86 Windy Hill Rd, Westbrook, CT 06498
Property image
Property image
OFF MARKET

86 Windy Hill Rd
Westbrook, CT 06498

  • 2 Beds
  • 1 Bath
  • 900 sqft (on 0.50 acres)

$400,400

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $2,759/mo*
Refinance Your Home

$400,400

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $2,759/mo*
Refinance Your Home
2 Beds
1 Bath
900 sqft
(on 0.50 acres)

Local Information

  • Map ViewExplore the area around 86 Windy Hill Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1945
Lot Size
0.5 acres
Living Area
900 sqft
Price/Sqft
$445

Description

This single-family home is located at 86 Windy Hill Rd, Westbrook, CT. 86 Windy Hill Rd is in Westbrook, CT and in ZIP code 06498. This property has 2 bedrooms, 1 bathroom and approximately 900 sqft of floor space. This property has a lot size of 0.50 acres and was built in 1945.
86 Windy Hill Rd, Westbrook, CT 06498 is a 2 bedroom, 1 bathroom, 900 sqft single-family home built in 1945. It last sold for $190,000 on Apr 8, 2013. It is currently off market. The Trulia Estimate is $400,400, with a rent estimate of $2,151/month.

Home Details for 86 Windy Hill Rd

Interior Features

Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 4
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1945
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Exterior Features

Exterior Home Features
Exterior: OtherFoundation Type: Slab

Community

Units in Building: 1

Lot Information

Lot Area: 0.50 acres

Price History for 86 Windy Hill Rd

DatePriceEventSource
04/08/2013$190,000Sold
Smart MLS #M9138534

Market trends in Westbrook

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
18
3MoM
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Property Tax and Assessment

Year2025
Tax$3,514
Assessment$156,170
Home facts updated by county records

Comparable Sales for 86 Windy Hill Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1020 Old Clinton Road, Westbrook, CT
0.30
Single-Family Home
$410,000
03/10/26
4
1
1,314
328 Hammock Road North, Westbrook, CT
0.14
Single-Family Home
$380,000
04/10/26
3
1.5
2,198
30 Dowd Road, Westbrook, CT
0.19
Single-Family Home
$425,000
12/18/25
2
2
2,722
1259 Old Clinton Road, Westbrook, CT
0.57
Single-Family Home
$450,000
05/15/26
3
1
1,200
257 Pond Meadow Road, Westbrook, CT
0.71
Single-Family Home
$490,000
11/21/25
2
1
1,784
996 Boston Post Rd, Westbrook, CT
0.44
Single-Family Home
$400,000
11/12/25
3
2
1,778
49 Seaside Avenue, Westbrook, CT
0.42
Single-Family Home
$550,000
12/17/25
3
2
2,052
405 Pond Meadow Road, Westbrook, CT
0.91
Single-Family Home
$400,000
06/26/26
3
2
1,281
86 Grove Beach Road North, Westbrook, CT
1.19
Single-Family Home
$364,900
03/13/26
3
1
935
343 Pond Meadow Road, Westbrook, CT
0.83
Single-Family Home
$452,000
08/20/25
3
1.5
1,940

Nearby homes

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Assigned Schools

These are the assigned schools for 86 Windy Hill Rd.
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 Westbrook

At least 31 Trulia users voted on each feature.

  • 89 % Say parking is easy

  • 88 % Say it's dog friendly

  • 86 % Say yards are well-kept

  • 82 % Say kids play outside

  • 80 % Say there's wildlife

  • 77 % Say people would walk alone at night

  • 71 % Say car is needed

  • 71 % Say there's holiday spirit

  • 68 % Say streets are well-lit

  • 66 % Say it's quiet

  • 62 % Say it's walkable to restaurants

  • 61 % Say neighbors are friendly

  • 61 % Say they plan to stay for at least 5 years

  • 53 % Say there are sidewalks

  • 39 % Say it's walkable to grocery stores

  • 34 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Annie Picardi
    "Beautiful area ,public transit is excellent,Resturant’s, shopping close by, Catholic Church is a bit far from our area, other houses of worship are close by,neighbors are friendly"
    0
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  • Annie Picardi
    "Great neighbors , awesome restaurants, amazing beach, easy accessibility to I 95 , walking distance to buses and shore line east train, under a mile and half to Amtrak station, nice churches, convient to three grocery stores, "
    0
    Flag
  • Annie Picardi
    "Great neighborhood nice friendly neighbors Cute dogs in the area easy to get to grocery stores retail stores and houses of worship "
    0
    Flag
  • Annie Picardi
    "Great neighborhood nice residents good shopping a nice variety of restaurants , nice movie theatre easy access to I95, only downfall is the coyotes"
    0
    Flag
  • Meredithawerner
    "Yrs family Friendly neighborhood great schools And quiet and safe for kids! Great schools and safe neighborhoods"
    1
    Flag
  • Meredithawerner
    "Great schools quiet family friendly neighborhood and cute small town low taxes easy beach access safe family friendly "
    1
    Flag
  • Rajay55
    "I have lived here for about 20 years, it’s ver safe. It’s closer to I95 and train station. Town beach is a great place to go anytime of the day."
    2
    Flag
  • Raj
    "I have been living her for 18 years, it is Nice quite small town. Town has clean and well maintained beach. There new library, schools are upgraded. I feel Safe living here. There is newly built train transit station for easier commute to New Haven and New London. There two outlet malls within 10 miles. There are Several of mom and pops restaurants for great food."
    7
    Flag
  • Navynique
    "There are many families and amazing schools, but most streets do not have sidewalks and are too winding and wooded to let kids play/ride bikes in the street."
    4
    Flag
  • Quincy S.
    "Yes, dog friendly place with many dog owners and dog walkers. Good places to go walking with dogs. "
    1
    Flag
  • Christian P.
    "I live there. It is important to note that there is almost nothing to do in Westbrook. At least because I don’t have a car I take the train or bus to work or to get around. Keep in mind that I strongly recommend getting your groceries delivered to your house if you don’t have a car."
    10
    Flag
  • Ruthlesstwo2
    "Neighborhood is very peaceful. The people are nice and the cars don’t speed in our neighborhood. And there are very few homes for sale near us. "
    2
    Flag
  • Ruthlesstwo2
    "I have lived in this neighborhood for 25 years, most of the neighbors are really nice people to live near. "
    1
    Flag
  • Matt D.
    "I work and live here with kids in the elementary school. Very safe and proper place to raise the youngins. The shoreline is beautiful and water is calm. Lot's of fun in the Summer and a private hideaway during the other Seasons."
    0
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  • Matt D.
    "Great for the kids and the Long Island Sound is clean. Islands for exploring and lots of friendly people"
    0
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Apartments for Rent

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Homes for sale near 86 Windy Hill Rd

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Off Market Homes Near 86 Windy Hill Rd

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