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Homes for Sale in 21409

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  • /13

    $1,100,000

    • 5 Beds
    • 3 Baths
    • 5,465 Sq Ft

    15 E Nap Ln, Annapolis, MD 21409

    Price Reduction: Motivated Seller BRING ALL OFFERS! Get ready to fall in love with this Annapolis gem Nestled in the sought-after Captain Cove neighborhood on a 1.21-acre wooded lot, this beautifully maintained home is minutes from downtown Annapolis. Unique features include a rooftop deck, expansive back decking, and a bonus treehouse that doubles as a fun space for children or a peaceful

    Agent Photo

    Litra Simms

    Simms and Associates

    (443) 339-8629

    15 E Nap Ln, Annapolis, MD 21409
  • /75

    $3,200,000

    • 5 Beds
    • 2 Baths
    • 5,522 Sq Ft

    1979 Baltimore Annapolis Blvd, Annapolis, MD 21409

    Welcome to 1979 Baltimore Annapolis Blvd — where original charm meets opportunity. Set along one of the Severn River’s most desirable stretches with unobstructed views of the U.S. Naval Academy, this distinctive residence offers 5,522 finished square feet across three levels—seamlessly blending timeless character with a 2015 expansion and thoughtful modern updates. Enjoy a front-row seat to the

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    Angelica Dennis

    Keller Williams Capital Properties

    (443) 781-6808

    1979 Baltimore Annapolis Blvd, Annapolis, MD 21409
  • /2

    $600,000

    • 2 Beds
    • 2 Baths
    • 1,900 Sq Ft

    724 Darlow Dr, Annapolis, MD 21409

    Welcome to 224 Darlow Drive! This is a wonderful home in the 55+ Adult Living Community of Highland Woods. It consists of 2 bedrooms, 2 full baths on one level and has an open concept floor plan. It has 9' ceilings, and an adjacent family room to the kitchen that has wood flooring, a ceiling fan and a corner natural gas fireplace for the cooler evenings. Also included are lots of windows bringing

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    Doannie Tambascio

    Coldwell Banker Realty

    (443) 222-1462

    724 Darlow Dr, Annapolis, MD 21409
  • /38

    $395,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 1,496 Sq Ft

    332 Charred Oak Ct, Annapolis, MD 21409

    Welcome to this bright and spacious end-unit townhome in Whispering Woods. Fresh paint and brand-new carpet set the stage for a welcoming feeling as soon as you walk in. The new roof (to be installed by December 5th) will bring peace of mind for years to come. On the main level, the home opens up beautifully. The large kitchen offers plenty of room to cook, gather, and enjoy casual meals at the

    Agent Photo

    Gina White

    Coldwell Banker Realty

    (410) 343-4542

    332 Charred Oak Ct, Annapolis, MD 21409
  • /20

    $678,900 New Construction

    • 3 Beds
    • 2 - 3.5 Baths
    • 1,729+ Sq Ft

    Element 3 Bed Plan at Element at Mill Creek, Annapolis, MD 21409

    The Christopher Companies Builder
    78 Old Mill Bottom Rd N Unit 36791892, Annapolis, MD 21409
  • /15

    $459,900 New Construction

    • 1 Bed
    • 2 Baths
    • 1,076 Sq Ft

    Element 1 Bed Plan at Element at Mill Creek, Annapolis, MD 21409

    The Christopher Companies Builder
    78 Old Mill Bottom Rd N Unit 36791896, Annapolis, MD 21409
  • /18

    $472,070 New Construction

    • 2 Beds
    • 2 Baths
    • 1,210 Sq Ft

    Element 2 Bed Plan at Element at Mill Creek, Annapolis, MD 21409

    The Christopher Companies Builder
    78 Old Mill Bottom Rd N Unit 36791900, Annapolis, MD 21409
  • /47

    $535,000

    • 3 Beds
    • 2 Baths
    • 2,218 Sq Ft

    1165 Green Holly Ct, Annapolis, MD 21409

    Cape St. Claire Home sold with Extra Lot and Detached Garage Plans! Plans in Documents. This lovely Cape St. Claire property boasts an extra lot, offering more space for your family to enjoy. The Seller is providing approved plans and permit for a detached garage, adding even more potential for extra living space or possible ADU. Upon entering the home, you’ll immediately feel at ease. The

    Darlene Winegardner RE/MAX Executive

    1165 Green Holly Ct, Annapolis, MD 21409
  • /69

    $925,000

    • 5 Beds
    • 2 Baths
    • 2,969 Sq Ft

    1913 Dulaney Place, Annapolis, MD 21409

    The perfect blend of 1950s charm and modern Annapolis living, situated steps from the water and an easy walk or bike ride across the Naval Academy Bridge to West Annapolis and the historic downtown area. This classic Pendennis Mount ranch-style home, built in 1959, has been beautifully updated. Step inside to find the home's original character with hardwood floors, now opened up into a generous

    Jamie Angichiodo RE/MAX Leading Edge

    1913 Dulaney Place, Annapolis, MD 21409
  • /19

    $1,350,000

    • 3 Beds
    • 2.5 Baths
    • 1,994 Sq Ft

    2203 Mulberry Hill Rd, Annapolis, MD 21409

    Bring your personal touch to this waterfront get away and enjoy the waterfront lifestyle! Waterfront Suisse Chalet on Mill Creek – Annapolis, MD Experience the perfect blend of charm, comfort, and waterfront living in this spacious 3-bedroom, 2.5-bath Suisse Chalet nestled on scenic Mill Creek, just off the Chesapeake Bay and Severn River. Located on Mulberry Hill Road in Annapolis, this

    Tommy Eicher Coldwell Banker Realty

    2203 Mulberry Hill Rd, Annapolis, MD 21409
  • /71

    $1,247,900

    • 5 Beds
    • 4 Baths
    • 3,660 Sq Ft

    1635 N Winchester Rd, Annapolis, MD 21409

    A Rare Exceptional Retreat in Winchester Estates — Annapolis, MDWelcome to an extraordinary custom-built residence where timeless elegance meets unparalleled serenity. Set on a magnificently landscaped, park-like acre, this 5-bedroom, 4-bath estate offers a level of privacy and tranquility seldom found so close to the heart of downtown Annapolis. Nestled within the prestigious Winchester

    Ana Lopez Equity Property Investments

    1635 N Winchester Rd, Annapolis, MD 21409
  • /82

    $1,300,000

    • 5 Beds
    • 2 Baths
    • 1,919 Sq Ft

    1814 Pleasant Plains Rd, Annapolis, MD 21409

    RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15’ right of way from Burley Lane to a 35' wide fee simple area along Burley Creek and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods, abundant windows

    Karlton Morris Long & Foster Real Estate, Inc.

    1814 Pleasant Plains Rd, Annapolis, MD 21409
  • /82

    $1,300,000

    • 5 Beds
    • 2 Baths
    • 1,919 Sq Ft

    1814 & 1836 Pleasant Plains & Cherry Rd, Annapolis, MD 21409

    RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15’ right of way from Burley Lane to a 35' wide fee simple area along Burley Creek water frontage and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods,

    Karlton Morris Long & Foster Real Estate, Inc.

    1814 & 1836 Pleasant Plains & Cherry Rd, Annapolis, MD 21409
  • /65

    $815,000

    • 4 Beds
    • 3 Baths
    • 3,908 Sq Ft

    1160 Skyview Dr, Annapolis, MD 21409

    Spacious colonial in the much sought after Annapolis Town of Cape St Claire. The Chesapeake Bay and tributaries surround this beautiful waterfront community. Waiting inside the home for you upstairs are four large bedrooms, two full baths, and a laundry room. The main floor has gleaming hardwood floors with multiple spacious rooms, a sunlit family room with a marble gas fireplace and wood mantle

    Ron Wilkinson Long & Foster Real Estate, Inc.

    1160 Skyview Dr, Annapolis, MD 21409
  • /30

    $415,000

    • 3 Beds
    • 2.5 Baths
    • 1,496 Sq Ft

    1366 Almond Dr, Annapolis, MD 21409

    Sought after townhome in the Walnut Ridge community! This newly updated home offers the perfect blend of style and functionality across two levels. The heart of the home showcases a stunning new kitchen featuring crisp white cabinets and sleek quartz countertops that flow seamlessly into the dining area - perfect for both casual meals and entertaining. The main level greets you with an inviting

    Jody Buck Cummings & Co. Realtors

    1366 Almond Dr, Annapolis, MD 21409
  • /51

    $670,000

    • 4 Beds
    • 2.5 Baths
    • 1,888 Sq Ft

    1181 Ramblewood Dr, Annapolis, MD 21409

    Beautifully Updated 4BR Colonial in Highly Sought-After Cape St. Claire! This move-in ready home has been thoughtfully modernized and offers an inviting, open flow throughout. The remodeled kitchen features updated flooring and a wall removed to create a bright, seamless connection to the family room—perfect for everyday living, hosting, and entertaining. From the kitchen, step directly onto the

    Mary Anne Long Keller Williams Realty Centre

    1181 Ramblewood Dr, Annapolis, MD 21409
  • /32

    $399,000

    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft

    1424 Millwood Ct, Annapolis, MD 21409

    This lovely townhome offers three finished levels of living space on a quiet court backing to trees. This location is ideal for commuters as it is an easy hop onto Route 50 to get anywhere you need to go, or onto College Parkway to head north to Baltimore. The cozy living room with fireplace welcomes you upon entry and there is ample room for a table in the kitchen. The main level also includes a

    Michele Deckman TTR Sotheby's International Realty

    1424 Millwood Ct, Annapolis, MD 21409
  • /4

    $872,000

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

    1217 Hampton Rd, Annapolis, MD 21409

    New Construction in Cape St. Claire. Current sales price is based on buyer getting a construction perm loan to purchase home. Please look at the documents section of the listing to see all standard features included with this home and all floor plans. Pictures shown in this listing are of a previous home built at 1216 Ramblewood Drive Annapolis, Md. also located in Cape St. Claire. Home is

    Frank Livingston Cook Real Estate Brokerage

    1217 Hampton Rd, Annapolis, MD 21409
  • /67

    $3,325,000

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

    1576 Bay Head Rd, Annapolis, MD 21409

    Welcome to 1576 Bay Head Road, a breathtaking custom-built waterfront estate on the peaceful Little Magothy River offering over an acre of privacy, 6,700 square feet of refined luxury, and direct access to the Chesapeake Bay in under five minutes. Built in 2017 and designed for modern living, this residence perfectly balances year-round comfort, elegance, and effortless waterfront enjoyment.

    Wendy Oliver Coldwell Banker Realty

    1576 Bay Head Rd, Annapolis, MD 21409
  • /27

    $475,000

    • 4 Beds
    • 2 Baths
    • 1,404 Sq Ft

    1023 Mountain Top Dr, Annapolis, MD 21409

    Charming Cape Cod with Endless Potential in Cape St. Claire! Bring your vision to life in this classic 4-bedroom, 2-bath Cape Cod located in the sought-after Cape St. Claire community. Freshly painted , hardwood floors, plenty of natural light, and ready for your personal touch. The main level features a spacious floor plan with living room and dining room combined, featuring a pellet fire

    Mary Zimmerman American Dream Realty and Management

    1023 Mountain Top Dr, Annapolis, MD 21409
  • /23

    $539,900 Open House 12/06

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft

    1031 Lake Claire Dr, Annapolis, MD 21409

    Nicely updated home in sought-after Cape St Claire. Oversized .32 acre lot.New kitchen with quartz countertops, stainless steel appliances, and high-end soft-closing shaker style cabinets. New bathroom in the basement with large walk-in shower and 48 inch vanity. Main hall bathroom updated and modern. New water conditioning system, new back deck, basement, sliding door, and some new windows.

    Steve Podwojski ABR

    1031 Lake Claire Dr, Annapolis, MD 21409
  • /32

    $555,000

    • 4 Beds
    • 2.5 Baths
    • 1,728 Sq Ft

    1247 Ramblewood Dr, Annapolis, MD 21409

    Welcome to this beautifully maintained 4-bedroom, 2.5-bath split foyer on a desirable corner lot in Cape St. Claire. The upper level features a bright open-concept kitchen, dining, and family room, perfect for entertaining, with access to a spacious deck for morning coffee or summer gatherings. The lower level offers a private primary suite, a second family room, and two bonus rooms ideal for a

    Dawn Smith Engel & Völkers Annapolis

    1247 Ramblewood Dr, Annapolis, MD 21409
  • /52

    $619,000

    • 4 Beds
    • 3.5 Baths
    • 2,667 Sq Ft

    810 Chestnut Tree Dr, Annapolis, MD 21409

    Experience Annapolis living at its best in this move-in-ready Broadneck Colonial nestled within the waterfront community of Cape St. Claire. This 4-bedroom, 3.5-bathroom home offers approximately 2,525 square feet of living space, including a fully finished lower level. Step inside to discover refinished oak hardwood floors flowing throughout the main level, a bright and open layout, and recessed

    Ani Gonzalez-Brunet Coldwell Banker Realty

    810 Chestnut Tree Dr, Annapolis, MD 21409
  • /13

    $346,000

    • 2 Beds
    • 1.5 Baths
    • 1,060 Sq Ft

    1553 Star Pine Dr, Annapolis, MD 21409

    Welcome to your new home in Whispering Woods! This charming duplex offers practical living with off-street parking and a two-car driveway. Home is located on a no through, dead end Cul-de-sac street minimizing traffic. The main level living room leads to an open concept kitchen, and dining area, complete with a half bath and shared laundry. Enjoy direct access to a ground-level deck, a spacious

    Wendy Foard Coastal Realty Maryland

    1553 Star Pine Dr, Annapolis, MD 21409
  • /42

    $525,000 Open Sat 1PM - 3PM

    • 2 Beds
    • 2 Baths
    • 1,732 Sq Ft

    901 Noah Winfield Terrace Unit 102, Annapolis, MD 21409

    Come Home for the Holidays! New Price-- Let's Make A Deal!!! Fall in love with this inviting 2-bedroom condo featuring a cozy office, 2 bathrooms, and 1732 SF of beautiful space. Enjoy high ceilings, oversized windows, and elegant crown moldings. The kitchen, with its 42" cabinets, granite counters, and stainless steel appliances, is a dream. The primary bedroom offers a charming bay window,

    Mary Beth Paganelli Long & Foster Real Estate, Inc.

    901 Noah Winfield Terrace Unit 102, Annapolis, MD 21409
  • /47

    $8,750,000

    • 5 Beds
    • 7 Baths
    • 11,269 Sq Ft

    125 S Winchester Rd, Annapolis, MD 21409

    This Severn River estate is a rare opportunity to own one of the area’s most spectacular properties. Showcasing a negative-edge pool with beach entry and hot tub, 2 private piers to accommodate a variety of vessel sizes including a 100 ft slip, sprawling yard and sweeping views of the river and Naval Academy Bridge. Imagine waking each morning to the sun sparkling off the Severn, its reflection

    Brad Kappel TTR Sotheby's International Realty

    125 S Winchester Rd, Annapolis, MD 21409
  • /82

    $1,300,000

    • Land
    • 3.92 Acres
    • $331,633 per Acre

    1836 Cherry Rd, Annapolis, MD 21409

    RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15 right of way from Burley Lane to a 35' wide fee simple area along Burley Creek and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods, abundant windows

    Karlton Morris Long & Foster Real Estate, Inc.

    1836 Cherry Rd, Annapolis, MD 21409
  • /35

    $439,900

    • 3 Beds
    • 2 Baths
    • 1,868 Sq Ft

    633 Baystone Ct, Annapolis, MD 21409

    Price just reduced! Also for Rent for $3000/Mo. Welcome to easy living on the Broadneck Peninsula! This three-level garage townhome blends comfort and flexibility with ample space to gather or unwind. The entry-level offers a versatile space—use it as a legal 4th bedroom, theater, office, or hobby room—plus a garage with extra storage for a workbench, gear - it even comes with a second fridge.

    Christine Joyce Long & Foster Real Estate, Inc.

    633 Baystone Ct, Annapolis, MD 21409
  • /22

    $400,000

    • 4 Beds
    • 3.5 Baths
    • 1,904 Sq Ft

    1742 Woodtree Cir, Annapolis, MD 21409

    SELLERS HAVE FOUND HOME OF CHOICE! New carpet and ready for you to move-in!!! Bright and spacious kitchen, fully fenced backyard looking out at trees, cut-de-sac location with lots of newer perks! Special to this home unlike many in the community is your master bedroom with it's own private bathroom. You have a nice lower level with a bedroom and full bath too! There are some nice younger

    Sandy Savani Berkshire Hathaway HomeServices Homesale Realty

    1742 Woodtree Cir, Annapolis, MD 21409
  • /45

    $680,000

    • 3 Beds
    • 2.5 Baths
    • 1,925 Sq Ft

    1138 Ramblewood Dr, Annapolis, MD 21409

    * ASSUMABLE 2.75% FHA Loan for qualified buyers * Welcome to a lovely place to call home located one block from the water in the highly desirable community of Cape Saint Claire in the Broad Neck school district. The main level is a bright and open concept with a cozy wood-burning fireplace in the living area for those upcoming chilly evenings. Double French Doors lead to a quaint, quiet, very

    Gloria Shuler Coldwell Banker Realty

    1138 Ramblewood Dr, Annapolis, MD 21409
  • /51

    $549,000

    • 4 Beds
    • 2 Baths
    • 1,643 Sq Ft

    1162 Saint George Dr, Annapolis, MD 21409

    Welcome to this beautifully maintained 4-bedroom, 2-bathroom home nestled in the highly desirable, water-privileged neighborhood of Cape St. Claire. Freshly painted throughout, this home offers a light-filled layout and a perfect blend of comfort, functionality, and access to sought-after community amenities. The main level features an inviting living room drenched in natural light, a

    Hunter Geary Hyatt & Company Real Estate, LLC

    1162 Saint George Dr, Annapolis, MD 21409
  • /33

    $699,900

    • 5 Beds
    • 3 Baths
    • 3,312 Sq Ft

    1014 St Charles Dr, Annapolis, MD 21409

    This five-bedroom, three full-bath colonial is situated on a corner lot in the desirable Cape St. Claire neighborhood of Annapolis. This home boasts a charming front porch and relaxing side patio, along with ample off-street parking including a two-car garage and four-car driveway. Step inside to find a home that is truly move-in ready, featuring fresh paint throughout, gleaming hardwood floors,

    John Burgess Samson Properties

    1014 St Charles Dr, Annapolis, MD 21409
  • /32

    $399,000

    • 2 Beds
    • 2 Baths
    • 1,235 Sq Ft

    1507 Broadneck Place Unit 404, Annapolis, MD 21409

    Welcome to the exquisite penthouse level sanctuary at 1507 Broadneck Place, Unit 404, Annapolis, MD. This elegant loft-style condominium, offering 1,235 square feet, is a testament to comfort and convenience. Revel in the grandeur of vaulted ceilings and the abundance of natural light that cascades through expansive windows, enhancing every corner of this remarkable home. Thoughtfully designed,

    Jaime Watt Compass

    1507 Broadneck Place Unit 404, Annapolis, MD 21409
  • /10

    $160,000

    • Land
    • 0.21 Acre
    • $761,905 per Acre

    1167 Green Holly Dr, Annapolis, MD 21409

    Welcome to the sought-after community of Cape St. Claire! This lot is being offered as an addition to a home for sale. Please contact the county for possible development.

    Darlene Winegardner RE/MAX Executive

    1167 Green Holly Dr, Annapolis, MD 21409
  • /5

    $600,000

    • Land
    • 7.83 Acres
    • $76,628 per Acre

    0 Shot Town Rd Unit MDAA2113200, Arnold, MD 21012

    Amazing location, minutes to Annapolis and the Bay Bridge. Easy commute to DC. Incredible opportunity to own a beautiful parcel of land on desirable Shot Town Road area where large estates abound. Build a sprawling estate or possible subdivision potential of three smaller lots. If you can imagine yourself here and need additional resources to build your dream home please call for more information.

    Alicia Schline GRI Berkshire Hathaway HomeServices PenFed Realty

    0 Shot Town Rd Unit MDAA2113200, Arnold, MD 21012
  • /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
  • /10

    $739,900

    • Land
    • 0.92 Acre
    • $804,239 per Acre

    1440 Whitehall Rd, Annapolis, MD 21409

    Commercially zoned C-1 pad site available adjacent to McDonald's and Wendy's. Just shy of 1 acre. Public Utilities. Great visibility from Rt. 50. Build your office building, a restaurant, retail center, mixed use building, residential apts or condos over ground floor commercial, etc. See documents section for more information.

    Timothy Hogan Hogan Companies Residential

    1440 Whitehall Rd, Annapolis, MD 21409
  • /7

    $739,900

    • Land
    • 1.49 Acres
    • $496,577 per Acre

    1444 Whitehall Rd, Annapolis, MD 21409

    1.485 acre RLD zoned parcel/ lot available adjacent to McDonald's, Wendy's. Potential uses include daycare, veterinarian, assisted living, club, group home, kennel, plant nursery, produce stand, etc. All utilities are available. Easy access on and off of Rt. 50. Refer to documents section.

    Timothy Hogan Hogan Companies Residential

    1444 Whitehall Rd, Annapolis, MD 21409
  • /2

    $1,995,000

    • Land
    • 23.33 Acres
    • $85,512 per Acre

    1016 E College Pkwy, Annapolis, MD 21409

    23-acre parcel zoned primarily R-1, with some O-S. Preliminary engineering work indicates the property can be subdivided and coul support multiple residential lots. The concept drawing attached.

    Alex Tower Sears TTR Sotheby's International Realty

    1016 E College Pkwy, Annapolis, MD 21409
  • /39

    $489,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,318 Sq Ft

    78 Old Mill Bottom Rd N Unit 107, Annapolis, MD 21409

    Welcome to brand-new luxury living at Element at Mill Creek, a new construction community of modern condominiums designed for style, comfort, and convenience. This spacious, light-filled home offers southern exposure and a private balcony with serene views of lush forest retention—perfect for relaxing or entertaining. Inside, enjoy a chef-inspired kitchen with quartz countertops, upgraded

    Dee Hodge McWilliams/Ballard, Inc.

    78 Old Mill Bottom Rd N Unit 107, Annapolis, MD 21409

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