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Explore Similar Homes Within 2 Miles of Highland Beach, MD

  • 933 Breakwater Dr, Annapolis, MD 21403
    933 Breakwater Dr, Annapolis, MD 21403
    933 Breakwater Dr, Annapolis, MD 21403
    /20

    $390,000

    • 2 Beds
    • 2.5 Baths
    • 1,319 Sq Ft

    933 Breakwater Dr, Annapolis, MD 21403

    This spacious and well-maintained townhouse offers comfortable living in a highly desirable Annapolis location. The main level features a welcoming living room centered around a classic wood-burning fireplace, creating a warm focal point and cozy atmosphere, while the French doors provide access to the backyard, allowing natural light to fill the space while offering an easy transition to outdoor

    Agent Photo

    Scott Smolen

    RE/MAX Leading Edge

    (443) 323-0308

    933 Breakwater Dr, Annapolis, MD 21403
  • 79 Windwhisper Ln, Annapolis, MD 21403
    79 Windwhisper Ln, Annapolis, MD 21403
    79 Windwhisper Ln, Annapolis, MD 21403
    /21

    $629,999

    • 4 Beds
    • 3.5 Baths
    • 2,560 Sq Ft

    79 Windwhisper Ln, Annapolis, MD 21403

    Motivated Sellers!! Price Just Improved!! Rare Opportunity in an Amazing Annapolis Neighborhood! Welcome to 79 Windwhisper. A beautiful 4 bedroom, 2500 sq foot, 3.5 bath home with an office, located in one of Annapolis’ most desirable neighborhoods. This well-maintained property offers numerous recent updates, including new carpet, hardwood flooring on main level, updated bathrooms, flooring,

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    Kristen Quinn

    Realty Navigator

    (443) 402-3711

    79 Windwhisper Ln, Annapolis, MD 21403
  • 111 Janwall St, Annapolis, MD 21403
    111 Janwall St, Annapolis, MD 21403
    /2

    $540,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,754 Sq Ft

    111 Janwall St, Annapolis, MD 21403

    Charming 3-Bedroom Home on Quiet Cul-de-Sac Near Downtown Annapolis Welcome to this beautifully maintained 3-bedroom, 2.5-bath single-family home, perfectly situated on a peaceful cul-de-sac just minutes from downtown Annapolis. Offering a blend of comfort, convenience, and charm, this home is ideal for both relaxing and entertaining. Step inside to find a bright and inviting interior with a

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    Amy Juras

    Long & Foster Real Estate, Inc.

    (443) 940-6438

    111 Janwall St, Annapolis, MD 21403
  • 13 Alder Rd, Eastport, MD 21403
    13 Alder Rd, Eastport, MD 21403
    /2

    $499,000 Coming Soon

    • 4 Beds
    • 1.5 Baths
    • 1,320 Sq Ft

    13 Alder Rd, Eastport, MD 21403

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    Mr. K Oyedele

    Cornerstone Properties and Financial Services LLC

    (410) 376-5350

    13 Alder Rd, Eastport, MD 21403
  • 203 Victor Pkwy Unit H, Annapolis, MD 21403
    203 Victor Pkwy Unit H, Annapolis, MD 21403
    203 Victor Pkwy Unit H, Annapolis, MD 21403
    /29

    $249,000

    • 2 Beds
    • 2 Baths
    • 956 Sq Ft

    203 Victor Pkwy Unit H, Annapolis, MD 21403

    Welcome to Fairwinds of Annapolis, this delightful 2nd floor 2-bedroom, 2-bathroom garden apartment offers a perfect blend of comfort and convenience. (Furnace 2021) The open kitchen floor plan invites you to experience a warm and inviting atmosphere, ideal for entertaining over the breakfast bar. Natural light floods the living spaces, creating a cozy ambiance. The neutral kitchen features a

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    Elizabeth Penttinen

    Coldwell Banker Realty

    (443) 313-7960

    203 Victor Pkwy Unit H, Annapolis, MD 21403
  • 796 Fairview Ave Unit 796 F, Annapolis, MD 21403
    796 Fairview Ave Unit 796 F, Annapolis, MD 21403
    796 Fairview Ave Unit 796 F, Annapolis, MD 21403
    /37

    $315,000

    • 1 Bed
    • 1 Bath
    • 756 Sq Ft

    796 Fairview Ave Unit 796 F, Annapolis, MD 21403

    Welcome to effortless waterfront living in the sought-after Severn House community! This charming 1-bedroom, 1-bath condo offers the perfect blend of tranquility and Annapolis lifestyle—whether you're paddleboarding out for your morning coffee, hopping on the water taxi for an evening in town, or enjoying sunset cruises from your own rented boat slip. Spend your days lounging by the waterfront

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    Jennifer Marsh

    Cummings & Co. Realtors

    (443) 364-2372

    796 Fairview Ave Unit 796 F, Annapolis, MD 21403
  • 50 Hearthstone Ct, Annapolis, MD 21403
    50 Hearthstone Ct, Annapolis, MD 21403
    50 Hearthstone Ct, Annapolis, MD 21403
    /37

    $360,000

    • 3 Beds
    • 2.5 Baths
    • 1,620 Sq Ft

    50 Hearthstone Ct, Annapolis, MD 21403

    NEW KITCHEN just installed! The eat-in kitchen has been updated with NEW tall, white kitchen cabinetry w/brushed bronze handles, NEW upgraded quartz countertops,NEW lighting, freshly painted, and boasts all stainless steel appliances including a gas range, french door refrigerator, dishwasher, and microwave—all installed within the past year. Enjoy Annapolis living with a community pool and

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    Sandy Wing

    RE/MAX Leading Edge

    (410) 989-4664

    50 Hearthstone Ct, Annapolis, MD 21403
  • 113 Stilly Way, Annapolis, MD 21403
    113 Stilly Way, Annapolis, MD 21403
    113 Stilly Way, Annapolis, MD 21403
    /13

    $1,079,990 New Construction

    • 4 Beds
    • 4.5 Baths
    • 4,700 Sq Ft

    113 Stilly Way, Annapolis, MD 21403

    Spacious and elegant, this 4-bedroom, 4.5-bath home offers approximately 4,400 sq. ft., with the option to expand to 5,300 sq. ft. with a fourth level. The gourmet kitchen features double wall ovens (upper with air-fry), a 36" gas cooktop, and choice of cabinetry or stainless steel hood. Enjoy a sunroom, cozy fireplace, 9-foot ceilings on all levels, and a finished basement with full bath.

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    Terri Hill

    Builder Solutions Realty

    (410) 431-3849

    113 Stilly Way, Annapolis, MD 21403
  • 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.

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    Terri Hill

    Builder Solutions Realty

    (443) 222-1215

    116 Stilly Way, Annapolis, MD 21403
  • 2018 Quay Village Ct Unit 201, Annapolis, MD 21403
    2018 Quay Village Ct Unit 201, Annapolis, MD 21403
    2018 Quay Village Ct Unit 201, Annapolis, MD 21403
    /70

    $750,000

    • 3 Beds
    • 3 Baths
    • 1,645 Sq Ft

    2018 Quay Village Ct Unit 201, Annapolis, MD 21403

    Welcome to an exceptional living experience at Chesapeake Harbour, where this well maintained 3 bedroom, 3 full bath condo offers not just a home but a lifestyle. Perfectly situated in a premium location, this residence boasts breathtaking views of the Bay Bridge and the sparkling waters of the Bay, providing a serene backdrop to your daily life. Step into a well-designed space that seamlessly

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    Lorna Kaim

    Compass

    (410) 305-9422

    2018 Quay Village Ct Unit 201, Annapolis, MD 21403
  • 48 Rockwell Ct, Annapolis, MD 21403
    48 Rockwell Ct, Annapolis, MD 21403
    48 Rockwell Ct, Annapolis, MD 21403
    /21

    $350,000

    • 2 Beds
    • 1.5 Baths
    • 1,222 Sq Ft

    48 Rockwell Ct, Annapolis, MD 21403

    This is a great opportunity to get into Annapolis at an affordable price! Welcome to 48 Rockwell Ct, conveniently located in the Painters Hill community—just a short stroll to Downtown Annapolis and moments from Rt 665, Rt 50, West St, Annapolis Harbour Center, Annapolis Mall, and so much more. The layout is simple, spacious, and efficient—offering everything you need and nothing you don’t.

    Joshua Shapiro Douglas Realty, LLC

    48 Rockwell Ct, Annapolis, MD 21403
  • 102 Oak Dr, Annapolis, MD 21403
    102 Oak Dr, Annapolis, MD 21403
    102 Oak Dr, Annapolis, MD 21403
    /22

    $498,000

    • 2 Beds
    • 2 Baths
    • 1,433 Sq Ft

    102 Oak Dr, Annapolis, MD 21403

    Located in the highly desirable Hillsmere Shores community, 102 Oak Drive offers a comfortable lifestyle in one of Annapolis’ most well-established neighborhoods. Conveniently located just minutes from downtown Annapolis, the U.S. Naval Academy, and major commuter routes, this home provides easy access to shopping, dining, and everyday essentials. Residents of Hillsmere Shores also enjoy easy

    Amy Presley Samson Properties

    102 Oak Dr, Annapolis, MD 21403
  • 99 Summerfield Dr, Annapolis, MD 21403
    99 Summerfield Dr, Annapolis, MD 21403
    99 Summerfield Dr, Annapolis, MD 21403
    /55

    $524,900

    • 4 Beds
    • 3 Baths
    • 1,980 Sq Ft

    99 Summerfield Dr, Annapolis, MD 21403

    Charming rancher in the heart of Annapolis! Hardwood throughout, updates to the kitchens and bathrooms, fully finished basement with full bathroom, screened-in porch, large backyard. 2.5 miles to Historic Downtown Annapolis, just over a mile to Eastport restaurants. Ask about 2.375% assumable FHA loan!

    Jack Papaleonti Academy Realty Inc.

    99 Summerfield Dr, Annapolis, MD 21403
  • 2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403
    2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403
    2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403
    /97

    $675,000

    • 3 Beds
    • 3 Baths
    • 1,700 Sq Ft

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

    Now is your chance to call this HOME! Welcome to this totally updated condo in the desirable Chesapeake Harbor section of Annapolis. Whether you're looking for a worry-free vacation spot or a serene place to call home, this 3-bedroom, 3 full bath sanctuary with a gourmet kitchen and totally updated baths has you covered with over 1,700 square feet of style and comfort. This Bayfront community

    Lorna Kaim Compass

    2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403
  • 22 E Lake Dr, Annapolis, MD 21403
    22 E Lake Dr, Annapolis, MD 21403
    22 E Lake Dr, Annapolis, MD 21403
    /79

    $2,550,000 Open Sat 3PM - 5PM

    • 3 Beds
    • 2.5 Baths
    • 2,338 Sq Ft

    22 E Lake Dr, Annapolis, MD 21403

    Welcome to 22 E Lake Drive! This exceptional waterfront residence offers striking architectural elements with expansive, light-filled interiors and seamless indoor-outdoor living along the Chesapeake Bay.The main level open floor plan is designed for effortless flow and everyday living. The living room anchors the space, featuring a floor-to-ceiling stone fireplace and a wall of bi-fold glass

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    22 E Lake Dr, Annapolis, MD 21403
  • 40 Ironstone Ct, Annapolis, MD 21403
    40 Ironstone Ct, Annapolis, MD 21403
    40 Ironstone Ct, Annapolis, MD 21403
    /36

    $359,999

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    40 Ironstone Ct, Annapolis, MD 21403

    Beautifully maintained 3-level townhome in the desirable Annapolis Overlook community in Annapolis! This spacious home offers approximately 1,680 sq ft with 3 bedrooms, 2.5 baths, and a functional layout designed for comfortable living. The main level features a bright living area, separate dining space, and an updated kitchen with ample cabinet storage and room for entertaining. Upstairs you’ll

    Lisa Gilmore Keller Williams Flagship

    40 Ironstone Ct, Annapolis, MD 21403
  • 30 Hearthstone Ct Unit J, Annapolis, MD 21403
    30 Hearthstone Ct Unit J, Annapolis, MD 21403
    30 Hearthstone Ct Unit J, Annapolis, MD 21403
    /38

    $295,000

    • 2 Beds
    • 2 Baths
    • 1,376 Sq Ft

    30 Hearthstone Ct Unit J, Annapolis, MD 21403

    OPEN SAT 04/04, 12-3 . PARK IN SPOT #12 RIGHT IN FRONT. Welcome to this beautifully maintained 2-bedroom, 2-bath condominium in the desirable Annapolis Overlook community, offering 1,376 square feet of comfortable living space. This inviting home features warm wood flooring and a cozy wood-burning fireplace, creating the perfect setting for both everyday living and relaxing evenings. Step outside

    Billy Barr Keller Williams Realty Delmarva

    30 Hearthstone Ct Unit J, Annapolis, MD 21403
  • 5 Silverwood Cir Unit 1, Annapolis, MD 21403
    5 Silverwood Cir Unit 1, Annapolis, MD 21403
    5 Silverwood Cir Unit 1, Annapolis, MD 21403
    /25

    $293,500 Open Sat 1PM - 3PM

    • 2 Beds
    • 2 Baths

    5 Silverwood Cir Unit 1, Annapolis, MD 21403

    Popular Fairwinds Condo is a great place to live!! Two Bedroom Two Bath with den condominium ! Newer stainless steel appliances ! Freshly painted 2026 ! Luxury Vinyl thru living areas and carpet in bedrooms! Lots of closets and storage! Extra storage area included in basement ! Master bedroom has full bath ! Updated kitchen ! New light fixtures including eyeball lights! New glass door in shower

    Bev Langley Coldwell Banker Realty

    5 Silverwood Cir Unit 1, Annapolis, MD 21403
  • 3 Elliott Rd, Annapolis, MD 21403
    3 Elliott Rd, Annapolis, MD 21403
    3 Elliott Rd, Annapolis, MD 21403
    /43

    $745,000

    • Studio
    • 2,928 Sq Ft

    3 Elliott Rd, Annapolis, MD 21403

    3 Elliott Road offers a fantastic opportunity to own a well-maintained two-unit duplex with completely separate living spaces and entrances on opposite sides of the property—ideal for investors or owner-occupants seeking rental income. Unit 1 (Vacant) is a spacious 2-bedroom, 1-bath residence featuring high ceilings, hardwood floors, and abundant natural light. The unit includes an updated

    Benjamin Mueller Innovative Properties, Inc.

    3 Elliott Rd, Annapolis, MD 21403
  • 2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403
    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403
    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403
    /67

    $595,000

    • 2 Beds
    • 2 Baths
    • 1,237 Sq Ft

    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403

    Welcome to this beautiful 2 bedroom 2 bath coveted end unit condo in the sought-after gated Chesapeake Harbour community, This home is a rare find, offering the perfect blend of privacy, natural light, and outdoor space. Inside, the additional square footage an end unit offers creates an open floor plan bathed in sunlight, thanks to windows on three sides. The living spaces are airy and inviting,

    Lorna Kaim Compass

    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403
  • 101 Huse Dr, Annapolis, MD 21403
    101 Huse Dr, Annapolis, MD 21403
    101 Huse Dr, Annapolis, MD 21403
    /45

    $800,000

    • 4 Beds
    • 2.5 Baths
    • 2,016 Sq Ft

    101 Huse Dr, Annapolis, MD 21403

    YES, YOU CAN HAVE IT ALL. Completely remodeled from top to bottom in one of the most sought-after neighborhoods around—this one checks ALL the boxes. The kitchen, the great room... this is the hub. The heart of the home. And the best part? You’re not dreaming about what it could be—the work is already done. Big island, open flow—everyone ends up here. Whether you’re cooking, hanging out, or just

    Kristi Krankowski RE/MAX One

    101 Huse Dr, Annapolis, MD 21403
  • 21 Silverwood Cir Unit 11, Annapolis, MD 21403
    21 Silverwood Cir Unit 11, Annapolis, MD 21403
    21 Silverwood Cir Unit 11, Annapolis, MD 21403
    /33

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft

    21 Silverwood Cir Unit 11, Annapolis, MD 21403

    Perched on the top floor of the sought-after Fairwinds of Annapolis community, this beautifully updated condo offers a quiet retreat with no neighbors above and serene courtyard views. Surrounded by mature trees and thoughtfully landscaped common areas, residents enjoy a well-maintained setting complete with a pool, tennis courts, tot lots, snow removal, picnic areas for grilling, bike and kayak

    Mr. Mason Lyon Northrop Realty

    21 Silverwood Cir Unit 11, Annapolis, MD 21403
  • 141 Stilly Way, Annapolis, MD 21403
    141 Stilly Way, Annapolis, MD 21403
    141 Stilly Way, Annapolis, MD 21403
    /56

    $1,125,000 Open Sun 1PM - 3PM

    • 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. She’s Annapolis. Welcome to 141 Stilly Way — a barely lived-in, fully upgraded showpiece in the sought-after Parkside Preserve, offered in true mint condition. This is not a builder sale. This is the finished product — every bump-out, every upgrade, every design decision already made at the highest level. No waiting. No construction. No

    Wendy Oliver Coldwell Banker Realty

    141 Stilly Way, Annapolis, MD 21403
  • 103 Roselawn Rd, Annapolis, MD 21403
    103 Roselawn Rd, Annapolis, MD 21403
    103 Roselawn Rd, Annapolis, MD 21403
    /33

    $380,000

    • 3 Beds
    • 2 Baths
    • 1,287 Sq Ft

    103 Roselawn Rd, Annapolis, MD 21403

    Discover the charm of this delightful ranch-style home nestled in the serene Primrose Acres neighborhood. Built in 1956, this well-maintained residence boasts 1,287 square feet of inviting living space, featuring three spacious bedrooms and two full bathrooms, perfect for comfortable living. Step inside to find a warm and welcoming atmosphere, enhanced by thoughtful interior features that create

    Rosalie Petsu Long & Foster Real Estate, Inc.

    103 Roselawn Rd, Annapolis, MD 21403
  • 1106 Mainsail Dr, Annapolis, MD 21403
    1106 Mainsail Dr, Annapolis, MD 21403
    1106 Mainsail Dr, Annapolis, MD 21403
    /57

    $895,000

    • 5 Beds
    • 2.5 Baths
    • 2,059 Sq Ft

    1106 Mainsail Dr, Annapolis, MD 21403

    At last, the one you've been waiting for. A beautiful home in a waterfront community. Move right in and start enjoying the Annapolis lifestyle. Anchorage is an amenity filled waterfront community in which the yearly HOA fee includes the use of a boat slip, community pool and more.This characterful 5 bedroom 2 1/2 bath home has approximately 2,354SF of living space and has been renovated

    Jill Windsor Long & Foster Real Estate, Inc.

    1106 Mainsail Dr, Annapolis, MD 21403
  • 2 River Dr, Annapolis, MD 21403
    2 River Dr, Annapolis, MD 21403
    2 River Dr, Annapolis, MD 21403
    /50

    $3,850,000

    • 6 Beds
    • 4.5 Baths
    • 3,818 Sq Ft

    2 River Dr, Annapolis, MD 21403

    2 River with its stunning water views of the Severn River and of the Chesapeake Bay epitomizes the Annapolis Lifestyle! Located in this beloved multi-generational community of Bay Ridge, this exquisitely renovated classic home seamlessly blends the timeless updates and fabulous original detail such as leaded glass windows and brass chandeliers. The main level has the most incredible, breezy

    Alex Tower Sears TTR Sotheby's International Realty

    2 River Dr, Annapolis, MD 21403
  • 300 Hilltop Ln Unit H, Annapolis, MD 21403
    300 Hilltop Ln Unit H, Annapolis, MD 21403
    300 Hilltop Ln Unit H, Annapolis, MD 21403
    /27

    $275,000

    • 2 Beds
    • 2 Baths
    • 1,082 Sq Ft

    300 Hilltop Ln Unit H, Annapolis, MD 21403

    Welcome to easy Annapolis living at 300 Hilltop Lane! This well-maintained 2-bedroom, 2-bath second-level condo offers over 1,000 square feet of comfortable living space with a bright, open layout perfect for everyday living and entertaining. The spacious living and dining area features beautiful hardwood flooring and abundant natural light, creating a warm and inviting atmosphere. The kitchen is

    Christopher Sidoriak Keller Williams Flagship

    300 Hilltop Ln Unit H, Annapolis, MD 21403
  • 3280 Arundel on The Bay Rd, Annapolis, MD 21403
    3280 Arundel on The Bay Rd, Annapolis, MD 21403
    3280 Arundel on The Bay Rd, Annapolis, MD 21403
    /52

    $850,000

    • 5 Beds
    • 4.5 Baths
    • 3,144 Sq Ft

    3280 Arundel on The Bay Rd, Annapolis, MD 21403

    Significant Price Improvement!! A rare opportunity! Priced to sell, won't last long. Welcome to this beautifully maintained 5 bed, 4.5 bath, colonial home situated on almost a half of acre and only 2 blocks to the Chesapeake Bay where you can hear the sounds of the ships passing by in your backyard! Located in the very desirable and relaxed Oyster Harbor Community. This move-in ready home

    Deanna Marshall The KW Collective

    3280 Arundel on The Bay Rd, Annapolis, MD 21403
  • 52 Primrose Hill Ln, Annapolis, MD 21403
    52 Primrose Hill Ln, Annapolis, MD 21403
    52 Primrose Hill Ln, Annapolis, MD 21403
    /73

    $924,900

    • 5 Beds
    • 4.5 Baths
    • 3,978 Sq Ft

    52 Primrose Hill Ln, Annapolis, MD 21403

    Modern accents meet classic Georgian design in a downtown Annapolis private enclave of customized homes. Monthly neighborhood get togethers, progressive dinners, holiday celebrations and lovingly curated green spaces for outdoor living. Self managed HOA includes yard care and snow removal for lock and leave convenience. If you’re looking for rolling acres with grass to cut weeds to pull beds to

    Richard Curtis Curtis Real Estate Company

    52 Primrose Hill Ln, Annapolis, MD 21403
  • 2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    /39

    $725,000

    • 3 Beds
    • 3 Baths
    • 1,748 Sq Ft

    2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403

    WATCH THE SUNSETS & ENJOY THE BREATHTAKING MARINA VIEWS FROM THIS BEAUTIFUL 3 BEDROOM, 3 FULL BATH CONDO IN CHESAPEAKE HARBOUR! ENJOY LIFE BY THE WATER IN THIS TURN KEY RENOVATED CONDO. BOTH THE WATERSIDE PRIMARY AND LIVING ROOM HAVE SLIDERS TO THE WATERSIDE BALCONY. FEATURES INCLUDE GOURMET KITCHEN, DESIGNER LIGHTING, NEW ENTRY WAY, COUNTERTOPS, HVAC, SLIDERS, STAINLESS STEEL APPLIANCES,

    Pamela Tierney Coldwell Banker Realty

    2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
  • 2175 Chesapeake Harbour Dr, Annapolis, MD 21403
    2175 Chesapeake Harbour Dr, Annapolis, MD 21403
    2175 Chesapeake Harbour Dr, Annapolis, MD 21403
    /44

    $2,295,000

    • 4 Beds
    • 4.5 Baths
    • 2,513 Sq Ft

    2175 Chesapeake Harbour Dr, Annapolis, MD 21403

    Indulge in resort-like living at Chesapeake Harbour, a gated community filled with amenities and stunning water views of the Chesapeake Bay. This modern and spacious 4 bedroom, 4.5 bathroom townhome with elevator spans 4 levels and just over 2,500 square feet, featuring high-end design and curated finishes. The open floor plan makes entertaining seamless and focuses the attention on the stunning

    Brad Kappel TTR Sotheby's International Realty

    2175 Chesapeake Harbour Dr, Annapolis, MD 21403
  • 10 Amberstone Ct, Annapolis, MD 21403
    10 Amberstone Ct, Annapolis, MD 21403
    10 Amberstone Ct, Annapolis, MD 21403
    /30

    $315,000

    • 2 Beds
    • 2 Baths
    • 1,138 Sq Ft

    10 Amberstone Ct, Annapolis, MD 21403

    This lovely first floor condo, conveniently located in Annapolis, has two bedrooms, a den and two full bathrooms. Open concept living room, dining area and kitchen with a nice patio overlooking the woods behind it. Ceramic floors in the front hall and kitchen. Freshly painted throughout. New carpet in the den and two bedrooms. Luxury vinyl plank flooring in the living room and dining room area.

    Wilma Richards Long & Foster Real Estate, Inc.

    10 Amberstone Ct, Annapolis, MD 21403
  • 300 Hilltop Ln Unit 300B, Annapolis, MD 21403
    300 Hilltop Ln Unit 300B, Annapolis, MD 21403
    300 Hilltop Ln Unit 300B, Annapolis, MD 21403
    /24

    $285,000

    • 2 Beds
    • 2 Baths
    • 1,078 Sq Ft

    300 Hilltop Ln Unit 300B, Annapolis, MD 21403

    Take advantage of the opportunity to own this beautifully maintained two-bedroom, two full bath condo in Annapolis. Offering convenient one-level living, this home combines comfort, updates, and an ideal location.The kitchen is thoughtfully appointed with granite countertops, stainless steel appliances, updated LED lighting, and additional seating space—perfect for casual dining or

    Kristen Swartz Taylor Properties

    300 Hilltop Ln Unit 300B, Annapolis, MD 21403
  • 100 Carroll Dr, Annapolis, MD 21403
    100 Carroll Dr, Annapolis, MD 21403
    100 Carroll Dr, Annapolis, MD 21403
    /59

    $649,000

    • 4 Beds
    • 2 Baths
    • 1,935 Sq Ft

    100 Carroll Dr, Annapolis, MD 21403

    Welcome to 100 Carroll Drive, a fully remodeled four-bedroom, two-bath split foyer in the desirable and sought-after waterfront community of Hillsmere Shores in Annapolis. The upper level features a completely renovated open-concept layout with a stunning kitchen showcasing new cabinetry, new appliances, countertops, and luxury vinyl flooring throughout, flowing seamlessly into the dining and

    Timothy Caropreso Keller Williams Flagship

    100 Carroll Dr, Annapolis, MD 21403
  • 1014 Cedar Ridge Ct, Annapolis, MD 21403
    1014 Cedar Ridge Ct, Annapolis, MD 21403
    1014 Cedar Ridge Ct, Annapolis, MD 21403
    /43

    $390,000

    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    1014 Cedar Ridge Ct, Annapolis, MD 21403

    Welcome to 1014 Cedar Ridge Ct in beautiful Annapolis , a stylish 3-bedroom, 2 full bath, 1 half bath townhome designed for easy living in a prime location (21403). This is not your typical HOA. The association fee includes roof repair and replacement, all exterior maintenance (painting and staining), landscaping, gutter cleaning, and parking lot maintenance. Inside, the home is completely

    Bob Chew Samson Properties

    1014 Cedar Ridge Ct, Annapolis, MD 21403
  • 2010 Quay Village Ct Unit 201, Annapolis, MD 21403
    2010 Quay Village Ct Unit 201, Annapolis, MD 21403
    2010 Quay Village Ct Unit 201, Annapolis, MD 21403
    /28

    $565,000

    • 2 Beds
    • 2 Baths
    • 1,489 Sq Ft

    2010 Quay Village Ct Unit 201, Annapolis, MD 21403

    Watch sunrises over the Chesapeake Bay from this airy condo in amenity-rich Chesapeake Harbour. Updated and larger than many other two-bedroom units, this second-floor condo includes a spacious loft - ideal as a family room, home office, or third bedroom. The vaulted living room ceiling, skylights, and sliding doors bring the outdoors in while showcasing bucolic views of the water and nearby

    Sarah Greenlee Morse TTR Sotheby's International Realty

    2010 Quay Village Ct Unit 201, Annapolis, MD 21403
  • 113 Bay Dr, Annapolis, MD 21403
    113 Bay Dr, Annapolis, MD 21403
    113 Bay Dr, Annapolis, MD 21403
    /34

    $3,195,000

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

    113 Bay Dr, Annapolis, MD 21403

    *****************Bay Ridge Coastal Retreat | Annapolis Waterfront Elegance******************************Welcome to one of the most coveted addresses in Annapolis, set in the sought-after waterfront community of Bay Ridge. This exceptional property rests on a level, manicured lot with sweeping views of the Chesapeake Bay -- offering a front-row seat to some of the region's most breathtaking

    Thomas Hennerty NetRealtyNow.com, LLC

    113 Bay Dr, Annapolis, MD 21403
  • 819 Janice Dr, Annapolis, MD 21403
    819 Janice Dr, Annapolis, MD 21403
    819 Janice Dr, Annapolis, MD 21403
    /37

    $1,195,000

    • 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
  • 2215 Chesapeake Harbour Dr E, Annapolis, MD 21403
    2215 Chesapeake Harbour Dr E, Annapolis, MD 21403
    2215 Chesapeake Harbour Dr E, Annapolis, MD 21403
    /68

    $2,300,000

    • 3 Beds
    • 3.5 Baths
    • 3,086 Sq Ft

    2215 Chesapeake Harbour Dr E, Annapolis, MD 21403

    Welcome to an exceptional four level townhome in the coveted Village of Chesapeake Harbour in Annapolis, where every floor captures sweeping views of the Severn River and the iconic Chesapeake Bay Bridge. An elevator services all levels, offering both convenience and comfort while enhancing the ease of everyday living. Multiple balconies and decks invite you to step outside and take in sunrise

    Stacey Stracke Douglas Realty, LLC

    2215 Chesapeake Harbour Dr E, Annapolis, MD 21403
  • 48 E Lake Dr, Annapolis, MD 21403
    48 E Lake Dr, Annapolis, MD 21403
    48 E Lake Dr, Annapolis, MD 21403
    /10

    $1,895,000

    • Land
    • 0.22 Acre
    • $8,613,636 per Acre

    48 E Lake Dr, Annapolis, MD 21403

    Last available opportunity for a buildable Waterfront lot on Lake Ogleton in the coveted community of Bay Ridge in Annapolis! This .22 acre lot has been in the same family for the past 58 years and is coming to market for the first time. With 57 feet of waterfrontage on the sparkling shores of Lake Ogleton, the possibilities are endless for building the waterfront home of your dreams! This

    Brad Kappel TTR Sotheby's International Realty

    48 E Lake Dr, Annapolis, MD 21403
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