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Back 242 Sheep Pond Drive
Off Market

242 Sheep Pond Drive

Brewster MA 02631

5
2
5
2599 sq. ft.
23000 sq. ft.
Single-Family
Last sold for $1,250,000
John StringfellowJohn Stringfellow, last sold this property on 25 November 2025 after 75 days on market.

Overview

''The Best View of Sheep Pond.'' That's what the neighbors say—and once you see it, you'll understand why. Tucked down a long, private driveway sits this five-bedroom, two-bath classic, owned by one family for 58 years. The home blends warmth, natural light, and timeless character with a layout designed for generations to enjoy. A cathedral-ceilinged living room, the dining area, and the kitchen overlook the pond. Downstairs, a sprawling walk-out basement offers incredible flexibility, complete with a second fireplace, a spacious den, and a fully functional second kitchen. Outdoors is just as compelling. You've got your own little piece of Sheep Pond with a private beach. The expansive Azek deck and enormous patio are perfect for hosting sunset dinners on the pond, or quiet mornings with coffee and a Brewster Bun. You'll also find a large outdoor shower, mature plantings, a 200-amp electrical panel, a generator, and a charming garden shed. Buyers & agents to confirm all info.

Features

5 bedrooms
2 bathrooms
5 carspaces
5 open car spaces
2599 sq. ft. floor area
23000 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Brewster over the last 12 months, the estimated median property value of 242 Sheep Pond Drive is $1.25m.

Median value
$1.25m
Estimated value range
$700k - $2.11m
Median days on market
57
Estimated value trend
-10%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Brewster. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 242 Sheep Pond Drive

2025
Sold
$1,250,000
25 Nov 2025 by John Stringfellow, of Startpoint Realty

Happy sellers in Brewster

72%
72% of sellers in Brewster reported that their sale price either exceeded or met their price expectations.

Brewster stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 9 reviews in Brewster over the last 12 months.

Local market activity for 5 bedroom single-family properties in Brewster

In the last 12 months, 5 five-bedroom single-family properties similar to 242 Sheep Pond Drive, have been sold.

This represents a 50% decrease in five-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Brewster

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Melanie Cauchon

Sellers who recommend Melanie Cauchon have praised them for being local expert, clear communication, detail-oriented, responsive, supportive, dedicated, and reliable

  •   5   (198 reviews)
  •  5 Reviews in Brewster
  •  4 Sales in Brewster
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Christopher Manning

Sellers who recommend Christopher Manning have praised them for being local expert, responsive, detail-oriented, clear communication, resourceful, great negotiation, and well-prepared

  •   5   (45 reviews)
  •  3 Reviews in Brewster
  •  3 Sales in Brewster
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Tracey Oringer

Tracey Oringer is a recommended agent for Brewster.  They have 7 local sales and collected 1 local review across the last 12 months.

  •   5   (45 reviews)
  •  1 Review in Brewster
  •  7 Sales in Brewster
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Dawn Lee

Dawn Lee is a recommended agent for Brewster.  They have 4 local sales and collected 1 local review across the last 12 months.

  •   5   (5 reviews)
  •  1 Review in Brewster
  •  4 Sales in Brewster
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