96 Winterhoff Trl, Brewster, MA 02631
Property image
Property image
OFF MARKET

96 Winterhoff Trl
Brewster, MA 02631

  • 6 Beds
  • 6.5 Baths
  • 7,000 sqft (on 1.10 acres)

$8,447,900

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $47,131/mo*
Refinance Your Home

$8,447,900

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $47,131/mo*
Refinance Your Home
6 Beds
6.5 Baths
7,000 sqft
(on 1.10 acres)

Home Value

Trulia Estimate
$8.45M
Since last month
Decreased$344K (-3.9%)
Since last year
Decreased$159K (-1.8%)
Since last sale
Increased$5M (+144.9%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +202% in the last 10 years
MonthEstimated value
2026
August 2026$8.45M
July 2026$8.79M
June 2026$8.68M
May 2026$8.56M
April 2026$8.37M
March 2026$8.53M
February 2026$8.41M
January 2026$8.03M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
17 Barberry Lane, Brewster, MA
0.28
Single-Family Home
$2,500,000
08/07/26
4
3
2,933
149 Cathedral Road, Brewster, MA
0.46
Single-Family Home
$1,110,000
08/21/26
5
2
2,203
20 Skipjack Way, Brewster, MA
0.50
Single-Family Home
$1,050,000
11/21/25
3
2
1,536
38 Bittersweet Drive, Brewster, MA
0.89
Single-Family Home
$810,000
07/16/26
5
3
2,295
2241 Main Street, Brewster, MA
0.53
Single-Family Home
$700,000
09/30/25
3
2
1,655
2705 Main Street, Brewster, MA
1.02
Single-Family Home
$1,375,000
02/05/26
5
2.5
-
87 N Pond Drive, Brewster, MA
1.39
Single-Family Home
$1,649,000
04/10/26
4
3.5
2,481
126 Bittersweet Drive, Brewster, MA
0.85
Single-Family Home
$850,000
11/14/25
3
2
1,867
231 Yankee Dr, Brewster, MA
0.91
Single-Family Home
$732,000
05/28/26
3
2
2,166
236 Yankee Drive, Brewster, MA
0.90
Single-Family Home
$806,000
10/07/25
3
2
1,713

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
31 Governor Winthrop Road, Brewster, MA 02631
0.11
$2,475,000
3
2.5
2,210
Off Market
9 Gould Drive, Brewster, MA 02631
0.19
$1,802,900
3
2.5
2,075
Off Market
76 Pilgrim Pines Lane, Brewster, MA 02631
0.19
$1,164,000
3
1
864
Off Market
56 Pilgrim Pines Lane, Brewster, MA 02631
0.19
$1,601,000
3
2.5
1,920
Off Market
11 Stuart Street, Brewster, MA 02631
0.20
$1,959,100
5
3
2,325
Off Market
49 Gould Drive, Brewster, MA 02631
0.23
$1,342,100
4
2
1,668
Off Market
257 Crocker Lane, Brewster, MA 02631
0.25
$6,623,900
4
4.5
3,600
Off Market
20 Robinson Road, Brewster, MA 02631
0.23
$1,260,100
3
1
1,264
Off Market
17 Barberry Lane, Brewster, MA 02631
0.28
$2,500,000
4
3
2,933
Recently Sold
0 Crocker Lane, Brewster, MA 02631
0.34
-
-
-
-
Off Market
37 Bates Lane, Brewster, MA 02631
0.39
$2,072,600
4
2.5
2,688
Off Market
149 Cathedral Road, Brewster, MA 02631
0.46
$1,110,000
5
2
2,203
Recently Sold

Local Information

  • Map ViewExplore the area around 96 Winterhoff Trl.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2017
Lot Size
1.1 acres
Living Area
7,000 sqft
Price/Sqft
$1,207
Parking
Garage

About this House

In addition to the Main house at 96 Winterhoff, there is a guest house at 98 Winterhoff. The guest house has 2 bedrooms, 2 full baths and a kitchenette, with a deck overlooking the Bay. The guest house cannot be sold separate from the main house. There is also an outdoor Kitchen and barbecue area and a wood fired pizza oven.
96 Winterhoff Trl, Brewster, MA 02631 is a 6 bedroom, 7 bathroom, 7,000 sqft single-family home built in 2017. It last sold for $3,450,000 on Apr 12, 2016. It is currently off market. The Trulia Estimate is $8,447,900, with a rent estimate of $7,809/month.

Home Details for 96 Winterhoff Trl

Interior Features

Interior Details
BasementNumber of Rooms: 11Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Recreation RoomWet BarCeiling Fan
Heating & Cooling
Heating: Forced Air, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: WoodGardenLawnPatioPorchSprinkler System
Parking & Garage
GarageParking Spaces: 12Parking: Garage Attached

Property Information

Year Built
Year Built: 2017
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.10 acres

Price and Tax history

DateEventPrice
Apr 12, 2016
Source: CCIMLS #21409144
Sold
$3,450,000
Dec 31, 2015
Source: Agent Provided
ListingRemoved
$3,670,000
Oct 21, 2015
Source: Agent Provided
Pending
$3,670,000
May 27, 2015
Source: Agent Provided
PriceChange
$3,670,000
Price decreased by 0%
Jan 23, 2015
Source: Agent Provided
PriceChange
$3,675,000
Price decreased by 1%

Market trends in Brewster

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
48
5MoM

Around this home

What Locals Say about Brewster

At least 52 Trulia users voted on each feature.

  • 93 % Say car is needed

  • 87 % Say parking is easy

  • 87 % Say it's quiet

  • 86 % Say it's dog friendly

  • 83 % Say yards are well-kept

  • 78 % Say people would walk alone at night

  • 76 % Say there's wildlife

  • 66 % Say there's holiday spirit

  • 63 % Say they plan to stay for at least 5 years

  • 57 % Say neighbors are friendly

  • 54 % Say kids play outside

  • 28 % Say there are community events

  • 27 % Say it's walkable to restaurants

  • 24 % Say there are sidewalks

  • 24 % Say streets are well-lit

  • 13 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Rheanna Hastings
    "Lots of families and a beautiful safe place to raise children with lots of outdoor space and things to do."
    0
    Flag
  • Skylar R.
    "Walking your dog and taking them down to the pond for a quick swim is very convenient located right on the bike path which is always a great spot to walk dogs."
    7
    Flag
  • Rheanna H.
    "The beach! Low tide, the stores, the restaurants and the farmers markets. Cape Cod is a one of a kind place. "
    2
    Flag
  • Deboravaughan
    "I really like it!! It is clean, friendly and close to the beach. Houses are well maintained and renters during the summer are great."
    4
    Flag
  • Peloquinbill
    "it is a small quaint neighborhood where everyone is friendly. Neighbors are always visiting and helping each other."
    0
    Flag
  • scarroll32
    "Ideal Cape Cod location For Golfing or swimming in salt water Cape Cod BAY or one of Brewster fresh water ponds Boating fishing "
    0
    Flag
  • Rick S.
    "This is a great town. Rural living, close to all the action of Dennis, Yarmouth and Hyannis. Easy access to the loweer Cape too!. "
    0
    Flag
  • Cathihill
    "Ocean Edge is a great resort community with obtainable membership fees. However, you do not have to be a member to live in a ocean edge. Billington II is the most quiet and least congested of the town home communities at Ocean Edge."
    0
    Flag
  • Teresa M.
    "Beautiful, quiet, peaceful place to live. The schools are excellent and the recreation areas amazing. The association beaches are beautiful and limited to only 11 families. The pool is a joy."
    0
    Flag
  • Nj3167
    "Quite, well manacured properties, very little traffic, quant, old historic Sea Captain's Homes restored into B&B's, Resturants,slower pace of life. Great for Retires."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 96 Winterhoff Trl

  • What is 96 Winterhoff Trl estimated to be worth?
    Trulia's estimated value for 96 Winterhoff Trl in Brewster, MA is $8,447,900.
  • What is the price history for 96 Winterhoff Trl?
    96 Winterhoff Trl in Brewster, MA last sold for $3,450,000 in April 2016.
  • Is Brewster a buyer's or seller's market?
    Brewster is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Brewster?
    Residents describe Brewster, MA as easy to park in, quiet, and dog-friendly. Most residents say you need a car. See recently sold homes in Brewster, MA.
  • Does 96 Winterhoff Trl have air conditioning?
    Yes, 96 Winterhoff Trl in Brewster, MA has air conditioning.
  • Does 96 Winterhoff Trl have laundry facilities?
    Yes, 96 Winterhoff Trl in Brewster, MA has in-unit laundry.

Explore by feature - Air Conditioning

7 rentals with air conditioning in Brewster, MA

Explore by feature - Washer/dryer

9 rentals with a washer/dryer in Brewster, MA

Apartments for Rent

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Off Market Homes Near 96 Winterhoff Trl

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