A 35-unit condominium community in West Roxbury, Boston.
Market figures reflect closed sales over recent sales. Data sourced from MLS PIN.
# Chestnut Hill Woods Condominium Association
Chestnut Hill Woods is a 35-unit condominium association straddling the West Roxbury and Chestnut Hill neighborhoods, offering townhouse-style living in a country setting with urban proximity. Recent market activity shows a median sale price of $645,000, with units moving in approximately 20 days on average at $295 per square foot.
Chestnut Hill Woods offers primarily two-bedroom, three-bedroom, and four-bedroom townhouses. Many units feature loft areas with skylights, creating flexible bonus space. Two-bedroom units often include a dedicated loft or office area and 2.5 bathrooms. Three-bedroom units typically span 2,100 to 2,400+ square feet across three levels, with multiple full bathrooms. Four-bedroom townhouses represent premium end units and corner units, generally featuring 2.5 baths and substantial square footage.
Most units include master suites with ensuite baths and generous closets. Kitchens have been updated in numerous units with modern cabinetry (cherry or European styles), granite countertops, and stainless appliances. First floors commonly open to dining and living areas with direct deck access.
The association occupies a location positioned between West Roxbury and Chestnut Hill, near Chestnut Hill Square and proximity to The Street shopping area. Residents benefit from what listings describe as a "country setting" combined with easy access to city conveniences and major commuter routes. The community borders conservation land, providing a secluded aesthetic despite urban accessibility.
The complex appeals to those seeking townhouse ownership with the maintenance and governance structure of condominium living. Recent renovations across multiple units—including 2007 and 2021 renovations cited in listings—suggest ongoing investment in the property. Many units feature updated mechanical systems, newer roofing, and contemporary HVAC installations, indicating owner reinvestment in building systems.
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 Chestnut Hill Woods — 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 Chestnut Hill Woods →Over recent sales, units at Chestnut Hill Woods sold at a median of $645,000, about $295 per square foot.
Chestnut Hill Woods is a 35-unit condominium association in Boston, MA.
Recent sales at Chestnut Hill Woods averaged about 20 days on market, with 6 closings in the period.