2 Chicago St, Dewey Beach, DE 19971
Property image
Property image
SOLD
MAY 1, 2026

$4,702,700

Trulia Estimate
  • 6 Beds
  • 5.5 Baths
  • 2,666 sqft

2 Chicago St, Dewey Beach, DE 19971

Est. Refi. Payment $26,499/mo*
Refinance Your Home
Currently Off Market - Sold May 1, 2026 for $4,700,000 (2% below list price)

Home Value

Trulia Estimate
$4.7M
Since last month
Increased$4K (+0.1%)
Since last year
Decreased$577K (-10.9%)
Since last sale
$900 (0%)
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 +47% in the last 10 years
MonthEstimated value
2026
September 2026$4.7M
August 2026$4.7M
July 2026$4.69M
June 2026$4.69M
May 2026$4.7M
April 2026$4.42M
March 2026$4.43M
February 2026$4.41M
January 2026$4.78M
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
16 Chicago St, Dewey Beach, DE
0.06
Single-Family Home
$4,935,000
09/10/26
5
5
4,500
23 Jersey St, Dewey Beach, DE
0.15
Single-Family Home
$2,900,000
01/30/26
4
3.5
2,300
107 Swedes St, Dewey Beach, DE
0.26
Single-Family Home
$2,075,000
04/22/26
5
3.5
2,600
103 Carolina St, Dewey Beach, DE
0.21
Single-Family Home
$2,075,000
04/13/26
4
3.5
1,600
807 King Charles Ave, Rehoboth Beach, DE
0.71
Single-Family Home
$3,975,000
10/30/25
5
5.5
2,801
21008 Dodd Ave, Rehoboth Beach, DE
0.31
Single-Family Home
$1,612,490
05/11/26
8
4
2,184
3A Rodney St, Rehoboth Beach, DE
0.70
Single-Family Home
$4,675,000
08/28/26
4
4.5
2,980
114 Chesapeake St, Dewey Beach, DE
0.25
Single-Family Home
$2,110,000
01/08/26
4
3
2,000

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
16 Chicago St, Dewey Beach, DE 19971
0.06
$4,935,000
5
5
4,500
Recently Sold
17 Saint Louis St, Dewey Beach, DE 19971
0.10
$2,709,400
6
5.5
3,500
Off Market
24 West St, Dewey beach, DE 19971
0.11
$1,475,000
3
1.5
1,120
For Sale
20 Saint Louis St, Dewey Beach, DE 19971
0.12
$2,888,100
4
2
1,508
Off Market
102 West St, Dewey Beach, DE 19971
0.14
$1,673,600
6
3
2,000
Off Market
1252 King Charles Ave, Dewey Beach, DE 19971
0.14
-
-
-
-
Off Market
21 Houston St #7, Rehoboth Beach, DE 19971
0.14
$460,000
1
1
400
Recently Sold
105 Chicago St, Dewey Beach, DE 19971
0.14
$4,200,000
7
7
7,136
For Sale
21 Houston St #10, Rehoboth Beach, DE 19971
0.15
$575,000
2
1
550
Recently Sold
23 Jersey St, Dewey Beach, DE 19971
0.15
$2,900,000
4
3.5
2,300
Recently Sold
16 Houston St #E, Dewey Beach, DE 19971
0.16
$1,389,300
4
3
2,328
Off Market

Local Information

  • Map ViewExplore the area around 2 Chicago St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1988
2,666 sqft
$1,763/sqft
Open Parking

About this House

Rare oceanfront opportunity in Rehoboth by the Sea. Discover unparalleled coastal living at 2 Chicago Street, an oceanfront retreat in the highly coveted community of Rehoboth by the Sea on the north end of Dewey Beach. This exceptional 6-bedroom, 5.5-bath home offers sweeping panoramic views from nearly every room, with a private dune crossover that leads directly to the wide, sandy beach. The first level welcomes you with a bright entry foyer, two bedrooms (including a flexible oceanfront space ideal for a den, exercise room, or guest suite), two full baths, and a convenient laundry room. Upstairs, the recently updated kitchen shines with quartz counters, stainless steel appliances, and custom cabinetry, seamlessly flowing into the dining and living areas—all framed by walls of windows showcasing endless ocean vistas. Step outside to the expansive oceanfront deck, perfect for sunrises, gatherings, and salty breezes. A private office with sweeping north-facing views completes this level. On the third floor, you’ll find four additional bedrooms and three full baths, including the oceanfront primary suite with its own balcony for uninterrupted sunrise views. The rooftop deck crowns the home, offering a bird’s-eye view of the coastline—an unforgettable setting for stargazing or enjoying fireworks on July 4th. Rehoboth by the Sea is one of the Delaware coast’s most sought-after neighborhoods, known for its wide beaches, relaxed atmosphere, and close proximity to both Rehoboth and Dewey Beach attractions. Currently, 2 Chicago Street stands as the only oceanfront property available in either community—making this a truly rare opportunity to own a piece of coastal paradise.
2 Chicago St, Dewey Beach, DE 19971 is a 6 bedroom, 6 bathroom, 2,666 sqft single-family home built in 1988. It last sold for $4,700,000 on May 1, 2026 (2% below the $4,795,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,702,700.
Last check for updates: about 10 hours ago
Listed by SHAUN TULL, (302) 226-6417
Jack Lingo - Rehoboth
Listing Team: Bryce Lingo & Shaun Tull Team, Co-Listing Team: Bryce Lingo & Shaun Tull Team,Co-Listing Agent: Bryce Lingo, (302) 226-6417
Jack Lingo - Rehoboth
Bought with: Brian Barrows, (302) 227-6767, Monument Sotheby's International Realty
Co-Buyer's Agent: JENN BARROWS, (302) 227-6767, Monument Sotheby's International Realty
Source: Bright MLS, MLS#DESU2077352

Home Details for 2 Chicago St

Interior Features

Interior Details
Number of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 6Main Level Bedrooms: 2Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 2666 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Sewer Available, Water Available, CableAppliances: Exhaust Fan, Range Hood, Oven/Range - Electric, Dishwasher, Disposal, Dryer, Microwave, Washer, Refrigerator, Ice Maker, Electric Water HeaterDishwasherDisposalDryerLaundry: Lower LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,Zoned,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Bay/Bow, Double Hung, Window TreatmentsFlooring: Ceramic Tile, Wood
Levels, Entrance, & Accessibility
Stories: 3Levels: ThreeAccessibility: NoneFloors: Ceramic Tile, Wood
View
Has a ViewView: Ocean, Panoramic
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Deck, Porch, Roof, Roof DeckOther Structures: Above Grade, Below GradeExterior: Rain Gutters, Outdoor Shower, BalconyFoundation: SlabNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 3Parking: Asphalt,Crushed Stone,Off Street
Pool
Pool: None
Frontage
WaterfrontWaterfront: Sandy Beach, Oceanfront, Beach Access, OceanResponsible for Road Maintenance: City/CountyOn Waterfront
Water & Sewer
Sewer: Public SewerWater Body: Atlantic Ocean
Farm & Range
Frontage Length: Water Frontage Ft: 50
Finished Area
Finished Area (above surface): 2666 Square Feet

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Coastal,Contemporary
Building
Building Name: None AvailableConstruction Materials: FrameNot a New ConstructionNo Additional Parcels
Property Information
Condition: Very GoodNot Included in Sale: Artwork, Some Furniture, And Staging ItemsIncluded in Sale: Some FurnishingsParcel Number: 33420.14156.00

Price & Status

Price
List Price: $4,795,000Price Per Sqft: $1,763/sqft
Status Change & Dates
Off Market Date: Fri May 01 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Media

Location

Direction & Address
City: DEWEY BEACHCommunity: Rehoboth By The Sea
School Information
Elementary School District: Cape HenlopenJr High / Middle School District: Cape HenlopenHigh School District: Cape Henlopen

Building

Building Area
Building Area: 2666 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 5000 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: DESU2077352Water ViewWater View: OceanAbove Grade Unfinished Area: 2666

Additional Information

Source Internet Entire Listing Display: Y

Price and Tax history

DateEventPrice
May 1, 2026
Source: Bright MLS #DESU2077352
Sold
$4,700,000
Mar 11, 2026
Source: Bright MLS #DESU2077352
Contingent
$4,795,000
Feb 27, 2026
Source: Bright MLS #DESU2077352
PriceChange
$4,795,000
Price decreased by 4%
Feb 14, 2026
Source: Bright MLS #DESU2077352
PriceChange
$4,995,000
Price decreased by 4%
Nov 10, 2025
Source: Bright MLS #DESU2077352
PriceChange
$5,200,000
Price decreased by 4%

Market trends in Dewey Beach

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
7
2MoM

Around this home

What Locals Say about Dewey Beach

  • Trulia User
    "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
    Flag
  • Ddeneating
    "Lots of dogs around. Greyhounds reach the beach in October, can be on the beach after October 1st. "
    3
    Flag
  • Joeschantz
    "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

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Frequently asked questions about 2 Chicago St

  • What is 2 Chicago St estimated to be worth?
    Trulia's estimated value for 2 Chicago St in Dewey Beach, DE is $4,702,700.
  • What is the price history for 2 Chicago St?
    2 Chicago St in Dewey Beach, DE last sold for $4,700,000 in May 2026.
  • 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 2 Chicago St?
    The closest schools to 2 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 2 Chicago St have air conditioning?
    Yes, 2 Chicago St in Dewey Beach, DE has air conditioning.
  • Does 2 Chicago St have laundry facilities?
    Yes, 2 Chicago St in Dewey Beach, DE has in-unit laundry.

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