1663 Windward Dr, Hampshire, IL 60140
OFF MARKET

1663 Windward Dr
Hampshire, IL 60140

  • Studio

$290,400

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $1,547/mo*
Refinance Your Home

$290,400

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $1,547/mo*
Refinance Your Home
Studio

Local Information

  • Map ViewExplore the area around 1663 Windward Dr.
  • Schools1 Preschool School1 Elementary School1 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 1663 Windward Dr, Hampshire, IL. 1663 Windward Dr is in Hampshire, IL and in ZIP code 60140. This property has a lot size of 1306 sqft.
1663 Windward Dr, Hampshire, IL 60140 is a studio single-family home. It last sold for $133,500 on Jul 29, 2015. It is currently off market. The Trulia Estimate is $290,400, with a rent estimate of $2,640/month.

Home Details for 1663 Windward Dr

Property Information

Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 1306 sqft

Price History for 1663 Windward Dr

DatePriceEventSource
07/29/2015$133,500Sold
N/A

Market trends in Pingree Grove

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
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Price per sq ft
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Available listings
39
2MoM
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Property Tax and Assessment

Year2024
Tax$5,807
Assessment$210,627
Home facts updated by county records

Comparable Sales for 1663 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1365 Broadland Dr, Hampshire, IL
0.23
Single-Family Home
$400,000
06/30/26
3
2.5
2,128
1341 Cape Cod Ln, Hampshire, IL
0.34
Single-Family Home
$320,000
10/17/25
3
3
1,793
902 Clover Ln, Hampshire, IL
0.79
Single-Family Home
$265,000
03/24/26
2
2.5
1,728
1595 Prospect Cir, Hampshire, IL
0.25
Single-Family Home
$445,000
11/18/25
4
2.5
2,128
1863 Lake Bluff Ln, Hampshire, IL
0.22
Single-Family Home
$530,000
06/30/26
5
3.5
3,106
1889 Lake Bluff Ln, Hampshire, IL
0.26
Single-Family Home
$433,000
08/04/26
4
2.5
2,900
1385 Broadland Dr, Hampshire, IL
0.24
Single-Family Home
$416,000
02/24/26
4
2.5
2,799
1114 Port Royal Rd, Hampshire, IL
0.27
Single-Family Home
$424,900
04/08/26
4
2.5
2,157
1133 Daytona Way, Hampshire, IL
0.35
Single-Family Home
$453,000
07/15/26
4
2.5
2,680
1566 Dublin Dr, Hampshire, IL
0.36
Single-Family Home
$465,000
07/24/26
4
2.5
2,600

Nearby homes

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Assigned Schools

These are the assigned schools for 1663 Windward Dr.
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 Pingree Grove

At least 52 Trulia users voted on each feature.

  • 98 % Say it's dog friendly

  • 95 % Say there are sidewalks

  • 89 % Say car is needed

  • 79 % Say parking is easy

  • 79 % Say kids play outside

  • 78 % Say it's quiet

  • 75 % Say people would walk alone at night

  • 71 % Say there's holiday spirit

  • 68 % Say streets are well-lit

  • 67 % Say yards are well-kept

  • 55 % Say neighbors are friendly

  • 55 % Say there's wildlife

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

  • 45 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Kristofer
    "This is a great town but there’s a ton of traffic and it takes forever to get to the store. They are building a new Jewel soon right down the street. Beautiful houses and community center is great "
    0
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  • Trulia User
    "One of the best small quiet kept gem of a neighborhood in the north west suburbs. Peaceful. Diverse. But getting pricier "
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  • Xqrzvcdn9t
    "I have lived in this neighborhood for almost 11 years and it’s a great place to live. The town is wonderful with Christmas lights and other seasonal lights and there are a lot of dogs running around with their owners and they are great as well."
    0
    Flag
  • Jaclyn B.
    "Friends are in the neighborhood. Great for families and young kids. Would recommend for young families."
    2
    Flag
  • Cassie B.
    "Love Cambridge lakes, can’t wait to raise a family here. Great homes, great paths. Perfect neighborhoods here. "
    0
    Flag
  • Cassie B.
    "Lots of people with dogs! Great paths for walking. Lots of other dogs to socialize with as well. Dog/animal friendly people."
    0
    Flag
  • Ssterling980
    "Every house has a dog! The bike paths are great for long walks. The townhouses are not great for big dogs but still a lot of people have 1 or more in them. Many members of the community have expressed the need for a dog park, but no word on anything like that happening."
    0
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  • Smcguire28
    "It’s not unique a unique neighborhood. I have nothing good to say. Cars get broken into everyday and packages are often stolen "
    1
    Flag
  • Mallory L.
    "Love this area! It’s the perfect combination of suburbs and country. Tons of beauty, but close enough that it’s convenient. Lots of kids and young families!"
    0
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  • Travelersoul
    "Everyone is very friendly & says hi. It is a very nice neighborhood to live in. I would definitely recommend this area to anyone. "
    0
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  • KB
    "My neighborhood is wholesome and close knit. We love it here! We look out for each other. Everyone is so friendly."
    0
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  • Cesar T.
    "Excellent community, safe and fun for all ages. The sense of familiarity and cooperation with neighbors is amazing."
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  • Isa
    "I’ve lived in Pingree Grove for 7 years. This neighborhood is friendly, peaceful, great community to raise children. Very safe, you can walk, ride a bike, just relax at any time. Great outdoor activities. Enjoy the lakes and the gazebo, a plus for this wonderful community. "
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  • Trulia User
    "Community events community plans special events throughout the year. Friendly people. Lots of paths to walk, ride bikes. "
    0
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  • Christine M.
    "We are new to the neighborhood and so far we love it!! my neighbors are nice, there is alot of kids and dogs! "
    0
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  • Kevin B.
    "we have a great 4th of July fire works display. And just before Christmas the Holiday train stops in our small town. "
    1
    Flag
  • Jorhenao
    "It’s great and confortable safe I like this area because is relax and lakes The guys’ll play on the street safe The landscape es beautiful and amazing thank "
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

10 pet-friendly rentals in Hampshire, IL

Explore by feature - Garage

18 rentals with a garage in Hampshire, IL

Explore by feature - Air Conditioning

22 rentals with air conditioning in Hampshire, IL

Explore by feature - Pool

14 rentals with a pool in Hampshire, IL

Explore by feature - Washer/dryer

17 rentals with a washer/dryer in Hampshire, IL

Homes for sale near 1663 Windward Dr

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Off Market Homes Near 1663 Windward Dr

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Frequently asked questions about 1663 Windward Dr

  • What is 1663 Windward Dr estimated to be worth?
    Trulia's estimated value for 1663 Windward Dr in Hampshire, IL is $290,400.
  • What is the price history for 1663 Windward Dr?
    1663 Windward Dr in Hampshire, IL last sold for $133,500 in July 2015.
  • Is Hampshire a buyer's or seller's market?
    Hampshire is currently a balanced market, based on recent for-sale activity.
  • What do residents say about Hampshire?
    Residents describe Hampshire, IL as dog-friendly, pedestrian-friendly, and easy to park in. See recently sold homes in Hampshire, IL.
  • How big is the lot at 1663 Windward Dr?
    The lot at 1663 Windward Dr in Hampshire, IL is about 0.03 acres (1,306 sq ft).