20044 Cool Spring Rd, Milton, DE 19968
OFF MARKET

$660,000

Trulia Estimate
  • 5 Beds
  • 4.5 Baths
  • 2,820 sqft (on 2 acres)

20044 Cool Spring Rd, Milton, DE 19968

Refinance Your Home
Currently Off Market - Sold Jul 31, 2020 for $453,000

Home Value

Trulia Estimate
$660K
Since last month
Increased$2K (+0.3%)
Since last year
Increased$35K (+5.6%)
Since last sale
Increased$209K (+46.1%)
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 +325% in the last 10 years
MonthEstimated value
2026
November 2026$662K
October 2026$658K
September 2026$660K
August 2026$662K
July 2026$663K
June 2026$653K
May 2026$648K
April 2026$645K
March 2026$620K
February 2026$608K
January 2026$597K
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
20296 Bundick Branch Dr, Milton, DE
0.21
Single-Family Home
$505,000
11/18/25
3
3
2,892
20296 Bundicks Branch Ln, Milton, DE
0.21
Single-Family Home
$505,000
11/21/25
3
-
3,236
29303 Otto Dr, Milton, DE
0.47
Single-Family Home
$1,160,000
02/06/26
4
4.5
2,528
29309 Otto Dr, Milton, DE
0.50
Single-Family Home
$1,041,013
06/12/26
4
3.5
2,528
29433 Cynthia Ln, Milton, DE
0.52
Single-Family Home
$1,058,739
12/08/25
4
3.5
2,528
29427 Cynthia Ln, Milton, DE
0.47
Single-Family Home
$780,260
12/22/25
3
2.5
2,679
28365 Boater Pl, Milton, DE
0.83
Single-Family Home
$410,000
04/30/26
5
2.5
1,566
29310 Otto Dr, Milton, DE
0.52
Single-Family Home
$823,569
06/22/26
4
3
1,971
28359 Martins Farm Rd, Milton, DE
0.68
Single-Family Home
$232,000
04/06/26
4
1
2,568
29340 Otto Dr, Milton, DE
0.70
Single-Family Home
$880,341
11/13/25
4
4.5
2,568

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
20040 Cool Spring Rd, Milton, DE 19968
0.03
$715,800
4
-
3,038
Off Market
20058 Cool Spring Rd, Milton, DE 19968
0.03
$315,600
4
-
2,512
Off Market
20024 Cool Spring Rd, Milton, DE 19968
0.06
$552,100
4
-
2,358
Off Market
20072 Cool Spring Rd, Milton, DE 19968
0.07
$917,800
5
-
4,424
Off Market
Lot 3 Cool Spring, Milton, DE 19968
0.08
-
-
-
-
Off Market
Lot 3 Cool Spring Road, Milton, DE 19968
0.08
-
-
-
-
Off Market
20329 Bundick Branch Dr, Milton, DE 19968
0.13
-
-
-
-
Off Market
20330 Bundicks Branch Ln, Milton, DE 19968
0.14
$466,400
3
-
1,648
Off Market
20329 Bundicks Branch Ln, Milton, DE 19968
0.14
$441,600
3
2
1,880
Off Market
20309 Bundick Branch Dr, Milton, DE 19968
0.16
$505,100
3
3
2,700
Off Market
17282 King Phillip Way #58, Lewes, DE 19958
0.16
$393,100
3
-
1,781
Off Market
28882 Poplar Grove Dr, Milton, DE 19968
0.17
$445,700
3
2
1,719
Off Market
20328 Bundicks Branch Ln, Milton, DE 19968
0.18
$535,700
3
-
2,474
Off Market
28888 Poplar Grove Dr, Milton, DE 19968
0.18
$386,700
3
-
1,753
Off Market
20239 Forest Rd, Milton, DE 19968
0.18
$476,000
3
-
1,680
Off Market
19090 Cool Spring Rd, Milton, DE 19968
0.18
$710,600
4
-
2,857
Off Market
28892 Poplar Grove Dr, Milton, DE 19968
0.19
$584,500
4
-
2,765
Off Market
20310 Bundicks Branch Ln, Milton, DE 19968
0.19
$486,500
3
-
2,278
Off Market
20349 Forest Rd, Milton, DE 19968
0.20
-
Studio
-
-
Off Market
Lot 9 Forest Rd, Milton, DE 19968
0.20
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 20044 Cool Spring Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1999
2 acre lot
2,820 sqft
$234/sqft
Garage

About this House

ONE OF A KIND PROPERTY! Enjoy sprawling privacy, a barn for horses, pond, pool and an inviting 4+ bedroom home with a garage apartment. The spacious home offers a bright enclosed porch, indoor hot tub, first floor master suite, fresh paint, loads of room to relax, and serene views of nature life. Make your dreams a reality today, close to beaches, dining and shopping.
20044 Cool Spring Rd, Milton, DE 19968 is a 5 bedroom, 5 bathroom, 2,820 sqft single-family home built in 1999. It last sold for $453,000 on Jul 31, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $660,000, with a rent estimate of $3,112/month.

Home Details for 20044 Cool Spring Rd

Interior Features

Interior Details
BasementNumber of Rooms: 6Types of Rooms: Dining Room
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Laminate, Linoleum Vinyl
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: VinylFoundation Type: Masonry
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Price and Tax history

DateEventPrice
Jul 31, 2020
Source: N/A
Sold
$453,000
Oct 29, 2018
Source: Agent Provided
ListingRemoved
$399,900
Oct 15, 2018
Source: Agent Provided
PriceChange
$399,900
Price decreased by 6%
Jul 31, 2018
Source: Agent Provided
PriceChange
$424,900
Price decreased by 9%
May 7, 2018
Source: Agent Provided
PriceChange
$465,000
Price decreased by 6%

Market trends in Milton

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
127
11MoM
Sourced by Trulia Market Trends

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 20044 Cool Spring Rd

  • What is 20044 Cool Spring Rd estimated to be worth?
    Trulia's estimated value for 20044 Cool Spring Rd in Milton, DE is $660,000.
  • What is the price history for 20044 Cool Spring Rd?
    20044 Cool Spring Rd in Milton, DE last sold for $453,000 in July 2020.
  • Is Milton a buyer's or seller's market?
    Milton is currently a balanced market, based on recent for-sale activity.
  • What do residents say about Milton?
    Residents describe Milton, DE as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Milton, DE.
  • Does 20044 Cool Spring Rd have air conditioning?
    Yes, 20044 Cool Spring Rd in Milton, DE has air conditioning.
  • Does 20044 Cool Spring Rd have a pool?
    Yes, 20044 Cool Spring Rd in Milton, DE has a pool.

Explore by feature - Air Conditioning

9 rentals with air conditioning in Milton, DE

Explore by feature - Washer/dryer

11 rentals with a washer/dryer in Milton, DE

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Off Market Homes Near 20044 Cool Spring Rd

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