88 Overlook Dr, Windsor, CT 06095
Property image
Property image
OFF MARKET

$463,200

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,125 sqft (on 0.58 acres)

88 Overlook Dr, Windsor, CT 06095

Est. Refi. Payment $3,276/mo*
Refinance Your Home
Currently Off Market - Sold May 29, 2020 for $275,000

Home Value

Trulia Estimate
$463K
Since last month
Increased$3K (+0.7%)
Since last year
Increased$10K (+2.2%)
Since last sale
Increased$188K (+68.3%)
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 +87% in the last 10 years
MonthEstimated value
2026
August 2026$463K
July 2026$460K
June 2026$471K
May 2026$471K
April 2026$454K
March 2026$447K
February 2026$426K
January 2026$428K
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
105 Trent Drive, Windsor, CT
0.21
Single-Family Home
$420,000
04/15/26
4
2.5
1,960
72 Brookview Road, Windsor, CT
0.33
Single-Family Home
$435,000
10/10/25
4
3
2,660
45 Long Hill Road, Windsor, CT
0.44
Single-Family Home
$425,000
09/08/25
4
2.5
2,040
97 Brookview Road, Windsor, CT
0.47
Single-Family Home
$425,000
05/29/26
3
3
1,990
21 Long Hill Road, Windsor, CT
0.51
Single-Family Home
$440,000
11/21/25
3
2.5
2,264
123 Dudley Town Rd, Windsor, CT
0.59
Single-Family Home
$180,000
05/26/26
4
2
1,630
281 Mountain Road, Windsor, CT
0.44
Single-Family Home
$230,000
09/12/25
3
1.5
1,144
170 Dudley Town Road, Windsor, CT
0.56
Single-Family Home
$382,000
10/30/25
4
2
1,645
20 Ezra Silva Lane, Windsor, CT
0.65
Single-Family Home
$375,000
07/29/26
3
2
1,746
1060 Poquonock Ave, Windsor, CT
0.90
Single-Family Home
$400,000
05/04/26
4
2
1,873

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
118 Long Hill Road, Windsor, CT 06095
0.20
$509,500
3
2.5
2,308
Off Market
696 Bloomfield Avenue, Windsor, CT 06095
0.16
$370,400
3
2
1,950
Off Market
690 Bloomfield Avenue, Windsor, CT 06095
0.16
$399,300
3
1.5
1,350
Off Market
106 Long Hill Road, Windsor, CT 06095
0.23
$490,100
4
2.5
1,840
Off Market
105 Trent Drive, Windsor, CT 06095
0.21
$420,000
4
2.5
1,960
Recently Sold
55 Trent Drive, Windsor, CT 06095
0.21
$478,300
4
2.5
2,162
Off Market
93 Long Hill Road, Windsor, CT 06095
0.28
$464,600
3
3
1,999
Off Market
19 Mohawk Circle, Windsor, CT 06095
0.29
$509,300
4
2.5
2,062
Off Market
606 Bloomfield Avenue, Windsor, CT 06095
0.25
$369,100
3
2
2,220
Off Market
15 Stratford Court, Windsor, CT 06095
0.28
$446,200
4
2.5
2,056
Off Market
5 Stratford Court, Windsor, CT 06095
0.28
$428,500
3
2
1,976
Off Market
25 Stratford Court, Windsor, CT 06095
0.30
$446,000
4
1.5
1,882
Off Market

Local Information

  • Map ViewExplore the area around 88 Overlook Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1965
Lot Size
0.58 acres
Living Area
2,125 sqft
Price/Sqft
$218
Parking
Garage

About this House

Welcome home! This one owner 4-bedroom, 2.5 bath colonial-style home has been meticulously maintained, freshly painted in a neutral palette & is ready for a new owner. Major improvements include: Roof - 8/2019, 2-zone Buderus Gas Boiler - 11/2011, Gas Hot water heater - 2016, new hatchway - 2018, Leaf Guard Gutters, vinyl replacement thermal pane windows, updated kitchen w/cherry cabinets, tile backsplash, ample counter spaces, & garden window, remodeled powder room w/pedestal sink & vinyl plank flooring, and remodeled 2nd fl hall full bath w/new vanity, sink, & vinyl plank flooring. Sunlight bathes this lovely home with natural light reflecting off the gleaming, newly refinished hardwood floors. The wood burning fireplace in the generous-sized living room provides ambiance & warmth on chilly evenings. Chair rail adds character to the traditional dining room. Completing the main level is a den/office with ceiling fan, bay window, wall A/C, & entrances to both the oversized 2-car garage & backyard. On the 2nd fl is the front to back master bedroom with walk-in closet, ceiling fan, & full bath, plus 3 additional spacious bedrooms. The unfinished basement offers a double tub sink, great storage space & future potential for a rec room or man-cave. Conveniently located in CT's oldest town, in a neighborhood setting, within minutes of I-91, I-291, Windsor Center, shopping, restaurants, parks, & more.
88 Overlook Dr, Windsor, CT 06095 is a 4 bedroom, 3 bathroom, 2,125 sqft single-family home built in 1965. It last sold for $275,000 on May 29, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $463,200, with a rent estimate of $3,132/month.

Home Details for 88 Overlook Dr

Interior Features

Heating & Cooling
Heating: Baseboard, GasAir ConditioningCooling System: WallHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1965
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.58 acres

Price and Tax history

DateEventPrice
May 29, 2020
Source: Smart MLS #170284401
Sold
$275,000
Mar 28, 2020
Source: Agent Provided
Listed For Sale
$280,900

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

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 "
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  • Amy C.
    "Windsor is a town with strong resources and traditions. It has reasonable housing prices and lots of diversity. "
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  • Carol J. M.
    "We have coffee 9am - 11am once a month and other social events. Dog friendly. Neighbors are very friendly."
    0
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  • 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
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  • Amani R.
    "We have a yearly block party at each of the local parks. They are usually well attended and snacks are provided. "
    0
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  • Gchekas
    "Short commute, less than five minutes to work. Lot of industry on Day Hill Road, plenty of work for manufacturing industry. "
    0
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LGBTQ Local Legal Protections

Frequently asked questions about 88 Overlook Dr

  • What is 88 Overlook Dr estimated to be worth?
    Trulia's estimated value for 88 Overlook Dr in Windsor, CT is $463,200.
  • What is the price history for 88 Overlook Dr?
    88 Overlook Dr in Windsor, CT last sold for $275,000 in May 2020.
  • 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 $343K. That is up $7.33K from the prior month.
  • Does 88 Overlook Dr have air conditioning?
    Yes, 88 Overlook Dr in Windsor, CT has air conditioning.
  • Does 88 Overlook Dr have laundry facilities?
    Yes, 88 Overlook Dr in Windsor, CT has in-unit laundry.

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