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Chester MD Real Estate

The town of Chester is located on Kent Island, the largest island in the Chesapeake Bay. From condos and townhomes to waterfront homes and estates, you’ll find a variety of real estate in Chester. Browse current Queen Anne's County real estate listings in Chester MD below.

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1700 Piney Creek Rd Chester MD 21619

Chester, MD1700 Piney Creek Rd

Price$3,500,000

Est. Mortgage: $/month

Pending

MLS Number MDQA141780

  • Land
  • Acreage 14.51
  • Zoning TC

Combined Undeveloped Parcels Creating 14.506+/- Acres of Land Strategically Located in the heart of Kent Island Maryland,Ideally located between the expanding Annapolis MD market and theRapidly developing markets of Denton MD and Middletown DE;SDAT Parcel Identifiers: 04-003098 and 04-003152

Listed by Marisa A Mullins of The Hogans Agency

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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

Active With Contract

MLS Number MDQA2001076

  • Single Family
  • Address 316 Serenity Ln
  • Year Built 2005
  • Square Feet 5725
  • Bathroom 6

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

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$
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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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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

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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2904 Cox Neck Rd E Chester MD 21619

Chester, MD2904 Cox Neck Rd E

Price$899,000

Est. Mortgage: $/month

MLS Number MDQA2001034

  • Single Family
  • Address 2904 Cox Neck Rd E
  • Year Built 1996
  • Bathroom 5
  • Square Feet 4613

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

Listed by Biana J Arentz of Coldwell Banker Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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154 Bluebell Ct Chester MD 21619

Chester, MD154 Bluebell Ct

Price$875,000

Est. Mortgage: $/month

MLS Number MDQA2000081

  • Single Family
  • Address 154 Bluebell Ct
  • Bathroom 3
  • Square Feet 3434
  • Year Built 2020

Wonderful 3 Bedroom, Flex/Office 3 Full Bath San Sebastian Loft Model on a premium cul-de-sac lot in the sought after 55+ community of the Four Seasons at Kent Island. Open Concept main level with 10' ceilings. Kitchen features a huge center island with sink, stainless steel appliances, quartz countertops complete with Rigid Core luxury vinyl plank floors. Dry bar option with additional cabinetry. Primary owner's suite with ceiling fan, ensuite bathroom with double vanity and luxury walk-in shower. Primary closet and bedrooms with custom closet shelves and organizers. Second level features 3rd bedroom with full bath and game room, along with a “sky basement” containing tons of storage and individually conditioned space. Fabulous Sunroom with screened in porch leading to a gorgeous exterior complete with stone patio, cozy propane fire pit surrounded by extensive landscaping. Additional features include: water pressure booster, professionally painted garage with, floor poly coat, and suspended storage racks. Custom window treatments. Home wired for Wifi/HDMI/Security. Too many upgrades to list! Close to Annapolis/DC and Eastern Shore.

Listed by Scott J Swahl of Redfin Corp

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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190 Sailcloth Way Chester MD 21619

Chester, MD190 Sailcloth Way

Price$749,900

Est. Mortgage: $/month

MLS Number MDQA2000061

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

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.

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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122 Evelyne St Chester MD 21619

Chester, MD122 Evelyne St

Price$699,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDQA2000968

  • Single Family
  • LocationType River
  • Address 122 Evelyne St
  • Square Feet 3291
  • Bathroom 3

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

Listed by Tricia Z Wilson of Chaney Homes,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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

Pending

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: 3.05% last updated on Oct 14, 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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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
  • Bathroom 3
  • Square Feet 2446
  • Bedrooms 4

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

Listed by Angela T Lucas and Tiffany a Lucas of Samson Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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
  • Year Built 2022
  • Bedrooms 3
  • Bathroom 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: 3.05% last updated on Oct 14, 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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115 Bentons Pleasure Rd Chester MD 21619

Chester, MD115 Bentons Pleasure Rd

Price$645,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDQA2001192

  • Single Family
  • Square Feet 2880
  • Bedrooms 4
  • Year Built 1998
  • Bathroom 3

Stunning Colonial located in Kent Island's Bentons Pleasure Community - Custom Built with sturdy 2 x 6 Construction, One Acre Lot backs to trees & provides peaceful views! Welcome Guests onto the Front Porch with seating area - then come inside and enter into the Large Tile Foyer. Spacious floor plan includes Formal Living and Dining Rooms. You will fall in Love with the beautifully remodeled Gourmet Kitchen w/ Island - Tile flooring, New Cabinets, SS Appliances- include Cooktop, Bosch Dishwasher, Double Wall Oven (including 1 steamer), Pantry, crown molding and much more! Family Room opens to Relaxing Screened Porch - perfect for unwinding after long day or eating some delicious steamed crabs! Walk out onto the expanding Deck and Private Pool! Dont miss the 20' x 50' Pole Barn. Second Floor includes elegant Brazilian MahoganyFloors. Master Suite is your private Oasis, walk in closet and Bonus Room - perfect for nursery, workout room or office! Retreat to the Private Bath with Soaking Tub, walk in shower and double vanity! Second Floor Laundry Room walks out to large Second Story Deck - incredible expansive views! Three additional spacious bedrooms. Two Car Garage is oversized and includes space for workshop. Home includes Hi Efficiency Propane Heat and Central AC (2017) - with Two Zones. Hot Water is Tankless & Propane. New Roof 2020-50 Year Architectural Shingles. Encapsulated Crawl Space (2019). Pool (2017) No HOA.

Listed by April L Heim of Rosendale Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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112 Saltworks Dr Chester MD 21619

Chester, MD112 Saltworks Dr

Price$645,000

Est. Mortgage: $/month

MLS Number MDQA2000962

  • Single Family
  • Address 112 Saltworks Dr
  • Year Built 2021
  • Square Feet 2438
  • Bedrooms 2

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

Listed by Frances Middleton of Douglas Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

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 October 20, 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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