27 Orchard Rd, Windsor, CT 06095
OFF MARKET

27 Orchard Rd
Windsor, CT 06095

  • 3 Beds
  • 4.5 Baths
  • 3,552 sqft (on 4.10 acres)

$659,500

Trulia Estimate
as of Jun 24, 2026
Est. Refi. Payment $4,569/mo*
Refinance Your Home

$659,500

Trulia Estimate
as of Jun 24, 2026
Est. Refi. Payment $4,569/mo*
Refinance Your Home
3 Beds
4.5 Baths
3,552 sqft
(on 4.10 acres)

Local Information

  • Map ViewExplore the area around 27 Orchard Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

RARELY AVAILABLE Do not miss the opportunity to call one of the most beautiful locations on ORCHARD ROAD home Situated on a 4+ acre culdesac lot, this well-designed home is located within walking distance to Windsor Center's shops, restaurants and schools. Thoughtfully designed to showcase the pristine eastern views, the home features a flexible floor plan. Gather with family and friends in the in the living room w/fireplace or family room w/ vaulted ceiling, fireplace and custom built-ins look that opens to the expansive deck. Retire to the1st floor primary suite and enjoy the cathedral ceilings, two over-sized walk-in closets and two generously appointed bathrooms. The main level of the home offers a home office with built-in bookcases, laundry room off the kitchen, mudroom and a laundry closet in the primary suite. Step upstairs and find a spacious bedroom w/ensuite bathroom, bedroom with access to a walk-up attic, study w/closet and full bathroom. Watch the sun rise over the horizon as you enjoy your morning coffee in the sunroom. The setting of the home is truly spectacular and cannot be fully appreciated with photos as it is perched on a gently rolling hill, and one can see for miles. Lovingly maintained, the home offers hardwood floors, central ac (2012, multi-zoned heat, is wired for a generator, newer roof (2014 and many newer windows. Ideally located with easy access to RT 91 and the Greater Hartford area, this home has tremendous potential
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 27 Orchard Rd

Interior Features

Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Interior Details
Number of Rooms: 9
Appliances & Utilities
Washer
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1920
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 4.10 acres

Price History for 27 Orchard Rd

DatePriceEventSource
05/05/2023$500,000Sold
Smart MLS #170557831
05/01/2023$499,000PendingBerkshire Hathaway HomeServices New England Properties #170557831
03/29/2023$499,000ContingentBerkshire Hathaway HomeServices New England Properties #170557831
03/23/2023$499,000Listed For SaleSmart MLS #170557831
04/07/1987$259,000Sold
N/A

Market trends in Windsor

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
63
27MoM
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Property Tax and Assessment

Year2025
Tax$9,840
Assessment$345,870
Home facts updated by county records

Comparable Sales for 27 Orchard Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1123 Windsor Avenue, Windsor, CT
0.30
Single-Family Home
$550,000
07/01/25
5
3
3,439
24 Valley View Drive, Windsor, CT
0.42
Single-Family Home
$352,000
04/08/26
4
3.5
2,280
28 Maude Circle, Windsor, CT
0.44
Single-Family Home
$420,000
02/27/26
3
2
2,298
5 Ashley Road, Windsor, CT
0.50
Single-Family Home
$495,000
06/05/26
4
2.5
1,960
119 Joshua Hill, Windsor, CT
0.49
Single-Family Home
$390,000
01/09/26
3
2
2,080
60 Joshua Hl, Windsor, CT
0.46
Single-Family Home
$455,000
04/30/26
4
3
1,936
63 Ludlow Rd, Windsor, CT
0.48
Single-Family Home
$617,000
06/03/26
3
2
1,581
18 Giddings Avenue, Windsor, CT
0.45
Single-Family Home
$385,000
02/05/26
3
1.5
1,604
54 Amanda Cir, Windsor, CT
0.58
Single-Family Home
$445,000
12/04/25
3
3
1,632
110 Woodland Street, Windsor, CT
0.72
Single-Family Home
$405,000
06/05/26
3
2
2,190

Nearby homes

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Assigned Schools

These are the assigned schools for 27 Orchard Rd.
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
    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
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  • Sarah L.
    "Poquonock school is a wonderful community all the parks are very safe and the parks & rec programs are great"
    0
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  • 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
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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
    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
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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 "
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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
    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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Homes for sale near 27 Orchard Rd

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Off Market Homes Near 27 Orchard Rd

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27 Orchard Rd, Windsor, CT 06095 is a 3 bedroom, 5 bathroom, 3,552 sqft single-family home built in 1920. This property is not currently available for sale. 27 Orchard Rd was last sold on May 5, 2023 for $500,000. The current Trulia Estimate for 27 Orchard Rd is $659,500.