Annapolis Homes under $500,000

Welcome to Annapolis, Maryland—a charming city steeped in history, vibrant culture, and picturesque waterfront views. As the capital of Maryland and home to the United States Naval Academy, Annapolis boasts a rich maritime heritage that captivates both residents and visitors alike. Nestled along the scenic Chesapeake Bay, this city offers a unique blend of small-town charm and urban sophistication, making it an ideal destination for families, professionals, and retirees.

Annapolis is known for its stunning colonial architecture, with historic buildings lining the cobblestone streets of the downtown area. Enjoy leisurely strolls along the waterfront, where you can indulge in fresh seafood at local eateries, explore boutique shops, or take in the sights of sailboats gliding across the bay. The city is also home to numerous parks and recreational areas, providing ample opportunities for outdoor activities.

For those looking to make Annapolis their home, you'll be pleased to discover a variety of charming properties available under $500,000. From cozy townhomes to quaint single-family houses, there are options to suit diverse lifestyles and preferences. Living in Annapolis means embracing a vibrant community with access to top-rated schools, cultural events, and a strong sense of belonging.

Whether you’re drawn by the historical significance, the stunning waterfront, or the welcoming atmosphere, Annapolis is a place where you can truly thrive. Explore your opportunities in this beautiful city today and find your perfect home in a community that feels like a warm embrace.

Newest Annapolis Homes under $500,000

801 Midship Ct, Annapolis $500,000

Welcome to 801 Midship Court, a refreshed end unit townhouse offering 1,514 square feet of comfortable single level living in the established 55 plus community of Heritag...

2 Beds
2 Baths

Courtesy of Next Step Realty, LLC.

Listing courtesy of Next Step Realty, LLC.. Contact:

940 Astern Way Unit 304, Annapolis image

940 Astern Way Unit 304, Annapolis — The Reserve $484,900

BACK ON THE MARKET — YOUR SECOND CHANCE IS HERE! If you were disappointed when you missed this home the first time around, you’re in luck! The current owners’ plans have ...

2 Beds
2 Baths

Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact:

3458 Newport Ave, Annapolis $489,909

Welcome to this beautifully renovated 3-bedroom, 2-full-bath single-family home in the desirable Arundel on the Bay community. This move-in-ready home features a spacious...

3 Beds
2 Baths

Courtesy of RE/MAX Galaxy

Listing courtesy of RE/MAX Galaxy. Contact:

2711 Summerview Way Unit 203, Annapolis image

2711 Summerview Way Unit 203, Annapolis $385,000

Beautiful 2-Bed, 2-Bath Condo with Water Access in Annapolis! Welcome home to this beautifully updated 2-bedroom, 2-bathroom condo in the sought-after Riva Trace! Step i...

2 Beds
2 Baths

Courtesy of Monument Sotheby's International Realty

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

1045 Cedar Ridge Ct, Annapolis $399,900

COMPLETELY RENOVATED & MOVE-IN READY IN CEDAR RIDGE! After 30 years of thoughtful ownership and meticulous care, this beautifully updated 3-bedroom, 2½-bath townhouse is ...

3 Beds
3 Baths

Courtesy of Academy Realty Inc.

Listing courtesy of Academy Realty Inc.. Contact:

71 Harbour Hts Unit 71, Annapolis $399,000

Welcome to 71 Harbour Heights Drive, a well-appointed 3-bedroom, 2.5-bath home offering comfortable living in an incredibly convenient Annapolis location. The eat-in kitc...

3 Beds
3 Baths

Courtesy of Engel & Volkers Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

30 Hearthstone Ct Unit G, Annapolis image

30 Hearthstone Ct Unit G, Annapolis $299,000

Welcome home to this beautiful 2-bedroom, 2-bath home—the largest model in Annapolis Overlook! This bright spacious residence features an open concept layout, high ceilin...

2 Beds
2 Baths

Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

982 Riversedge Cir, Annapolis $429,900

Welcome to easy living in Annapolis’ desirable Heritage Harbour 55+ community. This charming two-bedroom, two-bath villa is ideally situated just a short walk from the co...

2 Beds
2 Baths

Courtesy of TCB Realtor, LLC.

Listing courtesy of TCB Realtor, LLC.. Contact:

2522 N Haven Cove Cv N, Annapolis — Heritage Harbour $500,000

Welcome to refined, effortless living at 2522 N Haven Cove, nestled within the sought-after 55+ community of Heritage Harbour in Annapolis. This beautifully maintained 2-...

2 Beds
2 Baths

Courtesy of Taylor Properties

Listing courtesy of Taylor Properties. Contact:

755 Fairview Ave Unit 755 D, Annapolis image

755 Fairview Ave Unit 755 D, Annapolis — Severn House Condo $499,995

HUGE PRICE REDUCTION $25,000.00 Welcome Home! Don't let summer slip away before you have the chance to relax by this beautiful pool while enjoying one of the best waterfr...

3 Beds
2 Baths

Courtesy of RE/MAX Leading Edge

Listing courtesy of RE/MAX Leading Edge. Contact:

40 Ironstone Ct Unit B, Annapolis — Annapolis Overlook $335,000

Nestled in the charming and convenient Annapolis Overlook community, this inviting townhouse offers a perfect blend of comfort and investment potential. This traditional-...

3 Beds
3 Baths

Courtesy of RE/MAX One

Listing courtesy of RE/MAX One. Contact:

78 Old Mill Bottom Rd N Unit 209, Annapolis image

78 Old Mill Bottom Rd N Unit 209, Annapolis — None Available $424,800 ▼

Two years young, 55+ elevator condominium community enjoy this beautifully upgraded 2-bedroom + den residence with a balcony. Priced just shy at $113K less than current b...

2 Beds
2 Baths

Courtesy of Cottage Street Realty LLC

Listing courtesy of Cottage Street Realty LLC. Contact: