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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.

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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
  • Subdivision Harbor View
  • Address 1757 Harbor Dr
  • Bathroom 3
  • Bedrooms 4

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: 5.25% last updated on May 19, 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 Carriage Heath Chester MD 21619

Chester, MD154 Carriage Heath

Price$939,900

Est. Mortgage: $/month

Active With Contract

MLS Number MDQA2003222

  • Single Family
  • Subdivision Gibsons Grant
  • Address 154 Carriage Heath
  • Bathroom 3
  • Year Built 2015

This special Gibsons Grant Coastal Contemporary backs up to the Community Open Space and Waterfront. Perfect! Awesome double sand bar creates a calm pooling of water to get your toes wet while also creating a sandy beach area. Relax and watch nature change day to day! Now come enjoy the scenic water views from inside this custom home. Love this floor plan! Spacious gourmet kitchen and family room are open and connected by the over-sized island with seating. Both are filled with light and the family room is further enhanced with a gorgeous stack stone gas fireplace. There is a separate dining room and a good sized main level office plus 2 covered waterside porches. Fabulous! Lovely hardwood floors and moldings run through out most of the main level. Excellent fit and finish with attention to detail. Perfect waterside owners suite offers a large walk in closet, a sitting/dressing room with more closet space and provides private access to the 2nd floor waterside porch. Additionally, the owners bath has a walk in shower, soaking tub and double sinks. A separate staircase leads to the private 4th bedroom. It is a spacious room and a great space for an au paire or guest suite or teenagers get away/moms get away/dads get away, theater room, etc. This versatile room has its own heat and air and access to lower level full bath. 2 car attached garage and fenced court yard complete this special property. Gibsons Grant has fabulous community amenities including: heated pool, clubhouse with party room, fitness center, multiple pavilions, fishing pier and kayak launch. Convenient to Bay Bridge for easy commute and just minutes from waterfront dining, golf courses, marinas, shopping and all the shore has to offer.

Listed by Jimmy J White Jr. and Mary E Casson of Long & Foster Real Estate,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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2613 Cecil Dr Chester MD 21619

Chester, MD2613 Cecil Dr

Price$930,000

Est. Mortgage: $/month

Open House

MLS Number MDQA2003380

  • Single Family
  • Next Open House: Sat 05/21 1:00 pm. to 3:00 pm.
  • Address 2613 Cecil Dr
  • Subdivision Harbor View
  • Bathroom 3

Just in time for summer to enjoy your fresh catch off your private pier! You will love the convenience, location, and waterfront lifestyle of this beautiful Chester home. Located along Cox Creek, this light-filled custom-built home features hardwood floors, an open main level floorplan, updated kitchen, attached 1.5 car garage, main level laundry, gas fireplace, and five bedrooms on the second level. The primary bedroom is complete with cathedral ceilings, an extra-large walk-in closet and Cox Creek views! The primary bathroom includes double vanities, soaking tub and separate shower. The large fifth bedroom with storage closet could be used as additional family room/rec space or home office. Enjoy entertaining on the large waterside deck or take in the peaceful views of Cox Creek while relaxing in the hot tub. The private, well maintained L-shaped pier includes an 8,000lb boat lift, floating kayak dock, and jet ski lift. St. Michaels and Annapolis are just a short boat ride away. Harbor View is conveniently located to Route 50 and the Bay Bridge, nearby shopping, dining, entertainment, parks and trails, Annapolis (17 miles), BWI Airport (35 miles), and Baltimore (39 miles). Easton/Oxford and St. Michaels are just 30/40 minutes away! This home is the complete waterfront package with something for everyone! Interior photos coming soon!

Listed by Caitlin E Prossner of Coldwell Banker Realty

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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Lot 31f Parks Rd Chester MD 21619

Chester, MDLot 31f Parks Rd

Price$885,000

Est. Mortgage: $/month

MLS Number MDQA2002630

  • Single Family
  • LocationType River
  • Subdivision Bentons Pleasure
  • Address Lot 31f Parks Rd
  • Square Feet 2775

The Seahawk is a stunning waterfront home designed to take advantage of the waterfront views. Take care of two dreams at once with building a new home and living on the waterfront. You also can build a pier with permit a 108 feet of waterfront. This home has a open floor plan on the main level and the floor plan, really cant get much better then this one for waterfront. Great location central to shopping, church, bay bridge and at the same time feel like you got away from it all! (See current builders plans for price out and up grades, Lot to be purchased separately see Bright for listing) Upgrades are available throughout the home including a gourmet kitchen, sunroom, a flexible room that could be a home office, first floor master, or in-law suite, and decks on every level. The plan starts at 2,755 sq. ft. with options to expand up to 4,425 sq. ft. up to 5 bedroom and 5 baths possible. The Seahawk allows you to choose from multiple second floor layouts to personalize the home for your family. An optional 3rd floor loft and deck provides even more space for entertaining or just enjoying a quiet sunset or nature on the river.

Listed by Dee Dee R McCracken of Coldwell Banker Realty

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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1618 Postal Rd Chester MD 21619

Chester, MD1618 Postal Rd

Price$739,900

Est. Mortgage: $/month

MLS Number MDQA2003476

  • Single Family
  • Address 1618 Postal Rd
  • Subdivision -0-
  • Bathroom 4
  • Bedrooms 6

IN-LAW SUITE/COMMERCIAL!!! 4,227 sq feet Residential/Commercial Mixed Use Town Center. Public Sewer. A must see!! The main house has 5 bedrooms and 2.5 full bathrooms and 1 bedroom 1 bath full kitchen separate. Front rental is separately metered, currently rented residentially, is zoned for commercial use (TC Zoning). Great opportunity for a business or for someone looking for an in-law suite. From granite and stainless steel appliances in kitchen to upgraded bathrooms this open floor plan provides multiple living areas. Master bedroom has its own private full bath with soaking tub and separate shower. The third level has its own bedroom and living room!! Two car side load garage and extremely private deck. Vinyl fully fenced side yard and large front porch!! Don't miss this opportunity to purchase a property where you can offset your mortgage with a tenant or have your small business.

Listed by James B Davidson of Coldwell Banker Waterman Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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193 Spinnaker Way Chester MD 21619

Chester, MD193 Spinnaker Way

Price$724,900

Est. Mortgage: $/month

Pending

MLS Number MDQA2002608

  • Single Family
  • Address 193 Spinnaker Way
  • Bathroom 3
  • Bedrooms 4
  • 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: 5.25% last updated on May 19, 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

190 Sailcloth Way Chester MD 21619

Chester, MD190 Sailcloth Way

Price$699,900

Est. Mortgage: $/month

Pending

MLS Number MDQA2000061

  • Single Family
  • Address 190 Sailcloth Way
  • Bathroom 3
  • Bedrooms 4
  • 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: 5.25% last updated on May 19, 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

112 Saltworks Dr Chester MD 21619

Chester, MD112 Saltworks Dr

Price$699,900

Est. Mortgage: $/month

MLS Number MDQA2002920

  • Single Family
  • Address 112 Saltworks Dr
  • Square Feet 2438
  • Year Built 2021
  • Bathroom 3

IMMEDIATE MOVE-IN HOME - No waiting on new construction to move into this popular community. Please schedule a walk-through to learn more. Two bedrooms, two baths and half, plus an office/rec room or bedroom usage if needed, 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. Enjoy this gourmet kitchen with gas cooking, a tile backsplash and granite countertop, and a spa walk-in shower. It's located in the well sought-after active adult 55+ community and within walking distance 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, a ballroom, and 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: 5.25% last updated on May 19, 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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1620 Postal Rd Chester MD 21619

Chester, MD1620 Postal Rd

Price$689,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDQA2003198

  • Single Family
  • Address 1620 Postal Rd
  • Subdivision Chester
  • Bathroom 3
  • Bedrooms 5

HURRY to This OVER 2800 SQFT 3 Level BEAUTY!! She will not disappoint! Full of Updates and Upgrades to include Spacious Deck overlooking the Fenced in Backyard which surrounds the Inground Heated Saltwater Pool! Move right in and enjoy the POOL NOW!! Lots of FUN Memories to be had here! Boasting 5 Large Bedrooms (inclusive of MASSIVE BONUS ROOM), 2.5 Baths and walk in closets! WIDE OPEN EAT-IN KITCHEN has Cafe' Classic Dual Convection & Gas Oven for the Gourmet Chef at heart! Upgraded Kitchen has WINE Frig, Bosch Dishwasher, custom Tile backsplash, Granite countertops, Bar area, Desk area and a Sprawling Island overlooking the Family Room complete with Gas Fireplace and stunning Custom Surround Mantel! Extra bonuses are a nice size Formal Dining Room, Separate Laundry Room with folding table and cabinets and an Oversized 2 Car garage with TONS of Storage space! Be graciously Welcomed Home every time with the extensive Covered porch... just bring those Rocking Chairs! Superb location with walking distance to Shopping, Restaurants, Boat Landing, Grocery Store and more! Come see what Eastern Shore living is all about! Bike and Walking Trails, Beaches, Outlets, Marina's, Fishing and Crabbing Piers Playgrounds, Sports Fields, Parks, Seafood Restaurants and so much more! Easy commute to DC, Baltimore, Annapolis and Easton. Short trip to St. Michaels, Delaware Beaches and DE Shopping and Ocean City MD. NO HOA!!

Listed by Pamela B Ackermann of RE/MAX Executive

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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104 Woods Rd Chester MD 21619

Chester, MD104 Woods Rd

Price$629,900

Est. Mortgage: $/month

Pending

MLS Number MDQA2003132

  • Single Family
  • Subdivision Bentons Pleasure
  • Address 104 Woods Rd
  • Year Built 2002
  • Bedrooms 5

Gorgeous 2 story open foyer and family room. Owners suites on first and second floors. Kitchen boasts 42" maple cabinets with center island. New carpet in Living , Dining and Family room. This home shows very well and will not last long in this market.

Listed by Ronald G Sebeck Sr. of Revol Real Estate,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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$606,990

Est. Mortgage: $/month

MLS Number MDQA144038

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

The San Sebastion is currently able to be viewed at the Four Seasons at Kent Island Community. 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: 5.25% last updated on May 19, 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

163 Sailcloth Way Chester MD 21619

Chester, MD163 Sailcloth Way

Price$596,900

Est. Mortgage: $/month

MLS Number MDQA2003114

  • Single Family
  • Address 163 Sailcloth Way
  • Bedrooms 2
  • Year Built 2022
  • Bathroom 3

This Quick Delivery Barbuda home will be move in ready by late summer 2022! 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: 5.25% last updated on May 19, 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 May 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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