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Craftsman Homes for Sale in Annapolis, MD

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  • /6

    $1,398,000 Coming Soon

    • 4 Beds
    • 4 Baths
    • 3,070 Sq Ft

    357 Overlook Trail, Annapolis, MD 21401

    Enchanting Craftsman-Style Waterfront Retreat in Epping ForestTucked away in the prestigious gated community of Epping Forest, this beautifully renovated Craftsman-style home offers a rare opportunity to enjoy serene waterfront living with a private deep-water pier on Clements Creek, just off the Severn River. Complete with a 12,000 lb boat lift and a private sandy beach, it’s a dream for

    Agent Photo

    Darrel Reel

    Corner House Realty

    (410) 415-1480

    357 Overlook Trail, Annapolis, MD 21401
  • /17

    $849,500 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,671 Sq Ft

    3447 Rockway Ave, Annapolis, MD 21403

    THIS HOME IS CURRENTLY UNDER CONSTRUCTION WITH THE EXPECTED COMPLETED DATE OF 9/30/25. There is still time to make interior design choices if you hurry!! Just one block from the water, this brand-new construction offers a stylish and versatile design. The open floor plan is perfect for modern living, seamlessly blending the kitchen, living, and dining areas. The updated kitchen features sleek

    Agent Photo

    Jamie Richardson

    Coldwell Banker Realty

    (410) 941-3673

    3447 Rockway Ave, Annapolis, MD 21403
  • /11

    $849,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,580 Sq Ft

    1094 Linden Tree Drive - Taft Model, Annapolis, MD 21409

    Ameri-Star Homes is pleased to offer this incredible opportunity for a to-be-built, craftsman-style home situated on a beautiful 9,000 square foot lot in the sought-after waterfront community of Cape St. Clare in Annapolis. (There are two lots at this location). *Builder is paying $5,000 TOWARDS CLOSING COSTS with use of builders approved lender and title company. This exciting Taft model is

    Julie Lamartina-Dinko Douglas Realty, LLC

    1094 Linden Tree Drive - Taft Model, Annapolis, MD 21409
  • /73

    $1,399,000

    • 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
  • /52

    $1,375,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 5,124 Sq Ft

    9 Rusty Red Dr, Annapolis, MD 21401

    Move-in ready new construction from acclaimed local builder, Sturbridge Homes. This spectacular home offers over 5,000 square feet of finished space in the heart of Annapolis's Homewood neighborhood, close to all of the entertainment and enjoyment available in our historic town. Located near the new Annapolis Public Library, Maryland Hall, Annapolis Town Center, and the Naval Academy Stadium,

    Alison Wisnom Coldwell Banker Realty

    9 Rusty Red Dr, Annapolis, MD 21401
  • /2

    $1,700,000 New Construction

    • 4 Beds
    • 3 Baths
    • 3,640 Sq Ft

    400 Jefferson St, Annapolis, MD 21403

    Custom coastal craftsman home is currently under construction in Eastport - Annapolis, Maryland. This home will feature a perfect blend of classic Eastport and luxury coastal craftsman design. Permitting is complete. This expansive 3600 +/- (approx. 850 unfinished) sq. foot home will offer 4 bedrooms and 3 baths with an open floor plan concept. Truly an entertainer’s dream with hardwood floors,

    Brian Jacobs Coldwell Banker Realty

    400 Jefferson St, Annapolis, MD 21403
  • /44

    $3,195,000

    • 3 Beds
    • 2.5 Baths
    • 2,236 Sq Ft

    3307 Harness Creek Rd, Annapolis, MD 21403

    Welcome to 3307 Harness Creek Road-- a Nantucket style, coastal home with spectacular water views, a private backyard oasis and two deep-water piers on protected Harness Creek. This waterside gem, with 190 ft of waterfrontage, is situated directly across from Quiet Waters Park and offers quick access to the South River and the Chesapeake Bay.Inside, you’re greeted by the natural warmth

    Reid Buckley Long & Foster Real Estate, Inc.

    3307 Harness Creek Rd, Annapolis, MD 21403
  • /94

    $875,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 4 Baths
    • 2,634 Sq Ft

    735 Glenwood St, Annapolis, MD 21401

    Welcome to 735 Glenwood Street—where location, lifestyle, and livability come together in one of Annapolis’ most walkable neighborhoods. From here, you can stroll to the U.S. Naval Academy, grab dinner on West Street, catch a game at Navy Stadium, or head downtown for waterfront views and local events. This is the kind of address that puts you in the center of everything, without sacrificing

    Lily Vallario EXP Realty, LLC

    735 Glenwood St, Annapolis, MD 21401
  • /49

    $695,000

    • 4 Beds
    • 5 Baths
    • 1,880 Sq Ft

    103 Norma Alley, Annapolis, MD 21403

    Welcome to this stunning, light-filled, and modern four-bedroom townhome located in the private, sought-after community of Primrose Hill in historic Annapolis. This beautifully appointed four-level home offers a spacious and versatile layout, including a top-floor loft with sun-drenched skylights and a full bath—perfect as a guest suite, office, or media room. Featuring 4 bedrooms, 3 full baths,

    Joanna Dalton Coldwell Banker Realty

    103 Norma Alley, Annapolis, MD 21403
  • /95

    $1,700,000

    • 3 Beds
    • 3.5 Baths
    • 2,719 Sq Ft

    2186 Chesapeake Harbour Dr E, Annapolis, MD 21403

    Unprecedented waterfront opportunity in The Community of Chesapeake Harbour! Unduplicatable Gated Chesapeake Harbour offers lavish Chesapeake Bayfront Annapolitan style living. This community could never be built today and this property completes the trifecta with perfect location and luxurious refinements. 4 Levels of spectacular waterfront perfection masterfully done. Fully renovated and

    Christy Bishop Berkshire Hathaway HomeServices PenFed Realty

    2186 Chesapeake Harbour Dr E, Annapolis, MD 21403
  • /50

    $8,995,000

    • 7 Beds
    • 9 Baths
    • 12,200 Sq Ft

    1900 Carrollton Rd, Annapolis, MD 21409

    Rare opportunity for a true legacy property on the Severn River! Built by Pilli Custom Homes, this home is a masterpiece of craftsmanship. Wake up every morning to the everchanging scenery out your windows, step out onto your private balcony with a freshly brewed coffee from your in-room coffee bar, feeling the gentle river breeze as you watch sailboats drift by. Make your way down via the

    Brad Kappel TTR Sotheby's International Realty

    1900 Carrollton Rd, Annapolis, MD 21409
  • /68

    $3,475,000

    • 6 Beds
    • 5.5 Baths
    • 6,732 Sq Ft

    1576 Bay Head Rd, Annapolis, MD 21409

    Boating season is here! Incredible opportunity - Seller will hold a 10% second mortgage at 5.87% for five years if you are putting a minimum of 20% down! Welcome to 1576 Bay Head Road, an exceptional waterfront estate where luxury living meets the ultimate Chesapeake Bay lifestyle. Perfectly situated on a private one-acre lot along the calm, protected waters of the Little Magothy River, this

    Wendy Oliver Coldwell Banker Realty

    1576 Bay Head Rd, Annapolis, MD 21409
  • /56

    $1,150,000

    • 4 Beds
    • 3.5 Baths
    • 2,372 Sq Ft

    319 Epping Way, Annapolis, MD 21401

    Sellers are offering $25,000 to go towards siding replacement. This beautiful property offers three levels of spacious, comfortable living in the neighborhood of Epping Forest. Walking through the front door, vaulted ceilings and natural light greet you in the dining/living room area off the kitchen. A main level bedroom suite offers convenience and a second suite upstairs boasts extra privacy.

    Brittany Chaffee Hogan Companies Residential

    319 Epping Way, Annapolis, MD 21401
  • /62

    $1,150,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 4,000 Sq Ft

    827 Janice Dr, Annapolis, MD 21403

    Live the Eastport Dream – Luxury, Water Access & Walkability at 827 Janice Drive. Step into a rare opportunity to own a custom-built showpiece in Eastport’s best-kept secret—Green Acres. Welcome to 827 Janice Drive, where elevated design meets the unbeatable Annapolis lifestyle. This 4,000+ square foot home, meticulously constructed by Cedar Square Homes, is more than just beautiful—it's move-in

    Wendy Oliver Coldwell Banker Realty

    827 Janice Dr, Annapolis, MD 21403
  • /4

    $644,900 New Construction

    • 4 Beds
    • 4.5 Baths

    2073 Old Admiral Ct, Annapolis, MD 21401

    May Delivery. Welcome to the Homes at River Birch. A luxury townhome community that celebrates the best of modern design and urban lifestyles. These farmhouse, attached homes are semi-custom with 4 bedroom options within two different floor plans. These homes boasts an abundance of features including wide plank LVP floors, gorgeous quartz countertops, stainless steel appliances, an attached

    Alexander VonBussenius VB Realty, LLC

    2073 Old Admiral Ct, Annapolis, MD 21401
  • /39

    $1,039,990 Open Sat 12PM - 3PM

    • 5 Beds
    • 5.5 Baths
    • 5,017 Sq Ft

    110 Stilly Way, Annapolis, MD 21403

    New Construction - Move In Ready March 2025! Please go to Model home to tour!Welcome to the Lynnfield model at Parkside Preserve, where luxury meets tranquility in this stunning new construction adjacent to the serene Quiet Waters Park. With over 5,017 finished square footage this meticulously designed living space across four levels, featuring 5-bedrooms, 5.5-bathrooms, 4th level loft,

    Mary Anne Long Keller Williams Realty Centre

    110 Stilly Way, Annapolis, MD 21403
  • /2

    $699,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    1192 Bay Highlands Dr, Annapolis, MD 21403

    Welcome to this generously spacious 4-bedroom, 2.5-bathroom home that blends comfort, charm, and functionality in every room. With its expansive layout and thoughtfully updated features, this home offers the perfect setting for both relaxing and entertaining.You’ll love the bright recessed lighting, plantation shutters, ceiling fans, and stunning crown molding throughout. The updated bamboo

    Shelley Baden Berkshire Hathaway HomeServices PenFed Realty

    1192 Bay Highlands Dr, Annapolis, MD 21403

Home Trends in Annapolis, MD

Housing Trends

Median Sale Price
$550,000
Median Single Family Sale Price
$1,033,403
Median Townhouse Sale Price
$574,500
Median 2 Bedroom Sale Price
$467,500
Median 1 Bedroom Sale Price
$489,900
Average Price Per Sq Ft
$381
Number of Homes for Sale
39
Last 12 months Home Sales
326
Months of Supply
1.40
Median List Price
$600,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
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