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68 Dudley Street, Brookline MA 02445

Brookline, MA 02445 • Reservoir
$4,650,000
$3,995,000
Est. $23,979/month
5
Beds
4.5
Baths
5,234
Sq Ft
$763
Price/Sq Ft
0.46
Acres
1930
Year Built
2
Garage Spaces
58
Days on Market
Active Price Drop -$655,000 Listed May 12, 2026 • MLS# 73517349 Copied! • Updated Jun 21, 2026

About this home

Handsomely poised overlooking the Brookline Reservoir and nestled back from the street, this distinguished period home offers four finished levels and serene water views on nearly a half-acre with bluestone patio and pool. The gracious entry opens into a grand foyer flanked by sun-drenched rooms. Bay windows in the living room, dining room, family room, and primary suite frame reservoir and garden views. Four fireplaces, high ceilings, crown molding, and custom woodwork throughout. Well-equipped kitchen for serious cooks with breakfast area and counter seating. Private first-floor study. Enchanting screened porch access the dining and living rooms for al fresco dining. Second floor: three bedrooms, two baths, and a primary suite with large dressing room, ensuite bath, and private deck. Third floor: two additional bedrooms and full bath. Lower level: exercise room, sauna, wine cellar and lav. Two-car garage. Minutes from Chestnut Hill shopping, Longwood Medical Area, and universities.

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Recently Sold Nearby

Property History

Market Insights

1
Price Changes
14.1%
Price Range

Property Timeline

Price Reduced
Jun 18, 2026
$3,995,000 $655,000 (-14.09%)
From $4,650,000 to $3,995,000 (-14.1%)
🏠
Listed for Sale
May 13, 2026
$4,650,000
Original listing
Agent: Friedler / Marchant Living Group Office: Hammond Residential Real Estate

Tax History

Year Taxes Assessment
2026 $42,943 $4,507,500

Financial Details

Annual Property Tax
$42,943
Tax Year 2026
Assessed Value
$4,507,500

Facts & Features

2 Car Garage
Central AC

Home Facts

Type Residential
Style Single Family Residence
Year Built 1930
Living Area 5,234 sq ft
Lot Size 0.46 acres
Bedrooms 5
Full Baths 4
Half Baths 1
Total Rooms 11

Interior

Heating Forced Air, Heat Pump, Natural Gas
Cooling Central Air
Flooring Tile, Carpet, Hardwood, Flooring - Hardwood
Appliances Gas Water Heater, Oven, Dishwasher, Disposal, Microwave, Range, Refrigerator, Washer, Dryer, Wine Refrigerator
Fireplace Dining Room, Family Room, Living Room, Master Bedroom
Fireplaces 4
Basement Full, Partially Finished, Walk-out Access, Interior Entry, Concrete
Laundry In Basement
Features Bathroom, Study, Foyer, Sauna/steam/hot Tub

Exterior

Construction Frame
Architecture Colonial
Roof Shingle
Features Porch, Porch - Screened, Deck, Patio, Pool - Inground, Sprinkler System, Garden
Pool In Ground
Spa None
Fencing None
Patio/Porch Porch, Screened, Deck, Patio
Garage Spaces 2
Has Garage Yes
Features Detached, Paved Drive, Shared Driveway, Off Street
Total Spaces 10
Electric Circuit Breakers
Water Public
Sewer Public Sewer
Gas None
Other For Gas Range, For Electric Oven
Annual Tax $42,943
Assessed Value $4,507,500
Fee Includes None
Amenities None
Optional Fee Includes None
Seller Disclosures Seller Makes No Representations About Speaker System, Fireplaces, Basement Electric Heat. One Window In Primary Covered By Built-in.. Range Vent Not Operational
Exclusions Included: Treadmill, Elliptical, Weight Bench, Free Weights, Tv In Gym, Porch Furniture, Patio Set
Possession None
Accepted Financing None
Structure Type []
House Color gray
Sq Ft Source Public Record
Documents None
County Norfolk
Total market time (incl. prior listings) 40 days

Property Overview

Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1930
Bedrooms
5
Full Bathrooms
4
Half Bathrooms
1
Living Area
5,234 sq ft
Total Rooms
11

Room Details

First Floor

Bathroom1
Bathroom - Half
Dining Room
Flooring - Hardwood, Window(s) - Picture
Kitchen
Flooring - Hardwood, Dining Area, Countertops - Stone/Granite/Solid
Living Room
Flooring - Hardwood, French Doors
Family Room
Ceiling Fan(s), Flooring - Hardwood

Second Floor

Bedroom3
Flooring - Wall to Wall Carpet
Bedroom2
Flooring - Wall to Wall Carpet
Bathroom3
Master Bedroom
Flooring - Wall to Wall Carpet

Third Floor

Bedroom5
Flooring - Wall to Wall Carpet
Bedroom4
Flooring - Wall to Wall Carpet

Basement Floor

Bathroom2
Bathroom - Full

Other Floor

Office
Master Bathroom
Yes

Interior Features

Flooring: Tile, Carpet, Hardwood, Flooring - Hardwood
Appliances: Gas Water Heater, Oven, Dishwasher, Disposal, Microwave, Range, Refrigerator, Washer, Dryer, Wine Refrigerator
Interior Features: Bathroom, Study, Foyer, Sauna/Steam/Hot Tub
Windows:
Basement: Full, Partially Finished, Walk-Out Access, Interior Entry, Concrete
Laundry: In Basement
Security: Security System

Construction & Materials

Style: Colonial
Year Built: 1930
Structure Type:
Exterior Materials: Frame
Roof: Shingle
Foundation: Stone

Heating, Cooling & Utilities

Heating: Forced Air, Heat Pump, Natural Gas
Heating Zones: 4
Cooling: Central Air
Cooling Zones: 4
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features: Porch, Porch - Screened, Deck, Patio, Pool - Inground, Sprinkler System, Garden
Patio & Porch: Porch, Screened, Deck, Patio
Fencing:
Other Structures:
Lot Features: Easements
Road Surface:

Parking & Garage

Garage Spaces: 2
Total Parking Spaces: 10
Parking Features: Detached, Paved Drive, Shared Driveway, Off Street

Special Features

Fireplaces: 4
Fireplace Type: Dining Room, Family Room, Living Room, Master Bedroom
Pool: Private Pool
Pool Features: In Ground
View: Yes
View Type: Scenic View(s)
Community Amenities: Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship
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
E

Elementary Schools

10 schools
Maimonides School
0.4 mi
Grades K-12
A+
William H Lincoln School
0.4 mi | #19 of 352 | Score: 61.4
Improved 25 spots from last year
+3.2 above state avg
494 students Very Diverse
Rising School Diverse Student Body
Grades K-08
The Park School
0.7 mi
Grades PK-09
A
Roland Hayes School
0.7 mi | #39 of 352 | Score: 58.5
Improved 28 spots from last year
+0.3 above state avg
418 students Diverse
Rising School Diverse Student Body
Grades PK-08
A
John D Runkle School
0.7 mi | #44 of 352 | Score: 58.0
Dropped 36 spots from last year
-0.2 below state avg
476 students Diverse
Diverse Student Body
Grades PK-08
Torah Academy Inc.
0.9 mi
Grades PK-08
A+
Pierce School
1.0 mi | #27 of 352 | Score: 60.5
Dropped 16 spots from last year
+2.3 above state avg
592 students Very Diverse
Diverse Student Body
Grades K-08
A+
Michael Driscoll School
1.0 mi | #30 of 352 | Score: 60.1
Improved 10 spots from last year
+1.9 above state avg
567 students Diverse
Diverse Student Body
Grades PK-08
St. Mary of the Assumption School
1.1 mi
Grades PK-08
Dexter Southfield, Inc.
1.3 mi
Grades PK-12
H

High Schools

3 schools
Beaver Country Day School
1.6 mi
Grades 06-12
JRI Bay Cove School
1.7 mi
Grades 07-12
A+
Brookline High School
0.6 mi | #1 of 346 | Score: 82.5
Improved 18 spots from last year
+24.3 above state avg
2,181 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 Breakdown

Principal & Interest $0
Property Tax $3,579
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

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Payment Over Time

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Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
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Location

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Neighborhood

Reservoir

68 Dudley Street, Brookline MA 02445

Brookline, MA 02445

Listing Information

Listing Agent Friedler / Marchant Living Group
Listing Office Hammond Residential Real Estate
Office Phone 617-731-4644
Agent MLS ID TM361270
Office MLS ID AN3108
Listing Data Updated Jun 21, 2026 4:05 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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