101 Hillcrest Road, Windsor, CT 06095
OFF MARKET

101 Hillcrest Road
Windsor, CT 06095

  • 3 Beds
  • 2 Baths
  • 2,274 sqft (on 0.31 acres)

$471,100

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $3,347/mo*
Refinance Your Home

$471,100

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $3,347/mo*
Refinance Your Home
3 Beds
2 Baths
2,274 sqft
(on 0.31 acres)

Local Information

  • Map ViewExplore the area around 101 Hillcrest Road.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1927
Lot Size
0.31 acres
Living Area
2,274 sqft
Price/Sqft
$207
Parking
2 Car Garage

About this House

Nestled in a desirable neighborhood, this stunning four bedroom Colonial seamlessly blends elegance, timeless craftsmanship, modern updates and an air of sophistication that carries throughout the entire residence. A gorgeous kitchen boasts rich hardwood flooring, white cabinetry, quartz countertops, tile backsplash, stainless steel appliances, intricate crown molding and a pantry. Entertain your guests in the stylish dining room featuring a built-in hutch, crown molding, a chair rail and hardwood flooring. Relax with your guests in the expansive living room by the warmth of the wood burning fireplace, and revel in the beauty of the hardwood flooring and the refinement of the crown molding and the French door that leads to an inviting three season room. A half bath completes the first level. The second level presents a unique layout. One of the bedrooms is being used as an incredible den offering a beautiful fireplace and a half bath. There are three additional bedrooms, an updated full bath and an office for those who work from home. Unbeatable value is found in the recent upgrades which include natural gas heating, fresh interior and exterior paint, updated electrical, repointed chimney with a new liner, newer garage door and openers and backyard fencing. Imagine the endless fun in hosting summer barbecues in the spacious level yard-perfect for games, gatherings, gardening or relaxing in your picturesque outdoor oasis. Come on...Let's take a look inside!
101 Hillcrest Road, Windsor, CT 06095 is a 3 bedroom, 3 bathroom, 2,274 sqft single-family home built in 1927. It last sold for $436,000 on Mar 13, 2025 (6% above the $409,900 asking price). It is currently off market. The Trulia Estimate is $471,100, with a rent estimate of $2,808/month.

Home Details for 101 Hillcrest Road

Interior Features

Interior Details
Basement: Full,Storage Space,Hatchway Access,Interior Entry,Partially FinishedNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Office, Rec Play Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 1Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 2274 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Oven/Range, Refrigerator, Dishwasher, Disposal, Gas Water Heater, Water HeaterDishwasherDisposalLaundry: Lower LevelRefrigerator
Heating & Cooling
Heating: Radiator,Natural GasHas CoolingAir Conditioning: Ceiling Fan(s)Has HeatingHeating Fuel: Radiator
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane WindowsDoor: Storm Door(s)

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Enclosed, PorchFencing: Wood, FullExterior: Sidewalk, Rain GuttersFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Attached,Paved,Driveway,Garage Door Opener,Asphalt
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2274 Square Feet

Property Information

Year Built
Year Built: 1927
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Shingle Siding, CedarNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 778329

Price & Status

Price
List Price: $409,900
Status Change & Dates
Off Market Date: Tue Feb 18 2025Possession Timing: Negotiable

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: Windsor
School Information
Elementary School: Per Board of EdJr High / Middle School: Sage ParkHigh School: Windsor

Building

Building Area
Building Area: 2274 Square Feet

Community

Community Features: Library, Park, Playground, Public Rec Facilities, Shopping/Mall, Tennis Court(s), Near Public Transport
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 0.31 acres

Energy

Energy Efficiency Features: Thermostat, Doors, Windows

Miscellaneous

BasementMls Number: 24070597Attic: Storage, Floored, Walk-upAbove Grade Unfinished Area: 2274

Additional Information

LibraryParkPlaygroundPublic Rec FacilitiesShopping/MallTennis Court(s)Near Public Transport
Last check for updates: about 1 hour ago
Listed by Sharon D. Rispoli, (860) 205-9316
Berkshire Hathaway NE Prop., (860) 688-7531
Bought with: Diane McDougald, (860) 833-0791, Berkshire Hathaway NE Prop., (860) 688-7531
Source: Smart MLS, MLS#24070597

Price History for 101 Hillcrest Road

DatePriceEventSource
03/13/2025$436,000Sold
Smart MLS #24070597
02/18/2025$409,900PendingSmart MLS #24070597
02/13/2025$409,900Listed For SaleSmart MLS #24070597
06/29/2016$200,000Sold
Smart MLS #G10099789
05/20/2016$209,900PendingAgent Provided
05/20/2016$209,900Listed For SaleAgent Provided
03/28/2016$209,900ListingRemovedAgent Provided
03/25/2016$209,900PendingAgent Provided
03/08/2016$209,900PriceChange
Agent Provided
12/21/2015$219,900Listed For SaleAgent Provided
11/24/1998$175,000Sold
N/A
05/22/1991$170,000Sold
N/A

Market trends in Windsor

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$336K
$27.63KMoM
Sale-to-List Price
—
Price per sq ft
$214
$3MoM
Available listings
60
3MoM
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Property Tax and Assessment

Year2025
Tax$7,787
Assessment$273,700
Home facts updated by county records

Comparable Sales for 101 Hillcrest Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14 Sage Park Road, Windsor, CT
0.05
Single-Family Home
$338,000
02/09/26
3
2
1,578
20 Sage Park Road, Windsor, CT
0.04
Single-Family Home
$300,000
11/26/25
3
1.5
1,495
10 Harvey Road, Windsor, CT
0.14
Single-Family Home
$436,000
06/26/26
4
1.5
2,548
94 Ludlow Road, Windsor, CT
0.34
Single-Family Home
$385,000
05/21/26
3
2
1,578
49 Remington Road, Windsor, CT
0.39
Single-Family Home
$360,000
08/29/25
3
1.5
1,741
28 Maude Circle, Windsor, CT
0.44
Single-Family Home
$420,000
02/27/26
3
2
2,298
3 Maude Circle, Windsor, CT
0.47
Single-Family Home
$342,000
12/30/25
3
1.5
1,639
145 Park Avenue, Windsor, CT
0.27
Single-Family Home
$350,000
01/15/26
3
2.5
1,189
11 Fyler Drive, Windsor, CT
0.20
Single-Family Home
$345,000
04/28/26
3
1
1,094

Nearby homes

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Assigned Schools

These are the assigned schools for 101 Hillcrest Road.
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 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
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  • 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
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  • Shyra E.
    "My neighborhood is amazing it has good transit access and wonderful restaurants and parks hope this helps"
    0
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  • 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
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  • 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
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  • 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
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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
    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
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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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Apartments for Rent

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Explore by feature - Pet Friendly

7 pet-friendly rentals in Windsor, CT

Explore by feature - Air Conditioning

9 rentals with air conditioning in Windsor, CT

Explore by feature - Washer/dryer

12 rentals with a washer/dryer in Windsor, CT

Homes for sale near 101 Hillcrest Road

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Off Market Homes Near 101 Hillcrest Road

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Frequently asked questions about 101 Hillcrest Road

  • What is 101 Hillcrest Road estimated to be worth?
    Trulia's estimated value for 101 Hillcrest Road in Windsor, CT is $471,100.
  • What is the price history for 101 Hillcrest Road?
    101 Hillcrest Road in Windsor, CT last sold for $436,000 in March 2025.
  • 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 $336K. That is down $27.63K from the prior month.
  • Does 101 Hillcrest Road have air conditioning?
    Yes, 101 Hillcrest Road in Windsor, CT has air conditioning.
  • Does 101 Hillcrest Road have laundry facilities?
    Yes, 101 Hillcrest Road in Windsor, CT has laundry facilities.
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.