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$1,595,000
3 Beds ⋅ 4 Baths
This captivating Craftsman home with modern guest house provides the ideal setting for celebrating the Eastport lifestyle and is in the best location for exploring everything Annapolis/Eastport has to offer. The picturesque picket fence welcomes you onto the property and the front porch swing is the perfect place to unwind after a long day or have your morning coffee. The charming details from the 1920's are beautifully preserved throughout with the modern convenience of an updated kitchen, bathrooms and lighting fixtures. The open floor plan creates a wonderful entertainment space and the spectacular kitchen with large island makes hosting large or small gatherings a breeze. The full bathroom and mudroom adjacent to the expansive rear deck is conveniently located to encourage the party to spill outside and creates the ideal setting for indoor/outdoor living all year round. Upstairs enjoy 2 bedrooms with soaring ceilings, exposed beams, beautiful finishes and the luxurious bathroom featuring double sinks, curated finishes and soaking tub with shower. The quaint garage has been converted to a stunning guest house with spacious main level featuring 2 story ceilings, fireplace with built-in bench/TV entertainment area, sleek modern kitchen with enormous island and powder room. Upstairs is a loft bedroom, walk-in closet and full bath with catwalk balcony overlooking the space below. The coveted off street parking space and an abundance of street parking is a rare find. This property is the perfect location for a permanent residence, weekend getaway home or rent one or both dwellings to generate income all year long. Stroll the artful and nautical streets to amenities like; five-star restaurants, pubs and street-end parks with hidden treasures. Not to mention you are merely steps away from downtown Annapolis and Naval Academy. Annapolis offers the perfect balance of small-town charm and big world sophistication. Located just 5 miles to Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC.

813 Chesapeake Ave, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$1,695,000
3 Beds ⋅ 3 Baths
Newly renovated waterfront home with awe-inspiring water view across Crab Creek and out to the South River. This spacious ranch home is move-in ready with plenty of space for a large family or lots of guests. With 0.78 acres of land including the enormous front yard, there is ample room for running around with both kids and pets. The waterside backyard provides multiple areas for enjoying the waterfront lifestyle. Relax on the rear deck or the screened porch with soaring ceiling while watching the activity on the water or head out yourself from your private pier with boat lift and multiple slips. With easy access to the South River and beyond the location is a dream for a boating enthusiast. Step inside the spacious foyer with views through the house to the water beyond. The expanded Kitchen open to the dining room and wet bar is a chef's dream with large island, plenty of cabinets and counter space and high-end appliances. The sunken Living room with fireplace and adjoining screened porch are perfect for entertaining large or small gatherings. 3 bedrooms including the stunning Primary suite with walk-in closet and luxurious spa-like bathroom with freestanding soaking tub overlooking the amazing view. The upper level loft space has a multitude of uses including home office, play room, or hang out space. Completing this must see property is the 2 car garage with conveniently located mudroom. Located just minutes away from everything the Annapolis area has to offer by car or by boat. Don't let this opportunity pass you by. Welcome Home!

2652 Greenbriar Ln, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$524,990
4 Beds ⋅ 4 Baths
Welcome to the sought after community of Water’s Edge @ Woods Landing! This 4 bedroom, 4 bath former model home has upgrades throughout.. From hardwood flooring, plantation shutters, custom built-in shelving, and 2 gas fireplaces that make this home perfect for entertaining. Its custom brick exterior, flagstone entry, view of mature trees both front and rear, and 2nd level balcony welcome you in from the minute you enter. The gourmet kitchen is a chef’s dream that includes stainless steel appliances, granite countertops,newly finished cabinets, new hardware, breakfast bar, double sink and gas cooking!! Enjoy a cozy fire in your living room or head out to one of your two decks and enjoy a cold one! The lower level family room also has a cozy fireplace and is walk out level. But wait there’s more!!! The 4th bedroom or bonus room, you choose… is located in the upper level loft with its own bathroom, custom built in desk and TONS of extra storage space. The garage and shed storage are both climate controlled as well! The Community offers extensive wooded walking/jogging trails throughout the neighborhood (perfect for walking your furry friends ) a playground/tot lot, private community waterfront area with a pier and floating dock…the perfect spot to do some fishing or drop in your kayak! This home is conveniently located with easy access to Rte 50, Sandy State Park, Bay Head Park and downtown Annapolis. This one won’t last long!!

312 Pintail Ln, Annapolis

Listing courtesy of Keller Williams Flagship of Maryland. Contact:

$480,000
3 Beds ⋅ 3 Baths
Beautifully maintained and updated home in sought after Mariners Point! The home features a gorgeous kitchen with granite tops, granite island/breakfast bar and stainless appliances. You'll love the bamboo hardwood floors throughout the main level. Separate dining room. The master suite is enormous and has vaulted ceilings with a large walk-in closet and bathroom. Enjoy the lazy days of summer and fall on the large deck which offers privacy. Beautiful plantation shutters throughout. Great location close to shopping, restaurants, entertainment and minutes to downtown and historic Annapolis. Easy access to Route 50. This won't last long.

958 Yachtsman Way, Annapolis

Listing courtesy of RE/MAX Leading Edge. Contact:

$379,900
3 Beds ⋅ 3 Baths
OPEN HOUSE CANCELLED Welcome to Whispering Woods! You won't want to miss this spacious updated townhome in the newer side of the community. This move in ready home features three full finished levels, a large private deck overlooking the woods, a finished walkout basement, fresh paint top to bottom, new carpet, LVP and more! Convenient location near route 50 and Broadneck Schools! Showings start Saturday 9/16.

302 Sloping Woods Ct, Annapolis

Listing courtesy of Compass. Contact: (410) 429-7425
$1,750,000
5 Beds ⋅ 3 Baths
Welcome Home! This waterfront home with deep water is situated on over 5 acres nestled within a lush enclave of mature trees providing lots of privacy, a great place to relax and entertain. The home has over 3,200sq. ft. of living space and embraces outdoor living and a wonderful place to enjoy your morning coffee on the deck overlooking Church Creek. The home is filled with an abundance of natural light and the open-concept layout allows for a seamless flow and provides a comfortable and inviting living space. The spacious kitchen provides the perfect setting for entertaining and the separate dining room is ready for dinner parties. Enjoy the main level family room with fireplace that connects the kitchen and the deck offering an extension of living space and a great place to enjoy outdoor dining or relaxation. The lower level is a versatile space filled with tons of natural light offering a large recreation room with built-in’s, a second fireplace, three bedrooms, full bath, laundry and access to the garage. The lower level recreation room also provides direct access to the backyard featuring a stone patio with wonderful water views and evenings by the firepit. The layout on both levels provides a seamless connection to the outdoor space. Enjoy Church Creek via the well maintained private path to your pier with water, electricity and jet ski lift. This property has the deep water for your power or sailboat and don’t forget to grab your paddle board to enjoy the beautiful scenery. The property also offers a great opportunity with a separate structure - perfect setting for a home office, studio or gym. This location provides a unique opportunity to experience the best of both worlds - minutes to Eastport and downtown Annapolis, easy access to commuter routes and a peaceful retreat amidst nature and approximately 250’ of waterfront. Enjoy the fall foliage, holidays and waterfront lifestyle just off the South River and close to the Chesapeake Bay - this property is truly a gem.

1820 Woods Rd, Annapolis

Listing courtesy of Compass. Contact: (410) 429-7425
$430,000
2 Beds ⋅ 2 Baths
Your beautiful and spacious condominium in Heritage Harbor! One of the largest units available in this complex, fireplace, 2 bedrooms, 2 bathrooms, plus a den/office. Enjoy the woodland seasonal changes from your balcony. Security locked entrance. Community indoor & outdoor pools, golf, Rec Center(Lodge) & more. 55+ community Deeded underground parking space plus storage room included. Broadcreek HOA dues $489/mo.

803 Coxswain Way Unit #302, Annapolis

Listing courtesy of American Realty, LLC. Contact:

$205,000
2 Beds ⋅ 2 Baths
Location, location, location! This 2 bedroom 1 1/2 bath townhome is located in downtown Annapolis and could be the perfect starter home or investment property. Galley style kitchen , living/dining room combo, full bath and a laundry area/bonus room completes the main floor with a small additional storage area perfect to store bikes or hobby items. The upper level consists of 2 bedrooms, 1/2 bath and large bonus area that can be used as an additional living or office space. Paved fenced back yard is perfect for grilling and weekend gatherings. This property is conveniently located to downtown shops, restaurants, the city docks, waterfront, government buildings and public transportation. With a few updates and your own personal touches 56 Pleasant St could be"YOUR" affordable Annapolis Home Sweet Home! NO HOA or Condo fees! Property is being sold "As Is" Currently tenant occupied and showing appointments must be confirmed!

56 Pleasant St, Annapolis

Listing courtesy of Keller Williams Flagship of Maryland. Contact:

$389,000
2 Beds ⋅ 2 Baths
**Check out the video tour** Welcome to Your Dream Condo in Heritage Harbor Community! Check out all the features and amenities! Condo has been completely remolded…move-in ready! Hickory wood engineered flooring, granite kitchen and breakfast bar with stainless steel appliances, custom painted kitchen cabinets, kitchen arch with columns and pendant lights, transom windows above bedroom and french doors, custom built-in curved wood shelving, condo was recently painted. Neighborhood Amenities: outdoor pool, indoor pool with sauna, with bath/dressing rooms gym dock slips available $16 a foot per year tennis courts golf with membership available library meeting room picnic area for grilling pool table room media room coffee lounge full indoor kitchen pickle ball and ping room shuttle bus to local stores caring network to doctors Nestled in the highly sought-after Heritage Harbor Community, this stunning condo is a true gem, boasting an array of amenities and a prime location for boaters and nature enthusiasts. This 2-bedroom, 1.5-bathroom condo is ready to provide you with the ultimate in comfort and convenience. This condo offers the ultimate in convenience with covered garage parking and a private storage room. No more worrying about the elements when you come home, and you'll have ample space for all your belongings. In addition to your covered garage parking, Heritage Harbor offers overflow parking for your guests' convenience. Hosting friends and family has never been easier. Don't miss this incredible opportunity to own a piece of paradise in Heritage Harbor. With its fantastic amenities, boater-friendly location, and beautifully remodeled interior, this condo won't be on the market for long. Schedule your private showing today and start living the Heritage Harbor lifestyle!

803 Coxswain Way Unit #105, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: (888) 860-7369
$249,700
2 Beds ⋅ 1 Baths
Great starter home or rental. Home is located in the heart of Parole . Tenants just moved out; all systems working. As Is Sale. Seller is a licensed real estate salesperson. No Sign on Property.

30 Parole St, Annapolis

Listing courtesy of EKB Realty. Contact:

$335,000
2 Beds ⋅ 2 Baths
Step inside this inviting ground-level unit, and you'll be immediately impressed by its open-concept floor plan, creating a seamless flow throughout. The interior is adorned with a neutral paint palette , newer kitchen floor, new 2nd bedroom carpet, newer washer/dryer and HVAC was replaced in 2021. There is a nice patio with storage room. The primary bedroom is generously proportioned, with neutral carpeting, an en suite bath that has dual sinks, and a spacious walk-in closet. The second bedroom is equally spacious and comfortable, offering versatility for guests, a home office, or any other need that suits your lifestyle. A well-appointed hallway full bath serves both residents and visitors alike. The separate laundry room conveniently located off the kitchen, which also serves as a pantry offers amply storage shelves. A delightful outdoor patio that combines relaxation with practicality. Step outside, and you'll discover a secure storage. This Annapolis condo offers a prime location, an array of community amenities. Residents here enjoy access to a clubhouse, a well-equipped gym for fitness enthusiasts, a sparkling pool to unwind and cool off on sunny days, plus tennis courts and basketball courts. This remarkable property is just minutes away from Annapolis's vibrant downtown City Dock, the Anne Arundel Medical Center, the upscale Westfield/Towne Centre Malls, and offers easy access to major transportation routes such as Rt 50 and Rt 97.

605 Admiral Dr Unit #107, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact: (410) 487-2066
$355,700
5 Beds ⋅ 2 Baths
Home is tucked away at a calm dead end of the road, providing a tranquil escape from the bustle of daily life. Perfect for someone buying their first house! A fireplace in the living area, a kitchen, and a separate dining room. Excellent flat yard. Conveniently situated in the center of Annapolis, near to everything! Tenants just moved out; all systems working. As Is Sale. No Sign on Property. Seller is a licensed real estate salesperson.

111 Holeclaw St, Annapolis

Listing courtesy of EKB Realty. Contact:

$749,900
4 Beds ⋅ 4 Baths
What you have been waiting for - a pristinely maintained home in Riva Trace! The welcoming entry leads you to the open kitchen with dining area. Both this area and the adjacent family room have sliding doors to the deck and yard, perfect for running, playing and memory- making entertaining. The formal living and dining areas with beautiful hardwood floors and crown molding. Mudroom/laundry room off the garage makes life so much easier. Upper level features a primary bedroom with en-suite bath and custom walk in closet, plus 3 additional good size bedrooms and full hall bath. The lower level offers a recreation room , a den/study with full bath, in addition to a large storage area. Home also features a newer roof . High efficiency heat pump. Sidewalks for biking and walking the dog, Riva Trace's dock and kayak area with tables for picnicking, pickleball and tennis courts and a tot lot - these are just a few of the communities' amenities - and it's less than a mile to Route 50/665, shopping. HOA fee is $450 biannually and $100 for Autumn Chase once a year.

222 Autumn Chase Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: (410) 263-8686
$905,000
3 Beds ⋅ 3 Baths
Introducing 1707 Trinity Place, a meticulously updated mid-century modern retreat, nestled on a sprawling private lot within the serene enclave of The Downs on The Severn. This exquisite residence seamlessly marries its original architectural charm with modern luxury and conveniences, setting an unprecedented standard for attention to detail and craftsmanship. Originally constructed in 1975 and cherished by its original owners until 2017, this home underwent a comprehensive restoration and enhancement, both inside and out. Comprising three bedrooms and two and a half baths, this home boasts a versatile lower-level living/recreation area that can effortlessly transform into a fourth bedroom or a sophisticated home office. Additional features include a two-car garage, a convenient carport, and meticulously landscaped grounds designed for minimal upkeep, accentuating the natural splendor of the surrounding woodland. The expansive primary bedroom suite graces the main level and offers a generous sitting/dressing area, complemented by a spa-inspired bathroom adorned with a double marble vanity and radiant heated floors. The fully renovated kitchen boasts abundant storage and counter space, with a thoughtfully designed peninsula serving as the heart of daily life. A spacious rear deck beckons for relaxation and panoramic views that envelop the residence, accompanied by the soothing sounds of a nearby stream meandering down the hill. The voluminous open living area effortlessly accommodates family gatherings yet retains an inviting warmth, thanks to a substantial wood-burning fireplace. A second gas-burning fireplace awaits downstairs, and the rare inclusion of natural gas further distinguishes this property within The Downs community. Residents of this neighborhood enjoy access to a wealth of amenities, including a pool, clubhouse, tennis and pickleball courts, two deep-water marinas, and a bustling calendar of community events, all for a reasonable HOA fee. Notably, the larger marina is slated for a comprehensive overhaul in the Winter of 2023-24, a project that has been fully permitted, with current HOA fees already adjusted to cover the associated costs. Boating enthusiasts will appreciate the thoughtfully designed floating dock system, destined to become one of the most coveted features on The Severn River. For a comprehensive list of recent improvements, please don't hesitate to request more details. Welcome to a truly exceptional lifestyle at 1707 Trinity Place.

1707 Trinity Pl, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 224-0600
$2,750,000
3 Beds ⋅ 4 Baths
THIS COSMOPOLITAN CONDOMINIUM is a stunning transformation of the previous Annapolis Recreation Center, originally constructed in 1942 as a USO building. It presents a RARE OPPORTUNITY to own a modern residence within the protected Historic District of downtown Annapolis, just steps away from the City Dock waterfront & bustling Main Street! A private open air terrace offers sweeping views of Annapolis Harbor, the USNA, and the Chesapeake Bay! Experience seasonal sailboat races & regattas, international boat shows, annual Blue Angels flyovers, and holiday “Midnight Madness” shopping! THIS 2-LEVEL PENTHOUSE CONDO is the masterpiece of the Annapolis architectural firm Hammond Wilson, renowned for their award-winning designs. Some of the notable features of this property include secured off-street garage parking, new balconies and terrace, and a sophisticated interior design palette that incorporates high-end detailing, e.g., Thermador and Sub-Zero appliances, all-wood Kountry Kraft cabinets, quartz countertops, Walker Zanger tiles, and Kohler fixtures throughout. It offers 3 spacious bedrooms and 3.5 baths, with a main level primary bedroom suite showcasing two walk-in custom California Closets and luxe bath. The living room includes a gas fireplace and opens to a private terrace with IPE Deck & O.W. Lee gas fire pit providing an alfresco escape for relaxation with unmatched water & downtown vistas. On the second level, there is a large den with an additional gas fireplace accented with stone tile and custom-built ins, separate laundry room, and two more bedrooms each with private bath and views of the US Naval Academy, City Dock’s "Ego Alley" waterway, and glimpses of the Chesapeake Bay and Saint Mary's Chapel. Enjoy entertaining and serving fine wines from your wine room with an impressive automated illumination system. In essence, this grand Condominium combines HISTORICAL CHARM with MODERN LUXURY, making it an unparalleled and discerningly appealing property in the beating heart of downtown Annapolis. SIMPLY SENSATIONAL.

99 Compromise St Unit #RESIDENCE FIVE, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$450,000
2 Beds ⋅ 1 Baths
This quaint 1950's detached home in Eastport's water access community of Parkwood has a lot of the original charm remaining, but with several updates! Updated Kitchen, roof, siding and windows have been completed within the past 10 years. Enjoy your convenient private rear parking pad and large backyard, great for the gardening enthusiast or use the space to create your dream Eastport oasis. Don't miss this opportunity to live in Eastport within walking distance to Downtown Annapolis, Eastport Shopping Center (with a gym) and Quiet Water's Park. Don't miss the opportunity to live your Annapolis lifestyle in the in a budget friendly price range.

1303 Bay Ridge Ave, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$260,000
2 Beds ⋅ 1 Baths
Up and coming area within walking distance to everything that Annapolis offers.... College Creek, Navy Marine Corps stadium, St. John's College, USNA, Maryland Hall for the Arts, City Dock, art galleries, restaurants, the State House, water taxis, and more. Enter this 1940's row house with lots of updates to the home to make it energy-efficient, fitted with central air conditioning and a renovated bath. Windows, roof, HVAC, Insulation, Hot Water Heater, Kitchen appliances, Front and Back Doors, and storm doors all replaced in 2013. Lovely hardwood flooring on both levels. Full sized washer & dryer on the upper level. Ceiling fans throughout for added air circulation. 2 Bedrooms with an optional 3rd, use it as a nice office/craft room or expand. No HOA or condo fees. Rear fenced yard with nice outdoor deck for enjoying a little nature time. Currently served by Verizon Fios internet; Comcast is also available. Ready to move in and make your own. Ask about special financing and programs for first time buyers.

76 Clay St, Annapolis

Listing courtesy of Kinetic Realty, Inc.. Contact: (443) 222-0010
$8,295,000
5 Beds ⋅ 8 Baths
This Georgian-style estate marries the very essence of quintessential Chesapeake living with the gracious allure of Southern charm. Ideally sited on 6.12 picturesque waterfront acres along the serene shores of Duvall Creek, this home offers an unparalleled blend of luxurious living and architectural excellence. This custom-designed masterpiece underwent a complete renovation down to the studs in 2019–2020 and is the result of a collaboration between Gate One Builders and Purple Cherry Architects. The home boasts a wealth of exquisite features, from its designer fits and finishes to endless examples of fine craftsmanship. Custom millwork throughout includes coffered ceilings, custom moldings, lovely ceiling treatments, wide plank oak floors, and numerous arched doorways. The home was meticulously designed to highlight its exceptional waterfront location, with generously proportioned living spaces that artfully lead your eye to the breathtaking water views. Main level highlights include an open floor plan living room with gas fireplace and adjacent dining room with multiple sets of French doors that open to the waterfront terrace, creating a seamless blend of indoor and outdoor living. The gourmet kitchen and butler’s pantry are a chef's dream, with Vermont Imperial Danby marble countertops, custom alder wood island, and custom cabinetry with curated storage and display features. The family room has custom cabinetry with window seats, bookshelves, storage, and an expansive bar, which opens to a covered bluestone terrace, provides the perfect setting for relaxation, and the dramatic and refined library is a true show stopper. An elevator adds convenience and accessibility to all four levels of this magnificent home. As you ascend to the second floor, you'll discover three spacious bedrooms including the primary suite. Each bedroom is South facing, with an ensuite bathroom and waterfront balcony. The third floor presents two more bedrooms, both facing South and also featuring ensuite bathrooms. The fifth bedroom on this level is ideally suited as an upper-level office, complete with a private IPE balcony overlooking Duvall Creek and the South River. The lower level basement is a haven of wellness and relaxation, featuring a gym with a sauna for unwinding after a long day. A full bathroom, bonus room, dog washing area, and walk-up stairs to the backyard offer added versatility and convenience. The exterior of this estate is equally as impressive, featuring a fully-fenced yard, stately, secured circular drive, elegant entry and portico, two-car garage, tastefully designed hardscaping, and meticulously selected landscaping with irrigation for year-round beauty. Numerous waterfront IPE balconies each offer a haven of tranquility. The backyard is a true oasis, with a grand terrace facing the water, integrated fire pit area, and an expansive flat yard with 233’ of water frontage, perfect for outdoor activities and gatherings. A 250’ dock with 30,000-pound lift and a 7' mean low-water depth combined with location is a boater's dream, providing easy access to Annapolis and the Chesapeake Bay. With its custom finishes, spectacular water views, and meticulous attention to detail, this stunning estate offers a rare opportunity to experience waterfront living at its finest. For more in-depth details of this amazing home, please see the Features List uploaded in the documents section.

3200 Arundel On The Bay Rd, Annapolis

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 906-3848
$275,000
1 Beds ⋅ 1 Baths
This one bedroom, one bath condo provides a LIVE LIKE YOU ARE ON VACATION lifestyle in West Annapolis. Maintenance free and easy living in a small private community with a fabulous location on Weem’s Creek. Mariners Cove offers a waterfront community pool, dock, boat slips, paddle board/kayak rack, boat ramp and mooring. Walk, bike or boat to historic downtown Annapolis. Convenient location across from Navy Stadium and easy access to Rte 50.

304 Forbes St Unit #G, Annapolis

Listing courtesy of RE/MAX Executive. Contact: (443) 274-1900
$599,000
3 Beds ⋅ 2 Baths
Gorgeous fully remodeled 2,218 sq ft 4 level home in secluded cul de sac. Brand New belt driven garage doors with built in Wi-Fi and MyQ technology to work from smart phone anywhere in the world. Brand New jet tub whirlpool bathtub and shower in Master Bathroom. Stainless Steel appliances and granite countertops. Walk out great room can be converted to 4th bedroom with 3rd bath. Brand new landscaping, freshly paved driveway. Great short term rental income with no HOA restrictions.

1165 Green Holly Dr, Annapolis

Listing courtesy of Sell Your Home Services. Contact: (877) 893-6566
$745,000
4 Beds ⋅ 3 Baths
RARELY available rancher in extremely sought after community of Winchester on the Severn!! Please don't visit the home without visiting one of the best if not THE best community beach in the area!! A perfect golf cart community where you will feel like you are on vacation every day!! This stunning home is perfectly located in the heart of the community and will be sure to impress. You will immediately feel at home upon walking into the spacious family room anchored by a brick front wood burning fireplace. The family room flows seamlessly into the dining area and kitchen which then flow into an awesome vaulted sunroom. The kitchen was updated in 2014 and features SS appl, granite countertops, gas cooking and perfectly located skylight. 3 generous bedrooms including the owner's suite are located on the main level. Both the owner's en-suite bathroom and shared hall bathroom were renovated last year and are designer inspired gorgeous! Full WALKOUT basement with full windows and tons of natural light await you downstairs. Two recreation areas, a fourth bedroom, another FULL updated bathroom, laundry room and huge storage area will make you realize very quickly that this home has a lot more to offer than you may have expected!!! Behind the home are 5, yes 5, gravel parking spots that are ideal for boat, jet ski, additional parking along with another 2 spots next door on Winchester Rd. Homes like this in this type of neighborhood don't come along very often - don't hesitate!!!

1517 Winchester Rd, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$225,000
2 Beds ⋅ 1 Baths
Welcome to the heart of downtown Annapolis, where city living meets historic charm! This 2-level, 2-bedroom, 1-bathroom townhome offers an incredible opportunity to be just 2 blocks away from the Capitol building, shopping, restaurants, and the picturesque waterfront filled with boats. Convenience is key with parking included, allowing you to explore the vibrant downtown area with ease. Kitchen appliances are also included in the sale, making this property quicker for you to move in and enjoy. Currently, there is a tenant in place, so please refrain from disturbing or attempting to show the property until after the move-out date. The seller would prefer an "AS-IS" contract, but this home has plenty of potential at such an attractive price point. It's an excellent candidate for 203K financing, as it is livable now but could benefit from some cosmetic updates to suit your personal style. Don't miss this rare opportunity to own a piece of Annapolis for under $250,000! Get your offer in now before showings open up to all interested buyers. This charming townhome is your ticket to experiencing the vibrant downtown lifestyle Annapolis has to offer or add another rental property to your portfolio.

61 Clay St, Annapolis

Listing courtesy of ExecuHome Realty. Contact:

$1,270,000
3 Beds ⋅ 5 Baths
Striking modern colonial located in Eastport! This beautifully crafted and finished home boasts 4 levels of living space including the partially finished basement with full bath and wet bar. The cheerful colors and front porch with balcony above greet you are you enter onto the property. The wide open floor plan on the main level features a thoughtful layout including a massive island; perfect for entertaining. The bonus room off the kitchen is an ideal location for a home office and the oversized mudroom with powder room and conveniently located storage area provide options for a variety of uses. Head upstairs to enjoy the spacious Primary bedroom ensuite with custom closet, luxurious bathroom and the balcony that covers the entire width of the home. A perfect place to relax and watch the world go by. 2 more spacious bedrooms with 2 full baths finish out the 2nd floor. The 3rd level features a loft area with balcony overlooking the backyard. Stroll the artful and nautical streets to amenities like; five-star restaurants, pubs and street-end parks with hidden treasures. Not to mention you are merely steps away from downtown Annapolis and Naval Academy by either walking across the Spa Creek drawbridge or motoring in the water taxi. From this location, you are also close to some of the Bay's best cruising and fishing areas. Attractive destinations such as Baltimore's Inner Harbor, St. Michael's, Oxford, and Solomon's Island are only a short cruise away. Annapolis offers the perfect balance of small-town charm and big world sophistication. Located just 5 miles to Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft.Meade/NSA and Washington, DC. Don't let this opportunity slip away.

1012 Bay Ridge Ave, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$725,000
1 Beds ⋅ 1 Baths
Welcome to your Eastport oasis! Deep lot with main house and guest house, beautifully landscaped yard ready for entertaining. The main house offers tons of charm and natural light with a flex space that could be perfect for a studio or office. The guest house is recently updated, including new flooring, carpet and kitchenette, with possible ADU, rental, or investment opportunities. Enjoy a walk-able lifestyle with easy access to all the shopping and dining Eastport and downtown Annapolis have to offer. Come see this gem today!

1206 Bay Ridge Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: (410) 263-8686
$324,500
2 Beds ⋅ 2 Baths
Ready for Immediate Move-In! This meticulously cared-for first floor corner condo boasts 2 bedrooms and 2 baths, radiating a fresh and airy ambiance and freshly painted. Hosting dinner guests is effortless with the open-concept living room with gas fireplace and adjacent dining area. The galley kitchen features ample cabinetry and countertop space. The Primary Bedroom is a spacious retreat, featuring a walk-in closet, a separate sitting area, and an en-suite bath with a large garden tub. The secondary bedroom and full bath are conveniently located down the hall. An in unit washer and dryer are tucked away in separate laundry area. This tranquil ground floor unit is situated within the secure confines of the gated Tidewater Colony community, offering an array of outstanding amenities, including a pool, fitness room, club house, nature trails, and beautifully manicured grounds. Located in a prime spot, you're just minutes away from downtown Annapolis, Annapolis Town Centre, the Naval Academy, and major commuting routes such as 50 and 97. Welcome to your new home!"

2010 Peggy Stewart Way Unit #104, Annapolis

Listing courtesy of Redfin Corp. Contact: (410) 202-8454
$899,900
3 Beds ⋅ 3 Baths
COMING SOON!......Are you in search for a MAIN FLOOR PRIMARY BEDROOM SUITE? Well here it is! This 3500 sq. ft. custom-built contemporary home features a main level primary suite with en-suite bath. It will accommodate one level living or enjoy all the space it offers. From the oversized garage and kitchen, it's easy access to the full-size elevator running from the lower level to the main level. The foyer is a welcoming space leading you into the light filled and spacious kitchen with gas cooking, granite countertops and stainless steel appliances. The kitchen will be a gathering place as it opens to the dining and living areas. The main level also features a 2nd bedroom, full bath, home office nook, pantry and laundry room. The upper-level with it's designer touches offers up a bonus room that could easily be a 4th bedroom and the loft is perfect for additional office space or play area. The lower level is finished with a comfortable family room, gas fireplace, wet bar, 3rd bedroom, full bath and utility room; all of which could be used for an in-law or teen suite. That's not all...You’ll enjoy a peace of mind through storms as this home is equipped with a whole house generator. The water privileged community of Winchester on the Severn is in the Broadneck school system and is conveniently located to downtown Annapolis and Rt. 50.

1604 Riverside Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: jim.parks@cbmove.com
$299,900
2 Beds ⋅ 2 Baths
Welcome to Clipper Cay Condominiums located in the 55+ amenity-rich community of Heritage Harbour. This 2 bed /2 bath condo, with a private balcony, has been totally renovated with updates throughout. Located in walking distance to Club House. Amenities include indoor & outdoor pools, exercise rooms, golf course, tennis courts, bus service, and MORE. Professional photos and additional details Coming soon!

2900 Shipmaster Way Unit #203, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$259,900
2 Beds ⋅ 2 Baths
Newly renovated 2 bedroom, 2 bath condo, only minutes from downtown Annapolis. Updated kitchen includes flooring, cabinets, and granite countertops. Condo fee includes gas heat, cooking, and hotwater. Community amenities include pool, tennis court, tot lot and picnic area.

204 Victor Pkwy Unit #E, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: jim.parks@cbmove.com
$649,900
3 Beds ⋅ 4 Baths
Spanning 3,000 sq. ft. across three levels, this impeccably maintained Mid-Town Annapolis residence effortlessly delivers convenience and comfort in every room. Ideally situated just minutes away from Downtown Annapolis and the banks of the breathtaking Chesapeake Bay, this urban chic brick townhome provides easy access to I-97 and Rt. 50. One of only 12 “work/live” townhomes in the coveted Village Greens community, this rare gem boasts a first-floor commercially-zoned optional business space with a separate entrance. Featuring surround sound, a mini-split system for added heating and cooling comfort, roomy half bath, and a separate lock-off door from the main residence, this space is an entrepreneur’s dream. Not ready to turn your passion into a business? No worries, the open floor plan seamlessly melds into the personal residence to be used as a rec room, game room, state-of-the-art gym, private in-law suite, or whatever you can dream up. Parking is a breeze with exclusive gated access to a 2-car rear-entry garage for residents, as well as on-street parking for business clients and/or guests. Quality craftsmanship abounds, with features such as 9' ceilings, triple crown molding, abundant recessed lighting, hardwood flooring, custom window treatments, and an open gourmet kitchen where family can gather to make lasting memories. The kitchen leads to a private, low-maintenance deck boasting a pass-through gas fireplace complete with a 65-inch 4K Samsung all-season outdoor TV and integrated mounted speakers. It is the perfect setting to watch the big game or enjoy a romantic movie night. The main level also hosts a private office, an elegant dining area, a separate living room, and a convenient half bath. Upstairs, discover a dedicated laundry room, three spacious carpeted bedrooms, two full bathrooms, a bonus room/sitting area with a luxurious two-person infrared sauna for health and relaxation. The primary bedroom features lofty 10’ ceilings, a walk-in closet, and a built-in custom oak wet bar cabinet for the convenience of enjoying coffee in bed. The primary bath offers double sinks, a jacuzzi tub, and a separate shower. Don’t miss an outstanding opportunity to embrace the Annapolis lifestyle, combining the luxury of your personal spaces with the charm, convenience, and energy of vibrant city living. Enjoy proximity to restaurants and shops within walking distance, with the option to join the neighborhood pool.

703 Skippers Ln, Annapolis

Listing courtesy of Redfin Corp. Contact: (410) 202-8454
$700,000
4 Beds ⋅ 4 Baths
Welcome to your dream home! This spacious 4-bedroom offers a perfect blend of comfort, style, and convenience. Situated in a sought-after community with numerous amenities, this well-maintained property has everything you've been looking for. Enjoy the timeless beauty of real hardwood floors that grace the entire home, adding warmth and elegance to every room. The updated kitchen is a chef's delight, featuring updated cabinets with soft-close doors, modern appliances, and plenty of counter space for meal preparation. The luxurious primary bedroom features a sitting room, en-suite bath with a soaking tub, and walk-in closet. Your personal retreat awaits! A sparkling, new walk-in shower has just been installed in the hall bath. Stay cozy during the winter months with efficient and cost-effective natural gas heating. The basement offers a world of possibilities. It comes with a convenient half-bath, cedar closet, egress window and ample storage space. It's ready for your finishing touches to create the perfect entertainment area, bedroom or home office. This community amenities include a pier, kayak storage, picnic area, pickleball and tennis courts, a fitness trail, and tot lot. There's always something to do right in your own neighborhood. Located with easy access to major commuting routes, you'll have a hassle-free daily commute to work and enjoy proximity to shopping, dining, and entertainment options. Don't miss this opportunity to own a stunning 4-bedroom home in a fantastic community. Schedule a viewing today to experience the charm and comfort this property has to offer.

255 Autumn Chase Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: jim.parks@cbmove.com