4 Bedroom Annapolis Real Estate

Luxury living without the upkeep in Annapolis! This extraordinary residence combines two units into one expansive, stunning home in Annapolis Towne Centre offering over 3,400 square feet of impeccably finished living space on one level. Completely gutted to the studs and reimagined, this one-of-a-kind home places you right in the center of it all—and only minutes from Downtown Annapolis—yet feels like a private retreat from the world. Designed for both grand entertaining and everyday comfort, the custom gourmet kitchen anchors the home and flows seamlessly into inviting living spaces. Sound-proof, glass-tempered doors allow rooms to transition effortlessly from open and connected to intimate and private. Thoughtful details include hidden, built-in Sonos speakers, exquisite moldings, tray ceilings, modern lighting, and a stunning blend of wood and marble flooring throughout. Wine enthusiasts will appreciate the climate-controlled wine room, while the primary suite is a true sanctuary, featuring a glamorous dressing room, multiple custom closets with secret storage, and a spa-like ensuite bath with hand-cut mosaic tile flooring and an oversized walk-in shower with glass door linen closet. Featuring a fully integrated Lutron smart home system, this residence offers effortless control of lighting, motorized shades, audio, temperature, and security access. Additional highlights include three additional bedrooms, two additional full baths, four garage parking spaces and two storage units. Residents enjoy world-class amenities including concierge service, fitness center, yoga studio, library, meeting rooms, elegant lounge spaces, and a spectacular rooftop pool—delivering a lifestyle that is as effortless as it is refined. Towne Centre has become the new heart of Annapolis — a vibrant destination where you’ll find everything you need, from grocery shopping and a premier fitness center to exceptional dining and upscale retail.

1915 Towne Centre Blvd Unit #406, Annapolis

Listing courtesy of Compass. Contact: (703) 229-8935

$995,000

Welcome to Eastport Estates at Griscom Square, a brand-new construction community of just 11 luxury single-family homes, located within one mile of downtown Eastport! Each residence showcases high-end finishes, spacious open-concept layouts, 9-foot ceilings, 4-5 Bedrooms, gourmet kitchen, modern baths, 2-car garages with private parking, and quality craftsmanship throughout, creating a truly well-built home. Inspired by its coastal setting, each home incorporates light-filled spaces and design elements that reflect Eastport’s nautical character. Enjoy effortless access to Eastport’s vibrant waterfront dining, live music, local marinas, yacht clubs, and scenic sunset views - or bike to or take the water taxi to City Dock, downtown Annapolis, and the United States Naval Academy. Luxury, lifestyle, and location - together in one place. This is a rare opportunity to build your own home this close to town. Lot and model options available!

105 Griscom Square Way, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$568,000

Elegant brick and siding split-foyer residence offering 4 bedrooms and 3 renovated full bathrooms on a beautifully sized 0.21-acre lot. The thoughtfully designed upper level features a sun-filled living room, formal dining area, well-appointed brand new kitchen with new appliances, and seamless access to the rear deck—perfect for refined indoor-outdoor living. Three bedrooms and two full baths complete the main level. The lower level is highlighted by a private primary suite with a generously renovated full bathroom, providing an ideal owner’s retreat or guest quarters, along with a spacious family/recreation room, laundry area, and mechanical room. Luxury vinyl flooring extends throughout both levels, complemented by windows in excellent condition. Major updates include the roof and HVAC system. Serviced by well and public sewer. A well-maintained home offering comfort, privacy, and timeless appeal.

721 Fairway Dr, Annapolis

Listing courtesy of KW Metro Center. Contact: 7032246000

$1,079,990

Spacious and elegant, this 4-bedroom, 4.5-bath home offers approximately 4,400 sq. ft., with the option to expand to 5,300 sq. ft. with a fourth level. The gourmet kitchen features double wall ovens (upper with air-fry), a 36" gas cooktop, and choice of cabinetry or stainless steel hood. Enjoy a sunroom, cozy fireplace, 9-foot ceilings on all levels, and a finished basement with full bath. Energy-efficient upgrades include a tankless water heater and two-zone HVAC. Private setting near Quiet Waters Park. Fully furnished model available. Estimated move-in July/August.

113 Stilly Way, Annapolis

Listing courtesy of Builder Solutions Realty. Contact:

$1,064,990

Spacious and elegant home offering 4 bedrooms, 3.5 bathrooms, and approximately 4,400 sq. ft. of living space, with the option to expand to 5,300 sq. ft. by adding a fourth level. The gourmet kitchen features double wall ovens (upper oven with air-fry), a 36-inch gas cooktop, and the choice of a cabinetry hood or stainless-steel chimney hood. Additional highlights include a sunroom, fireplace, 9-foot ceilings on all levels, two-zone heating and air conditioning, and a tankless hot water heater. The finished basement offers over 1,100 sq. ft. of additional living space with a full bathroom. Energy-efficient upgrades enhance comfort and savings. Ideally located near Quiet Waters Park, providing a peaceful and private setting. Fully furnished model available for viewing, open 7 days a week from 9:00 AM to 8:00 PM.

117 Stilly Way, Annapolis

Listing courtesy of Builder Solutions Realty. Contact:

$549,999

Welcome to 102 Vanguard Lane, an elegant gated community offering a home with refined finishes and comfort in the heart of Annapolis. Rich hardwood floors throughout the main level, while the kitchen impresses with granite countertops and a brand-new refrigerator. Custom plantation shutters & blinds; upgraded lighting & more! Exterior w/ Hardiplank siding & beautiful deck off kitchen that includes an amazing indoor/outdoor fireplace! This beautifully updated home showcases brand-new paint and new carpet throughout, creating a pristine, move-in-ready experience. Thoughtfully refreshed and designed for both everyday luxury and memorable gatherings, this home offers an exceptional lifestyle just minutes from Annapolis dining, shopping, and waterfront attractions. A rare opportunity to enjoy comfort, style, and location—all in one exceptional property.

102 Vanguard Ln, Annapolis

Listing courtesy of RE/MAX Concierge Realty. Contact:

$1,157,456

Foreclosure opportunity in sought-after Annapolis! Spacious 4BR/3.5BA Colonial with over 4,500 sq ft of living space. Features include multiple living areas, large kitchen footprint, finished lower level, and generous bedroom sizes. Private backyard with in-ground pool ready to be restored. Excellent potential for renovation or investment. Convenient to shopping, dining, major routes, and downtown Annapolis. Sold strictly AS-IS. Schedule your showing now!

371 Carriage Park Way, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

$1,375,000

There are very few multifamily dwelling units in the City of Annapolis. This creates a rare and amazing opportunity for buyers to own one of the few existing multifamily dwelling units that’s a triplex. There are so many option available for this property in the heart of Historic Annapolis. You may want to convert the entire home back to one living unit. You may want to live in one, long-term rent the other two or short term rent one. You may choose that it be be used for a couple/single person to live in one apt and rent out 2 or have a multigenerational combined family living in 1, 2 (while renting 1) or all 3. There are so many possibilities to enjoy this amazing property. This is 3 fully finished levels and units above grade. The basement level houses the storage area, HVAC and shared laundry area. All of the units are fully furnished with kitchen appliances, items, dishware, glassware, beds, linens, furniture, you name it, it is there and conveys. This is steps away from the Naval Academy. The main level entry has a hallway with stairwell to the upper level units and access to the man level unit Apt 1 and the basement. Apt 1 offers a foyer, eat-in kitchen, full bath, living room, bedroom and access to the rear patio fenced in area. The 2nd level has Apt 2 with a living room, kitchen, bath, 2 bedrooms and access to the rear patio area. The third upper level offers a full bath, galley kitchen, bedroom and large living area with space for a table, couch and mor furnishings. All units have the old time charm with modern components. All three units offer high ceilings. This is a very popular property so bear with us as we want to accommodate all showing requests. The most advance notice you can give the better. There may be times when all 3 may not be able to be seen on the same day. There is a virtual tour where you can walk through the entire property, zoom in and out and see the whole house from your phone or computer. This is also listed as Multi-Family MLS# MDAA2132270. Parking info is loaded in the documents section. Unit schedule: Unit 1 is lived in and can be seen normally with one days notice. Unit 2 and Unit 3 have various bookings and more notice is required.

165 King George St, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact: 4102669005

$2,950,000

TO BE BUILT, luxury home on Back Creek adjacent to Eastport. Quiet dead end street. Only steps away from the community marina with deep water slips. Permits in process for home and private pier. Primary suite on the main level. 5075 sq/ft of finished living space. Intentionally designed large home that can also live small when guests are away. 5br 4.5 Bath with 2 car garage. Offering includes 10' tall ceilings, White European Oak Floors, Furniture Grade Cabinets, Quartz counters, Sub Zero/Wolf Appliances, Screened porch with Outdoor fireplace. Contact LA to schedule a tour of the property. Builder maintains a model home by appointment only. Witness the refined details. $10k in Free options for use of Builders approved lender and title company. Visit Whitehall Building & Company's site for additional information. 100% VA financing available.

703 B Glendon Ave, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$949,900

Just across the street from the water in Southaven, this Annapolis home offers the kind of space and flexibility that’s increasingly hard to find. Recently updated, the main level includes a renovated kitchen with quartz countertops, dual ovens, gas cooking, stainless steel appliances, and modern cabinetry. The main level also features a living room with built-in speakers, a dining room, an optional sitting room, a half bath, garage access, and a coat closet at the front entry. Upstairs are four well-sized bedrooms, two thoughtfully updated full baths designed with a clean, timeless aesthetic, and a laundry room. The walkout lower level remains unfinished and offers excellent storage, along with a bathroom rough-in for those who may wish to explore future expansion. Exterior updates include a newer roof and a recently paved driveway. The attached two-car garage supports everyday needs, while the detached three-car garage offers access to an unfinished upper-level space that provides additional room to tailor to personal needs. A back deck extends off the main level, with a second deck accessible from the unfinished space above the three-car garage. Community water access is located across the street. The Southaven community also offers a community pier and a kayak/paddleboard launch area. Set on a generous lot with ample storage and water access, 2942 Southaven Drive combines usability with the relaxed coastal character that makes this part of Annapolis so appealing.

2942 Southaven Dr, Annapolis

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

$896,000

Another fantastic new home by Vineyard Builders who has an amazing reputation in the Cape is in the final stages of completion. New Construction in Cape St. Claire. Home is now framed and under roof. Delivery date will be beginning of September. Days on the market began when lot was purchased. Please look at the documents section of the listing to see all standard features included with this home. Pictures shown in this listing are of the home now framed and a previous completed home built at 1216 Ramblewood Drive Annapolis, Md. also located in Cape St. Claire during the construction of that home. This same floor plan will be constructed on this site. Please contact listing agent with any questions.

1217 Hampton Rd, Annapolis

Listing courtesy of Cook Real Estate Brokerage. Contact: (410) 570-1659

$3,595,000

Coveted West Annapolis Waterfront property with deep water floating dock! Recently updated with fresh paint, refinished floors and new carpeting throughout. Experience elegance and grace in this stunning 4 story home that is sure to captivate. The contemporary architecture and voluminous spaces mixed with traditional finishes and floor plan creates a wonderful combination. Expertly designed and built additions include the glass enclosed lanai with elevator and guest room above in 2006, Living room, 2 car garage and bird's nest with balcony completed in 2009, gourmet Kitchen was expanded and beautifully updated in 2015. Upon entry, the soaring foyer is awe-inspiring and the elegant living room, with built-in bar, sets the tone. With 3 custom bars and multiple gathering areas, this home is perfect for entertaining. The gourmet kitchen is a chef's dream, featuring a large island and top-of-the-line finishes and breakfast nook, which flows seamlessly into the spacious family room with walls of windows overlooking Weems Creek. The adjacent library/den boasts mahogany built-ins and flooring, gas fireplace and views; a perfect place to curl up with a book. This home offers three ensuite bedrooms for ultimate comfort and privacy. The master bedroom is a sanctuary with a vaulted ceiling, custom built-ins, enormous walk in closet for 2 and the best views in the house. Wake up every morning and enjoy the activity on the sparkling waters of the creek and the Severn River. The spacious guest room suite with glass breezeway from the main house boasts an elevator directly into the room, creating a truly private oasis for guests and family. This floor also includes an additional bedroom or theater room with adjacent hall bath; providing flexible living options. The fourth floor features a unique bird's nest with elevator access and a wrap-around deck offering panoramic views of Weems Creek and the Severn River. With three elevators throughout the house, accessibility to all four levels is effortless. The exquisite sunroom with folding glass doors epitomizes indoor/outdoor living. Simply open 2 sides of the room to the outdoors and let the party flow onto the sprawling rear deck. The wrap-around IPE deck and multiple level seating areas are ideal for taking in the incredible views from every vista. The lush landscaping and stone stairs lead to the water's edge and the private pier with deep-water floating dock with multiple slips can accommodate a 50ft yacht. Be sure to not miss the stone patio on the way down; ideal for relaxing as the sun sets. This property truly captures the essence of waterfront living by blending luxury and comfort in an unparalleled setting. Welcome Home!

411 Ridgely Ave, Annapolis

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

$2,375,000

Stunning Waterfront New Construction 0n Back Creek in the Eastport area. Don't miss this rare opportunity to build your dream home in one of Annapolis’s most sought-after waterfront communities. Ideally located on a quiet, picturesque corner lot in Eastport, this beautifully designed custom home will offer expansive views of Back Creek and luxury finishes throughout. Enjoy wide plank floors, dramatic walls of glass to showcase the water views, custom built-in kitchen cabinetry, and a chef’s kitchen featuring high end appliances, quartz countertops, oversized island, and a full-height backsplash. Optional elevator can be added for additional convenience. Every detail has been thoughtfully selected to blend style, comfort, and function for modern coastal living. This home is conveniently located just close to the heart of Eastport—renowned for its strong sense of community, marinas, walkability, and vibrant dining scene. Enjoy morning strolls to your favorite coffee shop or evenings out at nearby waterfront restaurants. Located in the Parkwood Civic Association (PCA), a voluntary neighborhood group with $100 annual dues that support maintenance of local green spaces—including Hoffman Park and the community docks. PCA membership is also required to apply for a dock slip. Contact the listing agent today or check out Whitehall Building & Co's website to schedule a tour of the model home and start customizing your waterfront residence. With construction soon underway, you could be enjoying life on the water by next boating season.

703 A Glendon Ave, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$1,350,000