422 Chestnut St, Milton, DE 19968
Property image
Property image
OFF MARKET

$495,800

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,300 sqft

422 Chestnut St, Milton, DE 19968

Est. Refi. Payment $2,861/mo*
Refinance Your Home
Currently Off Market - Sold Jan 1, 2015 for $385,000

Home Value

Trulia Estimate
$496K
Since last month
Increased$11K (+2.2%)
Since last year
Decreased$12K (-2.4%)
Since last sale
Increased$113K (+29.5%)
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 +121% in the last 10 years
MonthEstimated value
2026
September 2026$498K
August 2026$488K
July 2026$485K
June 2026$492K
May 2026$502K
April 2026$497K
March 2026$501K
February 2026$494K
January 2026$478K
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
302 Walnut St, Milton, DE
0.21
Single-Family Home
$499,000
02/02/26
4
2.5
2,200
208 Federal St, Milton, DE
0.22
Single-Family Home
$450,000
08/18/26
3
3
2,000
501 Federal St, Milton, DE
0.07
Single-Family Home
$419,000
07/10/26
3
1.5
1,300
106 Fulham Dr, Milton, DE
0.31
Single-Family Home
$425,000
05/08/26
3
3
2,429
513 Federal St, Milton, DE
0.12
Single-Family Home
$365,000
03/31/26
3
2
1,586
116 Morgan Way, Milton, DE
0.34
Single-Family Home
$380,000
06/05/26
4
2
4,028
305 Walnut St, Milton, DE
0.19
Single-Family Home
$355,000
01/23/26
3
3.5
1,280
207 Summerwalk Blvd, Milton, DE
0.50
Single-Family Home
$455,000
03/12/26
3
2.5
1,986
303 Brick Ln, Milton, DE
0.38
Single-Family Home
$425,000
10/20/25
3
2.5
1,878
111 Prospect St, Milton, DE
0.72
Single-Family Home
$444,990
11/25/25
4
3
2,305

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
501 Federal St, Milton, DE 19968
0.07
$419,000
3
1.5
1,300
Recently Sold
424 Federal St, Milton, DE 19968
0.08
$350,000
2
1
928
Recently Sold
109 Hazzard Ln, Milton, DE 19968
0.08
$160,000
-
-
-
Recently Sold
201 Sassafras Ln, Milton, DE 19968
0.08
$513,400
3
2.5
2,018
Off Market
405 Chestnut St, Milton, DE 19968
0.10
$490,800
3
2.5
1,350
Off Market
203 Sassafras Ln, Milton, DE 19968
0.09
$150,000
-
-
-
For Sale
513 Federal St, Milton, DE 19968
0.12
$365,000
3
2
1,586
Recently Sold
108 Atlantic St, Milton, DE 19968
0.11
$414,800
3
1.5
-
Off Market
104 Sassafras Ln, Milton, DE 19968
0.13
$381,000
4
3
2,211
Off Market
106 Prettyman St, Milton, DE 19968
0.15
$716,600
4
3.5
3,100
Off Market
311 Chestnut St, Milton, DE 19968
0.15
$550,400
4
2
3,111
Off Market
120 Village Center Blvd, Milton, DE 19968
0.15
$414,100
3
2.5
1,664
Off Market

Local Information

  • Map ViewExplore the area around 422 Chestnut St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1900
2,300 sqft
$216/sqft

About this House

Custom Renovation in the heart of Milton's Historic District with an updated floorplan and two additions to create a home you can really live in. The whole house was sided with factory finished hardi-plank fiber cement board siding, in a warm Khaki color with white trim and black accents and doors. The windows are Weather Shield aluminum-clad insulated double-hung wood windows. All of the systems, plumbing and wiring are new and energy efficient. There are new Trane 13-Seer split heat pumps...
422 Chestnut St, Milton, DE 19968 is a 4 bedroom, 3 bathroom, 2,300 sqft single-family home built in 1900. It last sold for $385,000 on Jan 1, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $495,800, with a rent estimate of $2,594/month.

Home Details for 422 Chestnut St

Interior Features

Interior Details
BasementNumber of Rooms: 6
Levels, Entrance, & Accessibility
Stories: 2

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 6426 sqft

Price and Tax history

DateEventPrice
Jan 1, 2015
Source: Long & Foster Broker Feed #1001367970_100
Sold
$385,000
Jul 22, 2009
Source: N/A
Sold
$385,000
May 13, 2009
Source: Agent Provided
PriceChange
$399,000
Price decreased by 5%
Mar 18, 2009
Source: Agent Provided
PriceChange
$420,000
Price decreased by 1%
Dec 22, 2008
Source: Agent Provided
Listed For Sale
$425,000

Market trends in Milton

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$481K
$9.61KMoM
Sale-to-List Price
—
Price per sq ft
$236
$3MoM
Available listings
138
12MoM

Around this home

What Locals Say about Milton

At least 58 Trulia users voted on each feature.

  • 97 % Say parking is easy

  • 92 % Say car is needed

  • 92 % Say yards are well-kept

  • 91 % Say it's dog friendly

  • 84 % Say people would walk alone at night

  • 81 % Say there's holiday spirit

  • 70 % Say they plan to stay for at least 5 years

  • 67 % Say kids play outside

  • 64 % Say neighbors are friendly

  • 64 % Say it's quiet

  • 62 % Say streets are well-lit

  • 61 % Say there's wildlife

  • 57 % Say there are sidewalks

  • 56 % Say there are community events

  • 42 % Say it's walkable to restaurants

  • 39 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Cris2461.cm
    "Going to Wilmington is over an hour and half. Better shopping choices are approximately 45 minutes away. Long. No public transportation "
    0
    Flag
  • Ashtat09
    "My neighbors are my friends I like to be around. We play pickleball together 3 to 5 days a week. We do aerobics together and still enjoy bbq parties on the weekends together. "
    0
    Flag
  • Ashtat09
    "I have lived in this neighborhood almost 2 years. Since it is a new development, most everyone wants make new friends and enjoy their new beach home."
    1
    Flag
  • Tj L.
    "My kids live in this area and I’m here multiple times a week. It’s very quiet and has a nice homely feel to it "
    6
    Flag
  • Evritt3
    "Everyone is friendly and picks up after their dogs. No one discriminates against breeds. Anyone and everyone is welcome. "
    7
    Flag
  • Quinese W.
    "I have lived in this neighborhood for eleven years. It's a quiet well maintained street with plenty of on and off street parking, as well as public transportation and friendly neighbors. There are several Elementary, Middle and High Schools in the area. Milton is nearby to many towns/cities that offer fun-filled entertainment for the entire family! This a wonderful place to raise a family, or start out on your own. Very close to Beaches and Resort Areas."
    6
    Flag
  • Gtdonze
    "No public trans. Need a car to go to stores post office dr office just about anywhere. Country living is the trade off. I love it"
    0
    Flag
  • Jessica D.
    "I’ve lived in Milton for almost 20 years. It’s a family town with friendly neighbors and a lot of charm. "
    0
    Flag
  • Trulia User
    "Well kept sidewalks and parks. Easy walking to stores, Milton Theatre, parks, gas station and library. "
    0
    Flag
  • Joepickleball
    "It's got flare with eclectic people. There are a variety of outdoor events for a varied palate. The staples are close by. Name brand and one-of-a-kind stores share the town's boundaries."
    6
    Flag
  • jdoherty24
    "A few miles to the beach so it is quiet. Close enough to enjoy the beach, nightlife and shopping but far enough away so that it is quiet at night"
    0
    Flag
  • Johnanicosia
    "Great place to retire or as a weekend retreat. Prime Hook offers very safe, clean beaches for kids and dogs. Miles of beaches to walk, exploring for wildlife and shells. Excellent place to sail and kayak. Sand bars offer fun for kids. Community backs up to Prime Hook Wildlife refuge teaming with wildlife with nesting ospreys, eagles and other waterfowl. Quiet and peaceful and a perfect all year round destination. It is one of the closest Delaware Bay beaches to Philly, DC, MD and VA.. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 422 Chestnut St

  • What is 422 Chestnut St estimated to be worth?
    Trulia's estimated value for 422 Chestnut St in Milton, DE is $495,800.
  • What is the price history for 422 Chestnut St?
    422 Chestnut St in Milton, DE last sold for $385,000 in January 2015.
  • Is Milton a buyer's or seller's market?
    Milton is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Milton?
    The median sale price in Milton is $481K. That is up $9.61K from the prior month.
  • How big is the lot at 422 Chestnut St?
    The lot at 422 Chestnut St in Milton, DE is about 0.15 acres (6,426 sq ft).

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