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Chester Homes with Virtual Tours

Scroll down to browse homes in Chester, MD featuring virtual tours. Select the "Virtual Tour" button below a listing to view the tour. Please note that some of these listings may have virtual tours coming soon.  

Chester Maryland Homes for Sale with Virtual Tours

Contact Chuck Mangold if you have any questions or if you are interested in a specific property. 

View all Chester MD real estate listings here.

2012 Chester Rd Chester MD 21619

Chester, MD2012 Chester Rd

Price$3,400,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDQA145218

  • Land
  • Acreage 105

Gorgeous water views, stunning wetlands and farmland! Easy commute to Washington DC, Baltimore, MD, Philadelphia PA. and other major cities on the East Coast! This parcel of land, situated on Marylands Eastern Bay, is 105 pristine acres located on Kent Island. Comprised of 10 separate lots, we are selling as "one" parcel allowing buyer to execute and create their vision on one of the few remaining and available parcels of land of this size! Perfect for building your dream home, family compound or developing into a new subdivision, there are multiple opportunities to consider! Perc studies have been completed, and SDA plan submitted to Queen Annes County May 2020. Plan is included in documents in listing. Multiple meetings with county planning and zoning and health department with preliminary discussions indicating potential for re - subdividing existing lots.

Listed by Joseph A Petrone of Monument Sotheby's International 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.

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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.

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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

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$
%
$/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.

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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

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$
%
$/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.

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141 Switchgrass Way #44 Chester MD 21619
Pending

MLS Number MDQA2000258

  • Condo
  • Bathroom 3
  • Year Built 2022
  • Bedrooms 3
  • Square Feet 2602

The stunning 4th floor Severn home design is loaded with designer options and includes 3 bedrooms, 2.5 baths, a home office, dry bar cabinetry package, fireplace and two entrances to the private balcony. The building has elevator access, key pad entry, 1 car garage and secure storage room per unit . Available for delivery winter 2022 and just a short walk or drive to the incredible 24,000 square foot owner's clubhouse opening summer 2022! Welcome to a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled, resort-style experience less than 25 miles from Annapolis and within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse, indoor and outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site, Four Seasons at Kent Island also features a well-maintained calendar of activities and classes from yoga sessions, to paddle boarding or walking club. 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. 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.

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

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

141 Switchgrass Way #21 Chester MD 21619
Pending

MLS Number MDQA2000244

  • Condo
  • Square Feet 2602
  • Year Built 2020
  • Bathroom 3
  • Bedrooms 3

The bright and elegant Severn home design includes over 2,600 square feet with 2 bedrooms, a spacious home office, 2.5 baths and a one car garage. Additional designer features added to this home are a cozy fireplace in the living area, a dry bar in the dining area, and access to the balcony from the owner's suite. Call today to find out the details and start living the life you want. Welcome to a new 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 can take advantage of the community's 24,000 sq. ft. clubhouse, a pool with tiki huts, 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 Zumba classes, yoga sessions, billiards 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. The building has elevator access, 1 car garage per unit, personal balcony facing open space and secure storage rooms. This floor plan features 3 bedrooms, 2.5 baths, home office with french doors and a balcony. Home includes a Gourmet Kitchen with stainless steel appliance package with gas cooking, quartz counterops in kitchen and owner's bath, luxury vinyl plank flooring in common areas and many other designer upgrades. Call today for your private tour.

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

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

4000 Heron's Nest Way #34 Chester MD 21619
Pending

MLS Number MDQA148066

  • Condo
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2602
  • Year Built 2021

This Severn home design features 3 bedrooms and 2.5 baths and over 2600 sq. ft. of open living space and is available to move in fall 2021! The building has elevator access and key pad entry, 1 car garage and secure storage per unit, personal balcony facing open space. 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.

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

4000 Heron's Nest Way #31 Chester MD 21619
Pending

MLS Number MDQA147348

  • Condo
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2602
  • Year Built 2021

*Home is available to move in Fall 2021. 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. The building has elevator access, 1 car garage per unit, personal balcony facing open space and secure storage rooms. This floor plan features 3 bedrooms and 2.5 baths and over 2600 sq. ft. of open living space.

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

4000 Heron's Nest Way #21 Chester MD 21619

MLS Number MDQA147266

  • Condo
  • Bathroom 3
  • Bedrooms 3
  • Year Built 2021
  • Square Feet 2602

*This quick move in home is available to move in Fall 2021. The Severn home design offers 3 bedrooms and 2.5 baths and over 2600 sq. ft. of open living space with a personal balcony. The building has elevator access, 1 car garage per unit, and a secure storage room. 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 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

1 Bayberry Dr Chester MD 21619

Chester, MD1 Bayberry Dr

Price$577,990

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.

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.

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