Benson & Mangold Real Estate, 31 Goldsborough St, Easton, MD 21601 410.822.6665 | Office

Search Homes:

Chester MD Homes for Sale

Types of single family homes in Cheter MD include many beautiful homes with panoramic water views, waterfront properties with private boat docks, and so much more. Located on Kent Island in Queen Anne's County, Chester gives homeowners a great quality of life and plenty of recreational opportunities to enjoy. View the latest homes for sale in Chester MD below.

Chester MD Real Estate Listings

Call Chuck Mangold at 410-924-8832 with any questions or to schedule a private tour.

Save time! Create a free account to save your favorite listings and get notified when similar properties become available. You can view all homes in Queen Anne's County here.

400 Mulberry Lane Chester MD 21619

Chester, MD400 Mulberry Lane

Price$2,900,000

Est. Mortgage: $/month

MLS Number MDQA2004170

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,036
  • Acreage 17.77

Wake up every morning to the expansive views across the sparkling waters of Cox Creek to the beautiful estates and countryside surrounding this property. Bask in this idyllic rural setting and enjoy the beauty of a peaceful waterfront life but find comfort and convenience in the fact that you are only minutes away from shopping, dining, commuter roads and the Bay Bridge. The best of both worlds! This 17+ acre waterfront property with waterside saltwater pool is nestled between tree-lines on a completely private site along the shoreline of Cox Creek and features 350'+ of waterfrontage, sandy beach and private pier. With 4 bedrooms and 2.5 baths in the main house and an additional bedroom and full bath above the detached 2 car garage there is no shortage of existing living space and the opportunity to expand if needed is practically unlimited. The enormous rear deck which encompasses the entirety of the waterside of the home creates a true indoor/outdoor living experience and gives easy access to the sprawling backyard, refreshing pool and water's edge from all areas of the main level of the home including the Primary bedroom suite. The sunshade sails keep the deck and home cooler in the hot summer months and can be easily removed to let in the sun during the winter. Continually changing throughout the season, the waterviews and views of verdant landscaping delights at every turn and creates endless ways to let the stresses of the day fade away and those views never grow old! It doesn't get much better than the Eastern Shore lifestyle, come experience it for yourself. Welcome Home!

Listed by Bradley R Kappel of TTR Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

2909 Cox Neck Road E Chester MD 21619

Chester, MD2909 Cox Neck Road E

Price$1,899,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDQA2003830

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3,885
  • Acreage 1

DREAM HOME ALERT! Situated perfectly on Crab Alley Bay looking out over Eastern Bay. This meticulously maintained home has it all. A contemporary floor plan, maximizing the water views with floor to ceiling windows. Relax by the pool overlooking the newly renovated dock, equipped for your power boat and jet skis. Call today for your private tour!

Listed by Keith Hensley of Meredith Fine Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

2863 Cox Neck Road Chester MD 21619

Chester, MD2863 Cox Neck Road

Price$1,595,000

Est. Mortgage: $/month

Pending

MLS Number MDQA2004354

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 3,406
  • Acreage 1.5

Professional Picture Coming Soon. Beautiful Coastal two story WATERFRONT with expansive, broad views! 97 custom home community on a stunning peninsula surrounded by water everywhere you look! Estimated water frontage is unknown (120-175 ft). Private pier with lift (not used by owner so AS IS). Fish and crab off your own dock! Breathtaking water views add to the fabulous outdoor living spaces including a sizable screened porch, a large deck, barbecue section and small fish pond. The main level is spectacular with walls of windows to take advantage of the extensive water views, a lovely family room with a fireplace, a generous dining area and a nearly brand new luxurious Kitchen boasting impressive white cabinetry, superb upgrade designer lighting, pendants, countertops and backsplash with an adjacent Morning/Breakfast room featuring a climate-controlled Wine Closet! There is a two-story entry foyer and a Guest BR with full bath on the main level as well. Upstairs you will find the Primary MBR suite and a second Guest BR and bath along with a cozy lofted sitting area or second family room. Don't miss this rare opportunity to see a much-loved waterfront residence in Southwind at one of the very lowest waterfront prices!

Listed by Michele Sinclair of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

1759 Harbor Drive Chester MD 21619

Chester, MD1759 Harbor Drive

Price$1,350,000

Est. Mortgage: $/month

MLS Number MDQA2003194

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 1,743
  • Acreage 0.53

Waterfront on Cox Creek with access to Eastern Bay. Rare opportunity to personalize this home. New home under contract right next door. All the bells and whistles alraedy included in this offering. Great wiews of Cox Creek and beyond. Potential for private pier. Join the Eastern Shore way of life 10 minutes from the Bay Bridge and save a million dollars.

Listed by George M Bailey of Keller Williams Flagship of Maryland

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

207 Bayberry Drive Chester MD 21619

Chester, MD207 Bayberry Drive

Price$959,900

Est. Mortgage: $/month

MLS Number MDQA2004498

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3,347
  • Acreage 0.17

The San Sebastian Model at K. Hovnanian's Four Seasons at Kent Island Community is for sale with a model leaseback. This model comes fully furnished and includes model home details such as a gourmet kitchen, fireplace, screened patio, hard floors. There is a model lease back in place - a rare opportunity to purchase a model home and have the builder lease it back! For more details please contact sales. Welcome to K. Hovnanian's Four Seasons at Kent Island a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse opening summer 2022 with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site, Kent Island also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, Four Seasons at Kent Island also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Listed by Erik M Hoferer of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

203 Mchenny Court Court Chester MD 21619

Chester, MD203 Mchenny Court Court

Price$899,000

Est. Mortgage: $/month

MLS Number MDQA2004346

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 3,552
  • Acreage 0.21

WATERFONT corner lot on cul-de-sac with Main Level and Second Level Primary Suites with Sunset View Balconies. 5 Bedroom 4.5 Bath Koch Builders Home, Including Guest Apartment w Full Bath, Kitchen Area and Separate Entrance. Incredible Water Views from Sunrise on the Chester River to Sunset on Macum Creek. Front and Rear Covered Porches. Gourmet Kitchen w granite, Stainless Steel and Hardwoods. Great Room w Stone Fireplace, Whirlpool Jetted Tub , Plantation Shutters, Programable Thermostat, Conditioned Crawl Space, + More. 1st floor primary can be used as a home office with a waterview or theater room or exercise room. Watch Bald Eagles, Herons , Ospreys and Waterfowl from your private porch or balcony. Direct access to Cross Island Nature Trail, 10 -minute drive to Annapolis, Community Center featuring pool, fitness center, Chester Riverside Pavilion and Fishing Pier. Total square footage includes the guest apartment room of approximately 238 sq feet. 2 VIRTUAL TOURS-CLICK ON THE MOVIE PROJECTOR TO WATCH THE AERIAL VIRTUAL TOUR & A GROUND LEVEL VIRTUAL TOUR

Listed by Lawrence Doyle of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

118 Starlight Court Chester MD 21619

Chester, MD118 Starlight Court

Price$874,900

Est. Mortgage: $/month

Open House

MLS Number MDQA2004812

  • Single Family
  • Next Open House: Sat 10/8 11:00 am. to 2:00 pm.
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3,347

Price Reduction! Additionally, seller is offering $5,000 to closing costs. Move in Ready November 2022! Why wait when you can purchase this brand new home ready for move in this fall? This home includes a morning room with screened patio, oak staircase, ultra spa bath, attic storage in the garage, fireplace, dry bar, gourmet kitchen and much more! Welcome to K. Hovnanian's Four Seasons at Kent Island a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse opening summer 2022 with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site, Kent Island also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, Four Seasons at Kent Island also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Listed by Erik M Hoferer of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

237 Evelyne Street Chester MD 21619

Chester, MD237 Evelyne Street

Price$789,900

Est. Mortgage: $/month

Active With Contract

MLS Number MDQA2004370

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,840
  • Acreage 0.13

Renovated completely in 2018. New Kitchen Quartz counters, Subway Tile Backsplash, Deep Large Sink, New Oven, Luxury Vinyl Flooring, Upgraded Carpet, and New Carpet July 2022 in Primary Bedroom, Bathrooms Upgraded with new Toilets', Vanity's with Marble Tops, Heavy Duty Shower Glass Doors. New Crown molding, Faucets, Light Fixtures, Ceiling Fans, Stamped Concrete Patio, Nest Thermostat and Ring Doorbell Included. Custom Blinds and Plantation Shutters. Custom and Professional Paint throughout. New Washer and Dryer installed 6 months ago. So much more you must come see for yourself. An Extra Room can be used for an Home Office or Storage. Assume 2.25% rate on existing mortgage.

Listed by Lawrence Doyle of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

402 Macum Creek Drive Chester MD 21619

Chester, MD402 Macum Creek Drive

Price$785,000

Est. Mortgage: $/month

MLS Number MDQA2004316

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,787
  • Acreage 0.21

GREAT NEW PRICE & (2) OPEN HOUSES COMING UP; Sat Oct 1 12:30-2:30 & Sunday Oct 2 11-11. Shows like a MODEL in Gibson Grant! Located on a PREMIUM CORNER LOT, one of the largest in the community, this detached home is on the outer circle of the community and faces the reserve and Macum Creek with FABULOUS sunset views from both lower and upper front porches. YOU CAN'T BEAT THIS LOCATION/LOT! Inside you will find the flow and finishes you have been searching for. Hardwood Floors throughout Main Level, a large, open CHEF'S KITCHEN w/ 5-Burner Gas Stove, Stainless Steel Appliances, Granite Counter Tops, Over-Sized Island, Tile Backsplash, Double Wall Ovens, Built-In Microwave, and Pantry. Kitchen Opens to Family Room with a Gas Fireplace framed by Beautiful Stone to the Ceiling and Mounted Flat Screen TV. Access to the backyard oasis from Family Room with large deck, retractable awning, expansive paver patio, firepit, tons of flat, grassy run-around room, all fully fenced. Formal Dining Room off the Family Room is located at the front of the home with an Extra Window for a Light Filled Room. Home Office/Sitting Room/Study across from the Dining Room also at the Front of the Home with two large Windows to bring in the Natural Light. Upstairs, you will find your Expansive Primary Bedroom Suite with Private Porch to view the wildlife on Macum Creek. Primary Bedroom Features a Walk-In Closet, Sitting Area (originally designed for 4th Bedroom could be converted back), Coffered Ceiling and En Suite with Double Sinks, Large Soaking Tub with Jacuzzi Jets, Water Closet and Shower. There are two Additional Bedrooms Upstairs that are both nicely sized and share Hallway Full Bath with Tub/Shower Combo,. The lower level is a conditioned accessible crawl space with inside access for LOTS of extras storage. Tankless Gas Water Heater, Forced Air Gas Furnace. The Community Amenities include a Pool with Clubhouse, Pier for Kayaking, Fishing or Crabbing, Bike Trail, Tot Lot/Playground, Common Area with Covered Pavilion, Firepit, Walking/Jogging Trails, Exercise Room and More... You're going to LOVE IT HERE!!

Listed by Laura E Gayvert of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

221 Bayberry Dr Chester MD 21619

Chester, MD221 Bayberry Dr

Price$779,000

Est. Mortgage: $/month

MLS Number MDQA2004500

  • Single Family
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,689

The Donegal Model Home is currently for sale at K. Hovnanian's Four Seasons at Kent Island Community. This is a rare opportunity to own a FULLY furnished model home with a leaseback in place. This home includes many upgrades including a fireplace, attic storage, custom trim, hard floors. For a full list of included features and the terms of the leaseback please contact sales Welcome to K. Hovnanian's Four Seasons at Kent Island a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can soon take advantage of the community's 24,000 sq. ft. clubhouse, indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site, Kent Island also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, Four Seasons at Kent Island also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town. Call today to find out the details and start living the life you want! *Photos are of similar home as this home is to be built.

Listed by Erik M Hoferer of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

124 Kirwans Landing Lane Chester MD 21619

Chester, MD124 Kirwans Landing Lane

Price$779,000

Est. Mortgage: $/month

Open House

MLS Number MDQA2004710

  • Single Family
  • Next Open House: Sat 10/8 10:00 am. to 12:00 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,604

Opportunity knocks just once ! This WATERFRONT Contemporary home looks straight down Kirwans Creek in a beautiful one acre setting at a NEW IMPROVED PRICE you can't beat. This small community is one of Kent Islands most quaint locations with easy access to Rt 50 by car and minutes to the Kent Narrows attractions by boat or car. Two Bedrooms down, Master on 2nd level with an Office/Loft, open vaulted ceilings, Paved Driveway, Public Sewer and Two Car Side Entry Garage. Exterior decking looking straight down the creek. Incredible views !!!!

Listed by Michael N Rosendale of Rosendale Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

1868 Roberta Drive Chester MD 21619

Chester, MD1868 Roberta Drive

Price$739,900

Est. Mortgage: $/month

MLS Number MDQA2004400

  • Single Family
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,250

Custom built home with many upgrades, and water views. A few upgrades are, 12 ceilings and windows are 6 on first floor. Custom window treatments throughout. Custom hardwoods and tile throughout. Dedicated laundry room with washer and dryer and a laundry sink. Eat in kitchen with granite counter tops and a large center island with pantry. Sunroom off of kitchen. Finished garage. 800 sq. ft. wrap around maintenance free deck. Room to build inground pool. Master bath with custom tile shower and 36 in. double sink vanity. 2 additional "Jack & Jill" bathrooms with double sink vanities. 1820 sq. ft crawl space. 4 ft high finished concrete with indoor access perfect for storage.

Listed by XRealty.NET LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Copyright 2022 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Chuck Mangold participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated October 6, 2022. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

Get In Touch Today

Contact Chuck