37 Pilgrim Drive, Windsor, CT 06095
Property image
Property image
FOR SALE
NEW - 1 DAY AGO
0.8 ACRES

37 Pilgrim Drive
Windsor, CT 06095

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

$455,000

Est. Mortgage $3,224/mo*
Get Pre-Qualified

$455,000

Est. Mortgage $3,224/mo*
Get Pre-Qualified
4 Beds
2 Baths
1,886 sqft
(on 0.80 acres)

Home Highlights

Parking
2 Car Garage
Outdoor
Patio
Climate Control
Heating & Cooling
Price/Sqft
$241
Listed
1 day ago

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

About this House

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!

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

Days on Market

Days on Market: 1

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: $241
Status Change & Dates
Possession Timing: Immediately

Active Status

MLS Status: Active

Location

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

Agent Information

Listing Agent
Listing ID: 24197082

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
Last check for updates: about 4 hours ago
Listing courtesy of Andrea Rodriguez, (860) 331-5156
Eagle Eye Realty PLLC, (860) 331-5156
Source: Smart MLS, MLS#24197082
Also Listed on Smart MLS.

Market trends in Windsor

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$343K
$7.33KMoM
Sale-to-List Price
102.7%
Price per sq ft
$211
$3MoM
Available listings
44
16MoM

Price and Tax history

DateEventPrice
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
May 24, 2026
Source: Smart MLS #24159289
Listed For Sale
$329,900

Similar Homes You May Like

Skip to last item
Skip to first item

New Listings near 37 Pilgrim Drive

Skip to last item
Skip to first item

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
15 Pilgrim Drive, Windsor, CT
0.10
Single-Family Home
$310,000
09/22/25
4
2
1,981
36 Pilgrim Drive, Windsor, CT
0.03
Single-Family Home
$410,000
05/28/26
4
2
1,526
14 Alden Road, Windsor, CT
0.22
Single-Family Home
$410,000
10/15/25
4
1.5
2,515
29 Ravine Road, Windsor, CT
0.34
Single-Family Home
$395,000
09/18/25
4
2.5
1,944
86 Carriage Way, Windsor, CT
0.18
Single-Family Home
$550,000
07/22/26
4
2.5
2,926
40 Alden Road, Windsor, CT
0.36
Single-Family Home
$340,000
02/20/26
4
3
2,110
108 Pilgrim Drive, Windsor, CT
0.28
Single-Family Home
$445,000
08/26/25
3
3
2,037
608 Kennedy Road, Windsor, CT
0.48
Single-Family Home
$426,000
03/31/26
4
2
1,399

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
36 Pilgrim Drive, Windsor, CT 06095
0.03
$410,000
4
2
1,526
Recently Sold
38 Glenwood Drive, Windsor, CT 06095
0.09
$471,200
4
2.5
1,864
Off Market
15 Pilgrim Drive, Windsor, CT 06095
0.10
$327,400
4
2
1,981
Off Market
16 Pilgrim Drive, Windsor, CT 06095
0.09
$415,800
3
2.5
1,612
Off Market
75 Pilgrim Drive, Windsor, CT 06095
0.16
$378,600
3
1.5
1,128
Off Market
8 Drummer Drive, Windsor, CT 06095
0.16
$527,300
4
2.5
2,362
Off Market
98 Glenwood Drive, Windsor, CT 06095
0.17
$394,600
3
1.5
1,868
Off Market
83 Glenwood Drive, Windsor, CT 06095
0.18
$437,500
3
1.5
1,328
Off Market
86 Carriage Way, Windsor, CT 06095
0.18
$550,000
4
2.5
2,926
Recently Sold
51 Yorkshire Lane, Windsor, CT 06095
0.17
$433,600
3
2.5
1,600
Off Market
86 Glenwood Drive, Windsor, CT 06095
0.20
$395,100
3
1.5
1,591
Off Market

Around this home

What Locals Say about Windsor

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
    Flag
  • 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

Frequently asked questions about 37 Pilgrim Drive

  • What is the estimated monthly payment for 37 Pilgrim Drive?
    Based on a $455,000 list price with 20% down at today's rates, the estimated monthly payment for 37 Pilgrim Drive in Windsor, CT is approximately $3,263 (about $2,369 principal & interest, $819 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 37 Pilgrim Drive compare to homes in Windsor?
    37 Pilgrim Drive in Windsor, CT is listed at $455,000, about 33% above the $343K median sale price in Windsor.
  • What do residents say about Windsor?
    Residents describe Windsor, CT as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See homes for sale in Windsor, CT.
  • What are the closest schools to 37 Pilgrim Drive?
    The closest schools to 37 Pilgrim Drive in Windsor, CT are John F. Kennedy School (Elementary, rated 4/10), Oliver Ellsworth School (Pre-K/Elementary), Sage Park Middle School (rated 6/10).
  • 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.
Andrea Rodriguez, Eagle Eye Realty PLLC, (860) 331-5156
Agent Phone: (860) 331-5156
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.
37 Pilgrim Drive, Windsor, CT 06095 is a 4 bedroom, 2 bathroom, 1,886 sqft single-family home built in 1959. This property is currently available for sale and was listed by Smart MLS on Aug 15, 2026. The MLS # for this home is MLS# 24197082.