Search Homes:

Waterfront Homes in Chester MD

Explore current waterfront homes for sale in Chester MD below. You may also like to view listings for Eastern Shore waterfront homes.

Chester Waterfront Real Estate

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.

316 Serenity Ln Chester MD 21619

Chester, MD316 Serenity Ln

Price$2,225,000

Est. Mortgage: $/month

MLS Number MDQA2001076

  • Single Family
  • Address 316 Serenity Ln
  • Bathroom 6
  • Square Feet 5725
  • Bedrooms 4

Located in the small, private peninsula of fine properties in Serenity Farms, this absolutely gorgeous waterfront home is situated on just under 4 beautiful acres! A wonderful stone paver driveway leads to the home and your 3 car garage. With a 114' foot pier, boat lift, fantastic in-ground pool and expansive patio area including outdoor grill and kitchen, you will love this amazing vacation-like setting! The home boasts 4 large bedrooms including primary bedroom suites on the main level and upper level! There are 4 full bathrooms plus 2 half baths. The main level primary bedroom suite has it all... spaciousness, a lavish bathroom, and a massive walk-in closet and water-view. You will love the sprawling open floor plan of this home which includes a large, bright, fully equipped kitchen with granite counter-tops, oversized island, walk-in pantry, and a spacious dining area, with incredible water views. The grand living room boasts 12 foot high box-framed ceilings, a gas fireplace and lots of natural light! Just off of the kitchen is a large formal dining room which is being used currently as an awesome office. There is a huge additional family room with a fantastic custom bar and a second fireplace. You will enjoy wonderful water views from the entire main level. Upstairs you will find 3 generously sized bedrooms, 2 of which have beautiful water-views and private bathrooms, including the 2nd primary suite! The remaining upper level bedroom has an attached bonus room that serves as a spacious, easily accessible storage area. Please view the photos and video of this incredible home and book your appointment!

Listed by Mark J Andrews and Antoinette McDowell of Keller Williams Select Realtors

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

1757 Harbor Dr Chester MD 21619

Chester, MD1757 Harbor Dr

Price$989,000

Est. Mortgage: $/month

MLS Number MDQA2000488

  • Single Family
  • Address 1757 Harbor Dr
  • Bathroom 3
  • Bedrooms 4
  • Year Built 2021

Protected waterfront on Cox Creek. Blue Heron II to be built. Personalize this home to your taste. 3 story with waterfront decks, luxury finishes, and more. Join us to enjoy the Eastern Shore lifestyle just 10 minutes to the Bay Bridge.

Listed by George M Bailey of Keller Williams Flagship of Maryland

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

2904 Cox Neck Rd E Chester MD 21619

Chester, MD2904 Cox Neck Rd E

Price$925,000

Est. Mortgage: $/month

MLS Number MDQA2001034

  • Single Family
  • Address 2904 Cox Neck Rd E
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4613

Beautiful four/five bedroom home in Southwind community with Bay views from almost every room. The home offers stacked crown molding and high celings, new carpet and maple flooring. The kitchen has stainless appliances, a large pantry and lots of space for entertainment. The family room is off the kitchen with a propane fireplace and opens to a large deck with beautiful scenic views. The master suite has a large private deck, vaulted ceilings, a custom- designed bathroom with two large closets and lots of space. The home also has a spacious guest suite and two more bedrooms with a Jack-and-Jill bathroom. A large office separated from the living space with cathedral ceiling and office built-ins is the ideal place to work from home. The basement is finished with new flooring and a bathroom and could be used as an additional bedroom suite, game room, media room, playroom or gym. Endless possibilities. The three car super-sized garage offers lots of storage with built-ins and eleven foot ceilings. Ultra efficient Geothermal HVAC system will save you in heating and cooling costs plus there is new LED lighting throughout the home. This private waterfront community on Kent Island offers a clubhouse, boat ramp, tennis, basketball, nature trail and a private boat storage area. All this just minutes to Route 50 and the Chesapeake Bay Bridge. Vacation where you Live!

Listed by Biana J Arentz of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

2851 Cox Neck Rd Chester MD 21619

Chester, MD2851 Cox Neck Rd

Price$824,900

Est. Mortgage: $/month

Pending

MLS Number MDQA147374

  • Single Family
  • Address 2851 Cox Neck Rd
  • Square Feet 3336
  • Bathroom 3
  • Year Built 1991

This amazing 3.07-acre property is the second largest lot in Southwind with stunning water views to the East and West. The large and private front porch entrance brings you inside this home to the foyer where your eyes are drawn to the stunning views of the eastern bay! Connected to the front porch is another porch that is screened-in for relaxing and catching both stunning sunrises and colorful sunsets! Sitting at the dining room table you have both east and west views of the water! The massive kitchen with eat-in table space is perfect for entertaining. This home features soaring 22' beamed ceilings with a massive palladium window in the family room looking out to the Eastern Bay! Nothing better than the Zen life-style of amazing water views. Nestled among beautiful crape myrtle trees on a massive lot, you have privacy, ambiance, and room to expand. This home is a perfect match for a discerning buyer who is looking to put their touch on this amazing property and bring it too to a Million Plus home.

Listed by Catherine W Chapman of Signature Home Sales,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

112 Saltworks Dr Chester MD 21619

Chester, MD112 Saltworks Dr

Price$725,900

Est. Mortgage: $/month

MLS Number MDQA2000962

  • Single Family
  • Address 112 Saltworks Dr
  • Year Built 2021
  • Bathroom 3
  • Bedrooms 2

You can be in your lovely single-family home by Thanksgiving and or Christmas 2021! Two bedrooms, two baths and half, plus an office, two-car garage, masonry/stone fenced backyard with stainless steel built-in grill. This open floor plan formal dining room, kitchen with eat-in kitchen area and family room allow for fun entertaining with a large island and plenty of counter space. This space opens to a sitting area on the screened-in patio to the masonry/stone-fenced backyard... great for entertaining. It's located in the well sought after active adult 55+ community and walking distances to the popular Maryland Chesapeake Bay. You will be within 45 miles of Washington DC and Baltimore. The charming atmosphere of the Four Seasons at Kent Island is perfect for tranquil evening walks, a casual bike ride, local shopping, and Maryland's best seafood restaurants. This resort home is family and pet-friendly and full of fun amenities. You will soon be able to take advantage of the community's 24,000 sq. ft. clubhouse with, indoor and outdoor pools, billiards, ballroom, a state-of-the-art fitness center. The community lifestyle is designed into a well-maintained calendar of activities such as outdoor yoga sessions, pickleball lessons, kayaking, paddleboard, mahjong tournaments, virtual book club, and other activities. 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. Schedule an appointment tour today!

Listed by Frances Middleton of Douglas Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

122 Evelyne St Chester MD 21619

Chester, MD122 Evelyne St

Price$699,000

Est. Mortgage: $/month

MLS Number MDQA2000968

  • Single Family
  • LocationType River
  • Address 122 Evelyne St
  • Bedrooms 4
  • Year Built 2013

This Beautiful Koch built home--Chatham model--is located in Gibson's Grant--a waterfront community nestled along the Chester River that features awesome community amentites including a pool, fitness center, community pier (no docking) and more! Covered front porch and upper level covered balcony are perfect little retreats to sip your morning coffee or star gaze with a glass of wine. When you enter you are greeted with a large foyer and an open comfortable floor plan that includes a main level office, dining area that flows into a spacious kitchen. With endless granite countertops, center island with cooktop, breakfast bar with seating, and stainless steel appliances , cooking won't seem like a chore! Rounding out the main level is a large, sunny family room anchored with a gas fireplace, another small dining area, bath and dedicated laundry. Access the rear-entry two car garage from the laundry room OR venture up the steps to another great living space in the finished room over the garage! The upper level features 3 nicely sized bedrooms and a full bath PLUS the master suite with walk-in closet and private bath. The covered balcony is access from the master suite and 1 of the other bedrooms and looks out onto the grassy courtyard--a great bonus play area! Parking in the ally is easy thanks to 2 additional parking pads (4 in total) plus garage parking. This swesome house in an awesome community is sure to check all your boxes!

Listed by Tricia Z Wilson of Chaney Homes,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

313 Thomas White Blvd Chester MD 21619

Chester, MD313 Thomas White Blvd

Price$689,000

Est. Mortgage: $/month

MLS Number MDQA2001032

  • Single Family
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3291
  • Year Built 2013

Spacious family home located in a quiet section of the waterfront community of Gibson's Grant. Welcoming front porch overlooking the grassy common area, beautiful hardwoods, triple crown moldings. First-floor office and another bonus room provide plenty of space for today's working/learning from home lifestyle. The kitchen features mahogany cabinets, granite, and high-end appliances with an eat-in area and flexible space for a sitting room off the kitchen. Fenced back yard, two-car garage with alley parking, and conditioned crawl space for extra storage. Neutral colors throughout make this ready for the new owners to make it their own! As a bonus, this home is also pre-wired for surround sound. This property offers the best of living in this community--a quiet location, a grassy area in front for added privacy, and close to neighborhood amenities make it an ideal retreat. Gibson's Grant is a wonderful waterfront community packed with amenities to enjoy! Water access and activities including a kayak launch, fishing, and a pier as well as a swimming pool and playground. Active living features such as walking paths and a fitness center, and community center with Pavilion, picnic area, and refurbished barn. It's easy to see why this community is sold out. Convenient location just off of Rt. 50 with proximity to Bay Bridge.

Listed by Deborah Mangold Lipscomb of Benson & Mangold,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

623 Dominion Rd Chester MD 21619

Chester, MD623 Dominion Rd

Price$675,360

Est. Mortgage: $/month

MLS Number MDQA2000590

  • Single Family
  • Address 623 Dominion Rd
  • Square Feet 2446
  • Bathroom 3
  • Bedrooms 4

TO BE BUILT. Build your dream home in the water-oriented community of Kings Ransom! The Hallmark model boasts gourmet kitchen with Granite counters & stainless steel appliances, primary bedroom with full bath, large family room and 2-car garage! Other models available as well! Or bring your own builder. The spacious lot offers views of the Kirwans Creek as well as a place to dock your boat of you choose to add a slip is located in close proximity of the community marina, beaches, playgrounds and boat launches! Kings Ransom is conveniently located to restaurants, shopping, and the Bay Bridge. You will love it! Listed price is inclusive of lot, estimated lot finishes/site work/permits, and the base price plus options for the house.

Listed by Angela T Lucas and Tiffany Lucas of Samson Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

120 Claiborne St Chester MD 21619

Chester, MD120 Claiborne St

Price$669,900

Est. Mortgage: $/month

Active With Contract

MLS Number MDQA2000526

  • Single Family
  • Address 120 Claiborne St
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2412

Enjoy Coastal Living in the Waterfront Community of Gibsons Grant. This Gorgeous 3 Bedroom, 2.5 Bathroom Open Concept Home Features Custom Wrap Around Porch ( Few in Community!) Newly Built Four Season Room w. Shiplap Ceiling (2020), Deck w. Custom Pergola (2020) & Large Stone Patio. This Professionally Landscaped Backyard will Impress Your Toughest Critic! Coretec Plank Flooring on Main level & Hardwood Throughout. Home Exterior Freshly Painted (2019) Plantation Shutters Throughout. Shiplap Accent Wall in Family Room. Open Kitchen w. Stainless Steal Appliances, New Dishwasher (2020), Granite Counter Tops. All Bedrooms & Laundry on Upper Level. Easy Access to Crawl Space w. Ample Storage Space! Take Advantage of the Resort Style Community Amenities; Pool, Gym, Fishing Pier, Covered Pavilion w. Fire Pit & Children's Playground.

Listed by Kelly Elizabeth Glen of KW Metro Center

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

147 Carriage Heath Chester MD 21619

Chester, MD147 Carriage Heath

Price$640,000

Est. Mortgage: $/month

MLS Number MDQA147880

  • Single Family
  • Address 147 Carriage Heath
  • Square Feet 2148
  • Bedrooms 3
  • Year Built 2015

Beautiful 2 story home in Gibson's Grant! Located in a private Cul-de-sac with water views! Built in 2015 this home Shows like New! This 2,148 square foot home is the perfect size and features an Open floor plan with Gourmet Kitchen and Upgraded options that include Stainless steel appliances, Gas stove, Hardwood floors, 9 foot high ceilings, Crown molding, Paneled wainscot, Gas Fireplace, Recessed Lighting, Ceiling Fans, Composite decking, Vinyl railings and Fire suppression ( sprinkler ) system! Need to work from home? The main level office with French doors and bright sunny windows is perfect! When you're done working, Walk out to the side porch for grilling and relax on the Brick patio below. Three bedrooms upstairs include a large Master suite with Walk in closet and En Suite bath. Large private second story deck off the Master suite overlooks the treetops and sunset behind the home. Enjoy the water views from the two front bedrooms windows and the office below. Under the home there is a Conditioned Crawl space, high enough for storage that is a great bonus and easily accessible from inside stairs! Outside the detached two car garage features even more room for storage of your bikes, kayaks or other items! Enjoy the community amenities this summer, Outdoor pool, Community pier, kayak launch and walking trails. Rare opportunity to be in this private corner of Gibson's grant! Easy access to route 50 and mere minutes to the Bay Bridge! Call today for your showing!

Listed by Cornelia Fallon of Coldwell Banker Waterman Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

1704 Bayside Dr Chester MD 21619

Chester, MD1704 Bayside Dr

Price$639,900

Est. Mortgage: $/month

Pending

MLS Number MDQA2001024

  • Single Family
  • Address 1704 Bayside Dr
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1592

This stately and refined home in Chester, Maryland is an absolute treasure that features 3 beds and 2.5 baths across 1,592 total finished sq ft. The water view is unsurpassed, looking to the south stretching to the horizon. This home has magnificent views and spectacular sunsets, truly one of the best in town! This home includes a new pier (2020)! Inside is a bright and open living space featuring the living and dining room. The living room has pristine brick walls and a fireplace framed with built-in shelves. Off the dining area is a large eat-in kitchen complete with stainless steel appliances, a range hood, brick backsplash, and tons of solid wood cabinets. You'll also find a fireplace with a brick wall and glass sliding doors to the sunroom. Off the kitchen is a convenient half bath and a spacious and well-organized laundry space making chores a breeze! Move your way to the bedroom area of this home featuring 3 beds including the primary suite with a walk-in shower with grab bars and a built-in seat. The 2 other bedrooms are substantial and each has a ceiling fan. They share a full hallway bath that has a tub/shower combo! Both bathrooms were redone in the last 8 years. There's a lovely sunroom with a storm door to the backyard. This part of the home is cozy and offers a great view of the surrounding territorial area. The crawlspace has been completely encapsulated with a commercial-grade dehumidifier & sump pump as well! Parking is made easy with your 2 car garage with a wide driveway for additional parking. The massive yard is perfect to host large gatherings and is a great spot to watch the sunset. 1704 Bayside Drive brings you close to Kent Narrows and plenty of dining and shopping destinations! Book your appointment soon!

Listed by Brian K Cooper of Houwzer,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

138 Sailcloth Way Chester MD 21619

Chester, MD138 Sailcloth Way

Price$599,900

Est. Mortgage: $/month

Pending

MLS Number MDQA2000996

  • Single Family
  • Address 138 Sailcloth Way
  • Bedrooms 2
  • Bathroom 2
  • Year Built 2021

Beautiful QUICK MOVE IN HOME! Available October 2021. *Photos are of a model home and not the actual property.* Please schedule a walk through to learn 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: 2.88% last updated on Sep 23, 2021
* 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

Copyright 2021 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 September 27, 2021. 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