5 Windy Hill Dr, Wareham, MA 02571
Property image
Property image
OFF MARKET

$773,400

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 3,750 sqft (on 1.41 acres)

5 Windy Hill Dr, Wareham, MA 02571

Est. Refi. Payment $4,705/mo*
Refinance Your Home
Currently Off Market - Sold Aug 30, 1994 for $161,000

Home Value

Trulia Estimate
$773K
Since last month
Decreased$2K (-0.3%)
Since last year
Increased$25K (+3.3%)
Since last sale
Increased$612K (+380.4%)
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 +104% in the last 10 years
MonthEstimated value
2026
August 2026$773K
July 2026$776K
June 2026$780K
May 2026$786K
April 2026$768K
March 2026$748K
February 2026$731K
January 2026$735K
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
11 Fonseca Way, Wareham, MA
0.26
Single-Family Home
$825,000
01/15/26
4
2.5
3,075
8 Windy Hill Dr, Wareham, MA
0.06
Single-Family Home
$482,500
03/26/26
3
2
1,310
715 County Rd, Rochester, MA
0.15
Single-Family Home
$699,900
05/29/26
3
3.5
1,872
152 Fearing Hill Rd, Wareham, MA
0.63
Single-Family Home
$765,000
11/12/25
4
3
2,896
41 Papermill Rd, West Wareham, MA
0.58
Single-Family Home
$763,000
09/15/25
4
2.5
2,975
4 White Pine Ave, Wareham, MA
0.31
Single-Family Home
$500,000
04/23/26
6
2
1,550
351 County Rd, Rochester, MA
0.67
Single-Family Home
$850,000
08/11/26
4
2.5
2,916
490 High St, Rochester, MA
0.50
Single-Family Home
$805,000
03/17/26
3
3
1,904
456 High St, Rochester, MA
0.67
Single-Family Home
$759,900
09/11/25
4
3
1,904
507 High St, Rochester, MA
0.50
Single-Family Home
$739,000
09/30/25
3
2
1,530

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
8 Windy Hill Dr, Wareham, MA 02571
0.06
$482,500
3
2
1,310
Recently Sold
715 County Rd, Rochester, MA 02770
0.15
$699,900
3
3.5
1,872
Recently Sold
17 Windy Hill Dr, Wareham, MA 02571
0.21
$621,400
3
2
1,664
Off Market
6 Helen St, Wareham, MA 02571
0.26
$510,200
3
1
1,320
Off Market
7 Helen St, Wareham, MA 02571
0.27
$530,000
3
2
1,331
Recently Sold
9 Helen St, Wareham, MA 02571
0.28
$488,900
3
1
1,008
Off Market
11 Fonseca Way, Wareham, MA 02571
0.26
$825,000
4
2.5
3,075
Recently Sold
46 Helen St, West Wareham, MA 02576
0.29
$569,900
3
2
1,352
Recently Sold
2 Helen St, Wareham, MA 02571
0.29
$450,900
3
1
960
Off Market
153 County Rd, West Wareham, MA 02576
0.30
$829,600
2
2
2,472
Off Market
4 White Pine Ave, Wareham, MA 02571
0.31
$500,000
6
2
1,550
Recently Sold
10 White Pine Ave, Wareham, MA 02571
0.33
$456,100
3
1
1,254
Off Market

Local Information

  • Map ViewExplore the area around 5 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
1.41 acres
Living Area
3,750 sqft
Price/Sqft
$206
Parking
Garage

About this House

Short Sale ... Buyer to perform own due diligence and assume or pay two betterment payments as above ( 25K approx. total balance or payments as above) 5 Windy Hill Drive is a huge home in a small, quiet neighborhood just seconds from 495! It has 4 bedrooms and 3 full baths, an attached two car garage with bonus room above it, a large fenced in yard with a big deck where you can sit and watch the kids swim in the in ground pool that even has a slide! *** Buyer must have valid pre-approval ( not prequalification ), and buyer must have home inspection PRIOR to short sale submission to the bank ***
5 Windy Hill Dr, Wareham, MA 02571 is a 4 bedroom, 3 bathroom, 3,750 sqft single-family home built in 1988. It last sold for $161,000 on Aug 30, 1994. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $773,400, with a rent estimate of $4,797/month.

Home Details for 5 Windy Hill Dr

Interior Features

Interior Details
BasementAtticIn-law unitNumber of Rooms: 10Types of Rooms: Walk In Closet, Family RoomCeiling Fan
Heating & Cooling
Heating: Baseboard, Oil, Wood PelletHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Laminate
Appliances & Utilities
Cable Ready
Fireplace & Spa
Jetted Bath Tub

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: VinylLawnPatio
Pool
Pool
Parking & Garage
GarageParking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.41 acres

Mobile R/V

RV Parking
Rv Parking

Price and Tax history

DateEventPrice
Mar 25, 2017
Source: Agent Provided
ListingRemoved
$350,000
Jan 30, 2017
Source: Agent Provided
Listed For Sale
$350,000
Sep 30, 2016
Source: Agent Provided
ListingRemoved
$359,900
Sep 15, 2016
Source: Agent Provided
Pending
$359,900
Aug 21, 2016
Source: Agent Provided
Listed For Sale
$389,900

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 5 Windy Hill Dr

  • What is 5 Windy Hill Dr estimated to be worth?
    Trulia's estimated value for 5 Windy Hill Dr in Wareham, MA is $773,400.
  • What is the price history for 5 Windy Hill Dr?
    5 Windy Hill Dr in Wareham, MA last sold for $161,000 in August 1994.
  • 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.
  • Does 5 Windy Hill Dr have a pool?
    Yes, 5 Windy Hill Dr in Wareham, MA has a pool.
  • How big is the lot at 5 Windy Hill Dr?
    The lot at 5 Windy Hill Dr in Wareham, MA is about 1.4 acres.

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