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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: 3.07% last updated on Jul 2, 2020
* 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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2888 Cox Neck Rd Chester MD 21619

Chester, MD2888 Cox Neck Rd

Price$1,490,000

Est. Mortgage: $/month

MLS Number MDQA142834

  • Single Family
  • Address 2888 Cox Neck Rd
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3539

Broad water views and light fill this elegant contemporary located in the desirable community of Southwind. This custom built home has an outstanding floor plan offering 3539' of living space. Walls of glass surround the waterside 2 story family room which is open to the gourmet kitchen with Granite counter tops, stainless appliances and island. The kitchen is large enough for a comfy table and chairs. There is a separate dining room too. Upstairs are 4 bedrooms and 3 full baths. Two bedrooms are connected with Jack and Jill bath. The third bedroom has an attached bath with hallway entrance. Lovely master suite is spacious with sitting room, huge bath, his and her walk in closets and waterside 32 x 14 private deck. Hardwoods and water views throughout. Exterior shower enclosure and 3 car garage. Located at end of community in cul de sac for more privacy and steps from clubhouse, tennis cts and community water features.

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: 3.07% last updated on Jul 2, 2020
* 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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2838 Cox Neck Rd Chester MD 21619

Chester, MD2838 Cox Neck Rd

Price$1,399,999

Est. Mortgage: $/month

MLS Number 1002054676

  • Single Family
  • LocationType Creek/Stream
  • Address 2838 Cox Neck Rd
  • Bathroom 4
  • Bedrooms 4

New Price! Stunning Southwind home w/living area of 4,248 sq. ft. Gourmet kitchen off great room with soaring windows to enjoy the Eastern Bay views. Hardwood floors, granite counters, formal dining area - it's all here! First floor bedroom with 3 additional bedrooms up. Office wing on second floor; great for working from home or could be add'l bedroom. Huge master with sitting room. Radiant heat. Commercially constructed pier and boat lifts and waterside "adirondeck." Community club house, tennis, beach, scenic trails. Motivated sellers.

Listed by Merry M Tobin of RE/MAX Executive

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$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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2903 Cox Neck Rd E Chester MD 21619

Chester, MD2903 Cox Neck Rd E

Price$1,350,000

Est. Mortgage: $/month

MLS Number MDQA142750

  • Single Family
  • LocationType Bayfront
  • Address 2903 Cox Neck Rd E
  • Bathroom 4
  • Bedrooms 5

Great, Custom Colonial on Crab Alley Bay, located in the community of Southwind. Home features large open spaces on first and third floor, custom kitchen, new master bath, freshly painted throughout, Tile & Hardwood, 5 bedrooms & 3.5 baths. Use your flex space on the third floor for exercise room, home theater, run a home business or much more. Watch the beautiful sunrises, kayak and take your boat out for a spin from your pier. Set up for outdoor living with a beautiful built in pool, large screened porch.Virtual Tour Link https://thru-the-lens-ivuf.view.property/1277650?idx=1

Listed by DEE DEE R MCCRACKEN of Coldwell Banker Residential Brokerage

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$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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 Kirwans Landing Ln Chester MD 21619

Chester, MD120 Kirwans Landing Ln

Price$1,250,000

Est. Mortgage: $/month

Pending

MLS Number MDQA143330

  • Single Family
  • LocationType Creek/Stream
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 5394

Luxurious Kirwans Landing Waterfront-Expansive Views & Beautiful Sunsets. Private Pier w/multiple slips, boat lift, rip rapped shoreline, 2-3' MLW, Southwest exposure. Graciously appointed three story living- all levels accessible by Elevator. Architecturally designed renovations- this home is an entertainers delight. First floor Formal Dining Room, sunken Living Room w/Brick Fireplace opens to WF Deck. Gorgeous Gourmet Kitchen - Granite counters & backsplash, breakfast bar, center island w/Gas cooktop, double wall oven, wet bar & large pantry. Family Room w/Cozy wood stove insert opens to WF Deck. Waterfront Sunroom w/vaulted ceiling, skylights, walls of glass absorb the stunning views of the water and spectacular outdoor living area. Gorgeous Gunite Pool (Large 50' x 22' with 11' x 10' shallow area), heated & waterfall - surrounded by stone patio and professional landscaping. Second floor with oversized Master Suite - breathtaking waterfront views from private balcony (awning) perfect for sipping your morning coffee, California Closets and a Master Bath Oasis-Designed to Relax and Unwind with whirlpool tub, shower, double vanity and more! Not finished yet -Master also has a spacious study with kitchenette! Second Bedroom includes waterfront balcony. Third level is perfect In Law/Au Pair Suite - with two bedrooms, full & half baths, Kitchen, Dining and Living Area. Additional features include Two Laundry Rooms - 1st and 2nd floors, whole house propane generator, climate controlled Garage, tankless instant Hot Water Heater, Three zoned Heat Pumps, encapsulated conditioned crawl space. Ideally located in the private community of Kirwans Landing -nestled between Kirwans and Goodhand Creek - Community has private Marina! Close to Kent Narrows, Fine Dining, Shopping, Terrapin Nature Trail, walk to Beach on Chesapeake Bay, Bay Bridge Airport and more! Live your best life and Love where you live- It's a Shore Thing!

Listed by April L Heim of Rosendale Realty

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$
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$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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2867 Cox Neck Rd Chester MD 21619

Chester, MD2867 Cox Neck Rd

Price$1,150,000

Est. Mortgage: $/month

Pending

MLS Number MDQA140280

  • Single Family
  • Address 2867 Cox Neck Rd
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 6068

TRUSTEE SALE ! MUST SELL! One level living at it's finest. Breathtaking water views of Eastern Bay. large open living concept. Screened porch over looks private in ground pool, and flat yard leading to your own private dock. Located in Southwinds, this home will not disappoint!

Listed by Michael Buckmaster of A Real Estate Advantage

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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228 Bentons Pleasure Rd Chester MD 21619

Chester, MD228 Bentons Pleasure Rd

Price$1,075,000

Est. Mortgage: $/month

MLS Number MDQA143022

  • Single Family
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3571
  • Year Built 2005

Summer Is HERE!! ... Better Hurry to This GORGEOUS Custom-Built Kent Island WATERFRONT! It's what 'Island Living' is All About! Private Pier, w/ Boat Lift & Jet Ski Lift Just Begging For Playtime! Boating, Jet Ski, Crabbing, Fishing- all from your back door! Your Private Island Oasis! Million-Dollar Sunsets & SPACE! Boasting Over 3200 sq ft of Exquisite Craftsmanship, Millwork & Style- the Open, Generously Sized Floor-Plan Affords Something for All! Inviting, 2-Story Foyer Greets Guests, Leading to Spacious Family Room w/ Wall of French Doors to Stunning Waterfront Views! Stacked Stone Gas Fireplace is one of FOUR for Cozy Nights! Gourmet Kitchen w/ Gleaming Granite, Custom Cabinetry & Large Breakfast Bar Opens to Morning Room w/ Table Space for Waterfront Dining! Main-Level Master Suite w/ Fireplace & Sliders to Private Waterfront Patio! Spa-Like Master Bath & Huge Walk-in-Closet! Main-Level Den w/ Fireplace & Built-Ins Makes Perfect Office or Tucked-in Sanctuary! 3 Upper-Level Bedrooms Each Attached to Full Bath are accessed over Catwalk w/ Inescapable Water-Views! Private Waterfront Balcony off 2nd Bedroom will have Guests Never Wanting to Leave! Large Private Bath & Fireplace. Jack-and-Jill shared Full Bath for Large 3rd/4th Bedrooms. Ample Storage! Over-Sized 2-Car Garage, Walk-in-Storage Room Above & Generously-Sized Closets Throughout! 10 Mins from Bay Bridge- 1-Hr DC. 20 Mins by Boat to St Michaels! Claim this Stylish Beauty Soon... Before your competition is living YOUR Waterfront Dream!

Listed by Jennifer S Chaney of Chaney Homes, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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328 Bentons Pleasure Rd Chester MD 21619

Chester, MD328 Bentons Pleasure Rd

Price$915,000

Est. Mortgage: $/month

MLS Number MDQA142874

  • Single Family
  • LocationType Creek/Stream
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1725

**REDUCED**!! This truly special waterfront home has been the joy of the Owners (and theirextended family) for more than 30 years. One visit and you will know why- It is what everyoneDREAMS about when they imagine their perfect "Shore Home". Placed with a commanding view ofCox Creek (and truly spectacular sunsets), this 3 Bedroom, 2-1/2 bath gem was designed tocelebrate the outdoors. The Entry Foyer opens into the Living Room with a large brick fireplace.The two large bedrooms have their own beautifully detailed bathrooms. The third smaller,upstairs bedroom would also make a terrific home office, nursery or craft room.There is anenormous screened porch that connects to the wonderful gourmet kitchen. It opens onto acovered porch that has steps to a slate tile patio (partially heated along with the steps and frontsidewalk!). The expansive yard sits well above the flood plain and has some mature trees thatshade the second floor balcony. The concrete pool is a shady oasis that has outstanding,panoramic water views. The dock has TWO boat lifts and 4'+ MLW. Great crabbing, fishing andwatersports await! There is truly nothing quite like it! *Recent appraisal by May and Assoc.indicate $1M valuation!

Listed by Steven S Saunders of Coldwell Banker Waterman Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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144 Watermans Cove Ln Chester MD 21619

Chester, MD144 Watermans Cove Ln

Price$740,000

Est. Mortgage: $/month

Pending

MLS Number MDQA141652

  • Single Family
  • Bathroom 3
  • Bedrooms 4
  • Year Built 2019
  • Acreage 0.34

Beautiful waterfront home to be built. Enjoy the serenity of Cox Creek in the new community of Waterman's Cove. This enclave of nine private home sites is nestled on a quiet dead end street. Private pier. 4 bedrooms. 2.5 baths. Kitchen with granite counter tops and stainless steel appliances. Hardwood floors. First floor master bedroom with attached bath. Large 2nd story waterfront office or media room. Rear composite deck for outdoor entertaining overlooks water. Concrete driveway and nice attached garage. Located just a short mile off Rt. 50. HOA includes lawn care and trash removal.

Listed by David G Dauses Jr. of Coldwell Banker Waterman Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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102 Winchester St Chester MD 21619

Chester, MD102 Winchester St

Price$727,000

Est. Mortgage: $/month

MLS Number MDQA143966

  • Single Family
  • Address 102 Winchester St
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3928

102 Winchester Street is a gorgeous, water-oriented home located in the Gibson's Grant community. This two-year-old home shows like a model and is ready for the next owners with four bedrooms, beautiful detailing, and a fenced yard. Walk to the community fishing pier, pavilion, and outdoor fire pit ~ the waterfront lifestyle is readily accessible. As you step inside the foyer you immediately recognize the inherent charm of this spectacular home. To the right of this light-filled space is the formal living room or home office. Down the hall is the family room with shaker style wainscoting, crown molding, and stacked-stone gas fireplace with stone hearth and mantel. This space flows seamlessly into the informal dining space, just off the kitchen, with built-in prep bar and storage. The gourmet kitchen has stunning grey cabinetry, a large center island with gas cooktop, double wall oven, and gorgeous granite counters. The breakfast bar is the perfect spot for a quick bite to eat or for guests to sit while entertaining. More formal meals are also an option in the beautifully trimmed dining room. This level also has a powder room, a separate mudroom with laundry, and access to the two-car garage with a finished upstairs bonus room. Upstairs, the owner's suite has a sitting area, walk-in closet, and a luxurious bath with soaking tub and separate tiled shower. The suite enjoys private access to the second level porch that runs the entire length of the home. Three additional bedrooms and a hall bathroom can also be found on this level. The third floor has been finished and includes a bathroom; it makes a great spot for guests, a home office, a home gym, or additional living space. Desirable Gibson's Grant offers brick sidewalks and alleys for garage access providing this unique community a warm and inviting appeal. Enjoy summers at the community pool or launch your kayak or canoe on Macum Creek for a day of exploring. Low-maintenance living with access to water-oriented amenities make 102 Winchester Street a must see! Conveniently located, this home is just a quick drive to major commute routes, a short walk to the Kent Island Community Trail, and minutes to restaurants, shopping, and more! Call the waterfront experts for your private tour today! Watch the Virtual Open House!

Listed by Charlie B Buckley and Reid Buckley of Long & Foster Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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

106 Kirwans Landing Ln Chester MD 21619

Chester, MD106 Kirwans Landing Ln

Price$725,000

Est. Mortgage: $/month

Pending

MLS Number MDQA144056

  • Single Family
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3706
  • Year Built 1997

Welcome to this meticulously maintained traditional home in the sought after neighborhood of Kirwan's Landing with water and boat access. This 3,700 +/- sqft home boasts 4 bedrooms, 2.5 baths, hardwood floors, granite countertops, stainless steel appliances, Andersen double hung windows, 2x6 construction, a huge master suite, 10' ceilings, mud room, bright 4 seasons room and gas fireplace. Outside you'll enjoy the large wrap around front porch, 3 bay garage plus detached garage, large rear deck and fenced yard that backs up to trees and County owned wetlands. Few homes become available in Kirwan's Landing so don't let this one get away!

Listed by Fred I Rider III of TTR Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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

152 Watermans Cove Ln Chester MD 21619

Chester, MD152 Watermans Cove Ln

Price$699,900

Est. Mortgage: $/month

Active With Contract

MLS Number MDQA141362

  • Single Family
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2400
  • Year Built 2019

Kent Island's newest exclusive private waterfront community, peacefully located on Cox Creek. Enjoy a deep water private pier, beautiful sunset views across the creek, and easy access by boat to Eastern Bay. 4 bedrooms with a spacious master suite, huge open kitchen/dining/family room, sunroom, home office, and mud room off garage. Large rear composite deck for outdoor entertaining. Concrete driveway and 2 car garage. Just over 1 mile from Rt. 50 for easy commute and shopping access. Take a deep breath and delight in the serenity of the Eastern Shore. HOA handles lawn care and trash removal. HOME IS READY FOR DELIVERY!

Listed by David G Dauses Jr. of Coldwell Banker Waterman Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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 2020 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 4, 2020. 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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