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Annapolis

One of the most popular communities provided by Maryland Sandbox

Annapolis

About Annapolis

Nestled on the shores of the Chesapeake Bay, Annapolis, Maryland, is a charming and historic community that seamlessly blends waterfront beauty with rich maritime heritage. As the state capital and home to the United States Naval Academy, Annapolis boasts a vibrant downtown area filled with unique shops, gourmet restaurants, and stunning colonial architecture. Residents and visitors alike can enjoy picturesque strolls along the scenic harbor, where sailboats and yachts bob in the water. With its engaging cultural scene, including art galleries, theaters, and annual festivals, Annapolis offers a lively atmosphere for all ages. The community takes pride in its top-rated schools, making it an ideal place for families. Outdoor enthusiasts can explore numerous parks, nature trails, and waterfront activities, while history buffs can immerse themselves in the city's storied past at landmarks such as the Maryland State House. Whether you're seeking a lively urban environment or a peaceful retreat by the bay, Annapolis is a vibrant community that truly has something for everyone.

One of the most popular communities provided by Maryland Sandbox

318

# of Listings

3

Avg # of Bedrooms

$463

Avg. $ / Sq.Ft.

$1,069,668

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

103 Properties Found. Page 2 of 7.

Welcome to one of Annapolis’ most sought-after waterfront communities, where residents enjoy a waterfront pool, and a private marina and boat ramp that’s just minutes to the Chesapeake Bay by boat. This beautifully updated four-bedroom home at 1141 Mainsail Drive in Anchorage is situated just down the block from all these amazing amenities and sits on a spacious one-third acre lot framed by mature trees and manicured landscaping.
Inside, the home features a bright open floor plan with gorgeous hardwood floors, crown & chair-rail moldings, and large windows that fill the space with natural light. The chef’s kitchen boasts stainless steel appliances, quartz countertops, and an inviting breakfast area that opens to a cozy family room with a double-sided brick fireplace. The sliding glass doors that open to the back deck make grilling and al fresco dining a breeze. A formal living and dining room offer flexibility for entertaining, and the main level also includes a powder room and access to the oversized two car garage.
Upstairs, the primary suite includes a private bath with a renovated walk-in shower and updated fixtures. Three additional bedrooms are ample in size and there’s a second renovated bathroom. There is a wonderful office nook overlooking the front yard. The finished lower level, with Pergo flooring, provides a spacious recreation and/or office space with room for storage and a workshop area. Outdoors, the circular driveway provides a gracious entry and leads to an attached two-car garage. The beautifully landscaped backyard is private and offers plenty of space for enjoyment in addition to the brick patio.
Residents of Anchorage enjoy an unparalleled lifestyle centered around the community’s marina, pool, and social events, all while being just minutes from downtown Annapolis, Quiet Waters Park, and top-rated schools. Whether boating on Lake Ogleton, gathering at the waterfront picnic area, or simply enjoying evening walks around the neighborhood, life in Anchorage feels like a year-round retreat.

ANNAPOLIS

1141 MAINSAIL DRIVE

4 Beds

2 Baths

3,264 Sq.Ft.

$910,000

MLS#: MDAA2128894

Welcome Home to spectacular 722 Coybay Drive! This elegant brick-front Colonial is located in the amenity-rich Kingsport community, offering both luxury and convenience. Featuring 5 bedrooms, 3 full baths, and 2 half baths, this home provides abundant space for family, guests, and entertaining. Inside, enjoy a well-designed layout with spacious living areas, a gourmet kitchen, and refined finishes throughout. The primary suite is a true retreat with a luxurious bath, while additional bedrooms offer flexibility for home offices, hobbies, or guest rooms. Outside, the property boasts a beautifully maintained exterior and access to the community’s top-notch amenities, including a pool, trails, and recreational areas. Located close to shopping, dining, and commuter routes, this home perfectly blends elegance with everyday convenience. Don't miss your chance to tour, schedule your showing today and experience the charm and sophistication of 722 Coybay Drive!

ANNAPOLIS

722 COYBAY DRIVE

5 Beds

3 Baths

5,387 Sq.Ft.

$899,999

MLS#: MDAA2128170

Welcome to Kingsport , a water privileged community packed with beautiful homes and all the modern conveniences. This stunning 5BR/4.5BA luxury home is ready for new beginnings. Grand residence featuring hardwood foyer, formal oval dining room, living room, and main-level office. Gourmet kitchen with custom island cooktop, dual wall ovens, granite counters, and abundant cabinetry opens to the family room with vaulted ceilings, plantation shutters, and gas fireplace. The additional room off the foyer is perfect for the home office. The upper level includes a primary suite with spa bath and dual walk-in closets, en-suite second bedroom, plus two additional bedrooms with shared bath. The finished lower level offers a rec room with a wet bar, guest suite, playroom and an abundance of storage. Fully fenced yard with paver patio and raised garden bed. Property backs up to woods and walking paths. The community offers a pool, multiple playgrounds, hiking and biking trail, kayak launch and storage. The community pier situated at the end of Crab Creek is the perfect place to unwind, go fishing or have a picnic. Close proximity to all commuter routes and minutes from downtown Annapolis

ANNAPOLIS

730 CRISFIELD WAY

5 Beds

4 Baths

5,151 Sq.Ft.

$865,000

MLS#: MDAA2120506

Ameri-Star Homes is pleased to offer this incredible opportunity for a to-be-built, craftsman-style home situated on a beautiful almost half acre lot with walkout basement condition in the well-established neighborhood of Rolling Knolls, in Annapolis. *Builder is paying $5,000 TOWARDS CLOSING COSTS with use of builders approved lender and title company. Our exciting Taft model is appointed with an abundance of features that you deserve, 9-foot ceilings main level, engineered hardwood floors on the entire first floor, granite or quartz countertops in the kitchen, upgraded cabinets with soft close doors and drawers, ceramic-clad baths and laundry room floor, stainless appliances, washer and dryer package, stone accents on the exterior, architectural roof shingles, upgraded craftsman style moldings, craftsman newel posts with oak rails with black iron pickets, a garage door opener with wifi, a sodded lawn and generous landscaping package and so much more. ALL STANDARD! A home that you certainly will be proud to drive up to. There is 2,580 square feet of above grade living space to enjoy and plenty of room for expansion including adding an optional finished rec room, an optional basement bedroom and optional full bathroom in the basement at an additional cost. This location is a convenient commute to Baltimore and Washington DC and just minutes to historic Annapolis, Maryland. This is a rare opportunity for new construction in the Annapolis area. The images illustrated in this listing may be representative of the builder’s work in likeness and quality and may show optional features that are available. Prices, terms, conditions, and availability are subject to change without prior written notice. Other plans are available for this lot, including a rancher plan.

ANNAPOLIS

2175 GLENCREST CIRCLE - TAFT MODEL

4 Beds

2 Baths

3,480 Sq.Ft.

$849,990

MLS#: MDAA2123152

Experience over 5,000 square feet of refined comfort in this beautifully appointed 4-bedroom, 2.5-bath Colonial, nestled at the end of a quiet cul-de-sac in the highly desirable Bowen Manor community of Annapolis. From the moment you step inside, you’ll appreciate the soaring ceilings, abundant natural light, and seamless flow that make this home perfect for grand entertaining and effortless everyday living.

The main level is anchored by a expansive kitchen featuring a large center island, double ovens, and a sunny eat-in area that opens to the spacious family room with a cozy gas fireplace. A bright, window-lined sunroom just off the kitchen provides a welcoming spot for morning coffee or quiet afternoon reading. You’ll also find a private home office tucked behind French doors, along with elegant formal living and dining rooms enhanced by custom moldings and thoughtful details throughout.

Upstairs, the expansive primary suite offers a true retreat, complete with a lighted tray ceiling, a massive walk-in closet, and a spa-like en-suite bath. Three additional generously sized bedrooms share a stylish full bath, and the convenient upstairs laundry room adds modern functionality.

The walk-out lower level provides a second family room—ideal for movie nights, game days, or play space—with plenty of room left over to finish as a rec room, gym, media center, or guest suite.

Outside, enjoy the fully fenced backyard and spacious deck—perfect for summer barbecues or peaceful evenings at home. Located just minutes from commuter routes, shopping, dining, and historic downtown Annapolis, this home offers space, style, and location—plus the rare bonus of an assumable 4.625% mortgage.

Don’t miss your chance to make this exceptional home your own!

ANNAPOLIS

229 BOWEN COURT

4 Beds

2 Baths

5,112 Sq.Ft.

$849,900

MLS#: MDAA2127918

Rare Opportunity to Build Your Dream Home Near Historic Downtown Annapolis
3268 Kitty Duvall Drive | Offered at $875,000 |
Includes Lot, Site Work Budget & Customizable Chestnut Model by Timberlake Homes

Embrace the chance to create your dream home on a peaceful, build-ready .62-acre wooded lot just minutes from the charm and energy of downtown Annapolis. Nestled off a quiet, private gravel lane, this flat homesite offers public sewer access and the benefit of preliminary engineering already completed—making it easier and faster to build.

This exclusive opportunity includes Timberlake Homes’ highly flexible and elegant Chestnut floorplan, thoughtfully designed to combine comfort, functionality, and style. Enjoy the tranquility of a secluded setting with convenient access to vibrant shops, waterfront dining, cultural landmarks, and historic marinas.

Highlights of the “To Be Built” Chestnut Model:
2,251–2,498 sq. ft. | 4 Bedrooms | 2.5+ Bathrooms

Welcoming open foyer with tucked staircase and central powder room
Spacious family room with optional 4' extension and fireplace
Gourmet eat-in kitchen with 42” maple cabinetry, granite countertops, walk-in pantry, breakfast island, and Samsung appliances (including a double wall oven)
Mudroom entry from a 2-car garage
Elegant oak stairs from main to upper level
Hardwood, LVP, or laminate flooring throughout main level
9’ ceilings on main level with 9’ foundation walls for added volume
Ceramic tile in all bathrooms
Stylish brushed nickel hardware and Moen® fixtures throughout
Optional features: deluxe primary bath, third full bath, sunroom, and lower-level recreation room

Chestnut Floorplan Overview:
The Chestnut offers timeless appeal with a flexible layout. A bright foyer opens to a versatile flex room, while the central staircase leads to four generously sized bedrooms upstairs, a full hall bath, and a convenient second-floor laundry room. Enhance your living space with thoughtful options like a sunroom, extended family room, or finished basement recreation area.

Additional Notes:
Timberlake Homes makes no representations regarding the lot or its sale. Please contact the listing agent to connect directly with the builder. Photos and floor plans may show upgraded features not included in the base price. Final pricing may vary depending on selected options and builder allowances.

ANNAPOLIS

3268 KITTY DUVALL DRIVE

None Beds

None Baths

N/A

$849,000

MLS#: MDAA2117802

Welcome to 42 City Gate Lane in the desirable City Gate neighborhood of Annapolis. This move-in ready residence offers 3 bedrooms, 2 full baths, and 2 half baths, thoughtfully updated for modern living. The showpiece main level features a complete open-concept renovation: upgraded cabinetry, a generous center island, sleek quartz counters, and stainless steel appliances—all seamlessly connected to bright living and dining spaces with flowing hardwood floors. Step outside to a private patio that’s ideal for entertaining or a quiet morning coffee. Recent improvements provide peace of mind and curb appeal, including a new roof and gutters installed in 2024, along with a new front door and rear sliding door. With a walkable location just moments to Downtown Annapolis and the Waterfront—as well as the State House, the U.S. Naval Academy, shops, dining, parks, and commuter routes—this home blends style, convenience, and comfort in one exceptional package. Convenient overflow parking at both ends of the street.

ANNAPOLIS

42 CITY GATE LANE

3 Beds

2 Baths

2,100 Sq.Ft.

$824,900

MLS#: MDAA2124168

New on site 1 day ago

Ameri-Star Homes is pleased to offer this incredible opportunity for a to-be-built, craftsman-style home situated on a one-of-a-kind, almost 1-acre homesite, in the sought-after Annapolis area. *Builder is offering Pre-Construction Pricing and paying $5,000 Towards Closing Costs with use of builders approved lender and title company. Our exciting Taft model is appointed with an abundance of features that you deserve, 9-foot ceilings main level, engineered hardwood floors on the entire first floor and upper hallways, granite or quartz countertops in the kitchen, upgraded cabinets with soft close doors, drawers and crown molding, ceramic-clad baths and laundry room floor, stainless appliances including refrigerator, a washer and dryer package, stone accents on the exterior, a portico porch, architectural roof shingles, upgraded craftsman style moldings, craftsman newel posts with oak rails and black iron balusters, a sodded lawn and generous landscaping package and so much more. ALL STANDARD! A home that you certainly will be proud to drive up to. There is 2,580 square feet of above grade living space to enjoy and plenty of room for expansion by adding optional finished spaces in the basement including a rec room, bedroom, den / media room and a full bathroom at an additional cost. Come home and enjoy the Chesapeake lifestyle in the heart of Annapolis? This property is located just minutes to Oyster Creek, Fishing Creek and historic Annapolis with plenty of access to shopping and dining choices. You will enjoy a convenient commute to Baltimore and Washington DC. This is a rare opportunity for new construction on a large lot in this sought after area. The images illustrated in this listing may be representative of the builder’s work in likeness and quality and may show optional features available. Prices, terms, conditions, and availability are subject to change without prior written notice. Other Models Are Available.

ANNAPOLIS

3123 ARUNDEL ON THE BAY ROAD - TAFT MODEL

4 Beds

2 Baths

3,480 Sq.Ft.

$799,990

MLS#: MDAA2129594

Ameri-Star Homes, one of the area’s premier homebuilders, is excited to be offering our spectacular craftsman style "Georgetown" Rancher Model on this beautiful almost half-acre lot in the well-established neighborhood of Rolling Knolls, IN Annapolis, MD. *CURRENT INCENTIVES: PRE-CONSTRUCTION PRICING AND $5,000 PAID TOWARDS CLOSING COSTS. This exciting rancher plan offers 1,757 square feet of above grade finished living space, 3 bedrooms, 2 bathrooms with a 2-car garage. This to-be-built rancher style home features a maintenance-free exterior with architectural-grade roof shingles, a sodded yard with a generous landscaping package. A home that you certainly will be proud to drive up to. The interior of the Georgetown model boasts one level living at its best with an open and inviting floor plan featuring 9-foot ceilings with a large family room, separate dining room and a spectacular kitchen with a corner built-in pantry, stainless-steel appliances, upgraded cabinets with soft close doors and drawers, granite or quartz countertops and a washer and dryer package. This home includes 3 bedrooms and 2 full baths on the main level. There is plenty of room for expansion available in the basement area where you could option for a huge, finished rec room, 2 more bedrooms and another fully finished bathroom. The Primary Bedroom includes a vast walk-in closet, a luxury bath with ceramic tiled floor and shower walls, along with double vanity. This home is just waiting for you to make it yours! An easy commute to Baltimore, Washington DC, and historic Annapolis. This is a rare opportunity for new construction in the Rollings Knolls area. Make all your options and color selections at our design center. Let our skilled production team build your dream home. The pictures included with this listing show optional features and may be representative of likeness. Ask for details. Prices, terms, conditions, and availability is subject to change without prior written notice. Other Home Plans Are Available.

ANNAPOLIS

2175 GLENCREST CIRCLE - GEORGETOWN MODEL

3 Beds

2 Baths

1,757 Sq.Ft.

$799,990

MLS#: MDAA2124628

Welcome to this exquisite home nestled conveniently close to downtown Annapolis and Eastport. This former four bedroom model home with 2 car garage is most likely the largest house in Ambridge on a corner lot. The home has been freshly painted and carpeted and is situated on a nice corner lot in this premier community with downtown Annapolis in one direction and Quiet Waters Park in the other. Features include over 3,500 square feet on all three levels and 2,400 + finished square feet on first and second level. (The two car garage is not included in the 3,500 square feet.) Floor plans are attached. Sunny open floor plan featuring large kitchen with white cabinetry, granite and pantry, plus stainless steel refrigerator (8/2023, $2,400). Family room has wood burning fireplace and custom built-in cabinetry. Dining room also has custom built-in cabinetry with bump out window and newer chandelier. Hardwood throughout first level. Two level foyer. Large upper level features an open sitting area with skylight leading to four bedrooms including primary bedroom and bath. Fully unfinished lower level offers 1,100 square feet and awaits your finishing touches. Will sell some furniture upon request. Newer HVAC system (2021), irrigation system, and security system. From this location, you are close to some of the Bay's best cruising and fishing areas. Attractive destinations such as Baltimore's Inner Harbor, St. Michael's, Oxford, and Solomon's Island are only a short cruise away. Annapolis offers the perfect balance of small town charm and big world sophistication. Located just 5 miles to Route 50 and I-97 which provides direct access to Baltimore, BWI, Fort Meade/NSA and Washington, D.C. Don't let this opportunity slip away.
Owner Agent. There is no sign on the property. MDAA2123566 is the for lease listing for this property.

ANNAPOLIS

919 BERWICK DRIVE

4 Beds

2 Baths

3,346 Sq.Ft.

$799,900

MLS#: MDAA2123438

Luxurious penthouse condo with tons of natural light and views overlooking the fountain and plaza! 1285 square feet of living space encompassing a spacious Living room with fireplace, Kitchen with granite counters and plenty of cabinet space and 2 spacious bedrooms with ensuite baths. Every room boasts views and sliding doors onto a juliet balcony, perfect for letting in the fresh air and the cool evening breeze. Neutral finishes throughout and recently new refrigerator (1.5 years old) and HVAC unit (2 years old) creates peace of mind and a move-in ready blank canvas. Simplify your life with easy lock and go living. Fabulous 24/7 live concierge services, secure and monitored building, designated parking space and storage area. Even bills are streamlined since most utilities are included in the monthly condo fee. Enjoy the plethora of amenities that the Residences at Park Place provides including outdoor pool, courtyard for entertaining and grilling, hot tub, dog park, party room with billiards table, fitness room and many social activities. Perfectly located within close proximity of everything Annapolis has to offer; walk to the shops and restaurants of West and Main Streets as well as the Historic District, City Dock and the Naval Academy. Traveling or commuting is just as convenient by easily accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!

ANNAPOLIS

5 PARK PLACE 722

2 Beds

2 Baths

1,285 Sq.Ft.

$799,000

MLS#: MDAA2112456

PRICE ADJUSTMENT!!!! A life on the water that inspires! This cheerful contemporary home in sought-after Bay Highlands perfectly blends upscale living with relaxed coastal charm. With tall ceilings, abundant natural light, and beautifully landscaped grounds, it offers approximately 3,000 square feet of thoughtfully designed space that feels both open and inviting. Built in 1988 and freshly updated with new HVAC, fresh paint, and modern finishes, this home features three spacious bedrooms and two and a half baths. The kitchen is a true standout—equipped with stainless steel appliances, upgraded countertops, and plenty of space for casual dining. Skylights and expansive double-pane windows fill the home with natural light and capture serene views of Oyster Creek. The main level offers effortless flow between the kitchen, living, family, and sunroom spaces—all designed for easy entertaining or quiet evenings overlooking the water from the spacious rear deck. Upstairs, the primary suite is a retreat of its own, featuring a walk-in closet, sleek spa bath with walk-in shower, and a private balcony that opens to peaceful creek views. Two additional bedrooms provide flexibility for guests, a home office, or a creative studio. The finished daylight lower level extends your living space with a cozy TV room, workshop area, and walkout access—ideal for hobbies or recreation. Step outside to discover your own backyard oasis: lush landscaping, hardscaping designed for easy entertaining, and wide-open views of Oyster Creek thanks to the lot backing to community open space. With parking for three to four cars, a community dock for kayaking and paddleboarding, and proximity to Quiet Waters Park, Eastport, and downtown Annapolis, this property offers a lifestyle of connection, recreation, and tranquility all in one. Bay Highlands is truly one of Annapolis’ hidden treasures—an established waterfront community where neighbors gather, kids play freely, and every sunrise feels special. Imagine the magic of moving in just in time to create new memories and holiday traditions in this peaceful, picturesque setting. 1193 Bay Highlands Drive—more than a home, it’s a place to celebrate life on the Chesapeake and make every day feel like a getaway.

ANNAPOLIS

1193 BAY HIGHLANDS DRIVE

3 Beds

2 Baths

3,100 Sq.Ft.

$797,000

MLS#: MDAA2125180

New on site today

#MDAA2128904

ANNAPOLIS

8 SOMERSET COURT

4 Beds

3 Baths

4,115 Sq.Ft.

$780,000

MLS#: MDAA2128904

Welcome Home to Annapolis
Experience the coastal charm and vibrant lifestyle of Maryland’s Chesapeake Bay—where boating, sailing, and sunsets on the water are part of everyday life. Nestled within a highly sought-after school district, this light-filled beach-style chalet perfectly blends modern updates with the warmth of a true retreat.
Step through the inviting entryway into a bright, open floor plan. The main-level flex room offers endless possibilities—ideal for a home office, fitness studio, or game lounge. The beautifully remodeled kitchen showcases stunning Calacatta quartz countertops, a navy-and-white cabinetry duo, and stainless-steel appliances. Designed for both family gatherings and weekend entertaining, the kitchen flows seamlessly into the dining area and out onto a spacious deck overlooking more than half an acre of private, tree-lined yard—perfect for cookouts, bonfires, and starlit evenings by the outdoor fireplace.
When it’s time to unwind, retreat to four oversized bedrooms offering plenty of room to relax and recharge. From its thoughtful design to its serene setting, this Annapolis home captures everything you’ve been searching for in your next chapter. Schedule your private tour today and come see why life is better by the Bay.

ANNAPOLIS

920 OLD ANNAPOLIS NECK ROAD

4 Beds

2 Baths

2,552 Sq.Ft.

$760,000

MLS#: MDAA2126128

Time for a Lifestyle Upgrade — Welcome to GrandView at Annapolis Town Center! Step into elegance with this spectacular "Everest" model on the 6th floor — a rare opportunity to own one of the most coveted floorplans in the building. This stunning, move-in-ready home shows like a designer model and boasts an array of luxurious upgrades designed for both comfort and style. Enjoy two spacious primary suites, a guest powder room, and a versatile office/den ideal for remote work or quiet relaxation. The open-concept living and dining area features soaring 10-foot ceilings, gleaming hardwood floors throughout (no carpet!) and custom lighting that create a sophisticated, yet warm atmosphere. The gourmet kitchen is a chef’s dream, equipped with granite countertops, high-end KitchenAid black stainless steel appliances, and rich cabinetry. Additional highlights include a large laundry room, large closets for optimal organization, a newer HVAC system, and a private balcony overlooking the vibrant boulevard — the perfect spot to enjoy a glass of wine and live music during the center’s summer concerts. Located on the highly sought-after retail side of the building, you’ll enjoy a true urban vibe with direct access to the best of Annapolis Town Center — Whole Foods, Target, top-rated restaurants, cafes, and boutique shops, all just steps from your door. GrandView amenities include: two assigned garage parking spaces, concierge service, state-of-the-art fitness center, rooftop pool with panoramic views and secure entry and elegant common spaces. Just minutes to Historic Downtown Annapolis, the Annapolis Mall, Anne Arundel Medical Center, and with easy access to Route 50 and I-97 for commuting to D.C. or Baltimore. Experience elevated living at GrandView — this is a MUST-SEE unit!

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 606

2 Beds

2 Baths

1,682 Sq.Ft.

$755,000

MLS#: MDAA2127738

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