Interior Features
- Ceiling Fan(s)
- Pantry
- Bathroom with Tub
- Studio
- Bathroom with Shower Stall
- Living Room
- Dining Room
- Kitchen
- FlooringHardwood, Wood
- Window FeaturesInsulated Windows
‹ Back to Brookline
Questions about this home? Call or text ![]()
Keith Wade at 603-818-7976.
Keith Wade at 603-818-7976.Show all 33 photos
For Sale · 75 days↗ Share♡ Favorite
$1,750,000↓ $50K price cut 10-02-2026
86 Chestnut St, Brookline, MA 02445 Brookline
MULTI-FAMILY
Home Highlights
Finished Basement500 finished sq ft
41% Below Area $/Sq Ft$475 vs $800, the Brookline median
Minimal Flood RiskFEMA Zone X (unshaded)
2 Zoned SchoolsRated up to 9/10
About This Home
Investors, take note! Don't miss this exceptional opportunity to own a three-family property in one of Brookline's most sought-after locations. Situated near Brookline Village, this property is just a 12-minute walk to the Green Line, providing convenient access to Fenway, Downtown Boston, and beyond. The MBTA Route 60 bus to the Longwood Medical Area is just steps from the front door.Enjoy a highly walkable neighborhood with easy access to grocery stores, restaurants, parks, walking trails, and all the amenities that make Brookline such a desirable place to live.The rear porches offer beautiful city views, and with modern updates, this classic property has the potential to truly shine! Large driveway accommodates multiple cars for easy off street parking. Enjoy the ample yard space for grilling, bonfires, or just taking in the fresh air! Located in a community renowned for its exceptional schools, vibrant neighborhoods, and unbeatable location, this is an investment opportunity you won't want to miss.
Read moreKey Details
MLS #73559809
Monthly HOA
Price / Sq Ft$475
Property TypeMulti-Family
Subdivision
Tax (2026)$16,475
Assessed Value$1,608,900
How This Home Compares
vs. the 288 homes for sale in BrooklinePrice$1,750,000
Median $1,649,500
$350,000
$36,000,000
6% above the median Brookline home ($1,649,500).
Price per Sq Ft$475
Median $800
$424
$1,887
41% below the median Brookline home ($800).
Home Size3,681 sq ft
Median 1,815 sq ft
405 sq ft
45,935 sq ft
103% larger than the median Brookline home (1,815 sq ft).
Lot Size0.10 acres
Median 0.30 acres
0.02 acres
22.96 acres
65% smaller than the median Brookline home (0.30 acres).
Days on Market75 days
Median 55 days
0 days
375 days
On the market longer than most homes here (55 days median).
86 Chestnut St at a Glance
MLS# 73559809
Offered at $1,750,000, this 9 bed, 4 bath home has 3,681 square feet of living space and was built in 1900. It sits in Brookline, zoned for William H Lincoln School and Brookline High School.
Want to see it in person? Schedule a showing or call Keith Wade at 603-818-7976.
Property Details
Kitchen and Appliances
- Oven
- Dishwasher
- Refrigerator
- Range
Exterior and Lot
- Patio and Porch FeaturesDeck - Wood
- Road Frontage TypePublic
- Deck
Garage and Parking
- Parking FeaturesOff Street
- Parking Total6
Building and Construction
- Total Square Feet Living3,681
- Year Built1900
- Above Grade Finished Area3,181
- BelowGradeFinishedArea500
- Building Area Total3,681
- Building Area UnitsSquare Feet
- Construction MaterialsFrame
- Foundation DetailsGranite
- Levels3
- Property Age126
- RoofShingle
- Levels or Stories3
- Building Total Stories3
- Year Built DetailsActual
- Year Built SourcePublic Records
Bedrooms and Bathrooms
- Bedrooms9
- Total Bathrooms4
- Full Bathrooms4
Other Rooms
- Total Rooms20
- Basement FeaturesFull, Finished
Heating and Cooling
- Heating FeaturesNatural Gas
- Heating
Land Info
- Lot DescriptionCorner Lot
- Lot Size Acres0.103306
- Lot Size Square Feet4,500
Rental Info
- Gross Income96,000
- Rent IncludesUnit 2(Water), Unit 3(Electric, Water)
Multi-Unit Info
- Number of Units3
Amenities and Community Features
- Community FeaturesPublic Transportation, T-Station
Other Property Info
- Annual Tax Amount16,475
- Source Listing StatusPrice Changed
- CountyNorfolk County
- DirectionsUse Gps
- Tax Year2026
- Source Property TypeResidential Income
- Home WarrantyNo
- Parcel NumberM:0316 B:0020 L:0000,40929
- Postal Code Plus 47862
- ZoningM10
- Property Subtype3 Family
Commercial Info
- Net Operating Income96,000
Utilities
- ElectricCircuit Breakers
- SewerPublic Sewer
- Water SourcePublic
Schools Zoned for This Home
Brookline School District
elementary & middle · K-8Photo: webWilliam H Lincoln School
9/10
high · 9-12Photo: webBrookline High School
8/10
Mortgage Calculator
For 86 Chestnut St, Brookline, MA 02445Estimated Monthly Payment
/ month
Loan Amount
Down Payment
Down PaymentLoan Amount
$
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Today's national average$
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Rate from today's national average (7.28%). Includes estimated property taxes and HOA; homeowners insurance not included. An estimate, not a loan offer.
Price History
Listed For
$1,750,000on 10-02-2026
Last Sold $800,000 on 04-15-2009
First Recorded Sale $800,000 in 2009
SoldListed
| Date | Event | Price | Change |
|---|---|---|---|
| 10-02-2026MLSPrice Changed | Price Changed | $1,750,000 | −$50,000−2.8% |
| MLSListed | Listed | $1,800,000 | +$1,000,000+125.0% |
| 04-15-2009MLSSold | Sold | $800,000 | −$60,000−7.0% |
| MLSListed | Listed | $860,000 | — |
2026 Property Tax
$16,475per year
Assessed Value $1,608,900
Tax records back to 2003
| Year | Property Tax | Assessed Value |
|---|---|---|
| 2026 | $16,475 | $1,608,900 |
| 2024 | $15,676 | $1,604,500 |
| 2023 | $15,147 | $1,519,300 |
| 2022 | $14,744 | $1,446,900 |
| 2021 | $13,635 | $1,391,300 |
| 2020 | $12,874 | $1,362,300 |
| 2019 | $12,157 | $1,297,400 |
| 2018 | $11,512 | $1,216,900 |
| 2017 | $11,131 | $1,126,600 |
| 2016 | $10,672 | $1,024,200 |
| 2015 | $9,944 | $931,100 |
| 2014 | $10,012 | $879,000 |
| 2006 | $7,961 | $833,600 |
| 2005 | $7,319 | $715,400 |
| 2004 | $7,106 | $668,500 |
| 2003 | $6,812 | $607,700 |
Sale prices from public records; list prices from the MLS. Taxes shown are for the prior owner and can change after a sale.
86 Chestnut St FAQ
At $1,750,000, the asking price of 86 Chestnut St is 6.1% above the median asking price of $1,649,500 for homes for sale in Brookline.
- Its price per square foot is $475, 40.6% below the median of $800 for homes for sale in Brookline.
- That is the 7th lowest price per square foot of the 284 homes for sale in Brookline that list their size.
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Listing Information Last Updated 10-19-2026