18 Windy Hill Dr, Wareham, MA 02571
OFF MARKET

18 Windy Hill Dr
Wareham, MA 02571

  • 3 Beds
  • 2 Baths
  • 1,306 sqft (on 1.99 acres)

$547,400

Trulia Estimate
as of Aug 25, 2026

$547,400

Trulia Estimate
as of Aug 25, 2026
3 Beds
2 Baths
1,306 sqft
(on 1.99 acres)

Home Value

Trulia Estimate
$547K
Since last month
Decreased$3K (-0.6%)
Since last year
Increased$23K (+4.3%)
Since last sale
Increased$300K (+121.4%)
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 +82% in the last 10 years
MonthEstimated value
2026
August 2026$547K
July 2026$550K
June 2026$556K
May 2026$559K
April 2026$552K
March 2026$544K
February 2026$528K
January 2026$524K
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
8 Windy Hill Dr, Wareham, MA
0.18
Single-Family Home
$482,500
03/26/26
3
2
1,310
715 County Rd, Rochester, MA
0.36
Single-Family Home
$699,900
05/29/26
3
3.5
1,872
507 High St, Rochester, MA
0.66
Single-Family Home
$739,000
09/30/25
3
2
1,530
7 Helen St, Wareham, MA
0.35
Single-Family Home
$530,000
05/29/26
3
2
1,331
527 High St, Rochester, MA
0.67
Single-Family Home
$739,900
12/10/25
3
2
1,530
46 Helen St, West Wareham, MA
0.29
Single-Family Home
$569,900
03/27/26
3
2
1,352
11 Fonseca Way, Wareham, MA
0.23
Single-Family Home
$825,000
01/15/26
4
2.5
3,075
4 White Pine Ave, Wareham, MA
0.46
Single-Family Home
$500,000
04/23/26
6
2
1,550
4 Hatchery Ln, Wareham, MA
0.74
Single-Family Home
$620,000
05/22/26
3
2
1,574
44 Helen St, Wareham, MA
0.55
Single-Family Home
$585,000
03/27/26
3
2
1,352

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
17 Windy Hill Dr, Wareham, MA 02571
0.07
$624,600
3
2
1,664
Off Market
191 Pineviewter, West Wareham, MA 02576
0.15
$212,500
2
2
1,064
Recently Sold
8 Windy Hill Dr, Wareham, MA 02571
0.18
$482,500
3
2
1,310
Recently Sold
10 Griffin Way, Wareham, MA 02571
0.24
-
3
2.5
2,642
Off Market
11 Fonseca Way, Wareham, MA 02571
0.23
$825,000
4
2.5
3,075
Recently Sold
8 Griffin Way, Wareham, MA 02571
0.26
$853,000
5
3.5
3,383
Off Market
46 Helen St, West Wareham, MA 02576
0.29
$569,900
3
2
1,352
Recently Sold
41 Papermill Rd, West Wareham, MA 02576
0.39
$785,000
4
2.5
2,975
Off Market
715 County Rd, Rochester, MA 02770
0.36
$699,900
3
3.5
1,872
Recently Sold
9 Helen St, Wareham, MA 02571
0.34
$491,200
3
1
1,008
Off Market
3 Candle Paper Lane, Wareham, MA 02571
0.40
$817,500
3
2.5
2,136
Off Market
7 Helen St, Wareham, MA 02571
0.35
$530,000
3
2
1,331
Recently Sold

Local Information

  • Map ViewExplore the area around 18 Windy Hill Dr.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1988
Lot Size
1.99 acres
Living Area
1,306 sqft
Price/Sqft
$419

About this House

Located on the Rochester town line, this attractive, well-maintained Cape is nestled on almost 2 acres of wooded land in the heart of cranberry country. This three-bedroom, two bath home is located near the end of a cul-de-sac and is in move-in condition. Amenities include a fireplace, large deck in rear, and many updates, including (but not limited to) both baths, new roof, vinyl trim, wood stove, and new carpeting throughout. Finished, heated rooms in basmt.Quick, easy access Routes 495 & 195.
18 Windy Hill Dr, Wareham, MA 02571 is a 3 bedroom, 2 bathroom, 1,306 sqft single-family home built in 1988. It last sold for $247,000 on Mar 15, 2013. It is currently off market. The Trulia Estimate is $547,400, with a rent estimate of $3,258/month.

Home Details for 18 Windy Hill Dr

Interior Features

Interior Details
BasementNumber of Rooms: 5
Heating & Cooling
Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 1.99 acres

Price and Tax history

DateEventPrice
Mar 15, 2013
Source: N/A
Sold
$247,000
Aug 17, 2012
Source: Agent Provided
PriceChange
$249,900
Price decreased by 2%
Aug 11, 2012
Source: Agent Provided
Listed For Sale
$254,900
Jun 30, 1998
Source: N/A
Sold
$145,500
Oct 13, 1995
Source: N/A
Sold
$126,500

Market trends in Wareham

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$493K
$9.67KMoM
Sale-to-List Price
100.8%
0.3%MoM
Price per sq ft
$383
$10MoM
Available listings
89
5MoM

Around this home

What Locals Say about Wareham

At least 138 Trulia users voted on each feature.

  • 86 % Say car is needed

  • 86 % Say it's dog friendly

  • 86 % Say yards are well-kept

  • 83 % Say parking is easy

  • 75 % Say there's holiday spirit

  • 72 % Say there's wildlife

  • 62 % Say people would walk alone at night

  • 59 % Say kids play outside

  • 56 % Say neighbors are friendly

  • 54 % Say it's walkable to restaurants

  • 53 % Say they plan to stay for at least 5 years

  • 48 % Say it's quiet

  • 41 % Say it's walkable to grocery stores

  • 40 % Say there are sidewalks

  • 33 % Say streets are well-lit

  • 28 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • ElliceAnn
    "Very walkable, but it would be nice to see more local small shops be welcoming of dogs, even if it was just water bowls/treats outside"
    0
    Flag
  • Deemoff23
    "I’ve been in this area for about 3 years now. Very family oriented neighborhood, was invited for a few things even though people didn’t know me. I have enjoyed my time here so far. "
    0
    Flag
  • Trulia User
    "The downtown is quaint with shopping, eating, and laundry. Nearby are art galaries and beautiful beaches! There is so much to do with many planned events throughout the year. "
    4
    Flag
  • Trulia User
    "is a beautiful area to live in surrounded by water. friendly neighborhoods neighbors watch out for each other. great restaurants."
    0
    Flag
  • Trulia User
    "no sidewalks in most spaces for safety. Dogs aren't allowed on beaches. There are some areas they could be reasonably be allowed as long as owners picked up after them. There are parks & grassy areas. little shade. No dog parks. Lots of side streets."
    1
    Flag
  • Michellezine
    "It’s a beach community that is private. The neighbors are wonderful and it’s a great place to spend summers! "
    4
    Flag
  • Product 3.
    "It’s right off 195. Also cranberry highway and route 6 that goes to RI. It’s not bad. Mostly town roads aside from the 195"
    8
    Flag
  • Beth C. F.
    "My neighbors are friendly and helpful. We’ve lived here eight years and we love it. There aren’t many kids here my daughters age, but that’s my only complaint "
    2
    Flag
  • Dakota A.
    "There is a lot of wildlife around. Most dogs chase after wildlife so their dog might go to chase after the animal. It’s a good neighborhood. "
    2
    Flag
  • Bill.labossiere
    "Most of the time people keep to themselves. People drive too fast. Not much of a community based town. Lots of low income. "
    6
    Flag
  • Darla F.
    "My neighborhoods has five homes on the street, they are all on 1+ acres. Very quiet and private. Good access to Providence, Boston and sitting just before you cross the Bourne Bridge to Cape Cod. Walking distance to downtown. One block off the water."
    5
    Flag
  • Patrick S.
    "Summertime activities are the best in Onset. Fireworks on the Fourth of July concerts in the park every Wednesday night and even a kite festivals "
    5
    Flag
  • Cindy L.
    "what parts of Wareham to keep their children away from where there is criminal activity going on and twin to look into the school systems and see which school is best for their children"
    10
    Flag
  • Mileswatson22
    "Cape Verdean festival Portuguese festival Small town community action Fireworks in Onset And most importantly, Cazimir’s Barbershop. EST. 2003"
    0
    Flag
  • Ewhite1288
    "I think it’s great for dogs. Plenty of socialization. If they have a dog that is dog or people aggressive not a good neighborhood. "
    2
    Flag
  • Main Street Resident
    "I work in the North Dartmouth area, and my morning commute is usually incident free. The same goes for coming back to this area. Coming home there is sometimes traffic congestion on my street due to the “Pot Shop” located a few hours away from where I live."
    5
    Flag
  • Leslie P
    "Lots of dogs in area. Wide variety from pit bulls to Chihuahuas. Most people are respectful but there are a few that don’t pick up after them."
    0
    Flag
  • Jude
    "Extremely convenient with walkable destinations. Tobey Hospital, convenient stores, Dunk’n, Park with water pier, school, library, CVS, and restaurants are all in walking distance,"
    0
    Flag
  • Trulia User
    "You are near a river and boat pier. You can walk to a convenient store, several restaurants, Library, gas station, commuter train stop, and pot shop."
    1
    Flag
  • Judy
    "It has a nice park near the Wareham Pier, quite, safe, homes are key well, hospital close, walkable to Convenient store and restaurants."
    0
    Flag
  • Judithelopes
    "There is a park located at the Wareham Pier. A lot of people walk their dog past my house. Great place to live."
    1
    Flag
  • Nicole D.
    "I work 5 miles from work. It is on a divided highway. There are 2 sets of lights, 3 gas stations, 2 Dunkin Donuts and 2 convenience stores."
    1
    Flag
  • Watercomm
    " Great neighborhood to raise children and have fun. A little out of the way but nice. Please check things out to know you would like to live here."
    0
    Flag
  • Lisa S.
    "Sitting in my back yard watching the boats go by. The view is very calming. Kayaking or paddle boating is great too. Watching the sunrise in the morning."
    1
    Flag
  • Watercomm
    "We have lived here for many many years and enjoy our quaint community. Local businesses and near all major highways "
    0
    Flag
  • Watercomm
    "Friendly, quiet, clean and wonderful to raise a family or retire in. Several ponds near by for swimming and fishing."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 18 Windy Hill Dr

  • What is 18 Windy Hill Dr estimated to be worth?
    Trulia's estimated value for 18 Windy Hill Dr in Wareham, MA is $547,400.
  • What is the price history for 18 Windy Hill Dr?
    18 Windy Hill Dr in Wareham, MA last sold for $247,000 in March 2013.
  • Is Wareham a buyer's or seller's market?
    Wareham is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Wareham?
    The median sale price in Wareham is $493K. That is up $9.67K from the prior month.
  • How big is the lot at 18 Windy Hill Dr?
    The lot at 18 Windy Hill Dr in Wareham, MA is about 2 acres.

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