Property photo 1
Property photo 2
Property photo 3
Property photo 4
Property photo 5
4 Beds
2 Baths

$914,990

33140 MAIN STREET, DAGSBORO DE, 19939

Price per sqftN/A
Built in1920
Property typeResidential

Overview

Active

Active-bright

Listed May 1, 2026

Updated 4 days ago

For the very first time, Dagsboro's most recognizable home has arrived on the public market. This quintessential 1920s American Foursquare with its signature porte-cochère is as storied, charming, and full of personality as the white-hot town it calls home. You've driven past it. Everyone has. Now it's your opportunity to call it home! Perfectly positioned in the heart of downtown Dagsboro — steps from Porto's beloved flavors, a short stroll to the legendary Clayton Theatre, and just minutes from coffee, Jaynes Reliable, the botanical gardens and the local gems that give this community its undeniable soul — this property sits at the crossroads of small-town charm and serious opportunity. And with Bethany Beach just a quick drive away - you are connected to small town and sea. Welcomed by the wraparound porch, made for slow summer evenings, sweet tea in hand, waving to neighbors who have always admired this home from the street. Step inside and be instantly transported — but with all the modern upgrades you'd expect. Warm, thoughtfully refinished red oak hardwood floors flow beneath crisp white walls in a living room that is grand in scale and spirit. A local craftsman's custom crown molding, bespoke radiator covers, and a beautifully trimmed fireplace pay reverent homage to the home's historic character. Twin symmetrical curved alcove shelves usher you into a bayed dining room appointed with a built-in corner hutch, a vintage chandelier dripping with charm, and glass pocket doors. You will also notice original glass doorknobs throughout the home and substantial wood millwork original to the home has been lovingly maintained. The large eat-in kitchen impresses with vaulted ceilings that flood the space with light and air, abundant cabinetry, a center island, dual sinks, and solid surface countertops. Just off the kitchen, an all-season sunroom offers serene views of the landscaped courtyard — your own private oasis. Before heading upstairs, discover a stunning library/study adorned with custom milled, illuminated built-ins — designed and carefully executed by a local carpenter. This home could easily be converted into a primary bedroom on this level. A spacious bathroom with a soaking tub is conveniently adjacent. The second floor delivers a generously proportioned primary suite, three additional bedrooms, and a full bath. A full staircase leads to the floored attic, ready to be finished into an additional bedroom and bath. Below, a full basement provides ample storage. Outside, the possibilities multiply: a charming tiny house with plumbing for a full bath, and a substantial barn featuring two garage doors and a large second-floor — perfectly suited for a two-bedroom apartment (with applicable zoning and local approvals). Set on around 2 acres zoned TC (Town Center), this 2.13 -acre landmark property is as versatile as it is beautiful — continue its legacy as a private residence, or reimagine it as a coffee shop, boutique, law office, wellness studio, bed & breakfast, or any number of commercial uses. The bones? Impeccable. The opportunity? Unmatched. Dagsboro is an ever growing downtown town with close proximity to the nearby cities of Georgetown, Berlin, Ocean City, Salisbury Maryland and the nearby coastal towns of Bethany Beach and Fenwick Island.

$6,087/mo

Est. mortgage payment based on a $914,990 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
DESU2107882

Interior Features

Bedrooms
4
Bathrooms
2
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
2.13 Acres

Other Property Details

Taxes
$1,266
Tax Frequency
Annually
Garage
Yes
55+/Senior Community
No
MLS provider logo

Listed by Monument Sotheby's International Realty
Listing Contact: 3028977499 

The IDX display contains information sourced from the Bright MLS, Inc. as of 10/6/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

©2026 Bright MLS, Inc. all rights reserved.

Data last updated on 10/6/2026 at 4:33 AM UTC

 

Compass

Powered by Luxury Presence