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Craftsman Homes for Sale in Annapolis, MD

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  • /52

    $2,795,000

    • 3 Beds
    • 2.5 Baths
    • 2,286 Sq Ft

    113 Bay Dr, Annapolis, MD 21403

    Live authentically. The Chesapeake Bay is the view, the backdrop and the reason to linger. From the covered bluestone porch, the horizon opens across the Bay with uninterrupted sky and water. Morning coffee, an afternoon breeze through open doors, evenings around the fire—the water sets the pace.Extensively renovated inside and out since 2019, this charming craftsman styled gem in the

    Agent Photo

    Elizabeth Atwood

    Krauss Real Property Brokerage

    113 Bay Dr, Annapolis, MD 21403
  • /21

    $1,099,990

    New Construction
    • 4 Beds
    • 3 Baths
    • 4,400 Sq Ft

    116 Stilly Way, Annapolis, MD 21403

    Backs to Quiet Waters Park! This spacious and elegant home offers 4 bedrooms, 3.5 bathrooms and approximately 4,400 sq. ft. of living space, with the option to expand to 5,300 sq. ft. by adding a fourth level. The gourmet kitchen features double wall ovens (with the upper oven including an air-fry option), a 36-inch gas cooktop and the choice of a cabinetry hood or stainless-steel chimney hood.

    Agent Photo

    Mrs. Terri E Hill

    Builder Solutions Realty

    116 Stilly Way, Annapolis, MD 21403
  • /50

    $950,000

    New Construction Open Sat 1PM - 3PM
    • 5 Beds
    • 3.5 Baths
    • 3,081 Sq Ft

    2175 Glencrest Cir, Annapolis, MD 21401

    Newly and beautifully built in 2026, this stone-accented detached Calvert Model by Dorsey Family Homes offers 3,081 finished square feet and is ideally positioned on a quiet cul-de-sac in desirable Rolling Knolls. Offering a sleek, contemporary design and a bright, airy atmosphere, the home provides a sophisticated foundation for any aesthetic. Abundant natural light complements 9-foot ceilings,

    Agent Photo

    Bob Lucido

    Keller Williams Lucido Agency

    2175 Glencrest Cir, Annapolis, MD 21401
  • /53

    $1,105,000

    $20K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,080 Sq Ft

    979 Bramleigh Ln, Annapolis, MD 21401

    Welcome to this exceptional single-family home nestled in one of Annapolis' most desirable neighborhoods. Offering morethan 4,000 square feet of thoughtfully designed living space, this beautiful residence features 4 spacious bedrooms, 3.5 bathrooms, and an ideal layout for both everyday living and entertaining.Step inside to an inviting open floor plan highlighted by a dramatic

    Robert Breeden Berkshire Hathaway HomeServices Homesale Realty

    979 Bramleigh Ln, Annapolis, MD 21401
  • /42

    $1,750,000

    • 4 Beds
    • 4 Baths
    • 1,848 Sq Ft

    219 Lockwood Ct, Annapolis, MD 21403

    Nestled in the heart of Eastport, this stunning Craftsman-style home offers the perfect blend of timeless charm and modern luxury. This was a complete remodel in 2012! Boasting 4 bedrooms and 4 full baths, this thoughtfully designed residence features an open floor plan accented by beautiful bamboo flooring adding warmth and style throughout. The gourmet kitchen is the centerpiece of the home,

    John Collins Long & Foster Real Estate, Inc.

    219 Lockwood Ct, Annapolis, MD 21403
  • /5

    $879,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,411 Sq Ft

    1049 Sun Valley Dr, Annapolis, MD 21409

    Ameri-Star Homes is proud to offer this exceptional opportunity to build a brand-new Craftsman-style home on a beautiful 9,225-square-foot corner homesite in the sought-after waterfront community of Cape St. Claire in Annapolis. Builder is offering $5,000 toward closing costs with the use of the builder’s approved lender and title company! The exciting Bancroft model offers approximately 2,411

    Julie Lamartina-Dinko Douglas Realty, LLC

    1049 Sun Valley Dr, Annapolis, MD 21409
  • /27

    $3,595,000

    New Construction
    • 6 Beds
    • 5.5 Baths
    • 5,718 Sq Ft

    1668 Homewood Landing Rd, Annapolis, MD 21409

    An extraordinary opportunity to create the luxury waterfront estate you've always envisioned. Perfectly positioned on a spectacular homesite offering approximately 120 feet of pristine shoreline and 8 feet of mean low water, this exceptional to-be-built custom residence by Whitehall Building & Co. combines timeless architecture, uncompromising craftsmanship, and an unparalleled waterfront

    Colleen Smith EXP Realty, LLC

    1668 Homewood Landing Rd, Annapolis, MD 21409
  • /24

    $896,000

    New Construction Open Sat 12PM - 2PM
    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    1217 Hampton Rd, Annapolis, MD 21409

    Home is drywalled and finally ready for showings. There will be an OPEN HOUSE on Sunday, August 30th from 12-2 PM. Another fantastic new home by Vineyard Builders who has an amazing reputation in the Cape is in the final stages of completion. New Construction in Cape St. Claire. Delivery date will be in late September. Days on the market began when lot was purchased. Please look at the documents

    Frank Livingston Cook Real Estate Brokerage

    1217 Hampton Rd, Annapolis, MD 21409
  • /66

    $739,000

    $96K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,252 Sq Ft

    92 Clifford Blvd, Annapolis, MD 21401

    Amazing home at an amazing price point! Welcome home to this beautifully maintained transitional Craftsman in sought-after Clifford Estates, NO HOA! From the moment you arrive, you’re greeted by a spacious Trex front porch, the perfect place to sip your morning coffee, unwind after a long day, and wave to neighbors passing by. Step inside to discover an inviting, light filled interior featuring

    Chad Robertson Compass

    92 Clifford Blvd, Annapolis, MD 21401
  • /58

    $1,950,000

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,042 Sq Ft

    146 Duke of Gloucester St, Annapolis, MD 21401

    Price improvement!!! Welcome to 146 Duke of Gloucester Street! As you approach the home, a welcoming front porch will greet you, offering a place to sit and take in all that Annapolis has to offer. Nestled in the heart of historic Annapolis, this beautifully appointed 4-bedroom, 3.5-bath residence seamlessly blends timeless charm with modern sophistication. Rich in character and thoughtfully

    Rob Carter Douglas Realty, LLC

    146 Duke of Gloucester St, Annapolis, MD 21401
  • /42

    $699,990

    $45K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,300 Sq Ft

    104 Groh Ln, Annapolis, MD 21403

    Some neighborhoods give you an address. Hillsmere gives you a way of life. At 104 Groh Lane, you’ll find a beautifully updated four-bedroom, three-bath home with approximately 2,300 square feet of finished living space, an exceptionally versatile floor plan, and a wonderful level, fenced backyard—all within one of Annapolis’ most beloved waterfront communities. Three bedrooms and two full baths

    Wendy Oliver Coldwell Banker Realty

    104 Groh Ln, Annapolis, MD 21403
  • /48

    $1,875,000

    • 4 Beds
    • 4.5 Baths
    • 3,900 Sq Ft

    820 Bay Ridge Ave, Annapolis, MD 21403

    There is something unmistakably special about life in Eastport—and 820 Bay Ridge Ave captures it beautifully. Set within coveted Sailor’s Quay, this exceptional residence offers more than 4,000 square feet of sophisticated living across four beautifully finished levels, combining timeless architecture, thoughtful customization, and an effortless coastal sensibility just moments from the heart of

    Wendy Oliver Coldwell Banker Realty

    820 Bay Ridge Ave, Annapolis, MD 21403
  • /39

    $2,500,000

    New Construction
    • 6 Beds
    • 6.5 Baths
    • 6,709 Sq Ft

    1603 Winchester Rd, Annapolis, MD 21409

    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

    Scott Schuetter Berkshire Hathaway HomeServices PenFed Realty

    1603 Winchester Rd, Annapolis, MD 21409
  • /95

    $2,650,000

    Open Sat 11AM - 4PM Coming Soon Sep 28
    • 5 Beds
    • 5 Baths
    • 4,435 Sq Ft

    8 Brooke Ave, Annapolis, MD 21401

    A rare opportunity in the heart of Murray Hill! Welcome to 8 Brooke Avenue, a stunning 2015 Traynor Brothers-built Craftsman offering nearly 5,000 square feet of beautifully finished living space just steps from Downtown Annapolis. Combining timeless architecture, exceptional craftsmanship, and the space and amenities today's luxury buyer desires, this extraordinary home features 5 bedrooms, 5

    Elizabeth DuLaney EXP Realty, LLC

    8 Brooke Ave, Annapolis, MD 21401
  • /10

    $869,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 3,381 Sq Ft

    1202 Southview Dr, Annapolis, MD 21409

    Ameri-Star Homes is proud to offer this exceptional opportunity to build a brand-new Craftsman-style home on a beautiful 9,000-square-foot homesite in the sought-after waterfront community of Cape St. Claire in Annapolis. Builder is offering $5,000 toward closing costs with the use of the builder's approved lender and title company! The exciting Taft model offers approximately 2,581 square feet

    Julie Lamartina-Dinko Douglas Realty, LLC

    1202 Southview Dr, Annapolis, MD 21409
  • /61

    $1,350,000

    • 4 Beds
    • 4 Baths
    • 5,091 Sq Ft

    203 S Southwood Ave, Annapolis, MD 21401

    Beautifully updated 4-bedroom, 2 full and 2 half bath home offering the perfect blend of comfort, style, and convenience in the heart of Annapolis. Designed for both everyday living and entertaining, this home features an updated kitchen with modern finishes and newer appliances, including an induction cooktop and oven, refrigerator, dishwasher. Upstairs, the expansive primary suite serves as a

    Tim Velasco ERA Martin Associates

    203 S Southwood Ave, Annapolis, MD 21401
  • /47

    $12,500,000

    • 5 Beds
    • 6.5 Baths
    • 5,993 Sq Ft

    5 Franklin St, Annapolis, MD 21401

    A rare opportunity on Spa Creek, this fully reimagined Murray Hill residence offers an extraordinary waterfront lifestyle just moments from downtown Annapolis. Completed in late 2023 after a full ground-up rebuild, the home spans 5,900+ sq. ft. of impeccably crafted living space, where natural materials, refined architectural details, and top-tier systems create a seamless blend of comfort and

    Brad Kappel TTR Sotheby's International Realty

    5 Franklin St, Annapolis, MD 21401
  • /8

    $995,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,850 Sq Ft

    105 Griscom Square Way, Annapolis, MD 21403

    Welcome to Eastport Estates at Griscom Square, a brand-new construction community of just 11 luxury single-family homes, located within one mile of downtown Eastport! Each residence showcases high-end finishes, spacious open-concept layouts, 9-foot ceilings, 4-5 Bedrooms, gourmet kitchen, modern baths, 2-car garages with private parking, and quality craftsmanship throughout, creating a truly

    Joanna Dalton Coldwell Banker Realty

    105 Griscom Square Way, Annapolis, MD 21403
  • /47

    $1,285,000

    • 4 Beds
    • 3 Baths
    • 3,398 Sq Ft

    1227 Cross Rd, Annapolis, MD 21403

    Discover elegance at 1227 Cross Road in Annapolis, Maryland, a stunning 2023-built home in the water-privileged Oyster Harbor community, elevated by upgrades made by the current owner since purchase. Enter through grand double doors into an open foyer with hickory hardwood floors, soaring ceilings, and crown molding. The great room impresses with a coffered ceiling, ceiling fan, fireplace, and

    Patrick DeLeonibus TTR Sotheby's International Realty

    1227 Cross Rd, Annapolis, MD 21403
  • /40

    $1,900,000

    Open Sat 1PM - 3PM $50K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 4,099 Sq Ft

    400 Jefferson St, Annapolis, MD 21403

    ***Owner financing available at 6%***Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this

    Brad Kappel TTR Sotheby's International Realty

    400 Jefferson St, Annapolis, MD 21403
  • /67

    $1,349,000

    • 5 Beds
    • 4.5 Baths
    • 3,600 Sq Ft

    111 Ellershaw Ct, Annapolis, MD 21401

    Rare Opportunity to own a newer home tucked away on a private cul-de-sac just a short stroll from everything Downtown Annapolis has to offer. Completed in 2022, this exceptional home showcases top of the line finishes throughout. Designer kitchen with Quartz countertops, custom cabinetry and high end GE Cafe appliances. Wide Plank hardwood floors throughout the main and upper levels. 9 foot

    Ryan Turner Coldwell Banker Realty

    111 Ellershaw Ct, Annapolis, MD 21401
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