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
266
# of Listings
3
Avg # of Bedrooms
$529
Avg. $ / Sq.Ft.
$1,357,478
Med. List Price

Browse Annapolis Real Estate Listings

266 Properties Found. Page 2 of 18.

Ideally situated on the banks of Luce Creek with sweeping views down the Severn River, 1715 Porters Hill Road is a unique heritage property with over a century of history. Set on a 1.7 acre lot with 265 ft of waterfrontage, the property includes a large, hard-to-find boathouse that provides both charm and utility for all your waterfront adventures. The private pier has 7+ ft water depth and can accommodate a large vessel as well as an assortment of smaller boats. The tram makes access to the water effortless, and the entire property enjoys an exceptional privacy.
Steeped in its storied past yet thoughtfully updated for modern living, this retreat captures the perfect balance of historic charm and casual elegance. The heart of the home is a sunlit great room with original log walls and quarried stone fireplace, a vaulted ceiling, and expansive windows which frame water views at every turn. An adjoining den, with separate entrance option, is a perfect place to relax. This could easily become another main level bedroom with ensuite bathroom. The kitchen is striking under its vaulted ceiling accented by exposed beams. The custom cabinetry, GE Monogram stainless steel appliances and generous island give the space so much functionality while maintaining the artisanal character. The kitchen opens to the dining area overlooking the water. The table is anchored by a craftsman-style light fixture, and the entire first and second floors have beautiful wood floors. Step outside and you’re embraced by nature: multiple porches and decks overlook lush, manicured grounds that lead down to the water’s edge. 
The main-level primary suite is a true sanctuary, designed for privacy and tranquility. The bedroom, with a vaulted ceiling, has a screened porch overlooking the water. Two expansive walk-in closets offer custom organization systems that would make a clothing connoisseur smile.  The spa-like bathroom gets lots of natural light from the windows that frame the water, and the freestanding soaking tub is situated to enjoy this view. A dual-sink vanity, heated floors, generous walk-in shower with a built-in bench, and a spacious cosmetic area with dedicated seating make getting ready feel effortless and luxurious. A dedicated laundry area just off the hallway makes day-to-day living very easy. Part of the primary suite is a gracious office with gas fireplace and outdoor access. This is a totally flexible space: install a wall of bookshelves and you’d have a lovely library.
Upstairs, there are two generously sized bedrooms. One has water views and a waterside balcony; the other overlooks the lush landscaping out front. There is a hall bathroom.  A separate guest bedroom suite above the garage, complete with its own living area and luxe bathroom, is ideal for visiting friends and family who desire more privacy.  The Historical Context: Originally built in the 1880s, this log house was one of three identical structures used as hunting lodges. The logs of this original structure were re-purposed in the renovation. The construction of the log walls is one of great craftmanship, including sizing each log to be approximately the same diameter as others. Lore has it that around the turn of the 20th century, the Naval academy wanted to acquire more land by the academy and traded this peninsula for land across from College Creek. The Naval Academy superintendent, Admiral David Porter, could be where the name Porter’s Hill derived from. In the 1920’s, the Whitehead family – three brothers known for running bootleg liquor to Baltimore and Washington during Prohibition — used the property as a place to entertain and stop on the way to Baltimore. In the 1940s, the brothers’ exploits caught up with them, and the State of Maryland confiscated the Porters Hill peninsula. Through a unique trade involving the Jones family’s gravel pit (now the site of the 895 Tunnel), this private waterfront enclave found its next chapter.
#MDAA2142344

ANNAPOLIS

1715 PORTERS HILL ROAD

4 Beds

4 Baths

6,594 Sq.Ft.

$3,750,000

MLS#: MDAA2142344

Welcome home. Perfectly positioned at the end of Market Street, this rare waterfront residence offers an exceptional blend of privacy, design, and lifestyle. Located within an intimate six residence enclave, this fully reimagined contemporary brick townhome captures sweeping views of Spa Creek from every level, delivering a front row experience to Annapolis’ most iconic moments, from the Blue Angels to the holiday lighted boat parade. Completely rebuilt from the studs in the last few years with a refined nautical influence, the home spans four light filled levels, where thoughtful design and craftsmanship are evident throughout. Refinished hardwood floors run seamlessly from room to room, while custom steel stair elements made from sailboats, create a striking architectural focal point. An elevator services the main and upper levels, offering both convenience and ease of living. The main living level is both elegant and inviting, featuring a stunning half bathroom, spacious living room with a wood burning fireplace with a marble fireplace surround with custom surrounding built ins that look out to the water. The gourmet kitchen is designed for both everyday living and entertaining, offering high end appliances, a beverage refrigerator, and a dramatic marble waterfall countertop. Additional luxurious details include hidden hinges, walnut doors and tiles from Bali. Sightlines were intentionally designed to draw your eye straight through to the water the moment you enter. The upper level primary suite is a true retreat, offering panoramic water views and a spa inspired bath. An additional ensuite bedroom completes this level, along with a conveniently located second laundry area for effortless everyday living. The top floor provides two more generously sized bedrooms and a beautifully appointed full bath, ideal for guests. On the lower level, a fully equipped second kitchen, recreation space with gas fireplace, full bath with exquisite flooring, laundry, and storage create the perfect setting for extended stays or entertaining, with direct walk out access to the waterfront. Beyond the interiors, the lifestyle is equally compelling. A flagstone courtyard welcomes you home, while rare off street parking adds convenience for owners of this six townhome community. A deeded boat slip sits just steps from your door, offering immediate access to the water. Residents enjoy exclusive access to a heated gunite pool, beautifully maintained grounds, exterior maintenance including the roof, a floating dock, and kayak storage, all within this private community. From here, it is a short stroll to the shops and restaurants of downtown Annapolis, or take a scenic water taxi ride and be picked up just steps away from your front door. This is a rare opportunity to experience turnkey waterfront living with effortless access to everything that makes Annapolis extraordinary.
#MDAA2143742

ANNAPOLIS

5 MARKET QUAY

4 Beds

4 Baths

3,036 Sq.Ft.

$3,750,000

MLS#: MDAA2143742

Quintessential downtown Annapolis waterfront home on the sparkling waters of Spa Creek! This amazing property combines the best of both worlds;  the charming historic feel of a downtown Annapolis home with the premier waterfront lifestyle that every resident is looking for.  Nestled on a quiet street, this home is the perfect size for an easy to own, lock up and go property. With 3 bedrooms and 2.5 baths it has all the elements needed to enjoy life to the fullest; either as the perfect weekend retreat or permanent residence. The Annapolis area and the surrounding waterways are sure to entertain in every season. The upper level of the home is dedicated to the spacious Primary suite with unique sitting area and expansive roof deck.  Take in panoramic views of Spa Creek, Annapolis Harbor and Eastport.  An unparalleled vantage point for sunrise coffee or sunset cocktails.  The main level offers multiple cozy gathering areas including a formal living room with fireplace, home office and light filled gourmet kitchen with dining area.  The kitchen area flows effortlessly into the dining area and out onto the rear deck overlooking Spa Creek.  Perfect for gathers of all sizes and dining al fresco. The lower level provides an ideal retreat for family or guests with 2 spacious bedroom a full bath and a cozy family room with fireplace.  Head out to the charming covered patio to read a book or sip your evening cocktail or venture out on the water from the private pier. The amazing location is walkable to everything Annapolis has to offer and Spa Creek provides quick access to the Chesapeake Bay and beyond. Welcome Home!
#MDAA2109630

ANNAPOLIS

9 SHIPWRIGHT STREET

3 Beds

2 Baths

2,621 Sq.Ft.

$3,495,000

MLS#: MDAA2109630

1486 Downham Market is the ultimate Annapolis deep-water estate—designed for those who demand luxury, security, and boating excellence. Perfectly positioned at the mouth of Clements Creek—one of the safest hurricane holes on the Severn River—this home pairs architectural brilliance with one of the region’s most coveted waterfront settings.  A commanding 180’ pier with three boat slips, 50-amp power, and 11’ MLW welcomes yachts and sport boats alike—Hinckley, Viking, Boston Whaler, Pursuit, or Chris-Craft—this property can handle them all. Reinforced pilings are ready for lifts, making this a boater’s dream with full riparian rights. From here, you’ll be on the Severn and Chesapeake Bay in minutes.  Inside, walls of glass frame sweeping water views from nearly every room. Across three levels, the transitional design blends clean lines with warmth: hardwood floors, designer lighting, and soaring ceilings. The chef’s kitchen is fully outfitted with commercial-grade appliances, granite counters, and gas cooking, flowing into multiple living and dining areas anchored by a dramatic two-sided stone fireplace.  The primary suite is a true retreat—private sitting room and fireplace, a spa bath with skylight, soaking tub, glass shower, and custom walk-in closet. Additional ensuite and Jack-and-Jill bedrooms provide comfort and privacy for family or guests. The walkout lower level is built for entertaining with a rec room, wet bar, wine storage, gym, fifth bedroom, full bath, and a glass-wrapped sunroom ready for a hot tub retreat.  Outdoor living is extraordinary: multi-level decks, panoramic views, and serene waters that stretch toward the Severn and Bay. A brand-new septic system and advanced water treatment with reverse osmosis and UV protection offer peace of mind.  Set in the prestigious Downs on the Severn, residents enjoy two marinas, clubhouse, pool, tennis and pickleball, and a close-in location to Annapolis, D.C., and Baltimore.  Waterfront estates of this caliber almost never hit the market. 1486 Downham Market is ready now—bring your yacht, bring your lifestyle, and claim your place on the Severn.
#MDAA2119714

ANNAPOLIS

1486 DOWNHAM MARKET

5 Beds

4 Baths

5,260 Sq.Ft.

$3,250,000

MLS#: MDAA2119714

Set on a private peninsula with more than 450 feet of water frontage on Luce Creek, just off the Severn River, 1800 River Watch Lane offers a rare combination of modern sophistication and effortless single-level living. Meticulously renovated by the current owners, this contemporary rambler embraces water views from nearly every room. Guests arrive via a long, private drive and circular pea-stone court, surrounded by mature trees and mature landscaping. Inside, an open, sun-filled floor plan unfolds toward the water, creating a seamless connection between indoor living and the natural beauty of the setting.

The grand living room is the heart of the home, anchored by a dramatic wood-paneled cathedral ceiling and a floor-to-ceiling stone fireplace. A full wall of windows opens to an expansive ipe deck with hot tub that spans the width of the house—perfect for large-scale entertaining or quiet morning coffee overlooking the water. The dining room features custom acoustical paneling, while the adjoining family area with cathedral ceiling includes a gas fireplace and casual breakfast are—all capturing panoramic water views. The chef’s kitchen is both refined and functional, featuring marbled Silestone counters, Miele appliances (including double wall ovens, warming drawer, refrigerator/freezer, microwave, dishwasher, and induction cooktop), and a large walk-in pantry. A dedicated office with built-ins and an adjoining den/bedroom create valuable flexibility for working or hosting.

An architecturally striking skylit octagon, leads to the remaining bedrooms. The serene primary suite, framed by water views, offers a gas fireplace, tray ceiling, and an oversized walk-in closet. The spa-inspired bath includes a large double vanity, soaking tub positioned to capture the view, a generous walk-in shower, and a private sauna. Two additional bedrooms complete this wing—one with an ensuite bath—along with a third full bath, a separate laundry room, and powder room. Throughout the home, luxurious hardwood floors and large-format provide a clean, consistent aesthetic. A well-appointed mudroom and large two-car garage complete the residence.  Designed with sustainability and comfort in mind, the home features a state-of-the-art geothermal heating and cooling system, a new roof, and an upgraded water heater & treatment —providing exceptional energy efficiency.

Outdoors, the property transitions from elevated privacy access via a funicular that transports you to the to deep water pier with two boat lifts and approximately 8’ MLW. Situated high above Luce Creek—just off the Severn River—the home enjoys both long, sweeping views and the practical advantages of protected deep water. Whether boating to downtown Annapolis, heading out for an afternoon sail, or commuting toward Baltimore, BWI, the Eastern Shore, or Washington, DC, this location delivers exceptional convenience without sacrificing the tranquility of a private waterfront retreat.
#MDAA2130926

ANNAPOLIS

1800 RIVER WATCH LANE

3 Beds

None Baths

4,223 Sq.Ft.

$3,195,000

MLS#: MDAA2130926

This exceptional TO-BE-BUILT opportunity awaits in the coveted West Annapolis community —a rare 0.61-acre offering with endless potential. The custom new build was designed to seamlessly incorporate onto the expansive lot, providing your dream residence in one of the area’s most sought-after neighborhoods. The approved civil engineering plans by Drum, Loyka & Associates, LLC and architectural designs by Custom Designs Unlimited have city approvals secured and are awaiting permits to be pulled.

Cypress Homes, a well-known local builder, is prepared to construct the proposed 5-bedroom, 5.5-bath home designed for connection and comfort.  Featuring an exquisite exterior design, generously sized rooms, a thoughtful floor plan, and a harmonious connection between indoor and outdoor living.

The main level features a stunning great room with 2 story fireplace, a gourmet kitchen, and a luxurious primary suite with a spa-like bath. The upper level boasts 2 bedrooms each with ensuite baths.

The lower level has endless potential, currently offering 2 additional ensuite bedrooms with private patios, a recreation room, and a gym.  The conveniently located elevator accesses all levels.

The generous yard, screened porch, and multiple decks invite outdoor gatherings, summer barbecues, and relaxed evenings enjoying the vibrant West Annapolis lifestyle. Just beyond your doorstep, stroll to acclaimed restaurants, local pubs, charming boutiques, and convenient street-end water access. Ideally situated near Downtown Annapolis, Navy Stadium events, and the Naval Academy, the location also provides effortless commuter access to Route 50 and the Bay Bridge for Eastern Shore escapes or travel to Washington, D.C. Welcome Home!
#MDAA2135638

ANNAPOLIS

4 SHILEY STREET

5 Beds

5 Baths

5,312 Sq.Ft.

$3,090,000

MLS#: MDAA2135638

Repriced to Sell on 6.1.26 !! Open House This Saturday, June 6th 11:00am-1:00pm. Wake up to Severn River views, not dock maintenance! 812 Coachway is an all-brick waterfront estate in The Downs on the Severn, offering 6 bedrooms, 7 baths, and over 7,500 square feet of refined indoor-outdoor living. Thoughtfully updated to merge timeless architecture with modern luxury, nearly every room frames stunning Severn River views.

A two-story foyer leads to the office with custom built-ins, living and dining rooms, and a sunroom that opens to expansive decks and terraces. The gourmet kitchen features quartz counters, stainless steel appliances, induction cooktop, and a bay-window breakfast area flowing seamlessly into the family room with fireplace and full bar.

The upper-level primary suite includes a fireplace, brand new spa bathroom with wet room, and a private deck overlooking the water. Four additional bedrooms, multiple updated baths, and an upper-level laundry offer effortless comfort.

The walkout lower level is designed for gathering, with a recreation room, wet bar, exercise/guest suite, and direct access to the pool, patios, and fenced yard. Recent upgrades include new composite decks and refreshed landscaping for a resort-like, low-maintenance setting.

The Downs is one of Annapolis’s premier waterfront neighborhoods, offering:
• Two deep-water marinas with direct Severn River and Chesapeake Bay access
• Kayak & paddleboard launch areas
• Clubhouse, pool, tennis & pickleball courts
• Walking paths and peaceful, nature-rich surroundings

Think morning coffee on the water. Paddleboard before brunch. Wine on the deck at sunset. A serene, elevated waterfront lifestyle with a “waterfront yoga deck” feel and true *lock-and-leave* convenience. Boat slips are available at the marina 2 minutes away!
#MDAA2121546

ANNAPOLIS

812 COACHWAY

6 Beds

5 Baths

7,766 Sq.Ft.

$2,999,999

MLS#: MDAA2121546

Luxury living without the upkeep in Annapolis! This extraordinary residence combines two units into one expansive, stunning home in Annapolis Towne Centre offering over 3,400 square feet of impeccably finished living space on one level. Completely gutted to the studs and reimagined, this one-of-a-kind home places you right in the center of it all—and only minutes from Downtown Annapolis—yet feels like a private retreat from the world.

Designed for both grand entertaining and everyday comfort, the custom gourmet kitchen anchors the home and flows seamlessly into inviting living spaces. Sound-proof, glass-tempered doors allow rooms to transition effortlessly from open and connected to intimate and private. Thoughtful details include hidden, built-in Sonos speakers, exquisite moldings, tray ceilings, modern lighting, and a stunning blend of wood and marble flooring throughout.

Wine enthusiasts will appreciate the climate-controlled wine room, while the primary suite is a true sanctuary, featuring a glamorous dressing room, multiple custom closets with secret storage, and a spa-like ensuite bath with hand-cut mosaic tile flooring and an oversized walk-in shower with glass door linen closet. 

Featuring a fully integrated Lutron smart home system, this residence offers effortless control of lighting, motorized shades, audio, temperature, and security access.  Additional highlights include three additional bedrooms, two additional full baths, four garage parking spaces and two storage units. 

Residents enjoy world-class amenities including concierge service, fitness center, yoga studio, library, meeting rooms, elegant lounge spaces, and a spectacular rooftop pool—delivering a lifestyle that is as effortless as it is refined. 

Towne Centre has become the new heart of Annapolis — a vibrant destination where you’ll find everything you need, from grocery shopping and a premier fitness center to exceptional dining and upscale retail.
#MDAA2136232

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 406

4 Beds

3 Baths

3,364 Sq.Ft.

$2,999,000

MLS#: MDAA2136232

Life takes on a different pace in Oakwood, where the calm waters of Fishing Creek and the South River provide an idyllic backdrop and effortless access to the Chesapeake Bay. With 93 feet of shoreline, a private pier with multiple slips, and a substantial 25,000-pound boat lift, this property is perfectly suited for boating enthusiasts and those who appreciate the beauty and tranquility of the Chesapeake lifestyle.

Designed for both everyday comfort and effortless entertaining, the home offers an inviting open floor plan with seamless flow between the gourmet kitchen with center island, sunroom, soaring two-story living room, and adjacent family room. Walls of windows frame picturesque water views and fill the home with natural light. A versatile main-level room with an adjoining full bath provides ideal space for guests, a private office, or flexible living needs.

Upstairs, the spacious primary suite serves as a peaceful retreat with abundant windows capturing the ever-changing waterfront scenery, a walk-in closet, and an ensuite bath featuring dual vanities, a large shower, and a relaxing soaking tub. Two additional bedrooms share an ensuite bath and a fourth bedroom provides plenty of space for family and friends. The expansive space above the garage has been transformed into a fun Margaritaville-inspired bar and game room complete with a full bath. This exceptional area offers endless possibilities and could easily become a second primary suite, private guest quarters, or an in-law suite.

Outside, multiple entertaining spaces invite gatherings with family and friends while the lush lawn gently transitions to the water's edge. Whether hosting summer celebrations, launching a boat for a day on the Bay, or simply unwinding as the sun reflects across Fishing Creek, this property offers a lifestyle that feels like a vacation every day. A side-entry two-car garage and spacious driveway complete this exceptional waterfront offering in one of Annapolis Neck's most desirable communities. Welcome Home!
#MDAA2148158

ANNAPOLIS

3733 THOMAS POINT ROAD

5 Beds

4 Baths

5,082 Sq.Ft.

$2,980,000

MLS#: MDAA2148158

Perfectly positioned on one of the most coveted streets in Historic Annapolis, just steps from State Circle, the United States Naval Academy, City Dock, waterfront dining, boutiques, and yacht clubs, 238 King George Street offers a rare opportunity to own a completely reimagined luxury residence in the heart of Maryland’s capital city. Blending timeless historic charm with the modern conveniences today's discerning buyer expects, this exceptional home was extensively renovated and expanded in 2006–2007 and thoughtfully updated through 2025, including a new roof, HVAC systems, and water heater. Inside, four beautifully finished levels offer elegant living and entertaining spaces filled with natural light, custom millwork, rich hardwood flooring, high ceilings, and refined architectural details throughout. The gourmet kitchen opens seamlessly to inviting gathering spaces designed for both intimate evenings and large-scale entertaining, while the finished lower level with high ceilings and private walk-out entrance provides exceptional flexibility for guests, recreation, or a private office. The upper-level loft retreat offers additional living space ideal for guests, a studio, or a luxurious private sanctuary. Enjoy views of the iconic Naval Academy Chapel dome, a daily reminder of the unparalleled location and lifestyle this home affords. Rare off-street parking adds tremendous value and convenience, while the lock-and-leave nature of the property makes it ideal as a primary residence, weekend retreat, or executive pied-à-terre. Offered substantially furnished with only a few exclusions, this remarkable home provides the opportunity to move in and immediately begin enjoying the very best of Annapolis living. Luxury, history, walkability, and convenience converge at one of the city's most prestigious addresses.
#MDAA2147930

ANNAPOLIS

238 KING GEORGE STREET

4 Beds

3 Baths

3,750 Sq.Ft.

$2,950,000

MLS#: MDAA2147930

TO BE BUILT, luxury home on Back Creek adjacent to Eastport. Quiet dead end street. Only steps away from the community marina with deep water slips.  Permits in process for home and private pier. Primary suite on the main level.  5075 sq/ft of finished living space.  Intentionally designed large home that can also live small when guests are away. 5br 4.5 Bath with 2 car garage.  Offering includes 10' tall ceilings, White European Oak Floors, Furniture Grade Cabinets, Quartz counters, Sub Zero/Wolf Appliances, Screened porch with Outdoor fireplace. Contact LA to schedule a tour of the property. Builder maintains a model home by appointment only. Witness the refined details.  $10k in Free options for use of Builders approved lender and title company.  Visit Whitehall Building & Company's site for additional information. 100% VA financing available.
#MDAA2131890

ANNAPOLIS

703 B GLENDON AVENUE

4 Beds

3 Baths

4,466 Sq.Ft.

$2,950,000

MLS#: MDAA2131890

Welcome to 202 Wardour Drive! This classic 1940 Dutch Colonial offers timeless character, generous living space, and an unbeatable Annapolis location. Situated on a quarter acre lot with large front yard, the south facing location ensures sunny days ahead! Located in the elegant Wardour community which reflects the naturalistic style of its designer, Frederick Law Olmstead, Jr, with its mature trees, meandering roads and preserved open spaces that foster community connection.
Inside, the home features five bedrooms, two bathrooms, gorgeous oak floors (recently refinished in 2026), fireplace, bright sun-porch and large 12x 32 back deck. The south-facing orientation fills the home with natural light, creating a bright and cheerful atmosphere throughout. Recent improvements include freshly painted interior and exterior spaces, a newer roof approximately four years old, new porch benches, and a beautifully installed brick paver sidewalk that enhances the home’s curb appeal. A long driveway and rear detached garage provide ample parking and storage.
Residents benefit from access to seven community beach areas and a shaded walking trail traversing the neighborhood, that provide a tranquil retreat for adults and a natural wonderland to explore. Conveniently located within walking distance of the local elementary school, Navy Stadium, Annapolis Street shopping and dining, Historic Downtown Annapolis and offers easy access to Rt. 50 for commuters. With classic architecture, spacious interiors, abundant natural light, and an exceptional in-town location close to everything Annapolis has to offer, this is a rare opportunity to own in one of the area’s most beloved neighborhoods. Schedule your private tour today!
#MDAA2144980

ANNAPOLIS

202 WARDOUR DRIVE

5 Beds

2 Baths

2,100 Sq.Ft.

$2,765,000

MLS#: MDAA2144980

Perched above the Severn River in the gated waterfront community of Epping Forest, this exceptional property captures sweeping water views and effortless indoor/outdoor living just minutes from downtown Annapolis. Thoughtfully designed with an open floor plan and walls of windows, the home is filled with natural light, high ceilings, custom millwork and seamless sightlines to the Severn river from nearly every vantage point.

Expansive ipe decks with sleek cable railing extend the living space outdoors, creating the perfect setting for sunset entertaining or quiet mornings overlooking the water. The primary suite is a true retreat, complete with a private balcony overlooking the Severn; an idyllic perch for enjoying elevated river views and summer breezes. On the lower level, a covered flagstone patio offers an additional outdoor haven, ideal for relaxed evenings, gathering with friends or stepping directly out toward the waterfront.

Inside, beautifully appointed gathering spaces flow easily from the gourmet kitchen to the dining and living areas, offering both comfortable everyday living and gracious entertaining. Three spacious bedrooms, three full baths and two half baths are thoughtfully distributed across four finished levels, providing flexibility for guests, work from home needs or additional recreation space.

The private pier with deep water and two lifts, including a dedicated jet ski lift, invites endless days on the Severn, with quick access to Annapolis waterways and beyond. Ideally positioned close to Epping Forest’s renowned amenities, residents enjoy a clubhouse with waterside dining, marina, sandy beach, boat ramp, tennis courts, walking trails and a vibrant calendar of social events.

An additional 0.115-acre parcel on Sherwood Trail (Tax ID: 224010114205) conveys with the sale and offers convenient supplemental parking, providing easy access for the many guests who will be sure to come visit.

A rare opportunity to embrace panoramic river views, exceptional community amenities and the quintessential Annapolitan waterfront lifestyle. Epping Forest is a Special Tax District ($3,059.47 annually) with binding Rules and Regulations. Welcome Home!
#MDAA2137986

ANNAPOLIS

349 SHERWOOD TRAIL

3 Beds

3 Baths

3,185 Sq.Ft.

$2,550,000

MLS#: MDAA2137986

READY TO BUILD NOW!! Introducing an exceptional opportunity to build your dream home with a local custom home builder on a rare 2.19-acre homesite in the highly sought-after water-privileged community of Winchester on the Severn—a neighborhood where everyday living feels like a vacation. This thoughtfully designed custom home will offer over 6,700 square feet of finished living space, featuring 6 bedrooms, 6 full baths, and 1 half bath, along with a 3-car garage, blending timeless craftsmanship with modern luxury and functionality. The main level is designed with both comfort and entertainment in mind, showcasing an open-concept floor plan anchored by a gourmet kitchen featuring high-end appliances, an expansive workspace, and seamless flow into gathering spaces. A beautifully appointed butler’s pantry includes a built-in ice maker and is complemented by a walk-in pantry, demonstrating the careful attention to detail found throughout the home. A rare main-level bedroom with en suite bath, along with a dedicated private office, provides exceptional flexibility for guests, multi-generational living, or work-from-home convenience. Upstairs, you’ll find four generously sized bedrooms, each offering its own walk-in closet and own en suite bathroom —a rare and highly desirable feature. The primary suite serves as a luxurious retreat, complete with separate his-and-hers walk-in closets and a spa-inspired bathroom featuring a soaking tub and oversized walk-in shower. The finished lower level is designed for entertainment and relaxation, featuring a spacious recreation room, a dedicated theater room, and an optional bar area with its own pantry and possible wine storage room. An additional en suite bedroom on this level makes the space ideal for extended guests, in-laws, or a live-in nanny. Set on an exceptionally rare 2.19-acre homesite, the property offers endless possibilities for outdoor living, including space approved for a future pool, pickleball court, or custom outdoor entertainment retreat of your choice —creating the ultimate private backyard oasis. Life in Winchester on the Severn offers an unmatched lifestyle. Simply hop on your golf cart and head to one of the finest community beaches on the Severn River, where residents enjoy a playground, pavilion, sandy beach, swimming pier, kayak and paddleboard storage and launch, boat ramp, and breathtaking sunsets over the water. This is an extremely rare opportunity to create a custom residence in one of the area’s most desirable water-privileged communities—where luxury, space, and lifestyle come together seamlessly.
#MDAA2142274

ANNAPOLIS

1603 WINCHESTER ROAD

6 Beds

6 Baths

6,709 Sq.Ft.

$2,500,000

MLS#: MDAA2142274

Picturesque Craftsman-style waterfront cottage in Epping Forest! Mornings begin with coffee on the porch as the water glistens across Saltworks Creek and stretches out to the Severn River, while evenings are spent gathered by the firepit, watching boats drift by under painted skies. Welcome to effortless waterfront living in the private, gated community of Epping Forest where every day feels like a getaway and every detail is designed for ease.

This completely renovated property offers the perfect balance of charm, comfort, and low-maintenance living, making it an ideal full-time residence or lock-and-go retreat. New owner’s thoughtfully completed the whole house renovation in the last year, with additional second floor Restoration Hardware full bath, creating beautiful 2nd upper level bedroom suite, updated kitchen and appliances, new first floor flooring, custom designed kitchen pantry and primary bedroom closet by Chesapeake Closets, raised lower level ceiling to 10’, fresh paint inside and out, all decks and staircase to water polyurethaned, significant landscaping and hardscaping of entire property with expanded driveway to 3-4 cars, new Ring security system and Leaf Gutter system, and more! Previous owner recent improvements in last 1 to 2 years include, new second floor dormer, covered balcony, windows and flooring, new primary bedroom full bath and lower level full bath with Restoration Hardware, new 1st floor gas fireplace and mantel, new roof, new pressure treated stairs to water, new deep water 50’ floating dock with water and power. The home is move-in ready and designed to maximize both lifestyle and convenience.

Inside, tall ceilings and walls of windows invite natural light to pour in while framing the surrounding landscape and wide, open water views. The open floor plan creates an easy flow between the gourmet kitchen, dining area, and living room with fireplace, all seamlessly extending to the waterside covered porch, an inviting space for al fresco dining, morning breezes, or unwinding after a day on the water.

Upstairs, two ensuite bedrooms provide private retreats, including a serene primary suite with its own balcony overlooking the water, perfect for capturing sunsets and summer breezes. The lower level offers additional flexibility with a family room, guest bedroom, and full bath, ensuring plenty of space for visiting family and friends.

Outdoors, the boating lifestyle takes center stage. The recently built deep-water floating dock with a 50-foot slip, complemented by a dedicated mooring ball defensive, creates an exceptional setup for effortless days on the water with quick access to the Severn River, Annapolis Harbor, and the Chesapeake Bay beyond.

Epping Forest enhances the experience with a vibrant, amenity-rich setting, offering a clubhouse with waterfront dining, deep-water marina, sandy beach, boat ramp, tennis courts, and scenic walking trails, along with a full calendar of social events and clubs. All just minutes from downtown Annapolis and convenient commuter routes, this is a rare opportunity to enjoy a truly turnkey waterfront lifestyle in one of the area’s most cherished communities. Epping Forest is a Special Tax District ($2,934.96/yr.) with binding Rules & Regulations. Welcome Home!
#MDAA2139878

ANNAPOLIS

327 RIVERVIEW TRAIL

3 Beds

3 Baths

1,831 Sq.Ft.

$2,349,000

MLS#: MDAA2139878

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