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237 Chatham Ln, Annapolis
$539,000
3 Beds ⋅ 4 Baths
**Sellers request offers by 2PM on Monday Oct 5th** Great value in Annapolis! You’ll smile the moment you walk into this beautifully renovated three-level home offering approximately 2,280 finished square feet, three bedrooms, 3.5 baths, and an inviting open floor plan designed for comfortable living and easy entertaining. Ideally located in a lovely neighborhood just minutes from downtown Annapolis, restaurants, and parks, this home offers a wonderful blend of convenience and neighborhood charm. The open foyer leads naturally into the main living spaces, where the living room flows into the dining area and features a wood-burning fireplace—a warm focal point for relaxing or entertaining. The beautifully renovated kitchen, completed in 2023, is both stylish and functional, featuring an oak island countertop, soapstone surround countertops, Fireclay brick tile, Samsung appliances, and soft-close cabinetry. Beyond the kitchen, the den and office provide flexible space for working from home, relaxing, or gathering. A newer slider opens to the fully fenced backyard, with fencing completed in 2025, and a generous expanse of level, usable lawn. The 2022 deck offers dedicated areas for grilling and outdoor seating. The lower level adds valuable finished space and storage. With brand-new carpet installed in 2026, the finished area can serve as a home gym, recreation room, guest space, or in-law area. A separate laundry area, unfinished storage, and full walk-out to the backyard add convenience and functionality. Major improvements include the 2020 roof, 2022 deck, 2023 kitchen and siding, 2025 fencing, and 2026 carpeting, offering a wonderful combination of style, functionality, and peace of mind in a convenient Annapolis location. Welcome Home!

237 Chatham Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

856 Boatswain Way, Annapolis
$570,000
2 Beds ⋅ 2 Baths
SPECIAL FINANCING OPPORTUNITY – POTENTIAL SAVINGS OF APPROXIMATELY $700 PER MONTH DURING THE FIRST YEAR! Don't miss this opportunity to own 856 Boatswain Way in Annapolis, listed at $575,000, in the desirable Heritage Harbour 55+ community! SPECIAL 2/1 INTEREST RATE BUYDOWN OPPORTUNITY! Qualified buyers may be eligible for a financing credit of up to 2.5% of the purchase price ($14,375) toward eligible closing costs or an interest rate buydown through Brittany Bobbs of CrossCountry Mortgage. With a 2/1 interest rate buydown, buyers could potentially save approximately $700 per month during the first year, with additional monthly savings during the second year! That's approximately $8,400 in potential first-year payment savings! Imagine what you could do with those savings! WANT TO UPDATE THE HOME AND MAKE IT YOUR OWN? RENOVATION FINANCING IS ANOTHER OPTION! For buyers who envision updating the kitchen, renovating the bathrooms, installing new flooring, or making other improvements, a renovation loan may be an excellent alternative! Qualified buyers may be able to finance both the purchase price and eligible renovations into one mortgage, allowing them to create the home they've always wanted. This is a separate financing option from the advertised 2/1 interest rate buydown. Ask about available renovation loan programs and how they could help you transform this home to fit your personal style and needs! WELCOME TO HERITAGE HARBOUR! Nestled in a peaceful, private setting backing to mature trees, this lovely single-family home offers comfortable one-level living with wonderful potential. The spacious floor plan features a living room with a cozy gas fireplace, dining room, kitchen, family room, two bedrooms, two full bathrooms, and a versatile den or home office. An attached two-car garage adds everyday convenience. Step outside onto the deck and enjoy the tranquility of the wooded setting, perfect for relaxing, entertaining, or enjoying your morning coffee. With its desirable layout and beautiful surroundings, this home offers a fantastic opportunity to add your own personal touches and truly make it your own! ENJOY THE HERITAGE HARBOUR LIFESTYLE! This sought-after 55+ community offers an exceptional array of amenities and activities, including golf, tennis, pickleball, canoeing, kayaking, and so much more! Conveniently located in Annapolis with easy access to Baltimore, Washington, DC, and BWI Airport, this home combines a peaceful setting with an active, engaging lifestyle. TWO FINANCING PATHS TO EXPLORE! Take advantage of potential monthly savings through the special 2/1 interest rate buydown offered by Brittany Bobbs of CrossCountry Mortgage, OR explore a separate renovation loan to update and personalize this home to your taste! Schedule your private showing today and discover the possibilities at 856 Boatswain Way! Buyers are not required to use Brittany Bobbs of CrossCountry Mortgage to have an offer accepted; however, buyers must use Brittany Bobbs to qualify for the advertised lender credit associated with the 2/1 buydown opportunity. Renovation financing is a separate, independent financing option and is not part of Brittany Bobbs' advertised 2/1 buydown offer. All financing incentives and estimated savings are subject to buyer qualification, loan terms, program requirements, and lender approval.

856 Boatswain Way, Annapolis

Listing courtesy of Boyle & Kahoe Real Estate. Contact:

2 Silopanna Ct, Annapolis
$525,000
4 Beds ⋅ 3 Baths
Pristine and move-in ready, 2 Silopanna Court offers just over 2000 square feet of flexible living space inside Annapolis city limits, minutes from Eastport and historic downtown. A well-planned addition expanded the home to include a spacious upstairs primary suite and a separate family room with an adjoining office area on the main level. The primary suite features a walk-in closet and a private bath, with sliding doors that open to its own balcony. Three additional generously sized bedrooms share a second full bath, keeping all four bedrooms together upstairs. A main-level powder room adds convenience for guests. A full wall of built-in shelving and cabinetry gives the living room character and ample storage. The kitchen features white cabinets and stainless steel appliances and opens to a dining area with sliding doors to the backyard patio. The family room provides space to spread out, while the adjoining office or sitting area accommodates working from home. Outside, the fenced backyard offers room to garden or play beneath mature trees. A broad paver patio extends the living space outdoors, with plenty of room for dining and gathering. A separate shed keeps tools and outdoor equipment neatly stored and out of sight. Just steps from the house, a wooded trail leads toward Spa Creek for waterside walks and opportunities to spot herons and turtles. Nearby waterfront parks include Amos Garrett, where a pier and water taxi pickup offer another way to enjoy Annapolis and reach Eastport or downtown. In the opposite direction, a footbridge connects to Truxtun Park and the city’s public pool. Maryland Hall is a short walk away, with West Street cafes and local restaurants close by. Historic downtown Annapolis offers shopping and live theater, along with waterfront dining and community events throughout the year. Welcome Home!

2 Silopanna Ct, Annapolis

Listing courtesy of Compass. Contact:

1182 Bay Highlands Dr, Annapolis
$540,000
3 Beds ⋅ 3 Baths
Welcome to 1182 Bay Highlands Drive in Annapolis! This solid home offers a great opportunity for buyers looking to make a property their own in an established Annapolis community. The major systems have been replaced within the past few years, providing a strong foundation for future improvements. Price is reflective of the current condition of the home. The home is ready for updating and TLC, including cosmetic improvements to the kitchen, baths, flooring, and finishes. With the major systems already addressed, buyers can focus on renovations and personal touches to bring out the home's full potential. The asking price is reflective of the home's current condition and the updates needed. Property is being sold strictly "AS IS." Seller will make no repairs. A great opportunity for buyers with vision who want to customize a solid home and build equity in Annapolis.

1182 Bay Highlands Dr, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact:

1030 Mountain Top Dr, Annapolis
$500,000
3 Beds ⋅ 3 Baths
Beautifully appointed rancher in the sought-after Cape St. Claire community of Annapolis, just one block from the Magothy River and the Chesapeake Bay! Step inside to a spacious main level featuring gleaming hardwood floors and a bright, open living room centered around a tile-surround wood-burning fireplace with a reclaimed-style mantle and custom open shelving. The flowing layout leads seamlessly into the dining area, offering ample storage and direct access to a screened-in deck, perfect for indoor-outdoor living. The kitchen is thoughtfully designed with granite countertops, a classic subway tile backsplash, 36” cabinetry, and stainless steel appliances. The primary suite provides a comfortable retreat with crown molding, a generously sized closet with an organization system, and a private en-suite bath complete with a walk-in shower and updated vanity. Two additional bedrooms and a well-appointed hall bath complete the main level. The finished lower level expands your living space with plush carpeting, built-in shelving, a dedicated workshop, gym area, and a utility space featuring a convenient powder room, ideal for guests, a home office, or multigenerational living. Enjoy outdoor living in the fully fenced yard with a patio and secure storage, perfect for entertaining or relaxing. Conveniently located near major commuter routes, including US-50 and I-97, for easy access to Annapolis, Baltimore, and beyond. Ask about the ASSUMABLE MORTGAGE with a 3.25% INTEREST RATE!

1030 Mountain Top Dr, Annapolis

Listing courtesy of Northrop Realty. Contact:

2522 N Haven Cv, Annapolis
$500,000
2 Beds ⋅ 2 Baths
Welcome to refined, effortless living at 2522 N Haven Cove, nestled within the sought-after 55+ community of Heritage Harbour in Annapolis. This beautifully maintained 2-bedroom, 2-bath residence offers a spacious and inviting floor plan designed for both everyday comfort and gracious entertaining. The heart of the home is the updated eat-in kitchen, creating a welcoming space for morning coffee, casual meals, and gathering with friends. An attached one-car garage adds everyday convenience, while the thoughtfully designed layout provides the flexibility to create a home office, den, or private retreat. Here, the lifestyle extends well beyond your front door. Heritage Harbour offers an exceptional array of amenities designed for active, social, and carefree living—from golf, tennis, and pickleball to canoeing and kayaking. The Lodge serves as a vibrant gathering place, featuring indoor and outdoor pools, fitness facilities, a library, card room, and more. Ideally located in beautiful Annapolis with convenient access to Baltimore, Washington, DC, and BWI Airport, 2522 N Haven Cove offers an appealing blend of comfort, recreation, convenience, and community. Come discover a home where every day can feel a little more like a getaway.

2522 N Haven Cv, Annapolis

Listing courtesy of Taylor Properties. Contact:

626 Edwards Rd, Annapolis
$574,900
4 Beds ⋅ 2 Baths
Price Improvement Incredibly maintained home in the sought-after water-privileged community of Beechwood on the Burley. This two-level home offers comfortable living, a spacious outdoor setting, and an ideal Broadneck Peninsula location just minutes from downtown Annapolis and with easy access to Route 50. The established community offers water access, a marina, playground, and peaceful neighborhood setting, with convenient back-road access to downtown Annapolis. Inside, the home has been well maintained and thoughtfully updated with refinished hardwood floors, fresh paint, updated lighting, and new carpet. The upper level features a comfortable open-concept layout with a living room that flows into the dining area and kitchen. Granite countertops, beautiful cabinetry, and a center island with seating create a welcoming kitchen with plenty of workspace. Sliding glass doors open to a composite deck overlooking the flat, fully fenced backyard, where mature landscaping provides privacy and a lovely backdrop for outdoor living. The primary suite features a private ensuite bath, accompanied by two additional bedrooms and a full hall bath. The lower level adds valuable living space with a family room centered around a propane gas fireplace, an office/fourth bedroom, laundry room, and access to the attached garage. Ample storage throughout adds to the home's everyday functionality. Beechwood on the Burley is a voluntary HOA community with access to a waterfront park, community dock with slips, playground, and picnic area along the water. The neighborhood's quiet roads and surrounding farmland create a peaceful setting for walking, running, and cycling, while the home's location provides easy access to Annapolis, Broadneck schools, shopping, dining, and major commuter routes.

626 Edwards Rd, Annapolis

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

13 Spa Creek Lndg Unit A2, Annapolis
$506,000
1 Beds ⋅ 2 Baths
Nestled within the serene embrace of nature, enjoy fabulous waterfront views of Hawkins Cove and Spa Creek from this stunning 1-bedroom, 1.5-bathroom second floor condominium in the highly sought-after community of Shearwater in Eastport. With a contemporary coastal architectural style, this home is a perfect blend of sophistication and warmth. Step inside to discover an open floor plan that seamlessly integrates the living and dining areas. Natural morning light floods the space through the kitchen creating an inviting atmosphere throughout. The flat has an upgraded refrigerator, new microwave, new washer&dryer, HVAC, heat pump and air handler all in aprox 2024. The home features gleaming living room floors, and a gourmet kitchen designed to elevate your culinary creations. The bedroom suite is a private and cozy retreat with a luxurious ensuite bathroom. The exterior of the property is equally impressive, boasting a private balcony that overlooks the lush landscaping and the waterfront, providing a peaceful escape right from your terrace. This truly is a nature watchers’ paradise. In December, celebrate the famous Eastport Yacht Club annual Parade of Lights in style by your cozy wood-burning fireplace. In Spring/Summer enjoy the easy breeze with family and friends with your favorite libation. For water enthusiasts, the community offers direct access to Hawkins Cove and Spa Creek, complete with a private dock site and multiple slips for boating, fishing, and kayaking adventures. Surrounded by partly wooded areas and mature trees, the lot features a harmonious blend of nature and luxury, creating a serene environment for relaxation and recreation. It offers seamless access to the Chesapeake Bay and beyond. Your luxury lifestyle features the choice to relax poolside, play tennis/pickleball on the courts, or take a water taxi from the docks to enjoy the stunning array of restaurants, events, the arts and much more. Welcome home, your Annapolis dream has come true!

13 Spa Creek Lndg Unit A2, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

1017 Hyde Park Dr, Annapolis
$500,000
4 Beds ⋅ 2 Baths
Inside the Annapolis city limits, on a cul-de-sac, this Dutch Colonial pairs four bedrooms and two full baths with a fully fenced yard and about 1,928 finished square feet on three levels. A bedroom and full bath on the main level give guests their own space or make room for a home office, and three more bedrooms and a second full bath are upstairs. The fully finished basement adds room for a rec room, gym, or office. End the day in the steam shower with full body sprays, then light the wood-burning fireplace and let the blower carry the heat through the room. Out back, a deck steps down to the fenced yard, and a shed adds storage. The driveway parks two cars. Wilshire sits off Forest Drive, a short drive from the trails and waterfront at Quiet Waters Park, the restaurants of Eastport, the Annapolis Maritime Museum, and City Dock. Route 50 and the Bay Bridge put Washington, DC, Baltimore, and the Eastern Shore within reach, for the commute or for the weekend. Ask your agent about a lender closing-cost credit of up to $2,000 for applications by December 31, 2026, and no lender fees on VA loans.

1017 Hyde Park Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

1178 Glenwood Dl, Annapolis
$550,000
4 Beds ⋅ 2 Baths
BUYER’S CHOICE! Up to $10,000 seller credit may be available with an acceptable offer and mutually agreeable terms. Beautifully updated split-foyer home nestled on a gorgeous corner lot in the sought-after Cape St. Claire community of Annapolis. Offering an exceptional combination of modern updates, thoughtful improvements, and outstanding community amenities, this move-in ready home has been meticulously maintained inside and out. Inside, you'll enjoy modern fixtures, recessed lighting, granite countertops, and an updated kitchen featuring stainless steel appliances, including a refrigerator, dishwasher, and electric range replaced in 2022. The kitchen flows seamlessly onto a brand-new wood deck (2023, freshly stained in 2026), creating the perfect space for outdoor dining, entertaining, or simply relaxing. The inviting living room is centered around a beautifully renovated wood-burning fireplace (2023), while major system upgrades provide added peace of mind, including a new HVAC system (2024) and a whole-house humidifier (2025) for year-round comfort. The main level offers three bedrooms, including a primary suite with a private bath and two additional bedrooms with a shared hall bath. The finished lower level features a spacious flex area that can easily serve as a recreation room, home office, workout space, guest area, or potential fourth bedroom, along with a dedicated laundry area and convenient side-entry mudroom. Step outside and discover extensive outdoor improvements completed between 2022 and 2024. The property has been professionally regraded and enhanced with retaining walls, a stone walkway, additional gravel parking, and a completely restructured driveway offering improved functionality and expanded parking. An engineered drainage system, including underground front-yard downspouts and a complete backyard French drain, helps keep the property dry and functional throughout the seasons. Thoughtfully selected native, non-invasive flowers and shrubs provide beautiful color and interest throughout the year. Located in the highly desirable Cape St. Claire community of Annapolis, Maryland, residents enjoy access to outstanding neighborhood amenities, including a private community beach, community marina, boat ramp, fishing and crabbing pier, playgrounds, parks, and community events throughout the year. Conveniently located just minutes from downtown Annapolis, Broadneck Park, Sandy Point State Park, the Chesapeake Bay, the U.S. Naval Academy, shopping, dining, waterfront attractions, and everyday conveniences. Commuters will appreciate easy access to Route 50, I-97, Baltimore, Washington, D.C., Fort Meade, and BWI Airport. Whether you're looking for a beautifully updated home, a move-in ready property with major system upgrades, or the lifestyle that comes with living in one of Annapolis' premier water-access communities, this exceptional Cape St. Claire home offers the perfect opportunity to enjoy the very best of Maryland's Chesapeake Bay lifestyle.

1178 Glenwood Dl, Annapolis

Listing courtesy of Redfin Corp. Contact:

1155 Spruce Tree Ln, Annapolis
$542,900
3 Beds ⋅ 2 Baths
Welcome to this beautifully updated Cape St. Claire home, where extensive improvements, stylish finishes, and comfortable living spaces come together in a property that has been carefully maintained inside and out. At the heart of the home is an updated kitchen featuring newer appliances, 42-inch cabinetry, quartz countertops, a custom backsplash, and a farmhouse apron sink. The home features two full bathrooms, including one that was completely renovated from top to bottom with a new tub, tile, flooring, toilet, vanity, and sink. The second full bath has also been refreshed with new flooring, vanity, and sink. Newer luxury vinyl plank flooring and carpeting add a fresh, cohesive feel throughout the interior, while all-new custom window treatments installed throughout the home in 2026 provide a polished finishing touch. The finished lower level offers valuable additional living space with the flexibility to function as a recreation room, home office, or a combination of both. A fireplace adds warmth and character, creating an inviting setting for working, relaxing, or entertaining. A dedicated mini-split system installed in 2025 provides independent climate control for this level. The home has benefited from a substantial list of recent improvements, including a new main-level HVAC system installed in 2024, Hardie siding and shutters in 2025, replacement windows in 2022, and a roof replaced in 2018. The home also includes a garage with a new door installed in 2025. A security system was added in 2026, and an owned whole-house water treatment and softener system was installed in 2024, providing added convenience and value for the next owner. Outdoor living is equally appealing. A new deck completed in 2026 provides an ideal setting for dining, entertaining, or relaxing outdoors, while the fully fenced yard offers added privacy, security, and flexibility for pets or play. An expanded driveway and parking area installed in 2025 adds valuable everyday functionality and additional off-street parking. Tucked along a quiet, lightly traveled street with just five homes, the property enjoys a more private neighborhood setting while remaining only a few blocks from the Cape St. Claire community beach. The location also offers convenient access to Annapolis, shopping, dining, recreation, and major commuter routes while retaining the neighborhood atmosphere that makes Cape St. Claire so sought after. The home is served by the highly regarded Broadneck school district. With an updated kitchen, one fully renovated bath, a refreshed second full bath, extensive recent improvements, newer major systems, dedicated climate control on both finished levels, a garage, and substantial exterior upgrades already completed, this home offers the opportunity to simply move in and enjoy. Years of investment, care, and thoughtful enhancement have created a property where very little remains for the next owner to do.

1155 Spruce Tree Ln, Annapolis

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

218 Wintergull Ln, Annapolis
$549,000
4 Beds ⋅ 4 Baths
Gorgeous 4 level townhome situated on a premium, landscaped lot with water views. Every level highlights the connection to nature and privacy in this well-maintained, thoughtfully designed home. The ground level features a one car garage with storage shelves and a spa-like ensuite bedroom that leads to a private screened porch and fenced backyard. Perfect for guests, this space evokes relaxation and privacy. The main level offers a spacious family room, a gourmet kitchen, and large dining area that leads to a deck with views of the backyard oasis. Options for entertaining here are endless, with comfortable spaces for all to enjoy. The bedroom level offers a unique primary bedroom suite with ample closet space, sitting room/second bedroom, and upgraded primary bath with a luxury shower, double vanity, and soaking tub. The water view is prominent on this level. The bonus loft level provides an additional bedroom or office/flex space and a full bath. The community dock is a short walk away. With hardwood flooring on each level this home shows exceptionally well and is just waiting for its next occupants. Welcome Home!

218 Wintergull Ln, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

2604 Foremast Aly, Annapolis
$569,000
3 Beds ⋅ 4 Baths
The one you've been waiting for. An elegant townhouse which offers a harmonious blend of luxury and comfort, perfectly suited for those who appreciate low maintenance living with thoughtful upgrades, designed for an effortless, comfortable lifestyle. Meticulously maintained and upgraded by both the previous and current owners, the residence spans 2,088 square feet and showcases a traditional architectural style, enhanced by the brick front. Step inside to discover a warm and inviting interior with high-end finishes. The spacious living area features rich wood floors, crown moldings, floor to ceiling windows, plantation shutters, beautiful paneled walls, all the details that create a beautifully curated home with an atmosphere of quiet luxury. The gourmet kitchen is a culinary enthusiast's dream, equipped with stainless steel appliances, including a five-burner gas cooktop and double ovens. The expansive island and table space invite gatherings, while recessed lighting adds a touch of modern elegance. The home boasts three generously sized bedrooms, including a luxurious primary suite complete with a walk-in closet and beautifully appointed en-suite bathroom with a soaking tub and shower. An additional full bath upstairs is shared by the two other bedrooms and enjoy the convenience of a bedroom level laundry room. The cozy fireplace in the lower living area is a focal point, serving as the perfect retreat for relaxing evenings or a private home office. Outside, the property backs to trees and the deck offers an ideal space for outdoor relaxation or entertaining. The attached rear-entry garage with additional parking in front provides convenience for you and your guests. Adding to peace of mind, the roof is one year old, new washer, nearly new dryer, hot water heater in 2022 and brand new garage door and opener. This residence is more than just a home; with a prime location, easy access to commuter routes, and move in ready appeal, it embodies a lifestyle of comfort, where every detail has been thoughtfully curated. Experience the perfect blend of welcoming elegance in this exceptional property, where you can create lasting memories in a truly inviting setting.

2604 Foremast Aly, Annapolis

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

138 Cranes Crook Ln, Annapolis
$599,900
3 Beds ⋅ 4 Baths
Located in the well-known community of Riva Trace, this rarely-offered end-unit townhouse presents single-family privacy with its enchanting gardens and lush landscaped, irrigated surround. Once inside, you will enjoy 2,550 sq. ft. of thoughtfully designed living space on 3 levels, including 3 spacious bedrooms and 3.5 bathrooms. Featuring a classic layout with separate entertaining spaces, including a living room with soaring ceiling and natural light, a formal dining room, and a cozy family room off the kitchen with a wood-burning fireplace, inviting warmth and comfort on cooler evenings. The fully finished lower level is full of possibilities! Perfect for providing additional flex space, or can be used as an income producing apartment w/separate entry for a live-in child/parent/tenant. Recent upgrades include a newer HVAC unit (2020), washer/dryer, stove, refrigerator, brand new carpet & renovated lower level. Owned solar panels keep electricity costs low--major bonus! Enjoy the tranquility of Gingerville Cove, a picturesque creek just a short stroll from your door, where you can unwind by the water's edge by kayaking, canoeing or indulging in leisurely walks along the scenic paths. Close to all routes & shopping; minutes from town & restaurants.

138 Cranes Crook Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

2566 Glen Cv, Annapolis
$599,000
3 Beds ⋅ 2 Baths
Welcome to 2566 Glen Cove, a beautifully updated three-bedroom, two-bath home offering a rare opportunity to enjoy the Heritage Harbour lifestyle without the age restriction. While this property is not age-restricted, owners have the option to join Heritage Harbour through a social membership and enjoy access to its many amenities. Inside, the home is warm, inviting, and thoughtfully updated, highlighted by a stunning brand-new kitchen completed in 2026 featuring quartz countertops, stainless steel appliances, and beautiful finishes. Wood floors flow through the home, complemented by updated bathrooms, a separate dining room, and a classic wood-burning fireplace that creates a welcoming focal point for the living space. A spacious three-season sunroom provides the perfect place to relax or entertain while overlooking professionally designed landscaping by Cindy Shuart of Harmony Gardens. An irrigation system makes maintaining the beautifully curated grounds effortless. Additional highlights include a two-car garage and a new architectural shingle roof installed in 2026 with a transferable warranty, offering peace of mind for years to come. Beautifully maintained, thoughtfully improved, and surrounded by mature landscaping, 2566 Glen Cove offers comfortable Annapolis living with the added opportunity to become part of the vibrant Heritage Harbour community.

2566 Glen Cv, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

1309 President St, Annapolis
$540,000
3 Beds ⋅ 2 Baths
Price adjusted to reflect market response. AND it's open 10/31 & 11/1 ! There's history here. In the 1940s, the Meade family built a number of homes on President Street and in Hillsmere — Meade Street bears their name. For the first time, the family will be passing on this home, one of the last one still in family hands, to new owners. Original wood trim, high ceilings, and wood floors pair with a surprisingly open floor plan for its age. The third bedroom and kitchen were added in the 1960's. The daughters' bedroom was the upper level for many years. A detached garage with an attached screened porch is perfectly positioned for outdoor entertaining. The yard is large and fenced. This home only needs the new owner's personal touches to make it once again a forever home!

1309 President St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

1311 President St, Annapolis
$550,000
3 Beds ⋅ 1 Baths
Open House Sunday 11/01/26. 1 PM to 3 PM. This charming Cape Cod home in the desirable Eastport neighborhood offers a perfect blend of comfort and convenience. With 1,532 sq. ft. of well-maintained living space, this delightful residence features three spacious bedrooms and a full bath, ideal for relaxation. The kitchen is equipped with modern appliances, including a built-in microwave, range, and dishwasher, making meal prep a breeze. Set on a generous 0.21-acre corner lot, the property boasts a cleared, level yard, perfect for outdoor gatherings or gardening. Enjoy the serene street view while being just moments away from local parks and community amenities. The neighborhood is known for its friendly atmosphere and proximity to excellent schools, ensuring a nurturing environment for all. With convenient parking options and easy access to public services, this home is a wonderful opportunity to embrace a vibrant lifestyle in a welcoming community. Experience the warmth and charm of Eastport-your new home awaits!

1311 President St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

1197 Carrs Rd, Annapolis
$555,000
3 Beds ⋅ 2 Baths
ASK HOW YOU COULD SAVE ON YOUR MONTHLY MORTGAGE PAYMENT WITH A POTENTIAL RATE BUYDOWN THROUGH OUR PREFERRED LENDER! YOUR PRIVATE ACRE IN ANNAPOLIS! Discover a rare opportunity to enjoy peaceful, country-style living with the convenience of Annapolis nearby. Set on approximately one acre of beautifully landscaped grounds, this unique property offers privacy, versatility, and room to spread out, just minutes from Sandy Point State Park, the Chesapeake Bay, and routes toward downtown Annapolis and the Bay Bridge. Enjoy outdoor living at its best with mature landscaping, hardscape walkways, a newer Trex deck, brick patio, fully fenced yard, garden areas, storage shed, and outdoor shower. Inside, vaulted ceilings enhance the living and family rooms, while wood flooring throughout much of the main living area and comfortable main-level living create a welcoming feel. The kitchen features granite countertops, a subway tile backsplash, and ample cabinetry. Need space beyond the main house? A separate office/studio structure with its own electrical panel, heat pump, and efficiency kitchen offers exciting flexibility for a home office, creative studio, workshop, or other workspace. One of this property's standout features is the expansive, newly asphalted driveway with parking for 15+ vehicles, ideal for those with work vehicles, equipment, trailers, recreational vehicles, or frequent guests. Additional updates include a new well installed in January 2026, a refrigerator replaced in 2024, a hot water heater replaced in 2020, and a washer and dryer less than two years old. Surrounded by natural beauty and wildlife, with nearby walking paths providing access toward the water, this property offers a lifestyle that's increasingly hard to find. The former pool area provides additional outdoor potential; the pool is currently non-operational and conveys AS-IS. Looking for land, privacy, parking, and flexible space without giving up Annapolis-area convenience? This is your opportunity! Schedule your private tour today and ask about the potential rate buydown.

1197 Carrs Rd, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

126 Spring Place Way, Annapolis
$549,900
3 Beds ⋅ 4 Baths
Nestled in the charming community of Riva Trace, this delightful townhouse offers a perfect blend of comfort and convenience. Built in 1990, this traditional-style home features a classic brick front and wood siding, exuding warmth and character from the moment you arrive. With 2,323 square feet of thoughtfully designed living space, this residence is ideal for those seeking a cozy retreat in a vibrant neighborhood. Step inside to discover a spacious interior that invites you to unwind. The main level boasts an inviting layout, perfect for both entertaining and everyday living. Gather around the fireplace on chilly evenings, creating lasting memories with loved ones. The fully finished daylight basement adds versatility, providing extra space for a home office, playroom, or media area. The home features three generously sized bedrooms and three full bathrooms, ensuring ample space for relaxation and privacy. A convenient half bath on the main level adds to the functionality of the home. The attached garage offers easy access and additional storage, making life a little simpler. Riva Trace is not just about the home; it's about the lifestyle. The community is rich with amenities designed to enhance your everyday experience. Enjoy leisurely strolls or invigorating jogs along the scenic paths, or challenge friends to a game on the basketball or tennis courts. The association takes care of essential services, including exterior building maintenance, insurance, and snow removal, allowing you to focus on what truly matters-enjoying your home and community. With a boat ramp nearby, water enthusiasts can easily access local waterways for a day of fun on the water. Riva Trace is conveniently located, offering easy access to local shops, dining, and recreational opportunities. Whether you're exploring nearby parks or enjoying the vibrant local culture, you'll find everything you need just moments away. This townhouse is more than just a property; it's a place to call home, where comfort meets community. Don't miss the opportunity to make this inviting space your own in the heart of Riva Trace.

126 Spring Place Way, Annapolis

Listing courtesy of ExecuHome Realty. Contact:

2123 Beach Village Ct Unit T2, Annapolis
$565,000
2 Beds ⋅ 2 Baths
Direct, unobstructed views of Chesapeake Bay define this terrace-level home in Chesapeake Harbour. The two-bedroom, two-bath condominium features an open living and dining area centered around a fireplace, plus a kitchen with granite countertops, a subway-tile backsplash, and white cabinetry. A patio at the front and another at the rear provide two distinct outdoor spaces. The primary bedroom is well-appointed and includes direct patio access and a generously sized walk-in closet. A second bedroom, a full hall bath, and in-unit laundry complete the interior. The current floor plan measures approximately 1,267 square feet of finished interior space. Chesapeake Harbour is a gated waterfront community with 24-hour security and convenient access to downtown Annapolis. Amenities include a private beach, marina, two pools, tennis and pickleball courts, walking paths, kayak access and storage, and waterfront dining within the community. Few homes in this community see the water this directly. This home offers sweeping views of the Chesapeake Bay from the living room to the patio. This breathtaking view awaits you at 2123 Beach Village Ct, Unit T2. Welcome Home!

2123 Beach Village Ct Unit T2, Annapolis

Listing courtesy of Compass. Contact:

1164 Latrobe Dr, Annapolis
$525,000
4 Beds ⋅ 2 Baths
Professional photography coming soon…. Welcome to 1164 Latrobe Drive, perfectly positioned in the heart of the sought-after waterfront community of Cape St. Claire! Located just around the corner from the peaceful Lake Claire Beach, this spacious raised rancher offers three bedrooms, a versatile bonus room, two full bathrooms, and nearly 2,000 square feet of living space. The updated kitchen features granite countertops and stainless steel appliances, while hardwood flooring, crown molding, recessed lighting, and a comfortable family room with fireplace add warmth and character throughout. Major improvements include an architectural-shingle roof, water-treatment system, well pump, and HVAC replaced in 2023. Outside, enjoy a fenced backyard, off-street parking, and easy access to everything that makes Cape St. Claire such a special place to call home. This amenity-rich community offers multiple beaches and parks, three marinas with community boat slips, a boat ramp, fishing piers, playgrounds, sports courts, a clubhouse, and an active neighborhood atmosphere. The Cape St. Claire Shopping Center, Broadneck Trail, local schools, and everyday conveniences are also nearby. Whether you enjoy boating, kayaking, fishing, relaxing by the water, or simply being part of a true community, this home delivers the Cape lifestyle you are looking for!

1164 Latrobe Dr, Annapolis

Listing courtesy of Anne Arundel Properties, Inc.. Contact:

14 A Dorsey Ave, Annapolis
$585,000
4 Beds ⋅ 4 Baths
Priced at $600,000 and supported by a recent appraisal of $665,000, this brand new Annapolis home presents a rare opportunity to purchase with built in value from day one. Appraisal available for review. Special Financing Opportunity: Seller is offering a 2-1 interest rate buydown for qualified buyers, subject to lender approval and loan program requirements. Participation is optional and available to all eligible buyers. Welcome to 14 A Dorsey Avenue, a brand new home in Annapolis designed for both everyday living and easy entertaining. The main level is completely open, bringing the living, dining, and kitchen spaces together in one bright, functional layout. Large windows provide abundant natural light, while recessed lighting throughout adds a clean, modern finish. A convenient half bath completes the main level. Upstairs, the primary suite features vaulted ceilings and a private full bath. Two additional bedrooms and another full bath provide flexible space for family, guests, or a home office. The top floor offers a private fourth bedroom ideal for a guest suite, workspace, or separate retreat. The finished lower level adds even more usable living space, complete with a full bathroom and flexibility for a rec room, office, or guest area. Enjoy the confidence of new construction with new systems, finishes, appliances, and mechanicals throughout. Located just off West Street, this home offers an exceptionally walkable Annapolis setting and convenient access to downtown restaurants, shopping, and waterfront attractions. Easy access to Route 50 provides a convenient commute to Fort Meade, BWI Airport, and the greater DC/Baltimore corridor.

14 A Dorsey Ave, Annapolis

Listing courtesy of LPT Realty, LLC. Contact:

1915 Towne Centre Blvd Unit 303, Annapolis
$599,000
2 Beds ⋅ 2 Baths
MOTIVATED SELLER WILLING TO PAY ONE YEAR OF CONDO FEES ($15,408) FOR BUYER WHO PRESENTS ACCEPTABLE PURCHASE CONTRACT! Discover a luxurious lifestyle in this exquisite 2-bedroom, 2-bathroom residence nestled in the prestigious Grandview at Annapolis Towne Centre. This contemporary corner "Davenport" unit boasts an open floor plan with 10' ceilings, enhanced by elegant crown moldings and recessed lighting, creating a warm and inviting atmosphere. The gourmet kitchen features upgraded countertops and high-end appliances, including a built-in microwave, wall oven, and sleek Miele Induction cooktop, perfect for culinary enthusiasts. There is also a den that makes a great home office or flex space. Step onto the private balcony to enjoy serene views or unwind in the community's rooftop pool or elegant bar. The building offers exceptional amenities, including a fitness center, concierge service, and a stylish bar/lounge. Enjoy the convenience of in-unit laundry and assigned parking with electric vehicle charging stations available. With its prime location (easy access to shopping, dining, downtown Annapolis, Naval Academy, marinas etc.) and luxurious features, this home is a perfect blend of comfort and sophistication, inviting you to embrace an exclusive lifestyle. Experience the best of modern living in this exceptional property.

1915 Towne Centre Blvd Unit 303, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

785 Rolling View Dr, Annapolis
$550,000
4 Beds ⋅ 3 Baths
Welcome to 785 Rolling View Drive… If you’ve been waiting for a home that gives you space, outdoor living, community amenities, and access to the water without the waterfront price tag, this is it!!! 4-bedroom, 2.5-bath split foyer sits in one of the Broadneck Peninsula’s most recognizable water-privileged communities. Off-street parking, covered front porch, and a comfortable layout designed for everyday living and entertaining. The main level features an open living room and dining room combination, with a separate kitchen equipped with stainless steel appliances, including a newer refrigerator, stove, microwave, and dishwasher. From the dining area, step outside onto the oversized deck—the perfect spot for summer gatherings, morning coffee, grilling, or simply enjoying the peaceful setting. Three bedrooms are located on the main level, including a primary bedroom with a walk-in shower, along with a full bath. The lower level includes a fourth bedroom, family/rec room with wood-burning fireplace, separate laundry room, half bath, and walkout access to the rear yard. The backyard offers a private, secluded feel backing to a ravine, creating a natural buffer and peaceful outdoor setting. Major updates include: newer roof, Central A/C, flooring and updates throughout (2026). Cape St. Claire. This isn’t just a neighborhood—it’s a lifestyle. Residents enjoy access to multiple community beaches, three marinas, boat ramps, parks, recreation facilities, piers, and countless ways to enjoy the water. Go boating, launch a kayak, spend the afternoon at the beach, fish from the pier, or simply enjoy everything this unique community has to offer. Shopping and restaurants are conveniently located within the community, while Annapolis is just a short drive away. Perfect for commuters; convenient access to Washington, D.C., Baltimore, and Fort Meade. Come see why 785 Rolling View Drive is more than just an affordable Annapolis home—it’s an opportunity to live the Cape St. Claire lifestyle. Schedule a private showing today!!!

785 Rolling View Dr, Annapolis

Listing courtesy of Douglas Realty LLC. Contact:

402 S Cherry Grove Ave, Annapolis
$575,000
4 Beds ⋅ 3 Baths
***Sellers will consider offering a 2-1 interest rate buydown credit (saving the buyer over $600/month in Year 1) with an acceptable offer, giving buyers a significantly lower initial monthly payment without compromising on purchase price!*** Welcome to Heritage, a sought-after Annapolis community where space, comfort, and convenience come together! This beautifully refreshed three-level Colonial offers four bedrooms, multiple living spaces, a huge fully fenced backyard, and an impressive list of recent updates—making it truly move-in ready. Step inside to fresh paint, new carpet and LVP flooring, updated fixtures and hardware, and a bright, welcoming layout designed for everyday living and entertaining. The updated kitchen features freshly painted cabinetry and a brand-new refrigerator and opens to the family room for an easy, connected flow. Formal living and dining rooms provide additional space to gather, while the fully enclosed sunroom with casement windows offers a wonderful spot to relax and enjoy views of the backyard. A convenient half bath and mudroom with laundry hookups complete the main level. Upstairs, you’ll find four generously sized bedrooms. The spacious primary bedroom features two closets, while the second and third bedrooms share a Jack-and-Jill bath with a brand-new shower. An additional full hall bath adds even more flexibility for busy mornings and overnight guests. The lower level expands your living space with a partially finished recreation room featuring new drywall and recessed lighting—ready for movie nights, a game room, home gym, office, or whatever suits your lifestyle. A large storage and utility room includes additional laundry facilities, and a waterproofing system installed in 2023 comes with a lifetime warranty for added peace of mind. Outside, the expansive fully fenced backyard is ready for entertaining, gardening, play, or simply enjoying more room to spread out. A composite deck and storage shed add even more functionality. Additional improvements include replacement windows and a roof replaced within approximately the last 10 years. And then there’s the location! Heritage residents enjoy access to community amenities including a pool, clubhouse, fields, and a footbridge over Spa Creek—all while being conveniently located near the shops, restaurants, waterfront, and unmistakable charm of Downtown Annapolis. With its generous space, extensive updates, fantastic backyard, and Annapolis location, this is a home you’ll want to experience in person. Welcome home!

402 S Cherry Grove Ave, Annapolis

Listing courtesy of Compass. Contact:

633 Snow Goose Ln, Annapolis
$550,000
4 Beds ⋅ 4 Baths
* VA Assumable Loan Option * Nestled in the prestigious Waters Edge at Woods Landing, this exquisite townhouse embodies the perfect blend of elegance and comfort. Built in 2000, this Colonial-style residence showcases timeless architecture with a traditional flair, offering a warm and inviting atmosphere that feels like home from the moment you step inside. Spanning 2,044 square feet, this meticulously maintained interior row townhouse features four spacious bedrooms and four well-appointed bathrooms, including two full and two half baths. As you enter, you are greeted by an abundance of natural light that flows through the well-placed windows, highlighting the rich brick and combination exterior. The open-concept living area seamlessly connects to the dining space, creating an inviting environment for gatherings. The heart of the home is the gourmet kitchen, equipped with modern appliances and ample counter space, perfect for culinary enthusiasts and casual cooks alike. Retreat to the luxurious primary suite, a serene haven featuring generous closet space and an en-suite bathroom that exudes spa-like tranquility. Each additional bedroom offers comfort and privacy, ensuring that everyone has their own personal sanctuary. Step outside to discover a charming outdoor space, ideal for morning coffee or evening relaxation. The attached garage provides convenience and security, while the driveway and additional parking options ensure ample space for guests. Living in Waters Edge at Woods Landing means embracing a lifestyle of exclusivity and leisure. Enjoy the tranquility of the community while being just moments away from vibrant local amenities, shopping, and dining options. This property is not just a home; it's a lifestyle choice that offers the perfect balance of luxury and comfort. With its excellent condition and high-end features, this townhouse is ready to welcome you into a life of elegance and ease. Experience the charm and sophistication of this remarkable property-your dream home awaits. Dual HVAC from February 2026 and 2023 , hot water heater is 2023 , roof is 12 years old with 30 year shingles.

633 Snow Goose Ln, Annapolis

Listing courtesy of Douglas Realty LLC. Contact:

1424 Regent St, Annapolis
$529,900
4 Beds ⋅ 3 Baths
Welcome to 1424 Regent Street, where modern style meets everyday comfort. This beautifully updated home offers exceptional curb appeal with a spacious driveway, a brand-new sprinkler system, and a fully fenced backyard featuring a large deck—perfect for entertaining, relaxing, or enjoying outdoor living. Step inside to discover a stunning custom-designed living room highlighted by a striking gold and white accent wall that creates a warm, sophisticated focal point. The adjoining dining area flows seamlessly into the show-stopping custom kitchen, complete with stylish cabinetry, gorgeous quartz countertops, and designer finishes that make cooking and gathering a true pleasure. The spacious primary suite features its own en-suite bathroom featuring custom designer finishes. An additional beautifully renovated full bathroom upstairs offers both style and convenience for family and guests. Throughout the home, you'll find thoughtfully designed custom bathrooms and quality updates that create a move-in-ready experience. The lower level offer additional entertaining space with a stone fireplace, as well as a bedroom and a full bathroom. With its modern upgrades, designer touches, functional layout, and inviting spaces, 1424 Regent Street is a home you'll be proud to call your own.

1424 Regent St, Annapolis

Listing courtesy of Allfirst Realty, Inc.. Contact:

709 Skippers Ln, Annapolis
$590,000
3 Beds ⋅ 4 Baths
Assumable 4.25% VA loan!! Experience Ultimate Flexibility with this Versatile and Spacious Contemporary Townhome offering Unique Zoning flexibility , 3 Finished levels with 3,016sf, and a Rare Live/Work Opportunity located in Village Greens of Annapolis! Operate a boutique business, studio, or professional office right from your street-level commercial space with no commute - previously a boutique shop - with a convenient Kitchenette/Wet Bar area and Half Bath. Upstairs on the Main Living Level, discover an upscale, open-concept layout flooded with natural light and fabulous Designer Touches, Crown Molding, Plantation Shutters, Gorgeous Wood Floors and a Half Bath. The Beautiful Gourmet Kitchen features a large Island, Bright White Cabinets, Stainless Appliances and Quartz Counters in addition to the Spacious Dining area, and Inviting Living Room, Cozy Gas Fireplace and Deck create the perfect hub for Entertaining! Retreat to the Upper Level offering a Serene Primary Suite with Amazing Attached Bath and Walk-in Closet in addition to the 2 Spacious bedrooms, accompanied by another full bath and a den/flex space. This unit has been Meticulously maintained including a new AC unit (Oct 2025) and a freshly painted 2 Car Attached Garage featuring high-temp epoxy flooring and extra storage and plenty of parking. Located just minutes from historic downtown Annapolis, major commuter routes, dining, and the waterfront. Live, work, and play without compromise! Schedule Your Showing Today!

709 Skippers Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

40 Munroe Ct, Annapolis
$539,900
3 Beds ⋅ 1 Baths
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:

1210 President St, Annapolis
$524,999
3 Beds ⋅ 3 Baths
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:

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