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200 Schooner Way, Chester image
200 Schooner Way, Chester $550,000

Just minutes over the Chesapeake Bay Bridge, this beautifully maintained end-unit townhome in Bayside offers the perfect Eastern Shore escape. Spectacular water views ove...

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

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

Selling Office: .

1012 Auckland Way, Chester image
1012 Auckland Way, Chester $599,900

Experience the best of Kent Island waterfront living in this beautifully appointed home located in the sought-after Bayside community of Chester. Designed for both everyd...

  • 3 Beds
  • 4 Baths
Courtesy of Redfin Corp

Listing courtesy of Redfin Corp. Contact: 3016586186

807 Auckland Way, Chester image
807 Auckland Way, Chester $425,500

Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier Bayside waterfront community. Comparable properties in this Chester River commun...

  • 3 Beds
  • 4 Baths
Courtesy of Real Broker, LLC - Chester

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

106 Bodys Neck Rd, Chester image
106 Bodys Neck Rd, Chester $435,000

Welcome to Bayside, where coastal living and resort-style amenities come together in one of the area’s most desirable waterfront communities. This 3-bedroom, 2.5-bath con...

  • 3 Beds
  • 3 Baths
Courtesy of Realty Navigator

Listing courtesy of Realty Navigator. Contact: 4106433404

501 Teal Court, Chester image
501 Teal Court, Chester $310,000

Welcome to easy, waterfront-inspired living in the heart of Chester! This beautifully maintained first-floor condo at 501 Teal Ct offers the perfect blend of comfort, sty...

  • 5 Beds
  • 4 Baths
Courtesy of Samson Properties

Listing courtesy of Samson Properties. Contact:

Selling Office: .

402 Blenny Lane, Chester image
402 Blenny Lane, Chester $365,000

End-unit three-level townhome overlooking the pond in Bayside community. Freshly painted, new LVP on lower level. Engineered wood floors on main level. Living room has pr...

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

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

Selling Office: .

306 Teal Court Unit #C, Chester image
306 Teal Court Unit #C, Chester $265,000

Beautifully maintained first-floor condominium featuring tranquil lake views and a bright, open floor plan designed for comfortable living and effortless entertaining. Th...

  • 2 Beds
  • 2 Baths
Courtesy of Kelly and Co Realty, LLC

Listing courtesy of Kelly and Co Realty, LLC. Contact:

Selling Office: .

206 Blenny Lane, Chester image
206 Blenny Lane, Chester $332,500

Positioned in the heart of Chester’s marina district and just a few blocks from Castle Marina, this 3-bedroom, 2 full/2 half bath townhome brings you close to both nature...

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

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: .

906 Auckland Way, Chester image
906 Auckland Way, Chester $490,000

This beautifully maintained 3-bedroom, 3.5-bath marina-front townhouse with a 1-car garage offers the perfect blend of comfort, convenience, and Chesapeake lifestyle. Ide...

  • 3 Beds
  • 4 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

108 Bodys Neck Road, Chester image
108 Bodys Neck Road, Chester $499,000

Experience Autumn Serenity on the Waterfront Discover the perfect blend of coastal charm and modern luxury this fall in this rarely available, oversized end-unit townho...

  • 3 Beds
  • 3 Baths
Courtesy of Realty Navigator

Listing courtesy of Realty Navigator. Contact:

Selling Office: .

104 Golden Eye Court, Chester image
104 Golden Eye Court, Chester $300,000

What sets this Bayside Marina condo apart? Let us start with the spectacular view, a peaceful pond and sparkling fountain right outside your windows. Picture perfect loc...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

112 Harbour Sound Drive, Chester image
112 Harbour Sound Drive, Chester $540,656

Resort Living at it's best!! Available furnished or unfurnished. Enjoy stunning, unobstructed water views in the highly sought after community of Bayside! Many recent up...

  • 2 Beds
  • 4 Baths
Courtesy of Annapolis Properties LLC

Listing courtesy of Annapolis Properties LLC. Contact:

Selling Office: .

208 Ringneck Court, Chester image
208 Ringneck Court, Chester $330,000

208 Ringneck Court is a great home for the smart buyer! The 2 bedroom, 2 1/2 bathroom GARAGE town-home, located in the Bayside community on the Chester River, underwe...

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

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

Selling Office: .

202 Ringneck Court, Chester image
202 Ringneck Court, Chester $335,000

PRICE IMPROVED.............Dont miss out, still time to enjoy summer near the water! Beautifully Updated End-Unit Townhouse in Sought-After Bayside Community! This spac...

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

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

211 Golden Eye Court, Chester image
211 Golden Eye Court, Chester $285,000

Discover this impeccably cared-for 2-bedroom, 2-bathroom condo, offering the ultimate in low-maintenance living within one of Kent Island’s most desirable neighborhoods. ...

  • 2 Beds
  • 2 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

513 Teal Court Unit #G, Chester image
513 Teal Court Unit #G, Chester $295,000

*Experience a getaway lifestyle at this stunning 2nd-floor condominium nestled within the prestigious Bayside Condominium Community. Enjoy peaceful views of the pond and ...

  • 2 Beds
  • 2 Baths
Courtesy of Rosendale Realty

Listing courtesy of Rosendale Realty. Contact:

Selling Office: .

204 Teal Court Unit #B, Chester image
204 Teal Court Unit #B, Chester — Bayside $295,000

Lakefront Condo in Premier Community! Don’t miss your chance to own this stunning ground-floor condo with serene lake views from every room—including the soothing sights...

  • 2 Beds
  • 2 Baths
Courtesy of NetRealtyNow.com, LLC

Listing courtesy of NetRealtyNow.com, LLC. Contact:

Selling Office: .

605 Teal Court, Chester image
605 Teal Court, Chester $300,000

Welcome to 605 Teal Court! A beautifully maintained 2-bedroom, 2-bathroom condo offering easy, low-maintenance living in one of Kent Island’s most desirable communities. ...

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

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

208 Merganser Court, Chester image
208 Merganser Court, Chester $290,000

Beautiful and hard to find 2BR, 2BA walk-in end unit on the lake in the Bayside community by Four Seasons; unit has wide open views from its lakeside patio, community poo...

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

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

Selling Office: .

307 Schooner Way Unit #42, Chester image
307 Schooner Way Unit #42, Chester $364,900

Nestled in the heart of the Bayside Community overlooking the pond, this immaculate 2 ( possibly 3) bedroom, 2.5-bathroom end unit townhome beautifully combines elegance ...

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

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

Selling Office: .

300 Drake Tail Place, Chester image
300 Drake Tail Place, Chester $305,000

Just reduced $10000 on 10/9/24 Well- Maintained END UNIT CHESTER RIVER TOWNHOME in AMENITY RICH BAYSIDE with Clubhouse offering party/exercise rooms, outdoor pool & loung...

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

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

Selling Office: .

601 Teal Court, Chester image
601 Teal Court, Chester $285,000

Ground Level End Unit Condo with Modern Features and Prime Location! Discover easy living in this spacious 2-bedroom, 2-bath condo located on the ground level with a pri...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

104 Golden Eye Court, Chester image
104 Golden Eye Court, Chester $285,000

The best water views fill this condo *You are going to love calling this haven home* Enjoy 1 level living here* Much desired 1st floor unit* Provides 2 bedrooms an...

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

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

Selling Office: .

312 Widgeon Way, Chester image
312 Widgeon Way, Chester $375,000

Second Chances are a really big deal! Don't miss this stunning end unit in the the amenity rich Bayside Community which includes a large clubhouse with year-round enterta...

  • 3 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: .

607 Teal Court, Chester image
607 Teal Court, Chester $292,000

Open House Canceled - Under Contract! This 2 Bedroom, 2 full Bath Ground Level End Unit with POND VIEW is absolutely turn key with fresh paint, NEW carpet and flooring +...

  • 2 Beds
  • 2 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

1006 Auckland Way, Chester image
1006 Auckland Way, Chester $590,000

**Wonderful Waterfront Town Home w/out the High Taxes**Three Full Levels of Living on the Chester River!**Open Lower Level has the Living Room Facing the Water**Updated K...

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

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

Selling Office: .

1014 Auckland Way, Chester image
1014 Auckland Way, Chester $587,500

Rarely available Villa at the end of Auckland Way with full water view (NOT marina view) from every level. Welcome to resort style living right at the water’s edge. Catc...

  • 3 Beds
  • 4 Baths
Courtesy of Monument Sotheby's International Realty

Listing courtesy of Monument Sotheby's International Realty. Contact:

Selling Office: .

305 Schooner Way Unit #43, Chester image
305 Schooner Way Unit #43, Chester — Bayside $345,900

Welcome to Bayside luxury living at its finest! This stunning three-bedroom townhome offers the perfect blend of elegance and convenience. Inside, you'll find a spacious...

  • 3 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

306 Drake Tail Place, Chester image
306 Drake Tail Place, Chester $330,000

Welcome to 306 Drake Tail Place! This charming 3-bedroom, 2.5-bathroom end unit townhome offers a comfortable and inviting living space spanning 1440 square feet. Upon en...

  • 3 Beds
  • 3 Baths
Courtesy of Compass

Listing courtesy of Compass. Contact:

Selling Office: .

206 Widgeon Way, Chester image
206 Widgeon Way, Chester — Bayside Condo North $505,900

Gorgeous Marina View Townhome backing to Castle Harbour Marina with stunning nautical views from your Living Room, Deck, Primary Bedroom and Balcony! This well maintained...

  • 3 Beds
  • 4 Baths
Courtesy of RE/MAX Leading Edge

Listing courtesy of RE/MAX Leading Edge. Contact:

Selling Office: .

102 Ringneck Court, Chester image
102 Ringneck Court, Chester $369,999

Welcome to this stunning 3-bedroom, 2.5-bathroom townhouse offering luxurious living across three levels. Step inside to find gleaming hardwood floors that flow seamlessl...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

218 Blenny Lane, Chester image
218 Blenny Lane, Chester $390,000

Back on This perfect gem of a Townhome has everything you’re looking for…. and so much more! Enjoy a morning cup of coffee on the spacious deck looking at the pond and ...

  • 4 Beds
  • 4 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

202 Merganser Court, Chester image
202 Merganser Court, Chester $290,000

202 Merganser Ct, Bayside Condos is a ground floor end unit on the lake, with 2 bedrooms, 2 full baths with walk-in shower in master bath. High end finishes include elec...

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

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

Selling Office: .

405 Widgeon Way, Chester image
405 Widgeon Way, Chester — Bayside Condo North $475,000

Kent Island Waterfront Townhome with Garage - Gorgeous Water View * Marina View * Beautiful Bayside Townhouse with 2100 sf backing to Castle Harbour Marina* 2 Bedrooms +...

  • 2 Beds
  • 4 Baths
Courtesy of RE/MAX Leading Edge

Listing courtesy of RE/MAX Leading Edge. Contact:

Selling Office: .

308 Blenny Lane, Chester image
308 Blenny Lane, Chester $365,000

Welcome to Eastern Shore Living on Kent Island! This stunning Townhome nestled in the heart of the desired Waterfront Community of Bayside is sure to please! Pure enjoyme...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

509 Teal Court Unit #E, Chester image
509 Teal Court Unit #E, Chester $270,000

Price Improvement a great value on this lovely well-maintained 2-bedroom, 2-bathroom end unit with a view of the pond and marina. The open floor plan, cathedral ceiling i...

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

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

413 Merganser Court, Chester image
413 Merganser Court, Chester $270,000

Top floor-Lovely Open Concept condo with 2 bedrooms 2 full baths, Hardwood floors, balcony overlooking community area all in the Bayside Community with club house, gym,...

  • 2 Beds
  • 2 Baths
Courtesy of Maryland Residential Management Co

Listing courtesy of Maryland Residential Management Co. Contact:

Selling Office: .

314 Merganser Court, Chester image
314 Merganser Court, Chester $265,000

You are going to love the water views from this coastal cottage condo in Bayside. Filled with light and architecturally pleasing, this home provides an open floor plan w...

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

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

Selling Office: .

915 Auckland Way, Chester image
915 Auckland Way, Chester $427,000

Welcome to Eastern Shore living at Bayside! This meticulously cared for three level water-view townhome overlooks Northeast Bay and the Chester River. Amazing open-conc...

  • 3 Beds
  • 4 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

910 Auckland Way, Chester image
910 Auckland Way, Chester $560,000

Welcome to this exquisite, fully furnished Bayside Villa with direct views of Castle Marina. Almost every room in this home offers breathtaking view of the Chester River,...

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

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

Selling Office: .

409 Merganser Court Unit #E, Chester image
409 Merganser Court Unit #E, Chester — Bayside Marina $285,000

Gorgeous 2 Bedroom, 2 Full Bathroom, End unit condo in highly desired Bayside Marina! This unit boasts hardwood floors, new carpet, paint, new ceiling fans and light fix...

  • 2 Beds
  • 2 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

510 Auckland Way, Chester image
510 Auckland Way, Chester $385,900

Gorgeous End Unit in BAYSIDE! OPEN HOUSE Saturday July 29, Saturday from 10am-1pm AND July 30 Sunday, 12-2pm! SPACIOUS End Unit facing a row of trees and nestled back in ...

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

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

605 Blenny Lane, Chester image
605 Blenny Lane, Chester $480,000

This is the one with Marina & Chester River Views! Over 2,000 sq ft of living space awaits you in this meticulously cared for Bayside Villa with Garage! You'll love the t...

  • 3 Beds
  • 4 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

905 Auckland Way, Chester image
905 Auckland Way, Chester $426,500

***Seller will pay 1 year of HOA dues for acceptable offer***Bayside Oasis! Enjoy relaxed gatherings, entertaining and views of the Chester River in this Established and ...

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

Listing courtesy of Chaney Homes, LLC. Contact:

Selling Office: .

501 Teal Court, Chester image
501 Teal Court, Chester $290,000

This practically perfect main level Bayside 2 BR/2BA condo is the perfect spot for those who don't wish to climb stairs to come and go! There is a lovely water feature to...

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

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: .

Bayside Real Estate & Homes

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Bayside, 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. 

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