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
318
# of Listings
3
Avg # of Bedrooms
$463
Avg. $ / Sq.Ft.
$1,069,668
Med. List Price

Browse Annapolis Real Estate Listings

50 Properties Found. Page 4 of 4.

Welcome to 26 Pleasant Street: a charming 2-bedroom, 1-bath home in the heart of Annapolis, just steps from West Street’s restaurants, shops, and nightlife.

Whether you’re looking for a primary residence, weekend getaway, or investment, this home offers incredible flexibility. This turnkey property is not only move-in ready but also a proven licensed Airbnb performer, with nearly $40,000 in earnings in 2024 and over $22,000 already booked through August 2025. 

Inside, the main level features a spacious family room, dining area, and kitchen that opens to a deck and fenced backyard, perfect for entertaining. Upstairs, you’ll find two bedrooms, a full bath, and a bonus loft area for an office or guest space.

Don’t miss your chance to own an Annapolis gem with walkable lifestyle perks and a track record of short-term rental success.
#MDAA2125926

ANNAPOLIS

26 PLEASANT STREET

2 Beds

1 Baths

972 Sq.Ft.

$299,900

MLS#: MDAA2125926

**LISTING DESCRIPTION UPDATED 10/3/2025**
This top-floor penthouse condo has been extensively renovated from top to bottom, offering modern finishes, durable materials, and functional design updates. Every major system and space has been improved.
LAYOUT IMPROVEMENTS:
Walls were reconfigured to expand the footprint and create a more open flow. A dedicated laundry closet was added for convenience, featuring an oversized Maytag washer and dryer.
BATHROOMS:
The original 1.5 baths were converted into 2 full baths. Both include new tile, new toilets, and stone-top vanities with Delta faucets. Showers were rebuilt with concrete board and green board for long-lasting durability. The primary bath includes a new tub surround and exhaust fan. The hall bath features a raised ceiling, full tiled walk-in shower, and a new exhaust fan with LED light. Mold and mildew-resistant PVC baseboards were installed in both bathrooms.
PLUMBING:
All water shut-off valves, sinks, and fixtures were replaced throughout the unit, ensuring updated and reliable plumbing.
FLOORING AND FINISHES:
All previous carpet was removed, subfloor leveled, and commercial-grade waterproof luxury vinyl plank installed throughout. New 5” decorative baseboard trim was added, and the entire condo has been freshly painted with accent walls for a modern finish.
WINDOWS & DOORS:
All windows and the sliding glass door were replaced with energy-efficient, noise-reduced models. Bedroom windows tilt inward for easy cleaning.
LIGHTING & ELECTRICAL:
Significant electrical upgrades were completed, including a new electrical panel and replacement of all switches/outlets. Lutron Alexa-ready dimmers were installed, with 3- and 4-way wireless switching and remote controls. Downlighting and/or ceiling fans were added in every room. Commercial-grade dim to warm 3000k-1700k fixtures are indirect in living room & dining area and direct lighting in hallways & kitchen. Built-in GFI night lights were installed in the kitchen and baths. The kitchen features commercial-grade dimmable downlights at 4,000k for task lighting, eliminating shadows in prep areas. Surround sound and ethernet wiring were run through the living room walls. Modern light fixtures were added in the bathrooms and over the primary bedroom vanity.
HVAC:
Gas furnace and HVAC were replaced 2.5 years ago, including updated breaker, gas shut-off valve, and insulated ducts. A WiFi-enabled thermostat was added in the living room.
KITCHEN:
The kitchen was fully remodeled. Bulkheads were removed to allow for a full-size refrigerator. Cabinets were updated with pull-out drawers for additional storage. Dark granite countertops with a 4” backsplash complement an oversized stainless steel sink, Kohler pull-down faucet, and new garbage disposal. Ventilation was upgraded with a larger, quieter exhaust fan. Appliances include dark stainless steel Whirlpool refrigerator, dishwasher, and gas oven.
ADDITIONAL UPGRADES:
New closet doors were installed, and the primary bedroom was redesigned with updated finishes. A TV wall mount with in-wall hidden cable pass-through was added, complete with pull string for future wiring.
BUILDING UPDATES:
The roof was replaced five years ago, and tuckpointing completed one year ago, both handled by the condo association.
EFFICIENCY & COSTS:
Gas and water are included in the condo association fees, covering furnace operation.
#MDAA2122610

ANNAPOLIS

10 SILVERWOOD CIRCLE 10

2 Beds

2 Baths

1,164 Sq.Ft.

$299,900

MLS#: MDAA2122610

Welcome home to this spacious two bedroom two full bath condo with a loft. Stainless appliances in the kitchen, the stove is brand new, fine cabinets and granite countertops. Hardwood flooring in the living room and dining room, and a nice balcony though the living room slider. The primary bedroom has a large walk-in closet and attached full bath. And, the second bedroom is across the hall from the second full bath. Go up the spiral staircase to a huge family room area. The bathrooms were renovated in 2024 and the washer and dryer were replaced in 2024 as well. There are two (dual) HVAC systems, one for the lower level (replaced in 2022) and one for the loft (replaced 2019).  The community has a great outdoor pool for summertime, and across Hilltop Dr is plenty of recreational opportunity at The Pip Moyer Rec Center and Truxton Park. Great price for a great location!
#MDAA2126114

ANNAPOLIS

300 HILLTOP LANE 300I

2 Beds

2 Baths

1,321 Sq.Ft.

$290,000

MLS#: MDAA2126114

MOTIVATED SELLER, JUST REDUCED ANOTHER $10,000!!    It's a life of luxury amid the Annapolis waterfront shores of the Chesapeake Bay. You've earned this! Sit back, relax and take in the incredible views while someone else takes care of the cooking and cleaning... Nothing to do but live your best life! Immense social opportunities await: meet your friends on the putting green or have cocktails on the waterfront deck, walk the shores of the Chesapeake and never leave your home.  Monthly Co-op fees covers all utilities, taxes, insurance, multiple dining options, weekly house cleaning, maintenance/replacement of appliances, including HVAC,  local transportation, a wide variety of fitness/social functions.  Not to mention, on-site banking, convenience store and beauty/barber shop. Baywoods of Annapolis is a premier retirement community offering all the perks of being a homeowner, with the peace of mind that help is immediately available. It's your New Waterfront Home and you'll never want to leave!
#MDAA2116362

ANNAPOLIS

7101 BAY FRONT DRIVE 400

1 Beds

1 Baths

1,000 Sq.Ft.

$265,000

MLS#: MDAA2116362

MAJOR PRICE ADJUSTMENT on this lovely flat lot in a private, convenient neighborhood.
This lot was subdivided many years ago and used by the present owners for picnics and famly gatherings. 
Please contact the listing agent with any questions. And drive by but do not walk the lot without prior authorization.
Please contact the listing agent regarding the potential availability of the house next door.
#MDAA2116978

ANNAPOLIS

29 COLLISON ROAD

None Beds

None Baths

0.29 acres

$250,000

MLS#: MDAA2116978

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