68 Dudley St, Brookline, MA, 02445
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.
Getting Around
Car-Dependent
Some Transit
BikeableSchools
Construction
Condition
- Year built: 1930
Materials
- Foundation: Stone
- Roof: Shingle
- Construction materials: Frame
Type & Style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Gas Water Heater,Oven,Dishwasher,Disposal,Microwave,Range,Refrigerator,Washer,Dryer,Wine Refrigerator
- Laundry features: In Basement
Basement
- Has basement: Yes
- Basement: Full,Partially Finished,Walk-Out Access,Interior Entry,Concrete
Bathroom1
- Features: Bathroom - Half
- Level: First
Bathroom2
- Features: Bathroom - Full
- Level: Basement
Bathroom3
- Level: Second
Bedroom2
- Features: Flooring - Wall to Wall Carpet
- Level: Second
Bedroom3
- Features: Flooring - Wall to Wall Carpet
- Level: Second
Bedroom4
- Features: Flooring - Wall to Wall Carpet
- Level: Third
Bedroom5
- Features: Flooring - Wall to Wall Carpet
- Level: Third
Bedrooms & Bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Dining Room
- Features: Flooring - Hardwood, Window(s) - Picture
- Level: First
Family Room
- Features: Ceiling Fan(s), Flooring - Hardwood
- Level: First
Features
- Bathroom,Study,Foyer,Sauna/Steam/Hot Tub
- Flooring: Tile,Carpet,Hardwood,Flooring - Hardwood
- Number of fireplaces: 4
- Fireplace features: Dining Room,Family Room,Living Room,Master Bedroom
- Fireplace: Yes
- Finished area below ground: 593
- Finished area above ground: 4,641
Heating & Cooling
- Heating features: Forced Air,Heat Pump,Natural Gas
- Cooling features: Central Air
Interior Area
- Total structure area: 5,234
- Total interior livable area: 5,234 sqft
Kitchen
- Features: Flooring - Hardwood, Dining Area, Countertops - Stone/Granite/Solid
- Level: First
Living Room
- Features: Flooring - Hardwood, French Doors
- Level: First
Master Bathroom
- Features: Yes
Master Bedroom
- Features: Flooring - Wall to Wall Carpet
- Level: Second
Property
Details
- Parcel number: 41179
- Zoning: Res
- Exclusions: Included: Treadmill,Elliptical,Weight Bench,Free Weights,Tv In Gym,Porch Furniture,Patio Set
Features
- Private pool: Yes
- Pool features: In Ground
- Patio & porch: Porch,Screened,Deck,Patio
- Exterior features: Porch,Porch - Screened,Deck,Patio,Pool - Inground,Sprinkler System,Garden
- Has view: Yes
- View description: Scenic View(s),Water,Other Water View (See Remarks)
- Has water view: Yes
- Water view: Other (See Remarks),Water
Lot
- Lot size: 0.46 Acres
- Features: Easements
Parking
- Total spaces: 10
- Parking features: Detached,Paved Drive,Shared Driveway,Off Street
- Has garage: Yes
- Attached garage spaces: 2
- Covered spaces: 2
- Has uncovered spaces: Yes
- Uncovered spaces: 8
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Hurricane
- Inland Flooding
- Tsunami
How This Home’s Risks Compare
FEMA Declared Disasters Across Massachusetts Counties
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $20,200 | $242,400 |
| Home Insurance * | $527 | $6,324 |
| Property Taxes | $3,218 | $38,616 |
| Electricity | $1,032 | $12,385 |
| Total | $24,977 | $299,724 |
Income You'd Need if You Spent...
Massachusetts FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-06-18 | Price change | $3,995,000 |
| 2026-05-13 | Listed for sale | $4,650,000 |
| 2007-05-17 | Sold | $2,530,000 |
| 1999-05-17 | Sold | $1,365,000 |
| 1994-06-27 | Sold | $863,000 |
For Sale by Agent
View on Zillow