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A rare find in Brookline, this property offers privacy and tranquility on a secluded lot adjacent to Sargent Estates. Spanning three finished levels plus a lower level, the home features 6 bedrooms and 6 full and 2 half baths, with meticulous craftsmanship and striking architectural details throughout. A grand rotunda entry leads to a chef’s kitchen, expansive living and dining rooms, family room, and mudroom. The second floor includes three bedroom suites, each with its own bath, plus two office spaces. The third floor offers two additional bedroom suites, while the lower level includes a sixth suite, gym, large family room, and laundry. Surrounded by mature landscaping and set well back from the street, the property boasts a pool, hot tub, sauna, outdoor fireplace, pizza oven, and full outdoor kitchen—an exceptional setting for both relaxation and entertaining. Not to be missed!

Highlights

  • Residential
  • Single Family Residence
  • Built in 2006
  • 0.57 Acre Lot
  • 3 Car Garage
  • 236 days on Market

  • Bedrooms
    6
  • Bathrooms
    6 full · 2 half
  • Year Built
    2006
  • Architectural Style
    Colonial, Shingle
  • Construction Materials
    Frame
  • Foundation
    Concrete Perimeter
  • Garage Spaces
    3.0
  • Parking Features
    Attached, Paved, Garage Door Opener, Garage, Off Street, Heated Garage
  • Living Area
    7780.0
  • Interior Features
    Wet Bar, Central Vacuum, Wired for Sound
  • Appliances
    Dryer, Dishwasher, Microwave, Refrigerator, Washer, Range, Disposal, Oven, Freezer, Plumbed For Ice Maker, Range Hood, Water Softener, Gas Water Heater, Water Heater, Wine Refrigerator
  • Flooring
    Wood
  • Exterior Features
    Lighting, Balcony, Gas Grill, Rain Gutters, Outdoor Grill
  • Patio And Porch
    Covered, Patio, Deck, Porch
  • Pool Features
    Heated, In Ground, Private
  • Security Features
    Security System
  • Cooling
    Central Air, Zoned
  • Heating
    Forced Air, Natural Gas, Zoned, Radiant, Humidity Control
  • Basement
    Finished, Full, Walk-Out Access

  • Acres
    0.57
  • Lot Features
    Wooded, Level, Landscaped
  • Water
    Public

  • County
    Norfolk
  • City
    Brookline
  • Zip Code
    02445
  • High School
    Brookline Hs
  • Middle School
    Lincoln
  • Elementary School
    Lincoln

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Frequently Asked Questions

How do I schedule a tour of 1 Chestnut Pl?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 1 Chestnut Pl.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 1 Chestnut Pl?

Click Ask a Question to talk with our team. You already know it is a 6 bed, 6 bath, listed for $7,500,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Brookline, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 1 Chestnut Pl?

With a 20% down payment and a 30-year fixed loan at an illustrative 6.75% rate, the ez Mortgage Calculator estimates the monthly payment for 1 Chestnut Pl at around $46,292. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 1 Chestnut Pl?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Norfolk County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 1 Chestnut Pl?

In most cases, yes. Whether 1 Chestnut Pl is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Brookline's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 1 Chestnut Pl?

We can handle that for you. Our preferred local agent specializes in residentials in Brookline and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $7,500,000 with 7,780 sqft of space—that comes out to approximately $964 per square foot.

How long has this property been on the market?

1 Chestnut Pl was listed on March 17, 2026, which means it's been on the market for 236 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 2006, making it approximately 20 years old.

What is the lot size of this property?

1 Chestnut Pl sits on a 0.57-acre lot, which is 24,829 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Lincoln
  • Middle: Lincoln
  • High: Brookline Hs

Want to see how these schools compare? Check out our Norfolk County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for 1 Chestnut Pl?

The most recent public record shows annual property taxes for 1 Chestnut Pl were approximately $67,511. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 1 Chestnut Pl still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, MLS Property Information Network (MLS PIN). All rights reserved.

Last Updated: November 08, 2026 at 03:46AM | Source: MLS Property Information Network (MLS PIN) | MLS#: 73487838