58 Wayside Dr, Brewster, MA 02631
Property image
Property image
OFF MARKET

58 Wayside Dr
Brewster, MA 02631

  • 3 Beds
  • 2.5 Baths
  • 1,596 sqft (on 0.47 acres)

$807,800

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $4,575/mo*
Refinance Your Home

$807,800

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $4,575/mo*
Refinance Your Home
3 Beds
2.5 Baths
1,596 sqft
(on 0.47 acres)

Home Value

Trulia Estimate
$808K
Since last month
Decreased$3K (-0.4%)
Since last year
Increased$28K (+3.6%)
Since last sale
Increased$208K (+34.7%)
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 +112% in the last 10 years
MonthEstimated value
2026
August 2026$808K
July 2026$811K
June 2026$813K
May 2026$805K
April 2026$799K
March 2026$799K
February 2026$777K
January 2026$769K
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
55 Wayside Drive, Brewster, MA
0.04
Single-Family Home
$651,000
09/16/25
3
2
1,274
104 Wayside Drive, Brewster, MA
0.10
Single-Family Home
$810,000
02/02/26
3
2
1,568
81 S Orleans Rd, Brewster, MA
0.17
Single-Family Home
$385,000
07/31/26
3
2
1,586
33 Pine Orchard Road, Harwich, MA
0.54
Single-Family Home
$900,000
02/27/26
3
3
2,623
30 Pleasant Court, Brewster, MA
0.71
Single-Family Home
$660,000
09/02/25
3
1.5
1,716
122 Evelyn's Drive, Brewster, MA
0.63
Single-Family Home
$1,150,000
05/18/26
3
3
2,212
36 Tar Kiln Road, Orleans, MA
0.61
Single-Family Home
$937,500
01/05/26
4
2.5
2,356
Pine Grove Rd, Brewster, MA
0.96
Single-Family Home
$710,000
12/05/25
2
2
1,560
101 Evelyn'S Drive, Brewster, MA
0.66
Single-Family Home
$1,600,000
05/21/26
3
3.5
2,354
171 Timberlane Drive, Brewster, MA
1.02
Single-Family Home
$655,000
11/21/25
3
2
1,188

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
55 Wayside Drive, Brewster, MA 02631
0.04
$652,500
3
2
1,274
Off Market
104 Wayside Drive, Brewster, MA 02631
0.10
$810,000
3
2
1,568
Recently Sold
118 Wayside Drive, Brewster, MA 02631
0.12
$915,000
3
2.5
1,440
For Sale
193 Wayside Drive, Brewster, MA 02631
0.14
$799,000
3
2
1,764
For Sale
183 Wayside Drive, Brewster, MA 02631
0.15
$699,400
3
2
1,348
Off Market
90 Grist Mill Road, Brewster, MA 02631
0.16
$681,600
2
1.5
1,104
Off Market
80 Grist Mill Road, Brewster, MA 02631
0.16
$790,600
4
3
1,288
Off Market
4 Crocker Rise Road, Harwich, MA 02645
0.23
$1,893,800
3
2.5
2,849
Off Market
14 Crocker Rise, Harwich, MA 02645
0.26
-
4
3.5
2,943
Off Market
1 Crocker Rise, Harwich, MA 02645
0.26
$1,409,900
3
2.5
2,904
Off Market
7 Grist Mill Road, Harwich, MA 02645
0.25
$679,300
4
2
1,624
Off Market
6 Wilmas Way, Harwich, MA 02645
0.33
$776,300
3
2
1,102
Off Market

Local Information

  • Map ViewExplore the area around 58 Wayside Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1994
Lot Size
0.47 acres
Living Area
1,596 sqft
Price/Sqft
$506

About this House

This custom built one owner home offers wonderful livability in the beautiful town of Brewster! You'll find gorgeous wide pine floors in the open dining / family area and formal living room. The kitchen is highlighted by the warmth of the wooden cabinetry. Set back nicely from the road, this property enjoys a low maintenance natural ''Cape Cod'' landscape and stone driveway. Some coveted features include a newer roof, Azek trim, a wood burning fireplace, first floor primary en suite bedroom, whole house attic fan, full basement, and a walk in attic for additional storage. Come to Wayside Drive and live the good life!
58 Wayside Dr, Brewster, MA 02631 is a 3 bedroom, 3 bathroom, 1,596 sqft single-family home built in 1994. It last sold for $600,000 on Oct 12, 2021. It is currently off market. The Trulia Estimate is $807,800, with a rent estimate of $3,923/month.

Home Details for 58 Wayside Dr

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1994Year Updated: 1997
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.47 acres

Price and Tax history

DateEventPrice
Oct 12, 2021
Source: CCIMLS #22105398
Sold
$600,000
Sep 10, 2021
Source: CCIMLS #22105398
Pending
$475,000

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 58 Wayside Dr

  • What is 58 Wayside Dr estimated to be worth?
    Trulia's estimated value for 58 Wayside Dr in Brewster, MA is $807,800.
  • What is the price history for 58 Wayside Dr?
    58 Wayside Dr in Brewster, MA last sold for $600,000 in October 2021.
  • 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 58 Wayside Dr?
    The lot at 58 Wayside Dr in Brewster, MA is about 0.47 acres (20,473 sq ft).

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