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"Chesapeake Properties from the beginning has treated us like friends. Always accessible via text or phone for any issues regardless how small, we don’t feel like just a number. We thoroughly enjoyed our apartment, its convenience, cleanliness and better than normal appliances and floors made me feel like I had a home, not just living somewhere to have something. We highly recommend Chesapeake if you are looking for something better than just temporary living space. They will do whatever they can to make you comfortable!!"

by Megan F. and Philip S.

"Working with Chesapeake properties has been a great experience during my time in Annapolis! With one of the few, newly renovated places in downtown Annapolis, I could not have found a better place to live. Rosie and her team have been extremely helpful and accommodating with all things relating to the apartment, and are always extremely quick to respond to my emails and texts. Thanks for everything— I have been very pleased with my time with Chesapeake!"

by Katherine L.

"The staff at Chesapeake Properties are amazing. They're quick to respond, helpful, and always friendly. They have such a high standard for their properties and customer interactions. I wouldn't hesitate to work with them again!"

by Chethan R.

From my first encounter of inquiring about the properties they had available all the way to moving in ... they have been wonderful, kind and personable. They genuinely care about their tenants. Another thing that I find impressive is they care about the neighbors and the neighborhood their properties are among. They know the people who have lived here for years and it was clear they went the extra mile to make sure they knew they mattered while getting my place remodeled. They are not just a Property manager, they are invested in the community and people... and they are dog friendly. Rosie and Michael and John have been so good to me, even gave me a couple of gift cards during the Coronavirus to support local business just for voting for my favorite breakfast place on their instagram! I am grateful to have this wonderful place and work with such a great group of people.

by Renee Farnie

Find a Property

6 Madison Pl Annapolis, MD 21401

2 bd
1 1/2 ba
1100 Sq Ft

26 Lafayette Ave B, Annapolis, MD 21401

2 bd
2.5 ba
1230 Sq Ft

155 King George St, Annapolis, MD 21401

2 bd
1.5 ba
1350 Sq Ft

112 South Villa Ave, Unit 4

2 bd
1 ba
625 Sq Ft.

112 South Villa Ave- Unit 2

2 bd
1 ba
625 Sq Ft

63 East St Unit 3

1 bd
1 ba
675 Sq Ft

29 Carver St. Unit C

2 bd
1 ba
900 Sq Ft

152 Main Unit 203

1 bd
1 ba
625 Sq Ft

152 Main St Unit 303

1 bd
1 ba
650 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 Sq Ft

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
575 Sq Ft.

37 Madison Pl Apt 2, Annapolis, MD 21401

3 bd
2 ba
1150 Sqft

240 Ternwing Dr, Arnold, MD 21012

3 bd
2 ba

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

"The staff at Chesapeake Properties are amazing. They're quick to respond, helpful, and always friendly. They have such a high standard for their properties and customer interactions. I wouldn't hesitate to work with them again!"

Find a Property

6 Madison Pl Annapolis, MD 21401

6 Madison Pl Annapolis, MD 21401

26 Lafayette Ave B, Annapolis, MD 21401

26 Lafayette Ave B, Annapolis, MD 21401

155 King George St, Annapolis, MD 21401

155 King George St, Annapolis, MD 21401

112 South Villa Ave, Unit 4

112 South Villa Ave, Unit 4

112 South Villa Ave- Unit 2

112 South Villa Ave- Unit 2

63 East St Unit 3

63 East St Unit 3

29 Carver St. Unit C

29 Carver St. Unit C

152 Main Unit 203

152 Main Unit 203

152 Main St Unit 303

152 Main St Unit 303

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

Our Perks

LIVE UNIQUELY

LIVE MODERN

LIVE INSPIRED

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