Search Homes:

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.

Search Kent Island Real Estate in Chester MD

Call Chuck Mangold at 410-924-8832 with any questions or to schedule a private tour.

Narrow Your Search
Waterfront Homes | Water View HomesSingle Family Homes | Homes with Land | Luxury Homes | Land

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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

2888 Cox Neck Rd Chester MD 21619

Chester, MD2888 Cox Neck Rd

Price$1,490,000

Est. Mortgage: $/month

Active With Contract

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

2838 Cox Neck Rd Chester MD 21619

Chester, MD2838 Cox Neck Rd

Price$1,399,999

Est. Mortgage: $/month

Pending

MLS Number MDQA144822

  • Single Family
  • LocationType Bayfront
  • Address 2838 Cox Neck Rd
  • Bathroom 4
  • Bedrooms 4

The Perfect 10! Nestled in the Private Southwind Community, this Contemporary Style 4400sq ft home sits on 1.20 acres and BOASTS 180' of unobstructed views of the mouth of the Eastern Bay where Novel Eastern Shore Sunsets can be seen nightly! Whether working, learning or just spending more time at home, this home offers an expansive amount of space with impeccable water views from nearly EVERY window - VACATION WHERE YOU LIVE! The first floor features an OPEN floor plan with Gleaming Hardwood floors throughout the Sunken Living room, Dining room, Hallways and Gourmet Kitchen. Soaring Ceilings and a WALL of windows with breathtaking Eastern Bay Water views are the highlights of the Great Room off the Kitchen & also features a wood burning fireplace & ceramic tiled floors. Take the party outside to an entertainers PARADISE complete w/ a 14x18 Deck, Custom Fire Pit & Patio by the Waterfront, 150ft Commercial Grade Pier w/ 2 boat lifts, electric, water, & secured Bench to take in the scenery the Bay has to offer! Upstairs features a Master Suite w/ sitting area, balcony overlooking the waterfront, en suite full bath w/ soaking tub & HUGE walk in closet, & down the hall you'll find the 2nd & 3rd bedrooms w/ Jack&Jill bath & the Laundry Room w/ Pull down Attic Stairs for additional storage. The "West Wing" of the home boasts a 1st floor bedroom & full Bath, an immaculate 2 car oversized garage & and living space above the garage w/ a sitting room, 2 offices, bonus room & 4th full bath which easily could be converted to in-law quarters w/ it's own separate entrance! The list goes on for ALL that this EXTREMELY WELL MAINTAINED home has to offer - check out the YouTube video tour & schedule an in-person showing today!

Listed by Jennifer Norfolk of Coldwell Banker Waterman Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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

228 Bentons Pleasure Rd Chester MD 21619

Chester, MD228 Bentons Pleasure Rd

Price$1,075,000

Est. Mortgage: $/month

Active With Contract

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

208 Winchester St Chester MD 21619

Chester, MD208 Winchester St

Price$968,000

Est. Mortgage: $/month

MLS Number MDQA144662

  • Single Family
  • Address 208 Winchester St
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3888

WOW!!! Gorgeous coastal home. Stunning views of the Chester River from 3 levels of porches in sought after Gibson's Grant. BRAND new barely lived in, UPGRADES galore. The home boasts 3 living spaces one on each level. Four spacious bedrooms, one on the main level, 3.5 baths, office nook, custom mud room, laundry room, custom master closet, gourmet kitchen with quartz counter tops, stainless appliances, premium engineered hardwood, tray ceilings, 10 foot ceilings. Tons of storage in over-sized conditioned crawl space and a 2 car garage with plenty of off street parking. Open concept living at its best! This home is one of only 5 that sit directly on the Chester River, steps from the community pier, pool, club house and gym! Easy access to Rt 50 and minutes to the Bay Bridge. THIS ONE IS A 10+ MAGAZINE WORTHY PROPERTY. COASTAL LIVING AT ITS FINEST Koch Homes - Kensington Model

Listed by Michelle O Bowman of Chaney Homes, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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

115 Parks Rd Chester MD 21619

Chester, MD115 Parks Rd

Price$825,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDQA144470

  • Single Family
  • LocationType Bayfront
  • Address 115 Parks Rd
  • Bathroom 4
  • Bedrooms 4

Looking for waterfront with your own guest home or income property? From the second you walk in the door you'll enjoy the open water views. This one level, open concept, water front home offers sunset views over Cox Creek. You will be taken by the generous amounts of living space and quickly be drawn straight back to beauty of the creek. Looking for a main level master? This has it! Looking for sunset views over the water? Check! Looking for peace of mind? These items can help....the main house has a new roof, new appliances (including HVAC and h20 heater), new windows, new kitchen cabinets, new bathrooms, & new flooring. Does a guest house, Au pair suite, or a possible income property interest you? The property includes a quaint 500 square foot, 1 bedroom cottage with it's own utilities, kitchen, bath, and living space. The lovely neighborhood of Bentons pleasure will welcome you and invite you to enjoy this little slice of heaven.

Listed by DEE DEE R MCCRACKEN and Lisa A Barton of Coldwell Banker Residential Brokerage

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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

202 Claiborne St Chester MD 21619

Chester, MD202 Claiborne St

Price$759,000

Est. Mortgage: $/month

MLS Number MDQA145212

  • Single Family
  • Address 202 Claiborne St
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3424

PLEASE CLICK ON VIRTUAL TOUR FOR INTERACTIVE FLOOR PLAN**Absolutely Stunning Custom Home**Open Floor Plan w/Red Oak Wide Plank Solid Hardwood Flooring on Main Level**Main Level Primary Suite w/Private Office**Breakfast Room leads onto Sun Room w/Custom Brick Pavers**Sun Room has Custom Sheers for Privacy**Sliders and Skylights let the Sun Shine In**Kitchen has Custom Cabinets w/Custom Pulls**Large Pantry**Welcoming Dining Area w/Wainscoting**Private Rear Yard w/Cedar Fencing**Large Stairway to Second Level**3 Bedrooms and 2 Full Baths on 2nd Level**Sound System**Custom Coastal Shutters on ALL Windows**Calmingly Painted Coastal/Warming Colors**Lovely Amenities of Gibson's Grant...Pool, Club House, Walk Path, Kayak Areas, Pier**Close to Restaurants/Shopping**Easy Access to Major Highways but Private Neighborhood Feel**

Listed by Deborah A Savoie of Long & Foster Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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: 2.87% last updated on Sep 17, 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

0000 Winchester Street Chester MD 21619

Chester, MD0000 Winchester Street

Price$732,990

Est. Mortgage: $/month

MLS Number MDQA143162

  • Single Family
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3516
  • Year Built 2020

Do not miss out on building a Kingston 3 story in Gibson's Grant . 4 bedrooms, 3. full 1 half baths, 10 foot first floor ceilings, 2 car garage. 2nd floor loft/tv area. 3 rd floor studio. Do not miss out living in Gibson Grant with Community center, swimming pool. fitness center, kayak racks. Fishing and crabbing pier. This home is to be built base price. Pictures from a past Kingston 2 story home & 3 story model home.

Listed by Jennifer Kenney of Koch Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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

102 William Alley Aly Chester MD 21619

Chester, MD102 William Alley Aly

Price$729,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDQA144672

  • Single Family
  • LocationType River
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2804

PLEASE CLICK ON VIRTUAL TOUR ICON FOR THE TWO TOURS...AERIAL FOOTAGE AND INTERACTIVE FLOOR PLAN**Absolutely Stunning Home w/Charm Galore**Upgraded Elevation on Porches**Finished Garage Studio can be 4th Bedroom**Box Bay Window in Dining and Home Office**Coffered Ceiling in Great Room Overlooking Gourmet Kitchen**Custom Bertch Kitchen Cabinets**Gas Cooking**Enlarged Island w/Storage Underneath**Wine Fridge and Warming Drawer**Open Floor Plan into Great Room w/Gas Fireplace**Surround w/Speakers**Main Floor Leads to Private Yard w/Plants Flowering in All Seasons**Owner's Suite has Sitting Room w/Views of Water**Relax on Front Porch off of Owner's Suite**Owner's Bath Upgraded Tile and Vanity w/Frameless Shower**New Toilet and Fixtures**Anderson Silver Line Windows**Upgraded Hall Bath on Second Level w/Scott Bros Vanity/New Toilet/Fixtures/Tile to Ceiling and Flooring**Conditioned Crawl Space w/Storage and Polyurethane Floors**Two Car Garage w/Lifetime Warranty Epoxy Flooring**Flow Wall System**Water Views from Front of Home**Community has Pool, Club House, Pier, Kayak Ramp, etc...**Close to Shopping**AERIAL FOOTAGE CAN ALSO BE VIEWED ON YOU TUBE**

Listed by Deborah A Savoie and Christina Merrill of Long & Foster Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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.

Virtual TourSave 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 September 21, 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.

Get In Touch Today

Contact Chuck