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.
Pending
$2,850,000
44 Valley Rd, Brookline, MA 02467
6beds
2,992sqft
Single Family Residence
Built in 1938
0.33 Acres Lot
$2,833,800 Zestimate®
$953/sqft
$-- HOA
What's special
Dedicated laundry areaAttached two-car garageFormal dining roomFinished lower levelSought-after first-floor retreatVersatile recreation roomStainless steel appliances
- 26 days
- 1,299
- 59
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
The Kelleher Spalding Team 617-426-6900,
Gibson Sotheby's International Realty 617-426-6900
Source: MLS PIN,MLS#: 73558881
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Features: Bathroom - Full, Closet, Flooring - Wall to Wall Carpet, Recessed Lighting, Lighting - Overhead, Closet - Double
- Level: Second
Bedroom 2
- Features: Bathroom - Full, Flooring - Hardwood, Recessed Lighting, Lighting - Overhead
- Level: First
Bedroom 3
- Features: Closet, Flooring - Wall to Wall Carpet
- Level: Second
Bedroom 4
- Features: Closet, Flooring - Hardwood
- Level: Second
Bedroom 5
- Features: Closet, Flooring - Hardwood
- Level: Second
Primary bathroom
- Features: Yes
Bathroom 1
- Features: 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
- Level: Second
Bathroom 2
- Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Skylight, Flooring - Stone/Ceramic Tile, Cabinets - Upgraded, Remodeled, Beadboard
- Level: Second
Bathroom 3
- Features: Bathroom - Full, Bathroom - Tiled With Shower Stall, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Countertops - Upgraded, Remodeled, Lighting - Sconce
- Level: First
Dining room
- Features: Flooring - Hardwood, French Doors, Exterior Access, Recessed Lighting, Remodeled, Lighting - Sconce, Crown Molding
- Level: Main,First
Kitchen
- Features: Flooring - Hardwood, Countertops - Stone/Granite/Solid, Kitchen Island, Cabinets - Upgraded, Recessed Lighting, Remodeled, Stainless Steel Appliances, Gas Stove, Lighting - Pendant
- Level: First
Living room
- Features: Flooring - Hardwood, Recessed Lighting, Wainscoting, Crown Molding, Decorative Molding
- Level: First
Heating
- Baseboard, Natural Gas
Cooling
- Central Air
Appliances
- Included: Gas Water Heater, Oven, Dishwasher, Disposal, Microwave, Range, Refrigerator, Washer, Dryer, Range Hood
- Laundry: In Basement
Features
- Closet, Closet/Cabinets - Custom Built, Recessed Lighting, Wainscoting, Crown Molding, Decorative Molding, Den
- Flooring: Hardwood, Flooring - Hardwood
- Basement: Full,Finished,Garage Access
- Number of fireplaces: 2
- Fireplace features: Dining Room, Living Room
Interior area
- Total structure area: 2,992
- Total interior livable area: 2,992 sqft
- Finished area above ground: 2,992
Video & virtual tour
Property
Parking
- Total spaces: 4
- Parking features: Attached, Garage Door Opener, Off Street, Paved
- Attached garage spaces: 2
- Uncovered spaces: 2
Features
- Exterior features: Professional Landscaping
Lot
- Size: 0.33 Acres
- Features: Gentle Sloping
Details
- Parcel number: M:0278 B:0015 L:0000,39337
- Zoning: S15
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape
- Property subtype: Single Family Residence
Materials
- Foundation: Concrete Perimeter
Condition
- Year built: 1938
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: for Gas Range
Community & HOA
Community
- Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Golf, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School
HOA
- Has HOA: No
Location
- Region: Brookline
Financial & listing details
- Price per square foot: $953/sqft
- Tax assessed value: $2,465,300
- Annual tax amount: $25,245
- Date on market: 8/4/2026
Estimated market value
$2,833,800
$2.69M - $2.98M
$7,961/mo
Price history
| Date | Event | Price |
|---|---|---|
| 8/25/2026 | Pending sale | $2,850,000$953/sqft |
Source: MLS PIN #73558881 Report a problem | ||
| 8/11/2026 | Contingent | $2,850,000$953/sqft |
Source: MLS PIN #73558881 Report a problem | ||
| 8/4/2026 | Listed for sale | $2,850,000+570.6%$953/sqft |
Source: MLS PIN #73558881 Report a problem | ||
| 2/28/1991 | Sold | $425,000$142/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $23,490 +5% | $2,379,900 +3.9% |
| 2024 | $22,381 +10.2% | $2,290,800 +12.5% |
| 2023 | $20,309 +2.7% | $2,037,000 +5% |
| 2022 | $19,768 +8.1% | $1,939,900 +4% |
| 2021 | $18,281 +9.7% | $1,865,400 +5.8% |
| 2020 | $16,669 +5.9% | $1,763,900 +5% |
| 2019 | $15,741 +0.3% | $1,679,900 +1.3% |
| 2018 | $15,691 +1.5% | $1,658,700 +6% |
| 2017 | $15,460 +1.5% | $1,564,800 +7% |
| 2016 | $15,239 +5% | $1,462,500 +7.6% |
| 2015 | $14,518 +0.3% | $1,359,400 +7% |
| 2014 | $14,477 +0.7% | $1,271,000 +3% |
| 2013 | $14,376 +2.2% | $1,234,000 |
| 2012 | $14,068 +0.8% | $1,234,000 -0.1% |
| 2011 | $13,952 +3% | $1,234,700 |
| 2010 | $13,545 +2.8% | $1,234,700 +0.2% |
| 2009 | $13,178 +6.4% | $1,232,700 +1.3% |
| 2008 | $12,387 +0.8% | $1,216,800 -3.6% |
| 2007 | $12,284 +1.5% | $1,262,500 -0.4% |
| 2006 | $12,103 +6% | $1,267,300 +13.5% |
| 2005 | $11,418 +3% | $1,116,100 +7% |
| 2004 | $11,088 +4.3% | $1,043,100 +10% |
| 2003 | $10,629 -3.1% | $948,200 +11.6% |
| 2002 | $10,965 +0.2% | $850,000 +31.4% |
| 1999 | $10,941 | $647,000 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: Chestnut Hill
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