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6 Madison Pl Annapolis, MD 21401

2 bd
1 1/2 ba

155 King George St, Annapolis, MD 21401

1.5 ba
1350 Sq Ft

35 Carver Street #C Annapolis, MD 21401

1 bd
1 ba
600 Sq Ft

304 Burnside Street, Annapolis, MD 21403

3 bd
3 ba

63 East #1, Annapolis, MD 21401

1 bd
1 ba
600 Sqft

28 Lafayette Annapolis, MD 21041

2 bd
2 ba
1100

29 Carver St #B, Annapolis, MD 21401

2 bd
1 ba
900 Sqft

35 Carver Street #B Annapolis, MD 21401

1 bd
1 ba

35 Carver Street #D Annapolis, MD 21401

1 bd
1 ba

37 Madison Pl Apt 2, Annapolis, MD 21401

3 bd
2 ba
1150 Sqft

240 Ternwing Dr, Arnold, MD 21012

3 bd
2 ba

33 Carver Street #B Annapolis, MD 21401

2 bd
1 ba

31 Carver Street #A Annapolis, MD 21401

2 bd
1 ba

8 Madison Pl, Annapolis, MD 21401

2 bd
1 ba

31 Carver Street #B Annapolis, MD 21401

2 bd
1 ba

4 Madison Pl, Annapolis, MD 21401

2 bd
1 ba
1200 Sq Ft

112 S Villa Ave 1, Annapolis, MD 21401

2 bd
1 ba
625 Sq Ft

153 King George St, Annapolis, MD 21401

2 bd
1.5 ba
1350 Sq Ft

Our Perks

LIVE UNIQUELY

We offer a variety of renovated properties including one and two-bedroom apts, townhomes and single-family homes. Live with your pet or get one from the SPCA! Our properties are all historic and unique; there are no 'cookie-cutter' homes. Lives are not lived in one-year chapters; we offer varying term leases.

LIVE MODERN

Our historic renovated properties offer the latest amenities including USB enabled outlets, electronic locks, ductless HVAC and energy efficient appliances. Communicate with us on your terms through email and text. We accept electronic payments to reduce the hassle of checks and dealing with the post office.

LIVE INSPIRED

Surround yourself with inspiration as you wake up in sight of the Naval Academy, the State House and the Chesapeake Bay. For over twenty years, government and civilian professionals, naval officers, professors and academy professionals have relied on our flexible leasing process and responsive team.

Find Your Perfect Home

Chesapeake Properties provides quality and affordable properties on flexible terms to professionals, naval officers, pet lovers, DC/Baltimore commuters and Annapolis sailors. Most of our properties are located in the Historic District; only steps from the waterfront, restaurants and cafes. Our properties are all unique and each have their own story.

We are passionate about helping you find your idea Annapolis rental home. With over 20 years of real estate experience and as life-long Annapolitans, we are experts on this market. We are an independent company and not constrained by typical corporate regulations. We celebrate individuality; in ourselves and our properties.

Compare Listings

Find a Property

6 Madison Pl Annapolis, MD 21401

6 Madison Pl Annapolis, MD 21401

155 King George St, Annapolis, MD 21401

155 King George St, Annapolis, MD 21401

35 Carver Street #C Annapolis, MD 21401

35 Carver Street #C Annapolis, MD 21401

304 Burnside Street, Annapolis, MD 21403

304 Burnside Street, Annapolis, MD 21403

63 East #1, Annapolis, MD 21401

63 East #1, Annapolis, MD 21401

28 Lafayette Annapolis, MD 21041

28 Lafayette Annapolis, MD 21041

29 Carver St #B, Annapolis, MD 21401

29 Carver St #B, Annapolis, MD 21401

35 Carver Street #B Annapolis, MD 21401

35 Carver Street #B Annapolis, MD 21401

35 Carver Street #D Annapolis, MD 21401

35 Carver Street #D Annapolis, MD 21401

37 Madison Pl Apt 2, Annapolis, MD 21401

37 Madison Pl Apt 2, Annapolis, MD 21401

240 Ternwing Dr, Arnold, MD 21012

240 Ternwing Dr, Arnold, MD 21012

33 Carver Street #B Annapolis, MD 21401

33 Carver Street #B Annapolis, MD 21401

31 Carver Street #A Annapolis, MD 21401

31 Carver Street #A Annapolis, MD 21401

8 Madison Pl, Annapolis, MD 21401

8 Madison Pl, Annapolis, MD 21401

31 Carver Street #B Annapolis, MD 21401

31 Carver Street #B Annapolis, MD 21401

4 Madison Pl, Annapolis, MD 21401

4 Madison Pl, Annapolis, MD 21401

112 S Villa Ave 1, Annapolis, MD 21401

112 S Villa Ave 1, Annapolis, MD 21401

153 King George St, Annapolis, MD 21401

153 King George St, Annapolis, MD 21401

Our Perks

LIVE UNIQUELY

LIVE MODERN

LIVE INSPIRED

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