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

$2,853,600

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 3,229 sqft (on 0.53 acres)

88 Winterhoff Trl, Brewster, MA 02631

Est. Refi. Payment $16,061/mo*
Refinance Your Home
Currently Off Market - Sold Oct 31, 2011 for $895,000

Home Value

Trulia Estimate
$2.85M
Since last month
Decreased$65K (-2.2%)
Since last year
Increased$82K (+2.9%)
Since last sale
Increased$2M (+218.6%)
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 +123% in the last 10 years
MonthEstimated value
2026
August 2026$2.85M
July 2026$2.92M
June 2026$2.9M
May 2026$2.89M
April 2026$2.82M
March 2026$2.83M
February 2026$2.75M
January 2026$2.7M
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
0.42
Single-Family Home
$1,110,000
08/21/26
5
2
2,203
20 Skipjack Way, Brewster, MA
0.46
Single-Family Home
$1,050,000
11/21/25
3
2
1,536
2241 Main Street, Brewster, MA
0.49
Single-Family Home
$700,000
09/30/25
3
2
1,655
38 Bittersweet Drive, Brewster, MA
0.86
Single-Family Home
$810,000
07/16/26
5
3
2,295
126 Bittersweet Drive, Brewster, MA
0.83
Single-Family Home
$850,000
11/14/25
3
2
1,867
231 Yankee Dr, Brewster, MA
0.88
Single-Family Home
$732,000
05/28/26
3
2
2,166
236 Yankee Drive, Brewster, MA
0.87
Single-Family Home
$806,000
10/07/25
3
2
1,713
142 Yankee Drive, Brewster, MA
1.04
Single-Family Home
$775,000
05/15/26
3
2
1,638
398 Lund Farm Way, Brewster, MA
1.46
Single-Family Home
$1,015,000
05/19/26
4
3
2,448

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
0.10
$2,463,400
3
2.5
2,210
Off Market
11 Stuart Street, Brewster, MA 02631
0.16
$2,006,300
5
3
2,325
Off Market
76 Pilgrim Pines Lane, Brewster, MA 02631
0.15
$1,163,200
3
1
864
Off Market
56 Pilgrim Pines Lane, Brewster, MA 02631
0.16
$1,557,600
3
2.5
1,920
Off Market
9 Gould Drive, Brewster, MA 02631
0.16
$1,788,800
3
2.5
2,075
Off Market
20 Robinson Road, Brewster, MA 02631
0.20
$1,281,800
3
1
1,264
Off Market
49 Gould Drive, Brewster, MA 02631
0.21
$1,326,900
4
2
1,668
Off Market
257 Crocker Lane, Brewster, MA 02631
0.25
$6,623,900
4
4.5
3,600
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
0.37
$2,072,600
4
2.5
2,688
Off Market
149 Cathedral Road, Brewster, MA 02631
0.42
$1,110,000
5
2
2,203
Recently Sold

Local Information

  • Map ViewExplore the area around 88 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
1960
Lot Size
0.53 acres
Living Area
3,229 sqft
Price/Sqft
$884
Parking
Garage

About this House

Brewster at its finest! Less than one tenth of a mile to Deeded beach rights to the private Sunset Beach Association Beach on Cape Cod Bay! AND a mooring permit may be possible as there is no wait list! Classic 4 bedroom, 3 bath Cape Cod home. Enter the skylit foyer from the private stone patio, and you will find the large, family kitchen complete with island, adjacent breezeway, and direct entry from the 2 car garage. The gracious fireplaced living room with hardwood floors, and built-ins flows nicely to the dining room. The First Floor also offers the Master Bedroom with private bath, office, laundry and covered deck. On the second floor you will find 2 additional bedrooms and a family room which could convert nicely to a private Master Bedroom suite with its own deck. Lovely grounds... Intown location. This is a rare offering.
88 Winterhoff Trl, Brewster, MA 02631 is a 4 bedroom, 3 bathroom, 3,229 sqft single-family home built in 1960. It last sold for $895,000 on Oct 31, 2011. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,853,600, with a rent estimate of $4,568/month.

Home Details for 88 Winterhoff Trl

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1960Year Updated: 1971
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.53 acres

Price and Tax history

DateEventPrice
Oct 31, 2011
Source: CCIMLS #21105670
Sold
$895,000
Sep 9, 2011
Source: Agent Provided
PriceChange
$985,000
Price decreased by 12%
Aug 30, 2011
Source: Agent Provided
PriceChange
$1,125,000
Price increased by 14%
Aug 13, 2011
Source: Agent Provided
PriceChange
$985,000
Price decreased by 6%
Aug 4, 2011
Source: Agent Provided
PriceChange
$1,050,000
Price decreased by 7%

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 88 Winterhoff Trl

  • What is 88 Winterhoff Trl estimated to be worth?
    Trulia's estimated value for 88 Winterhoff Trl in Brewster, MA is $2,853,600.
  • What is the price history for 88 Winterhoff Trl?
    88 Winterhoff Trl in Brewster, MA last sold for $895,000 in October 2011.
  • 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.
  • How big is the lot at 88 Winterhoff Trl?
    The lot at 88 Winterhoff Trl in Brewster, MA is about 0.53 acres (23,210 sq ft).
  • Does 88 Winterhoff Trl have a garage?
    Yes, 88 Winterhoff Trl in Brewster, MA has a garage.

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