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Allston, Boston · Condominium Association

Chestershire Condominiums

A 25-unit condominium community in Allston, Boston.

Median Sale
$375k
Price / Sq Ft
$533
Avg Days on Mkt
30 days
Sold
6
HOA Range
$346–553/mo
Total Units
25

Market figures reflect closed sales over recent sales. Data sourced from MLS PIN.

Homes for Sale in Chestershire

No units are currently listed in Chestershire. Inventory here moves quickly — join the off-market list below to hear first when one comes up, or explore these similar nearby communities that have availability:

Overview

Chestershire Condominium is a 25-unit brick building located in Allston, Boston, positioned between Boston University and Packard's Corner. With recent median sales at $375,000 and an average market time of 30 days, this association represents an active market for both owner-occupants and investors seeking proximity to transit, retail, and university neighborhoods.

Amenities & Features

  • Parking: Deeded assigned parking spaces (standard and X-large options available)
  • Basement Storage: Private locked storage bins
  • Laundry: Common laundry facilities in basement
  • Building: Professionally managed brick construction with well-maintained common areas
  • Natural Light: Units feature abundant windows, many with multiple exposures
  • Hardwood Flooring: Present throughout most units
  • Kitchen: Eat-in kitchens with modern appliances (dishwasher and microwave noted in select units)
  • Bathrooms: Renovated baths with designer finishes and tile work
  • Bonus Spaces: Sunrooms/extended living areas in many units

Unit Types & Layouts

Chestershire's 25 units are predominantly 2-bedroom floor plans ranging from 735 to approximately 800+ square feet. The association includes several layout variations: standard 2-bedroom units, 2-bedroom-plus-office configurations (marketed as dual-use 3-bedroom rentals), and penthouse options. Ground-floor, elevated first-floor, and second-floor units are available. Split-bedroom layouts are featured in select units—ideal for shared occupancy. Many units include a bonus sunroom or study alcove adjacent to living areas, effectively expanding usable square footage.

The building maintains a 33% owner-occupied rate, indicating a mix of primary residences and rental investment properties. Historical rental rates documented in listings ranged from $950 to $1,800 monthly, reflecting demand from Boston University-area renters.

Living at Chestershire Condominium

Chestershire's location along Brighton Avenue and Chester Street places residents one block from the MBTA Green Line and multiple bus routes, enabling direct access to downtown Boston and surrounding neighborhoods. Packard's Corner—steps from the building—hosts restaurants, bars, music venues, and retail shops. Boston University's campus proximity supports both the owner-occupied and rental demographics. Commonwealth Avenue and Harvard Avenue provide additional commercial amenities and commuting alternatives. This positioning appeals to first-time buyers, young professionals, and investors capitalizing on stable rental demand near the university. Monthly HOA assessments range from approximately $346 to $552, scaling with unit size or amenities. The professionally managed building ensures consistent maintenance of common areas and building infrastructure.

Recent Sales

Sold Apr 202540 Chester
$480,000
40 Chester #B
2 bd · 1 ba · 755 sqft · 2 days
Sold Jan 202550 Chester St
$599,900
50 Chester St #6
2 bd · 1 ba · 735 sqft · 10 days
Sold Jul 202350 Chester St
$555,000
50 Chester St #7
3 bd · 1 ba · 735 sqft · 23 days
Sold Dec 201540 Chester
$270,000
40 Chester #B
2 bd · 1 ba · 755 sqft · 13 days
Sold Sep 201050 Chester St
$215,000
50 Chester St #7
2 bd · 1 ba · 735 sqft · 5 days
Sold Jun 201050 Chester St
$252,000
50 Chester St #3
2 bd · 1 ba · 735 sqft · 129 days

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About Your Chestershire Expert

JR

Justin Rollo

Chestershire Condominium Specialist · Signal Real Estate

Justin Rollo is a Massachusetts real estate expert with over a decade of experience and hundreds of South Shore transactions. He tracks every sale, pending, and price movement inside Chestershire — so whether you're buying into the community or thinking about selling, you're working with someone who knows this specific association inside and out.

Ask Justin about Chestershire →

Frequently Asked Questions

How much are condos at Chestershire Condominium selling for?

Over recent sales, units at Chestershire Condominium sold at a median of $375,000, about $533 per square foot.

What are the HOA / condo fees at Chestershire Condominium?

Monthly condo fees at Chestershire Condominium currently range from roughly $346.16 to $552.52, depending on unit size and what the association's master policy covers.

How many units are in Chestershire Condominium?

Chestershire Condominium is a 25-unit condominium association in Boston, MA.

How fast do condos sell at Chestershire Condominium?

Recent sales at Chestershire Condominium averaged about 30 days on market, with 6 closings in the period.