55 Timothy Drive, Middletown, CT 06457
SOLD
JAN 9, 2026

55 Timothy Drive
Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 2,522 sqft

$400,000

Last Sold: Jan 9, 2026
1% below list $405K
$159/sqft
Est. Refi. Payment $2,729/mo*
Refinance Your Home

$400,000

Last Sold: Jan 9, 2026
1% below list $405K
$159/sqft
Est. Refi. Payment $2,729/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,522 sqft

Local Information

  • Map ViewExplore the area around 55 Timothy Drive.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Your dream home awaits just in time for the holidays! Situated towards the end of a cul-de-sac in the lovely Westfield section of Middletown, the location, home condition and offering price is without parallel in todays market! Stepping inside the front door, you're welcomed by a dramatic two story foyer that sets the tone for the size of every room. New vinyl plank flooring throughout most of the home, large eat-in kitchen that leads to back deck creating the perfect layout for entertaining. Going up to the second floor you'll notice an open floor plan with 2nd story foyer, three bedrooms all spacious in size and spread out. The primary suit offers a walk in closet, full bath with charming barn door entry and additional closet space. The fully finished basement provides a rec/media room totaling approx. 500sf and separate laundry room. This property will be an absolute delight to see for anyone looking in Westfield at this price-point
55 Timothy Drive, Middletown, CT 06457 is a 3 bedroom, 3 bathroom, 2,522 sqft single-family home built in 1991. It last sold for $400,000 on Jan 9, 2026 (1% below the $405,000 asking price). It is currently off market. The Trulia Estimate is $410,700, with a rent estimate of $3,237/month.

Home Highlights

Parking
2 Car Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
$25/Monthly
Price/Sqft
$159/sqft
Listed
180+ days ago

Home Details for 55 Timothy Drive

Interior Features

Interior Details
Basement: Full,FinishedNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom, Dining Room, Kitchen, Living Room, Rec Play Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2522 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Gas Water Heater, Water HeaterDishwasherLaundry: Lower LevelMicrowaveRefrigerator
Heating & Cooling
Heating: Hot Water,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: DeckExterior: Rain GuttersFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1822 Square FeetFinished Area (below surface): 700 Square Feet

Property Information

Year Built
Year Built: 1991
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: 1016010

Price & Status

Price
List Price: $405,000Price Per Sqft: $159/sqft
Status Change & Dates
Off Market Date: Mon Dec 01 2025Possession Timing: Immediate

Active Status

MLS Status: Closed

Location

Direction & Address
City: MiddletownCommunity: Westfield
School Information
Elementary School: Per Board of EdHigh School: Middletown

Building

Building Area
Building Area: 2522 Square Feet

Community

Community Features: Planned Unit Development

HOA

HOA Fee Includes: Road MaintenanceHas an HOAHOA Fee: $305/Annually

Lot Information

Lot Area: 10018.8 sqft

Miscellaneous

BasementMls Number: 24140922Attic: Storage, Access Via HatchAttribution Contact: (203) 687-0992Above Grade Unfinished Area: 1822

Additional Information

Planned Unit Development
Last check for updates: about 3 hours ago
Listed by Jordan Ostrofsky, (203) 687-0992
KW Legacy Partners, (860) 313-0700
Bought with: Carl J. Guild, (860) 813-2275, Carl Guild & Associates, (860) 474-3500
Source: Smart MLS, MLS#24140922

Price History for 55 Timothy Drive

DatePriceEventSource
01/09/2026$400,000Sold
Smart MLS #24140922
11/20/2025$405,000Listed For SaleSmart MLS #24140922
06/02/2017$262,500Sold
Smart MLS #G10203483
03/24/2017$269,900PendingAgent Provided
03/12/2017$269,900Listed For SaleAgent Provided
12/29/2000$179,900Sold
N/A
08/12/1999$160,500Sold
N/A

Market trends in Middletown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$293K
$11.67KMoM
Sale-to-List Price
103.3%
0.9%MoM
Price per sq ft
$236
$1MoM
Available listings
92
8MoM
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Property Tax and Assessment

Year2025
Tax$9,654
Assessment$248,170
Home facts updated by county records

Comparable Sales for 55 Timothy Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
70 Timothy Drive, Middletown, CT
0.04
Single-Family Home
$511,000
05/01/26
4
2.5
3,043
20 Benjamin Lane, Middletown, CT
0.23
Single-Family Home
$429,900
09/22/25
3
2.5
2,076
58 Morning Glory Drive, Middletown, CT
0.21
Single-Family Home
$505,000
05/22/26
4
2.5
2,360
101 Morning Glory Drive, Middletown, CT
0.23
Single-Family Home
$429,900
12/05/25
3
2.5
2,031
3 East Lake Place, Middletown, CT
0.14
Single-Family Home
$350,000
04/30/26
3
1.5
1,200
78 Rolling Green, Middletown, CT
0.41
Single-Family Home
$465,000
11/25/25
3
2.5
2,329
14 Greenview Terrace, Middletown, CT
0.44
Single-Family Home
$435,000
08/28/25
3
2.5
2,096
13 Little River Lane, Middletown, CT
0.20
Single-Family Home
$315,000
07/22/25
3
1.5
1,356

Nearby homes

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Assigned Schools

These are the assigned schools for 55 Timothy Drive.
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 Middletown

At least 387 Trulia users voted on each feature.

  • 84 % Say it's dog friendly

  • 82 % Say car is needed

  • 74 % Say parking is easy

  • 73 % Say there's holiday spirit

  • 71 % Say there are sidewalks

  • 62 % Say yards are well-kept

  • 62 % Say people would walk alone at night

  • 61 % Say streets are well-lit

  • 61 % Say kids play outside

  • 55 % Say it's quiet

  • 52 % Say it's walkable to restaurants

  • 49 % Say there's wildlife

  • 48 % Say neighbors are friendly

  • 42 % Say they plan to stay for at least 5 years

  • 38 % Say it's walkable to grocery stores

  • 23 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Travis Thomas
    "The people are very very nice. I am very comfortable here . Not afraid to leave the front door open or the slider to the deck"
    1
    Flag
  • James.sargeant30
    "My friend lives there she loves it very much good place to live with family everyone works and goes to school"
    0
    Flag
  • Julia Taylor
    "very easy to get to and from work when living in middletown! I work in Cheshire. Just hop onto 691 and in 15 min you’re there. "
    0
    Flag
  • Calm Teacher
    "Good schools for the most part and safe neighborhoods. Students don’t have to wear uniforms. The town has a lot of nice parks. "
    0
    Flag
  • Life Withsymph
    "You get to see the dogs being walked and you can pet them and talk to the owners build bonds , you will be able to see all different types of dogs and mixes "
    0
    Flag
  • Phyloren
    "Watch your children it is not safe. The schools have fights every day. The learning atmosphere is is awful. "
    0
    Flag
  • Kelly Capone
    "I haven’t lived here long and I’m not exactly sure what community events make my neighborhood special. "
    2
    Flag
  • Dlc.marie0816
    "I moved out here in June and I definitely love it.. feels like a nice place for my family, specially my kids"
    0
    Flag
  • Trulia User
    "There are dog parks everywhere, and plenty of places to walk uour dog. Even if you are in an apartment "
    3
    Flag
  • Michael W. W.
    "Wadsworth mansion has many trails. They have several public events in the summer time. There are two other state parks very close that are easily accessible by foot or car. Main Street has many restaurants that offer dine-in, carry out and delivery."
    12
    Flag
  • Joseph V.
    "Middletown is a town that has enjoyable events such as the weekly farmers market the the fall festival and during Christmas time they put up the huge Christmas trees "
    3
    Flag
  • Marquis W. G.
    "My neighborhood is surrounded by semi luxury condos and townhouses full of hard working families. Very family oriented and very peaceful. I love it here!"
    3
    Flag
  • Ishmaila L.
    "Dog owners will like the space made to them to run around and exercise. There are also doggy bags available to help pick up dog waste."
    2
    Flag
  • Marquis W. G.
    "I just moved here recently and I love the community and neighbors. The property is very clean and the neighborhood feels very family oriented "
    0
    Flag
  • Francheska M.
    "Neighbors are very friendly with a really good community sense. Conveniently close to stores and park. "
    0
    Flag
  • Shelby W.
    "The commute downtown on public transportation has changed and not as Easy. Driving downtown is 5-7 minutes. Walking is a half hour. "
    0
    Flag
  • ISA M.
    "School system is awesome in Middletown Ct. You can walk around at night time and still feel safe! I like it that much!"
    0
    Flag
  • Sekernan
    "I drive about 7 or 8 miles to work. Traffic depends on day and time of day. Never too bad. Takes 11-15 minutes to get there. I am able to walk to some stores and laundromats in the area, sidewalks make this safe"
    0
    Flag
  • Richard D.
    "The is a walking/biking trail and a dog park. Nice clean areas safe for walking and locations for waste disposal."
    0
    Flag
  • Christina Y.
    "The schools are awesome for elementary and high school and college.The food here in the restaurants are good too."
    2
    Flag
  • Chelsea C.
    "it’s good but I drive there’s never much traffic which is good and easy to get to work and drive kids to school"
    1
    Flag
  • Michelle E. B.
    "my neighborhood has access to transportation, stores, schools, hospital and is close to downtown. "
    1
    Flag
  • Marisa
    "commute is pretty good, surrounded by plenty of stores and easy access to many restaurants and everything one could need"
    0
    Flag
  • Trevor N.
    "We live near wadsworth mansion so they often have public concerts, vendors, ect. Snow school is right down the road as well. "
    1
    Flag
  • Marisa
    "i think it’s a great place to own a dog .. i have a chocolate lab myself and their are tons of sidewalks and a bike trail as well. everyone’s pretty friendly & clean up after their dogs as well"
    0
    Flag
  • Frankie T.
    "Lots of pups here in Middletown and even some dog-friendly restaurant patios! Our dog loves the walkable North End."
    1
    Flag
  • Molinaronijhana
    "We have bike shows, Christmas carriage rides and a huge tree for Christmas, trick or treating on main st and a wonderful YMCA "
    1
    Flag
  • Shellycato19
    "A lot of dogs living in the area. Not a lot of places to really run, but nice places to take a long and peaceful walk. Unfortunately a lot of owners don’t clean up after their dogs, but it’s starting g to get a little better. Overall a decent place to have pups. "
    1
    Flag
  • Shewarrens
    "It’s a beautiful place to live , It’s a very nice place to grow your kids there’s of restaurant and park and transportation if you don’t drive"
    2
    Flag
  • Asweetrdrm
    "It's a good place to live, low crime rate. Neighbors are friendly. Plenty of kids and close to schools"
    1
    Flag
  • Kurt.r.wentzell
    "There’s not a lot of traffic on my street. A lot of the neighbors have dogs and you always see people walking their dogs on leashes. There’s also a park just down the street."
    1
    Flag
  • Qcockrell
    "more activities for the kids to keep them busy and there need to be more job opportunities for the ones that are looking for a job"
    1
    Flag
  • Lisa C.
    "the neighborhood is a private road with only 1 way in/out. everyone knows everyone. no crime all neighbors have lived here since 1950s and passed houses down through generations. the elementary school is in walking distance safe neighborhood where children could play in the road and not have to worry about traffic"
    2
    Flag
  • Wolver1068.jb
    "We have a great town to raise children in and is rated one of top towns in the United States for raising children. Lots of his Tory in town and the surrounding areas. Great place to have a family vacation!"
    0
    Flag
  • Alnoor R.
    "Decent schools,safe, plenty of kid friendly space. Property taxes are high in CT. Job marked is tepid at best"
    0
    Flag
  • Jagalpure.prafull
    "Nice city and nebourhood. Good parks nearby. very well connected to major highways. Boston and New York are nearest best cities to explore. "
    0
    Flag
  • Brian
    "great central location in CT, close to downtown and highways. quiet neighborhood, but properties very close together"
    0
    Flag
  • Kathy
    "Best restaurant and nightlife scene in the area. outstanding, unique restaurants and small businesses. Plenty of daytime family events on Main street like car shows, bike shows, Christmas tree lighting. Vibrant, diverse community in a college town with a lot of great history that is still celebrated."
    0
    Flag
  • Mhasbro13
    "I’ve lived in this community for 4 years. I love the amenities offered to us. My neighbors are very friendly. Most everyone will say hello when they see you, even if they don’t know you. Great place to liven."
    0
    Flag
  • Leonardo V.
    "It is a very safe place to live..also shopping is close. The neighbors are friendly and very courteous.."
    0
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Homes for sale near 55 Timothy Drive

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Off Market Homes Near 55 Timothy Drive

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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.