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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
306
# of Listings
3
Avg # of Bedrooms
$474
Avg. $ / Sq.Ft.
$1,089,849
Med. List Price

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306 Properties Found. Page 6 of 21.

Come take advantage of this incredible opportunity! Discover an enchanting classic brick residence in Murray Hill— Lovingly maintained and beautifully detailed, this timeless home features solid plaster walls, hardwood floors, 8½‑foot ceilings, and graceful archways. The updated kitchen flows seamlessly into a versatile layout that can easily accommodate a first‑floor primary suite—currently styled as a family room with an office and adjoining full bath. Charming, intimate evenings come alive in the inviting living room, centered around a wood‑burning fireplace with an elegant mantel and built‑in bookcases. Step onto the tiled, screened porch for a tranquil retreat, and appreciate the practicality of a mudroom just off the kitchen. The spacious walk‑up attic offers abundant storage or future creative possibilities, while the large basement—complete with a separate entrance and workshop space—provides even more room to grow. Roof is 13 years old and HVAC units are less than 4 years old. Located just steps from Maryland Hall for the Performing Arts, home to the annual Annapolis Film Festival, the Annapols Symphony, art classes and live music. And only three blocks away, Amos Garrett Park awaits—perfect for launching your kayak or paddleboard or taking the boat taxi to City Dock! A rare opportunity to own a character‑filled home in one of Annapolis’s most beloved neighborhoods. Don’t miss it!
#MDAA2121372

ANNAPOLIS

637 CHASE STREET

3 Beds

2 Baths

4,333 Sq.Ft.

$1,168,000

MLS#: MDAA2121372

Sellers are offering $25,000 to go towards siding replacement. This beautiful property offers three levels of spacious, comfortable living in the neighborhood of Epping Forest. Walking through the front door, vaulted ceilings and natural light greet you in the dining/living room area off the kitchen. A main level bedroom suite offers convenience and a second suite upstairs boasts extra privacy. The Severn River can be seen through the trees off the double level deck which is accessed through the dining room, primary suite, or basement common room. On the bottom level, two bedrooms share a full bath and a common living space. Sliding doors add more natural light and additional exits to the lower deck. The private neighborhood beach and clubhouse offer peak enjoyment in the summer months! The club house offers family and golf cart friendly community for all ages! Ample storage, parking, and living space make this home unique in the gated community! HVAC replaced in October of 2020 Both decks replaced in December of 2020 Water treatment system replaced in February of 2022 Roof replaced in November of 2023 Buyer must review and acknowledge Epping Forest Constitution and Bylaws. See Documents.
#MDAA2095698

ANNAPOLIS

319 EPPING WAY

4 Beds

3 Baths

2,372 Sq.Ft.

$1,150,000

MLS#: MDAA2095698

Welcome to 210 Providence Road, a rare opportunity to own in one of the most desirable neighborhoods in Annapolis. Nestled on over 1.4 acres—the largest lot in the neighborhood—this beautifully landscaped home offers the perfect balance of privacy, natural surroundings, and convenience, located just minutes from the vibrant shops, restaurants, and waterfront charm of downtown Annapolis. This thoughtfully maintained residence features three bedrooms and two and a half bathrooms, designed with both comfort and elegance in mind. Hardwood floors run throughout the home, creating a timeless foundation for every room. The kitchen is appointed with stainless steel appliances, blending modern convenience with classic style, while the open layout flows seamlessly into spaces made for gathering with family and friends. A walkout basement adds versatility, offering endless possibilities for additional living, recreation, or storage. Beyond the home itself, the outdoor setting is truly special. Expansive grounds, mature trees, and lush landscaping create a private retreat where you can unwind, entertain, and enjoy the beauty of nature in every season. Whether it’s morning coffee on the deck, summer evenings spent under the stars, or simply enjoying the quiet of your surroundings, this property offers a lifestyle that feels worlds away yet keeps you connected to everything Annapolis has to offer. Life in this community is enhanced by a collection of outstanding amenities designed to bring neighbors together and take advantage of the Chesapeake lifestyle. The 25-yard pool overlooks Mill Creek Cove, providing the perfect backdrop for swimming, relaxation, and summer fun. For those who love life on the water, the three-pier marina offers access to boating, fishing, and kayaking just steps from your door. A recently built clubhouse serves as the heart of the neighborhood, hosting happy hours, social gatherings, and signature events, including an unforgettable Fourth of July extravaganza. 210 Providence Road is more than just a home—it’s a retreat, a community, and a lifestyle. With its combination of privacy, natural beauty, and access to one of Annapolis’s most dynamic neighborhoods, this property is truly one of a kind.
#MDAA2124482

ANNAPOLIS

210 PROVIDENCE ROAD

3 Beds

2 Baths

2,076 Sq.Ft.

$1,149,000

MLS#: MDAA2124482

English Tudor featuring a stone front patio for nature lovers and bird watchers. Surrounded by large trees for tons of shade and a 45 foot rear deck for large gatherings and rear lawn for play areas. Almost 4000 square feet of living space plus an oversized garage 24x25 with a floored attic space above for expansion or storage. Spacious kitchen with two sliders to rear deck, solid cherry cabinets, quartz island with smooth cooktop with built-in exhaust fan, stainless steel appliances. The great room has cathedral ceilings, wood beams and wide plank redwood siding, wood burning fireplace and slider to rear deck. First floor guest room features wood flooring and access to walk-in shower. Laundry room with loads of built-in shelving, commercial grade Maytag washer, Maytag dryer. Upstairs features high end neutral carpet, 3 bedroom, 2 full baths and generous closet space. The community has water privileges with fishing pier and canoe storage and sidewalks for dog walking or strolling the neighborhood. Convenient location for commuting to Baltimore or D.C. and 20 minutes to BWI Airport. Six miles to Downtown Annapolis for great shopping and restaurants.
#MDAA2117832

ANNAPOLIS

553 CHOPTANK COVE COURT

5 Beds

4 Baths

4,438 Sq.Ft.

$1,100,000

MLS#: MDAA2117832

Welcome to an exquisite single-family residence—a turnkey, move-in ready home just minutes from Historic Annapolis, major commuter routes, and marinas. Thoughtfully updated and designed for both daily living and grand entertaining, this property seamlessly blends refined finishes with functional living spaces. A stunning new gourmet kitchen with custom cabinetry, upgraded appliances and a large island, perfect for entertaining family and friends. Spacious family room with a fireplace. Generously sized bedrooms with beautifully renovated bathrooms. A fully finished lower level featuring an additional kitchen, a spacious bedroom, recreation room and an additional full bath making it ideal for guests or extended family. Walkout access to the rear yard. An expansive deck and a level and well-manicured backyard that backs to serene trees. Bedroom level laundry room. Generous amounts of storage and a garage that easily fits 2 cars.
#MDAA2119720

ANNAPOLIS

210 BOWEN COURT

5 Beds

3 Baths

4,880 Sq.Ft.

$1,025,000

MLS#: MDAA2119720

This stunning home, available for delivery in April, boasts high-end upgrades throughout. It features a first-floor owner's suite, plus three additional bedrooms on the second level, along with two full bathrooms and a spacious loft. The gourmet kitchen is a chef’s dream, complete with custom cabinetry and an open-concept design. The impressive two-story family room with soaring ceilings creates a dramatic focal point, while the finished basement rec room, featuring a wet bar with a refrigerator and sink, is perfect for entertaining. Experience luxury living at its finest—schedule your tour today! Photos for illustration purposes only. Agent must attend first visit.
#MDAA2103810

ANNAPOLIS

106 STILLY WAY

4 Beds

4 Baths

4,594 Sq.Ft.

$999,900

MLS#: MDAA2103810

Welcome to this exceptional former model home in the prestigious Monticello enclave—ideally located just moments from Annapolis’ finest dining, shopping, and commuter routes. This residence showcases endless upgrades and over 6,700 square feet of refined living across three spacious levels, blending timeless elegance with cutting-edge comfort. A dramatic two-story foyer with striking black-and-white marble flooring and designer lighting sets the tone upon entry. The formal dining room offers a sophisticated setting for entertaining and opens seamlessly to an outdoor deck, perfect for al fresco gatherings. The gourmet eat-in kitchen is a culinary dream, featuring high-end appliances, quartz countertops with a waterfall edge, and an open flow into the family and breakfast rooms—designed for effortless living. The main level includes an ensuite bedroom, ideal for guests or multigenerational living, as well as integrated smart features like electronic door locks, a whole-house sound system, and destination control thermostats. Upstairs, retreat to a luxurious Primary Suite complete with a private sitting area with fireplace, balcony, and an enviable walk-in closet with built-in storage. The spa-inspired bath offers a jetted soaking tub, new steam shower, dual vanities, and curated designer finishes. Three additional spacious bedrooms include an en-suite and a Jack-and-Jill bath—perfect for family or guests. The fully finished walk-out lower level is built for entertainment and flexibility, featuring a wet bar, recreation area, theater, and a private bonus suite for guests, hobbies, or office space. Additional features include an irrigation system, smart home technology, a 2-car garage, and access to Monticello's private amenities including a community pool and dog park—all in a tree-lined, beautifully maintained neighborhood.
#MDAA2116636

ANNAPOLIS

2000 MONTICELLO DRIVE

6 Beds

6 Baths

6,612 Sq.Ft.

$999,000

MLS#: MDAA2116636

Welcome to this beautifully maintained residence in the amenity-rich community of Kingsport in Annapolis. Tucked into a picturesque neighborhood known for its scenic walking paths, swimming pool, tot lots, community pier, kayak storage, tranquil ponds with fountains, and lush landscaping, this home offers an exceptional lifestyle both inside and out. Lovingly cared for by its original owners, this gem is now ready for its next chapter. From the moment you arrive, you'll be captivated by the charming front porch and the professionally landscaped yard, supported by an extensive irrigation system. Step inside to discover soaring ceilings, gleaming hardwood floors, and elegant moldings that highlight the home's architectural character. The main level is thoughtfully designed for both everyday living and entertaining, featuring formal living and dining rooms, a spacious kitchen with ample cabinetry and workspace, a dedicated office, a convenient laundry room, and a bright sunroom overlooking the peaceful backyard. Upstairs, you will find four generously sized bedrooms, including an impressive primary suite with tray ceilings, panoramic windows, and dual walk-in closets. The en suite bath is a true retreat, offering both space and style. The fully finished lower level is a true standout, offering endless flexibility with a game room, music room, fitness area, workshop/storage space, and a full bath. The addition of a full egress walkout provides direct access to the beautifully designed paver patio and backyard—ideal for outdoor enjoyment. Ideally located just minutes from shopping, downtown Annapolis, the U.S. Naval Academy, and offering easy access to Washington, D.C., and Baltimore, this home combines lifestyle, location, and luxury. Don’t miss the opportunity to make it yours.
#MDAA2122894

ANNAPOLIS

702 PEARSON POINT PLACE

4 Beds

3 Baths

6,321 Sq.Ft.

$989,500

MLS#: MDAA2122894

Welcome to 52 Primrose Hill Lane, the original model home in Craftmark’s Primrose Hill community — a hidden gem in the heart of Annapolis. Inspired by the area’s Georgian heritage, this residence offers nearly 4,000 sq ft of thoughtfully designed living space across three levels, blending timeless architecture with modern comfort. Inside, an open-concept main level features a gourmet kitchen with an oversized island, quartz counters, and upgraded finishes flowing seamlessly into spacious living and dining areas. Upstairs, generously sized bedrooms and a serene primary suite create a sense of comfort and retreat, while two en-suites provide options for generational living. The finished lower level offers flexible space for entertaining, work, or wellness, along with dedicated storage rooms. As the former model, this home showcases elevated design elements, including custom built-ins and a gas fireplace with a custom marble surround. Designer lighting, crown moldings, and a fully finished lower level reflect Craftmark’s commitment to quality and sophistication. Step outside to a private back patio, or enjoy the peaceful community open space with walking trail — a rare enclave that combines serenity with convenience. HOA services, including lawn care and snow removal, provide ease of living, while the location offers quick access to historic downtown Annapolis, Eastport, waterfront dining, recreation, and commuter routes to Washington, D.C. and Baltimore. 52 Primrose Hill Lane offers the character of a model home, the legacy of a storied Annapolis setting, and the ease of low-maintenance living — all in one elegant address.
#MDAA2124872

ANNAPOLIS

52 PRIMROSE HILL LANE

5 Beds

4 Baths

4,226 Sq.Ft.

$985,000

MLS#: MDAA2124872

Stunning contemporary in Winchester on the Severn featuring abundant windows that provide lovely views. Enjoy multi-level decks, patios, and custom hardscaping, complete with a private putting green and hot tub. Main level includes foyer, large sunroom, living room with stone fireplace - dining room combination, kitchen with granite countertops, main bedroom with adjoining full bath, 2 additional bedrooms and full bath in hall. The lower level includes another sunroom with exit to the rear yard, recreation room, study, and another very spacious room (potential 4th bedroom) with super bath and side exit. A real beauty! Updated drawing by appraiser showing larger sq ft is available for review) The Winchester on the Severn community offers a voluntary association fee of $260 per year for access to amenities, including a private beach, dock, canoeing, playground, and covered picnic pavilion . The community also has 2 different areas with boat slips that when available can be rented for an additional fee. The Chase Creek Swim Club is also nearby and joinable for an additional fee.
#MDAA2116724

ANNAPOLIS

1534 CIRCLE DRIVE

4 Beds

3 Baths

2,876 Sq.Ft.

$975,000

MLS#: MDAA2116724

Stunning Updated Colonial in a Water-Privileged Community! This beautifully renovated four-bedroom, two-and-a-half bath home features a custom kitchen with all-new cabinetry, Calcutta Quartz countertops, and sleek stainless-steel appliances, including dual ovens with a gas cooktop. The inviting family room is equipped with built-in surround sound speakers, perfect for entertaining. The luxurious primary suite offers a spa-like experience with a large shower featuring dual shower heads, a soaking tub, a custom border-lit mirror, and a towel warming bar for those chilly days. Convenience is key with a second-floor laundry closet. Step outside from the family room onto a spacious Trex deck that overlooks a large backyard. The property includes an attached two-car garage and a fantastic 30x50 detached two-story toy barn garage, complete with a car lift 10' doors and 13' ceilings and the potential to finish the upstairs space into a perfect in-law or teen apartment. This home also boasts a new roof, a freshly paved driveway, and all-new plumbing and insulation. Enjoy the perks of a water-privileged community with access to a sandy beach and a community dock. This home and Detached garage sits on a double lot with separate gravel road on backside for easy access for boats, RV's storage. This home truly has it all!
#MDAA2111664

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

3,078 Sq.Ft.

$950,000

MLS#: MDAA2111664

This contemporary home blends modern design with traditional touches, offering comfort, elegance, and function. A dramatic wall of glass in the living room frames views of birds, wildlife, and the home’s stunning landscape gardens. The vaulted ceilings create more elegances to this open-floor concept. The first-floor primary suite is complemented by a full laundry room on the same level, creating ease of living. Upstairs, a loft provides additional living space, while the home offers two additional bedrooms and 2.5 baths in total. The kitchen is beautifully tailored with quality finishes, and the full basement offers potential for even more finished living space. For car enthusiasts, the property features an oversized two-plus car garage with a dedicated car bay and work area, in addition to a separate two-car detached garage. Set on a beautifully landscaped one-acre lot, the home showcases diverse gardens designed to attract nature, creating a private retreat while remaining close to all the attractions of Annapolis. The community enhances the lifestyle with exceptional amenities including a pool, tennis, pickleball, and more.
#MDAA2121148

ANNAPOLIS

1698 SAEFERN WAY

3 Beds

2 Baths

2,648 Sq.Ft.

$950,000

MLS#: MDAA2121148

Welcome to your dream home in the exclusive Windfern Forest community—a private, water-privileged enclave of executive homes offering both tranquility and recreation. Nestled on a spacious .54-acre cul-de-sac lot, this well-maintained home offers approximately 5,100 square feet of living space. Inside, you’ll find four generously sized bedrooms and 3.5 bathrooms, including a luxurious primary bedroom suite that features an attached sitting room. The main level showcases hardwood floors adding warmth and sophistication, along with custom window treatments, cozy family room with fireplace, and a bright sunroom. A dedicated library/den/office with custom built-ins provides a productive and stylish workspace. The elegant formal dining room with its beautiful molding sets the stage for memorable entertaining. Enjoy the versatility of the lower-level recreation room plus bonus room and full bath—ideal for a guest suite, a home gym, or media space. You’ll also appreciate the abundant storage in the unfinished portion of the basement. Enjoy professionally landscaped grounds and access to kayaking, paddleboarding, and boat slips. Access to boat slips is available on a first-come, first-served basis. Conveniently located near shopping centers, restaurants, and major commuter routes, offering convenience without sacrificing peace and quiet. This home blends comfort, elegance, and lifestyle—making it a rare opportunity in a highly desirable setting.
#MDAA2114686

ANNAPOLIS

534 POST OAK ROAD

4 Beds

3 Baths

5,040 Sq.Ft.

$950,000

MLS#: MDAA2114686

Welcome to 1141 Mainsail Drive, a beautifully updated colonial nestled on a desirable corner lot in Anchorage, one of Annapolis’ most coveted waterfront communities. This move-in-ready 4-bedroom, 2.5-bathroom home blends timeless colonial charm with thoughtful modern upgrades. Just one block from the community’s 49-slip marina, boat ramp, kayak and paddleboard racks, outdoor pool, and half basketball court, this property offers an exceptional lifestyle both inside and out. Inside, you’ll find a traditional yet open layout floor plan with refinished hardwood floors on both the main and upper levels and tall windows that fill the home with natural light. The main level features a welcoming foyer, formal living and dining rooms, a powder room, and a family room with a freshly painted double-sided masonry wood-burning fireplace. The renovated eat-in kitchen boasts marble countertops, stainless steel appliances, and a gas line, seamlessly flowing into the casual dining area and family room—ideal for everyday living and entertaining. French doors lead to a charming brick patio, perfect for outdoor gatherings. Upstairs, the primary suite with an en-suite bathroom and three (3) additional bedrooms are complemented by another bathroom and a versatile den/home office nook. The fully finished renovated basement, completed in July 2025, adds valuable living space with high-performance waterproof Pergo flooring, a recreation room, home gym or office area, and a renovated laundry/utility room with 2021 washer and dryer and ample storage. Extensive updates include: roof, siding, gutters, and windows, new driveway and French drain system, new sump pump with backup battery system (July 2025), upgraded furnace, water heater, well pump, and sewer line. The attached two-car garage provides convenient interior access, and the .34-acre lot features mature landscaping and a sense of privacy rare in Annapolis. With only 106 homes, Anchorage is a close-knit, non-through-traffic community surrounded by wooded serenity and located just 3.5 miles to historic downtown Annapolis, 1 mile to Quiet Waters Park, and within 35 miles of D.C. and Baltimore. Don’t miss this rare opportunity to own a thoughtfully renovated colonial in this hidden gem of a waterfront neighborhood—homes here rarely come to market at this price point.
#MDAA2108692

ANNAPOLIS

1141 MAINSAIL DRIVE

4 Beds

2 Baths

3,264 Sq.Ft.

$949,000

MLS#: MDAA2108692

• Eclectic downtown location with 8 on-site parking spaces • Unit has a reception/bullpen area, 5 offices, a kitchen that seats 4, copy/fax room and 2 restrooms (one with shower) • Upgraded finishes and systems throughout • Close proximity to Maryland State House, Circuit Court, State Office Buildings, United States Naval Academy, Annapolis City Dock, and St. John’s College • Walking distance to Rams Head Bar & Grill, El Toro Bravo, Level, Tsunami, and various retail shops and services • Taxes for the unit are $10,040 annually • MX zoning, permitting uses of office, retail, restaurants, galleries, and laboratories.
#MDAA2110468

ANNAPOLIS

79 WEST STREET 1

None Beds

None Baths

1,971 Sq.Ft.

$940,000

MLS#: MDAA2110468

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