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$619,000
2 Beds 3 Baths
Enjoy resort-style waterfront living with harbor and Chesapeake Bay views in the gated community of Chesapeake Harbour. This beautifully updated two-level residence offers the ideal blend of comfort, natural light, and low-maintenance coastal living. Freshly painted throughout with new carpet, the home features a thoughtfully designed floor plan with over 1,900 square feet of living space, an attached 2 car garage with interior access and additional parking out front, a rare and coveted amenity in the neighborhood. The entry level features an eat-in kitchen with white cabinets and counters, powder room and laundry room with a few steps up to the living room. The thoughtfully designed split-level layout creates a natural separation between the home’s functional spaces and its main entertaining areas, allowing gatherings to flow effortlessly while keeping day-to-day tasks discreetly tucked away. The dramatic living area where soaring ceilings, gas fireplace with custom built-ins, and walls of windows fill the space with natural light while framing the harbor views. Step outside to the expansive full-width waterside deck, the perfect setting for morning coffee, evening cocktails, or simply enjoying the marina activity and views stretching toward the Chesapeake Bay. Upstairs, the spacious primary suite offers a balcony, an ensuite bath with new cabinet and drawer fronts, and a peaceful retreat for relaxing after a long day. A loft-style flex space overlooks the living room below and can easily function as a second bedroom, home office, or additional lounge area, complemented by a full hall bath. Life in Chesapeake Harbour feels like a year-round vacation with an unmatched collection of resort-style amenities, including two waterfront pools, a private sandy beach, exclusive fitness center for a small enclave of residents, tennis and pickleball courts, fishing piers, walking and jogging paths, picnic areas with grills, scenic Chase Pond, and the security of a 24-hour attended gatehouse. The newly opened waterfront marina restaurant adds to the vibrant atmosphere with outdoor dining and live music on weekends. Ideally located just minutes from Downtown Annapolis, Eastport, the United States Naval Academy, waterfront dining, shopping, and historic attractions, this exceptional residence also offers easy access to Washington, DC, Baltimore, and Baltimore/Washington International Thurgood Marshall Airport. Whether you are searching for a full-time residence or a lock-and-leave waterfront retreat, this home offers the very best of the Annapolis waterfront lifestyle. Welcome Home!

2002 Dakota Pl Unit #2A, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$578,000
2 Beds 2 Baths
Welcome to easy waterfront living in the heart of Eastport. Rarely available and beautifully renovated, this top-floor 2-bedroom, 2-bath condominium in the sought-after Severn House community offers direct views of Back Creek, turnkey interiors, and effortless access to the Annapolis waterfront lifestyle. Inside, the residence has been thoughtfully updated with a clean, coastal feel and comfortable, move-in ready finishes throughout. The open-concept living spaces are bright, inviting, and designed for easy everyday living. The kitchen opens to the dining area and living room, creating a comfortable flow for entertaining, gathering, or simply enjoying the sense of space. From the main living area, sliding glass doors lead to a private balcony with direct views over Back Creek, adding a beautiful waterfront backdrop to the home. The primary suite features an ensuite bathroom and walk-in closet, while the second bedroom offers a gracious closet and utilizes the full hall bath. A washer/dryer combo unit adds everyday convenience. Severn House is one of Eastport’s most beloved waterfront communities, known for its relaxed atmosphere, mature landscaping, and exceptional amenities. Residents enjoy a waterfront pool with spacious patio and deck areas, an outdoor clubhouse pavilion, kayak, canoe, and paddleboard launch, bike storage, communal laundry, on-site management, and available water taxi access from the dock. Please note that pets are not allowed in this community (exception for support animals that are approved). Gas and water are included in the condo fees. Just minutes from downtown Annapolis, Eastport restaurants, shops, marinas, and local favorites, 774-F Fairview Avenue offers a rare turnkey opportunity in one of Annapolis’ most convenient waterfront communities. 30-foot boat slip being sold separately - reach out for details.

774 Fairview Ave Unit #F, Annapolis

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

$1,149,000
2 Beds 3 Baths
Enjoy luxury one-level living in the heart of downtown Annapolis in this unique, penthouse condo with a one-of-a-kind, beautifully landscaped, expansive terrace. The condo includes two bedrooms plus an office or 3rd bedroom, 2.5 bathrooms and an open floor plan. Leave the cars in your secure two garage parking spaces, and walk to dinner, the waterfront, the Naval Academy, concerts, Maryland Hall for the Arts, and City Dock. This condo offers a seamless, turnkey lifestyle anchored by an open, light-filled floor plan enhanced by floor-to-ceiling windows and premium finishes throughout. The private terrace is an inviting outdoor retreat ideal for dining, entertaining, or simply relaxing under the retractable awnings on sunny afternoons. The gourmet kitchen is designed for both everyday living and effortless entertaining and features high-end appliances, gas cooking, a large island with ample work space, and dedicated wine storage. A sun-filled office that doubles as a 3rd bedroom, provides the perfect work-from-home space, while the spacious primary suite and second bedroom—thoughtfully positioned on the opposite side of the residence for added privacy—provide exceptional comfort for owners and guests alike. Welcome to 141 West Street where one level luxury living, a private penthouse terrace, two garage parking spaces, and a walk-everywhere location come together to offer benefits that are difficult to duplicate anywhere else in downtown Annapolis.

141 West St Unit #401, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$299,900
2 Beds 2 Baths
Welcome to this fully renovated penthouse condo in the highly desirable Annapolis Overlook community. This spacious 2-bedroom, 2-bath residence features soaring 10-foot ceilings in the main living area, creating an airy, open feel filled with natural light, along with a cozy wood-burning fireplace perfect for cooler evenings. The thoughtfully designed open-concept layout flows seamlessly from the living and dining spaces to the covered balcony — protected on three sides for year-round enjoyment — while the incredible cross breeze throughout the home makes temperate months especially enjoyable indoors. Inside, nearly every surface has been updated with brand-new finishes, including luxury vinyl plank flooring, new carpet, new soft-close cabinetry, quartz countertops, stainless steel appliances, fresh paint, and fully renovated bathrooms. The spacious primary suite offers a walk-in closet and private en suite bath for added comfort and convenience. Residents of Greystone Court enjoy secured building entry, beautifully maintained common grounds and green space, a fantastic outdoor pool, fitness center, and abundant guest parking. The unit also includes two parking spaces — one assigned and one permit parking space. Ideally located with easy access to Downtown Annapolis, Washington D.C., and all major commuter routes, this home also places you moments from shopping, dining, and everyday conveniences. Modern, move-in ready, and perfectly located — this is condo living at its best.

40 Greystone Ct Unit #L, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767

$699,999
2 Beds 2 Baths
Step into sophisticated comfort in this exceptional third-floor corner residence, a 2024-built condominium offering 1,723 square feet of thoughtfully designed space filled with natural light and showcasing designer finishes, premium upgrades, and meticulous attention to detail throughout. Located within a desirable 55+ active adult community, the open, well-appointed floor plan includes two spacious bedrooms, two full baths, and a private study—perfect for today’s flexible lifestyle. The gourmet kitchen stands out with high-end appliances, upgraded cabinetry, and elegant finishes, ideal for both everyday living and entertaining. Freshly painted and professionally styled, the home features new designer lighting and custom closet systems for added sophistication and functionality. Step outside to a private balcony—perfect for enjoying warm summer days, morning coffee, or evening relaxation. A rare highlight is the combination of two highly sought-after features: a private storage unit, reserved garage parking, an uncommon offering that adds significant value. Enjoy the added benefit of a low condo fee, enhancing both affordability and long-term value. Residents enjoy resort-style amenities, including pickleball courts, scenic walking trails, a golf simulator, dog park, and inviting indoor and outdoor gathering spaces with grilling areas, all ideally located with a quick drive to downtown Annapolis, waterfront dining, shopping, and the Bay Bridge. Impeccably maintained and move-in ready, this residence offers a unique opportunity to own a beautifully upgraded home with exceptional parking and storage in a vibrant, amenity-rich community.

78 Old Mill Bottom Rd N Unit #311, Annapolis

Listing courtesy of RE/MAX Galaxy. Contact: 8888843396

$1,175,000
2 Beds 3 Baths
New Pricing ....Welcome to the heart of Annapolis and experience elegant downtown living at Acton’s Landing, just footsteps from the city’s vibrant waterfront, fine dining, shopping, and historic attractions. Perfectly positioned, this distinguished brick condominium building offers refined living with breathtaking views of the Maryland State Capitol and the Annapolis waterfront, placing the very best of the city right outside your front door. Step inside to a thoughtfully designed interior where custom crown molding throughout the main living space perfectly complements soaring 9‑foot ceilings. Recessed lighting, paired with abundant natural light, enhances the open and airy ambiance. Large windows and sliding glass doors frame stunning skyline views, creating a seamless connection between indoor and outdoor living. The chef’s kitchen features rich wood cabinetry, gleaming granite countertops, and generous space ideal for both everyday living and entertaining. The open floor plan flows effortlessly to a remarkable 800‑square‑foot terrace, offering multiple vantage points and adorned with thoughtfully placed flowers that create the feel of a private garden retreat. The primary suite offers a luxurious retreat with a spacious en‑suite bathroom featuring a soaking tub, separate shower, and elegant vanity. The guest suite is equally inviting, offering a private balcony—perfect for morning coffee or unwinding in the evening—along with a private bath featuring a granite vanity and walk‑in shower. Parking space and two storage units convey. Just steps from your front door, enjoy walkable access to the waterfront, fine dining, boutique shopping, and Annapolis’ historic landmarks, all while relishing the privacy and sophistication of Acton’s Landing. With premium finishes, expansive outdoor living spaces, breathtaking views, and an unbeatable downtown location, this exceptional residence captures the very essence of luxury Annapolis living.

66 Franklin St Unit #403, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: khylah.settle@cbmove.com

$309,900
2 Beds 2 Baths
Welcome to effortless living in one of Annapolis' most sought-after locations. With new systems like the **new price**Welcome to effortless living in one of Annapolis' most sought-after locations. With new systems like the efficient gas furnace and hot water heater, this well-maintained 2-bedroom, 2-bathroom condominium offers 1,065 square feet of comfortable living space with one standout feature that sets it apart: main-level access. In a building with no elevator, this ground-floor location means you'll never climb a single flight of stairs—ideal for those seeking accessibility and convenience. Step outside your front door onto a charming patio where you can enjoy your morning coffee or unwind after a day exploring everything Annapolis has to offer. This private outdoor space adds a welcoming touch to everyday living. The real magic lies in what's just beyond your doorstep. You're within walking distance or a short drive to the Annapolis Historic District, where cobblestone streets lead to the Maryland State House, boutique shops, and acclaimed restaurants. Stroll down to City Dock for waterfront dining and sailing culture, or catch a game at Navy-Marine Corps Memorial Stadium. The U.S. Naval Academy is practically in your backyard—making this an exceptional opportunity for parents of midshipmen seeking a convenient pied-à-terre during their student's four years at the Academy. Daily conveniences are equally close at hand: grocery stores, houses of worship, the hospital and easy transportation connections to Washington, D.C. for work or weekend adventures are here. With modest association fees and no-frills ownership, this condo delivers exceptional value in a location where proximity to history, culture, and community commands a premium. Whether you're downsizing, investing, or establishing a local home base, this main-level gem offers the freedom to live well in one of the Mid-Atlantic's most charming cities.

2001 Warners Ter N Unit #102, Annapolis

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

$569,000
2 Beds 2 Baths
AMENITY RICH LOCATION!!! Welcome to this beautiful 2 bedroom, 2 bath coveted, spacious and serene 2nd floor end unit condo, located in Second Village just steps away from all of the amenities found in Chesapeake Harbour. Imagine yourself enjoying the Bay front swimming pool, the sandy beach, kayaks, grills, picnic tables, fishing/crabbing piers, jog/walking paths, pickleball and tennis courts, and the EV charging station. Chesapeake Harbour is a gated community which provides a guarded 24-hour security entrance, has a private marina with available deep-water slips, direct bay access, and a gourmet restaurant with a waterfront tiki bar - all just minutes from downtown Annapolis. This spotless home offers the perfect blend of privacy, natural light, and lush greenery surrounding it on all sides. With a winter water view of Chesapeake Bay and Chase Pond from the kitchen’s center island, you can enjoy the additional square footage not found with interior units. The open floor plan is bathed in sunlight from floor to ceiling windows and invites the outside in. The living spaces are airy and inviting, with a seamless flow from the cozy living room to the dining area and updated kitchen, including hardwood and tiled floors, a fireplace for those cooler evenings, and a large wraparound deck, available only on end units, where relaxing or entertaining outside can be enjoyed. Whether you are a boating enthusiast, enjoy all the historical small-town charm that Annapolis offers, or simply crave the coastal lifestyle, this property checks all the boxes. Don’t miss your chance to own this one-of-a-kind retreat. Schedule your tour today and experience the perfect blend of adventure and relaxation that living in Chesapeake Harbour offers. Priced to make it your own.

2110 Chesapeake Harbour Dr Unit #101, Annapolis

Listing courtesy of Compass. Contact: (410) 429-7425

$499,999
2 Beds 2 Baths
This exceptional 5th-floor condo offers a one-of-a-kind, unique floor plan with breathtaking panoramic views and an abundance of natural light from its sunny southern exposure. Featuring two generously sized bedrooms with expansive closets, this upscale residence combines comfort and style. Inside, you’ll find beautiful hardwood floors, soaring 10-foot ceilings, and elegant granite countertops throughout. The freshly painted interiors are complemented by custom window treatments that add both privacy and sophistication. Step outside to your private balcony and enjoy sweeping views of the surrounding area. Key Features: 2 spacious bedrooms with large closets Gorgeous hardwood floors Soaring 10-ft ceilings for an open, airy feel Granite countertops in kitchen and baths Freshly painted with custom window treatments Private balcony with stunning views Assigned parking space for convenience Building Amenities: Rooftop pool with panoramic vistas State-of-the-art fitness center Elegant club rooms for gatherings and relaxation Concierge service for a luxurious living experience Ideally located in the vibrant Annapolis Towne Centre, this condo puts you within walking distance of premier shopping, dining, and entertainment options. Whether you're enjoying a meal at one of the area's finest restaurants or exploring local boutiques, everything you need is just moments away. This is a must-see home that blends modern living with the best of Annapolis! Don't miss out on the chance to call this spectacular property yours.

1915 Towne Centre Blvd Unit #502, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$520,000
2 Beds 2 Baths
Seller Says SELL!!! Welcome to penthouse living at Element at Mill Creek, one of Annapolis’ most stylish and thoughtfully designed 55+ communities. This 2 bed + Den, 2 bath top-floor residence with in-home laundry offers the privacy and quiet you’ll appreciate, paired with the elevated finishes and upgrades that truly make it better than new construction. From the moment you enter, you’ll notice the difference. Since purchasing, the owner has enhanced the home with carefully selected upgrades—refined lighting, custom touches, and elevated finishes that go beyond the builder’s base offerings. The result is a move-in-ready home with personality, warmth, and polish already in place. No waiting on construction timelines, no post-settlement projects—just effortless living from day one. This penthouse unit enjoys abundant natural light and peaceful views, along with the convenience of an assigned parking space in a secure garage—providing comfort and ease year-round. Life at Element at Mill Creek is designed for connection, wellness, and enjoyment. Residents enjoy a beautifully appointed clubhouse featuring indoor and outdoor dining spaces, a state-of-the-art fitness center, gathering rooms, and even a golf simulator for year-round play. Outdoors, you’ll find pickleball courts, scenic walking trails, and a dedicated dog park—perfect for staying active and social while enjoying the thoughtfully landscaped grounds. The community’s modern coastal architecture and easy layout create a fresh, welcoming neighborhood atmosphere that feels both intimate and sophisticated. Located just minutes from downtown Annapolis, you’ll have easy access to everything that makes the area so special—waterfront dining, boutique shopping, art galleries, live music, and year-round festivals. Spend afternoons strolling along City Dock, catching a sailboat race on the Chesapeake Bay, or enjoying dinner at one of the many acclaimed local restaurants. The charm, history, and vibrant lifestyle of Annapolis are right at your doorstep. And unlike many new construction purchases—where buyers are often responsible for the majority of closing costs—this resale offers a more traditional and balanced approach, with costs typically shared between buyer and seller. Title insurance discount also available. Stylish, upgraded, and ideally located, this penthouse at Element at Mill Creek offers the perfect blend of low-maintenance luxury, active living, and the best of Annapolis just moments away.

78 Old Mill Bottom Rd N Unit #409, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$1,379,000
2 Beds 3 Baths
Walk to everything !!! Less than 3 blocks to restaurants, marinas, water taxi, street end parks, brew pub, pools, museums and more. Downtown historic Annapolis is a short walk or water taxi ride !! You really don't even need a car !!! Incredible Opportunity in the Heart of Eastport! Beautifully updated 3-story Victorian located on the Eastport Peninsula. Features include off-street parking, a welcoming front porch (2000), Windows and roofs replaced (2025) including gutters w/gutter guards. Wood floors, and impressive chef’s kitchen with beautiful granite counters, Viking appliances (6-burner stove), and vented hood - all enhanced by a large skylight in the center of the kitchen and a captivating view into the enchanting backyard provided by a large 3 window slider. When you are inside this home you sense nature has joined you. Upper two levels offer space brought to life with a large skylight highlighting the 3rd floor bedroom w/remodeled bath. While the 2nd floor sports 3 skylights w/solar shades, small office/library, washer/dryer closet, Bedroom, and a remodeled bathroom. The detached structure introduces 2 additional large skylights w/solar shades, and lots of additional windows providing a bright and airy ambiance. Energy-efficient appliances, including a gas on-demand water heater (2020), fully encapsulated crawl space (2025), Flexible heating and cooling options with ornate radiator heat complimented by five mini-split units providing a total of 48,000 BTUs for heating and cooling (entire A/C system new 2025) - just enhance year-round comfort and efficiency & have earned this home an Energy Star Certificate from BGE The mesmerizing private & fully fenced backyard (new 2020) just calls to you! New rear porch (2024) and adjoining brick patio maneuver strategically around the mature native trees and lush landscaping. A very inviting & tranquil stage postured perfectly for relaxing and entertaining. The detached accessory structure offers endless possibilities: office, studio, hobby or game room, gym...or add a bathroom to create a charming 'casita'. And don't forget.....there is a bricked off street driveway !! This property is move-in ready—just bring your personal touch! Seller will consider all offers !!!

120 Chesapeake Ave, Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact: 4109724000

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