One of the most popular communities provided by {{page_data.agentName}}

Annapolis

One of the most popular communities provided by Maryland Sandbox

Annapolis

About Annapolis

Nestled on the shores of the Chesapeake Bay, Annapolis, Maryland, is a charming and historic community that seamlessly blends waterfront beauty with rich maritime heritage. As the state capital and home to the United States Naval Academy, Annapolis boasts a vibrant downtown area filled with unique shops, gourmet restaurants, and stunning colonial architecture. Residents and visitors alike can enjoy picturesque strolls along the scenic harbor, where sailboats and yachts bob in the water. With its engaging cultural scene, including art galleries, theaters, and annual festivals, Annapolis offers a lively atmosphere for all ages. The community takes pride in its top-rated schools, making it an ideal place for families. Outdoor enthusiasts can explore numerous parks, nature trails, and waterfront activities, while history buffs can immerse themselves in the city's storied past at landmarks such as the Maryland State House. Whether you're seeking a lively urban environment or a peaceful retreat by the bay, Annapolis is a vibrant community that truly has something for everyone.
One of the most popular communities provided by Maryland Sandbox
274
# of Listings
3
Avg # of Bedrooms
$510
Avg. $ / Sq.Ft.
$1,357,507
Med. List Price

Browse Annapolis Real Estate Listings

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Under $250,000

$250,000 - $500,000

$500,000 - $1M

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$3M - $5M

Over $5M

54 Properties Found. Page 1 of 4.

45 Randall Street is the kind of opportunity that almost never comes available in Downtown Annapolis—a charming boutique storefront positioned directly in the heartbeat of one of Maryland’s most visited waterfront destinations. Perfectly situated between the U.S. Naval Academy and the Annapolis waterfront, this high-visibility commercial property captures constant pedestrian traffic from tourists, locals, midshipmen, and boaters alike. The building’s prominent street presence and classic downtown character create the ideal setting for a boutique retail concept, coffee bar, specialty shop, studio, or investment hold in an irreplaceable location. Surrounded by established national and local retailers, restaurants, and year-round activity, this property offers the rare chance to own a piece of Randall Street in the center of Annapolis’ thriving historic district. Seller financing may be available.
#MDAA2145716

ANNAPOLIS

45 RANDALL STREET

None Beds

None Baths

240 Sq.Ft.

$500,000

MLS#: MDAA2145716

The Seasons change the views. Tremendous price reduction. A great opportunity just before the summer. Quiet tranquil setting for this 2 bedroom 2 bath unit with a view of the Bay in the distance, Windows in second bedroom replaced in 2024. To be sold in As-is condition. Enjoy the community amenities - 24 hour security, swimming pools, tennis courts, a beach and walking trails. Bay Ridge Rd. to Route 50 and 97 to DC and Baltimore. Easy to show, just call Showings to log in.
#MDAA2127108

ANNAPOLIS

2010 QUAY VILLAGE COURT 101

2 Beds

2 Baths

1,280 Sq.Ft.

$500,000

MLS#: MDAA2127108

New Price. Welcome Home!!! Beautiful Single Family Home, a peaceful retreat nestled in the water-privileged community of Oyster Harbor. Updates include all new oak hardwood flooring, custom kitchen cabinets with island and lots of counter space, quartz countertops and stainless steel appliances, sun filled living room, dining room, upscale bathrooms w/ custom tile and vanities, large bedrooms, private primary bedroom with full bathroom, screened in porch/sunroom, open floor plan with lots of windows and natural light, large driveway for lots of parking, font and side porches, fenced-in yard, brand new hvac and expansion tank, etc. Owner/Agent. Situated on the picturesque Annapolis Neck peninsula just minutes from downtown Annapolis by boat or car, Oyster Harbor is a private, water-privileged community offering an extraordinary waterfront lifestyle. Residents enjoy access to 3 bodies of water—Oyster Creek, Fishing Creek, and the Chesapeake Bay—along with three marinas, a boat ramp, fishing pier, and views that span from the Chesapeake Bay Bridge to the Thomas Point Shoal Lighthouse and beyond. The community also features two playgrounds, and a welcoming sandy beach. Ideally located close to the community beach, fishing pier, marina, and playground—and with easy access to Routes 50 and 97—this move-in-ready home combines coastal charm, neighborhood warmth, and unmatched convenience. Don’t miss this chance to make your private Annapolis oasis your own—it won’t last long!
#MDAA2130140

ANNAPOLIS

3365 ARUNDEL ON THE BAY ROAD

3 Beds

2 Baths

1,232 Sq.Ft.

$499,999

MLS#: MDAA2130140

Welcome to brand-new luxury living at Element at Mill Creek, a new construction community of modern condominiums designed for style, comfort, and convenience. This spacious, light-filled home offers southern exposure and a private balcony with serene views of lush forest retention—perfect for relaxing or entertaining. Inside, enjoy a chef-inspired kitchen with quartz countertops, upgraded cabinetry, stainless steel appliances, and a large center island. The open-concept living and dining areas create a warm, inviting atmosphere ideal for gatherings or quiet evenings. The primary suite features a generous walk-in closet and a spa-style bath with high-end finishes. Additional features include a full-size washer and dryer, included window treatments, ample storage, and reserved parking. As part of the new Element at Mill Creek community, you’ll enjoy low condo fees, resort-style amenities, and the ease of low-maintenance living in a brand-new home. Inquire today about available floor plans and pricing—your perfect new home is waiting!
#MDAA2134478

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 307

2 Beds

2 Baths

1,318 Sq.Ft.

$499,900

MLS#: MDAA2134478

Downtown living at its finest! A Naval Academy family dream location! An open layout combines living and dining areas with a modern kitchen, creating a comfortable, functional main living space that’s ideal for everyday living and easy entertaining. Beautiful hardwood floors, stainless steel appliances, in-unit laundry, and plenty of storage enhance the interior, while large windows bring in abundant natural light, making the space feel bright and inviting. An open layout combines living and dining areas with a modern kitchen, creating a comfortable, functional main living space that’s ideal for everyday living and easy entertaining. Beautiful hardwood floors, stainless steel appliances, in-unit laundry, and plenty of storage enhance the interior, while large windows bring in abundant natural light, making the space feel bright and inviting. Residence at Park Place is near all that Annapolis has to offer. An easy walk to restaurants, city dock, Naval Academy, Main Street, year-round waterfront events, and shopping! Your commute just got easier with direct access to Routes 50/97, Baltimore & BWI airport, Fort Meade, and the Eastern Shore! Come see your new home! (furniture negotiable)
#MDAA2140048

ANNAPOLIS

5 PARK PLACE 725

1 Beds

1 Baths

792 Sq.Ft.

$499,000

MLS#: MDAA2140048

Welcome to this lovely 2-bedroom, 1-bathroom home in the heart of Annapolis, offering classic charm and modern updates throughout. Featuring beautiful hardwood floors and a traditional layout, this home provides comfort and functionality in every room. The updated kitchen boasts a center island, granite and a spacious pantry all perfect for meal prep or casual dining. The bathroom has been tastefully renovated and includes a tub/shower combo. The newly-carpeted basement offers flexible space for a home office, gym or recreation area plus dual closets for extra storage. Utilize the savings and comfort from the high-efficiency zoned dual heating/cooling system and heat pump. Outside, enjoy the fully-fenced backyard with vinyl privacy fencing and a hardscaped patio-ideal for entertaining-and a custom 16 x 12 storage shed for tools and gear. Nature & water lovers will appreciate the home's close proximity to Quiet Waters Park, where you can enjoy walking trails, a dock and boat/kayak access to scenic Back Creek. You're also just minutes from the Severn River, the Annapolis Maritime Museum, downtown Annapolis, the Eastern Shore and major commuter routes to Washington D.C., Baltimore and beyond. Don't miss this perfect blend of location, charm and convenience-your Annapolis lifestyle awaits!
#MDAA2130832

ANNAPOLIS

1005 HYDE PARK DRIVE

2 Beds

1 Baths

1,190 Sq.Ft.

$489,000

MLS#: MDAA2130832

Brand New Carpet and wallpaper in bathrooms removed! ALSO, did you know, that one of the benefits of this home is that you CAN join and enjoy the Heritage Harbour amenities, BUT don't have to follow their 55+ rules at your home? This means if you can have adult children or grandchildren under the age of 55, they can stay with you as long as you would like! BEST OF BOTH WORLD!! Tucked away at the end of a quiet cul-de-sac, this two-level home has been lovingly cared for, is surrounded by mature trees and lush landscaping. Inside, the updated main level features durable and stylish LVP flooring, and it's truly move-in ready. The kitchen, remodeled in 2015, includes Corian countertops, a tile backsplash, updated cabinets, a stainless steel sink, and a garbage disposal, creating a functional and inviting space. With no age restrictions and an optional HOA( $97.60 monthly) offering access to a clubhouse, golf course, and more, this home provides flexibility and a lifestyle to fit a variety of needs. Don’t miss this well-maintained gem!
#MDAA2135788

ANNAPOLIS

2568 GLEN COVE

3 Beds

2 Baths

1,512 Sq.Ft.

$485,000

MLS#: MDAA2135788

Perched on the top floor of The Tecumseh, Maryland’s first condominium building, this two-level loft offers beautiful water views and an exceptional Eastport lifestyle. W401 overlooks Spa Creek with views of Ego Alley, the community marina, and Severn Avenue. This 1-bedroom, 1-bath residence features an open-concept main level with living and dining areas, a well-equipped kitchen, mechanical room, and storage closet. The loft-style upper level showcases exposed beams, soaring ceilings, abundant natural light, and a spacious bedroom with two closets and a full bath. Recent updates include fresh paint, new carpet and bathroom flooring (2024), refrigerator (2022), HVAC (2018), and dishwasher (2017). A rare bonus: boat slip entitlement in the private marina. Community amenities include gated parking, waterfront pool and deck, private marina, kayak and bike storage, secure entry with elevator, on-site management, and laundry on each upper floor. Located in the heart of Eastport, just steps to restaurants, shops, and downtown Annapolis by foot, bike, or water taxi. This is your opportunity to own in one of Eastport’s most sought-after waterfront communities - schedule a showing today. (The Tecumseh Condominium has a 15-day first right of refusal.)
#MDAA2137140

ANNAPOLIS

312 SEVERN AVENUE W 401

1 Beds

1 Baths

660 Sq.Ft.

$485,000

MLS#: MDAA2137140

Resort-Style Living in Heritage Harbour | Premier 55+ Community in Annapolis. Welcome to easy living in the sought-after Heritage Harbour active adult community! This beautifully updated ranch-style townhome offers more than just a home—it’s a lifestyle. Step onto the inviting front porch and into a bright, open floor plan featuring a spacious living room, dining area, and a remodeled kitchen with new cabinetry, countertops, and flooring—perfect for both everyday living and entertaining. The large primary suite includes a walk-in closet and a private en-suite bath, while the second bedroom offers direct access to a generous rear deck—ideal for relaxing or enjoying the outdoors. New carpeting adds comfort to both bedrooms. Additional highlights include a one-car attached garage and low-maintenance living in a vibrant, amenity-rich community. Enjoy all that Heritage Harbour has to offer—golf, indoor/outdoor pools, tennis, clubhouse activities, and lots more—just minutes from downtown Annapolis! Close to Restaurants, Shopping and more
#MDAA2143144

ANNAPOLIS

2627 COMPASS DRIVE

2 Beds

2 Baths

1,234 Sq.Ft.

$484,900

MLS#: MDAA2143144

Welcome to this beautifully updated home in the heart of Annapolis offering incredible flexibility, space, and opportunity! Situated on almost half an acre, this property features 5 bedrooms, 2 full bathrooms, two full kitchens, and a fully finished walk-out basement — perfect for multi-generational living, extended guests, rental potential, or anyone needing extra space. Seller financing may also be available, creating an exciting opportunity for qualified buyers. The main level showcases gorgeous hardwood floors, a bright and spacious living room with a cozy fireplace, and a renovated kitchen complete with white cabinetry, subway tile backsplash, quartz countertops. The updated bathroom features modern finishes and stylish tile work throughout. The fully finished walk-out basement adds even more living space with its own kitchen, full bathroom, laundry area, and multiple rooms that can be used as bedrooms, office space, gym, or guest quarters. Enjoy natural light throughout, generous-sized rooms, and a layout that offers endless possibilities. Conveniently located near downtown Annapolis, shopping, dining, commuter routes, and the Naval Academy.
#MDAA2140188

ANNAPOLIS

20 WASHINGTON DRIVE

5 Beds

2 Baths

1,828 Sq.Ft.

$480,000

MLS#: MDAA2140188

Exceptionally beautiful 1 BR/1 Bath with stunning sunset views in like-new condition. MANY UPGRADES: New Bosch HVAC Heat Pump costing $10K, New designer walk-in shower costing $12 K , New carpeting in Bedroom., Hardwood floors, granite counters. Many amenities : 24/7 live person at the Lobby Front Desk, very secure building, One owned/ assigned underground garage parking space with remote opener, Fitness Center, Outdoor Pool and Hot Tub, Two Outdoor Gourmet BBQ kitchens, Gardening Area, Library, Party Room , TV Lounge , Free Shuttle Service to downtown, just blocks to City Dock attractions: restaurants, entertainment venues, shopping. The most luxurious condo residence in this county.
#MDAA2121784

ANNAPOLIS

5 PARK PLACE 431

1 Beds

1 Baths

839 Sq.Ft.

$479,900

MLS#: MDAA2121784

Beautiful 1Br/1Bath facing east w pool/courtyard view. Hardwood floor, GE Stainless Steel appliances, Granite counter. Full Size W/D inside unit. 24 Hour concierge/security in lobby. 25 amenities including most utilities included in condo fee. Outdoor Pool, Fitness center, Party Room, Library, Outdoor Dining area with BBQ grills, Hot Tub, Dog Park and much more. Blocks to downtown City Dock restaurants, entertainment and shopping. Luxury Living in the heart of Annapolis.
#MDAA2140556

ANNAPOLIS

5 PARK PLACE 425

1 Beds

1 Baths

838 Sq.Ft.

$477,900

MLS#: MDAA2140556

Just Reduced to 474k. Welcome to the sought-after Newport Condominiums in Eastport, where coastal charm meets walkable Annapolis living. This beautifully updated 1 bedroom, 1 bath second-floor condo offers natural light, custom updates, and a coveted location just steps from Spa Creek and downtown Annapolis. The bright and inviting interior features built-in cabinetry, replaced windows, and stylish new light fixtures throughout. The updated granite kitchen offers modern finishes, while the renovated bathroom provides a fresh, coastal feel. Enjoy a slight water view of Spa Creek and the convenience of elevator access in this secure building. Large windows fill the home with natural light, creating a warm and comfortable living space. Located in the heart of Eastport, you’re just a short stroll to Annapolis’ favorite waterfront restaurants, marinas, and shops—and only minutes from the U.S. Naval Academy and historic downtown. The Newport community is known for its incredible walkability and access to waterfront amenities and scenic creek views. Newport offers marina slip rentals for their residents! Take a boat cruise along Spa Creek or out to the Chesapeake Bay. Community roof top pool is open in the summer months. This condo is perfect as a full-time residence, or weekend get away!
#MDAA2137216

ANNAPOLIS

316 BURNSIDE STREET 203

1 Beds

1 Baths

525 Sq.Ft.

$474,000

MLS#: MDAA2137216

BEACON WAY in HERITAGE HARBOUR! Just wait until you see the 10' x 12' Sun Room addition! It's bright and airy, and a lovely place to retreat to. Another bonus... you get to move right in! That's right, the Seller has made thoughtful updates along the way so you can envision your furniture and decorating style - the rest is done. Features I made special note of: Front porch. Vaulted ceiling in Living Room and Dining Room. Gas stove. Generous primary suite with walk-in closet. Ductless mini-split, skylight and palladian windows in the Sun Room. Roof replaced 8 years ago. HVAC is 10 years old. Water lines replaced in 2021. And, all the incredible amenities the community of Heritage Harbour has to offer! I pulled this from HHCA's site: ...an established community in Annapolis, offering beautiful wooded lots and featuring a wide variety of recreational, cultural, social, and educational activities for its residents. Residents can participate in over 90 activities, clubs and committees. The center of community activities is the Lodge, which features a welcoming atrium, an auditorium, indoor and outdoor pools, fitness center, library, boutique, activities room, woodwork shop, game rooms, coffee corner and meeting rooms. Behind the Lodge, residents enjoy a picnic area, horseshoes, bocce ball and kayaking on our waterfront on the South River. We also offer multiple tennis and pickleball courts, a nine-hole golf course, a pro shop, a clubhouse dining room, a pier with boat slips and RV and boat storage on a lot in the community. Residents enjoy the convenience of regular bus trips to shopping centers and special bus trips to cultural destinations, as well as volunteer drivers for medical appointments. Our pet-friendly community of active residents always welcomes newcomers! Can't wait for you to see this one - it's going to make you smile!
#MDAA2141580

ANNAPOLIS

907 BEACON WAY

2 Beds

2 Baths

1,234 Sq.Ft.

$465,000

MLS#: MDAA2141580

***PRICE REDUCED - SELLER MOTIVATED*** BY APPOINTMENT ONLY. 55+ Luxury 2-bedroom/den with balcony in an elevator condo building. THE ELEMENT boasts a variety of amenities to satisfy an active adult community. Natural light floods into the modern kitchen with white cabinetry, tiled backsplash, SS appliances & quartz countertops. Enhanced lighting & recessed lights throughout. Upgraded closet design w/a huge Master closet! Beautiful, light colored LPV flooring (no carpeting). Custom bathroom design with upgraded tilework. Double vanity in the master bath. Private balcony for sipping your morning coffee. Beautifully landscaped perimeter with a walking trail/path. Elegant lobby with automated golf room & pool table. Enjoy pickleball, dog park, outdoor grills & workout equipment. Assigned outside parking(Space#4) & lower-level storage unit(#20) included. (Wallpaper is peel-and-stick). Call today to see this great property with amenities galore! Quick drive to downtown Annapolis, waterfront dining, shopping & the Bay Bridge.
#MDAA2136282

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 209

2 Beds

2 Baths

1,210 Sq.Ft.

$457,700

MLS#: MDAA2136282

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