86 Chestnut St, Brookline MA 02445
Brookline, MA 02445
$1,800,000
Est. $10,675/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
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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.
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Recently Sold Nearby
Property History
Market Insights
Property Timeline
Back On Market
Sep 2, 2026
Active
Showing Instructions Updated
Sep 2, 2026
New showing requirements
Pending Sale
Aug 21, 2026
Offer accepted, sale pending
Listed for Sale
Aug 5, 2026
$1,800,000
Original listing
Office: Red Tree Real Estate
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 09/02/2026 | • Back On Market | - | - | - | Active |
| 09/02/2026 | 👁️ Showing Instructions Updated | - | - | - | New showing requirements |
| 08/21/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 08/05/2026 | 🏠 Listed for Sale | $1,800,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $16,475 | $1,608,900 |
Financial Details
Annual Property Tax
$16,475
Tax Year 2026
Assessed Value
$1,608,900
Facts & Features
Home Facts
Type
Residential Income
Style
3 Family
Year Built
1900
Living Area
3,681 sq ft
Lot Size
0.10 acres
Stories
3
Bedrooms
10
Full Baths
4
Total Rooms
19
Investment Metrics
Units
3
Unit 1 Rent
$2,500/mo · Y
Unit 2 Rent
$2,500/mo · Y
Unit 3 Rent
$3,000/mo · Y
Unit 4 Rent
— · N
Total Monthly Rent
$8,000/mo
Gross Income
$96,000
Net Operating Income
$96,000
Cap Rate
5.33%
Interior
Heating
Natural Gas
Cooling
None
Flooring
Hardwood, Wood
Appliances
Oven, Dishwasher, Refrigerator, Range
Fireplace
None
Basement
Full, Finished
Laundry
None
Features
Ceiling Fan(s), Pantry, Bathroom With Tub, Studio, Bathroom With Shower Stall, Living Room, Dining Room, Kitchen
Exterior
Construction
Frame
Architecture
None
Roof
Shingle
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
Deck - Wood
Parking
Features
Off Street
Total Spaces
6
Utilities
Electric
Circuit Breakers
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$16,475
Assessed Value
$1,608,900
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
Property Is Being Sold As Is. Buyer And Buyer Agent To Do All Due Diligence.first Floor Unit #1 Is Metered With The Common Area. Lease For Unit #2 Is Valid Until August 31st. 2027 There Is No Lease In Place For Units #1 & #3 They Are Occupied With Paying Tenants.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
House Color
White
Sq Ft Source
Public Record
Sq Ft Disclosures
Three family building
Documents
None
County
Norfolk
Total market time (incl. prior listings)
25 days
Property Overview
Property Type
3 Family
Listing Type
For Sale
Year Built
1900
Bedrooms
10
Full Bathrooms
4
Living Area
3,681 sq ft
Total Rooms
19
Stories
3
Levels
3
Floor Layout
Interactive room guide
Floor Layout
Finished Area
3,181 sq ft above grade
500 sq ft below grade
Display Options
Outdoor Areas
Patio & porchDeck - Wood
Room Markers
OOffice (1)
KKitchen (1)
BRBedroom (5)
BABathroom (4)
DDining (1)
LLiving (2)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Hardwood, Wood
Appliances:
Oven, Dishwasher, Refrigerator, Range
Interior Features:
Ceiling Fan(s), Pantry, Bathroom With Tub, Studio, Bathroom with Shower Stall, Living Room, Dining Room, Kitchen
Windows:
Insulated Windows
Basement:
Full, Finished
Laundry:
Security:
Construction & Materials
Year Built:
1900
Structure Type:
Exterior Materials:
Frame
Roof:
Shingle
Foundation:
Granite
Stories:
3
Heating, Cooling & Utilities
Heating:
Natural Gas
Heating Zones:
3
Cooling:
None
Hot Water:
Natural Gas
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Deck - Wood
Fencing:
Other Structures:
Lot Features:
Corner Lot
Road Surface:
Parking & Garage
Total Parking Spaces:
6
Parking Features:
Off Street
Nearby Schools
School District
Brookline School District local
A+
School Safety
2024-25
0.4%
Low
0.3%
Suspensions
0.6%
In-School
0.1%
Emergency
5.1% below state avg
Elementary Schools
10 schools
A+
William H Lincoln School
0.3 mi
|
#20 of 352
|
Score: 61.1
Improved 24 spots from last year
+2.9 above state avg
463 students
Very Diverse
Rising School
Diverse Student Body
Grades K-08
Maimonides School
0.4 mi
Grades K-12
A+
Pierce School
0.7 mi
|
#29 of 352
|
Score: 60.4
Dropped 18 spots from last year
+2.2 above state avg
587 students
Very Diverse
Diverse Student Body
Strong Attendance
Grades K-08
St. Mary of the Assumption School
0.7 mi
Grades PK-08
The Park School
0.9 mi
Grades PK-09
A+
Lawrence School
1.1 mi
|
#9 of 352
|
Score: 64.0
Improved 1 spots from last year
+5.8 above state avg
624 students
Diverse
Diverse Student Body
Strong Attendance
Grades K-08
A
John D Runkle School
1.1 mi
|
#44 of 352
|
Score: 58.2
Dropped 36 spots from last year
+0 above state avg
476 students
Diverse
Diverse Student Body
Grades PK-08
Torah Academy Inc.
1.2 mi
Grades PK-08
A+
Michael Driscoll School
1.2 mi
|
#28 of 352
|
Score: 60.5
Improved 12 spots from last year
+2.3 above state avg
554 students
Diverse
Diverse Student Body
Grades PK-08
A
Roland Hayes School
1.2 mi
|
#40 of 352
|
Score: 58.5
Improved 27 spots from last year
+0.3 above state avg
423 students
Diverse
Rising School
Diverse Student Body
Grades PK-08
High Schools
3 schools
JRI Bay Cove School
1.7 mi
Grades 07-12
Beaver Country Day School
2.2 mi
Grades 06-12
A+
Brookline High School
0.4 mi
|
#2 of 346
|
Score: 82.5
Improved 17 spots from last year
+24.3 above state avg
2,147 students
Diverse
21 sports
• 3,004 athletes
Strong AP Program
High Graduation Rate
College Ready Curriculum
Strong Athletics
Grades 09-12
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Monthly Payment Calculator
Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$1,373
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo
Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
Location
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Neighborhood
86 Chestnut St, Brookline MA 02445
Brookline, MA 02445
Listing Information
Listing Agent
Sarah McIntyre
Listing Office
Red Tree Real Estate
Office Phone
617-487-8015
Agent MLS ID
BB985567
Office MLS ID
AN0907
Listing Data Updated
Sep 6, 2026 3:07 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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