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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

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View all Chester MD real estate listings here.

2909 Cox Neck Rd E Chester MD 21619

Chester, MD2909 Cox Neck Rd E

Price$2,299,500

Est. Mortgage: $/month

MLS Number MDQA2003830

  • Single Family
  • Subdivision Southwind
  • Address 2909 Cox Neck Rd E
  • Bedrooms 3
  • Bathroom 4

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

Listed by Keith Hensley of Meredith Fine Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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$879,000

Est. Mortgage: $/month

MLS Number MDQA2003380

  • Single Family
  • Address 2613 Cecil Dr
  • Subdivision Harbor View
  • Bathroom 3
  • Bedrooms 5

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, freshly painted main level and master bedroom, 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 recently updated primary bathroom includes double vanities, a 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 jet ski dock, and manual kayak 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!

Listed by Caitlin E Prossner of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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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108 Elinor St Chester MD 21619

Chester, MD108 Elinor St

Price$799,000

Est. Mortgage: $/month

Pending

MLS Number MDQA2003844

  • Single Family
  • Address 108 Elinor St
  • Subdivision Gibsons Grant
  • Bathroom 3
  • Bedrooms 4

IRRESISTIBLE COASTAL NEO-COLONIAL in highly sought-after community of GIBSON'S GRANT located on the CHESTER RIVER! Captivating home and sweet quality lifestyle year-round! The welcoming front porch beckons you to enter this adored home featuring 9 ft. ceilings, custom triple crown molding, chair railing, tray ceilings, premium engineered hardwoods, and designer selections throughout. Spacious four Bedrooms, 2.5 Baths. Main level Office/Den, Dining Room, Butler's Pantry with beverage center, rear Great Room combining chef's island dining bar kitchen (double ovens, farm sink, custom tile backsplash, tray ceiling bump-out with pendant lighting, 42” white shaker cabinets), Butler's Pantry with beverage center, and Living Room with cozy gas fireplace. Primary Owners' Suite presents deep tray ceiling, 2 walk-in closets w/organizers, and spa-like Bath displaying a double vanity and separate shower with river stone accented flooring. Upper level Laundry. Basement crawl space finished for extra storage. Entertain in privacy fenced, verdant yard with custom paver patio! Transformer lighting both in front and back of property. Parking pad & breezeway-connected 2-car garage. The community center features pool, fitness center, play & picnic areas, bocce, waterside pavilion and Chester River fishing/crabbing pier! Easy access to RT 50 and minutes to the Bay Bridge. LAUNCH YOUR KAYAK & NEW LIFE ALONG PRISTINE WATERS!

Listed by June M Steinweg of Long & Foster Real Estate,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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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109 John Gibson Dr Chester MD 21619

Chester, MD109 John Gibson Dr

Price$795,000

Est. Mortgage: $/month

Pending

MLS Number MDQA2003788

  • Single Family
  • Address 109 John Gibson Dr
  • Subdivision Gibsons Grant
  • Bathroom 5
  • Bedrooms 6

Listed by Maureen Rehbein of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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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170 Harrier Way #44 Chester MD 21619
Pending

MLS Number MDQA2002562

  • Condo
  • Address 170 Harrier Way #44
  • Year Built 2022
  • Square Feet 2600
  • Bathroom 3

Under construction and move in ready in 2022! The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2.5 baths, dry bar cabinetry package, fireplace and two entrances to the private balcony. The building has elevator access, 1 car garage and secure storage room per unit. 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. *Pictures represent a model home as this current home is under construction.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

1618 Postal Rd Chester MD 21619

Chester, MD1618 Postal Rd

Price$698,900

Est. Mortgage: $/month

MLS Number MDQA2003476

  • Single Family
  • Address 1618 Postal Rd
  • Subdivision -0-
  • Year Built 2003
  • Square Feet 4227

Home is located close to the Bay Bridge, shopping, restaurants and gym along with having an additional rental that generates $1,050/month!! 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 small 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: 5.7% last updated on Jun 30, 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

190 Harrier Way #24 Chester MD 21619
Pending

MLS Number MDQA2003602

  • Condo
  • Address 190 Harrier Way #24
  • Year Built 2022
  • Bedrooms 3
  • Square Feet 2600

Under construction and move in ready in 2022! The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2.5 baths, dry bar cabinetry package, fireplace and two entrances to the private balcony. The building has elevator access, 1 car garage and secure storage room per unit. 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. *Pictures represent a model home as this current home is under construction.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

170 Harrier Way #34 Chester MD 21619
Pending

MLS Number MDQA2002560

  • Condo
  • Address 170 Harrier Way #34
  • Square Feet 2600
  • Year Built 2022
  • Bathroom 3

Under construction and move in ready in 2022! The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2.5 baths, dry bar cabinetry package, fireplace and two entrances to the private balcony. The building has elevator access, 1 car garage and secure storage room per unit. 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. *Pictures represent a model home as this current home is under construction.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

190 Harrier Way #31 Chester MD 21619
Pending

MLS Number MDQA2003604

  • Condo
  • Address 190 Harrier Way #31
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2600

Under construction and move in ready in 2022! The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2.5 baths, dry bar cabinetry package, fireplace and two entrances to the private balcony. The building has elevator access, 1 car garage and secure storage room per unit. 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. *Pictures represent a model home as this current home is under construction.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

170 Harrier Way #31 Chester MD 21619
Pending

MLS Number MDQA2003606

  • Condo
  • Address 170 Harrier Way #31
  • Year Built 2022
  • Bedrooms 3
  • Square Feet 2600

Under construction and move in ready in 2022! The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2.5 baths, dry bar cabinetry package, fireplace and two entrances to the private balcony. The building has elevator access, 1 car garage and secure storage room per unit. 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. *Pictures represent a model home as this current home is under construction.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

190 Harrier Way #21 Chester MD 21619

MLS Number MDQA2003600

  • Condo
  • Address 190 Harrier Way #21
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2600

Under construction and move in ready in 2022! The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2.5 baths, dry bar cabinetry package, fireplace and two entrances to the private balcony. The building has elevator access, 1 car garage and secure storage room per unit. 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. *Pictures represent a model home as this current home is under construction.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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 Bayberry Dr Chester MD 21619

Chester, MD1 Bayberry Dr

Price$611,990

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: 5.7% last updated on Jun 30, 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 July 6, 2022. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

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