Chester Homes with Circular Driveway Parking features

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Chester and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Chester Homes with Circular Driveway Parking features

$1,350,000

4 Beds ⋅ 3 Baths ⋅ MDQA2018902 MLS

Coastal elegance meets effortless waterfront living on the sunrise side of Prospect Bay. From the moment you arrive, this exceptional home feels special. Ideally positioned on a picturesque jut of land, the setting offers a bit of additional protection while showcasing beautiful, ever-changing water views and spectacular sunrises. A circular driveway leads to a charming courtyard entrance framed by lush perennial gardens. Inside, the views immediately take center stage. An open, coastal elegant floor plan bring the beauty of Prospect Bay into every living space. Coffered ceilings elevate the spacious family and dining rooms, while substantial crown molding and elegant finishes add timeless character throughout. The expansive kitchen is as beautiful as it is functional, featuring a 9-foot island with seating, stainless steel appliances, wine cooler, accent lighting, soft-close cabinetry and drawers, and a pantry. And the views? Simply fabulous. Large sliders open to the heated and cooled sunroom, where walls of windows create a spectacular connection to the water. Designed for both entertaining and relaxing, this may quickly become your favorite room in the house. The custom bar is an exceptional conversation piece, crafted with mahogany and other wood from a 1963 Chris-Craft. The primary suite offers a private retreat with water views and direct access to the waterside patio. A generous, customized walk-in closet leads to the beautifully appointed primary bath, featuring double sinks, a private water closet, and an extraordinary L-shaped tiled walk-in shower with showerheads on two walls. Two bedrooms are thoughtfully positioned on the opposite wing of the home with 1 additional bed and full bath on primary wing. Outside, waterfront living truly comes alive. Enjoy morning coffee and evening gatherings on the Trex deck, or head down to the private pier where two boat lifts await, including an impressive 12,000-pound lift. A spacious shed provides convenient additional storage. And the community setting adds even more to the lifestyle, with a boat ramp, waterfront children's playground, picnic area, and kayak launch—all offering easy ways to get outside and enjoy. This home is designed for waterfront living.

1509 Calvert Rd, Chester

$2,625,000

3 Beds ⋅ 2 Baths ⋅ MDQA2017820 MLS

Privacy without isolation! - Rare Find - 2 comfy homes on one waterfront property, each served by public sewer.! Both with unobstructed views of the picturesque Cox Creek before it enters the Bay. Discover a captivating traditional charm in this vintage cape cod recently updated in spring 2026 ( 3-bedrooms, 2-bathrooms, with enclosed and screened porches.) The former detached garage converted into a 2 story guest cottage (2BR, 1.5 BA) has a fabulous screened porch you'll spend endless hours on. A separate building provides versatile storage for equipment or hobbies. Nestled in a serene rural setting, this home boasts picturesque views along the banks of Cox Creek, offering panoramic western vistas that will take your breath away, especially as the sun sets on the horizon. Step inside to find a thoughtfully designed interior featuring rich wood floors in most rooms. Upgraded countertops and new appliances elevate the kitchen, convenient to the screened porch perfect for gatherings. The living room, complete with a brick fireplace, invites warmth and relaxation. Enjoy the convenience of an entry-level bedroom, or home office, in this traditional floor plan that flows seamlessly throughout. The exterior amenities are equally impressive, featuring a private shoreline and a circular gravel driveway that accommodates ample parking. With 548 feet of waterfrontage, indulge in fishing, boating, or simply soaking in the tranquil surroundings. The property includes a private dock with electric hoist and ramp, making water access effortless. . The secluded parcel offers year-round access, ensuring your retreat is always within reach. This home is not just a residence; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this serene haven your own! Less than 30 minutes to Annapolis, 50 minutes to Baltimore or DC.. Convenient to area restaurants and points of interest. Not under subdivision restrictions. Perfect for multi-generational living, private guest quarters, or possible rental income. Room for expansion of living spaces, outdoor sports court, horseshoes, bocci, or gardens.. Former waterside pool could be revitalized, subject to county approval.

300 Woods Point Rd, Chester

Start Your Search

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.