Annapolis Maryland homes for sale starting at Fifty Thousand Dollars

$975,000 - Annapolis, MD

1534 Circle Dr Annapolis, MD - Incredible PRIVATE oasis, in sought after community of Winchester on the Severn. One of a kind home, surrounded by protected lands. One of the highest and largest lots in the community, overlooking the wooded glen. Custom hardscaping with multi level decks, and numerous stone patios. Enjoy the tiered golf putting green and the outdoor spa hot tub! There are 2 beautiful sunroom additions on the back of the house, allowing nature to flow in. The windows and french style doors through-out affording light to flow and tree top views. Quality interor features include hardwood and marble flooring, custom cherry built-ins, in-law/au pair suite (that could serve as a optional second primary suite), featuring interior and exterior entry. Double covered carport parking and additioanl parking in driveway for several vehicles. Vaulted beamed ceilings, masonry fireplace and more! Community has a voluntary association of $260/yr. for use of community water amenities. Chase Creek Swim Club within walking distance. Explore miles of trails on foot or by bike, on the nearby Annapolis Baltimore Trail.

$975,000 - Annapolis, MD

1534 Circle Dr Annapolis, MD - Stunning contemporary in Winchester on the Severn featuring abundant windows that provide lovely views. Enjoy multi-level decks, patios, and custom hardscaping, complete with a private putting green and hot tub. Main level includes foyer, large sunroom, living room with stone fireplace - dining room combination, kitchen with granite countertops, main bedroom with adjoining full bath, 2 additional bedrooms and full bath in hall. The lower level includes another sunroom with exit to the rear yard, recreation room, study, and another very spacious room (potential 4th bedroom) with super bath and side exit. A real beauty! The Winchester on the Severn community offers a voluntary association fee of $260 per year for access to amenities, including a private beach, dock, canoeing, playground, and covered picnic pavilion . The community also has 2 different areas with boat slips that when available can be rented for an additional fee. The Chase Creek Swim Club is also nearby and joinable for an additional fee.

$974,990 - Annapolis, MD

201 Bonny Way Annapolis, MD - Exuding grace at the moment of entry, this expansive two-story home features an open-plan design on the first floor ideal for modern living. A charming fireplace stands at the center of the Great Room, which joins seamlessly with the dining areas and a chef-ready kitchen with a versatile island. Three restful bedrooms and a luxurious owner's suite with a spa-style bathroom occupy the top level. Throughout the home are a lower-level recreation room, a study and an upstairs loft for tons of additional space.

$950,000 - Annapolis, MD

849 Holly Dr S Annapolis, MD - This lovely home is located in water privileged Amberley on a quiet street near one of the community piers. The original owner has lovingly maintained this property since it was built in 1996. It has a light filled front entrance foyer, half bath, large living room with fireplace, eat-in kitchen, dining room, primary bedroom with a full bathroom, and a bonus room next to the dining room that faces the front yard. The upper level has two bedrooms, a large full bathroom and a huge unfinished room that could be turned into another bedroom. The lower level is completely finished with a half bath, kitchenette, family room, exercise room, office and workshop. Tons of storage also. On the back of the house there is a large deck that faces a beautifully landscaped fully fenced backyard with a shed and a sweet little pond.

$949,900 - Annapolis, MD

1383 Sunwood Ter Annapolis, MD - PRICE IMPROVEMENT! OPEN HOUSE - Tues 7/8, 5pm-7pm. Welcome home to this stately brick front colonial located on the sought-after Broadneck Peninsula. Meticulously maintained, this home has an open layout, is light and bright and features gleaming hardwood floors and an updated eat-in kitchen with granite counters, center island and stainless appliances. Kitchen opens to the large family room that boasts soaring ceilings and a gas fireplace. Just off the family room you will find the perfect home office with beautiful glass doors. All 4 bedrooms are incredibly spacious and include fantastic closets! The finished lower level has recessed lighting, a large recreation space, full bath, a great storage area and a huge bonus room perfect for a 5th bedroom or hobby area. A BRAND NEW composite deck with steel cable railings and built-in lighting overlooks the beautifully landscaped backyard and can be accessed from both the family room and the kitchen. The irrigation system will keep the lawn lush and green to keep that incredible curb appeal. Located in a Blue Ribbon school district with quick access to shopping, dining, recreation and major commuting routes. This home truly has it all.

$920,000 - Annapolis, MD

709 Pilot House Dr Annapolis, MD - PRICE IMPROVEMENT - SELLERS MOTIVATED. Welcome! Step into an inviting two story foyer that sets the tone for the entire residence! This home offers a blend of elegance and functionality. Many updates have been done by current homeowners. A three story, three-sided brick home on a corner lot that emanates timeless elegance. Enjoy two inviting front porches for relaxation. Entering the two story foyer with marble floor, framed mirrors, and a Juliet balcony. A formal living room, hardwood floors, with one of three gas fireplaces. The dining room, includes a mirrored wall, and hardwood floors. A half bath with marble tile floor is off the living room. An open concept kitchen, family room, laundry room and pantry are situated towards the back of the home. The kitchen is an entertainer's dream with a large two level granite island with cooktop, hardwood floors, and a double wall oven for your holiday baking! The family room with 19ft. beamed ceiling, floor to ceiling windows, hardwood floors, and the second gas fireplace and glass shelves. The family room looks out to a private enclosed fenced back yard with a two level slate patio to enjoy the gardens. On the second level, you will find a split hallway with hardwood floors. The primary bedroom, includes an attached bathroom which was updated in March 2022; a soaking tub with jets and a walk-in shower with dual shower heads, dual sink vanities, quartz counter tops. The primary bedroom, has a ten foot tray ceiling, ceiling fan, recessed lighting, wainscoting, two walk-in closets, and a sitting area. There are three other bedrooms on the upper level, the largest of the three features a private porch, hardwood floors, private bath with tub/shower, and ceramic tile floor. Perfect for visitors. Another bedroom features built-in bookshelves. The last of the four bedrooms overlooks the upstairs porch. The lower level is fully finished. A family room with built in counter w/cabinets, wainscoting, an egress window. Another room serves as a bonus room or flex room that could be used as a fifth bedroom, and is currently used as a gym. A home office that is a homeowners dream, with built in bookcases and shelves that includes the third gas fireplace. Another room currently used for storage, but can be used for hobbies, or to store your wine. A full bathroom is also located on the lower level. Crown molding throughout enhances the character of this home. Two new Air Conditioner Units- August 2017 and July 2019. Duct cleaning - March 2024, New Roof-Oct.-2019, Hardwood floors on main floor and stairs were refinished-May 2024. Kitchen counter to match kitchen island granite w/new sink April 2025. Sound surround throughout the house to include the outdoor patio. Central Vac, Sprinkler System, 75 Gallon Hot Water Tank- February 2022, Hot/cold water faucet in the garage, Security system. A community pool, two tot lots, walking trails, water access to Church Creek, dock, kayak launch, and kayak storage. Convenient to Rt.50/97 to D.C., Baltimore, Bay Bridge and beaches. 3.2 miles to Naval Academy, and historic downtown Annapolis.

$905,000 - Annapolis, MD

1901 Eamons Way Annapolis, MD - Welcome to this stunning 3 bedroom, 3.5 bath stone-front home situated on a large 9,289 sq .ft. corner lot in the sought-after Monticello community-just a short walk to shops and dining. The main level features an open living/dining area, gourmet kitchen with stainless appliances and granite counters, a spacious family room with gas fireplace that opens to a large screened-in porch, perfect for morning coffee or entertaining, a deck and private backyard. The upper level offers a large luxurious primary suite including a sitting area and ensuite bath with a soaking tub and large shower; two additional bedrooms; a full bath; and a versatile loft (ideal office or 4th bedroom). The fully finished lower level includes a large multi-use space, a wet bar, full bath, and ample storage. Enjoy the amenities of a community pool and dog park, and the convenience of nearby access to major commuting routes and downtown Annapolis.

$899,000 - Annapolis, MD

623 Second St Annapolis, MD - Welcome to 623 Second Street, a unique opportunity in exceptional Eastport! Located just a block from Back Creek, this charming two-bedroom, one and a half-bath home is situated on a beautiful corner lot in the heart of Eastport with ample street parking! The existing curb cutout offers the potential for a driveway in the back yard. Entering the home, you are welcomed to a long, open floor plan filled with natural light, fresh paint, and gleaming wood floors. The main level features an inviting living room that flows into kitchen and dining area and includes a laundry closet and a half bath. For your outdoor enjoyment, step out onto the patio and relax in a peaceful backyard enclosed by a beautiful wood fence (2024). Upstairs, a skylight brightens the hallway that leads to two bedrooms and a full bath. The primary bedroom features a rooftop deck that overlooks the rose-lined backyard. A great place to enjoy the Eastport lifestyle! The second bedroom space offers views of Back Creek and the option for an office, playroom, or gym. This beautiful property is enhanced by an amazing location with nearby water access to launch a kayak or paddleboard, catch the water taxi, or take an easy stroll to cafes, bars, and restaurants. A great place to call home!

$849,000 - Annapolis, MD

13 Lawrence Ave Annapolis, MD - Don't MISS this RARE OPPORTUNITY IN THE VERY POPULAR COMMUNITY OF BAY RIDGE. Make this Home Your Own! USE YOUR IMAGINATION! Great Location within STEPS to the Private Community Beaches etc.! 3,084 Total Sq Footage, .21 acre. lot size. THE BAY RIDGE LIFESTYLE IS UNMATCHED IN ALL OF MARYLAND! COMMUNITY POOL/CLUBHOUSE W/ WATERCRAFT STORAGE RACKS , PRIVATE COMMUNITY BEACHES! & THE BIG WOODS ""BAY RIDGE CONSERVATION AREA""Â? W/TRAILS AND ACCESS TO BLACKWALNUT CREEK, A TRUE GEM! WALK TO COMMUNITY MARINA,W/BOAT RAMP, MOORING BALLS & SLIPS, PLAYGROUND, BASKETBALL/PICKEL BALL COURT, KAYAK RACKS , Kass Park: BASEBALL/SOCCER, LACROSSE FIELD!! WHETHER YOU'RE A BOATER, SUP ENTHUSIAST, DOG WALKER, RUNNER, HIKER (PRIVATE TRAILS IN THE BIG WOODS), RUNNER, THIS NEIGHBORHOOD HAS IT ALL! JOINING THE BAY RIDGE CIVIC ASSOCIATION IS VOLUNTARY. Home is being SOLD STRICTLY AS-IS! DO NOT WALK ON SIDE DECK ENTRY AND DECK OFF MASTERBEDROOM!

$795,000 - Annapolis, MD

512 Tayman Dr Annapolis, MD - Welcome to 512 Tayman Drive - a beautifully renovated home tucked away in the water-privileged community of Hillsmere Shores. The moment you step inside you are greeted by the bright, airy and perfectly appointed selections of this happy home. The upper level features a seamless open floor plan, with refinished hardwood floors throughout. At the heart of the home is the stunning, fully renovated kitchen, complete with a spacious center island that flows effortlessly into the living and dining areas. Just beyond, a bright and expansive family room opens onto the back deck-ideal for entertaining or relaxing. Three bedrooms, including an en-suite primary, along with a stylishly updated full bathroom, complete the upper level. Downstairs, the freshly renovated lower level offers incredible flexibility. You'll find an additional inviting living space, a lovely sunroom (currently serving as a home office), a fourth bedroom, a full bath, a versatile flex space perfect for a playroom or home gym, and a dedicated laundry room. With plenty of natural light, this level is well-suited for an in-law or au pair suite. Set on over one-third of an acre, the fully fenced backyard is a private oasis-complete with a gravel fire pit for cozy evenings under the stars and a large shed for extra storage. Residents of Hillsmere Shores enjoy exclusive access to a premier community beach, marina, pool, multiple piers, and boat ramps. This vibrant neighborhood is located adjacent to the beautiful Quiet Waters Park and only minutes to historic Downtown Annapolis, with easy access to Routes 50 and 97 for effortless commuting. Welcome home to 512 Tayman Drive-where comfort, style, and Chesapeake living come together.

Annapolis, Maryland listings for sale

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