20

Craftsman Homes for Sale in Annapolis, MD

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  • 3307 Harness Creek Rd, Annapolis, MD 21403
    3307 Harness Creek Rd, Annapolis, MD 21403
    3307 Harness Creek Rd, Annapolis, MD 21403
    /46

    $2,895,000

    • 3 Beds
    • 2.5 Baths
    • 2,570 Sq Ft

    3307 Harness Creek Rd, Annapolis, MD 21403

    Welcome to 3307 Harness Creek Road: a Nantucket style, coastal home set on a private peninsula with spectacular water views, a serene 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

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    (410) 762-4260

    3307 Harness Creek Rd, Annapolis, MD 21403
  • 48 Murray Ave, Annapolis, MD 21401
    48 Murray Ave, Annapolis, MD 21401
    48 Murray Ave, Annapolis, MD 21401
    /39

    $1,695,000

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

    48 Murray Ave, Annapolis, MD 21401

    Modern Luxury Meets Murray Hill Charm | Experience the refined standard of Annapolis living in this masterfully reimagined Murray Hill residence. This home is a rare achievement in design—a down-to-the-studs transformation that honors its historic charm while introducing a graceful, curated, modern aesthetic. Cross the threshold onto original Heart Pine hardwood floors, glowing with a warmth that

    Agent Photo

    Andrew Riguzzi

    Compass

    (443) 294-8352

    48 Murray Ave, Annapolis, MD 21401
  • 1715 Porters Hill Rd, Annapolis, MD 21401
    1715 Porters Hill Rd, Annapolis, MD 21401
    1715 Porters Hill Rd, Annapolis, MD 21401
    /53

    $3,950,000

    • 4 Beds
    • 6 Baths
    • 6,594 Sq Ft

    1715 Porters Hill Rd, Annapolis, MD 21401

    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

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    (410) 438-8851

    1715 Porters Hill Rd, Annapolis, MD 21401
  • 116 Stilly Way, Annapolis, MD 21403
    116 Stilly Way, Annapolis, MD 21403
    116 Stilly Way, 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

    Terri Hill

    Builder Solutions Realty

    (443) 222-1215

    116 Stilly Way, Annapolis, MD 21403
  • 400 Jefferson St, Annapolis, MD 21403
    400 Jefferson St, Annapolis, MD 21403
    400 Jefferson St, Annapolis, MD 21403
    /47

    $1,990,000 Open Sun 1PM - 3PM

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

    400 Jefferson St, Annapolis, MD 21403

    Nestled in the heart of historic Eastport Annapolis, this coastal craftsman has been extensively remodeled, offering a perfect blend of classic charm and contemporary elegance. The home is set on a generously sized lot, providing abundant green space, with new sod and landscaping coming soon. Premium exterior finishes include an inviting front porch, James Hardi siding and Anderson 400 windows.

    Brian Jacobs Coldwell Banker Realty

    400 Jefferson St, Annapolis, MD 21403
  • 146 Duke of Gloucester St, Annapolis, MD 21401
    146 Duke of Gloucester St, Annapolis, MD 21401
    146 Duke of Gloucester St, Annapolis, MD 21401
    /58

    $1,999,999

    • 4 Beds
    • 3.5 Baths
    • 3,042 Sq Ft

    146 Duke of Gloucester St, Annapolis, MD 21401

    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 updated throughout, this

    Rob Carter Douglas Realty, LLC

    146 Duke of Gloucester St, Annapolis, MD 21401
  • 4 Shiley St, Annapolis, MD 21401
    4 Shiley St, Annapolis, MD 21401
    4 Shiley St, Annapolis, MD 21401
    /13

    $3,095,000 New Construction

    • 5 Beds
    • 5.5 Baths
    • 5,312 Sq Ft

    4 Shiley St, Annapolis, MD 21401

    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

    Brad Kappel TTR Sotheby's International Realty

    4 Shiley St, Annapolis, MD 21401
  • 327 Riverview Trail, Annapolis, MD 21401
    327 Riverview Trail, Annapolis, MD 21401
    327 Riverview Trail, Annapolis, MD 21401
    /46

    $2,349,000

    • 3 Beds
    • 3.5 Baths
    • 1,831 Sq Ft

    327 Riverview Trail, Annapolis, MD 21401

    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

    Brad Kappel TTR Sotheby's International Realty

    327 Riverview Trail, Annapolis, MD 21401
  • 820 Bay Ridge Ave, Annapolis, MD 21403
    820 Bay Ridge Ave, Annapolis, MD 21403
    /2

    $1,875,000 Coming Soon

    • 4 Beds
    • 4.5 Baths
    • 3,658 Sq Ft

    820 Bay Ridge Ave, Annapolis, MD 21403

    An elegant expression of space, style, and coastal living, 820 Bay Ridge Avenue offers four beautifully finished levels in the heart of Eastport’s coveted Sailor’s Quay enclave. This thoughtfully designed Modern Craftsman presents with quiet sophistication—from the white picket fence and manicured grounds to the gracious brick front porch—setting the tone for refined yet comfortable living.

    Wendy Oliver Coldwell Banker Realty

    820 Bay Ridge Ave, Annapolis, MD 21403
  • 1603 Winchester Rd, Annapolis, MD 21409
    1603 Winchester Rd, Annapolis, MD 21409
    1603 Winchester Rd, Annapolis, MD 21409
    /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
  • 4 Southgate Ave, Annapolis, MD 21401
    4 Southgate Ave, Annapolis, MD 21401
    4 Southgate Ave, Annapolis, MD 21401
    /120

    $3,500,000

    • 5 Beds
    • 4.5 Baths
    • 4,015 Sq Ft

    4 Southgate Ave, Annapolis, MD 21401

    An exceptional offering on Southgate Avenue in Murray Hill, this stately American Four Square was masterfully reimagined in 2021 by the current owner, in collaboration with Cumberstone Builders and acclaimed architect Jay Schwarz of Alt/Breeding/Schwarz. Four Southgate Avenue seamlessly blends historic charm and architectural pedigree with the ease of modern living. A classic front porch greets

    Malina Koerschner Coldwell Banker Realty

    4 Southgate Ave, Annapolis, MD 21401
  • 1217 Hampton Rd, Annapolis, MD 21409
    1217 Hampton Rd, Annapolis, MD 21409
    1217 Hampton Rd, Annapolis, MD 21409
    /25

    $896,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    1217 Hampton Rd, Annapolis, MD 21409

    New Construction in Cape St. Claire. Home construction has now started. Delivery date will be end of August or beginning of September. Days on the market began when lot was purchased. Please look at the documents section of the listing to see all standard features included with this home and all floor plans and site plan. Pictures shown in this listing are of the home now framed and a previous

    Frank Livingston Cook Real Estate Brokerage

    1217 Hampton Rd, Annapolis, MD 21409
  • 92 Clifford Blvd, Annapolis, MD 21401
    92 Clifford Blvd, Annapolis, MD 21401
    92 Clifford Blvd, Annapolis, MD 21401
    /64

    $820,000

    • 4 Beds
    • 2.5 Baths
    • 2,252 Sq Ft

    92 Clifford Blvd, Annapolis, MD 21401

    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 Brazilian cherry hardwood flooring,

    Chad Robertson Compass

    92 Clifford Blvd, Annapolis, MD 21401
  • 819 Janice Dr, Annapolis, MD 21403
    819 Janice Dr, Annapolis, MD 21403
    819 Janice Dr, Annapolis, MD 21403
    /42

    $1,125,000

    • 4 Beds
    • 3.5 Baths
    • 4,043 Sq Ft

    819 Janice Dr, Annapolis, MD 21403

    Striking modern craftsman located in Eastport! This beautifully constructed home boasts 3 levels of living space including the finished basement with great room, bonus room and full bath. The inviting front porch with balcony above welcomes you as you step onto the property. The high ceilings, plethora of windows for natural light and wide open floor plan set the tone for this wonderful home. The

    Brad Kappel TTR Sotheby's International Realty

    819 Janice Dr, Annapolis, MD 21403
  • 107 Monticello Ave, Annapolis, MD 21401
    107 Monticello Ave, Annapolis, MD 21401
    /2

    $1,500,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 3,159 Sq Ft

    107 Monticello Ave, Annapolis, MD 21401

    Coming Soon!

    Alexandra Ryan EXP Realty, LLC

    107 Monticello Ave, Annapolis, MD 21401
  • 608 S Cherry Grove Ave, Annapolis, MD 21401
    608 S Cherry Grove Ave, Annapolis, MD 21401
    608 S Cherry Grove Ave, Annapolis, MD 21401
    /37

    $550,000

    • 3 Beds
    • 4 Baths
    • 2,024 Sq Ft

    608 S Cherry Grove Ave, Annapolis, MD 21401

    You will love this large, move-in ready townhome. Super clean! Side windows on this end-of-group beauty give this unit an even better bright and open feel. Three finished levels with beautiful wide hardwoods. Gourmet eat-in kitchen with granite countertops, two tiered island with sink, newer dishwasher, refrigerator and microwave. Primary bedroom suite with large walk-in closet with storage

    Michael Schroeder Long & Foster Real Estate, Inc.

    608 S Cherry Grove Ave, Annapolis, MD 21401
  • 5 Franklin St, Annapolis, MD 21401
    5 Franklin St, Annapolis, MD 21401
    5 Franklin St, Annapolis, MD 21401
    /46

    $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
  • 105 Griscom Square Way, Annapolis, MD 21403
    105 Griscom Square Way, Annapolis, MD 21403
    105 Griscom Square Way, Annapolis, MD 21403
    /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
  • 304 Glen Ave, Annapolis, MD 21401
    304 Glen Ave, Annapolis, MD 21401
    304 Glen Ave, Annapolis, MD 21401
    /49

    $1,295,000 Open Fri 4PM - 6PM

    • 4 Beds
    • 3.5 Baths
    • 3,219 Sq Ft

    304 Glen Ave, Annapolis, MD 21401

    Just in time for Commissioning Week — walk to Navy-Marine Corps Memorial Stadium from this beautifully renovated Annapolis home that perfectly blends historic charm with modern convenience. Ideally located near downtown Annapolis and the stadium, this property offers incredible flexibility, abundant off-street parking, and a rare apartment/in-law suite above the 2-car garage. Completely renovated

    Michelle Fegan RE/MAX Executive

    304 Glen Ave, Annapolis, MD 21401
  • 141 Stilly Way, Annapolis, MD 21403
    141 Stilly Way, Annapolis, MD 21403
    141 Stilly Way, Annapolis, MD 21403
    /55

    $1,049,000

    • 5 Beds
    • 4.5 Baths
    • 5,140 Sq Ft

    141 Stilly Way, Annapolis, MD 21403

    She’s one and a half years young. She’s flawless. And she’s exactly the kind of home buyers spend months hoping will hit the market—but almost never does. Welcome to 141 Stilly Way, a fully upgraded, privately owned resale in Parkside Preserve where every premium finish, every design decision, and every upgrade has already been completed for you. This is not a builder sale. There are no

    Wendy Oliver Coldwell Banker Realty

    141 Stilly Way, Annapolis, MD 21403
Maryland Anne Arundel County Annapolis

Real Estate & Homes for Sale in Annapolis, MD

Home Trends in Annapolis, MD

On average, homes in Annapolis, MD sell after 38 days on the market compared to the national average of 57 days. The median sale price for homes in Annapolis, MD over the last 12 months is $620,000, up 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$620,000
Median Single Family Sale Price
$827,500
Median Townhouse Sale Price
$447,500
Median 2 Bedroom Sale Price
$430,000
Median 1 Bedroom Sale Price
$453,700
Average Price Per Sq Ft
$360
Number of Homes for Sale
270
Last 12 months Home Sales
1,311
Months of Supply
2.50
Median List Price
$649,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%

Popular Home Searches in Annapolis, MD

In Annapolis, waterfront living and historic charm are top priorities, especially near Eastport and the historic district.

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