 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 16 281 Chestnut Avenue # 3, Boston MA 02130 - Photo 17
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