39 Hillcrest Rd, Windsor, CT 06095
OFF MARKET

39 Hillcrest Rd
Windsor, CT 06095

  • 3 Beds
  • 2.5 Baths
  • 1,858 sqft

$503,100

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $3,554/mo*
Refinance Your Home

$503,100

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $3,554/mo*
Refinance Your Home
3 Beds
2.5 Baths
1,858 sqft

Home Value

Trulia Estimate
$503K
Since last month
$200 (0%)
Since last year
Increased$12K (+2.5%)
Since last sale
Increased$65K (+14.7%)
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 +119% in the last 10 years
MonthEstimated value
2026
August 2026$505K
July 2026$504K
June 2026$516K
May 2026$519K
April 2026$504K
March 2026$502K
February 2026$476K
January 2026$477K
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
14 Sage Park Road, Windsor, CT
0.14
Single-Family Home
$338,000
02/09/26
3
2
1,578
20 Sage Park Road, Windsor, CT
0.18
Single-Family Home
$300,000
11/26/25
3
1.5
1,495
94 Ludlow Road, Windsor, CT
0.34
Single-Family Home
$385,000
05/21/26
3
2
1,578
23 Ludlow Road, Windsor, CT
0.28
Single-Family Home
$430,000
08/03/26
4
2
1,832
18 Giddings Avenue, Windsor, CT
0.41
Single-Family Home
$385,000
02/05/26
3
1.5
1,604
28 Maude Circle, Windsor, CT
0.34
Single-Family Home
$420,000
02/27/26
3
2
2,298
10 Harvey Road, Windsor, CT
0.06
Single-Family Home
$436,000
06/26/26
4
1.5
2,548
145 Park Avenue, Windsor, CT
0.32
Single-Family Home
$350,000
01/15/26
3
2.5
1,189
3 Maude Circle, Windsor, CT
0.40
Single-Family Home
$342,000
12/30/25
3
1.5
1,639

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
4 Park Avenue, Windsor, CT 06095
0.04
$424,500
4
1.5
1,736
Off Market
12 Harvey Road, Windsor, CT 06095
0.07
$404,800
4
1.5
1,784
Off Market
10 Harvey Road, Windsor, CT 06095
0.06
$436,000
4
1.5
2,548
Recently Sold
1123 Windsor Avenue, Windsor, CT 06095
0.08
$585,000
5
3
3,439
Off Market
53 Park Avenue, Windsor, CT 06095
0.09
$478,500
3
2.5
1,680
Off Market
14 Sage Park Road, Windsor, CT 06095
0.14
$338,000
3
2
1,578
Recently Sold
1111 Windsor Avenue, Windsor, CT 06095
0.14
$319,600
3
1
1,396
Off Market
56 Wilton Road, Windsor, CT 06095
0.15
$399,700
3
1.5
1,688
Off Market
101 Hillcrest Road, Windsor, CT 06095
0.16
$471,100
3
2
2,274
Off Market
18 Orchard Road, Windsor, CT 06095
0.16
$553,300
3
3
2,308
Off Market
20 Sage Park Road, Windsor, CT 06095
0.18
$300,000
3
1.5
1,495
Recently Sold

Local Information

  • Map ViewExplore the area around 39 Hillcrest Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1929
Living Area
1,858 sqft
Price/Sqft
$271
Parking
Garage

About this House

Welcome to your dream home! This stunning English Colonial style gem offers a spacious 1858 sqft of pure comfort and charm, nestled in the heart of a serene neighborhood. With 3 cozy bedrooms and 2 1/2 chic bathrooms, this house perfectly marries modern convenience with timeless elegance. Step inside and let the beautiful hardwood flooring sweep you off your feet, adding a touch of warmth and character to every room! Need space? No problem! Ample closet space throughout means keeping things organized is a breeze. The kitchen? A total culinary paradise! Featuring sleek stainless steel appliances and a handy pantry, it's ready and waiting to inspire your inner chef. The living room is a haven of relaxation with a charming fireplace to gather around and create lasting memories. Bask in the natural light that floods each corner, enhancing the spacious feel and showcasing the thoughtful layout of your new home. A brand-new AC system ensures you stay comfy no matter the season! The fully finished basement is a versatile wonder, perfect for whatever your heart desires-be it a home office, a media haven, or your very own gym. Step outside to discover a beautifully landscaped, partially fenced-in yard that promises privacy and a slice of paradise. The back patio, accessible from a charming 3-season room adjacent to the formal dining area, is your new go-to spot for alfresco dining and relaxation. Plus, a 2-car garage for easy parking. Must see! You'll fall in love!
39 Hillcrest Rd, Windsor, CT 06095 is a 3 bedroom, 3 bathroom, 1,858 sqft single-family home built in 1929. It last sold for the $439,900 asking price on Aug 29, 2024. It is currently off market. The Trulia Estimate is $503,100, with a rent estimate of $2,972/month.
Last check for updates: about 23 hours ago
Listed by Mary Louise Wadsworth, (860) 930-7244
KW Legacy Partners, (860) 313-0700
Co-Listing Agent: Sandie Terenzi, (860) 761-3780
KW Legacy Partners, (860) 313-0700
Bought with: Diane Fahey, (203) 605-5098, Berkshire Hathaway NE Prop., (860) 621-6821
Source: Smart MLS, MLS#24019760

Home Details for 39 Hillcrest Rd

Interior Features

Interior Details
Basement: FullNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Dining Room, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1858 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher, Disposal, Washer, Dryer, Water HeaterDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Steam,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Steam
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltFencing: PartialFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageParking Spaces: 2Parking: Detached
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1858 Square Feet

Property Information

Year Built
Year Built: 1929
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 779081

Price & Status

Price
List Price: $439,900
Status Change & Dates
Off Market Date: Tue Jul 09 2024Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

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

Building

Building Area
Building Area: 1858 Square Feet

HOA

No HOA

Lot Information

Lot Area: 10018.8 sqft

Miscellaneous

BasementMls Number: 24019760Attic: Walk-upAbove Grade Unfinished Area: 1858

Price and Tax history

DateEventPrice
Aug 29, 2024
Source: Smart MLS #24019760
Sold
$440,000
Jun 26, 2024
Source: Smart MLS #24019760
Listed For Sale
$439,900
Jun 26, 2002
Source: N/A
Sold
$210,000
Jun 23, 1999
Source: N/A
Sold
$165,000
Jun 30, 1989
Source: N/A
Sold
$196,000

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 "
    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
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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
    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 39 Hillcrest Rd

  • What is 39 Hillcrest Rd estimated to be worth?
    Trulia's estimated value for 39 Hillcrest Rd in Windsor, CT is $503,100.
  • What is the price history for 39 Hillcrest Rd?
    39 Hillcrest Rd in Windsor, CT last sold for $440,000 in August 2024.
  • 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 39 Hillcrest Rd have air conditioning?
    Yes, 39 Hillcrest Rd in Windsor, CT has air conditioning.
  • Does 39 Hillcrest Rd have laundry facilities?
    Yes, 39 Hillcrest Rd in Windsor, CT has in-unit laundry.

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