2 Chicago St
Dewey Beach, DE 19971
6 Beds
5.5 Baths
2,666 sqft
$4,700,000
Last Sold: May 1, 2026
2% below list $4.79M
$1,763/sqft
Est. Refi. Payment $25,357/mo*
$4,700,000
Last Sold: May 1, 2026
2% below list $4.79M
$1,763/sqft
Est. Refi. Payment $25,357/mo*
6 Beds
5.5 Baths
2,666 sqft
Local Information
- Map ViewExplore the area around 2 Chicago St.
- Schools1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1988
Living Area
2,666 sqft
Price/Sqft
$1,763/sqft
Parking
Open Parking
Description
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). It is currently off market. The Trulia Estimate is $4,683,800, with a rent estimate of $3,007/month.
Home Details for 2 Chicago St
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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) |
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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 |
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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 |
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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 |
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MLS Status: CLOSED |
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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 |
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Building Area Building Area: 2666 Square Feet |
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Not Senior Community |
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No HOA |
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Lot Area: 5000 sqft |
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Special Conditions: Standard |
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Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional |
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Business Information Ownership: Fee Simple |
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Mls Number: DESU2077352Water ViewWater View: OceanAbove Grade Unfinished Area: 2666 |
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Source Internet Entire Listing Display: Y |
Last check for updates: about 12 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
Price History for 2 Chicago St
| Date | Price | Event | Source |
|---|---|---|---|
| 05/01/2026 | $4,700,000 | Sold | Bright MLS #DESU2077352 |
| 03/11/2026 | $4,795,000 | Contingent | Bright MLS #DESU2077352 |
| 02/27/2026 | $4,795,000 | PriceChange | Bright MLS #DESU2077352 |
| 02/14/2026 | $4,995,000 | PriceChange | Bright MLS #DESU2077352 |
| 11/10/2025 | $5,200,000 | PriceChange | Bright MLS #DESU2077352 |
| 09/26/2025 | $5,400,000 | Listed For Sale | Bright MLS #DESU2077352 |
| 02/15/2013 | $2,800,000 | Sold | N/A |
Market trends in Dewey Beach
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
7
3MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $6,448 |
| Assessment | $2,902,300 |
Home facts updated by county records
Comparable Sales for 2 Chicago St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.15 | Single-Family Home | $2,900,000 | 01/30/26 | 4 | 3.5 | 2,300 | |
0.26 | Single-Family Home | $2,075,000 | 04/22/26 | 5 | 3.5 | 2,600 | |
0.21 | Single-Family Home | $2,075,000 | 04/13/26 | 4 | 3.5 | 1,600 | |
0.14 | Single-Family Home | $995,000 | 08/21/25 | 6 | 3 | 2,000 | |
0.71 | Single-Family Home | $3,975,000 | 10/30/25 | 5 | 5.5 | 2,801 | |
0.31 | Single-Family Home | $1,612,490 | 05/11/26 | 8 | 4 | 2,184 | |
0.25 | Single-Family Home | $2,110,000 | 01/08/26 | 4 | 3 | 2,000 | |
0.38 | Single-Family Home | $5,850,000 | 12/16/25 | 6 | 6.5 | 4,607 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETJack Lingo - Rehoboth
SOLDJAN 12, 2026Long & Foster Real Estate, Inc.
SOLDMAY 1, 2026360 PROPERTY SOLUTIONS
FOR SALEMark L Handler Real Estate
SOLDJAN 30, 2026Jack Lingo - Rehoboth
OFF MARKETNon Subscribing Office
OFF MARKETJack Lingo - Rehoboth
Assigned Schools
These are the assigned schools for 2 Chicago St.
- Cape Henlopen High School
- 9-12
- Public
- 1889 Students
8/10GreatSchools RatingParent Rating AverageFrom what I've heard from my students, who attend as well as close by families and friends, there is a lot that goes on behind the scenes here. This district is known to hide major incidents, as they don't want anyone to know what is actually going on. Administration is not up to far, from many locals perspectives ( the principal, not the vice) the principal is less than personable, and seems to think she is something else. Chasing the very best teachers in Cape district to other schools. She needs to go! She seems miserable, and her face shows....Parent Review6mo ago - Rehoboth Elementary School
- K-5
- Public
- 557 Students
8/10GreatSchools RatingParent Rating AverageWe 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 #capehenlopenschooldistrictParent Review5y ago - Beacon Middle School
- 6-8
- Public
- 427 Students
7/10GreatSchools RatingParent Rating AverageHorrible, horrendous, absolutely disgusted with this school. As a matter of fact I cannot think of one nice thing to say about it. The education was poor, the verbal attacks are ignored, the teachers are second rate at best, this school is the bottom of the bottom.Parent Review7y ago 
Check out schools near 2 Chicago St.
What Locals Say about Dewey Beach
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