Is a car needed in Windsor, CT?

As of early 2026, 89% of users say car is needed

Is parking easy in Windsor, CT?

As of early 2026, 88% of users say parking is easy

Is Windsor, CT dog-friendly?

As of early 2026, 87% of users say it's dog friendly

Are the streets well-lit in Windsor, CT?

As of early 2026, 78% of users say streets are well-lit

Are yards well-kept in Windsor, CT?

As of early 2026, 78% of users say yards are well-kept

Would people walk alone at night in Windsor, CT?

As of early 2026, 74% of users say people would walk alone at night

Does Windsor, CT show holiday spirit?

As of early 2026, 70% of users say there's holiday spirit

Is Windsor, CT quiet?

As of early 2026, 69% of users say it's quiet

Is there wildlife in Windsor, CT?

As of early 2026, 68% of users say there's wildlife

Does Windsor, CT have sidewalks?

As of early 2026, 67% of users say there are sidewalks

Do kids play outside in Windsor, CT?

As of early 2026, 65% of users say kids play outside

Are neighbors friendly in Windsor, CT?

As of early 2026, 55% of users say neighbors are friendly

Do residents of Windsor, CT plan to stay at least 5 years?

As of early 2026, 53% of users say they plan to stay for at least 5 years

Is Windsor, CT walkable to restaurants?

As of early 2026, 46% of users say it's walkable to restaurants

Is Windsor, CT walkable to grocery stores?

As of early 2026, 46% of users say it's walkable to grocery stores

Are there community events in Windsor, CT?

As of early 2026, 34% of users say there are community events

ACCEPTING BACKUPS

0.72 ACRES

249 Preston Street
Windsor, CT 06095

3 Beds
2 Baths
1,156 sqft (on 0.72 acres)

$332,000

Est. Mortgage $2,338/mo*

Get Pre-Qualified

$332,000

Est. Mortgage $2,338/mo*

Get Pre-Qualified

3 Beds

2 Baths

1,156 sqft

(on 0.72 acres)

We estimate this home will sell faster than 89% nearby.

Local Information

Map ViewExplore the area around 249 Preston Street.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

Nestled on a quiet cul-de-sac in Windsor, this charming raised ranch offers the perfect blend of privacy and convenience, situated just moments away from local schools. The home features a bright, open-concept main level with a modern kitchen boasting granite countertops, stylish copper pendant lighting, and an expansive wall of custom cabinetry for incredible storage. Sliding glass doors lead out to a generous deck, overlooking a sprawling, level backyard that is ideal for outdoor activities or gardening. With a versatile layout, a clean and updated aesthetic, and a prime location for families, this property is a fantastic find for those seeking a move-in-ready home in a peaceful neighborhood setting.

We estimate this home will sell faster than 89% nearby.

Home Highlights

Parking

1 Car Garage

Outdoor

No Info

A/C

Heating & Cooling

HOA

None

Price/Sqft

$287

Listed

64 days ago

Home Details for 249 Preston Street

Interior Features
Interior Details Basement: Full,Partially FinishedNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom, Dining Room, Living Room
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout Living Area: 1156 Square Feet
Appliances & Utilities Appliances: Oven/Range, Refrigerator, Dishwasher, Gas Water Heater, Water HeaterDishwasherLaundry: Lower LevelRefrigerator
Heating & Cooling Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa No Fireplace
Levels, Entrance, & Accessibility Levels: Multi/Split

Exterior Features
Exterior Home Features Roof: AsphaltFoundation: Concrete PerimeterNo Private Pool
Parking & Garage Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 7Parking: Attached,Paved,Driveway,Private
Frontage Not on Waterfront
Water & Sewer Sewer: Public Sewer
Finished Area Finished Area (above surface): 1156 Square Feet

Days on Market
Days on Market: 64

Property Information
Year Built Year Built: 1957
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Split Level
Building Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information Parcel Number: 778400

Price & Status
Price List Price: $332,000Price Per Sqft: $287
Status Change & Dates Possession Timing: Negotiable

Active Status
MLS Status: Under Contract - Continue to Show

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

Agent Information
Listing Agent Listing ID: 24168864

Building
Building Area Building Area: 1156 Square Feet

HOA
No HOA

Lot Information
Lot Area: 0.72 acres

Miscellaneous
BasementMls Number: 24168864Zillow Contingency Status: Accepting Back-up OffersAttic: NoneAttribution Contact: (860) 480-0643Above Grade Unfinished Area: 1156

Last check for updates: about 18 hours ago

Listing courtesy of Michelle Grant, (860) 480-0643

Coldwell Banker Premier Real Estate, (860) 480-0643

Source: Smart MLS, MLS#24168864

Also Listed on Smart MLS.

Market trends in Windsor

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

27MoM

Price History for 249 Preston Street

Date	Price	Event	Source
04/21/2026	$332,000	Listed For Sale	Smart MLS #24168864

03/12/2010	$235,000	Sold	N/A
Recording Date 03/12/2010 County Transfer Tax N/A Total Transfer Tax N/A
12/05/2009	$249,900	Listed For Sale	Agent Provided

05/20/2003	$168,000	Sold	Smart MLS #G309025
Recording Date 05/20/2003 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$6,012
Assessment	$211,330

Home facts updated by county records

Comparable Sales for 249 Preston Street

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
246 Preston Street, Windsor, CT	0.04	Single-Family Home	$435,500	08/08/25	5	2	1,243
97 Capen Street, Windsor, CT	0.15	Single-Family Home	$255,000	09/19/25	3	1.5	952
20 Sage Park Road, Windsor, CT	0.26	Single-Family Home	$300,000	11/26/25	3	1.5	1,495
14 Sage Park Road, Windsor, CT	0.26	Single-Family Home	$338,000	02/09/26	3	2	1,578
49 Remington Road, Windsor, CT	0.28	Single-Family Home	$360,000	08/29/25	3	1.5	1,741
60 Filley Street, Windsor, CT	0.50	Single-Family Home	$370,000	02/27/26	3	2	1,306
122 Capen Street, Windsor, CT	0.21	Single-Family Home	$350,000	06/01/26	3	1	1,525
11 Fyler Drive, Windsor, CT	0.43	Single-Family Home	$345,000	04/28/26	3	1	1,094
15 Moore Drive, Windsor, CT	0.36	Single-Family Home	$320,000	09/09/25	3	1	1,166

Nearby homes

Get a sense of prices in the area by checking nearby homes.

Skip to last item

OFF MARKET
Est. $458,800
5 bd
2 ba
1,243 sqft
246 Preston Street,
Windsor, CT 06095
William Raveis Real Estate
OFF MARKET
Est. $503,900
4 bd
2.5 ba
1,702 sqft
259 Preston Street,
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Coldwell Banker Realty
OFF MARKET
Est. $517,800
4 bd
2.5 ba
1,915 sqft
228 Preston Street,
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William Raveis Real Estate
OFF MARKET
Est. $437,800
3 bd
1.5 ba
1,595 sqft
295 Preston Street,
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New Door Realty
OFF MARKET
Est. $388,700
4 bd
1.5 ba
1,262 sqft
33 Capen Street,
Windsor, CT 06095
KW Legacy Partners
SOLD
SEP 19, 2025
$255,000
3 bd
1.5 ba
952 sqft
97 Capen Street,
Windsor, CT 06095
Century 21 AllPoints Realty
OFF MARKET
Est. $343,200
4 bd
1.5 ba
1,458 sqft
47 Capen Street,
Windsor, CT 06095
Century 21 AllPoints Realty
OFF MARKET
Est. $414,400
4 bd
1.5 ba
1,784 sqft
12 Harvey Road,
Windsor, CT 06095
Berkshire Hathaway NE Prop.
OFF MARKET
Est. $439,300
5 bd
3 ba
1,999 sqft
103 Capen Street,
Windsor, CT 06095
Realty One Group Cutting Edge
OFF MARKET
Est. $435,400
3 bd
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2,075 sqft
96 Capen Street,
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Berkshire Hathaway NE Prop.
OFF MARKET
Est. $391,600
3 bd
1 ba
1,627 sqft
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Berkshire Hathaway NE Prop.
OFF MARKET
Est. $424,800
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Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 249 Preston Street.

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
Resident
1y ago
"Quiet and everyone keeps to themselves. Only a little noisy during the summer time due to motorcycles."
0
Flag
Zonoui Smith Jr.
Resident
1y ago
"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
Resident
5y ago
"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
Resident
5y ago
"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
Resident
5y ago
"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
Resident
6y ago
"Lots of town activities! Stuff on the green, local businesses, small town feel! Diverse community and polite town members"
1
Flag
Unspecified
Resident
6y ago
"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.
Resident
6y ago
"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
Resident
6y ago
"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.
Resident
6y ago
"Poquonock school is a wonderful community all the parks are very safe and the parks & rec programs are great"
0
Flag
Sam B.
Resident
6y ago
"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.
Resident
6y ago
"Great place to live grow work Bus and Uber available Mixed crowd Friendly people Great schools Parks pools Best library "
0
Flag
Sam B.
Resident
6y ago
"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.
Resident
6y ago
"My neighborhood is amazing it has good transit access and wonderful restaurants and parks hope this helps"
0
Flag
Carol J. M.
Resident
6y ago
"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
Resident
6y ago
"Usually on the town green, farmers market, summer outdoor concerts, parades, Halloween event, holiday events, craft fairs"
0
Flag
Bonny E.
Resident
6y ago
"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.
Resident
6y ago
"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
Resident
6y ago
"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.
Resident
6y ago
"recreation Dept has great programs parks are well maintained school system is getting back on track great family friendly town"
0
Flag
Me
Resident
6y ago
"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.
Resident
6y ago
"during the summer they have concerts on the green down town. nice place tp live. quite contry living"
0
Flag
Me
Resident
6y ago
"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
Resident
7y ago
"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
Flag
Amy C.
Resident
7y ago
"Windsor is a town with strong resources and traditions. It has reasonable housing prices and lots of diversity. "
0
Flag
Carol J. M.
Resident
7y ago
"We have coffee 9am - 11am once a month and other social events. Dog friendly. Neighbors are very friendly."
0
Flag
Shanyelle.hamilton
Resident
7y ago
"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
Resident
7y ago
"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
Resident
7y ago
"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.
Resident
7y ago
"We have a yearly block party at each of the local parks. They are usually well attended and snacks are provided. "
0
Flag
Gchekas
Resident
7y ago
"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

Michelle Grant, Coldwell Banker Premier Real Estate, (860) 480-0643

Agent Phone: (860) 480-0643

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.

249 Preston Street, Windsor, CT 06095 is a 3 bedroom, 2 bathroom, 1,156 sqft single-family home built in 1957. This property is currently available for sale and was listed by Smart MLS on Apr 21, 2026. The MLS # for this home is MLS# 24168864.

249 Preston Street
Windsor, CT 06095

$332,000

$332,000

Local Information