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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

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1721 Harbor Dr Chester MD 21619

Chester, MD1721 Harbor Dr

Price$995,000

Est. Mortgage: $/month

Pending

MLS Number MDQA2001512

  • Single Family
  • LocationType Creek/Stream
  • Address 1721 Harbor Dr
  • Bedrooms 3
  • Bathroom 3

Gorgeous Cox Creek Waterfront Home - Meticulously Maintained! Dreaming of life on the water? This beauty will win you over from the minute you step in the front door. Nearly 2800 SF of living space, soaring cathedral ceilings, first floor primary suite and main level office--it's exactly what you've been waiting for! Upper level features frontside and waterfront balconies, 2 nice sized bedrooms with adjoining jack-n-jill bath PLUS additional living space that overlooks the main level family room and kitchen. Generous in size without being too much, it's the perfect balance. Hop on the boat and head out to big water for an afternoon of fishing or a boat ride to St Michaels (just 20 minutes away!). Facing Sout/SouthWest means warm sunshine will pour in most of the day. Buyers Get Ready! This One Will NOT Last!

Listed by Tricia Z Wilson of Chaney Homes,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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.

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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
  • Year Built 2021
  • Bedrooms 4
  • Bathroom 3

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: 3.45% last updated on Jan 13, 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.

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154 Bluebell Ct Chester MD 21619

Chester, MD154 Bluebell Ct

Price$830,000

Est. Mortgage: $/month

MLS Number MDQA2001458

  • Single Family
  • Address 154 Bluebell Ct
  • Year Built 2020
  • Bathroom 3
  • Bedrooms 3

HUGE VALUE ALERT - This Home is Priced $35+ per square foot BELOW New Construction saving you Tens of Thousands of Dollars!!! This is NOT A MODEL. This home is available NOW. No need to wait 9-12 months for New Construction! Welcome to 154 BlueBell Ct in the premier 55 and better community, Four Seasons on Kent Island. You will fall in love from the moment you step inside this 3400+ sq ft home that has all the best upgrades (some no longer available from the builder) plus updates that will make you swoon. The 10' ceilings, 8' door, luxury vinyl plank flooring spans the main floor creating a continuous flow throughout the bedrooms and living areas. With 3 Bedrooms, 3 Full baths plus an office there is plenty of space for privacy and entertaining. Speaking of entertaining, the gourmet kitchen with quartz countertops, 14' island, double oven, upgraded cabinets will be the heart of your new home. Step out into your screened in porch from the morning room bump out to watch the sunrise over the beautifully landscaped common areas. Your hardscaped patio creates an inviting area for dining or relaxing around the built in propane fire pit. The primary bedroom with en suite is truly 5 star resort quality from the 14' Spa Walk-In Shower to the expansive walk-in closet with custom built-ins. The loft area could be a private retreat for guests, perfect for an office or rec room. The sky basement is just one of the many storage options you will find in your new home. The two car garage has been finished, including epoxy flooring making it perfect for the car enthusiast or tinkerer. Four Seasons on Kent Island is a Resort Style amenity rich active living community. The impressive clubhouse is scheduled to open Spring 2022 and includes indoor and outdoor pools, fitness center, library, bocce ball courts, pickle ball, kayak launch, dog park, walking paths and more! Visit the community website for more information and pictures) All just minutes to waterfront dining, shopping, marinas, golf courses, and the Chesapeake Bay Bridge. Start the NEW YEAR in your NEW HOME! It's time to make THE SHORE HOME.

Listed by Kathleen M Higginbotham of Keller Williams Flagship of Maryland

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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.

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190 Sailcloth Way Chester MD 21619

Chester, MD190 Sailcloth Way

Price$699,900

Est. Mortgage: $/month

MLS Number MDQA2000061

  • Single Family
  • Address 190 Sailcloth Way
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2862

This quick move in home will be available in Spring 2022. This luxurious home will sit on a premium homesite backing to trees and features many designer upgrades. The centerpiece of the home is a gourmet kitchen with gas cooking, tile backsplash and quartz countertops. The adjoining great room includes a cozy fireplace and the flooring has been upgraded throughout the first floor and all baths. Call today to to visit and learn more. Welcome to the premier active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and luxury condominiums. Discover an amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents 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, and yoga studio, and multiple tennis & pickleball courts. With a full-time lifestyle director already on site, there is always something for you to enjoy along with neighbors, friends and family. 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 socially distanced 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. 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.*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: 3.45% last updated on Jan 13, 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.

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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
  • Bedrooms 4
  • Bathroom 3

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 of Samson Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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.

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140 Spinnaker Way Chester MD 21619

Chester, MD140 Spinnaker Way

Price$587,985

Est. Mortgage: $/month

Pending

MLS Number MDQA2000063

  • Single Family
  • Address 140 Spinnaker Way
  • Bathroom 2
  • Square Feet 1993
  • Bedrooms 2

This quick move in home will be available Spring 2022. This home is filled with upgrades including a gourmet kitchen with white cabinetry, quartz countertops, stainless appliances and gas cooking. Flooring is upgraded throughout the main living areas and bathrooms. Enjoy your outdoor space from the comfort of the screened patio. Call today to learn more! *Photos are of a similar model. 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: 3.45% last updated on Jan 13, 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

1 Bayberry Dr Chester MD 21619

Chester, MD1 Bayberry Dr

Price$583,990

Est. Mortgage: $/month

MLS Number MDQA144038

  • Single Family
  • Address 1 Bayberry Dr
  • Bathroom 2
  • Bedrooms 2
  • Square Feet 2597

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. *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: 3.45% last updated on Jan 13, 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

1351 Calvert Rd Chester MD 21619

Chester, MD1351 Calvert Rd

Price$560,000

Est. Mortgage: $/month

MLS Number MDQA2001316

  • Single Family
  • Address 1351 Calvert Rd
  • Square Feet 2700
  • Year Built 2007
  • Bedrooms 5

This amazing home has everything! From the large front porch with bay views, to the gourmet kitchen with granite countertops. The spacious owners suite has a sitting area, walk-in closets, dual vanities and a shower that has to bee seen to appreciate! Upgrades are everywhere including LED lighting and fresh paint throughout and there are 9 ceiling fans, 2 on the porch!!!!!The luxurious home office features water views as well!! The HUGE garage has tons of storage space and the workshop has a 30amp shore power hookup for your RV or Boat. This great home is ready for immediate move-in.

Listed by David C Williams of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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

127 Hopkins Rd Chester MD 21619

Chester, MD127 Hopkins Rd

Price$524,900

Est. Mortgage: $/month

MLS Number MDQA146656

  • Single Family
  • Address 127 Hopkins Rd
  • Bathroom 3
  • Year Built 2021
  • Bedrooms 4

One of our most popular designs, the Doral offers formal and informal living areas with lots of room for the whole family to spread out. Main level features a formal living and dining room as well as a spacious family room and table space kitchen. Add a light-filled morning room off the rear or expand your space with plan extensions. Choose a two or three-car garage for this plan. Upstairs, two bedroom level plans accommodate 4 nicely sized bedrooms .

Listed by George M Bailey of Keller Williams Flagship of Maryland

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 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

2 Saltworks Dr Chester MD 21619

Chester, MD2 Saltworks Dr

Price$504,990

Est. Mortgage: $/month

MLS Number MDQA144034

  • Single Family
  • Address 2 Saltworks Dr
  • Bedrooms 2
  • Square Feet 1689
  • Year Built 2021

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: 3.45% last updated on Jan 13, 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

1 Saltworks Dr Chester MD 21619

Chester, MD1 Saltworks Dr

Price$502,990

Est. Mortgage: $/month

MLS Number MDQA144036

  • Single Family
  • Address 1 Saltworks Dr
  • Bedrooms 2
  • Square Feet 1993
  • Year Built 2021

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. *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: 3.45% last updated on Jan 13, 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

1 Sailcloth Way Chester MD 21619

Chester, MD1 Sailcloth Way

Price$471,990

Est. Mortgage: $/month

MLS Number MDQA147706

  • Single Family
  • Address 1 Sailcloth Way
  • Year Built 2021
  • Bathroom 2
  • Bedrooms 2

Welcome to the premier active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and luxury condominiums. Discover an amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents 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, and yoga studio, and multiple tennis & pickleball courts. With a full-time lifestyle director already on site, there is always something for you to enjoy along with neighbors, friends and family. 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 socially distanced 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. 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. *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: 3.45% last updated on Jan 13, 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

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 January 20, 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.

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