Is a car needed in Brewster, MA?

As of early 2026, 93% of users say car is needed

Is parking easy in Brewster, MA?

As of early 2026, 87% of users say parking is easy

Is Brewster, MA quiet?

As of early 2026, 87% of users say it's quiet

Is Brewster, MA dog-friendly?

As of early 2026, 86% of users say it's dog friendly

Are yards well-kept in Brewster, MA?

As of early 2026, 83% of users say yards are well-kept

Would people walk alone at night in Brewster, MA?

As of early 2026, 78% of users say people would walk alone at night

Is there wildlife in Brewster, MA?

As of early 2026, 76% of users say there's wildlife

Does Brewster, MA show holiday spirit?

As of early 2026, 66% of users say there's holiday spirit

Do residents of Brewster, MA plan to stay at least 5 years?

As of early 2026, 63% of users say they plan to stay for at least 5 years

Are neighbors friendly in Brewster, MA?

As of early 2026, 57% of users say neighbors are friendly

Do kids play outside in Brewster, MA?

As of early 2026, 54% of users say kids play outside

Are there community events in Brewster, MA?

As of early 2026, 28% of users say there are community events

Is Brewster, MA walkable to restaurants?

As of early 2026, 27% of users say it's walkable to restaurants

Does Brewster, MA have sidewalks?

As of early 2026, 24% of users say there are sidewalks

Are the streets well-lit in Brewster, MA?

As of early 2026, 24% of users say streets are well-lit

Is Brewster, MA walkable to grocery stores?

As of early 2026, 13% of users say it's walkable to grocery stores

What is 183 Wayside Drive estimated to be worth?

Trulia's estimated value for 183 Wayside Drive in Brewster, MA is $695,000 .

What is the price history for 183 Wayside Drive?

183 Wayside Drive in Brewster, MA last sold for $372,500 in September 2019.

Is Brewster a buyer's or seller's market?

Brewster is currently a seller's market, based on recent for-sale activity.

What's the median sale price in Brewster?

The median sale price in Brewster is $618K. That is down $73.33K from the prior month.

Does 183 Wayside Drive have air conditioning?

Yes, 183 Wayside Drive in Brewster, MA has air conditioning.

Does 183 Wayside Drive have laundry facilities?

Yes, 183 Wayside Drive in Brewster, MA has laundry facilities.

OFF MARKET

$695,000

Trulia Estimate

3 Beds
2 Baths
1,348 sqft (on 0.34 acres)

183 Wayside Drive, Brewster, MA 02631

Est. Refi. Payment $4,135/mo*

Refinance Your Home

Currently Off Market - Sold Sep 19, 2019 for $372,500

Home Value

Trulia Estimate

$695K

Since last month

$2K (-0.2%)

Since last year

$49K (+7.7%)

Since last sale

$316K (+84.8%)

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 +10% in the last 10 years

Month	Estimated value
2026
September 2026	$688K
August 2026	$690K
July 2026	$694K
June 2026	$704K
May 2026	$690K
April 2026	$695K
March 2026	$685K
February 2026	$679K
January 2026	$639K
2025
December 2025	$633K
November 2025	$634K
October 2025	$644K
September 2025	$639K
August 2025	$645K
July 2025	$657K
June 2025	$651K
May 2025	$657K
April 2025	$644K
March 2025	$643K
February 2025	$619K
January 2025	$624K

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
104 Wayside Drive, Brewster, MA	0.08	Single-Family Home	$810,000	02/02/26	3	2	1,568
3 Connecticut Avenue, Harwich, MA	0.31	Single-Family Home	$530,000	09/10/26	2	1	768
33 Pine Orchard Road, Harwich, MA	0.41	Single-Family Home	$900,000	02/27/26	3	3	2,623
9 Captain Phillips Rd, Harwich, MA	0.97	Single-Family Home	$589,030	08/26/26	3	2	1,288
13 Elm Drive, Harwich, MA	0.93	Single-Family Home	$725,000	10/22/25	4	2	1,612
171 Timberlane Drive, Brewster, MA	1.15	Single-Family Home	$655,000	11/21/25	3	2	1,188
122 Evelyn's Drive, Brewster, MA	0.66	Single-Family Home	$1,150,000	05/18/26	3	3	2,212
527 S Orleans Road, Brewster, MA	1.08	Single-Family Home	$590,000	06/28/26	2	1.5	996
12 Maple Lane, Harwich, MA	1.02	Single-Family Home	$825,000	06/30/26	4	2	2,060

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
193 Wayside Drive, Brewster, MA 02631	0.01	$775,000	3	2	1,764	For Sale
0 Grist Mill Pond, Brewster, MA 02631	0.09	-	-	-	-	Off Market
118 Wayside Drive, Brewster, MA 02631	0.08	$804,700	3	2.5	1,440	Off Market
104 Wayside Drive, Brewster, MA 02631	0.08	$810,000	3	2	1,568	Recently Sold
7 Grist Mill Road, Harwich, MA 02645	0.14	$708,600	4	2	1,624	Off Market
1 Crocker Rise, Harwich, MA 02645	0.13	$1,412,900	3	2.5	2,904	Off Market
55 Wayside Drive, Brewster, MA 02631	0.10	$669,600	3	2	1,274	Off Market
4 Crocker Rise Road, Harwich, MA 02645	0.13	$1,932,400	3	2.5	2,849	Off Market
80 Grist Mill Road, Brewster, MA 02631	0.15	$845,000	4	3	1,288	Off Market
6 Wilmas Way, Harwich, MA 02645	0.18	$715,300	3	2	1,102	Off Market
90 Grist Mill Road, Brewster, MA 02631	0.16	$638,600	2	1.5	1,104	Off Market

Local Information

Map ViewExplore the area around 183 Wayside Drive.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1965

0.34 acre lot

1,348 sqft

$516/sqft

Garage

About this House

Back on the market- Lucky for you! Lovingly maintained ranch with wonderful features including Central Air, a Generator, 2 Fireplaces, Pine Flooring, finished basement family room, a large Screened Porch and low-maintenance yard! A wonderful home for entertaining or family gatherings, you'll enjoy the spacious living room w/ built-ins and fireplace, as well as the huge kitchen/dining area which opens onto the screened porch and garden beyond for summertime fun. 3 bedrooms and 2 full baths complete the first floor. On the lower level, you'll find the garage, a finished family room with a 2nd fireplace, a 2nd finished room+ lots of unfinished space for storage! Great neighborhood. This home is in the Nauset School District.

183 Wayside Drive, Brewster, MA 02631 is a 3 bedroom, 2 bathroom, 1,348 sqft single-family home built in 1965. It last sold for $372,500 on Sep 19, 2019 (1% below the $374,900 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $695,000, with a rent estimate of $3,422/month.

Last check for updates: about 7 hours ago

Listed by Susan Baker, (508) 237-1730

Gibson Sotheby's International Realty

Bought with: Robert R Tucker, (508) 341-7809, Kinlin Grover Real Estate

Source: CCIMLS, MLS#21905282

Home Details for 183 Wayside Drive

Interior Features
Interior Details Basement: FinishedNumber of Rooms: 5
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Appliances & Utilities Appliances: Washer, OtherLaundry: Electric Dryer HookupWasher
Heating & Cooling Has CoolingAir Conditioning: Central Air
Fireplace & Spa Number of Fireplaces: 2
Windows, Doors, Floors & Walls Flooring: Vinyl, Wood
Levels, Entrance, & Accessibility Stories: 1Floors: Vinyl, Wood

Exterior Features
Exterior Home Features Roof: Asphalt ShinglePatio / Porch: Screened PorchExterior: Garden, Underground Sprinkler SystemGarden
Parking & Garage Number of Garage Spaces: 1Has a GarageNo Attached GarageHas Open ParkingParking Spaces: 3Parking: Driveway
Frontage Not on Waterfront

Days on Market
Cumulative Days on Market: 40

Property Information
Year Built Year Built: 1965
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence
Building Construction Materials: Clapboard, OtherDoes Not Include Home Warranty
Property Information Parcel Number: 12940

Price & Status
Price List Price: $374,900

Active Status
MLS Status: Closed

Location
Direction & Address City: BrewsterCommunity: Meetinghouse Village

Building
Building Area Building Area: 1348 Square Feet

HOA
HOA Fee Includes: Common AreaHas an HOA

Lot Information
Lot Area: 0.34 acres

Listing Info
Special Conditions: None

Miscellaneous
BasementMls Number: 21905282Showing Requirements: Appointment Required

Price and Tax history

Date	Event	Price
Sep 19, 2019 Source: CCIMLS #21905282	Sold	$372,500
Dec 15, 2015 Source: CCIMLS #21507008	Sold	$315,000

Additional Cost

Market trends in Brewster

Last updated August 2026

Avg. sale price

$618K

$73.33KMoM

Sale-to-List Price

—

Price per sq ft

$487

$17MoM

Available listings

7MoM

Around this home

Stony Brook Elementary School
PK-2
Public
220 Students
Brewster School District
NA
GreatSchools Rating
Parent Rating Average
Excellent support for our child with special needs, strong family and community engagement. Very welcoming environment and caring for their students.
Parent Review
8y ago
3 Reviews

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
Resident
8mo ago
"Lots of families and a beautiful safe place to raise children with lots of outdoor space and things to do."
0
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Skylar R.
Resident
5y ago
"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.
Visitor
6y ago
"The beach! Low tide, the stores, the restaurants and the farmers markets. Cape Cod is a one of a kind place. "
2
Flag
Deboravaughan
Visitor
7y ago
"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
Resident
8y ago
"it is a small quaint neighborhood where everyone is friendly. Neighbors are always visiting and helping each other."
0
Flag
scarroll32
11y ago
"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.
12y ago
"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
13y ago
"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.
13y ago
"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
15y ago
"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

All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than CC&I Assoc. of REALTORS®, Inc. includes the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS®, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. This site was last updated 2026-09-19 11:33:07 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2026© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

Frequently asked questions about 183 Wayside Drive

What is 183 Wayside Drive estimated to be worth?
Trulia's estimated value for 183 Wayside Drive in Brewster, MA is $695,000.
What is the price history for 183 Wayside Drive?
183 Wayside Drive in Brewster, MA last sold for $372,500 in September 2019.
Is Brewster a buyer's or seller's market?
Brewster is currently a seller's market, based on recent for-sale activity.
What's the median sale price in Brewster?
The median sale price in Brewster is $618K. That is down $73.33K from the prior month.
Does 183 Wayside Drive have air conditioning?
Yes, 183 Wayside Drive in Brewster, MA has air conditioning.
Does 183 Wayside Drive have laundry facilities?
Yes, 183 Wayside Drive in Brewster, MA has laundry facilities.

Explore by feature - Air Conditioning

8 rentals with air conditioning in Brewster, MA

FURNISHED
$2,200/mo
Total price
2 bd
2.5 ba
1,380 sqft
30 Crescent Ln,
Brewster, MA 02631
APPLY INSTANTLY
FURNISHED
$3,000/mo
Total price
2 bd
2 ba
950 sqft
53 Chilton Ln,
Brewster, MA 02631
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$2,300/mo
Total price
2 bd
1 ba
600 sqft
133 Millstone Rd,
Brewster, MA 02631
APPLY INSTANTLY
FURNISHED
$2,000/mo
Total price
2 bd
2 ba
935 sqft
218 Eaton Ln,
Brewster, MA 02631
APPLY INSTANTLY
$1,850/mo
Total price
1 bd
1.5 ba
1,380 sqft
35 Chestnut Cir,
Brewster, MA 02631
APPLY INSTANTLY
$1,275/mo
Total price
1 ba
200 sqft
2100 Main St #5,
Brewster, MA 02631
APPLY INSTANTLY
FURNISHED
$3,500/mo
Total price
3 bd
2.5 ba
1,144 sqft
5 Commons Way,
Brewster, MA 02631
PET FRIENDLY
FURNISHED
$4,000/mo
Total price
3 bd
3 ba
1,783 sqft
549 S Orleans Rd,
Brewster, MA 02631

Explore by feature - Pool

FURNISHED
$2,200/mo
Total price
2 bd
2.5 ba
1,380 sqft
30 Crescent Ln,
Brewster, MA 02631
APPLY INSTANTLY
FURNISHED
$3,000/mo
Total price
2 bd
2 ba
950 sqft
53 Chilton Ln,
Brewster, MA 02631
APPLY INSTANTLY
FURNISHED
$2,000/mo
Total price
2 bd
2 ba
935 sqft
218 Eaton Ln,
Brewster, MA 02631
APPLY INSTANTLY
$1,850/mo
Total price
1 bd
1.5 ba
1,380 sqft
35 Chestnut Cir,
Brewster, MA 02631
APPLY INSTANTLY
FURNISHED
$3,500/mo
Total price
3 bd
2.5 ba
1,144 sqft
5 Commons Way,
Brewster, MA 02631

Explore by feature - Washer/dryer

9 rentals with a washer/dryer in Brewster, MA

APPLY INSTANTLY
FURNISHED
$2,500/mo
Total price
2 bd
2 ba
1,000 sqft
258 Sheep Pond Dr,
Brewster, MA 02631
FURNISHED
$2,200/mo
Total price
2 bd
2.5 ba
1,380 sqft
30 Crescent Ln,
Brewster, MA 02631
APPLY INSTANTLY
FURNISHED
$3,000/mo
Total price
2 bd
2 ba
950 sqft
53 Chilton Ln,
Brewster, MA 02631
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$2,300/mo
Total price
2 bd
1 ba
600 sqft
133 Millstone Rd,
Brewster, MA 02631
APPLY INSTANTLY
FURNISHED
$2,000/mo
Total price
2 bd
2 ba
935 sqft
218 Eaton Ln,
Brewster, MA 02631
APPLY INSTANTLY
$1,850/mo
Total price
1 bd
1.5 ba
1,380 sqft
35 Chestnut Cir,
Brewster, MA 02631
APPLY INSTANTLY
FURNISHED
$1,850/mo
Total price
4 bd
2 ba
1,703 sqft
33 Brier Ln,
Brewster, MA 02631
APPLY INSTANTLY
FURNISHED
$3,500/mo
Total price
3 bd
2.5 ba
1,144 sqft
5 Commons Way,
Brewster, MA 02631
PET FRIENDLY
FURNISHED
$4,000/mo
Total price
3 bd
3 ba
1,783 sqft
549 S Orleans Rd,
Brewster, MA 02631

Apartments for Rent

Skip to last item

Contact for price
1-2 bd
1-2 ba
390 Orleans Rd #776f18ccb,
North Chatham, MA 02650
Contact for price
1-2 bd
1-2 ba
383 S Orleans Rd #f320a52c6,
Brewster, MA 02631
APPLY INSTANTLY
FURNISHED
$2,450/mo
Total price
1 bd
1.5 ba
44 Misty Meadow Ln #5,
North Chatham, MA 02650
See more homes for rent in
Brewster
Take a look

Skip to first item

Off Market Homes Near 183 Wayside Drive

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SOLD
SEP 18, 2026
$790,000
3 bd
2 ba
1,372 sqft
33 Sandpiper Lane,
Brewster, MA 02631
Today Real Estate
SOLD
SEP 18, 2026
$860,000
3 bd
3 ba
1,618 sqft
96 Stage Coach Drive,
South Chatham, MA 02659
Gibson Sotheby's International Realty
SOLD
SEP 18, 2026
$1,000,000
3 bd
1 ba
1,201 sqft
268 Barn Hill Road,
Chatham, MA 02633
Compass
SOLD
SEP 16, 2026
$522,500
2 bd
2 ba
1,063 sqft
11 Howland Cir #11,
Brewster, MA 02631
Donna Arthur, ERA Key Realty Services- Milf
SOLD
SEP 16, 2026
$382,000
2 bd
2 ba
935 sqft
90 Eaton Lane UNIT 90,
Brewster, MA 02631
Keller Williams Realty
SOLD
SEP 15, 2026
$899,000
2 bd
2 ba
2,127 sqft
1068 Main Street,
Chatham, MA 02633
William Raveis Non-Member Office
SOLD
SEP 15, 2026
$889,000
2 bd
2 ba
2,127 sqft
1068 Main St #1068,
Chatham, MA 02633
Kristin Coletti, William Raveis R.E. & Home Services
SOLD
SEP 11, 2026
$1,000,000
2 bd
1 ba
702 sqft
79 Cranberry Lane,
Chatham, MA 02633
William Raveis Real Estate & Home Services
SOLD
SEP 11, 2026
$870,000
2 bd
2 ba
2,118 sqft
8 Lakeway Lane,
Harwich, MA 02645
Compass Massachusetts, LLC
SOLD
SEP 10, 2026
$855,000
3 bd
2 ba
1,440 sqft
116 Bittersweet Drive,
Brewster, MA 02631
Today Real Estate
See more homes for sale in
Brewster
Take a look

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Homes for sale near 183 Wayside Drive

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0.34 ACRES
$775,000
3 bd
2 ba
1,764 sqft
193 Wayside Drive,
Brewster, MA 02631
Keller Williams Realty
0.36 ACRES
$659,000
3 bd
2 ba
1,240 sqft
1 Kimberley Way,
Harwich, MA 02645
Insight Realty Group, Inc
0.25 ACRES
$629,900
2 bd
1.5 ba
1,402 sqft
22 McGuerty Road,
Harwich, MA 02645
Christie's International Real Estate Atlantic Brokerage
0.74 ACRES
$1,400,000
3 bd
3 ba
2,432 sqft
3 Bay Wood Drive,
Orleans, MA 02653
Gibson Sotheby's International Realty
NEW CONSTRUCTION
0.92 ACRES
$1,999,999
4 bd
3.5 ba
3,075 sqft
Lot 1 Ladue Landing,
Harwich, MA 02645
Kinlin Grover Compass
0.33 ACRES
$1,150,700
4 bd
3 ba
2,163 sqft
21 Mill Pond Road,
Harwich, MA 02645
Andrew Abu, Inc.
0.25 ACRES
$2,700,000
7 bd
6.5 ba
3,548 sqft
645 S Orleans Road,
Orleans, MA 02653
Berkshire Hathaway HomeServices Robert Paul Properties
See more homes for sale in
Brewster
Take a look

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$695,000

183 Wayside Drive, Brewster, MA 02631

Home Value

Trulia Estimate

Comparable sales

Nearby home prices

Local Information

Home Highlights

About this House

Home Details for 183 Wayside Drive

Interior Features

Exterior Features

Days on Market

Property Information

Price & Status

Active Status

Location

Building

HOA

Lot Information

Listing Info

Miscellaneous

Price and Tax history

Additional Cost

Market trends in Brewster

Around this home

What Locals Say about Brewster

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

Frequently asked questions about 183 Wayside Drive

Explore by feature - Air Conditioning

Explore by feature - Pool

Explore by feature - Washer/dryer

Apartments for Rent

Off Market Homes Near 183 Wayside Drive

Homes for sale near 183 Wayside Drive