
44 Valley Rd Brookline — Photo 1 of 42
$2,850,000
Brookline, MA 02467 — Chestnut Hill
Beds
6
Baths
3.5
SqFt
2,992
Style
Single Family
Built
1938
Discover timeless elegance and exceptional versatility in this beautifully updated 1938 Cape, thoughtfully designed for today's discerning family. Offering 6 bedrooms and 3.5 baths, the home features two primary bedrooms with private ensuite baths, including a sought-after first-floor retreat ideal for multigenerational living, guests, or an au pair. The chef's kitchen is appointed with stainless steel appliances, a gas range, wall oven, stone countertops, and a center island with seating for three. A welcoming den, formal dining room, and sun-filled breakfast area provide inviting settings for both everyday life and elegant entertaining. The finished lower level offers a versatile recreation room with a dedicated laundry area. Completing the home are an attached two-car garage and two additional off-street parking spaces, blending classic New England charm with modern comfort and convenience. Close to Roland Hayes School & Brookline High School, Route 9, Chestnut Hill Reservoir, Golf Courses, Green Line (MBTA) and The Mall at Chestnut Hill. Quick drives to Newton Centre or Brookline hubs for everyday groceries and dining.
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Brookline, MA.
Gas Water Heater • Oven • Dishwasher • Disposal • Microwave • Range • Refrigerator • Washer • Dryer • Range Hood
Public Transportation • Shopping • Park • Walk/Jog Trails • Golf • Bike Path
Flooring - Hardwood, Recessed Lighting, Wainscoting, Crown Molding, Decorative Molding
Flooring - Hardwood, French Doors, Exterior Access, Recessed Lighting, Remodeled, Lighting - Sconce, Crown Molding
Flooring - Hardwood, Countertops - Stone/Granite/Solid, Kitchen Island, Cabinets - Upgraded, Recessed Lighting, Remodeled, Stainless Steel Appliances, Gas Stove, Lighting - Pendant
Bathroom - Full, Closet, Flooring - Wall to Wall Carpet, Recessed Lighting, Lighting - Overhead, Closet - Double
Closet, Flooring - Wall to Wall Carpet
Closet, Flooring - Hardwood
Closet, Flooring - Hardwood
Bathroom - Full, Bathroom - Tiled With Shower Stall, Bathroom - Tiled With Tub, Flooring - Stone/Ceramic Tile, Window(s) - Bay/Bow/Box, Countertops - Stone/Granite/Solid, Recessed Lighting
Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Skylight, Flooring - Stone/Ceramic Tile, Cabinets - Upgraded, Remodeled, Beadboard
Bathroom - Full, Bathroom - Tiled With Shower Stall, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Countertops - Upgraded, Remodeled, Lighting - Sconce
23,001
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
$169K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
32.3%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
1,189 housing units permitted in the last 12 months (+21% vs the prior 12 months) — 706 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 2,992 sq ft principal dwelling). Lot size: 14,488 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: The Kelleher Spalding Team
Listing Office: Gibson Sotheby's International Realty
MLS® Number: 73558881
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