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Active

68 Dudley Street

Brookline, MA 02445

$3,995,000
5Bedrooms
5Bathrooms
5,234Square feet
1930Year built

Residential · Active · MLS #73517349
Listing Courtesy of Hammond Residential Real Estate | Friedler & Marchant Living Group

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MLS PIN data

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.

Property information

Details at a glance

Interior

Rooms
11
Heating
Forced Air, Heat Pump, Natural Gas
Cooling
Central Air
Flooring
Tile, Carpet, Hardwood, Flooring - Hardwood
Fireplaces
4

Building

Style
Single Family Residence
Year built
1930
Garage
2
Parking
10
Foundation
Stone
Roof
Shingle

Land & utilities

Lot size
0.46 acres
Water
Public
Sewer
Public Sewer
Zoning
Res

Financial

Annual taxes
$42,943
Assessment year
2026

Listing history

Price and status timeline

No additional public listing history was supplied for this property.

Property value estimate

An informed starting point

Estimated value$4,736,436

Estimated range $4,201,565$5,271,306

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Automated estimates are not appraisals or guarantees of market value.

Comparable sales

Recent properties for context

Recent comparable sales are not available for this property.

Photo insights

Condition signals

Overall presentationabove average

Generated from listing photography; not a substitute for an inspection.

Local market context

How this home compares in Brookline

MetricThis propertyBrookline
List price$3,995,000$1,497,000167% above local
Price / sq ft$763$92918% below local
Days on market405629% below local
Explore homes in Brookline

Active city listing statistics from MLS PIN as of September 6, 2026. Asking prices are not completed-sale values.

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Common questions

About 68 Dudley Street

Can I schedule a private showing?

Yes. Request a tour of 68 Dudley Street and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.