20 Wayside Dr, Brewster, MA 02631
OFF MARKET

$807,600

Trulia Estimate
  • Studio

20 Wayside Dr, Brewster, MA 02631

Est. Refi. Payment $4,595/mo*
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Home Value

Trulia Estimate
$808K
Since last month
Decreased$29K (-3.5%)
Since last year
Increased$105K (+15%)
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 +35% in the last 10 years
MonthEstimated value
2026
August 2026$808K
July 2026$837K
June 2026$774K
May 2026$761K
April 2026$880K
March 2026$775K
February 2026$862K
January 2026$733K
2025
2024
2023

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
0.08
Single-Family Home
$651,000
09/16/25
3
2
1,274
81 S Orleans Rd, Brewster, MA
0.10
Single-Family Home
$385,000
07/31/26
3
2
1,586
104 Wayside Drive, Brewster, MA
0.16
Single-Family Home
$810,000
02/02/26
3
2
1,568
36 Tar Kiln Road, Orleans, MA
0.55
Single-Family Home
$937,500
01/05/26
4
2.5
2,356
122 Evelyn's Drive, Brewster, MA
0.55
Single-Family Home
$1,150,000
05/18/26
3
3
2,212
33 Pine Orchard Road, Harwich, MA
0.57
Single-Family Home
$900,000
02/27/26
3
3
2,623
101 Evelyn'S Drive, Brewster, MA
0.58
Single-Family Home
$1,600,000
05/21/26
3
3.5
2,354
16 Crocker Rise, Harwich, MA
0.61
Single-Family Home
$2,575,000
10/31/25
4
3.5
4,840
120 Woodlands Way, Brewster, MA
0.62
Single-Family Home
$3,250,000
02/27/26
-
65,651
30 Pleasant Court, Brewster, MA
0.63
Single-Family Home
$660,000
09/02/25
3
1.5
1,716

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
0.08
$666,900
3
2
1,274
Off Market
90 Grist Mill Road, Brewster, MA 02631
0.10
$663,500
2
1.5
1,104
Off Market
80 Grist Mill Road, Brewster, MA 02631
0.11
$760,800
4
3
1,288
Off Market
193 Wayside Drive, Brewster, MA 02631
0.16
$799,000
3
2
1,764
For Sale
183 Wayside Drive, Brewster, MA 02631
0.17
$687,300
3
2
1,348
Off Market
104 Wayside Drive, Brewster, MA 02631
0.16
$810,000
3
2
1,568
Recently Sold
7 Grist Mill Road, Harwich, MA 02645
0.23
$685,100
4
2
1,624
Off Market
4 Crocker Rise Road, Harwich, MA 02645
0.28
$1,910,800
3
2.5
2,849
Off Market
11 Brothers Ln, Harwich, MA 02645
0.31
$572,700
2
1
825
Off Market
1 Crocker Rise, Harwich, MA 02645
0.31
$1,396,000
3
2.5
2,904
Off Market
9 Connecticut Avenue, Harwich, MA 02645
0.32
$877,700
3
2
1,873
Off Market
14 Crocker Rise, Harwich, MA 02645
0.31
-
4
3.5
2,943
Off Market

Local Information

  • Map ViewExplore the area around 20 Wayside Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home

About this House

This single-family home is located at 20 Wayside Dr, Brewster, MA. 20 Wayside Dr is in Brewster, MA and in ZIP code 02631.
20 Wayside Dr, Brewster, MA 02631 is a studio single-family home. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $807,600, with a rent estimate of $3,673/month.

Home Details for 20 Wayside Dr

Property Information

Property Type / Style
Property Type: Single Family Home

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 20 Wayside Dr

  • What is 20 Wayside Dr estimated to be worth?
    Trulia's estimated value for 20 Wayside Dr in Brewster, MA is $807,600.
  • 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.
  • What are the closest schools to 20 Wayside Dr?
    The closest schools to 20 Wayside Dr in Brewster, MA are Eddy Elementary School (rated 7/10), Nauset Regional High School (rated 6/10), Nauset Regional Middle School (rated 6/10).

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