Annapolis Historical Real Estate

New price! Welcome to 108 Maple Drive, a beautifully updated rancher in the sought-after waterfront community of Hillsmere Shores. Renovated throughout in 2016, this move-in ready home offers 3 bedrooms, 3 full baths, and the convenience of single-level living in one of Annapolis' most beloved neighborhoods. Inside, you'll find updated finishes, an inviting floor plan, and comfortable living spaces designed for everyday living and entertaining alike. Step outside to enjoy the screened porch overlooking a fully fenced backyard, complete with a large storage shed and plenty of room for pets, play, gardening, or gatherings with family and friends. A spacious driveway provides abundant off-street parking for multiple vehicles, boats, or trailers. Living in Hillsmere Shores means much more than owning a home—it’s a lifestyle. Residents enjoy access to a private marina with South River access, a community pool (additional membership), sandy beach, waterfront pavilions, playgrounds, kayak launches, and boat ramps. The neighborhood is also adjacent to Quiet Waters Park and just minutes from downtown Annapolis, shopping, dining, and commuter routes. Whether you're looking for your first home, your forever home, or the perfect place to enjoy Annapolis waterfront living, 108 Maple Drive offers an incredible opportunity at $699,900.

108 Maple Dr, Annapolis

Listing courtesy of Next Step Realty, LLC.. Contact: 4439012200

$1,099,000

Nestled in the heart of downtown Annapolis in the highly sought-after neighborhood of Murray Hill, this charming Colonial, originally built in 1925 and extensively remodeled in 2016, offers the perfect blend of historic character with modern updates, and an unmatched in-town waterfront lifestyle. Just one block from Spa Creek and Acton's Landing Waterfront Park & seasonal water taxi service, as well as a short stroll to Annapolis' renowned restaurants, shops, and cultural attractions. A picturesque front porch welcomes you and your guests and provides the perfect perch for morning coffee, evening cocktails, or simply watching the neighbors stroll by. Enter into a lovely living room with gleaming hardwoods anchored with a gorgeous gas fireplace. The open floor plan provides easy flow into the gorgeous chef's kitchen featuring a huge granite island, GE Café stainless steel appliances, a charming butler's pantry, and a half bath. Enjoy a private enclosed patio with ample space for a dining table, grill, and comfortable seating area—ideal for dining al fresco and entertaining guests. The second floor offers two bedrooms, a full bath, and a spacious landing perfectly suited for a home office, reading nook, or flex space. The third-floor primary suite serves as a private retreat with large windows, abundant natural light, and a Juliet balcony overlooking the neighborhood. A brand-new ductless mini-split system is being installed to serve the third-floor suite. Additional updates include a new furnace in 2023. Heating is provided by a combination of oil heat and heat pump, while natural gas serves the fireplace and hot water heater. The large unfinished basement provides laundry, mechanicals, and exceptional storage space. Additional conveyances include an interior fire sprinkler system, exterior irrigation system, two wine coolers, and five wall-mounted smart TVs. ATTENTION VA BUYERS: this home has an ASSUMABLE VA 2.37% interest rate- a very nice option in this 6+% mortgage interest environment! All in all 20 Shaw offers a rare opportunity to own a beautifully updated historic home in one of the city's most beloved neighborhoods, just a stone's throw to a wonderful waterfront park, as well as Annapolis' best restaurants & shops - downtown living at its finest!

20 Shaw St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$525,000

4 Beds ⋅ 3 Baths

Welcome home to this four bedroom, three full bath, rancher in Cape St Clarie in sought after Cape St Claire. Walk in to living room where the beautiful hardwood floors have juste been refinished. A great vaulted ceiling spans the kitchen and dining area combo with ceramic tile, stainless appliances, and a slider leading to the private backyard. The primary bedroom also has a vaulted ceiling, along with an attached full bath, hardwood floor, and walk in closet. Refinished hardwood flooring in the other three main level bedrooms and they share the hall full bath. Down the stairs walk into a huge rec room with plenty of room to spread out. Another full bath is tucked away downstairs, along with a very big laundry room and ample sized storage room. The backyard is fully fenced, and the back gate opens to a path which leads to the elementary school fields. *********Cape St Claire amenities include, beaches, fishing/crabbing pier, boat ramp, playgrounds, marina, & more. Broadneck School District. Close to shops and restaurants. Mins from Downtown Annapolis, and easy access for commuter routes to Washington, Baltimore, and close to Ft Meade. Great location, minutes from downtown Annapolis, and good commuter location with quick access to Rt 50 & I-97 close to Washington or Baltimore***BE SURE TO CHECK OUT THE VIRTUAL FLOOR PLAN TOUR

1248 Hilltop Dr, Annapolis

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

$539,900

3 Level Colonial Brimming with Classic Charm and Timeless Character. This Home Features a Welcoming Covered Front Porch, Perfect for Relaxing and Enjoying the Neighborhood Setting. Inside, you’ll Find Spacious Bedrooms and Hardwood Floors that Add Warmth and Potential Throughout. This Property is Ready for a Full Renovation, Offering an Incredible Opportunity for Investors, Builders or Buyers Looking to Restore and Customize a Classic Colonial to its Former Glory. With Vision and Updates, this Home can be Transformed into a Stunning Showcase Property. Ideally Located in Annapolis, this Home Offers Convenient Access to Downtown Annapolis, United States Naval Academy, and the Scenic Chesapeake Bay. Enjoy Nearby Shopping, Dining, Parks, and Waterfront Activities, along with Easy Commuter Routes to Baltimore and DC. A Fantastic Location Combining Historic Charm, Coastal Lifestyle, and Everyday Convenience. Sold As-Is

40 Munroe Ct, Annapolis

Listing courtesy of ANR Realty, LLC. Contact: 8773284400

$600,000

Welcome home to this thoughtfully redesigned home in Eastport just blocks from Spa Creek and minutes to downtown Annapolis. This beautifully updated 3-bedroom, 3-bath residence offers approximately 1,600 finished square feet across two levels, combining a functional layout with quality finishes and extensive upgrades throughout. The main level features a bright living room and an updated kitchen with quartz countertops, shaker cabinetry, stainless steel appliances, and a dining area. A main-level bedroom and full bath provide flexibility for guests or a home office. A dedicated laundry and utility space leads to the rear addition, where the private primary suite includes vaulted ceilings, a walk-in closet, and an en-suite bath with double vanities, custom tile, and a walk-in shower. The upper level offers a finished attic suite with a third bedroom, full bath, and bonus flex space suitable for an office or additional living area. Interior features include durable flooring, recessed lighting, and a cohesive, modern design. Exterior highlights include a fully fenced backyard with new sod and a concrete patio, ideal for outdoor enjoyment. The property also features professional landscaping, a new asphalt driveway for off-street parking, and durable exterior materials including Hardie Plank siding, Andersen 200 Series windows, and a new architectural shingle roof. Major system upgrades include 200-amp electric service, new plumbing, dual-zone HVAC, and a whole-house sprinkler system. Conveniently located near restaurants, marinas, parks, downtown Annapolis, and Truxton Park.

1210 President St, Annapolis

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

$1,295,000

OPEN HOUSE this SATURDAY 12-2PM and SUNDAY 10AM - 12PM. Now offered at an exceptional value in today's market. One of the most stunning renovations to come on the market in Downtown Annapolis! Perfectly blending historic charm with sophisticated modern luxury, this completely reimagined home is ideally situated on prestigious College Avenue in the heart of the Historic District and has been renovated from top to bottom with exceptional craftsmanship and designer finishes throughout. Step inside to discover gorgeous Forestall Montrose 7½-inch white oak hardwood flooring flowing throughout the home, complemented by abundant natural light and thoughtfully curated details at every turn. The show-stopping gourmet kitchen features Calacatta Goldlight quartz countertops, premium KitchenAid appliances including a 5-burner gas range, built-in oven, built-in microwave/air fryer, dishwasher, refrigerator, and a dedicated wine refrigerator—creating the perfect space for entertaining and everyday living. The luxurious bathrooms showcase imported Amira Moroccan Flair tile from Spain, elegant Merola Floral Garden tile accents, Kohler brushed brass fixtures, and designer LED anti-fog dimmable mirrors with tempered glass. A beautiful Pottery Barn chandelier adds warmth and sophistication to the home’s timeless design. Beyond the stunning aesthetics, this home offers complete peace of mind with all-new plumbing and electrical systems, closed-cell insulation, and a high-efficiency Bosch 3-ton heat pump with supplemental gas furnace option for year-round comfort. The upper level also features a conveniently located laundry area, enhancing the home’s thoughtful design and effortless livability. Adding to the home’s functionality is a spacious, clean lower level offering exceptional storage space and flexibility for seasonal items, hobbies, or future customization. A true extension of the home’s living space, the beautifully landscaped private brick courtyard is a rare Downtown Annapolis treasure. Thoughtfully designed with lush gardens, vibrant seasonal blooms, and privacy fencing, this outdoor oasis offers the perfect setting for entertaining, a quiet morning coffee, or unwinding after a day on the water. Ideally situated, this exceptional residence offers a truly unmatched lifestyle. Leave your car behind and enjoy a short stroll to City Dock, Ego Alley, waterfront parks, award-winning restaurants, boutique shopping, coffee shops, galleries, and entertainment. Enjoy front-row access to the charm and energy of downtown Annapolis while being moments from United States Naval Academy, St. John’s College, marinas, yacht clubs, and endless waterfront activities. This is a rare opportunity to own a fully renovated historic home where timeless architecture meets modern luxury in one of Maryland’s most coveted and walkable locations. Every detail has been thoughtfully selected and expertly executed, creating a truly turnkey property unlike anything else on the market.

11 1/2 College Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$1,850,000

Rare mixed-use opportunity on Annapolis' premier commercial corridor. Positioned directly on West Street (MD Route 450), this versatile, income-producing building pairs a roughly 2,000 SF ground-floor showroom with two legal second-floor apartments and a substantial detached garage with workshop — all on a 12,428 SF lot with private parking for about six vehicles, a genuine premium on this corridor. The ground level is an open, high-visibility showroom with direct West Street frontage, well suited to retail, a gallery or design studio, professional offices, or a service business. Upstairs, two legal apartments (2BR/1BA each, per owner) deliver real live/work flexibility — one is currently configured as offices with a full kitchen. Run your business below and lease or occupy above, lease every component separately, or use the upper level as executive offices. The three-bay detached garage is a true standout: two overhead doors plus a rear man-door, its own heating system, and a wood stove for year-round use — conditioned workshop and storage that's nearly impossible to replicate in this location. Major systems are already addressed, with two newer HVAC units and a newer roof reducing near-term capital needs. Public water and sewer, 200+ amp electric service, and a Flood Zone X location (outside the Special Flood Hazard Area) round out a favorable operating profile. BCE (Business Corridor Enhancement) zoning supports a broad mix of commercial and residential uses, giving owner-operators, investors, and developers exceptional flexibility on one of Annapolis' busiest, highest-visibility corridors. Schedule your private tour today. Information deemed reliable but not guaranteed. Square footage, apartment legality, zoning uses, and systems to be independently verified by buyer.

1977 West St, Annapolis

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

$799,999

4 Beds ⋅ 3 Baths

Please note, there is a basement in this home. See pictures. Welcome to Winchester On The Severn. One of Annapolis's most established waterfront community's. This home provides mature landscaping with a canopy of lovely trees and bushes both in the front and rear yard. Covered front porch! You will be pleased to enter a spacious foyer. Main level bedroom with a full bath to the left. A few steps up to the open floor plan with spacious living room that feeds into the dining room. Be prepared to enjoy the screened porch off the dining room. A wonderful spot to relax and enjoy the back yard. The eat in kitchen is filled with light! Comfortable family room is complimented with a wood burning fireplace. And you can also walk out from the family room to the back yard! The basement is dry and has a new 2025 heat pump. The 3 additional bedrooms have fresh paint. The larger bedroom is en-suite. Ready to know about the neighborhood? Amenities include private beach on the Severn River, marina, boat ramp, multiple piers, dog beach, beach pavilion, and the Chase Creek swim club. Nearby is the B&A trail. You may not want to leave the home but if you do it is a short ride to Annapolis and all major routes. Welcome. Enjoy

1518 Winchester Rd, Annapolis

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

$375,000

Annapolis Living at Its Finest – Renovated, Charming & Ready to Impress! Location. Lifestyle. Value. This is the Annapolis opportunity you've been waiting for! Welcome home to this beautifully renovated and exceptionally charming ranch-style home tucked away in the sought-after Forest Villa community. Combining timeless character with today's modern updates, this move-in-ready gem delivers the perfect blend of comfort, convenience, and affordability in one of Maryland's most desirable waterfront cities. From the moment you arrive, you'll appreciate the inviting curb appeal and bright, sun-filled interior. Every detail has been thoughtfully refreshed, including a brand-new roof, new luxury flooring, fresh designer paint, updated lighting and fixtures, a completely renovated bathroom, and a stunning kitchen featuring all-new stainless steel appliances, including a gas range. The spacious floor plan offers 3 comfortable bedrooms and a beautifully updated full bath, creating a warm and welcoming space you'll be proud to call home. Natural light pours through the home, enhancing every room and creating an airy, cheerful atmosphere. Step outside to discover one of this property's standout features—a huge backyard offering endless possibilities. Host unforgettable summer barbecues, gather around a fire pit with friends, create your dream garden, or simply relax and enjoy your own private outdoor retreat. The location is truly unbeatable. Just minutes from United States Naval Academy, historic downtown Annapolis, world-class marinas, waterfront dining, boutique shopping, festivals, parks, and endless Chesapeake Bay adventures. Whether you're strolling along City Dock, enjoying fresh seafood on the water, or setting sail for the weekend, you'll love having the very best of Annapolis right at your fingertips. Commuters will appreciate quick access to Routes 50 and 97, making travel to Baltimore, Washington, and beyond remarkably convenient. Rarely does a fully renovated home in such a prime Annapolis location become available at this price point. Whether you're a first-time buyer, downsizing, or searching for the perfect investment opportunity, this home offers exceptional value and an unbeatable lifestyle. Don't just buy a home—embrace the Annapolis lifestyle. Schedule your private showing today and discover why this remarkable property won't stay on the market for long! Owner Occupants Offers will be prioritized, HUD's First Look Period Applies for the 1st 30 Days. Call for Details and to schedule and tour.

1808 Lincoln Dr, Annapolis

Listing courtesy of Metro Bay Realty. Contact: 4105623392

$2,950,000

4 Beds ⋅ 5 Baths

Perfectly positioned on one of the most coveted streets in Historic Annapolis, just steps from State Circle, the United States Naval Academy, City Dock, waterfront dining, boutiques, and yacht clubs, 238 King George Street offers a rare opportunity to own a completely reimagined luxury residence in the heart of Maryland’s capital city. Blending timeless historic charm with the modern conveniences today's discerning buyer expects, this exceptional home was extensively renovated and expanded in 2006–2007 and thoughtfully updated through 2025, including a new roof, HVAC systems, and water heater. Inside, four beautifully finished levels offer elegant living and entertaining spaces filled with natural light, custom millwork, rich hardwood flooring, high ceilings, and refined architectural details throughout. The gourmet kitchen opens seamlessly to inviting gathering spaces designed for both intimate evenings and large-scale entertaining, while the finished lower level with high ceilings and private walk-out entrance provides exceptional flexibility for guests, recreation, or a private office. The upper-level loft retreat offers additional living space ideal for guests, a studio, or a luxurious private sanctuary. Enjoy views of the iconic Naval Academy Chapel dome, a daily reminder of the unparalleled location and lifestyle this home affords. Rare off-street parking adds tremendous value and convenience, while the lock-and-leave nature of the property makes it ideal as a primary residence, weekend retreat, or executive pied-à-terre. Offered substantially furnished with only a few exclusions, this remarkable home provides the opportunity to move in and immediately begin enjoying the very best of Annapolis living. Luxury, history, walkability, and convenience converge at one of the city's most prestigious addresses.

238 King George St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$485,000

Fully renovated rancher with all required permits in highly desired neighborhood. Completely updated kitchen with 42" cabinets, quartz countertop, separate island and stainless steel appliances. Main level hardwood floor. Fully finished basement with 4th bedroom and full bathroom, plus huge family room. New siding. New roof. New windows. New gas furnace. New central AC. New HWH. New sump pump. New deck. Private back yard. House located on quiet street, close to major routs and shopping.

105 Rosecrest Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$825,000

Quintessential Eastport charm in this sought-after Lower Eastport location. A welcoming front porch invites you to enjoy the vibrant local lifestyle. Inside, the light-filled layout features a spacious kitchen with a breakfast bar, a dedicated dining area, a convenient mudroom side entrance, half bath, & first-floor laundry. The upper level offers two generously sized bedrooms and a full bath. Relax on the large, private screened-in back porch overlooking a huge, level backyard perfect for entertaining. A standout feature is the over-sized detached shed/barn equipped with mini split (Heat and AC), ideal for a workshop, home office, or studio. This move-in-ready home is steps away from marinas, street-end waterfront parks, shopping, dining, and downtown Annapolis.

418 Chesapeake Ave, Annapolis

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

$395,000

PRICE IMPROVEMENT! This is a great value! Prepare to fall in love with this totally renovated gem! A complete and tasteful remodel has just been completed for the lucky new owners. Stunning LPV flooring, a beautiful gourmet kitchen with granite counters and new Stainless Steel Appliances, a fully remodeled bath and great details like new contemporary closet doors await the new owners.. The exterior has been refreshed for great curb appeal with the same attention to detail as the interior from new house numbers to planted window boxes to a charming new mailbox and freshly painted retaining wall. Walk into the warm and welcoming sunroom which leads to the open floor plan living room and dining room. The expansive rear deck and huge fenced yard are perfect for outdoor activities and entertaining. The unfinished lower level provides storage. Huge lot provides room for future expansion! Add the off street parking and you have everything you need at a great price!

1226 Tyler Ave, Annapolis

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

$430,000

Nestled in the highly sought-after Hillsmere community—one of Annapolis' premier waterfront neighborhoods—this charming home offers access to an exceptional array of amenities, including a private beach, boat ramp, community pool, playground, and more. This 3-bedroom, 1.5-bath residence features a full, partially finished basement, a spacious screened porch perfect for relaxing or entertaining, ample off-street parking, and a beautifully landscaped, fenced yard with mature trees and plantings. Enjoy the best of coastal living in one of the area's most desirable communities.

406 Holly Dr, Annapolis

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$1,699,900

6 Beds ⋅ 5 Baths

**Price Improvement!** Now offered at **$1,699,900**. Take another look at 87 Shipwright Street. In addition to the significant price reduction, several important improvements have recently been completed. The roof has been inspected and minor repairs have been made. The kitchen floor has been repaired, eliminating the previous sag, and the crawlspace has been professionally remediated, creating a clean, dry space. This spacious home offers a flexible floor plan, generous living space, and convenient access to downtown Annapolis, the waterfront, shopping, dining, and commuter routes. With recent improvements already completed and a new price, this is an excellent opportunity to own this exceptional Annapolis home.

87 Shipwright St, Annapolis

Listing courtesy of RE/MAX Executive. Contact:

$635,000

Welcome to 100 Carroll Drive, a fully remodeled four-bedroom, two-bath split foyer in the desirable and sought-after waterfront community of Hillsmere Shores in Annapolis. The upper level features a completely renovated open-concept layout with a stunning kitchen showcasing new cabinetry, new appliances, countertops, and luxury vinyl flooring throughout, flowing seamlessly into the dining and living areas—perfect for everyday living and entertaining. Just off the living room, enjoy an enclosed deck that adds extra flexible space and a great place to relax or entertain. This level also includes three spacious bedrooms and an updated full bathroom. Downstairs, the home continues to impress with tiled flooring throughout, heated floors, and a large primary suite with a private full bathroom, plus walkout access to an enclosed patio featuring a heated exercise pool or hot tub. Outside, the property offers a large cleared lot with beautiful landscaping, an irrigation system, and a shed for additional storage. Hillsmere Shores is known for its exceptional community amenities including a marina, multiple boat ramps and kayak launches, a beach, playground, and access to Quiet Waters Park, with the Key School conveniently located right across the street. An electric vehicle charger is also included, adding even more value and convenience—this move-in ready home is a rare opportunity to enjoy a renovated property and an unmatched Annapolis lifestyle.

100 Carroll Dr, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

$980,000

Don't MISS this RARE OPPORTUNITY IN THE VERY POPULAR COMMUNITY OF BAY RIDGE. .7460 Acres ! Make this PROPERTY Your Own! USE YOUR IMAGINATION! THE BAY RIDGE LIFESTYLE IS UNMATCHED IN ALL OF MARYLAND! SUPERIOR WATER ACCESS, STEPS TO COMMUNITY POOL/CLUBHOUSE W/ WATERCRAFT STORAGE RACKS , PRIVATE COMMUNITY BEACHES! & THE BIG WOODS "BAY RIDGE CONSERVATION AREA” W/TRAILS AND ACCESS TO BLACKWALNUT CREEK, A TRUE GEM! WALK TO COMMUNITY MARINA, PLAYGROUND, BASKETBALL/PICKEL BALL COURT, KAYAK RACKS , KASS PARK w/ BASEBALL/SOCCER, LACROSSE FIELD!! WHETHER YOU'RE A BOATER, SUP ENTHUSIAST, DOG WALKER, HIKER (PRIVATE TRAILS IN THE BIG WOODS), RUNNER, THIS NEIGHBORHOOD HAS IT ALL! JOINING THE BAY RIDGE CIVIC ASSOCIATION IS VOLUNTARY. SOLD STRICTLY AS IS.

54 Decatur Ave, Annapolis

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

$825,000

Welcome home to this one of a kind three bedroom, two and a half bath rancher on a double lot in sought after Cape St Claire. One level living at it's finest, with a huge sunroom with vaulted ceiling on one wing, and the bedrooms on the other wing of this sprawling rancher. This property has been lovingly maintained by the owners, with the addition of the sunroom, powder room, laundry room, and part of the garage in more recent years. The 600 square foot light filled sunroom is the focal point of the house now, with wonderful built in bookshelves and entertainment center. The original family room has a wood burning fireplace, and makes a cozy den or office. Stainless appliances and table space in the kitchen with French doors leading to the stone patio out back. The living room and dining room have ample space for gatherings. In the bedroom wing of the house find the primary bedroom with an attached full bath and two more ample bedrooms share the hall full bath. Recent updates include; July 2026 both the second zone HVAC & the water heater were replacedi, 2020 - Fast Care Floor System installed in garage & driveway resurfaced, in 2023 a new roof, in 2025 new HVAC first zone, new well pump, updated electric to code, new stainless steel liner in fireplace , & new oil tank, and in 2026 - new faucets in kitchen and master bath ****** Cape St Claire amenities include, beaches, fishing/crabbing pier, boat ramp, playgrounds, marina, & more. Broadneck School District. Close to shops and restaurants. Mins from Downtown Annapolis, and easy access for commuter routes to Washington, Baltimore, and close to Ft Meade. Great location, minutes from downtown Annapolis, and good commuter location with quick access to Rt 50 & I-97 close to Washington or Baltimore

1047 Little Magothy Vw, Annapolis

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

$635,000

2 Beds ⋅ 1 Baths

Great Opportunity! Prime Location!! Bring your ideas and imagination and transform this Eastport home into a gem! The current floorplan is 2 bedrooms and 1 bath with large living room, formal dining room, kitchen with oversized pantry... plus a spacious sunroom and basement. The nice rear yard is fenced, and the front porch adds to the charm. Top it off with a one car garage and you'll agree that there are LOTS of possibilities here!! Don't miss it!

312 Adams St, Annapolis

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

$774,900

Great historic home built in 1850 in the heart of downtown historic Annapolis. Completely renovated and remodeled in 2023. New kitchen, new bathroom, recessed lights, new ceiling fans, lighting. Stainless steel appliances. Original hardwood floors. Front bedroom has cathedral ceiling. Exterior home has been completely painted in 2025. New decking off rear of home with a patio. Walking distance to tons of restaurants, bars, banks, stores etc. Home is one block off Main Street. Easy access to Route 50, I-97 and Route 2. A must see to believe. Set up a showing and bring us an offer.

32 Cornhill St, Annapolis

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

$3,849,000

6 Beds ⋅ 5 Baths

A truly exceptional historic residence is now available in the heart of downtown Annapolis. Welcome to 16 Maryland Avenue, a distinguished circa-1830 Greek Revival home masterfully restored in collaboration with the renowned Hammond-Wilson Architects. Perfectly positioned just steps from State Circle and the United States Naval Academy, this iconic three-story brick property seamlessly blends timeless architectural beauty with sophisticated modern livability. The main property features 4,474 square feet of refined above-grade living space, complemented by a fully legal, licensed lower-level apartment that offers immense versatility for multi-generational living or premium rental income. In total, the property features six bedrooms, 4.5 bathrooms, and beautifully curated living spaces defined by rich period details, soaring ceilings, and remarkable craftsmanship. Six fully rebuilt, functional wood-burning fireplaces (three equipped with gas starters) serve as stunning architectural focal points throughout the home. Equally captivating are the enchanting outdoor spaces. Here, manicured grounds, lush landscaping, vibrant flower beds, and a serene koi pond create a private garden retreat rarely found downtown. Set on a prime 7,324-square-foot lot along one of the city’s most coveted historic streets, the property offers tranquility just moments from the waterfront and bustling downtown scene. Zoned as a two-family residence, this remarkable property represents a rare, premium investment or a luxurious private estate. Residents will enjoy an unmatched lifestyle, surrounded by boutique shopping, acclaimed waterfront dining, art galleries, historic landmarks, and the unmistakable charm of Annapolis Harbor. Elegant, iconic, and rich with history, 16 Maryland Avenue represents downtown Annapolis living at its absolute finest.

16 Maryland Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$685,000

This is the perfect pied-à-terre and an excellent investment property with its extremely successful long-term rental history! Lots of recent updates, including New HVAC -2025 and new metal roof- 2020. Cozy living room flows to the dining with fun shiplap walls and built-in seating. The well-planned renovated kitchen has access to the private brick courtyard, just the right size for a lovely gathering. The second floor has two bedrooms, a full bath with a conveniently located washer and dryer. Bonus: Plantation shutters throughout this charming home! Wondering about parking? Pinkney Street residents can pull directly in front of their homes to load or unload their cars. Residential street parking (for a nominal annual fee) allows 24/7 parking and new regulations have eased and increased parking for Downtown Residents. Ask about garage parking options! 34 Pinkney is your opportunity to be in the center of the good life Annapolis has to offer!

34 Pinkney St, Annapolis

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

$790,000

Welcome to Eastport—just steps from downtown Annapolis. This charming duplex with rare two-car off-street parking offers the perfect blend of convenience, and coastal living. Freshly painted throughout, this meticulously maintained two-bedroom, 1.5-bath home features numerous updates, including new hardwood flooring throughout, new windows in the living room and kitchen, a new wood-burning stove, and a new A/C heat pump—making it move in ready. A generous deep lot offers excellent potential for future rear additions and expanded living space providing the opportunity to truly make this home your own. Whether you're looking for a full-time residence or the perfect weekend getaway, this Eastport gem has it all. Ideally located near the waterfront, you’ll enjoy easy walking access to marinas, top-rated restaurants, pubs, swim clubs, sailing clubs, and boutique shopping. Don't miss this turnkey offering in a prime location.

422 First St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$557,500

Stunning Oyster Harbor – Coastal Charm Meets Comfort This gorgeous property blends comfort, charm, and the best of coastal living. Nestled in the highly desirable Oyster Harbor community, residents enjoy water privileges and access to a sandy beach, picnic area, fishing pier, and playground—all just a short walk from the front door. Additional amenities include a community marina, boat ramp, and storage racks for kayaks and paddle boards, creating the ultimate waterfront lifestyle just minutes from downtown Annapolis. The home itself is designed for both entertaining and everyday enjoyment. An enormous screened-in porch and a spacious, fully fenced backyard provide plenty of room to garden, relax in a hammock, or host gatherings. After a day at the beach, the outdoor shower is the perfect convenience. Inside, the property features three bedrooms, two full bathrooms, and hardwood floors throughout the main level. Don’t miss the opportunity to live in this beautiful home and vibrant waterfront community—where comfort, charm, and lifestyle come together seamlessly.

1252 Creek Dr, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

$464,900

Welcome to this charming 3-bedroom, 2-bath rancher located on a private, tree-lined corner lot in the highly desirable Cape St. Claire community. Lovingly maintained and thoughtfully updated, this home is ready for its next owner. The kitchen features stainless steel appliances, granite countertops, and a cozy breakfast area. A spacious living room offers flexible use as a combined living and dining space. The primary bedroom includes a private bath with a walk-in shower, while the large second bedroom provides plenty of comfort and versatility. Hardwood floors add warmth and character throughout much of the home. The sunroom serves as part family room and part third bedroom, creating additional flexible living space filled with natural light. An unfinished basement offers endless possibilities for storage, a workshop, home gym, or future finished space. Outside, enjoy a beautifully landscaped yard surrounded by mature trees, colorful flowers, and a high aluminum perimeter fence. A generous parking area adds convenience. Major updates over the past 12 years include: New roof Replacement windows Two split-system heating and air conditioning units Aluminum perimeter fencing Kitchen appliances and countertops And more Residents of Cape St. Claire enjoy outstanding community amenities including beach access, bike paths, parks, and more. The area is also known for its highly regarded schools and welcoming neighborhood atmosphere. Come experience this wonderful home, beautiful yard, and vibrant community for yourself!

919 Blue Ridge Dr, Annapolis

Listing courtesy of RE/MAX Realty Group. Contact:

$550,000

Beautifully updated and filled with thoughtful improvements, this Cape Cod in Annapolis combines model-like interiors, a recently finished lower level, and inviting outdoor living just minutes from the Chesapeake Bay. Blooming perennial landscaping and a covered front porch create a warm welcome, while inside, a deceptively spacious open concept floor plan showcases hardwood flooring, recessed lighting, and a soft neutral palette that carries throughout the home. The living room is bright and airy, highlighted by a partial vaulted ceiling accented with skylights that fill the space with natural light. Just beyond, the renovated kitchen blends style and function with stainless steel appliances, a tile backsplash, abundant cabinetry, roll-out shelving, and a swing-out pantry designed for effortless organization. A dedicated dining area with a modern light fixture completes the main living space with a polished touch. The main level includes a spacious bedroom with a walk-in closet featuring a built-in organization system. Also on this level is a beautifully renovated full bath complete with a double sink vanity, stylish finishes, and a tiled tub and shower surround. Nearby, the laundry room provides storage shelving and convenient access to the backyard. Upstairs, two generously sized bedrooms share an updated full bath with a tiled shower enclosed by frameless glass. One of the upper level bedrooms is enhanced by a charming shiplap accent wall and a cozy window seat, adding character and a tucked-away place to relax. The recently finished lower level expands the living space with a comfortable family room featuring durable wood-look tile flooring, a versatile bonus room, and a sizable storage area. Outdoor spaces are equally inviting, with a deck and patio overlooking the spacious backyard, creating room to entertain, relax, or enjoy the surrounding greenery. A storage shed with a garage door adds functionality, while major updates including the roof and water heater offer additional peace of mind. This location places you moments from some of Annapolis’ most scenic waterfront recreation, including Sandy Point State Park with its sandy beach, marina, fishing and crabbing access, and sweeping Chesapeake Bay Bridge views. Jonas Green Park, Quiet Waters Park, and Thomas Point Park are also nearby, offering trails, kayaking, waterfront overlooks, and endless opportunities to enjoy the natural beauty of the Annapolis area. Hop on the Broadneck Peninsula Trail across the street and head to Sandy Point Park or connect to the B&A Trail.

1470 Log Inn Rd, Annapolis

Listing courtesy of Northrop Realty. Contact: 4104651770

$1,425,000

RARE OPPORTUNITY TO OWN A REMARKABLE PIECE OF ANNAPOLIS HISTORY! The Patrick Creagh House c. 1740 (also known as 160 Prince George Street) is an architecturally significant residence with a gambrel roof structure and features header and English bond brick walls. This property has been thoughtfully adapted for modern living while preserving its timeless character and craftsmanship. Ideally located in the heart of Annapolis just one block from the US Naval Academy Gate 1, City Dock, Main Street and the Maryland State House, this exceptional home offers the best of historic charm and downtown convenience. A welcoming center hall introduces spacious living and dining rooms designed for both elegant entertaining and comfortable everyday living. The private patio and garden create a serene outdoor extension of the home’s living spaces. Upstairs, the home features a primary suite with full bath, two additional bedrooms, a second full bath, and convenient laundry. The lower level provides ideal space for a wine cellar, storage, or additional utility needs. The property’s kitchen, baths and wiring have been updated and the home is move-in ready! This distinguished 18th-century property has been extensively researched and documented and is listed on the NATIONAL REGISTER OF HISTORIC PLACES for its architectural importance and contribution to local history. Patrick Creagh was a man of many skills and was considered an important person in the community. He is mostly known for building the Old Treasury c. 1737 on the Maryland State House Grounds, the oldest public building in the state that was fully restored and opened to the public this year. ***NOTE: FURNISHINGS RECENTLY REMOVED AND INTERIOR WALLS HAVE BEEN PAINTED. Some photos have been virtually staged/AI generated to illustrate the property's design potential only. ***

158 Prince George St, Annapolis

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

$1,100,000

Tucked within the gated waterfront community of Epping Forest, this charming Craftsman bungalow captures the ease and appeal of Annapolis waterfront living with the rare advantage of true one-level living. Perfectly positioned on one of the community’s largest and flattest lots, the property offers a difficult-to-find combination of privacy, outdoor space, and low-maintenance comfort just moments from the Severn River and downtown Annapolis. Inside, the three-bedroom, two-bath residence is filled with warmth and character. Heated floors provide year-round comfort, while dual fireplaces, including one gas and one wood-burning, create inviting gathering spaces throughout the home. The sun-filled great room features transom windows, abundant natural light, and French doors that open seamlessly to the outdoor living areas, creating an effortless connection between indoors and out. The surrounding grounds have been thoughtfully designed to embrace every season of Chesapeake Bay living. Mature landscaping, a dedicated vegetable garden, outdoor fireplace, cedar outdoor shower, and expansive patio create a setting equally suited for quiet mornings or entertaining after a day on the water. Seasonal winter views of the Severn River further enhance the property’s appeal and reinforce its connection to the waterfront lifestyle that defines Annapolis and Anne Arundel County. Life in Epping Forest extends far beyond the home itself. Residents enjoy access to one of Annapolis’ most established and sought-after waterfront communities, complete with a private clubhouse with waterfront dining, deep-water marina, sandy beach, boat ramp, tennis courts, scenic walking trails, and a vibrant calendar of neighborhood events and clubs. The location also offers convenient access to downtown Annapolis, the U.S. Naval Academy, Washington, D.C., Baltimore, and major commuter routes. This is a rare opportunity to own a turnkey home in one of Annapolis’ premier gated waterfront communities, where the Chesapeake Bay lifestyle is part of everyday living. Epping Forest is a Special Tax District. Annual tax: $1,583.64. Community is governed by binding Rules and Regulations.

310 Epping Way, Annapolis

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

$475,000

45 Randall Street is the kind of opportunity that almost never comes available in Downtown Annapolis—a charming boutique storefront positioned directly in the heartbeat of one of Maryland’s most visited waterfront destinations. Perfectly situated between the U.S. Naval Academy and the Annapolis waterfront, this high-visibility commercial property captures constant pedestrian traffic from tourists, locals, midshipmen, and boaters alike. The building’s prominent street presence and classic downtown character create the ideal setting for a boutique retail concept, coffee bar, specialty shop, studio, or investment hold in an irreplaceable location. Surrounded by established national and local retailers, restaurants, and year-round activity, this property offers the rare chance to own a piece of Randall Street in the center of Annapolis’ thriving historic district. Seller financing may be available.

45 Randall St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$578,000

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:

$1,775,000

Price reduced, incredible price for Waterfront in prestigious Watergate! Check the comps! Overlooking the protected “hurricane hole” of Watergate Harbor with direct access to the South River near Thomas Point, 3712 Gateshead Drive offers the ultimate lifestyle with waterviews from every room in the home. Located on a street with homes valued at $4 million to $7 million, you get the waterfront lifestyle at a fraction of the cost. Key points about the home include new kitchen appliances and fixtures, brand new boat lift, 46 foot private pier, three wood burning fireplaces, expansive main floor and upstairs windows overlooking the harbor, hardwood floors throughout, three large decks, two car garage, tons of storage for your water toys and kayaks, and a finished walkout basement--a rarity in waterfront homes. Protected from the waves and wind action of the South River, this harbor allows easy docking for up to a 40 foot power boat in all weather. And, due to the home’s elevation of 15 feet above sea level, no flood insurance is required. Plus the community of Watergate offers a community marina, sandy beach, kayak and paddleboard storage, fire pits, pavilion, new playground and basketball courts. This neighborhood is walkable to Thomas Point Park, and just 3 miles from your favorite restaurants and shopping in Eastport and downtown Annapolis.

3712 Gateshead Dr, Annapolis

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

$2,765,000

5 Beds ⋅ 2 Baths

Welcome to 202 Wardour Drive! This classic 1940 Dutch Colonial offers timeless character, generous living space, and an unbeatable Annapolis location. Situated on a quarter acre lot with large front yard, the south facing location ensures sunny days ahead! Located in the elegant Wardour community which reflects the naturalistic style of its designer, Frederick Law Olmstead, Jr, with its mature trees, meandering roads and preserved open spaces that foster community connection. Inside, the home features five bedrooms, two bathrooms, gorgeous oak floors (recently refinished in 2026), fireplace, bright sun-porch and large 12x 32 back deck. The south-facing orientation fills the home with natural light, creating a bright and cheerful atmosphere throughout. Recent improvements include freshly painted interior and exterior spaces, a newer roof approximately four years old, new porch benches, and a beautifully installed brick paver sidewalk that enhances the home’s curb appeal. A long driveway and rear detached garage provide ample parking and storage. Residents benefit from access to seven community beach areas and a shaded walking trail traversing the neighborhood, that provide a tranquil retreat for adults and a natural wonderland to explore. Conveniently located within walking distance of the local elementary school, Navy Stadium, Annapolis Street shopping and dining, Historic Downtown Annapolis and offers easy access to Rt. 50 for commuters. With classic architecture, spacious interiors, abundant natural light, and an exceptional in-town location close to everything Annapolis has to offer, this is a rare opportunity to own in one of the area’s most beloved neighborhoods. Schedule your private tour today!

202 Wardour Dr, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4433727171

$7,250,000

Perfectly positioned along the waterfront in the prestigious Murray Hill neighborhood of Annapolis, this extraordinary estate represents a rare opportunity to own a fully reimagined luxury residence where privacy, walkability, boating lifestyle, and architectural sophistication converge in one of the East Coast’s most coveted waterfront settings. RenownedBohan Contracting has been extensively renovating the home since October 2025. The home has not been lived in since completion, offering an exceptionally rare “like-new” experience where every finish, appliance, system, and curated detail remains untouched. Set on an unusually expansive waterfront lot for downtown Annapolis standards, the property delivers a sense of scale and privacy that is nearly impossible to replicate within Murray Hill. Mature landscaping, multiple outdoor living spaces, Brazilian Ipe decking, and panoramic water views create a setting that feels worlds away while remaining just moments from the energy and charm of downtown Annapolis. Designed for the discerning buyer seeking a refined waterfront retreat, the residence effortlessly balances elevated entertaining with relaxed coastal living. Whether arriving by boat after a day on the Chesapeake Bay, hosting sunset gatherings overlooking Spa Creek, or enjoying peaceful mornings watching sailboats drift by, the home was designed around an experience. Inside, timeless design and modern luxury unfold at every turn. The fully reimagined chef’s kitchen rivals those found in premier custom estates, anchored by a complete JennAir Noir appliance suite including a 48-inch dual-fuel range with double ovens, professional refrigeration, dual integrated dishwashers, multiple beverage centers, built-in ice maker, and a butler's pantry designed as both a prep and entertaining space. Custom Schrock “Trademark” maple cabinetry, designer-selected Waterworks fixtures, Calacatta Miraggio Cielo quartz with dramatic waterfall detailing, and layered architectural lighting elevate the space into a true showpiece. Throughout the residence, every finish was intentionally selected to create warmth, sophistication, and understated luxury. Wide-plank white oak flooring, custom white oak ceiling beams, Restoration Hardware lighting, Baldwin hardware, integrated Sonos audio throughout the home, Lutron lighting controls, custom plaster fireplaces, upgraded insulation for sound attenuation, and CAT6 wiring provide the seamless blend of craftsmanship and modern infrastructure expected at this caliber of home. The primary suite serves as a private sanctuary, complete with custom built-ins, boutique-style California Closets systems, integrated laundry, and a bespoke fireplace designed to create an atmosphere reminiscent of a luxury waterfront hotel suite. Every secondary space continues the same level of thoughtful execution and design continuity rarely achieved in residential renovations. Outside, the waterfront experience becomes truly exceptional. A private pier with electric, boat lift, paver stone extended driveway, refinished gates, and oversized outdoor entertaining areas creates a lifestyle tailored for effortless luxury. The property’s unique positioning offers both protected water access and breathtaking views while maintaining an uncommon sense of seclusion in the heart of Annapolis. Located just minutes from Downtown Annapolis, the United States Naval Academy, award-winning restaurants, yacht clubs, boutique shopping, and private aviation access, this home is ideally suited for the executive or entrepreneur seeking an uncompromising second home or primary waterfront residence within easy reach of Washington D.C., Northern Virginia, Philadelphia, and New York. The ability to enjoy a true luxury waterfront lifestyle with boating access, walkability, privacy, and substantial land all within one of Annapolis’ most prestigious neighborhoods is extraordinarily rare.

11 S Acton Pl, Annapolis

Listing courtesy of Real Broker, LLC - Severna Park. Contact: 8445517325

$1,999,999

Welcome to 146 Duke of Gloucester Street! As you approach the home, a welcoming front porch will greet you, offering a place to sit and take in all that Annapolis has to offer. Nestled in the heart of historic Annapolis, this beautifully appointed 4-bedroom, 3.5-bath residence seamlessly blends timeless charm with modern sophistication. Rich in character and thoughtfully updated throughout, this exceptional home offers an inviting open-concept main level designed for both comfortable living and effortless entertaining. Step inside to discover sun-filled living and dining spaces anchored by a stunning exposed brick fireplace that adds warmth and historic appeal. The modern kitchen is a true centerpiece, featuring stylish finishes, ample cabinetry, and a functional layout perfect for everyday living and hosting guests alike. The second level features three spacious bedrooms filled with natural light from oversized windows, generous closet space, and two beautifully appointed full bathrooms, creating comfortable accommodations for family and guests alike. Occupying the entire third floor, the expansive primary suite serves as a private retreat complete with a luxurious spa-inspired bath designed for relaxation and rejuvenation. Outside, enjoy a charming backyard—an ideal setting for outdoor dining, gardening, or simply unwinding in your own private oasis. Perfectly situated just moments from the waterfront, renowned restaurants, boutique shopping, and the rich history of downtown Annapolis, this home offers a rare opportunity to experience historic living with all the comforts of modern design.

146 Duke Of Gloucester St, Annapolis

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690

$550,000

Opportunity awaits in sought-after St. Margarets! This 3-bedroom, 1-bath home with hardwood floors, situated on a gorgeous 1-acre lot offering plenty of space and potential. Solid built home they don't make houses like this any longer, needs updating, making it the perfect chance to bring your ideas and renovate to your personal taste. Most major systems updated within last 10 years. Whether you are looking for an investment opportunity or a property to create your dream home, this one has endless possibilities. Home is being sold strictly “AS IS.” Home warranty included.

1509 Duvall Rd, Annapolis

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

$1,500,000

Nestled in the highly coveted Murray Hill neighborhood, one of Annapolis' most picturesque enclaves, this exceptional 1925 Craftsman masterpiece effortlessly blends historic charm with sophisticated modern luxury. Rich in architectural character and thoughtfully enhanced with extensive renovations, this remarkable residence offers an unparalleled lifestyle defined by elegance, convenience, and timeless appeal. From the moment you arrive, the home's undeniable curb appeal captivates with its fresh landscaping, newly renovated rear entry steps, and impeccable craftsmanship. Inside, refinished original hardwood floors, fresh designer paint, stylish new lighting, and beautifully curated updates create a seamless balance between historic integrity and contemporary comfort. Significant investments in the home's infrastructure, including a new HVAC system with a transferable 10-year warranty and upgraded electrical service, provide peace of mind while preserving the home's enduring character. Designed for both refined entertaining and comfortable everyday living, the main level showcases expansive gathering spaces filled with warmth and sophistication. Step into the four seasons room with new ceiling fans and surrounding windows. The original living room invites intimate conversation, while the formal dining room offers the perfect backdrop for memorable dinners and celebrations. At the heart of the home lies an impressive chef's kitchen within the thoughtfully designed addition: a true showpiece that combines luxury, functionality, and style. Featuring Brazilian cherry hardwood flooring and cabinet, granite counterops, stainless steel appliances, updated fixtures, generous prep space, an additional fireplace, and room for casual dining, this extraordinary culinary space was designed to inspire everything from morning coffee to elegant dinner parties. Throughout the home, exquisite architectural details including intricate millwork, original craftsmanship, and abundant natural light create an atmosphere that is both welcoming and refined. The luxurious primary serves as a private sanctuary, highlighted by a second fireplace that adds warmth and ambiance. Two expansive walk-in closets offer exceptional flexibility and can easily function as a private office, sitting room, dressing area, or personal retreat. The spa-inspired en-suite bath features dual vanities, a jetted soaking tub, and a spacious walk-in shower, creating a serene escape at the end of each day. Also plumbed for a wet bar and includes a separate closet for laundry. Three additional generously sized bedrooms provide ample accommodations for family and guests, while the home's three full bathrooms and one half bath have been thoughtfully appointed to blend comfort with elegance. The lower level offers exceptional versatility with a bonus room that can serve as an additional bedroom, fitness studio, home office, or recreation space, complemented by a conveniently located half bath. Additional unfinished basement space provides abundant storage or the opportunity for future customization. One of the home's most exciting opportunities lies within the expansive unfinished top level. Featuring soaring ceilings and substantial square footage, this remarkable space offers endless potential to create an additional bedroom suite, media room, executive office, artist's studio, or luxury recreation area while further enhancing the home's value and functionality. Outdoor living is equally impressive. The newly renovated detached two-car garage provides convenience and charm, while the beautifully maintained grounds create inviting spaces to relax and entertain. During the winter months, seasonal water views add yet another layer of distinction to this exceptional property. Just steps from your front door, stroll to the water taxi for your own nautical uber, restaurants, boutiques, galleries, and entertainment to experience all of what living in downtown Annapolis has to offer.

107 Monticello Ave, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$350,000

This colonial home, built in 1950, blends classic appeal with modern comfort. Spanning 1,584 square feet, this detached residence features four spacious bedrooms and two full bathrooms, making it an ideal retreat for those seeking both space and style. Venture inside to discover a warm and inviting interior adorned with carpet and hardwood floors. The eat-in kitchen, designed for both functionality and social gatherings, offers ample table space, perfect for casual dining or entertaining. The bathrooms feature a convenient tub-shower combination, providing a relaxing oasis after a long day. The unfinished full basement presents a blank canvas for customization, whether you envision a home gym, workshop, or additional storage. Outside, the property features a well-maintained front and rear yard, ideal for outdoor activities or serene relaxation. Parking is a breeze with off-street options or a driveway. This home is conveniently located with easy access to local dining, market and shopping. So, don't miss this opportunity to make his home your own

7 Carver St, Annapolis

Listing courtesy of Century 21 Downtown. Contact:

$565,000

Tucked beneath a canopy of mature trees in the coveted Epping Forest community of Annapolis, this classic cottage offers timeless charm in a truly storybook setting. Surrounded by lush, natural landscaping, the home feels like a peaceful retreat while still being part of one of the area’s most amenity-rich waterfront communities. Inside, warm wood floors flow throughout, complemented by a cozy wood-burning fireplace that creates the perfect gathering space on cooler evenings. The home spans three finished levels, offering flexible living spaces ideal for everyday living, weekend escapes, or hosting guests. A detached garage adds convenience and additional storage, while the home’s setting provides both privacy and a connection to nature. Just a short walk away, enjoy Epping Forest’s exceptional amenities, including sandy beaches, a marina, clubhouse, playgrounds, and scenic waterfront views along the Severn River. Whether you’re seeking a full-time residence or a charming Annapolis getaway, this cottage captures the essence of relaxed, coastal living in one of the area’s most beloved communities.

362 Severn Rd, Annapolis

Listing courtesy of Paul Wesley Real Estate. Contact: 7032822709

$1,950,000

6 Beds ⋅ 4 Baths

Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style property blends 18th-century charm with modern luxury. Perfectly situated on sought- after Duke of Gloucester Street, this vibrant and colorful home offers stunning views of the Maryland State House and extremely rare off-street parking for 6+ vehicles. Originally configured as office space, the residence has been reimagined into six spacious bedrooms and four full baths across two beautifully fully remodeled levels, with the potential for third floor updating plus a large basement with ample storage and updating space. The first floor offers true single level living with a primary suite and second bedroom, while the second level features four additional bedrooms and a convenient laundry area. No detail has been overlooked – from new appliances, countertops, and cabinetry to frameless glass showers, ceramics, extensive trim and molding, recessed lighting, fresh interior and exterior paint, new plumbing/electric and sprinkler system, updated flooring, freshly painted standing seam roof/front dormers and more. The result is a turnkey home where historic character meets modern sophistication & luxury. The property is offered with negotiable furnishings, electronics and art, The Thomas Hyde House is as versatile as it is fun and captivating. Just steps from downtown Annapolis shopping, dining, yacht clubs, local marinas & major commuter routes. Whether as a primary residence, investment property, or distinctive downtown retreat. schedule your showing today.

192 Duke Of Gloucester, Annapolis

Listing courtesy of Samson Properties. Contact: 3017555613

$3,499,000

4 Beds ⋅ 5 Baths

Welcome home. Perfectly positioned at the end of Market Street, this rare waterfront residence offers an exceptional blend of privacy, design and an impeccable lock and leave lifestyle. Located within an intimate six residence enclave, this fully reimagined contemporary brick townhome captures sweeping views of Spa Creek from every level, delivering a front row experience to Annapolis’ most iconic moments, from the Blue Angels to the holiday lighted boat parade. Completely rebuilt from the studs in the last few years with a refined nautical influence, the home spans four light filled levels, where thoughtful design and craftsmanship are evident throughout. Refinished hardwood floors run seamlessly from room to room, while custom steel stair elements made from sailboats, create a striking architectural focal point. An elevator services the main and upper levels, offering both convenience and ease of living. The main living level is both elegant and inviting, featuring a stunning half bathroom, spacious living room with a wood burning fireplace with a marble fireplace surround with custom surrounding built ins that look out to the water. The gourmet kitchen is designed for both everyday living and entertaining, offering high end appliances, a beverage refrigerator, and a dramatic marble waterfall countertop. Additional luxurious details include hidden hinges, walnut doors and tiles from Bali. Sightlines were intentionally designed to draw your eye straight through to the water the moment you enter. The upper level primary suite is a true retreat, offering panoramic water views and a spa inspired bath. An additional ensuite bedroom completes this level, along with a conveniently located second laundry area for effortless everyday living. The top floor provides two more generously sized bedrooms and a beautifully appointed full bath, ideal for guests. On the lower level, a fully equipped second kitchen, recreation space with gas fireplace, full bath with exquisite flooring, laundry, and storage create the perfect setting for extended stays or entertaining, with direct walk out access to the waterfront. Beyond the interiors, the lifestyle is equally compelling. A flagstone courtyard welcomes you home, while rare off street parking adds convenience for owners of this six townhome community. A deeded boat slip sits just steps from your door, offering immediate access to the water. Residents enjoy exclusive access to a heated gunite pool, beautifully maintained grounds, exterior maintenance including the roof, a floating dock and kayak storage, all within this private community. From here, it is a short stroll to the shops and restaurants of downtown Annapolis, or take a scenic water taxi ride and be picked up just steps away from your front door. This is a rare opportunity to experience turnkey waterfront living with effortless access to everything that makes Annapolis extraordinary.

5 Market Quay, Annapolis

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

$1,000,000

5 Beds ⋅ 5 Baths

Rare waterfront redevelopment opportunity in Annapolis. The existing structure is a complete shell and requires a full renovation or rebuild. Ideal for investors, builders, or buyers looking to design and construct a custom waterfront home from the ground up. Located along the protected waters of Oyster Cove, the property includes a deep-water pier and boat house. The existing footprint and favorable waterside placement offer strong potential to maximize views and overall design. Convenient access to the Chesapeake Bay and close proximity to Historic Downtown Annapolis by both land and water. Enjoy boating, sailing, and easy access to surrounding waterfront destinations throughout the region. Property is being sold strictly as-is. A unique opportunity for those ready to take on a full redevelopment project in a prime waterfront setting.

1254 Washington Dr, Annapolis

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

$2,150,000

5 Beds ⋅ 3 Baths

Perfectly positioned in the heart of downtown Annapolis, this distinguished historic residence offers a rare opportunity to own a piece of the city’s architectural legacy while enjoying the convenience of two coveted off-street parking spaces. Overlooking the beautifully preserved grounds of St. John’s College, the home captures timeless views that enhance its already exceptional setting. Steeped in history, the property reflects an evolution of craftsmanship spanning centuries, with the original portion dating to the mid 1800s, an expansion in the late 1800s, and a thoughtfully integrated addition in 1921. Sold fully furnished, the interiors are curated with elegant period pieces that complement the home’s character and provide a seamless, move-in-ready experience. Enjoy peace of mind with the updated electrical and plumbing in 1990 , new hot water heater in January of 2024, new shake shingle roof in April 2026 and 2 new heat pumps in March 2025 Inside, classic architectural details unfold across the main level, where two gracious parlors—each anchored by a fireplace—offer inviting spaces for both intimate gatherings and relaxed everyday living. A welcoming entry hall with an open staircase sets the tone, leading to a charming dining room with its own fireplace and a convenient pass-through to the kitchen, blending historic ambiance with functional flow. The upper levels provide flexibility and space, with four bedrooms and two full baths on the second floor, while an additional bedroom occupies the top level—ideal for guests, a private retreat, or creative workspace. Below, the basement offers practical utility space and storage. Just moments from the shops, restaurants, and waterfront attractions of downtown, as well as the United States Naval Academy, this residence invites you to fully immerse yourself in the vibrant Annapolis lifestyle. From morning walks along tree-lined streets to evenings enjoying the energy of the harbor, this is a home where history, location, and livability converge in a truly special way. Welcome Home!

250 Prince George St, Annapolis

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

$3,750,000

4 Beds ⋅ 6 Baths

Ideally situated on the banks of Luce Creek with sweeping views down the Severn River, 1715 Porters Hill Road is a unique heritage property with over a century of history. Set on a 1.7 acre lot with 265 ft of waterfrontage, the property includes a large, hard-to-find boathouse that provides both charm and utility for all your waterfront adventures. The private pier has 7+ ft water depth and can accommodate a large vessel as well as an assortment of smaller boats. The tram makes access to the water effortless, and the entire property enjoys an exceptional privacy. Steeped in its storied past yet thoughtfully updated for modern living, this retreat captures the perfect balance of historic charm and casual elegance. The heart of the home is a sunlit great room with original log walls and quarried stone fireplace, a vaulted ceiling, and expansive windows which frame water views at every turn. An adjoining den, with separate entrance option, is a perfect place to relax. This could easily become another main level bedroom with ensuite bathroom. The kitchen is striking under its vaulted ceiling accented by exposed beams. The custom cabinetry, GE Monogram stainless steel appliances and generous island give the space so much functionality while maintaining the artisanal character. The kitchen opens to the dining area overlooking the water. The table is anchored by a craftsman-style light fixture, and the entire first and second floors have beautiful wood floors. Step outside and you’re embraced by nature: multiple porches and decks overlook lush, manicured grounds that lead down to the water’s edge. The main-level primary suite is a true sanctuary, designed for privacy and tranquility. The bedroom, with a vaulted ceiling, has a screened porch overlooking the water. Two expansive walk-in closets offer custom organization systems that would make a clothing connoisseur smile. The spa-like bathroom gets lots of natural light from the windows that frame the water, and the freestanding soaking tub is situated to enjoy this view. A dual-sink vanity, heated floors, generous walk-in shower with a built-in bench, and a spacious cosmetic area with dedicated seating make getting ready feel effortless and luxurious. A dedicated laundry area just off the hallway makes day-to-day living very easy. Part of the primary suite is a gracious office with gas fireplace and outdoor access. This is a totally flexible space: install a wall of bookshelves and you’d have a lovely library. Upstairs, there are two generously sized bedrooms. One has water views and a waterside balcony; the other overlooks the lush landscaping out front. There is a hall bathroom. A separate guest bedroom suite above the garage, complete with its own living area and luxe bathroom, is ideal for visiting friends and family who desire more privacy. The Historical Context: Originally built in the 1880s, this log house was one of three identical structures used as hunting lodges. The logs of this original structure were re-purposed in the renovation. The construction of the log walls is one of great craftmanship, including sizing each log to be approximately the same diameter as others. Lore has it that around the turn of the 20th century, the Naval academy wanted to acquire more land by the academy and traded this peninsula for land across from College Creek. The Naval Academy superintendent, Admiral David Porter, could be where the name Porter’s Hill derived from. In the 1920’s, the Whitehead family – three brothers known for running bootleg liquor to Baltimore and Washington during Prohibition — used the property as a place to entertain and stop on the way to Baltimore. In the 1940s, the brothers’ exploits caught up with them, and the State of Maryland confiscated the Porters Hill peninsula. Through a unique trade involving the Jones family’s gravel pit (now the site of the 895 Tunnel), this private waterfront enclave found its next chapter.

1715 Porters Hill Rd, Annapolis

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

$625,000

Priced to attract serious buyers and offering exceptional value in Hillsmere Shores, this is an opportunity you won’t want to miss. The motivated sellers have thoughtfully transformed this 4-bedroom, 2-bath home into a move-in-ready retreat where timeless design meets modern convenience. Completely renovated from top to bottom, the heart of the home is a stunning brand-new kitchen featuring stylish cabinetry, contemporary finishes, and all-new appliances. Both bathrooms have been fully redesigned with clean, classic aesthetics, while extensive additional updates provide confidence and peace of mind for years to come. Every renovation was completed with intention, using quality materials and enduring design choices rather than quick cosmetic fixes. The result is a home that feels cohesive, fresh, and truly turnkey—allowing its next owners to move in and immediately enjoy everything it has to offer. Beyond the front door, discover the unmatched lifestyle of sought-after Hillsmere Shores. Just minutes from downtown Annapolis, this water-privileged community offers a voluntary HOA through the Hillsmere Shores Improvement Association, providing optional access to outstanding amenities including a private marina with boat slips, multiple boat ramps and kayak launches, a sandy community beach with pavilions and waterfront gathering spaces, and more. Residents also enjoy convenient access to Quiet Waters Park, shopping, dining, and everyday essentials, creating the perfect balance of natural beauty and modern convenience. With extensive updates already completed, exceptional community amenities, and sellers ready to make a deal, this beautifully renovated home represents one of the best opportunities to enjoy the Hillsmere Shores lifestyle from day one.

420 Edgemere Dr, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$899,000

Open House Saturday July 11th, 11AM - 1PM! Come Join us to see this adorable bungalow in a prime West Annapolis Location! Easy one-level living with a great fenced-in yard and a large, detached garage. Super fun, walkable location—catch Navy Midshipmen football games or stroll to Chessie’s Wharf, Positano’s, Bean Rush Cafe, Always Ice Cream Company & more! Just a short distance to Downtown Annapolis for waterfront dining, shopping, and historic charm.

607 Melvin Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$2,295,000

5 Beds ⋅ 4 Baths

This exceptional Historic District home combines the charm of a classic Annapolis address with a substantial 2026 renovation in all the right places. A stunning new kitchen, custom wet bar, expanded pantry area, completely reimagined third floor, new full bath, and New HVAC system bring modern function and style to this timeless home. Water access is at the end of the block, Acton's Cove waterfront park is around the corner, and City Dock, Main Street, restaurants, shops, and the Naval Academy are all within easy walking distance. Easy parking on quiet Market Street. The new kitchen features custom cabinetry, Taj Mahal quartzite countertops, ceramic tile backsplash, unlacquered brass hardware, designer lighting, and a full suite of GE Monogram appliances. The expanded pantry area offers plenty of storage, a separate freezer, and ice maker, while the custom wet bar includes reeded glass cabinetry, brass detailing, a dedicated sink, and generous storage for entertaining. A full-width screened porch spans the front of the home, while 10-foot ceilings, original architectural details, and multiple gathering spaces create warmth and character throughout. The main level includes a paneled office, formal living and dining rooms, and a casual family room that opens to the eat-in kitchen and rear patio with gazebo. Seasonal water views can be enjoyed from several rooms. Upstairs, the primary suite offers winter water views, dual organized closets, and an updated bath. A 2nd bedroom with hall bath and laundry room are located on this level. The 3rd floor has been completely reimagined to create 3 additional rooms with built-in storage and a beautiful new full bath featuring classic finishes, custom millwork, and quartz countertops. A rare opportunity to enjoy the character of Historic Annapolis with the benefits of a major recent renovation, all tucked on a quiet street in the heart of the Historic District. Water access is just steps away, downtown Annapolis is an easy walk, and everyday convenience is rarely this effortless.

83 Market St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$489,999

Welcome to this charming Cape Cod just minutes from downtown Annapolis and Eastport, where classic 1950s character meets thoughtful modern updates. Hardwood floors and original architectural details set the tone on the main level, with abundant natural light filling the living room and highlighting a cozy wood-burning fireplace. The updated eat-in kitchen features granite countertops, a peninsula for casual dining, and easy flow for everyday living and entertaining. Two spacious bedrooms and a full bath complete the main level, while upstairs the entire level is dedicated to a private primary retreat with a walk-in closet and a beautifully appointed ensuite bath featuring a soaking tub, walk-in shower, and dual vanity. The expansive, fully fenced backyard offers exceptional outdoor space with a deck and extensive hardscaping already in place, plus plenty of room to garden, entertain, or even design a future pool. The unfinished lower level provides great ceiling height, walk-out access to the yard, and excellent storage with potential to finish. With quick access to Forest Drive and Route 50, and just moments from Truxton Park, Pip Moyer Recreation Center, Spa Creek trails, tennis courts, and the public boat ramp, this location delivers some of the very best of Annapolis living.

76 Summerfield Dr, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

$390,000

* Price Drop! Don't miss out on this beautiful fully updated Eastport home for less than $400k! * Welcome to 1019 President St in the heart of Eastport—where charm, space, and modern upgrades come together just minutes from the water and Historic Annapolis. This beautifully renovated 3-bedroom, 2-bath home offers a rare combination of cozy living and exceptional outdoor space. Situated on an oversized lot with a classic white picket fence, the property features a huge yard, private parking for 4+ vehicles (a true rarity here), a welcoming front porch, and a spacious back patio—perfect for entertaining, relaxing, or simply enjoying the space that sets this home apart. Inside, the home has been completely transformed with top-to-bottom upgrades, including brand new central HVAC system, complete electric upgrades, new flooring throughout, a stunning modern kitchen with high-end finishes and appliances, and beautifully designed bathrooms. Natural light pours in on every level, highlighting the clean, fresh finishes, generous closet space, and an easy, functional layout. Located just a short walk to the water, nearby parks, and everything Eastport is known for—and only minutes to downtown Annapolis—this home offers a lifestyle that’s hard to match, blending comfort, convenience, and a truly standout setting.

1019 President St, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact: 3015198100

$775,000