One of the most popular communities provided by {{page_data.agentName}}

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

166

# of Listings

2

Avg # of Bedrooms

$499

Avg. $ / Sq.Ft.

$959,198

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

166 Properties Found. Page 4 of 12.

Time to Make a Lifestyle Change – Stunning & Fabulous at The GrandView!
Welcome to The Flagship, a unique and highly sought-after corner unit in the premier GrandView community. Perfectly positioned for the best location, views, and luxury, this residence offers an unmatched lifestyle in the heart of Annapolis Town Center. Step inside and be captivated by the wall of windows that flood the space with natural light and showcase panoramic views of Annapolis Town Center’s vibrant activity. Enjoy morning coffee or evening cocktails from your private, covered corner balcony. This 2-bedroom, 2-bath home is beautifully appointed with granite countertops, 10-foot coffered ceilings, hardwood floors, and custom window treatments. Recent upgrades include: New HVAC system, New stainless steel appliances, New bedroom carpeting, Updated lighting and black hardware through out. Additional features include an assigned storage unit and two reserved garage parking spaces.

Residents of The GrandView enjoy luxury amenities such as: Concierge services, Fitness center, and Rooftop pool with stunning city views. Live the walkable lifestyle! Stroll to Whole Foods Market, Target, fine dining, cafés, banking, and boutique shopping—all just steps from your door. You’re minutes from Historic Downtown Annapolis, Annapolis Mall, Anne Arundel Medical Center, and with easy access to Route 50 and I-97 for effortless commuting.

This is truly a must-see residence—a perfect blend of comfort, convenience, and modern elegance in one of Annapolis’ most desirable addresses.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1004

2 Beds

2 Baths

1,794 Sq.Ft.

$975,000

MLS#: MDAA2127946

Redevelopment opportunity in an established boutique shopping & business district. Value is in the land (approximately 15,000 sq. ft.) Being offered "as is - where is". Former location of Tara's Gifts at the gateway to West Annapolis. B1 zoning permits retail, office & residential use. Easy access to/from Rt. 50. Walkable to offices, restaurants, shopping, downtown Annapolis, USNA & Navy/Marine Corp. Memorial Stadium. Possible assemblage with adjacent 2 buildings at 2-4 Annapolis Street...gross rents totaling $20,700/Mo. from 6 retail & 2 residential tenants. Total land area for 2, 4 & 10 Annapolis Street is approximately 37,500 sq. ft. (0.86 acres).

ANNAPOLIS

10 ANNAPOLIS STREET

None Beds

None Baths

0.34 acres

$975,000

MLS#: MDAA2127370

Development opportunity in an established boutique shopping & business district. Value is in the land (approximately 15,000 sq. ft.). Being offered "as is - where is". Former location of Tara's Gifts at the gateway to West Annapolis. B1 zoning permits retail, office & residential use. Easy access to/from Rt. 50. Walkable to offices, restaurants, shopping, downtown Annapolis, USNA & Navy/Marine Corp. Memorial Stadium. Assemblage possible with adjacent buildings at 2 & 4 Annapolis Street grossing rent from 6 retail & 2 residential tenants totaling $20,700/Mo.

ANNAPOLIS

10 ANNAPOLIS STREET

None Beds

None Baths

2,064 Sq.Ft.

$975,000

MLS#: MDAA2127368

Welcome to 1909 Eleanor Ct, a stunning colonial featuring five bedrooms and three and a half bathrooms. You’ll fall in love the moment you walk in! Highlights include a large eat-in kitchen that opens to the family room, perfect for gatherings, plus a mudroom with ample storage. There’s even a cozy area off the kitchen ideal for a home office or homework station. The oversized owner’s suite boasts a custom walk-in closet and a spacious bathroom for the ultimate retreat. The fully finished basement includes a full bathroom, and the three-car garage provides plenty of space for vehicles and storage. All of this sits on a flat lot in a quiet cul-de-sac, offering both privacy and convenience.

ANNAPOLIS

1909 ELEANOR COURT

5 Beds

3 Baths

4,790 Sq.Ft.

$950,000

MLS#: MDAA2127206

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.

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

2,142 Sq.Ft.

$949,900

MLS#: MDAA2131620

Tucked away at the end of a quiet, secluded street off No Cherry Grove (one of the prettiest streets in sought after Homewood) is the home you have been waiting for! This exceptional 4 BR, 2.5 BA, 3 level Contemporary offers rare privacy while remaining within walking distance to West Street Library, shops and restaurants and nearby Downtown Annapolis. Built in 1980, the home features a highly desirable main level Primary Suite complemented by elegant formal Living and Dining Rooms, a spacious Family Room, 2 fireplaces and custom built-ins. The remodeled granite Kitchen offers stainless appliances, solid wood cabinetry and leads to adjacent Family Room which opens seamlessly to beautiful outdoor living with decking and patio, perfect for entertaining or just enjoying the peaceful setting. Finished Lower Level adds lots of square footage.

Set on a private, fully fenced lot, this home truly delivers PRIVACY, PRIVACY, PRIVACY- a rare find so close to the heart of Annapolis proper. Additional highlights include an oversized two car garage, circular driveway and generous storage throughout all three levels.

Offered fully furnished, this property has an impressive rental history, serving as a corporate rental for over 10 years, consistently commanding $6500/mo. This makes it an outstanding opportunity for investors or buyers seeking short term rental or executive rental potential, as well as a turnkey primary or second home.
A unique blend of seclusion, walkability and proven income, thisHomewood gem is truly one of a kind.

ANNAPOLIS

1403 COREY LANE

4 Beds

2 Baths

1,960 Sq.Ft.

$925,000

MLS#: MDAA2134282

New on site 4 days ago

GREAT OPPORTUNITY! Huge building offers two levels with office on main level and office on upper level, both units are vacant and ready to run your business as you rent the other unit out or combine both. Close to Annapolis Mall, Route 50 and much more!

ANNAPOLIS

2563 FOREST DRIVE

None Beds

None Baths

20,173 Sq.Ft.

$899,999

MLS#: MDAA2135848

Rare double-lot opportunity in water-privileged Annapolis Roads! This beautifully updated home at 1009 Old Bay Ridge Rd conveys with the adjoining parcel at 1011 Old Bay Ridge Rd for a combined 0.55 acres. Enjoy exceptional outdoor space, extensive hardscaping, ample parking, golf-putting green, and a large detached barn-style garage/outbuilding ideal for parking, boat storage, hobbies/workshop, or storage. The renovated main level offers two family rooms, dining room, updated kitchen, and a bright sunroom. Upstairs includes a primary bedroom with full bath access, plus three additional bedrooms and two more full baths. Finished lower level featuring additional living space, workspace, & storage. Annapolis Roads amenities include a private beach, boat ramp, kayak storage, playground, pavilion, firepit, and waterfront overlook with Chesapeake Bay views. This home is conveniently located within a short distance to downtown Annapolis, the United States Naval Academy, amazing restaurants, shopping, and plenty of fun activities. A unique chance to own a spacious property in one of Annapolis’s most desirable communities! Hurry to this one, it won't last long!

ANNAPOLIS

1009 OLD BAY RIDGE ROAD

4 Beds

3 Baths

2,845 Sq.Ft.

$899,000

MLS#: MDAA2132254

OPEN HOUSE HAS BEEN MOVED TO SATURDAY JANUARY 24TH FROM 1-3 PM
Situated on one of Historic Annapolis’ most desirable streets, this circa-1815 row house offers a rare combination of early American character, thoughtful renovation and enviable outdoor space, all just steps from the William Paca House and Garden.
The home opens to a gracious living room with hardwood floors and a substantial wood-burning fireplace, a space that feels both intimate and surprisingly generous. Unlike many homes of its era, an earlier renovation introduced a layout with a more open flow, while also allowing natural light to move easily from front to back. Toward the rear, a well-defined dining area transitions into a sunroom addition wrapped in glass, with a wall of sliding doors that open directly to the brick-paved courtyard and garden beyond. The result is a house that lives comfortably year-round, with multiple places to gather, work or unwind. The kitchen is tucked discreetly off the dining area, and features classic Quaker Maid wood cabinetry, natural gas cooking, a wall oven, and ample counter space. This galley layout functions efficiently while remaining true to the home’s character. A discreet laundry area with utility sink is conveniently located nearby.
Upstairs, two en suite bedrooms provide privacy and balance. The owner’s suite is a step-down retreat with double closets and a skylit bath that brings in soft, natural light. On this level, a charming nook anchored by the home’s second wood-burning fireplace offers flexible bonus space, ideal for a home office, reading room or creative retreat, helping the home live large.
Outdoors, the ample rear courtyard is a standout feature for a downtown Annapolis property. Designed with intention and deliberately chosen professional plantings, the brick terrace and garden create a peaceful counterpoint to the historic streetscape out front. The exterior of the home was freshly painted in 2023, and the interior has also been recently refreshed. The front-facing windows have been carefully restored, preserving the home’s historic integrity.
Owned and carefully stewarded by the same owner for more than 30 years, the home carries a well-documented history. Originally serving as both a cobbler shop and residence, elements of its early construction, including hand-forged nails, remain part of its story. Architectural drawings from a 1980 renovation by noted architect Chip Bohl are available for those who appreciate the provenance behind the home’s evolution.
Just moments from the waterfront, the U.S. Naval Academy, Maryland Avenue, and Main Street’s shops and restaurants, this home blends authenticity, history, and location in a way that is increasingly hard to find in Historic Annapolis.
For buyers who value authenticity, walkability and architectural integrity, this Prince George Street residence offers a rare opportunity to own a meaningful piece of Annapolis history beautifully adapted for everyday modern living.

ANNAPOLIS

167 PRINCE GEORGE STREET

2 Beds

2 Baths

1,590 Sq.Ft.

$875,000

MLS#: MDAA2132236

New Construction in Cape St. Claire. Current sales price is based on buyer getting a construction perm loan to purchase home. Please look at the documents section of the listing to see all standard features included with this home and all floor plans. Pictures shown in this listing are of a previous home built at 1216 Ramblewood Drive Annapolis, Md. also located in Cape St. Claire. Home is scheduled to be completed by April/May of 2026. This same floor plan will be constructed on this site. Please contact listing agent with any questions.

ANNAPOLIS

1217 HAMPTON ROAD

4 Beds

2 Baths

2,700 Sq.Ft.

$872,000

MLS#: MDAA2130056

Set within the sought-after, water privileged community of Annapolis Cove. This stately brick residence offers timeless style and serene connection to nature. Tucked away on the headwaters of Blackwater creek, the home enjoys private backyard framed by peaceful water views and lush natural surroundings. Morning light glimmers across the creek as blue herons and native birds glide by, ever-changing backdrop. the setting is quiet and restorative-ideal for those appreciate privacy, beauty, and a calming presence on Black Water Creek. Nestled in mature trees and screened by nature. Traditional 4/5 bedroom home features lots of welcoming spaces for all. Designed for both connection and relaxation.
Four bedrooms, three full baths and a half bath on the main floor. Full Lower walk out level features gas fireplace stove for those cozy nites around the recreation room and bedroom and bath. A rare retreat.

Annapolis Cove is a scenic waterfront community in Annapolis. It has a beautiful private marina on Lake Ogleton that opens to the Chesapeake Bay, just south of the mouth of the Severn River. The Cove has a waterfront park,recreational area with picnic tables, basketball court and a toddler playground overlooking the marina. Annapolis Cove Residents are able to join the Bay Ridge Pool and Swim team Each Summer. Bay Ridge pool is a private members only pool which is for Bay Ridge and Annapolis Cove Community Members. Annapolis Cove is a 10 minute drive from the Annapolis Historic district and less than five minutes from Quiet Waters Park.

ANNAPOLIS

3233 CHRISLAND DRIVE

5 Beds

3 Baths

2,518 Sq.Ft.

$849,900

MLS#: MDAA2132662

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. 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

2,580 Sq.Ft.

$799,990

MLS#: MDAA2129594

Rare opportunity to own a charming 2-unit building in the heart of Eastport, offering water views from both units. Each residence features its own private entrance and deck, perfect for enjoying the sights and sounds of small town living and serene surroundings. Thoughtfully designed, both units include a comfortable living area, full kitchen, spacious bedroom, full bath, and convenient in-unit laundry. Just a short walk to Historic Downtown Annapolis, this property is ideal for investors or enjoying one unit while renting the other. Experience the best of Eastport living—steps from restaurants, marinas, and the waterfront lifestyle. The downstairs is a licensed short-term rental, and the upstairs is a licensed long-term rental. May be subject to all future rentals.

ANNAPOLIS

320 CHESTER AVENUE

2 Beds

2 Baths

1,176 Sq.Ft.

$779,000

MLS#: MDAA2128698

Experience upscale urban living in this stunning 3rd-floor Everest model at Grandview, ideally located on the retail boulevard side of Annapolis Town Center. This residence offers a true city feel with unbeatable walkability to premier shopping and dining.
The open-concept living and dining area features bamboo flooring, a dramatic tray ceiling, and floor-to-ceiling glass doors leading to a private balcony filled with natural light. Elegant French doors open to a versatile bonus room, ideal as a home office or third bedroom.
The kitchen is designed for both entertaining and everyday living, showcasing stone and granite countertops, a professional-grade double oven, and a peninsula breakfast bar. A spacious laundry room and additional storage cage add convenience.
Two luxury bedroom suites each feature custom closet organizers. The primary suite includes a spa-inspired bath with a soaking tub and walk-in shower, while the second suite offers a double-sink vanity and walk-in shower—perfect for guests or flexible living.
Enjoy resort-style amenities including concierge services, fitness center, and a rooftop pool with social lounges, plus two assigned garage parking spaces. Walk to Whole Foods, Target, and top restaurants like True Food Kitchen and Cooper’s Hawk. Minutes from Historic Downtown Annapolis, Anne Arundel Medical Center, Annapolis Mall, with easy access to Route 50 and I-97.
A must-see for those seeking a luxury, maintenance-free lifestyle.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 309

2 Beds

2 Baths

1,681 Sq.Ft.

$770,000

MLS#: MDAA2135756

#MDAA2131464

ANNAPOLIS

524 RIDGE ROAD

4 Beds

3 Baths

2,944 Sq.Ft.

$769,900

MLS#: MDAA2131464

1 2 3 4 5 6 ... 12

Buyers resources

7 Reasons to Work with a Realtor

7 Principles For Home Buying Success

Getting a Mortgage To Buy a Home

Home Hazards Awareness

Key Items For Home Inspection

Questions When Buying a Condo

Questions When Choosing a Realtor

Sellers resources

8 reasons to work with a realtor

Calculating Capital Gains

Checklist for Better Showing

Cleaning Home For Sale

Improving Odds Of an Offer

Preparing Home for photoshoot

Selling Your Home for More $$

Buyers resources

BUYERS RESOURCES

Sellers resources

SELLERS RESOURCES

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

First Name

Last Name

Email

Phone

MLS Property Number

Your message

What is 3 + 4 ?

Reason for contacting?

Buying a home

Selling a home

Other

I agree to receive email communication and understand I can unsubscribe at any time.

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Accessibility Menu

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Email address (Must be valid)

Already have an account ? Login here

Continue your home search

Email address

First name First Name

Last name Last Name

Phone number (Optional)

Password

I agree to receive communications and understand I can unsubscribe at any time.

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service