Old Annapolis Neck, MD homes for sale & real estate

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COMING SOON

ABOUT THIS HOME
Old Annapolis Neck, MD Homes for Sale
Welcome to 143 Stilly Way, a barely-lived-in, one-year-young showpiece in Annapolis’ sought-after Parkside Preserve, offered in true mint condition and completely move-in ready. This is not a builder sale—it is a fully completed, meticulously upgraded home with every structural bump-out, every design enhancement, and every premium finish already in place. No waiting, no selections, no construction phase—just move in and enjoy. The Fitzgerald model was executed at the highest level, delivering expansive, light-filled interiors that feel polished, intentional, and finished. The open main level showcases exceptional flow for everyday living and entertaining, anchored by a ful

$1,295,000

6 beds5.5 baths5,370 sq ft

143 Stilly Way, Annapolis, MD 21403

5,208 sq ft lot • 2 garage spots • Built 2024

(410) 263-8686

COMING SOON

$398,000

3 beds2.5 baths1,392 sq ft

972 Breakwater Dr, Annapolis, MD 21403

$250 HOA • 2 parking spots • Community pool

(410) 224-2200

COMING SOON

ABOUT THIS HOME
Old Annapolis Neck, MD Homes for Sale
Welcome to 406 Harbor Drive, an exceptional residence in the heart of Hillsmere Shores, one of Annapolis’ most coveted water-privileged communities. Completely renovated and impeccably maintained, this home offers approximately 4,000 finished square feet of beautifully designed living space where scale, comfort, and craftsmanship come together seamlessly. Walls of windows flood the open layout with natural light, highlighting rich hardwood floors, custom moldings, and timeless fixtures throughout. The gourmet kitchen is the true centerpiece of the home, featuring 42" cabinetry, stainless steel and chef-grade appliances, gleaming granite countertops, and an oversized center island

$795,000

4 beds3 baths4,000 sq ft

406 Harbor Dr, Annapolis, MD 21403

0.29 acre lot • Community pool • Built 1972

(410) 263-8686

ABOUT THIS HOME
Old Annapolis Neck, MD Homes for Sale
MAJOR UPDATES JUST COMPLETED + SIGNIFICANT PRICE IMPROVEMENT! This waterfront home has been freshly painted throughout and features a brand-new roof, offering peace of mind and a fresh, move-in-ready feel. Now priced at $849,900 (previously $899,000), this is a rare opportunity to secure waterfront living in Kitty Creek at a compelling new value. Located just a short drive from Quiet Waters Park, Downtown Annapolis, and everything the area has to offer, this home is nestled in the desirable Kitty Creek community. With approximately 80 feet of waterfront, the 3-bedroom, 2.5-bath residence features a bright and open main level with vaulted ceilings connecting the living room, dining area, kit

$849,900

3 beds2.5 baths1,801 sq ft

3109 Ervin Ct, Annapolis, MD 21403

0.46 acre lot • 2 parking spots • Built 1986

(888) 860-7369

COMING SOON

ABOUT THIS HOME
Old Annapolis Neck, MD Homes for Sale
Set in the sought-after Hillsmere neighborhood of Annapolis, this 2,200-square-foot rancher offers a calm, coastal feel enhanced by a single serene water view and a long list of significant updates. The home features a brand new kitchen with fully custom cabinets and a Wolf Range, newly renovated bathrooms, a roof replaced in 2021 with a 10-year warranty as reported by the seller, new windows added in 2022 according to seller-provided information, a new HVAC system also installed in 2022 per seller records, a new hot water heater from 2023 as stated by the seller, and a water softener from 2019 based on the seller’s account, along with numerous additional upgrades throughout the prope

$995,000

3 beds2 baths2,187 sq ft

150 E Bay View Dr, Annapolis, MD 21403

0.48 acre lot • 2 garage spots • Community pool

(410) 486-4504

Property at 6 Victor Pkwy, Annapolis, MD 21403, 3 beds, 1 bath

$364,900

3 beds1 bath912 sq ft

6 Victor Pkwy, Annapolis, MD 21403

(410) 729-7700

Property at 30-A Hearthstone Ct Unit A, Annapolis, MD 21403, 2 beds, 2 baths

$300,000

2 beds2 baths1,217 sq ft

30-A Hearthstone Ct Unit A, Annapolis, MD 21403

(410) 956-3500

Property at 10-L Sandstone Ct, Annapolis, MD 21403, 3 beds, 2 baths

$315,000

3 beds2 baths1,333 sq ft

10-L Sandstone Ct, Annapolis, MD 21403

(301) 445-1395

Property at 10-G Sandstone Ct, Annapolis, MD 21403, 2 beds, 2 baths

$315,000

2 beds2 baths1,103 sq ft

10-G Sandstone Ct, Annapolis, MD 21403

(443) 333-8535

Property at 920 Old Annapolis Neck Rd, Annapolis, MD 21403, 4 beds, 2.5 baths

$719,995

4 beds2.5 baths2,552 sq ft

920 Old Annapolis Neck Rd, Annapolis, MD 21403

(703) 652-5760

Property at 3123 Arundel On The Bay Road - Taft Model, Annapolis, MD 21403, 4 beds, 2.5 baths

$799,990

4 beds2.5 baths2,580 sq ft

3123 Arundel On The Bay Road - Taft Model, Annapolis, MD 21403

(410) 255-3690

Property at 3276 Kitty Duvall Dr, Annapolis, MD 21403, 2 beds, 2 baths

$549,000

2 beds2 baths1,434 sq ft

3276 Kitty Duvall Dr, Annapolis, MD 21403

(240) 219-2422

Property at 106 Stilly Way, Annapolis, MD 21403, 4 beds, 4.5 baths

$974,990

4 beds4.5 baths4,594 sq ft

106 Stilly Way, Annapolis, MD 21403

(410) 979-7740

Property at Lynnfield Plan, Annapolis, MD 21403, 4 beds, 3.5 baths

$1,034,990

4 beds3.5 baths4,213 sq ft

Lynnfield Plan, Annapolis, MD 21403

Listing provided by Zillow

Property at Fitzgerald Plan, Annapolis, MD 21403, 4 beds, 3.5 baths

$1,064,990

4 beds3.5 baths4,336 sq ft

Fitzgerald Plan, Annapolis, MD 21403

Listing provided by Zillow

Property at Admiral Plan, Annapolis, MD 21403, 4 beds, 4.5 baths

$1,079,990

4 beds4.5 baths4,483 sq ft

Admiral Plan, Annapolis, MD 21403

Listing provided by Zillow

Property at Kensington Plan, Annapolis, MD 21403, 4 beds, 4.5 baths

$1,059,990

4 beds4.5 baths4,245 sq ft

Kensington Plan, Annapolis, MD 21403

Listing provided by Zillow

Property at 1012 Carrs Rd, Annapolis, MD 21403

$98,000

— beds— baths— sq ft

1012 Carrs Rd, Annapolis, MD 21403

(410) 263-8686

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Nearby homes that match your criteria

ABOUT THIS HOME
Old Annapolis Neck, MD Homes for Sale
Discover the charm of Cedar Ridge, where this delightful end-of-row townhouse awaits you! Built in 1974, this traditional gem boasts 1,320 sq. ft. of inviting living space, featuring 3 spacious bedrooms and 2.5 bathrooms. The community offers a refreshing outdoor pool, perfect for summer relaxation and social gatherings. Nestled in a vibrant neighborhood, Cedar Ridge is known for its friendly atmosphere and convenient amenities. Enjoy easy access to local parks, shopping, and dining options that cater to every taste. The association takes care of snow removal and trash services, allowing you to focus on what truly matters. With ample parking and a low-maintenance lot, this home is perfect f

$395,000

3 beds2.5 baths1,320 sq ft

1041 Cedar Ridge Ct, Annapolis, MD 21403

$267 HOA • Community pool • Built 1974

(410) 255-3690

NEW CONSTRUCTION

ABOUT THIS HOME
Old Annapolis Neck, MD Homes for Sale
A brand-new home for the brand-new you. You’ve worked hard to get here—now you deserve a home that reflects it. With Whitehall Building & Company, your dream home becomes reality through a flexible design/build process, a guaranteed delivery date, and a fixed-price contract. This exceptional to-be-built waterfront residence in coveted Parkwood offers the perfect blend of Eastport living with the privacy and serenity you’ve been searching for. The thoughtfully designed floor plan features a gourmet kitchen with quartz countertops, 42" custom cabinetry, exposed beams, 10’ main-level ceilings, and wide-plank luxury vinyl flooring. A main-level primary suite p

$2,950,000

5 beds4.5 baths4,116 sq ft

703 Glendon Ave, Annapolis, MD 21403

Custom cabinetry • One-level living • Gourmet kitchen

(888) 860-7369

OPEN JAN 10, 11AM TO 3PM

ABOUT THIS HOME
Old Annapolis Neck, MD Homes for Sale
Welcome to the gated community of Chesapeake Harbour, offering a stress-free lifestyle! This second-floor condo features two balconies. The large wrap-around balcony provides stunning views of the marina, while the second balcony, located off the kitchen, offers views of the bay. Inside, the main level features an open-concept living area and a spacious kitchen with stainless steel appliances and abundant cabinet and counter space. The primary suite is also located on this level. Up the beautiful spiral staircase, you will find a loft/bedroom and an additional sitting area. Chesapeake Harbour provides residents with a swimming pool, tennis courts, a beach, and much more. You are also within

$712,000

2 beds2 baths1,688 sq ft

2106 Chesapeake Harbour Dr #202, Annapolis, MD 21403

$774 HOA • 2 parking spots • Community pool

(302) 846-7839

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ABOUT THIS HOME
Old Annapolis Neck, MD Homes for Sale
Absolutely transformed with a recently completed interior remodel this stunning contemporary home boasts panoramic water views across Lake Hillsmere and out to the South River; located in the coveted Hillsmere Shores community. With 5 bedrooms that all provide newly updated private baths, over 4,000 sqft of living space, 9'+ ceilings, freshly renovated first floor office, multiple decks including a unique, spacious 360 sqft roof garden accessed from the third floor bedroom suite and lounge area, this home is perfect for entertaining gatherings large or small. Enjoy the captivating views from almost every room! The brand new beautifully designed and appointed gourmet Kitchen features leathe

$1,400,000

5 beds5 baths4,308 sq ft

133 Lake View Dr, Annapolis, MD 21403

Wrap around porch • 360 sqft roof garden • Private balcony

(410) 280-5600

ABOUT THIS HOME
Old Annapolis Neck, MD Homes for Sale
Waterfront living at its finest. Welcome to this marina-front gem in the highly sought-after, 24-hour gated Chesapeake Harbour community. This beautifully renovated 1-bedroom, 1.5-bath terrace-level condo offers effortless coastal living paired with resort-style amenities and some of the most breathtaking views in Annapolis. Completely rehabbed from top to bottom by the original owners, this home features all-new flooring, fresh paint, updated electrical fixtures and lighting, and full renovations of the kitchen, bathrooms, and separate laundry room. The kitchen shines with brand-new stainless-steel appliances (with warranties in place) and allows the buyer to select cabinet hardware to add

$594,000

1 bed1.5 baths1,000 sq ft

7036 Harbour Village Ct Unit T1, Annapolis, MD 21403

Private patio • Waterfront living • Updated kitchen

(443) 660-9229

ABOUT THIS HOME
Old Annapolis Neck, MD Homes for Sale
Welcome to this lovely 2-bedroom, 1-bathroom home in the heart of Annapolis, offering classic charm and modern updates throughout. Featuring beautiful hardwood floors and a traditional layout, this home provides comfort and functionality in every room. The updated kitchen boasts a center island, granite and a spacious pantry all perfect for meal prep or casual dining. The bathroom has been tastefully renovated and includes a tub/shower combo. The newly-carpeted basement offers flexible space for a home office, gym or recreation area plus dual closets for extra storage. Utilize the savings and comfort from the high-efficiency zoned dual heating/cooling system and heat pump. Outside, enjoy th

$515,000

2 beds1 bath1,190 sq ft

1005 Hyde Park Dr, Annapolis, MD 21403

Renovated bathroom • Spacious pantry • Updated kitchen

(866) 987-3937

Property at 1071 Cedar Ridge Ct, Annapolis, MD 21403, 3 beds, 2.5 baths

$395,000

3 beds2.5 baths1,320 sq ft

1071 Cedar Ridge Ct, Annapolis, MD 21403

(410) 224-2200

Property at 111 Janwall St, Annapolis, MD 21403, 3 beds, 2.5 baths

$629,900

3 beds2.5 baths1,754 sq ft

111 Janwall St, Annapolis, MD 21403

(410) 398-1247

Property at 2108 Chesapeake Harbour Dr E #201, Annapolis, MD 21403, 3 beds, 3 baths

$625,000

3 beds3 baths1,700 sq ft

2108 Chesapeake Harbour Dr E #201, Annapolis, MD 21403

(410) 429-7425

Property at 2175 Chesapeake Harbour Dr, Annapolis, MD 21403, 4 beds, 4.5 baths

$2,595,000

4 beds4.5 baths2,513 sq ft

2175 Chesapeake Harbour Dr, Annapolis, MD 21403

(410) 280-5600

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