14 Winstead Road, Brewster, MA 02631
OFF MARKET

$1,478,600

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 2,500 sqft (on 1.51 acres)

14 Winstead Road, Brewster, MA 02631

Est. Refi. Payment $8,752/mo*
Refinance Your Home
Currently Off Market - Sold Sep 29, 2011 for $746,000

Home Value

Trulia Estimate
$1.48M
Since last month
Increased$87K (+6.3%)
Since last year
Increased$20K (+1.4%)
Since last sale
Increased$733K (+98.2%)
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 decreased by 0% in the last 10 years
MonthEstimated value
2026
September 2026$1.48M
2025

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
1080 Harwich Road, Brewster, MA
0.39
Single-Family Home
$740,000
11/20/25
3
2.5
1,963
52 Bettys Lane, Brewster, MA
0.08
Single-Family Home
$870,000
02/12/26
3
2
2,317
72 Winstead Road, Brewster, MA
0.10
Single-Family Home
$1,678,000
07/21/26
4
3.5
3,021
21 High Point Drive, Brewster, MA
0.43
Single-Family Home
$1,195,000
10/02/25
3
2.5
1,737
21 Nancys Way, Brewster, MA
0.58
Single-Family Home
$1,350,000
12/05/25
3
2.5
2,480
147 Brook Trail Road, Brewster, MA
0.49
Single-Family Home
$744,000
06/30/26
3
2
1,983
46 Trout Pond Lane, Brewster, MA
0.67
Single-Family Home
$815,000
06/05/26
3
2
1,778
23 Prince Charles Drive, Harwich, MA
0.27
Single-Family Home
$2,150,000
06/10/26
5
3
3,450
25 High Point Drive, Brewster, MA
0.47
Single-Family Home
$2,175,000
09/18/26
5
3.5
2,927
30 Forsythia Drive, Harwich, MA
0.84
Single-Family Home
$866,000
09/10/26
3
3
2,072

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
4 Winstead Road, Brewster, MA 02631
0.00
-
-
-
-
Off Market
5 Winstead Road, Brewster, MA 02631
0.00
-
-
-
-
Off Market
7 Winstead Road, Brewster, MA 02631
0.00
-
-
-
-
Off Market
9 Winstead Road, Brewster, MA 02631
0.00
-
-
-
-
Off Market
45 Winstead Road, Brewster, MA 02631
0.06
$1,670,600
4
3.5
3,021
Off Market
52 Bettys Lane, Brewster, MA 02631
0.08
$870,000
3
2
2,317
Recently Sold
72 Winstead Road, Brewster, MA 02631
0.10
$1,678,000
4
3.5
3,021
Recently Sold
0 Crowells Bog Road, Brewster, MA 02631
0.15
-
-
-
-
Off Market
34 Prince Charles Drive, Harwich, MA 02645
0.20
-
-
-
-
Off Market
15 Black Loch Drive, Harwich, MA 02645
0.20
$1,263,000
3
3
1,788
Off Market
14 Black Loch Drive, Harwich, MA 02645
0.25
$923,300
4
3
1,955
Off Market

Local Information

  • Map ViewExplore the area around 14 Winstead Road.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2011
1.51 acre lot
2,500 sqft
$591/sqft
2 Car Garage

About this House

Brewster's Newest Subdivision! Pond Oaks is a new fourteen lot subdivision where various lots enjoy views of and short walks to Long Pond, Black Pond and Seymour Pond. Residents will love deeded access to fresh water and the opportunity to live the good life in a beautiful natural environment. Saltwater bay beaches and the scenic bike trail are within minutes of your door. Built by a highly regarded builder who has customized 2645 square feet of living space plus the option to expand. Open floor plan to maximize natural lighting and gracious living. Well-designed kitchen will have beautiful cabinetry with granite countertops, fine details, hardwood flooring and generous fenestration enhance the offerings. 4 bedroom septic. New homes will have a $2500 appliance allowance.
14 Winstead Road, Brewster, MA 02631 is a 3 bedroom, 3 bathroom, 2,500 sqft single-family home built in 2011. It last sold for $746,000 on Sep 29, 2011 (6% above the $704,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,478,600, with a rent estimate of $4,109/month.
Last check for updates: about 20 hours ago
Listed by Alberti Team, (508) 237-2771
oldCape Sotheby's International Realty
Bought with: Whitaker Group Cape Cod, (508) 237-8038, oldCape Sotheby's International Realty
Source: CCIMLS, MLS#21100423

Home Details for 14 Winstead Road

Interior Features

Interior Details
Basement: FullNumber of Rooms: 6
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Appliances & Utilities
Appliances: Natural Gas
Heating & Cooling
Heating: Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Natural Gas
Fireplace & Spa
Number of Fireplaces: 1
Windows, Doors, Floors & Walls
Flooring: Wood, Tile, Carpet
Levels, Entrance, & Accessibility
Stories: 2Floors: Wood, Tile, Carpet

Exterior Features

Exterior Home Features
Roof: Asphalt PitchedExterior: GardenGarden
Parking & Garage
Number of Garage Spaces: 2Has a GarageHas an Attached GarageParking Spaces: 2Parking: Direct Access,Gravel
Frontage
Waterfront: Fresh, Salt, Other - See Remarks, WaterviewNot on Waterfront

Days on Market

Cumulative Days on Market: 1

Property Information

Year Built
Year Built: 2011
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: ClapboardIs a New Construction
Property Information
Condition: Under ConstructionParcel Number: 4981140

Price & Status

Price
List Price: $704,000

Active Status

MLS Status: Closed

Location

Direction & Address
City: Brewster

Building

Building Area
Building Area: 2500 Square Feet

HOA

Has an HOA

Lot Information

Lot Area: 1.51 Acres

Listing Info

Special Conditions: Standard

Miscellaneous

BasementMls Number: 21100423Showing Requirements: Appointment Required, Call Listing Office, Call Listing Agent, Yard Sign

Price and Tax history

DateEventPrice
Sep 29, 2011
Source: CCIMLS #21100423
Sold
$746,000

Market trends in Brewster

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$618K
$73.33KMoM
Sale-to-List Price
—
Price per sq ft
$487
$17MoM
Available listings
55
7MoM

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

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 2026-09-22 13:33:17 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 14 Winstead Road

  • What is 14 Winstead Road estimated to be worth?
    Trulia's estimated value for 14 Winstead Road in Brewster, MA is $1,478,600.
  • What is the price history for 14 Winstead Road?
    14 Winstead Road in Brewster, MA last sold for $746,000 in September 2011.
  • 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 14 Winstead Road have air conditioning?
    Yes, 14 Winstead Road in Brewster, MA has air conditioning.
  • Does 14 Winstead Road have a yard?
    Yes, 14 Winstead Road in Brewster, MA has a yard.

Explore by feature - Air Conditioning

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