Explore Rehoboth Beach, DE Homes for Sale

Homes for Sale with a Guest House in Rehoboth Beach, DE

Welcome to your dedicated resource for homes for sale with a guest house in Rehoboth Beach, DE. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Rehoboth Beach, DE agent, Coastal Homestead Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a guest house properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Guest House in Rehoboth Beach, DE

5 Beds ⋅ 3 Baths

Do you dream of being close to the beach (just blocks!)? Want charm? Want rental possibilities? Then you need to see this property! With only 2 owners in its entire history, the main house oozes charm and easy beach living. Just imagine sitting on the front screened porch having a morning cup of coffee and thinking about strolling to the beach just a few blocks away. Details like true hardwood floors, doors and trim are original wood, arched doorways are still present. BR3 upstairs was expanded several years ago to include a sitting area & balcony & the added full bath that is shared. In the main house Kitchen there is a W/D hookup in the kitchen nook. The huge rear deck is shared between the house and cottage, can't you envision a BBQ for friends and family here? An outside shower keeps the sand outside! The cottage has a full eat-in kitchen, bedroom & living spaces, walk-in closet (that's an understatement!) & storage, and full bath. The cottage and house share the 'garage' space as storage and the washer dryer are located here. Have guests stay (or rent it out!) in the 1BR rear cottage .. you choose! The cottage was a long term rental for several years, so the USPS gave the cottage its own mailing address (38419 George St) but it is ALL ONE property. This is a phenomenal opportunity to be blocks to the beach, downtown Dewey and Rehoboth! Don't miss this one!

38417 George St, Rehoboth Beach

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (302) 539-9040

6 Beds ⋅ 5 Baths

6-7 bedrooms and 5 full baths! Amazing location; East of Route 1. A refined coastal retreat wrapped in lush, European‑sculpted greenery, this residence at 41218 Gloucester Drive delivers privacy, elegance, and a curated sense of arrival that sets it apart in Rehoboth Beach’s most desirable enclave. The moment you approach the property; the landscaping becomes the signature. Hand‑sculpted European trees—shaped with the precision of formal gardens in Provence or Lake Como—create a natural architectural frame around the home. Their tiered canopies and sculpted silhouettes offer Estate‑level privacy without sacrificing sunlight. Old‑World Garden character that elevates curb appeal. The rear yard has sound‑buffering greenery ideal for serene outdoor living. This is landscaping as luxury design, not decoration. The backyard unfolds like a private European courtyard—intimate, green, and beautifully composed. The sculpted trees create natural “rooms” outdoors, perfect for: Al fresco dining under manicured canopies, enjoy morning coffee with the hummingbirds. This is outdoor living designed for both tranquility and entertaining. The first floor features a stunning two-story family room with stone fireplace, coffered ceilings, and hand scraped hardwood floors, The chef’s kitchen is accented by a 5-burner cooktop, large island, quartz counter & backsplash, lots of cabinets, and walk-in pantry. Rounding out the first floor is a dedicated office/den with full bath, and the primary bedroom complete with tray ceiling, expansive walk-in closet with built ins and primary bathroom with soaking tub, shower, and dual vanities. Head upstairs and you will find a large loft living area, a second bedroom that has a private full bath as well as a third bedroom connected to a full bath and fourth bedroom. The finished basement features a large open area with a full kitchen, dining room, living room, 2 bedrooms, a full bath, and storage room. The home has a large private composite deck with dual arbors, custom lighting. fenced back yard, lush landscaping. and irrigated lawn with an AG well. There is an oversized garage with a large storage alcove. Just 1 mile to restaurants, shopping, Downtown Rehoboth Beach and 2 miles to the Boardwalk and beach. Walk or bike the adjacent Junction and Breakwater Trail with miles of trails that connect Rehoboth, Lewes, Cape Henlopen State Park. The community offer two pools, tennis, fitness centers, and waterfront park. The HOA cuts and fertilizes your lawn which gives you more time to relax. Come enjoy this amazing lifestyle. Owners are licensed DE Realtors.

41218 Gloucester Dr, Rehoboth Beach

Listing courtesy of RE/MAX Realty Group Rehoboth. Contact: 3022274800

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