Chesapeake Beach, MD Homes for Sale under $500,000

This beautiful split level home with lots of space, a large back deck, breakfast nook/ dining room, detached garage, a carport and more. This home highlights the incredible care and maintenance shown over the last 14 years. The roof on the second level replaced in 2014, the main and garage roof replaced in 2025 as well as a new skylight and insulation. Retaining walls replaced in 2017. Brand new

James Dick Long & Foster Real Estate, Inc.

Location, Location, Location! Enjoy the best of coastal living just minutes from the Chesapeake Bay, boardwalk, and fishing pier. Ideally positioned less than five minutes from the beach, Chesapeake Beach Railway Trail, and the charming waterfront towns of North Beach and Chesapeake Beach, this home places you right in the heart of it all. Welcome to your new home! This well-maintained 3-bedroom,

Bonnie O'Donnell RE/MAX One

Open House Saturday, April 4th 10-12!Welcome to 2401 Green Leaf Terrace in Chesapeake Beach! This well-maintained end-unit townhome offers 4 bedrooms, including a basement bedroom that provides great flexibility for guests, a home office, or additional living space, along with 2 full baths and 1 half bath. SELLERS OFFERING A FLOORING CREDIT!! Backing to trees for added privacy, the home

Lindsey Burch Samson Properties

Great price for this 4-Level home with a total of 2,482 sf -- including 447 sf of unfinished storage space on bottom level! Almost one acre (.81) of land surrounded by mature trees and in great Northern Calvert location of top-rated schools. Kitchen has stainless steel appliances, and has real wood cabinets that a new owner could paint to easily update! Kitchen has a pantry, a breakfast bar and

Conor Stueckler Keller Williams Flagship

Nestled in the charming community of The Highlands, this delightful Colonial-style home offers a perfect blend of comfort and convenience. This well-maintained residence boasts 1,860 square feet of inviting living space, featuring four spacious bedrooms and two and a half bathrooms. The heart of the home is a cozy living area with a warm fireplace, ideal for creating lasting memories with loved

Kelly DePaulo Keller Williams Capital Properties

This 5-bedroom, 3-bathroom home is ready for new owners! Located on a quiet cul-de-sac with a huge fenced-in backyard and a spacious deck off the kitchen. Convenient Chesapeake Beach location, close to the Chesapeake Bay, and all the amenities that Chesapeake Beach has to offer! Bayfront Park, shopping, restaurants, the water park, ballparks, playgrounds, community center, marina, boardwalks, and

Mike Benton Home Towne Real Estate

Coming soon! Open House 04/19/2026 from 12noon-3pm.Experience refined coastal living in this impeccably maintained 4-bedroom, 2-bath residence, gracefully situated on a private 2-acre lot in the prestigious Highlands community of Chesapeake Beach. Tucked away on a quiet cul-de-sac, this exceptional property offers a rare combination of tranquility, space, and understated elegance—all with a

Jana Ritter Ritter Realty, LLC

This beautifully updated home offers 2,450 finished square feet on over half an acre in a sought-after community of the Highlands in Chesapeake Beach! Has luxury vinyl plank flooring and an abundance of natural light throughout the open floor plan. The updated kitchen showcases quartz countertops, stainless steel appliances, a gooseneck faucet, and a built-in microwave. Convenient sliders lead to

Team Stueckler Keller Williams Flagship

Welcome to this beautifully maintained end-unit townhome in the sought-after Bayview Hills community of Chesapeake Beach! This spacious three-bedroom, three full bathroom home is one of the larger models in the neighborhood and offers the perfect blend of comfort, style, and convenience. Step inside to find a bright and inviting main level featuring gleaming hardwood floors and a clean, well-kept

Dawn Riley RE/MAX One

Genna Fleming Hyatt & Company Real Estate LLC