Is Dewey Beach, DE walkable to grocery stores?

As of early 2026, 100% of users say it's walkable to grocery stores

Does Dewey Beach, DE have sidewalks?

As of early 2026, 100% of users say there are sidewalks

Is Dewey Beach, DE dog-friendly?

As of early 2026, 100% of users say it's dog friendly

What is 8 Chicago St estimated to be worth?

Trulia's estimated value for 8 Chicago St in Dewey Beach, DE is $2,576,500 .

Is Dewey Beach a buyer's or seller's market?

Dewey Beach is currently a balanced market, based on recent for-sale activity.

What are the closest schools to 8 Chicago St?

The closest schools to 8 Chicago St in Dewey Beach, DE are Beacon Middle School (rated 7/10), Cape Henlopen High School (rated 8/10), Rehoboth Elementary School (rated 8/10).

Does 8 Chicago St have air conditioning?

Yes, 8 Chicago St in Dewey Beach, DE has air conditioning.

How big is the lot at 8 Chicago St?

The lot at 8 Chicago St in Dewey Beach, DE is about 0.23 acres (10,001 sq ft).

Does 8 Chicago St have a garage?

Yes, 8 Chicago St in Dewey Beach, DE has a garage.

OFF MARKET

$2,576,500

Trulia Estimate

4 Beds
2,754 sqft

8 Chicago St, Dewey Beach, DE 19971

Est. Refi. Payment $14,442/mo*

Refinance Your Home

Home Value

Trulia Estimate

$2.58M

Since last month

$130K (-5.1%)

Since last year

$220K (+10%)

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 decreased by -3% in the last 10 years

Month	Estimated value
2026
September 2026	$2.41M
August 2026	$2.58M
July 2026	$2.55M
June 2026	$2.61M
May 2026	$2.35M
April 2026	$2.61M
March 2026	$2.25M
February 2026	$2.05M
January 2026	$2M
2025
December 2025	$2.28M
November 2025	$2.43M
October 2025	$2.13M
September 2025	$2.16M
August 2025	$2.2M
July 2025	$2.21M
June 2025	$2.26M
May 2025	$2.08M
April 2025	$2.21M
March 2025	$2.08M
February 2025	$2.08M
January 2025	$2.07M
2024
December 2024	$2.12M
November 2024	$2.19M
October 2024	$2.41M
September 2024	$2.4M
August 2024	$2.41M
July 2024	$2.23M
June 2024	$2.22M
May 2024	$2.34M
April 2024	$2.26M
March 2024	$2.16M
February 2024	$2.23M
January 2024	$2.2M
2023
December 2023	$2.06M
November 2023	$2.13M
October 2023	$2.14M
September 2023	$2.09M
August 2023	$2.18M
July 2023	$2.23M
June 2023	$2.18M
May 2023	$2.33M
April 2023	$2.31M
March 2023	$2.27M
February 2023	$2.18M
January 2023	$2.18M
2022
December 2022	$2.26M
November 2022	$2.39M
October 2022	$2.43M
September 2022	$2.45M
August 2022	$2.44M
July 2022	$2.54M
June 2022	$2.59M
May 2022	$2.6M
April 2022	$2.55M
March 2022	$2.54M
February 2022	$2.56M
January 2022	$2.52M
2021
December 2021	$2.54M
November 2021	$2.59M
October 2021	$2.6M
September 2021	$2.57M
August 2021	$2.64M
July 2021	$2.71M
June 2021	$2.68M
May 2021	$2.68M
April 2021	$2.64M
March 2021	$2.45M
February 2021	$2.38M
January 2021	$2.5M
2020
December 2020	$2.5M
November 2020	$2.44M
October 2020	$2.37M
September 2020	$2.35M
August 2020	$2.48M
July 2020	$2.48M
June 2020	$2.42M
May 2020	$2.38M
April 2020	$2.45M
March 2020	$2.52M
February 2020	$2.5M
January 2020	$2.55M
2019
December 2019	$2.54M
November 2019	$2.47M
October 2019	$2.55M
September 2019	$2.82M
August 2019	$2.71M
July 2019	$2.75M
June 2019	$2.81M
May 2019	$2.63M
April 2019	$2.58M
March 2019	$2.58M
February 2019	$2.71M
January 2019	$2.83M
2018
December 2018	$2.6M
November 2018	$2.89M
October 2018	$2.63M
September 2018	$2.69M
August 2018	$2.68M
July 2018	$2.75M
June 2018	$2.64M
May 2018	$2.85M
April 2018	$2.74M
March 2018	$2.81M
February 2018	$2.67M
January 2018	$2.57M
2017
December 2017	$2.58M
November 2017	$2.75M
October 2017	$2.69M
September 2017	$2.71M
August 2017	$2.82M
July 2017	$2.82M
June 2017	$2.78M
May 2017	$2.69M
April 2017	$2.45M
March 2017	$2.54M
February 2017	$2.73M
January 2017	$2.5M
2016
December 2016	$2.56M
November 2016	$2.5M
October 2016	$2.56M
September 2016	$2.48M

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
2 Chicago St, Dewey Beach, DE	0.02	Single-Family Home	$4,700,000	05/01/26	6	5.5	2,666
110 Jersey St, Dewey Beach, DE	0.17	Single-Family Home	$2,075,000	09/18/25	3	-	2,842
23 Jersey St, Dewey Beach, DE	0.14	Single-Family Home	$2,900,000	01/30/26	4	3.5	2,300
16 Chicago St, Dewey Beach, DE	0.04	Single-Family Home	$4,935,000	09/10/26	5	5	4,500
15 West St, Dewey Beach, DE	0.05	Single-Family Home	$839,700	03/27/26	7	5	3,600
107 Swedes St, Dewey Beach, DE	0.25	Single-Family Home	$2,075,000	04/22/26	5	3.5	2,600
111 Jersey St, Dewey Beach, DE	0.19	Single-Family Home	$1,325,000	12/04/25	3	2	2,200
114 Chesapeake St, Dewey Beach, DE	0.25	Single-Family Home	$2,110,000	01/08/26	4	3	2,000
103 Carolina St, Dewey Beach, DE	0.20	Single-Family Home	$2,075,000	04/13/26	4	3.5	1,600
1602 Bayard Ave, Dewey Beach, DE	0.22	Single-Family Home	$1,335,000	05/21/26	4	2	1,516

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
2 Chicago St, Dewey Beach, DE 19971	0.02	$4,700,000	6	5.5	2,666	Recently Sold
16 Chicago St, Dewey Beach, DE 19971	0.04	$4,935,000	5	5	4,500	Recently Sold
17 Saint Louis St, Dewey Beach, DE 19971	0.09	$2,700,600	6	5.5	3,500	Off Market
24 West St, Dewey beach, DE 19971	0.09	$1,475,000	3	1.5	1,120	For Sale
20 Saint Louis St, Dewey Beach, DE 19971	0.11	$2,872,900	4	2	1,508	Off Market
102 West St, Dewey Beach, DE 19971	0.12	$1,616,500	6	3	2,000	Off Market
1252 King Charles Ave, Dewey Beach, DE 19971	0.12	-	-	-	-	Off Market
21 Houston St #7, Rehoboth Beach, DE 19971	0.13	$460,000	1	1	400	Recently Sold
105 Chicago St, Dewey Beach, DE 19971	0.13	$4,200,000	7	7	7,136	For Sale
21 Houston St #10, Rehoboth Beach, DE 19971	0.14	$575,000	2	1	550	Recently Sold
23 Jersey St, Dewey Beach, DE 19971	0.14	$2,900,000	4	3.5	2,300	Recently Sold
16 Houston St #E, Dewey Beach, DE 19971	0.15	$1,351,200	4	3	2,328	Off Market

Local Information

Map ViewExplore the area around 8 Chicago St.
Schools1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 2000

2,754 sqft

$936/sqft

Garage

About this House

This single-family home is located at 8 Chicago St, Dewey Beach, DE. 8 Chicago St is in Dewey Beach, DE and in ZIP code 19971. This property has 4 bedrooms and approximately 2,754 sqft of floor space. This property has a lot size of 10001 sqft and was built in 2000.

8 Chicago St, Dewey Beach, DE 19971 is a 4 bedroom, 2,754 sqft single-family home built in 2000. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,576,500, with a rent estimate of $2,640/month.

Home Details for 8 Chicago St

Interior Features
Interior Details BasementNumber of Rooms: 7
Heating & Cooling Heating: Forced AirCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 1
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: Other, WoodFoundation Type: Piers
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 2000
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 10001 sqft

Price and Tax history

Year	Property tax	Tax assessment
2025	$5,211	$2,316,600

Home facts updated by county records

Additional Cost

Market trends in Dewey Beach

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Around this home

Rehoboth Elementary School
K-5
Public
Cape Henlopen School District
8/10
GreatSchools Rating
Parent Rating Average
We moved here from Maryland 2 years ago. Rehoboth Elementary is the absolute best school I could of ever hoped for! The teachers and staff work hard to help students who are behind and help build confidence in these kiddos as well! My son was bullied and teased at the school he attended in Maryland and it broke my heart to hear him come home and tell me how kids picked on him for his reading (kindergarten)! I am so glad we moved here because we have not experienced anything bad whatsoever! This is the place we want to call home all because of Rehoboth Elementary! #foreveraviking #thisisourhome #weloveourschool #weloveourteachers #capehenlopenschooldistrict
Parent Review
5y ago
3 Reviews

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Dewey Beach

Trulia User
Resident
5y ago
"Dogs and family friendly. Would recommend this area to anyone I know. If you’re looking to live here have no doubts it’s an awesome community. "
0
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Ddeneating
Visitor
7y ago
"Lots of dogs around. Greyhounds reach the beach in October, can be on the beach after October 1st. "
3
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Joeschantz
Resident
8y ago
"Nearness to the ocean and bay. Great entertainment venue. Good water sports in ocean and bay. Good restaurants."
0
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LGBTQ Local Legal Protections

Frequently asked questions about 8 Chicago St

What is 8 Chicago St estimated to be worth?
Trulia's estimated value for 8 Chicago St in Dewey Beach, DE is $2,576,500.
Is Dewey Beach a buyer's or seller's market?
Dewey Beach is currently a balanced market, based on recent for-sale activity.
What are the closest schools to 8 Chicago St?
The closest schools to 8 Chicago St in Dewey Beach, DE are Beacon Middle School (rated 7/10), Cape Henlopen High School (rated 8/10), Rehoboth Elementary School (rated 8/10).
Does 8 Chicago St have air conditioning?
Yes, 8 Chicago St in Dewey Beach, DE has air conditioning.
How big is the lot at 8 Chicago St?
The lot at 8 Chicago St in Dewey Beach, DE is about 0.23 acres (10,001 sq ft).
Does 8 Chicago St have a garage?
Yes, 8 Chicago St in Dewey Beach, DE has a garage.

Apartments for Rent

Skip to last item

$2,000/mo
2 bd
2 ba
4100 Sand Piper Dr #4105,
Rehoboth Beach, DE 19971
NEW - 7 HRS AGO
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$2,200/mo
3 bd
2 ba
37696 Ulster Dr #6,
Rehoboth Beach, DE 19971
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$3,000/mo
1 bd
1 ba
36 Maryland Ave #C,
Rehoboth Beach, DE 19971
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$4,500/mo
4 bd
3 ba
36 Maryland Ave #A,
Rehoboth Beach, DE 19971
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$2,300/mo
3 bd
3 ba
1000 Talon Dr #3,
Rehoboth Beach, DE 19971
APPLY INSTANTLY
FURNISHED
$2,300/mo
2 bd
2 ba
250 Sea Eagle Dr #7,
Rehoboth Beach, DE 19971
APPLY INSTANTLY
FURNISHED
$1,800/mo
2 bd
2 ba
3400 Sanibel Cir #3402,
Rehoboth Beach, DE 19971
APPLY INSTANTLY
FURNISHED
$2,000/mo
3 bd
2 ba
18 Eagles Lndg #1809,
Rehoboth Beach, DE 19971
APPLY INSTANTLY
FURNISHED
$1,800/mo
2 bd
2 ba
3600 Sanibel Cir #3609,
Rehoboth Beach, DE 19971
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Off Market Homes Near 8 Chicago St

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SOLD
SEP 11, 2026
$3,645,000
5 bd
5.5 ba
2,765 sqft
109 Stockley St,
Rehoboth Beach, DE 19971
Jack Lingo - Rehoboth
SOLD
SEP 10, 2026
$1,750,000
4 bd
3.5 ba
2,000 sqft
13 Clayton St #5,
Dewey Beach, DE 19971
Coldwell Banker Premier - Rehoboth
SOLD
SEP 8, 2026
$1,735,000
5 bd
5 ba
3,789 sqft
22775 Keel Ct #15,
Rehoboth Beach, DE 19971
Monument Sotheby's International Realty
SOLD
SEP 3, 2026
$1,675,000
3 bd
3 ba
1,277 sqft
21170 1st St,
Rehoboth Beach, DE 19971
Jack Lingo - Rehoboth
SOLD
AUG 31, 2026
$2,400,000
5 bd
4.5 ba
3,425 sqft
14 Fillingame Way,
Rehoboth Beach, DE 19971
Jack Lingo - Rehoboth
SOLD
AUG 30, 2026
$2,525,000
4 bd
2 ba
2,217 sqft
518 New Castle Street Ext,
Rehoboth Beach, DE 19971
Jack Lingo - Rehoboth
SOLD
AUG 28, 2026
$2,211,500
4 bd
3.5 ba
2,334 sqft
23 Sheffield Rd,
Rehoboth Beach, DE 19971
Monument Sotheby's International Realty
SOLD
AUG 26, 2026
$1,625,000
5 bd
4.5 ba
3,628 sqft
106 Cambridge Way,
Rehoboth Beach, DE 19971
Jack Lingo - Lewes
SOLD
AUG 24, 2026
$1,699,000
2 bd
2.5 ba
1,024 sqft
11 S Rodney Dr,
Rehoboth Beach, DE 19971
Jack Lingo - Rehoboth
SOLD
AUG 21, 2026
$1,978,774
3 bd
3,012 sqft
1018 Scarborough Avenue Ext,
Rehoboth Beach, DE 19971
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Homes for sale near 8 Chicago St

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$1,500,000
4 bd
2 ba
1,850 sqft
117 Cullen St,
Dewey beach, DE 19971
Rehoboth Bay Realty, Co.
$3,995,000
6 bd
3.5 ba
3,200 sqft
7 Sand Dunes Dr,
Dewey Beach, DE 19971
Monument Sotheby's International Realty
$1,475,000
3 bd
1.5 ba
1,120 sqft
24 West St,
Dewey beach, DE 19971
Jack Lingo - Rehoboth
$4,200,000
7 bd
7 ba
7,136 sqft
105 Chicago St,
Dewey Beach, DE 19971
Mann & Sons, Inc.
NEW CONSTRUCTION
$4,700,000
5 bd
5 ba
1,004 sqft
24 Houston St,
Dewey Beach, DE 19971
Houwzer
NEW CONSTRUCTION
$1,969,000
5 bd
4.5 ba
3,514 sqft
38340 Josephine St,
Rehoboth Beach, DE 19971
Compass
$1,999,000
4 bd
3 ba
808 sqft
21095 Elizabeth Ave,
Rehoboth Beach, DE 19971
Patterson-Schwartz-Brandywine
NEW CONSTRUCTION
$3,599,900
6 bd
6 ba
4,600 sqft
104 Buena Rd,
Dewey Beach, DE 19971
Empower Real Estate, LLC
$1,950,000
5 bd
5.5 ba
3,399 sqft
38175 Robinsons Dr,
Rehoboth Beach, DE 19971
Patterson-Schwartz-Rehoboth
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