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Jeff Smith
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540 Chestnut Hill Ave, Brookline, MA 02445

$4,250,000
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New to the Market Active
BEDS5 BATHS4 full 1 partial SQUARE FEET6,419 MLS#73504708
STATUSActive PROPERTY TYPEResidential - Single Family

Property Description

Beautifully restored 1900s French-style residence on an acre of land in Brooklines coveted Fisher Hill. Over 6,000 sq ft of living space featuring 5 bedrooms and 4.5 bathrooms. Inviting foyer with fireplace & custom bookshelves, an impressive great room with 15 ceilings & fireplace, an elegant living room with period details including a fireplace, and a dining room with French doors to a stone terrace. House features a chefs kitchen with high-end appliances and two spacious first-floor primary suites offering serene terrace views. The second floor has two bedrooms and a full bathroom. There is also a fifth bedroom with a private entrance, perfect for au pair or in-law. Four fireplaces, stone terraces, sweeping lawns, and lush landscaping complete this exceptional property, close to Brookline Reservoir, Chestnut Hill shops, Green Line public transportation, major highways & Boston.

540 Chestnut Hill Ave | MLS# 73504708

This single family home located at 540 Chestnut Hill Ave, Brookline, MA 02445 is currently listed for sale with an asking price of $4,250,000. This property was built in 1900 and has 5 bedrooms and 4 full and 1 partial baths with 6419 sq. ft. Search Brookline real estate on jeffsmith.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Full, Walk-Out Access, Interior Entry, Sump Pump, Concrete, Unfinished
Cooling: Central Air
Fenced: Yes
Fireplaces: 4
Garage: 2 car attached
Heating: Forced Air, Natural Gas
Home Style: French Colonial
Lot Size: 1.03 Acres
Roof Type: Slate, Rubber
Taxes: $59,883
Year Built: 1900

Amenities

Closet/Cabinets - Custom Built
Lighting - Overhead
Crown Molding
Bathroom - Full
Recessed Lighting
Bathroom - Half
Entrance Foyer
Bathroom
Entry Hall
Office
Patio
Rain Gutters
Professional Landscaping
Sprinkler System

Feature Descriptions

Appliances: Gas Water Heater, Oven, Dishwasher, Disposal, Range, Refrigerator, Washer, Dryer
Building Area Total: 6419
Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Highway Access, Private School, Public School, T-Station
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Dining Room: Flooring - Wood, French Doors, Exterior Access, Lighting - Sconce
Door Features: French Doors
Family Room: Flooring - Hardwood, French Doors, Exterior Access, Recessed Lighting
Fencing: Fenced/Enclosed
Fireplace Features: Family Room, Living Room, Bedroom
Fireplace Y/N: Yes
Flooring: Wood, Tile, Carpet, Hardwood, Flooring - Hardwood
GarageY/N: Yes
HeatingY/N: 1
Kitchen: Countertops - Stone/Granite/Solid, Breakfast Bar / Nook, Cabinets - Upgraded, Recessed Lighting, Remodeled, Stainless Steel Appliances
Laundry: In Basement
Living Room: Flooring - Hardwood, Window(s) - Bay/Bow/Box, Chair Rail
Master Bathroom: Yes
Master Bedroom: Bathroom - Full, Bathroom - Double Vanity/Sink, Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Wall to Wall Carpet, Dressing Room
Office: Flooring - Hardwood, Recessed Lighting, Crown Molding
Open Parking Y/N: Yes
Parcel Number: 38925
Parking Features: Attached, Garage Door Opener, Paved Drive
Parking Total: 8
Patio And Porch: Patio
Property Attached Y/N: 1
Rooms Total: 12
Security: yes
Security Features: Security System
Sewer: Public Sewer
Water: Public

Room Sizes

Bedroom 2: 29.80 X 20.00 Level - First
Bedroom 3: 16.80 X 12.00 Level - Second
Bedroom 4: 13.30 X 13.20 Level - Second
Bedroom 5: 14.60 X 10.10 Level - Second
Dining Room: 17.20 X 11.40 Level - First
Family Room: 30.30 X 21.20 Level - First
Kitchen: 26.00 X 7.90 Level - First
Living Room: 23.80 X 15.00 Level - First
Primary Bedroom: 25.40 X 15.20 Level - First
Office: 13.20 X 11.30 Level - First

Local Schools

High School: Brookline High School
Elementary School: Runkle

Listed By / Shown By

Listed By

Agency Name: Compass
Agency Phone: 617-752-6845
Agent Name: The Duffy Group

Shown By

Agent Name: Jeff Smith
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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Estimated Payment

$ 15,688.49 per month $9,458.66 Principal & Interest $4,990.25 Property Tax $1,239.58 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/21/2026. The listing information on this page last changed on 04/21/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 04/21/2026 12:02:36 AM EST) or MLSPIN MLS (last updated Mon 04/20/2026 11:38:20 PM EST) or Prime MLS (last updated Mon 04/20/2026 5:18:22 PM EST) or MREIS (last updated Mon 04/20/2026 11:55:16 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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