Browse All Chester MD 2 Bedroom Properties for Sale

Welcome to easy, low-maintenance living in the sought-after Bayside community of Chester! This beautifully maintained 2-bedroom, 2-bathroom condo offers the perfect combi...

2 Beds
2 Baths

Courtesy of The KW Collective

Listing courtesy of The KW Collective. Contact:

1 Queen Victoria Ct, Chester $400,000

Shore living doesn’t get much better than this! Wake up in this waterfront community perfectly tucked along the Chester River in the vibrant community of Queens Landing. ...

2 Beds
2 Baths

Courtesy of Douglas Realty LLC

Listing courtesy of Douglas Realty LLC. Contact:

830 Warbler Way Unit 2843, Chester image

830 Warbler Way Unit 2843, Chester $789,990

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home combines modern comfort with functional and stylish liv...

2 Beds
3 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

111 Marshgrass Way Unit 43, Chester image

111 Marshgrass Way Unit 43, Chester $744,900

Every season brings a new perspective from this exceptional top-floor penthouse at Four Seasons at Kent Island. Set within one of the Eastern Shore’s premier 55+ communit...

2 Beds
3 Baths

Courtesy of Long & Foster Real Estate, Inc.

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

34 Queen Anne Way Unit A, Chester $570,000

The view is the main event. Homes throughout Queens Landing sit at varying distances from the waterfront, and it is hard to get closer than this. Positioned directly alon...

2 Beds
2 Baths

Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact:

168 Redstart Dr, Chester $749,900 ▼

NEW PRICE! Reduced! Gorgeous All On One Level Home in Premiere 55+ Community of Four Seasons @ Kent Island * Offering This Lovely Taylor Model w 2/3 Bedrooms + 2.5 Baths...

2 Beds
3 Baths

Courtesy of RE/MAX Leading Edge

Listing courtesy of RE/MAX Leading Edge. Contact:

129 Wheelhouse Way Unit 11, Chester image

129 Wheelhouse Way Unit 11, Chester $585,000

Priced well below market value! The builder can not compete with this price. Welcome to one of the most desirable locations in Four Seasons at Kent Island, where luxury,...

2 Beds
3 Baths

Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact:

7 Queen Victoria Way Unit B, Chester image

7 Queen Victoria Way Unit B, Chester — Queens Landing $499,000

Welcome to 7B Queen Victoria Way at Queen’s Landing, a beautifully renovated waterfront residence w/ spectacular views of the marina basin, marina fairway, and Chester Ri...

2 Beds
3 Baths

Courtesy of RE/MAX Allegiance

Listing courtesy of RE/MAX Allegiance. Contact:

630 Warbler Way Unit 12, Chester $549,950

Experience everything Four Seasons at Kent Island has to offer without the wait! Less than one year old, this beautifully maintained home shows like new and offers one of...

2 Beds
3 Baths

Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact:

118 Kinglet Ct, Chester $969,990

Welcome to the Taylor, a beautifully designed home offering 2 bedrooms, 2 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for ...

2 Beds
3 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

830 Warbler Way Unit 2833, Chester image

830 Warbler Way Unit 2833, Chester $689,990

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home combines modern comfort with functional and stylish liv...

2 Beds
3 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

228 Bayberry Dr, Chester $665,000

Immediate Occupancy-Be HOME for the HOLIDAYS! Built in 2019, this coastal style cutie is BETTER than new & offers a bright open layout that includes 2 SPACIOUS BEDROOMS c...

2 Beds
3 Baths

Courtesy of Long & Foster Real Estate, Inc.

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

15 Qun Ann Way Unit E, Chester $529,000 ▼

Located in the beautiful Queens Landing community, this Spanish-style waterfront townhouse offers a luxurious lifestyle with stunning river views. The interior boasts an ...

2 Beds
3 Baths

Courtesy of Benson & Mangold, LLC

Listing courtesy of Benson & Mangold, LLC. Contact:

53 Queen Caroline Ct, Chester $329,000

Nestled in the community of Queens Landing, this townhome offers a blend of coastal charm and contemporary elegance with carefree living. Boat slips with provisioned boat...

2 Beds
3 Baths

Courtesy of EXP Realty, LLC

Listing courtesy of EXP Realty, LLC. Contact:

641 Warbler Way, Chester $599,990 ▼

Welcome to the Bernstein II, a beautifully designed home offering 2 bedrooms, 2 baths, and a 2-car garage. This home combines an open-concept layout with thoughtful desig...

2 Beds
2 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

200 Church St, Chester $350,000

Your Island Getaway Is Waiting! Dreaming of a cozy home where life feels a little more relaxed and every season brings something to look forward to? This charming 2/3-bed...

2 Beds
2 Baths

Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact:

736 Warbler Way Unit 2733, Chester image

736 Warbler Way Unit 2733, Chester $719,990

Welcome to Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in May 2027, this home combines comfort, fun...

2 Beds
3 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

110 Boatswain Way Unit 3012, Chester image

110 Boatswain Way Unit 3012, Chester $619,990 ▼

Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home blends modern ...

2 Beds
3 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

118 Broadwater Dr, Chester $645,000 ▼

Welcome to Resort-Style Living at Four Seasons at Kent Island! Why wait for new construction when you can move right into this beautifully upgraded Donegal model with th...

2 Beds
2 Baths

Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact:

102 Boatswain Way Unit 2912, Chester image

102 Boatswain Way Unit 2912, Chester $609,990

Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. T...

2 Beds
3 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

102 Boatswain Way Unit 2943, Chester image

102 Boatswain Way Unit 2943, Chester $909,990 ▼

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines mod...

2 Beds
3 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

102 Boatswain Way Unit 2932, Chester image

102 Boatswain Way Unit 2932, Chester $809,990 ▼

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines mod...

2 Beds
3 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

102 Boatswain Way Unit 2911, Chester image

102 Boatswain Way Unit 2911, Chester $619,990 ▼

Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. T...

2 Beds
3 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

102 Boatswain Way Unit 2933, Chester image

102 Boatswain Way Unit 2933, Chester $809,990 ▼

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines mod...

2 Beds
3 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

110 Boatswain Way Unit 3042, Chester image

110 Boatswain Way Unit 3042, Chester $699,990 ▼

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines mode...

2 Beds
3 Baths

Courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

121 Merlin Dr, Chester $697,900 ▼

Assumable VA Loan available w/interest rate in 5's to qualified buyers! Experience the ease of elegant one-level living in this exceptional home, located in one of Maryla...

2 Beds
2 Baths

Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

230 Switchgrass Way Unit 12, Chester image

230 Switchgrass Way Unit 12, Chester $499,000 ▼

NEW PRICE —PRICED TO SELL! Motivated Sellers, move-in ready, and available for a quick settlement on your timeline. Move-in ready condo with zero wait! This meticulously ...

2 Beds
3 Baths

Courtesy of Real Broker, LLC - Chester

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

1000 Herons Nest Way Unit 43, Chester image

1000 Herons Nest Way Unit 43, Chester $595,000 ▼

Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun ...

2 Beds
3 Baths

Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

132 Wheelhouse Way Unit 11, Chester image

132 Wheelhouse Way Unit 11, Chester $699,000 ▼

Priced to sell at just $700,000, this is an exceptional opportunity. With a $160,000 lot premium and over $60,000 in builder upgrades, this home is offered below its repl...

2 Beds
3 Baths

Courtesy of Real Broker, LLC

Listing courtesy of Real Broker, LLC. Contact:

45 Queen Neva Ct, Chester $318,500 ▼

Price Improvement! Seller is offering closing cost assistance for qualified buyers! This charming townhouse in Queens Landing offers a perfect blend of comfort and commun...

2 Beds
3 Baths

Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

1000 Herons Nest Way Unit 22, Chester image

1000 Herons Nest Way Unit 22, Chester — Chester $485,000 ▼

BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wil...

2 Beds
3 Baths

Courtesy of RE/MAX Executive

Listing courtesy of RE/MAX Executive. Contact:

102 Boatswain Way Unit 2912, Chester $599,990 ▼

Welcome to the Magothy, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines mod...

2 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

110 Boatswain Way Unit 3043, Chester image

110 Boatswain Way Unit 3043, Chester $799,990 ▼

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines mode...

2 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

110 Boatswain Way Unit 3033, Chester image

110 Boatswain Way Unit 3033, Chester $699,990 ▼

The Chester offers a thoughtfully designed open floorplan with a projected settlement date of October 2026. Ideal for modern living, this home features 2 bedrooms, 2.5 ba...

2 Beds
3 Baths

Courtesy of KOVO Realty

Listing courtesy of KOVO Realty. Contact:

4000 Herons Nest Way Unit 22, Chester image

4000 Herons Nest Way Unit 22, Chester $492,500 ▼

Four Seasons @ Kent Island - 55+ Community - Reduced! * Turn-key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, S...

2 Beds
3 Baths

Courtesy of RE/MAX Leading Edge

Listing courtesy of RE/MAX Leading Edge. Contact:

3000 Herons Nest Way Unit 11, Chester image

3000 Herons Nest Way Unit 11, Chester $460,000 ▼

This highly sought-after first-floor condo offers the opportunity to own a fully upgraded 2,003 square foot Four Seasons Condo without waiting for new construction. Just...

2 Beds
3 Baths

Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

1405 Little Creek Rd, Chester $19,500

This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities f...

2 Beds
1 Baths

Courtesy of The Parker Group

Listing courtesy of The Parker Group. Contact:

505 Swan Cove Ln, Chester $600,000

Nestled along the serene shores of the Chester River, 505 Swan Cove Ln presents an exquisite west facing waterfront retreat offering the perfect blend of elegance, comf...

2 Beds
2 Baths

Courtesy of EXIT On The Bay

Listing courtesy of EXIT On The Bay. Contact:

2 Bedroom Chester Real Estate

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