37 Pilgrim Drive, Windsor, CT 06095
SOLD
SEP 28, 2026

$465,100

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 1,886 sqft (on 0.80 acres)

37 Pilgrim Drive, Windsor, CT 06095

Est. Refi. Payment $3,443/mo*
Refinance Your Home
Currently Off Market - Sold Sep 28, 2026 for $465,000 (2% above list price)

Home Value

Trulia Estimate
$465K
Since last month
Increased$2K (+0.3%)
Since last year
Increased$90K (+24%)
Since last sale
Increased$300 (+0.1%)
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 +110% in the last 10 years
MonthEstimated value
2026
October 2026$465K
September 2026$464K
August 2026$461K
June 2026$337K
April 2026$399K
March 2026$395K
February 2026$373K
January 2026$383K
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
36 Pilgrim Drive, Windsor, CT
0.03
Single-Family Home
$410,000
05/28/26
4
2
1,526
86 Carriage Way, Windsor, CT
0.18
Single-Family Home
$550,000
07/22/26
4
2.5
2,926
608 Kennedy Road, Windsor, CT
0.48
Single-Family Home
$426,000
03/31/26
4
2
1,399
61 Winthrop Road, Windsor, CT
0.46
Single-Family Home
$470,000
12/29/25
4
2.5
2,036
17 Box Turtle Lane, Windsor, CT
0.42
Single-Family Home
$500,000
12/30/25
4
2.5
2,095
501 Kennedy Road, Windsor, CT
0.32
Single-Family Home
$486,000
12/12/25
3
2.5
1,644
145 Carriage Way, Windsor, CT
0.38
Single-Family Home
$625,000
11/14/25
4
2.5
2,236
40 Alden Road, Windsor, CT
0.36
Single-Family Home
$340,000
02/20/26
4
3
2,110

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
41 Pilgrim Dr, Windsor, CT 06095
0.02
$344,500
3
2
1,542
Off Market
31 Pilgrim Dr, Windsor, CT 06095
0.03
$402,800
4
2
1,764
Off Market
36 Pilgrim Drive, Windsor, CT 06095
0.03
$410,000
4
2
1,526
Recently Sold
47 Pilgrim Dr, Windsor, CT 06095
0.05
$377,000
4
2
1,908
Off Market
40 Pilgrim Dr, Windsor, CT 06095
0.05
$339,700
3
1
1,337
Off Market
27 Pilgrim Dr, Windsor, CT 06095
0.05
$410,300
4
2
1,980
Off Market
30 Glenwood Dr, Windsor, CT 06095
0.06
$372,200
3
2
1,294
Off Market
30 Pilgrim Dr, Windsor, CT 06095
0.06
$389,300
3
2
1,526
Off Market
56-58 Judd Ave, New Britain, CT 06051
0.06
$428,300
6
3
3,048
Off Market
26 Glenwood Dr, Windsor, CT 06095
0.06
$389,300
3
2.5
1,396
Off Market
46 Pilgrim Dr, Windsor, CT 06095
0.06
$371,300
4
2
2,024
Off Market
34 Glenwood Dr, Windsor, CT 06095
0.06
$348,500
3
1.5
1,296
Off Market
53 Pilgrim Dr, Windsor, CT 06095
0.07
$509,500
5
3.5
3,000
Off Market
22 Glenwood Dr, Windsor, CT 06095
0.07
$423,500
3
2.5
1,720
Off Market
26 Pilgrim Dr, Windsor, CT 06095
0.07
$384,000
4
2
1,958
Off Market
21 Pilgrim Dr, Windsor, CT 06095
0.08
$322,600
3
1
1,128
Off Market
52 Pilgrim Dr, Windsor, CT 06095
0.08
$348,700
3
1
1,622
Off Market
18 Glenwood Dr, Windsor, CT 06095
0.08
$410,200
3
2.5
1,794
Off Market
22 Pilgrim Dr, Windsor, CT 06095
0.09
$424,500
3
2
2,172
Off Market
38 Glenwood Drive, Windsor, CT 06095
0.09
$461,200
4
2.5
1,864
Off Market

Local Information

  • Map ViewExplore the area around 37 Pilgrim Drive.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1959
0.8 acre lot
1,886 sqft
$247/sqft
2 Car Garage

About this House

What's unique:Wood-burning stoveBeautifully restored hardwood floorsThermal-pane windowsNewer garage doorsExpansive level groundsFour bedrooms
Discover the timeless appeal of this inviting Cape-style residence, ideally situated in a sought-after neighborhood known for its welcoming character. Offering four bedrooms and two full bathrooms, this home combines classic charm with thoughtful improvements and versatile living spaces designed to accommodate today's lifestyle. Step inside to a warm and comfortable interior where beautifully restored hardwood floors add a sense of craftsmanship and character throughout much of the home. The family room provides a cozy retreat, highlighted by a wood-burning stove that sets the perfect mood for quiet nights and gatherings with family and friends. A generous living area flows naturally into the formal dining space, where hardwood floors and a glass slider create an effortless connection to the outdoors. Whether hosting a festive holiday meal or enjoying a relaxed evening at home, this space offers an inviting setting for every occasion. The kitchen is both functional and welcoming, featuring plentiful storage, a casual dining area, and freshly installed flooring. The first floor also includes two bedrooms with hardwood floors, offering exceptional flexibility for guests, a home office, or those seeking convenient single-floor accommodations. A full bathroom with tile flooring completes this level. The upper floor introduces two additional bedrooms, both featuring hardwood floors, along with another full bathroom, providing a comfortable separation between living and private spaces. Outside, the expansive level grounds offer plenty of room to enjoy the seasons. The patio creates a natural extension of the living space and is well suited for outdoor dining, summer entertaining, or simply enjoying a peaceful afternoon in the yard. Numerous updates add to the home's lasting appeal, including refinished hardwood flooring, thermal-pane windows, 200-amp electrical service, newer garage doors, and a newer water heater. A home offering character, flexibility, and meaningful improvements in an established neighborhood-ready for its next chapter. Come see all that this charming Cape has FOR YOU!
37 Pilgrim Drive, Windsor, CT 06095 is a 4 bedroom, 2 bathroom, 1,886 sqft single-family home built in 1959. It last sold for $465,000 on Sep 28, 2026 (2% above the $455,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $465,100, with a rent estimate of $2,884/month.
Last check for updates: about 7 hours ago
Listed by Andrea Rodriguez, (860) 331-5156
Eagle Eye Realty PLLC, (860) 263-9102
Bought with: Margaret A. DeLuca, (860) 997-0299, William Raveis Real Estate, (860) 633-0111
Source: Smart MLS, MLS#24197082

Home Details for 37 Pilgrim Drive

Interior Features

Interior Details
Basement: Full,Unfinished,Interior Entry,ConcreteNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1886 Square Feet
Appliances & Utilities
Appliances: Electric Range, Convection Range, Microwave, Refrigerator, Dishwasher, Electric Water Heater, Water HeaterDishwasherLaundry: Lower LevelMicrowaveRefrigerator
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: PatioExterior: Fruit Trees, Rain Gutters, GardenFoundation: Concrete PerimeterGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Attached,Off Street,Driveway,Private,Paved,Asphalt
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1886 Square Feet

Property Information

Year Built
Year Built: 1959
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod
Building
Construction Materials: Aluminum SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 777728

Price & Status

Price
List Price: $455,000Price Per Sqft: $247/sqft
Status Change & Dates
Off Market Date: Tue Aug 25 2026Possession Timing: Immediately

Active Status

MLS Status: Closed

Location

Direction & Address
City: Windsor
School Information
Elementary School: Per Board of EdHigh School: Per Board of Ed

Agent Information

Buyer Agent
Buyer Company Name: Margaret Wilcox Team

Building

Building Area
Building Area: 1886 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.80 acres

Miscellaneous

BasementMls Number: 24197082Attic: Crawl Space, Access Via HatchAttribution Contact: (860) 331-5156Above Grade Unfinished Area: 1886

Price and Tax history

DateEventPrice
Sep 28, 2026
Source: Smart MLS #24197082
Sold
$465,000
Aug 25, 2026
Source: Smart MLS #24197082
Pending
$455,000
Aug 15, 2026
Source: Smart MLS #24197082
Listed For Sale
$455,000
Jun 11, 2026
Source: Smart MLS #24159289
Sold
$335,000
May 29, 2026
Source: Smart MLS #24159289
Pending
$329,900

Market trends in Windsor

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$398K
$38.17KMoM
Sale-to-List Price
—
Price per sq ft
$214
$2MoM
Available listings
64
9MoM
Sourced by Trulia Market Trends

Around this home

What Locals Say about Windsor

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 70% say there's holiday spirit
  • 67% say there are sidewalks
  • 55% say neighbors are friendly
Trulia Trick or TreatStart Ghost Hunt
At least 159 Trulia users voted on each feature.

  • 89 % Say car is needed

  • 88 % Say parking is easy

  • 87 % Say it's dog friendly

  • 78 % Say streets are well-lit

  • 77 % Say yards are well-kept

  • 74 % Say people would walk alone at night

  • 70 % Say there's holiday spirit

  • 69 % Say there's wildlife

  • 69 % Say it's quiet

  • 67 % Say there are sidewalks

  • 65 % Say kids play outside

  • 55 % Say neighbors are friendly

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

  • 46 % Say it's walkable to restaurants

  • 46 % Say it's walkable to grocery stores

  • 34 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Keyonna
    "Quiet and everyone keeps to themselves. Only a little noisy during the summer time due to motorcycles."
    0
    Flag
  • Zonoui Smith Jr.
    "I see dogs walked all the time. Some people don’t pick up after them. Also some people let their dogs walk to far into residence yards to use the bathroom "
    0
    Flag
  • Fenn.nathaniel
    "I've lived in this neighbourhood for about 15 years in love that is close to everything and far away from the hustles and bustles of the city."
    10
    Flag
  • Sherianne10315
    "Windsor has a small town feel. People help each other and come together when others are in need. Local farms and shop owners are friendly."
    0
    Flag
  • Kimberlydbigelow
    "I have lived in Windsor for 5 years. It has been the perfect location! I work in downtown Hartford and I take the bus into the city from a commuter lot in my town. It’s a relaxing 15min ride into and out of Hartford and as close as I am to the capital, Windsor is cute with lots of farms and the small, quaint town feel I was looking for. I’m loving it!"
    1
    Flag
  • Unspecified
    "Lots of town activities! Stuff on the green, local businesses, small town feel! Diverse community and polite town members"
    1
    Flag
  • Unspecified
    "There are Town green events all the time! Numerous walking trails filled with people. Strong sense of community. Working with locals is the norm in terms of hiring services."
    0
    Flag
  • Ashley W.
    "Los of people outside walking and a very quiet area very close to the highway. Good sense of community very safe and friendly neighborhood. Can walk to gas or food and close to the center of town and a lot of schools too!"
    0
    Flag
  • G.girardin
    "It’s a friendly and diversified neighborhood. Great walking neighborhood even at night. We’ve lived in Windsor for 35 years and feel very safe here. This is our third neighborhood . We’ve never had any issues. "
    0
    Flag
  • Sarah L.
    "Poquonock school is a wonderful community all the parks are very safe and the parks & rec programs are great"
    0
    Flag
  • Sam B.
    "Great place to stay and bring up a family great school system whatever they are ranked now you have Amazon JCP and others job market is good Parks swimming pools library good shop name it and you have it"
    0
    Flag
  • Sam B.
    "Great place to live grow work Bus and Uber available Mixed crowd Friendly people Great schools Parks pools Best library "
    0
    Flag
  • Sam B.
    "Great place to raise a family schools transport parks people are all great Town have a lot of activity like Shad Derby"
    0
    Flag
  • Shyra E.
    "My neighborhood is amazing it has good transit access and wonderful restaurants and parks hope this helps"
    0
    Flag
  • Carol J. M.
    "I live in this area for 1 year in a 55 and over community and love it! Lots of traffic on 91 and 291 that I do not like."
    1
    Flag
  • Nbjackson
    "Usually on the town green, farmers market, summer outdoor concerts, parades, Halloween event, holiday events, craft fairs"
    0
    Flag
  • Bonny E.
    "Yes dogs are always being walked in this area. They are great here. Kids always playing too. Neighbors helping neighbors. People look out for each other"
    0
    Flag
  • Jeffery I.
    "There are many events and good parks in town. however, you need the spend time finding them. unless you have lived hear for a long time or are active in town it can be hard to find stuff to do."
    0
    Flag
  • Me
    "my neighborhood is awesome, quiet, clean, with sidewalks, and walking trails. The HOA takes care of all the grounds maintenance and all snow removal"
    1
    Flag
  • Angie R.
    "recreation Dept has great programs parks are well maintained school system is getting back on track great family friendly town"
    0
    Flag
  • Me
    "Windsor is a small town. Although there are some rough areas but overall its quiet and safe. Schools are subpart.and taxes are high"
    1
    Flag
  • Wendy S.
    "during the summer they have concerts on the green down town. nice place tp live. quite contry living"
    0
    Flag
  • Me
    "I have lived here for 12 and I am very happy. the neighborhood is quiet and safe the streets are clean and well light"
    0
    Flag
  • ReginaJ
    "Live in the harvest Lane neighborhood for the last 9 years. One of the best places to live in the state. A very sort after neighborhood to live. Took us a while to get a house, because no one moves from it. Unless they are retiring and moving to Florida. The trails that are connected off the street that leads to Northwest Park and the reservoir for hiking are incredible. The family atmosphere is that of an extended family. The kids, the parents even the pets all know each other. We can’t ask for more from such a tranquil place we live in with so much harmony and love. #HarvestLane4Life "
    0
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  • Amy C.
    "Windsor is a town with strong resources and traditions. It has reasonable housing prices and lots of diversity. "
    0
    Flag
  • Carol J. M.
    "We have coffee 9am - 11am once a month and other social events. Dog friendly. Neighbors are very friendly."
    0
    Flag
  • Shanyelle.hamilton
    "Public transportation is easily accessible and downtown Hartford is 15 minutes from Wilson and 30 minutes from the town center by bus or car."
    0
    Flag
  • Shanyelle.hamilton
    "There are plenty of family friendly events in Windsor or the surrounding area. Every Halloween we have Nightmare on Broad Street for kids of all ages to have safe fun."
    0
    Flag
  • Lisanickersondouglas
    "Great schools / diverse community. Easy highway access. Lots of parks and trails for walking. Many annual events for kids and families. "
    0
    Flag
  • Amani R.
    "We have a yearly block party at each of the local parks. They are usually well attended and snacks are provided. "
    0
    Flag
  • Gchekas
    "Short commute, less than five minutes to work. Lot of industry on Day Hill Road, plenty of work for manufacturing industry. "
    0
    Flag

LGBTQ Local Legal Protections

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Frequently asked questions about 37 Pilgrim Drive

  • What is 37 Pilgrim Drive estimated to be worth?
    Trulia's estimated value for 37 Pilgrim Drive in Windsor, CT is $465,100.
  • What is the price history for 37 Pilgrim Drive?
    37 Pilgrim Drive in Windsor, CT last sold for $465,000 in September 2026.
  • Is Windsor a buyer's or seller's market?
    Windsor is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Windsor?
    The median sale price in Windsor is $398K. That is up $38.17K from the prior month.
  • Does 37 Pilgrim Drive have air conditioning?
    Yes, 37 Pilgrim Drive in Windsor, CT has air conditioning.
  • Does 37 Pilgrim Drive have laundry facilities?
    Yes, 37 Pilgrim Drive in Windsor, CT has laundry facilities.

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