20044 Cool Spring Rd, Milton, DE 19968
OFF MARKET

20044 Cool Spring Rd
Milton, DE 19968

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

$650,600

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $3,592/mo*
Refinance Your Home

$650,600

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $3,592/mo*
Refinance Your Home
5 Beds
4.5 Baths
2,820 sqft
(on 2 acres)

Home Value

Trulia Estimate
$651K
Since last month
Increased$4K (+0.5%)
Since last year
Increased$28K (+4.5%)
Since last sale
Increased$204K (+45%)
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 +324% in the last 10 years
MonthEstimated value
2026
August 2026$657K
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
20058 Cool Spring Rd, Milton, DE
0.03
Single-Family Home
$315,400
10/28/25
4
-
2,512
20346 Cool Spring Rd, Milton, DE
0.57
Single-Family Home
$735,000
10/06/25
4
2.5
1,914
18044 Marley Ln, Milton, DE
0.63
Single-Family Home
$565,000
11/04/25
5
3
2,835
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
16560 Asher Ct, Milton, DE
0.61
Single-Family Home
$475,000
08/25/25
3
2
2,343

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
20296 Bundick Branch Dr, Milton, DE 19968
0.21
$505,000
3
3
2,892
Recently Sold
29403 Cynthia Ln, Milton, DE 19968
0.39
$709,100
3
3
763
Off Market
29405 Cynthia Ln, Milton, DE 19968
0.41
$691,000
3
2
2,230
Off Market
29404 Cynthia Ln, Milton, DE 19968
0.42
$732,400
4
4.5
418
Off Market
Montauk, Milton, DE 19968
0.42
$595,400+
3
2
2,102
-
Waterford, Milton, DE 19968
0.42
$765,400+
4
3.5
4,810
-
Mayberry, Milton, DE 19968
0.42
$655,400+
3
2
2,925
-
Cassidy, Milton, DE 19968
0.42
$675,400+
4
3.5
3,439
-
Whimbrel, Milton, DE 19968
0.42
$625,400+
3
2
2,544
-
Kingfisher, Milton, DE 19968
0.42
$665,400+
3
2.5
3,531
-
Jameson, Milton, DE 19968
0.42
$695,400+
3
2.5
4,123
-
Shearwater, Milton, DE 19968
0.42
$715,400+
3
2.5
3,990
-

Local Information

  • Map ViewExplore the area around 20044 Cool Spring Rd.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1999
Lot Size
2 acres
Living Area
2,820 sqft
Price/Sqft
$231
Parking
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. It is currently off market. The Trulia Estimate is $650,600, with a rent estimate of $2,928/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 July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$472K
$23.33KMoM
Sale-to-List Price
98.3%
0.1%MoM
Price per sq ft
$240
$4MoM
Available listings
126
1MoM
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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
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Apartments for Rent

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Explore by feature - Pet Friendly

7 pet-friendly rentals in Milton, DE

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10 rentals with air conditioning in Milton, DE

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10 rentals with a washer/dryer in Milton, DE

Homes for sale near 20044 Cool Spring Rd

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Off Market Homes Near 20044 Cool Spring Rd

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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 $650,600.
  • 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 buyer's market, based on recent for-sale activity.
  • What's the median sale price in Milton?
    The median sale price in Milton is $472K. That is up $23.33K from the prior month.
  • 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.