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1719 Harbor Drive, Chester image
1719 Harbor Drive, Chester $1,300,000

Escape the ordinary in this one-of-a-kind waterfront masterpiece on Cox Creek. Designed for those who refuse to settle for "cookie-cutter," this residence seamlessly blen...

  • 3 Beds
  • 5 Baths
Courtesy of Chesapeake Real Estate Associates, LLC

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Selling Office: .

2702 Sherman Dr, Chester image
2702 Sherman Dr, Chester $989,000

Discover the extraordinary waterfront oasis of 2702 Sherman Dr. in Chester. This remarkable residence, featuring 5 bedrooms, 2 full bathrooms, and 2 half bathrooms, has u...

  • 5 Beds
  • 4 Baths
Courtesy of Samson Properties

Listing courtesy of Samson Properties. Contact: 7033788810

1906 Stevens Drive, Chester image
1906 Stevens Drive, Chester $471,500

Spacious and beautifully updated ranch-style home offering over 2,000 square feet of comfortable one-level living. This versatile layout features 3 bedrooms and 2 full ba...

  • 3 Beds
  • 2 Baths
Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

1848 Harbor Drive, Chester image
1848 Harbor Drive, Chester $480,000

Don’t miss this charming Cape Cod-style home in the highly desirable Harbor View neighborhood of Chester. Thoughtfully designed and move-in ready, this home offers the pe...

  • 3 Beds
  • 2 Baths
Courtesy of EXP Realty, LLC

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: .

1838 Sherman Drive, Chester image
1838 Sherman Drive, Chester $379,000

Nestled in the heart of Chester, Maryland on the beautiful Eastern Shore, this charming rancher offers comfort and convenience. Inside, a bright and inviting interior fea...

  • 3 Beds
  • 2 Baths
Courtesy of Keller Williams Realty Centre

Listing courtesy of Keller Williams Realty Centre. Contact:

Selling Office: .

2645 Cox Neck Rd, Chester image
2645 Cox Neck Rd, Chester $399,500

Welcome to 2645 Cox Neck Road, a move-in ready home in the desirable Harbor View Community of Chester. Offering 3 bedrooms, 1.5 baths, and situated on a spacious .34-acre...

  • 3 Beds
  • 2 Baths
Courtesy of Compass

Listing courtesy of Compass. Contact: (410) 429-7425

2513 Cecil Dr, Chester image
2513 Cecil Dr, Chester $1,350,000

The locals called it Keister's Folly. In the mid-1940s, Dr. Keister built a barn on Kent Island overlooking Cox Creek, hoping to raise Black Angus cattle on 25 acres. The...

  • 5 Beds
  • 2 Baths
Courtesy of Real Broker, LLC - Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

1914 Anchorage Drive, Chester image
1914 Anchorage Drive, Chester $299,900

Property is a combination of an Estate Sale (being sold As-Is) and a pre-approved short sale. 3Bd/2ba rancher on approximately .4 acres. Well and septic. Livrm, dinrm, f...

  • 3 Beds
  • 2 Baths
Courtesy of Century 21 Downtown

Listing courtesy of Century 21 Downtown. Contact:

Selling Office: .

1921 Harbor Drive, Chester image
1921 Harbor Drive, Chester $519,900

Just completed brand new home! Energy efficient! The comfort of knowing that everything is new! One year warranty included! The fully finished daylight basement offe...

  • 3 Beds
  • 3 Baths
Courtesy of Coldwell Banker Waterman Realty

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: .

2613 Cecil Drive, Chester image
2613 Cecil Drive, Chester $900,000

BIG REDUCTION! Welcome to easy waterfront living on Kent Island. Western exposure to beautiful sunsets. Tucked away on a quiet street, this 5-bedroom, 3.5-bath home offer...

  • 5 Beds
  • 3 Baths
Courtesy of Benson & Mangold, LLC

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

1803 Chester Drive, Chester image
1803 Chester Drive, Chester $385,000

Adorable rancher on Kent Island in the community of Harbor View! Featuring 4 beds, 2 baths, and private driveway. Enjoy the large fenced yard with deck, shed, and firepit...

  • 4 Beds
  • 2 Baths
Courtesy of Keller Williams Legacy

Listing courtesy of Keller Williams Legacy. Contact:

Selling Office: .

1870 Harbor Drive, Chester image
1870 Harbor Drive, Chester $310,000

Discover this charming 2-bedroom, 1-bath home in Harbor View featuring beautiful wood floors, a brand-new roof, updated windows, and a spacious rear deck overlooking a la...

  • 2 Beds
  • 1 Baths
Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

2644 Cecil Drive, Chester image
2644 Cecil Drive, Chester $382,000

Welcome to this Harbor View home offering approximately 1,108 square feet of comfortable, updated, one-level living on a spacious 1/3 ac lot. The backyard is fully fenced...

  • 3 Beds
  • 2 Baths
Courtesy of Realty Navigator

Listing courtesy of Realty Navigator. Contact:

Selling Office: .

1872 Harbor Dr, Chester image
1872 Harbor Dr, Chester $455,000 ▼

Harbor View Community | Corner Lot | Renovated Rancher with Room to Grow If you’ve been searching for a home where the work is already done and you can move in without wo...

  • 3 Beds
  • 2 Baths
Courtesy of Cross Street Realtors LLC

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

1839 Harbor Drive, Chester image
1839 Harbor Drive, Chester $350,000

MAJOR REDUCTION! Opportunity Knocks Welcome to Harbor View on Kent Island - Just 7 minutes from the Bay Bridge This oversized ranch style home boasts 4 Bedrooms and 2 Ful...

  • 4 Beds
  • 2 Baths
Courtesy of Taylor Properties

Listing courtesy of Taylor Properties. Contact:

Selling Office: .

2653 Cox Neck Road, Chester image
2653 Cox Neck Road, Chester $224,000

Welcome to 2653 Cox Neck Rd—a beautifully renovated rancher nestled in the heart of Kent Island. This charming 3-bedroom, 2-bathroom home offers the ease of single-level ...

  • 3 Beds
  • 2 Baths
Courtesy of Eastern Shore Real Estate, LLC

Listing courtesy of Eastern Shore Real Estate, LLC. Contact:

Selling Office: .

1906 Harbor Dr, Chester image
1906 Harbor Dr, Chester $429,900 ▼

*PRICE IMPROVEMENT!* Welcome to this beautifully renovated ranch-style home offering 4 bedrooms, 2 full bathrooms, and a spacious open floor plan designed for modern liv...

  • 4 Beds
  • 2 Baths
Courtesy of Five Star Real Estate

Listing courtesy of Five Star Real Estate. Contact:

1903 Churchhill Lane, Chester image
1903 Churchhill Lane, Chester $405,000

Welcome Home to 1903 Churchhill Lane! This Beautifully updated Rancher offers the space you need to create a life you desire. Boasting an array of sleek finishes throug...

  • 4 Beds
  • 3 Baths
Courtesy of Alberti Realty, LLC

Listing courtesy of Alberti Realty, LLC. Contact:

Selling Office: .

1916 Stevens Dr, Chester image
1916 Stevens Dr, Chester $470,000 ▼

New and improved price! This beautifully updated and well maintained home delivers exceptional value in the highly desirable Harbor View community—just two miles east of ...

  • 3 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

2723 Cox Neck Road, Chester image
2723 Cox Neck Road, Chester $447,500

Rates are coming down, time to buy! - 100% Financing is Available!!! This newly constructed home features 4 bedrooms and 2.5 baths. Offering a first-floor bedroom or thi...

  • 4 Beds
  • 3 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

1771 Harbor Drive, Chester image
1771 Harbor Drive, Chester $735,000

This beautifully crafted waterfront home boasts five spacious bedrooms and 2.5 baths, offering ample space for comfortable living. The expansive layout includes multiple ...

  • 5 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

1773 Harbor Drive, Chester image
1773 Harbor Drive, Chester $610,000

Custom built waterfront home in Harbor View! Come on in and make it your own! Excellent views of the water from every room in the house! Kitchen with lots of storage and ...

  • 3 Beds
  • 3 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

2008 Palm Drive, Chester image
2008 Palm Drive, Chester $500,000

New Price Improvement! Cape Cod with spacious wrap around porch! Upon entering, you will be greeted with hardwood floors throughout most of the main level. The focal p...

  • 3 Beds
  • 3 Baths
Courtesy of EXP Realty, LLC

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: .

1809 Stevens Drive, Chester image
1809 Stevens Drive, Chester $445,000

Best deal on Kent Island! Beautiful 4 Bedroom 2 1/2 bath Cape on over 1/2 acre in peaceful Harbor View. Airy and spacious, this terrific home boasts 2 Bedrooms plus Full...

  • 4 Beds
  • 3 Baths
Courtesy of Taylor Properties

Listing courtesy of Taylor Properties. Contact:

Selling Office: .

1757 Harbor Dr, Chester image
1757 Harbor Dr, Chester $1,294,800 ▲

*****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! New Home, New Pier, New Pool!!!!!The Blue Heron is a new home design offered by Lacrosse H...

  • 4 Beds
  • 4 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

2707 Cox Neck Road, Chester image
2707 Cox Neck Road, Chester $435,000

Welcome to Harborview, a long established community on Maryland's eastern shore, home of some of the best seafood on the eastern seaboard! Come see everything that living...

  • 3 Beds
  • 3 Baths
Courtesy of Douglas Realty LLC

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: .

2614 Ellicott Drive, Chester image
2614 Ellicott Drive, Chester $495,000

Like-New Construction | Turn-Key Living | Prime Chester Location. Welcome to 2614 Ellicott Drive, a stunning 2023-built home that blends modern design with everyday comf...

  • 3 Beds
  • 2 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

1770 Harbor Drive, Chester image
1770 Harbor Drive, Chester $685,813

RARE OPPORTUNITY ON KENT ISLAND> FULL BASEMENT!! One of our most popular designs, the Doral offers formal ( office space) and informal living areas with lots of room for ...

  • 4 Beds
  • 3 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

2747 Cecil Drive, Chester image
2747 Cecil Drive, Chester $350,000

MAJOR PRICE IMPROVEMENT!!!***Seller has requested an offer deadline of 5/15/25 at noon*** Welcome to this charming 3-bedroom, 2-bath home nestled in the desirable Harbor...

  • 3 Beds
  • 2 Baths
Courtesy of Anne Arundel Properties, Inc.

Listing courtesy of Anne Arundel Properties, Inc.. Contact:

Selling Office: .

1833 Harbor Drive, Chester image
1833 Harbor Drive, Chester $350,000

Located in Harbor View, this cutie has 3 bedrooms and 2 full bathrooms. There's views of Cox Creek from both levels. This home has been freshly painted with new carpet an...

  • 3 Beds
  • 2 Baths
Courtesy of Chaney Homes, LLC

Listing courtesy of Chaney Homes, LLC. Contact:

Selling Office: .

2709 Cox Neck Road, Chester image
2709 Cox Neck Road, Chester $430,000

Charming 4-Bedroom, 2.5-Bath Cape Cod with Modern Updates! Discover this beautifully maintained 4-bedroom, 2.5-bath Cape Cod, offering classic charm with modern updates ...

  • 4 Beds
  • 3 Baths
Courtesy of Keller Williams Realty Centre

Listing courtesy of Keller Williams Realty Centre. Contact:

Selling Office: .

2612 Cecil Drive, Chester image
2612 Cecil Drive, Chester $575,000

Discover this captivating Colonial with partial water views, ready to welcome you! You'll fall in love as you step inside this meticulously maintained beauty. A charming...

  • 4 Beds
  • 3 Baths
Courtesy of Rosendale Realty

Listing courtesy of Rosendale Realty. Contact:

Selling Office: .

1752 Harbor Drive, Chester image
1752 Harbor Drive, Chester $495,000

Seller is calling for highest and best offers by Tuesday, 2/4/25 at 5 p.m. 🏠 Beautifully Renovated Rancher on Large Corner Lot with Water Views 🏠 This stunning 3-bedroo...

  • 3 Beds
  • 2 Baths
Courtesy of Cummings & Co. Realtors

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: .

1907 Churchhill Lane, Chester image
1907 Churchhill Lane, Chester $418,000

None

  • 3 Beds
  • 2 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

1926 Sherman Drive, Chester image
1926 Sherman Drive, Chester $415,000

Photo's on the way !! Welcome to Kent Island. This 4 Bedroom 2 Bath property is move in ready, completely updated over the last couple years and it shows. Hardwood floors...

  • 4 Beds
  • 2 Baths
Courtesy of Rosendale Realty

Listing courtesy of Rosendale Realty. Contact:

Selling Office: .

1702 Harbor Drive, Chester image
1702 Harbor Drive, Chester $324,500

Amazing and affordable new price! Why rent when you can own your own home, This Kent Island charming rancher in Harbor View is a super cutie.* A newer roof in 2020 and en...

  • 3 Beds
  • 1 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

lot 16 & 17 Cecil Drive, Chester image
lot 16 & 17 Cecil Drive, Chester $259,063

2 lot package deal (lot 16 & 17 Cecil Drive) part of larger parcel 1934 Harbor Drive. The lots front on Cecil drive and afford the opportunity to build your new dream h...

Courtesy of Berkshire Hathaway Homeservice Homesale Realty

Listing courtesy of Berkshire Hathaway Homeservice Homesale Realty. Contact:

Selling Office: .

1830 Sherman Drive, Chester image
1830 Sherman Drive, Chester — Harborview Kent Island $390,000

The expanded ranch you have been waiting for just hit the market. Located in friendly, water oriented Harbor View neighborhood  this spacious home at over 2175 square fee...

  • 4 Beds
  • 3 Baths
Courtesy of Douglas Realty LLC

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: .

1823 Chester Drive, Chester image
1823 Chester Drive, Chester $290,000

Welcome to Harborview, a long established community on Maryland's eastern shore, home of the best seafood on the eastern seaboard! Says me who has lived here all my life!...

  • 3 Beds
  • 1 Baths
Courtesy of Cummings & Co. Realtors

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: .

2601 Ellicott Drive, Chester image
2601 Ellicott Drive, Chester $375,000

Welcome to 2601 Ellicott Drive, a delightful 3-bedroom, 1.5-bathroom home situated on a beautiful corner lot in Chester, MD. This cozy home has been lovingly maintained a...

  • 3 Beds
  • 2 Baths
Courtesy of Benson & Mangold, LLC

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

1815 Stevens Drive, Chester image
1815 Stevens Drive, Chester $610,000

Buyer failed to perform for home contingency. Welcome to 1815 Stevens Dr. Chester, MD—a home where elegance meets modern sophistication. This meticulously updated smart h...

  • 3 Beds
  • 3 Baths
Courtesy of Real Broker, LLC - Annapolis

Listing courtesy of Real Broker, LLC - Annapolis. Contact:

Selling Office: .

2719 Cox Neck Road, Chester image
2719 Cox Neck Road, Chester $415,000

Nestled on your .24-acre on a flat lot, your 3 bedroom 2 1/2 bath well maintained home in Harbor View awaits you! The main level hosts hardwood floors throughout and an o...

  • 3 Beds
  • 3 Baths
Courtesy of Compass

Listing courtesy of Compass. Contact:

Selling Office: .

2608 Cecil Drive, Chester image
2608 Cecil Drive, Chester $655,000

OPEN HOUSE FOR SUNDAY JULY 14TH IS CANCELLED / HOME IS UNDER CONTRACT! Discover your dream home right here on Kent Island! After admiring the luscious landscape of the e...

  • 3 Beds
  • 3 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

1806 Chester Drive, Chester image
1806 Chester Drive, Chester $420,000

Welcome to your dream ranch-style home in the picturesque Harbor View community. Nestled at the tranquil intersection of Cox Creek and Cox Neck Road, this charming reside...

  • 4 Beds
  • 2 Baths
Courtesy of Northrop Realty

Listing courtesy of Northrop Realty. Contact:

Selling Office: .

1903 Chester Drive, Chester image
1903 Chester Drive, Chester $425,000

Seller has accepted offer. In the process of signing contract. Waterview home nestled on scenic lot with generous acreage Natural wildlife haven with serene surroundings....

  • 3 Beds
  • 2 Baths
Courtesy of Lofgren-Sargent Real Estate

Listing courtesy of Lofgren-Sargent Real Estate. Contact:

Selling Office: .

1905 Cecil Court, Chester image
1905 Cecil Court, Chester $260,000

Effortless style meets classic charm! This single-story gem boasts open living on a peaceful green oasis. The large front yard provides ample space for outdoor activities...

  • 3 Beds
  • 1 Baths
Courtesy of EXP Realty, LLC

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: .

1808 Stevens Drive, Chester image
1808 Stevens Drive, Chester $420,000

Welcome home! This completely renovated rancher located in the desirable Harbor View neighborhood on Kent Island is a perfect blend of comfort and modern living. Step ins...

  • 4 Beds
  • 2 Baths
Courtesy of Engel & Volkers Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: .

1905 Roberta Drive, Chester image
1905 Roberta Drive, Chester $594,000

Welcome to the Island, 1905 Roberta Dr, Chester MD. This stunning home has been completely remodeled and is ready for new owners! Boasting over 2000 sq feet of living sp...

  • 3 Beds
  • 3 Baths
Courtesy of Clark & Co Realty, LLC

Listing courtesy of Clark & Co Realty, LLC. Contact:

Selling Office: .

1752 Harbor Drive, Chester image
1752 Harbor Drive, Chester $275,000

Harbor View - INVESTOR ALERT! This property needs work and upgrading. The home has MOLD on some of the walls. The crawl space has MOLD! No access to the crawlspace f...

  • 3 Beds
  • 2 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

2616 B Cecil Drive, Chester image
2616 B Cecil Drive, Chester $634,595

Across the Street from the Water, One of our most popular designs, the Doral offers formal ( office space) and informal living areas with lots of room for the whole famil...

  • 4 Beds
  • 3 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

Harbor View Real Estate & Homes

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Harbor View, Chester MD. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

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Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

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