74 Chestnut Dr, Derby, CT 06418
Property image
Property image
OFF MARKET

$385,000

Trulia Estimate
  • 3 Beds
  • 1.5 Baths
  • 1,104 sqft (on 0.39 acres)

74 Chestnut Dr, Derby, CT 06418

Est. Refi. Payment $2,725/mo*
Refinance Your Home
Currently Off Market - Sold Mar 23, 2020 for $164,000

Home Value

Trulia Estimate
$385K
Since last month
Increased$2K (+0.6%)
Since last year
Decreased$700 (-0.2%)
Since last sale
Increased$218K (+132.7%)
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 +105% in the last 10 years
MonthEstimated value
2026
August 2026$382K
July 2026$380K
June 2026$385K
May 2026$385K
April 2026$379K
March 2026$368K
February 2026$362K
January 2026$353K
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
59 Chestnut Drive, Derby, CT
0.06
Single-Family Home
$455,000
11/26/25
3
1.5
1,108
311 Marshall Ln, Derby, CT
0.26
Single-Family Home
$300,000
12/19/25
3
2
1,500
25 Glen Drive, Ansonia, CT
0.14
Single-Family Home
$385,000
12/22/25
3
2
1,350
16 Chestnut Drive, Derby, CT
0.19
Single-Family Home
$442,500
07/17/26
3
2
1,756
7 Hale Drive, Ansonia, CT
0.21
Single-Family Home
$355,000
03/17/26
3
1
1,259
147 Ida Ave, Derby, CT
0.42
Single-Family Home
$175,000
06/24/26
3
1
1,008
11 Hale Drive, Ansonia, CT
0.23
Single-Family Home
$362,000
06/29/26
3
1.5
1,053
120 Pulaski Highway, Ansonia, CT
0.31
Single-Family Home
$392,000
03/20/26
3
1.5
1,568
8 Fox Hill Terrace, Ansonia, CT
0.19
Single-Family Home
$399,000
10/31/25
3
2
1,347
118 Pulaski Highway, Ansonia, CT
0.31
Single-Family Home
$445,000
10/03/25
3
2
1,624

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
29 Bartholomew Avenue, Ansonia, CT 06401
0.05
$375,700
3
1
968
Off Market
86 Chestnut Drive, Derby, CT 06418
0.04
$472,400
3
2
2,239
Off Market
71 Chestnut Drive, Derby, CT 06418
0.04
$319,000
3
1.5
1,080
Off Market
59 Chestnut Drive, Derby, CT 06418
0.06
$455,000
3
1.5
1,108
Recently Sold
25 Glen Drive, Ansonia, CT 06401
0.14
$385,000
3
2
1,350
Recently Sold
15 Golden Rod Drive, Ansonia, CT 06401
0.15
$416,400
3
1.5
1,492
Off Market
5 Beech Street, Derby, CT 06418
0.11
$427,100
3
2
1,498
Off Market
8 Fox Hill Terrace, Ansonia, CT 06401
0.19
$399,000
3
2
1,347
Recently Sold
16 Chestnut Drive, Derby, CT 06418
0.19
$442,500
3
2
1,756
Recently Sold
7 Hale Drive, Ansonia, CT 06401
0.21
$355,000
3
1
1,259
Recently Sold
9 Glenridge Drive, Ansonia, CT 06401
0.22
$425,000
3
2
1,910
For Sale
8 Bartholomew Avenue, Ansonia, CT 06401
0.21
$355,700
3
1
992
Off Market

Local Information

  • Map ViewExplore the area around 74 Chestnut Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1957
Lot Size
0.39 acres
Living Area
1,104 sqft
Price/Sqft
$349
Parking
Garage

About this House

Short Sale on quiet cul-de-sac provides a lovely home for the handyman. Older roof, some broken windows are easily outweighed by the full basement and hardwood floors throughout. A little bit of love will bring this gem back to its original glory. Sale and commission contingent on lender approval.
74 Chestnut Dr, Derby, CT 06418 is a 3 bedroom, 2 bathroom, 1,104 sqft single-family home built in 1957. It last sold for $164,000 on Mar 23, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $385,000, with a rent estimate of $2,774/month.

Home Details for 74 Chestnut Dr

Interior Features

Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 6
Fireplace & Spa
Hot Tub or Spa

Exterior Features

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

Property Information

Year Built
Year Built: 1957
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.39 acres

Price and Tax history

DateEventPrice
Mar 23, 2020
Source: Smart MLS #170225490
Sold
$164,000
Oct 9, 2019
Source: Agent Provided
ListingRemoved
$175,000
Sep 23, 2019
Source: Agent Provided
Pending
$175,000
Aug 29, 2019
Source: Agent Provided
PriceChange
$175,000
Price decreased by 8%
Aug 15, 2019
Source: Agent Provided
Listed For Sale
$189,900

Market trends in Derby

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
19
2MoM

Around this home

What Locals Say about Derby

At least 188 Trulia users voted on each feature.

  • 82 % Say car is needed

  • 77 % Say it's dog friendly

  • 67 % Say there are sidewalks

  • 67 % Say parking is easy

  • 66 % Say there's holiday spirit

  • 62 % Say streets are well-lit

  • 57 % Say yards are well-kept

  • 56 % Say it's walkable to restaurants

  • 56 % Say kids play outside

  • 54 % Say people would walk alone at night

  • 50 % Say it's quiet

  • 48 % Say it's walkable to grocery stores

  • 48 % Say neighbors are friendly

  • 47 % Say they plan to stay for at least 5 years

  • 38 % Say there's wildlife

  • 26 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Krystal
    "School district is crap. Kids run the streets at all hours of the night and cars have gotten stolen not to mention parts off of cars have disappeared and cops have done nothing about it."
    1
    Flag
  • Tashima
    "There are no sidewalks which makes it difficult to walk your dog. You have to walk on someone’s property or in the street. Walking in the street is very dangerous. "
    1
    Flag
  • Edwin Portillo
    "Keep dogs under their control and not let them run loose in the streets especially when they’re pit bulls "
    0
    Flag
  • Sheema
    "It is a safe and boring town. Close to grocery stores. No major attractions. Neighboring towns are nice. "
    0
    Flag
  • Thabushfamily
    "lived here 3 years typically quiet good schools and close to transit and shopping centers. river walk trails and parks!!"
    0
    Flag
  • Belinda.rone
    "The area is nice and quiet. You really need a car, but public transportation is accessible. The shopping area is good, with a variety of stores to choose from."
    0
    Flag
  • Francis M.
    "Very quiet & safe area to live in. Will sure miss it when I leave next month but highly recommend families to raise a family in this town "
    0
    Flag
  • Jeremey.lombard
    "I’ve lived in this city all my life. It’s small, and everything you need is no more than a 20 minute drive. Quant and cute!"
    0
    Flag
  • Maritza H.
    "Lived here one year. It’s quiet and secluded but it’s ok. Good for my granddaughter to grow up in. Thank you"
    0
    Flag
  • Cyntia A.
    "it's a hassle for parking when its December, january, February and march. quiet neighborhood. great to have pets here."
    1
    Flag
  • Lubna A.
    "It’s quite and there’s nice people here it feels safe. There’s really nothing to do out here which sucks but if you like quiet and peace this the neighborhood to be at "
    0
    Flag
  • Soquendo777
    "ive lived here for 14 years love tgis little town just wish there was more to due to keep me in town as far as parks playground i have to take them out of town so means spending money outside of derby instead of contributing to my town ."
    0
    Flag
  • Oya2019
    "Yes it’s ok people don’t know how to pick up dog poop up kids stepping in it they don’t pay attention otherwise good"
    0
    Flag
  • Jeremey.lombard
    "I’ve lived here all my life, it’s quiet and peaceful, beautiful scenery, and it’s easy to get anywhere. Great little city. "
    0
    Flag
  • Thabushfamily
    "I live walking distance from the train station. Great parks and trails. Close to shopping and the highways. "
    0
    Flag
  • Mikhail M.
    "it's a good starter neighborhood but not to stay long term. it has great potential and one day it will a bustling city. "
    0
    Flag
  • Mikhail M.
    "my neighbor is great, schools movies hospitals are only minutes away. shopping is easy with target and big Y close by as well."
    0
    Flag
  • Richard R. J.
    "Great neighborhood. I’ve been here for two years now. Love the lake view and being around a good amount of restaurants and hiking trails. "
    0
    Flag
  • Barbara
    "Too many drugs and violence,and police don’t care, taxes are too high, town has too much Violence and Crime rate is very high "
    1
    Flag
  • Francis
    "Heavy drug area rodents pest problems area is very low income run garbage everywhere houses sidewalks. House not maintained unsafe to walk at night"
    7
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 74 Chestnut Dr

  • What is 74 Chestnut Dr estimated to be worth?
    Trulia's estimated value for 74 Chestnut Dr in Derby, CT is $385,000.
  • What is the price history for 74 Chestnut Dr?
    74 Chestnut Dr in Derby, CT last sold for $164,000 in March 2020.
  • Is Derby a buyer's or seller's market?
    Derby is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Derby?
    Residents describe Derby, CT as dog-friendly, pedestrian-friendly, and easy to park in. See recently sold homes in Derby, CT.
  • Does 74 Chestnut Dr have air conditioning?
    Yes, 74 Chestnut Dr in Derby, CT has air conditioning.
  • How big is the lot at 74 Chestnut Dr?
    The lot at 74 Chestnut Dr in Derby, CT is about 0.39 acres (16,988 sq ft).

Explore by feature - Pet Friendly

7 pet-friendly rentals in Derby, CT

Explore by feature - Air Conditioning

12 rentals with air conditioning in Derby, CT

Explore by feature - Washer/dryer

12 rentals with a washer/dryer in Derby, CT

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 74 Chestnut Dr

Skip to last item
Skip to first item

Homes for sale near 74 Chestnut Dr

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item