29 Chester Drive, Windsor Locks, CT 06096
SOLD
DEC 8, 2025

$269,100

Trulia Estimate
  • 3 Beds
  • 1 Bath
  • 967 sqft (on 0.33 acres)

29 Chester Drive, Windsor Locks, CT 06096

Est. Refi. Payment $1,999/mo*
Refinance Your Home
Currently Off Market - Sold Dec 8, 2025 for $260,000 (0% above list price)

Home Value

Trulia Estimate
$269K
Since last month
$100 (0%)
Since last year
Decreased$28K (-9.4%)
Since last sale
Increased$9K (+3.5%)
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 +73% in the last 10 years
MonthEstimated value
2026
September 2026$269K
August 2026$269K
July 2026$272K
June 2026$272K
May 2026$268K
April 2026$268K
March 2026$265K
February 2026$264K
January 2026$262K
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
235 Reed Avenue, Windsor Locks, CT
0.05
Single-Family Home
$330,000
06/12/26
3
1
967
202 Reed Avenue, Windsor Locks, CT
0.14
Single-Family Home
$340,000
07/31/26
3
1
967
255 Reed Avenue, Windsor Locks, CT
0.12
Single-Family Home
$346,000
12/19/25
3
1
1,255
30 Barbara Drive, Windsor Locks, CT
0.24
Single-Family Home
$318,000
05/28/26
3
1
967
4 Lynn Lane, Windsor Locks, CT
0.10
Single-Family Home
$300,000
10/19/25
3
1.5
1,184
15 Dickerman Avenue, Windsor Locks, CT
0.25
Single-Family Home
$210,000
02/10/26
3
1
1,479
19 Thomas Street, Windsor Locks, CT
0.15
Single-Family Home
$312,000
01/22/26
3
1.5
1,184

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
33 Chester Drive, Windsor Locks, CT 06096
0.02
$366,900
3
1
967
Off Market
36 Chester Drive, Windsor Locks, CT 06096
0.05
$401,700
3
2
1,486
Off Market
235 Reed Avenue, Windsor Locks, CT 06096
0.05
$330,000
3
1
967
Recently Sold
80 West Street, Windsor Locks, CT 06096
0.10
$272,300
2
1
720
Off Market
32 Hazel Street, Windsor Locks, CT 06096
0.05
$326,900
3
1.5
967
Off Market
12 Chester Drive, Windsor Locks, CT 06096
0.08
$350,000
3
2
1,217
Recently Sold
85 West Street, Windsor Locks, CT 06096
0.12
$340,700
2
2.5
1,332
Off Market
210 Reed Avenue, Windsor Locks, CT 06096
0.12
$383,700
3
1.5
1,367
Off Market
8 Chester Drive, Windsor Locks, CT 06096
0.09
$392,700
4
2.5
1,463
Off Market
202 Reed Avenue, Windsor Locks, CT 06096
0.14
$340,000
3
1
967
Recently Sold
19 Sadler Street, Windsor Locks, CT 06096
0.11
$355,400
3
1
1,447
Off Market

Local Information

  • Map ViewExplore the area around 29 Chester Drive.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1959
0.33 acre lot
967 sqft
$269/sqft

About this House

Welcome to 29 Chester Drive - a delightful ranch-style home nestled in one of Windsor Locks' most desirable neighborhoods. This three-bedroom, one bathroom house offers several recent updates, including brand-new 100-amp electrical service and stylish vinyl waterproof flooring throughout the kitchen, bathroom, and partially finished basement recreational space. New paint brightens every room - and the exterior, too - giving the home a fresh, move-in-ready feel. Step outside and enjoy the tranquil and sprawling back yard from your spacious deck - perfect for relaxing or outdoor entertaining. Don't wait - make this charming home yours just in time for the holidays!
29 Chester Drive, Windsor Locks, CT 06096 is a 3 bedroom, 1 bathroom, 967 sqft single-family home built in 1959. It last sold for the $259,900 asking price on Dec 8, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $269,100, with a rent estimate of $2,206/month.
Last check for updates: about 23 hours ago
Listed by Justin Mokerzecki, (860) 469-5447
Glanville Real Estate, (860) 372-5898
Bought with: Alma Hernandez, (860) 268-2718, Century 21 AllPoints Realty, (860) 745-2121
Source: Smart MLS, MLS#24129502

Home Details for 29 Chester Drive

Interior Features

Interior Details
Basement: Partial,Partially FinishedNumber of Rooms: 5Types of Rooms: Master Bedroom, Bedroom, Bathroom, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1
Dimensions and Layout
Living Area: 967 Square Feet
Appliances & Utilities
Appliances: Gas Range, Oven/Range, Refrigerator, Dishwasher, Washer, Dryer, Gas Water Heater, Water HeaterDishwasherDryerRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
No Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: DeckFencing: Chain LinkOther Structures: Shed(s)Foundation: Concrete PerimeterNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageParking: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 967 Square Feet

Property Information

Year Built
Year Built: 1959
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 787633

Price & Status

Price
List Price: $259,900Price Per Sqft: $269/sqft
Status Change & Dates
Off Market Date: Mon Nov 03 2025Possession Timing: Immediate

Active Status

MLS Status: Closed

Media

Location

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

Building

Building Area
Building Area: 967 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.33 acres

Miscellaneous

BasementMls Number: 24129502Attic: Access Via HatchAttribution Contact: (860) 469-5447Above Grade Unfinished Area: 967Activation Date: Fri Oct 17 2025

Price and Tax history

DateEventPrice
Dec 8, 2025
Source: Smart MLS #24129502
Sold
$260,000
Nov 4, 2025
Source: Smart MLS #24129502
Pending
$259,900
Oct 29, 2025
Source: Smart MLS #24129502
PriceChange
$259,900
Price decreased by 5%
Oct 17, 2025
Source: Smart MLS #24129502
Listed For Sale
$275,000
Dec 15, 2006
Source: Smart MLS #G433454
Sold
$195,000

Market trends in Windsor Locks

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
34
9MoM

Around this home

What Locals Say about Windsor Locks

At least 84 Trulia users voted on each feature.

  • 88 % Say car is needed

  • 86 % Say parking is easy

  • 80 % Say it's dog friendly

  • 71 % Say yards are well-kept

  • 70 % Say there are sidewalks

  • 69 % Say there's holiday spirit

  • 67 % Say people would walk alone at night

  • 65 % Say kids play outside

  • 61 % Say streets are well-lit

  • 61 % Say it's quiet

  • 59 % Say there's wildlife

  • 52 % Say they plan to stay for at least 5 years

  • 43 % Say it's walkable to restaurants

  • 41 % Say neighbors are friendly

  • 29 % Say it's walkable to grocery stores

  • 21 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Tam
    "Walks around the block. Most people say hello and know each other. Young kids hang out together and ride bikes."
    0
    Flag
  • Djhootie
    "Quiet and generally private. It used to be military housing but are now condos. The community is friendly and peaceful."
    0
    Flag
  • Silena W.
    "It’s a very small town, nice to live in but not much to do here. Kids in the schools are rude and are very diverse, teachers are into picking favorites when it comes to grading "
    0
    Flag
  • Livelovelaughkjmf
    "In this neighborhood you will see all ages...maybe a family walking on the sidewalk along with their child riding their bike with training wheels or a couple walking for a sunset view at dusk. The friendliness of all is unique. Everyone keeps their yard nicely mowed and they keep the sidewalks clear in the snowy weather! It is a very relaxing area to live in and I highly recommend it!"
    9
    Flag
  • Robinander
    "I have lived in Windsor Locks for 40 years. I was raised here and now I raise my child here. As of right now I live on a busy street with not a big yard. We do walk more because now we are closer to friends, the park, restaurants and stores. "
    5
    Flag
  • Dawn D.
    "Everyone is friendly and the neighborhood is safe for kids. Park is taken care of, pool is open to public. Shops are close by. Rail station is being rebuilt"
    0
    Flag
  • Velosocarina
    "family oriented, quiet and safe. all number neighbors are pretty friendly. families have the freedom to walk at any hour of the day"
    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 29 Chester Drive

  • What is 29 Chester Drive estimated to be worth?
    Trulia's estimated value for 29 Chester Drive in Windsor Locks, CT is $269,100.
  • What is the price history for 29 Chester Drive?
    29 Chester Drive in Windsor Locks, CT last sold for $260,000 in December 2025.
  • Is Windsor Locks a buyer's or seller's market?
    Windsor Locks is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Windsor Locks?
    Residents describe Windsor Locks, CT as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Windsor Locks, CT.
  • Does 29 Chester Drive have air conditioning?
    Yes, 29 Chester Drive in Windsor Locks, CT has air conditioning.
  • Does 29 Chester Drive have laundry facilities?
    Yes, 29 Chester Drive in Windsor Locks, CT has in-unit laundry.

Explore by feature - Air Conditioning

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