Annapolis Homes with Colonial Style

Annapolis Homes with Colonial Style

Welcome to Annapolis, Maryland—a city that beautifully marries history with modern living. Nestled along the picturesque shores of the Chesapeake Bay, Annapolis is not only the state capital but also a vibrant hub of culture and charm. Known for its rich maritime heritage, this enchanting city boasts a stunning waterfront, historic landmarks, and a thriving arts scene. Whether you’re strolling through the cobblestone streets of the historic district or enjoying a meal at one of the many waterfront restaurants, Annapolis offers a unique blend of small-town warmth and urban sophistication.

One of the most appealing aspects of living in Annapolis is the array of stunning homes, particularly those showcasing the timeless elegance of Colonial architecture. These homes often feature classic brick facades, symmetrical designs, and charming details that harken back to the city’s colonial roots. With spacious layouts, large windows, and inviting front porches, Colonial-style homes in Annapolis are perfect for families and individuals who appreciate both history and comfort.

Living in a Colonial-style home in Annapolis means more than just enjoying beautiful architecture; it’s about becoming part of a community that values tradition, culture, and a strong sense of place. With access to top-rated schools, lush parks, and a plethora of recreational activities, it’s no wonder that Annapolis is a sought-after destination for homebuyers. Experience the charm and allure of this historic city, where your dream home awaits amidst the captivating backdrop of Maryland’s capital.

Newest Annapolis Homes with Colonial Style

3 Beds ⋅ 4 Baths

Welcome to this beautiful and thoughtfully updated townhome in the sought-after community of Windgate! Offering 3 spacious bedrooms, 2 full and 2 half baths, a 1-car garage, three finished levels, and a desirable bump-out, this home combines comfort, style, and convenience. The remodeled eat-in kitchen features crisp white cabinetry, granite countertops, stainless steel appliances, gas cooking, and a bright breakfast area. The adjoining dining area opens to a large rear deck—perfect for grilling, entertaining, or simply relaxing. Plantation shutters, numerous built-ins, and beautifully upgraded flooring throughout add even more character and appeal, including engineered hardwood, luxury vinyl tile, ceramic tile, and carpet. Upstairs you'll find three generously sized bedrooms, including a spacious primary suite featuring vaulted ceilings and a large walk-in closet. The finished lower level provides even more living space with a large recreation room, half bath, and walk-out access to the patio and fully fenced backyard. This home has been exceptionally well maintained with numerous recent improvements, including a NEW HVAC system, hot water heater, kitchen appliances, and flooring in 2023; NEW garage door and openers in 2025; plus a roof installed in 2019 with 50-year shingles—providing added peace of mind for the next owner. Location is another standout! Enjoy convenient access to Downtown Annapolis, the U.S. Naval Academy, Annapolis Mall, Anne Arundel Medical Center, and an incredible selection of restaurants, shopping, entertainment, and everyday conveniences. Commuters will appreciate the easy access to major routes connecting Annapolis, the Eastern Shore, Washington, D.C., and Baltimore. Beautifully updated, spacious, and ideally located—this wonderful Windgate townhome is ready to welcome its next owner!

706 Howards Loop, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

3 Beds ⋅ 2 Baths

Nestled in the charming Pendennis Mount community, this delightful Colonial home offers a perfect blend of comfort and convenience. Built in 1953, this well-maintained residence features three spacious bedrooms and one and a half bathrooms, making it an ideal retreat for those seeking a cozy atmosphere. Stairs lead to the attic where an insulated area is complete with built-in book shelves. This area was used as a study and office. A large screened in porch off the kitchen is perfect for outdoor dining. The property boasts a generous 0.27-acre lot, providing ample outdoor space for relaxation and recreation. With direct access to the Severn River, residents can enjoy a variety of water activities, including kayaking, fishing, and boating, all just steps from home. The community dock enhances the experience, allowing for easy access to the river's beauty. Membership in the boat club is available. The inviting interior features a warm fireplace, perfect for cozy evenings, while the basement offers additional space with garage access and a walkout level, ideal for storage. The attached garage and driveway provide convenient parking options. Pendennis Mount is not just about the home; it's about the lifestyle. The neighborhood is well-connected, with downtown a mile away making commuting a breeze. Jonas Park offer green spaces for outdoor activities, and local schools are known for their commitment to education and community involvement. Experience the charm of this vibrant community, where the beauty of nature meets the comforts of home. This property is more than just a house; it's a place to create lasting memories.

8 Brice Rd, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

2 Beds ⋅ 2 Baths

Original owner. Well maintained ground level 2-bedroom, 2-bathroom condo. Stainless steel appliances, ceramic tile backsplash, granite counter tops, crown molding, and recessed lights Carpet, and hot water heater installed in 2025. HVAC installed 2019. Refrigerator installed in 2024. Hardwood floors in living room and ceramic tile in bathrooms. Dual sinks in master bathroom. Large walk-in closets and storage space. Walk out to rear parking. Minutes away from multiple shopping centers, banks, dry cleaners, restaurants, hardware store and gas stations. Community amenities have a club house, gym, pool, library and newly installed 3 car electric car chargers. A must see to believe. Set up showing and bring us an offer.

1503 Broadneck Pl Unit #101, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

4 Beds ⋅ 3 Baths

Welcome to Heritage, a sought-after Annapolis community where space, comfort, and convenience come together! This beautifully refreshed three-level Colonial offers four bedrooms, multiple living spaces, a huge fully fenced backyard, and an impressive list of recent updates—making it truly move-in ready. Step inside to fresh paint, new carpet and LVP flooring, updated fixtures and hardware, and a bright, welcoming layout designed for everyday living and entertaining. The updated kitchen features freshly painted cabinetry and a brand-new refrigerator and opens to the family room for an easy, connected flow. Formal living and dining rooms provide additional space to gather, while the fully enclosed sunroom with casement windows offers a wonderful spot to relax and enjoy views of the backyard. A convenient half bath and mudroom with laundry hookups complete the main level. Upstairs, you’ll find four generously sized bedrooms. The spacious primary bedroom features two closets, while the second and third bedrooms share a Jack-and-Jill bath with a brand-new shower. An additional full hall bath adds even more flexibility for busy mornings and overnight guests. The lower level expands your living space with a partially finished recreation room featuring new drywall and recessed lighting—ready for movie nights, a game room, home gym, office, or whatever suits your lifestyle. A large storage and utility room includes additional laundry facilities, and a waterproofing system installed in 2023 comes with a lifetime warranty for added peace of mind. Outside, the expansive fully fenced backyard is ready for entertaining, gardening, play, or simply enjoying more room to spread out. A composite deck and storage shed add even more functionality. Additional improvements include replacement windows and a roof replaced within approximately the last 10 years. And then there’s the location! Heritage residents enjoy access to community amenities including a pool, clubhouse, fields, and a footbridge over Spa Creek—all while being conveniently located near the shops, restaurants, waterfront, and unmistakable charm of Downtown Annapolis. With its generous space, extensive updates, fantastic backyard, and Annapolis location, this is a home you’ll want to experience in person. Welcome home!

402 South Cherry Grove, Annapolis

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

4 Beds ⋅ 3 Baths

This charming Colonial-style home in the desirable Riva Trace community offers a perfect blend of comfort and convenience. Set on a spacious 0.27-acre lot, the well-maintained yard features a side yard and a rear yard with an inground pool, ideal for gardening or entertaining. Inside, the home boasts four bedrooms and two and a half bathrooms, providing ample space for relaxation. The cozy family room is enhanced by a fireplace with glass doors, perfect for creating a warm ambiance during cooler months. The family room also leads to an enclosed porch that also leads to the pool and rear yard. The unfinished basement with a walkout entrance offers potential for customization, whether for additional living space or storage. Enjoy the luxury of a personal pool, perfect for summer gatherings or quiet afternoons. The property is conveniently located near Ginger View Creek, offering a tranquil water feature for nature enthusiasts. Riva Trace is known for its strong community spirit, with nearby parks and recreational facilities that promote an active lifestyle. Residents benefit from access to quality schools and essential public services, ensuring a well-rounded living experience. With easy access to local amenities and a welcoming neighborhood atmosphere, this home is a fantastic opportunity for those seeking a vibrant community. This is the Cardiff model with many wonderful features. The price reflects TLC needed.

236 Autumn Dr, Annapolis

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

5 Beds ⋅ 4 Baths

Turn key and thoughtfully updated, this 5-bedroom, 4.5-bath single-family home offers a rare combination of spacious living, modern upgrades, and resort-style outdoor amenities in Annapolis. This impressive property features an attached two-car garage, a private in-ground pool, and a pool house. In addition, there is a rear entry apartment with its own private deck. The spacious main residence offers five bedrooms and four-and-a-half bathrooms with comfortable living areas throughout. The beautifully renovated kitchen is designed for both everyday living and entertaining, featuring granite countertops, stainless steel appliances, brand-new Bosch appliances and new flooring. In addition, the home has been thoughtfully upgraded with a new gas furnace and a newly completed fully finished basement with a bedroom and full bath (completed just two months ago) providing additional space for recreation, guests, a media room, or flex space. Adding even more space, the separate apartment, with its own rear entry, provides exceptional flexibility for extended family, guests or potential rental opportunities. Step outside to enjoy your own private backyard oasis featuring an in-ground pool and pool house, perfect for entertaining, relaxing, and enjoying the Annapolis lifestyle. Also, the Arundel Olympic Swim Center, Anne Arundel County’s largest public year-round indoor swimming facility, is across the street. There is also a 1.5 mile running trail nearby along with all the tennis courts and track at Annapolis High School, all open to the public after school hours. Conveniently located near downtown Annapolis, waterfront dining, shopping, parks, and major commuter routes including US-50 and MD-2, this remarkable property offers the perfect blend of comfort, convenience, and versatility. Mortgage savings may be available for buyers of this listing.

112 Speicher Dr, Annapolis

Listing courtesy of Redfin Corp. Contact: 4102028454

4 Beds ⋅ 5 Baths

This beautifully updated Colonial offers the perfect blend of comfort, space, and functionality. Featuring four bedrooms, three full and two half baths, this home is designed for both everyday living and effortless entertaining. Relax on the inviting covered front porch, unwind on the screened porch, soak in the 10-person hot tub, or gather around the newly built fire pit with its custom paver patio in the level, fenced backyard. Inside, you'll find hardwood floors, luxury vinyl plank flooring, new carpet upstairs, recessed lighting throughout, and a warm family room with a wood-burning fireplace. The thoughtfully designed floor plan includes a mudroom and the convenience of two laundry areas, including one in the primary suite. The finished lower level, with its private entrance, offers exceptional flexibility with a large recreation room, kitchenette, full bath, and bonus room—ideal for guests, multigenerational living, a home office, or hobby space. Recent updates include most windows and a two-zone HVAC system installed in 2024. Storage is plentiful with a spacious crawl space beneath the addition and a two-car garage featuring a floored attic, shelving, cabinets, pegboard, and pull-down stairs. An extra-wide driveway provides plenty of room for an RV, boat, or additional vehicles. Located in the water-oriented community of Annapolis Roads, residents enjoy community water access, a sandy beach, boat ramp, picnic area, and playground, all just minutes from Downtown Annapolis, Route 50, shopping, and dining. Harbor Drive is a private road maintained by the Annapolis Roads Property Owners Association (ARPOA). No HOA. Home warranty with Choice good through 2030 conveys to buyer.

1007 Harbor Dr, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact: 4102669005

3 Beds ⋅ 4 Baths

Welcome to this beautifully maintained brick-front townhome in the desirable August Woods community, offering three finished levels of light-filled living space in an unbeatable Annapolis location just minutes from downtown. The open-concept main level features 9-foot ceilings, crown molding, a cozy gas fireplace, and a spacious eat-in kitchen with granite countertops, a center island, premium Wolf appliances, and a gas range. The bright sunroom opens to a large deck overlooking a private wooded backdrop and a fully fenced turf backyard—perfect for relaxing or entertaining. Upstairs, the spacious primary suite offers a walk-in closet and a spa-inspired bath with a Jacuzzi tub, separate shower, and double vanity. Two additional bedrooms, a full bath, and an upper-level laundry complete the second floor. The walkout lower level provides flexible space for a recreation room, home office, or gym, along with a half bath and extra storage. Recent updates include a turf backyard(2023), HVAC system (2023), hot water heater (2024), and Tesla EV charger (2024). The home also features a MyQ smart garage door, Nest thermostat, smart lock, built-in ADT security system, and an oversized one-car garage with additional storage. Residents enjoy convenient access to downtown Annapolis, the Chesapeake Bay, shopping, dining, parks, boat launches, playgrounds, Pip Moyer Recreation Center, and one of Annapolis’ most popular outdoor pool complexes. This move-in-ready home combines quality finishes, modern upgrades, and an exceptional location.

1151 August Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

2 Beds ⋅ 2 Baths

Welcome to this beautifully updated and move-in-ready home! The bright and inviting main level features stunning wood floors (2025) and flows seamlessly into a fully remodeled kitchen (2025). The kitchen boasts crisp white cabinetry, stainless steel appliances, quartz countertops, peninsula featuring a striking quartz waterfall countertop with a sleek flat cooktop, and new smart inset ceiling lights. Two large newly added windows in the kitchen add natural light. The adjacent dining room is highlighted by a new smart chandelier and upgraded French doors (2025). Upstairs, you will find two generously sized bedrooms. The entirely remodeled full bathroom (2026) serves as a luxurious retreat, showcasing a large glass walk-in shower with custom tile work and a modern rainfall showerhead. Smart inset ceiling speakers in this space pair to your cell phone for easy listening opportunities, while a contemporary front lit and anti-fog mirror sits above a burnished stone floating vanity. The basement offers a spacious finished living area alongside an unfinished utility/laundry space, a workbench with built-in shelving, and a convenient half bathroom. It is further enhanced by newly added ceiling insulation (2026). The house features many updates including windows throughout the home (2023), roof with a 30 year warranty (2020), fully refreshed exterior paint (2023), and added windows to both the bathroom and kitchen to increase natural light. Outdoor entertaining is a dream with the covered deck located right off the dining room, leading down to a beautifully landscaped yard complete with a shed for storage, brick lined gravel path, and two gorgeous wooden pergolas.

422 Blossom Tree Dr, Annapolis

Listing courtesy of Samson Properties. Contact: 7033493900

5 Beds ⋅ 5 Baths

Welcome to this beautifully maintained custom built Tudor Style home in this small coastal community! NO HOA!! Pride of ownership shows! With a primary suite on the main level and another primary suite on the upper level, this home is perfect for multi-generational living and accessibility! The upper level features 3 spacious bedrooms and 2 full baths; the main level has 1 large bedroom with a full bath and walk-in shower; and the lower level has another full bath and several areas to make additional bedrooms. The huge 1,100 sqft finished lower level has multiple rooms including a large rec room that can fit a pool table, games and a bar area; plus a family room or theatre room and private entrance! There is even space for a kitchenette! There are so many possibilities with this extra space including an apartment or in-law suite! The home is filled with natural light and scenic views throughout. Situated on almost a half of acre and only 2 blocks to the Chesapeake Bay! The lush backyard is fully fenced in and ready for summertime entertaining! The lot next to the home is a preserved wooded lot that offers privacy and attracts wildlife. Oyster Harbor offers the best of Coastal Maryland living—just minutes from historic downtown Annapolis, top-rated restaurants, shopping, and commuter routes. The home has been well cared for and maintained; only two owners since it was built! Recent updates include: HVAC, water heater, main level LVP floors that are very durable, trex deck and renovated front porch with tile, custom plantation shutters, renovated primary suite and luxury full bath, front load w/d, professionally cleaned, professionally landscaped, backyard drainage system...and more! Sellers are MOTIVATED and ready for another family to make this their home! MOVE-IN READY AND A MUST-SEE! You won't find many homes with this lot size and location for this price. Schedule your showing today! OPEN HOUSE SUN 1-3PM!

3280 Arundel On The Bay Rd, Annapolis

Listing courtesy of The KW Collective. Contact: 4435741600

5 Beds ⋅ 2 Baths

A truly extraordinary opportunity awaits in one of Annapolis' most coveted waterfront locations. Situated in the historic Ferry Farms neighborhood, 1979 Baltimore Annapolis Boulevard is one of only thirteen homes positioned directly across the Severn River from the U.S. Naval Academy, offering uninterrupted panoramic views that have captivated generations. Imagine enjoying the Blue Angels soaring overhead each May from your own front lawn or dock—an experience few will ever call home. Rich in architectural character, the residence showcases the craftsmanship and charm of its era, including original hardwood floors, a classic wood-burning fireplace, vintage kitchen, inviting sunroom, screened porch, and period details that create a warm sense of history. The home's generous square footage spans three levels, blending the original residence with a substantial 2015 addition that expanded both its living space and functionality while preserving its unique personality. For buyers with vision, this property presents an exceptional opportunity to create a landmark waterfront residence tailored to today's lifestyle. Architectural renderings, renovation plans, a professional landscape design, and contractor cost estimates are available to help bring that vision to life, allowing the next owner to build upon an already remarkable foundation. The original home includes a main-level bedroom and full bath, while the upper level offers four additional bedrooms, including a primary suite with a private balcony overlooking the water. The 2015 addition introduced a spacious three-car garage, an expansive loft, and an additional bedroom perfect for guests, a home office, or a studio. A future bathroom has already been considered, with a rough-in located beneath the connecting section of the second floor. The lower level offers even more possibilities, featuring a second wood-burning fireplace, laundry area, utility space, and an impressive workshop with soaring ceilings and direct access to the garage and backyard—ideal for craftspeople, hobbyists, or future finished living space. Outside, the waterfront amenities are equally compelling. The private deep-water pier and bulkhead, completed in 2003, feature approximately 10 feet of water depth, a 40,000-pound boat lift, a 15,000-pound lift, and two 1,500-pound personal watercraft lifts, making this an outstanding property for serious boaters. A built-in outdoor barbecue and expansive waterfront setting invite effortless entertaining and relaxed evenings watching sailboats drift past the Academy. Properties of this caliber, location, and potential rarely become available. Whether thoughtfully restoring its historic character, executing the available renovation plans, or creating a legacy waterfront estate of your own design, this is a once-in-a-generation opportunity to own an irreplaceable piece of Annapolis waterfront in one of its most prestigious and tightly held neighborhoods.

1979 Baltimore Annapolis Blvd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

4 Beds ⋅ 4 Baths

Welcome to 810 Moran Drive, a beautifully updated home in the highly desirable Monticello community, offering over 3,900 finished square feet of thoughtfully designed living space in one of Annapolis' most convenient locations. Just minutes from Historic Downtown Annapolis, the Naval Academy, shopping, dining, commuter routes, and waterfront attractions, this home perfectly blends comfort, style, and location. Backing to mature trees and neighborhood walking trails, the private backyard provides a peaceful setting to relax or entertain. Enjoy outdoor living on the spacious deck with a recently reinforced structural beam and updated trim (2026), gather around the natural gas outdoor fireplace, or fire up the included Big Green Egg and grill. Inside, you'll find freshly sanded and stained hardwood floors with new boards, updated railings, and stylish lighting fixtures throughout. The heart of the home is the beautifully renovated kitchen, featuring custom cabinetry installed approximately one year ago, generous workspace, and an ideal layout for everyday living and entertaining. The main level offers a dedicated home office, spacious living and dining areas, and a convenient powder room. Upstairs, you'll find four generously sized bedrooms, three full bathrooms, and a well-appointed laundry room, including a spacious primary suite designed for comfort and privacy. The finished lower level adds approximately 700 square feet of additional living space, while still providing ample unfinished storage. Plumbing has already been roughed in for a future bathroom, offering flexibility to create an additional bedroom, guest suite, or recreation space. Additional updates and features include a new HVAC air handler (2019), roof installed in 2010, updated fencing, natural gas fireplaces inside and out, and access to Monticello's sought-after community amenities, including a neighborhood pool and scenic walking trails. This move-in-ready home combines generous living space, quality updates, and an unbeatable Annapolis location—an exceptional opportunity you won't want to miss!

810 Moran Dr, Annapolis

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

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