65 Hilltop Road, Windsor, CT 06095
OFF MARKET

65 Hilltop Road
Windsor, CT 06095

  • 2 Beds
  • 2 Baths
  • 1,128 sqft (on 0.58 acres)

$345,900

Trulia Estimate
as of Jul 12, 2026
Est. Refi. Payment $2,431/mo*
Refinance Your Home

$345,900

Trulia Estimate
as of Jul 12, 2026
Est. Refi. Payment $2,431/mo*
Refinance Your Home
2 Beds
2 Baths
1,128 sqft
(on 0.58 acres)

Local Information

  • Map ViewExplore the area around 65 Hilltop Road.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Discover the perfect blend of charm, modern updates, and serene surroundings in this beautifully updated two-bedroom, two-bathroom cottage tucked away on a private cul-de-sac. Nestled near the Farmington River and just moments from the Rainbow Reservoir boat launch, this home offers a peaceful retreat with the convenience of nearby shopping, dining, and major commuter routes. Step inside to find a thoughtfully updated interior featuring stylish finishes, and an abundance of natural light. The renovated kitchen boasts modern appliances, a cozy dining area, and plenty of flexible space. The spacious primary suite includes an ensuite bath with washer & dryer, while the second bedroom provides flexibility for guests or a home office. Outside, the picturesque lot offers a tranquil setting with mature trees, grape arbor, space for gardens, and room to relax or entertain. Whether you're enjoying the peaceful ambiance from your porch or heading out for a day of boating, fishing, or hiking, this home is a true hidden gem that brings together the best of country living with city convenience. Don't miss this rare opportunity-schedule your showing today!
65 Hilltop Road, Windsor, CT 06095 is a 2 bedroom, 2 bathroom, 1,128 sqft single-family home built in 1935. It last sold for $320,000 on May 9, 2025 (9% above the $294,900 asking price). It is currently off market. The Trulia Estimate is $345,900, with a rent estimate of $2,371/month.

Home Highlights

Parking
Open Parking
Outdoor
Yes
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 65 Hilltop Road

Interior Features

Interior Details
Basement: Partial,Dirt FloorNumber of Rooms: 5Types of Rooms: Master Bedroom, Bedroom, Dining Room, Living Room
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1128 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Upper LevelRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,ElectricNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
No Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: CoveredOther Structures: Shed(s)Exterior: Garden, Stone WallFoundation: MasonryGardenNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 4Parking: None,Paved,Off Street,Driveway,Private
Frontage
Waterfront: Walk to WaterNot on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 1128 Square Feet

Property Information

Year Built
Year Built: 1935
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Bungalow
Building
Construction Materials: Shake Siding, ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 770951

Price & Status

Price
List Price: $294,900
Status Change & Dates
Off Market Date: Thu May 01 2025Possession Timing: Flexible

Active Status

MLS Status: Closed

Location

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

Building

Building Area
Building Area: 1128 Square Feet

Community

Community Features: Near Public Transport, Golf, Public Rec Facilities

HOA

No HOA

Lot Information

Lot Area: 0.58 acres

Miscellaneous

BasementMls Number: 24084183Attic: Access Via HatchAbove Grade Unfinished Area: 1128

Additional Information

Near Public TransportGolfPublic Rec Facilities
Last check for updates: about 5 hours ago
Listed by Juli L. Rogalla, (860) 558-2145
Coldwell Banker Realty, (860) 668-4589
Bought with: Laura Beth Collinson, (860) 262-2753, Carl Guild & Associates, (860) 474-3500
Source: Smart MLS, MLS#24084183

Price History for 65 Hilltop Road

DatePriceEventSource
05/09/2025$320,000Sold
Smart MLS #24084183
03/29/2025$294,900Listed For SaleSmart MLS #24084183
03/02/2005$93,000Sold
Smart MLS #G362008

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$3,955
Assessment$139,020
Home facts updated by county records

Comparable Sales for 65 Hilltop Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
16 Hilltop Road, Windsor, CT
0.09
Single-Family Home
$425,000
04/02/26
3
2
1,715
87 Hilltop Road, Windsor, CT
0.03
Single-Family Home
$397,000
02/13/26
3
2
1,856
56 Birchwood Road, Windsor, CT
0.29
Single-Family Home
$375,000
09/10/25
3
2.5
1,975
908 Stone Road, Windsor, CT
0.63
Single-Family Home
$330,000
09/26/25
3
1.5
1,493
14 Loren Circle, Windsor, CT
0.67
Single-Family Home
$385,000
01/23/26
3
2.5
1,942
20 Sweetbrier Road, East Granby, CT
0.99
Single-Family Home
$360,000
10/24/25
3
2
1,470
220 Castlewood, Windsor, CT
0.89
Single-Family Home
$370,500
01/07/26
3
1.5
1,484
92 Spoonville Road, East Granby, CT
1.06
Single-Family Home
$305,000
11/14/25
3
2
1,244
552 Stone Road, Windsor, CT
0.85
Single-Family Home
$300,000
01/16/26
3
1
1,128
158 Winterwood, Windsor, CT
0.86
Single-Family Home
$406,000
11/12/25
3
2.5
1,894

Nearby homes

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Assigned Schools

These are the assigned schools for 65 Hilltop 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

  • 78 % Say yards are well-kept

  • 74 % Say people would walk alone at night

  • 70 % Say there's holiday spirit

  • 69 % Say it's quiet

  • 68 % Say there's wildlife

  • 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
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  • 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
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  • 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
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  • Sam B.
    "Great place to live grow work Bus and Uber available Mixed crowd Friendly people Great schools Parks pools Best library "
    0
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  • 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
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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
    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
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  • 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
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  • 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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9 rentals with air conditioning in Windsor, CT

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Homes for sale near 65 Hilltop Road

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Off Market Homes Near 65 Hilltop Road

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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.