111 Pleasant St, Windsor, CT 06095
OFF MARKET

$492,900

Trulia Estimate
  • 2 Beds
  • 1 Bath
  • 1,000 sqft

111 Pleasant St, Windsor, CT 06095

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Home Value

Trulia Estimate
$493K
Since last month
Increased$4K (+0.7%)
Since last year
Decreased$3K (-0.6%)
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 +1% in the last 10 years
MonthEstimated value
2026
September 2026$493K
August 2026$489K
July 2026$481K
June 2026$488K
May 2026$484K
April 2026$466K
March 2026$471K
February 2026$479K
January 2026$473K
2025
2024

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 Clubhouse Road, Windsor, CT
0.26
Multi-Family Home
$380,000
12/19/25
4
2
1,768
44 Maple Avenue, Windsor, CT
0.47
Multi-Family Home
$374,000
05/22/26
3
2
1,554
40 Prospect Street, Windsor, CT
0.28
Multi-Family Home
$470,000
07/04/26
6
2
2,287
30 Prospect Street, Windsor, CT
0.31
Multi-Family Home
$430,000
09/26/25
6
2
2,514
26 Stinson Place, Windsor, CT
0.80
Multi-Family Home
$475,000
12/19/25
6
2.5
2,940
887 Poquonock Avenue, Windsor, CT
1.71
Multi-Family Home
$420,000
12/12/25
3
2.5
2,320
322 Deerfield Road, Windsor, CT
2.19
Multi-Family Home
$450,000
11/07/25
5
2
2,709
892-894 Main Street, South Windsor, CT
2.57
Multi-Family Home
$499,900
06/10/26
4
3
3,680
204 Oak Ridge Dr, Windsor Locks, CT
3.26
Multi-Family Home
$338,000
07/21/26
2
2
1,450
23 Lyme Street, Windsor, CT
3.05
Multi-Family Home
$425,000
09/23/26
5
2
2,329

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
Address Not Disclosed, South Windsor, CT 06074
0.02
$168,900
1
1
866
Off Market
160 Pleasant Street, Windsor, CT 06095
0.12
$281,600
4
2
2,144
Off Market
32 East Street, Windsor, CT 06095
0.18
$500,600
4
3
2,304
Off Market
49 Prospect Street, Windsor, CT 06095
0.25
$446,600
5
2.5
1,999
Off Market
124 East Street, Windsor, CT 06095
0.23
$326,200
2
1
1,288
Off Market
1 Gaylord Street, Windsor, CT 06095
0.25
$314,800
2
1
1,155
Off Market
Address Not Disclosed, Broad Brook, CT 06016
0.28
$356,800
4
1.5
1,688
Off Market
Address Not Disclosed, Broad Brook, CT 06016
0.28
$268,400
2
1
1,078
Off Market
Address Not Disclosed, Broad Brook, CT 06016
0.28
$303,300
3
1
1,312
Off Market
Address Not Disclosed, Broad Brook, CT 06016
0.28
$494,800
3
2
2,040
Off Market
125 East Street, Windsor, CT 06095
0.25
$544,300
4
3
2,518
Off Market
9 Brown Avenue, Windsor, CT 06095
0.27
$290,000
3
2
1,329
Recently Sold

Local Information

  • Map ViewExplore the area around 111 Pleasant St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Multi-Family
Built in 1900
1,000 sqft
$493/sqft

About this House

1st floor apartment available now for immediate occupancy in a 4 family home near the center of town. Heat and hot water included in rent. Freshly painted and hardwood floors were just refinished. Dishwasher, electric stove, hood and refrigerator in kitchen. No laundry on premises. Agent and owner are related. Credit check is a must with good credit. We do not take exceptions. 2 months security deposit plus 1 month rent to move in.
111 Pleasant St, Windsor, CT 06095 is a 2 bedroom, 1 bathroom, 1,000 sqft multi-family built in 1900. More recently, it was listed as a rental in September 2017 with an asking price of $1,200 per month. That rental listing was removed on October 5, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $492,900, with a rent estimate of $1,638/month.

Home Details for 111 Pleasant St

Interior Features

Heating & Cooling
Heating: BaseboardHeating Fuel: Baseboard
Interior Details
Number of Rooms: 4
Appliances & Utilities
DishwasherRefrigerator

Property Information

Year Built
Year Built: 1900Year Updated: 1900
Property Type / Style
Property Type: Multi FamilyArchitecture: Colonial

Exterior Features

Parking & Garage
Parking: Off Street

Price and Tax history

DateEventPrice
Oct 5, 2017
Source: Agent Provided
ListingRemoved
$1,200
Sep 20, 2017
Source: Agent Provided
Listed For Rent
$1,200
Feb 16, 2017
Source: Agent Provided
ListingRemoved
$1,050
Jan 27, 2017
Source: Agent Provided
Listed For Rent
$1,050
Mar 1, 2016
Source: Agent Provided
ListingRemoved
$1,100

Market trends in Windsor

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
55
11MoM

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
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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

Frequently asked questions about 111 Pleasant St

  • What is 111 Pleasant St estimated to be worth?
    Trulia's estimated value for 111 Pleasant St in Windsor, CT is $492,900.
  • Is Windsor a buyer's or seller's market?
    Windsor is currently a seller's market, based on recent for-sale activity.
  • 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 recently sold homes in Windsor, CT.
  • What are the closest schools to 111 Pleasant St?
    The closest schools to 111 Pleasant St 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 111 Pleasant St have parking?
    Yes, 111 Pleasant St in Windsor, CT has on-site parking.

Explore by feature - Pet Friendly

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