37

Homes for Sale near Hillsmere Elementary School

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  • /46

    $2,895,000

    $250K PRICE DROP
    • 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
  • /79

    $10,500,000

    $1M PRICE DROP
    • 6 Beds
    • 10 Baths
    • 10,745 Sq Ft

    3285 Harness Creek Rd, Annapolis, MD 21403

    Located on a private 2.5-acre lot in Wimbledon Farms, this waterfront estate home, designed by Cathy Purple Cherry and constructed by West River Builders, is truly a masterpiece in design and quality. The 3-level home – complete with elevator -- takes full advantage of its waterfront setting that includes 400 ft of shoreline. Facing Quiet Waters Park, the ever-changing view includes brilliant

    Agent Photo

    Reid Buckley

    Long & Foster Real Estate, Inc.

    (833) 366-2950

    3285 Harness Creek Rd, 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.

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 431-3849

    113 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
  • /50

    $849,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,474 Sq Ft

    3268 Kitty Duvall Dr, Annapolis, MD 21403

    Our Adams model with a 2' extenstion will be built at this beautiful location near Duvall Creek. Home is priced at the base house only - act fast to choose the options and additions to make this home your own. Photos are of the model with optional In-Law Suite. Contact Listing Agent to schedule appointment.

    Agent Photo

    Jamie Richardson

    RE/MAX United Real Estate

    (410) 498-8016

    3268 Kitty Duvall Dr, Annapolis, MD 21403
  • /88

    $1,025,000

    $25K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,800 Sq Ft

    3249 Arundel on The Bay Rd, Annapolis, MD 21403

    VIRTUAL TOUR: Buyer may keep all furnishings if desired, all items in garage will be removed prior to sale. Welcome to 3249 Arundel on the Bay Road — where coastal charm meets timeless character in one of Annapolis’ most sought-after waterfront communities. Nestled in the heart of Arundel on the Bay, this beautifully positioned home offers the rare opportunity to enjoy true Chesapeake Bay living

    Justin Walker Keller Williams Flagship

    3249 Arundel on The Bay Rd, Annapolis, MD 21403
  • /49

    $350,000

    • 3 Beds
    • 2.5 Baths
    • 1,692 Sq Ft

    20 Ironstone Ct Unit 20 F, Annapolis, MD 21403

    Beautiful end-unit townhome located in the desirable Annapolis Overlook community, featuring a sunny garden and charming white picket fence. This well-designed home offers an inviting open floor plan with spacious living and dining areas, a living room with a charming bump-out window, a well-appointed kitchen with pantry storage, and a convenient main-level half bath. Recent updates include a new

    Wendy Foard Coastal Realty Maryland

    20 Ironstone Ct Unit 20 F, Annapolis, MD 21403
  • /37

    $1,064,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 4,336 Sq Ft

    Fitzgerald Plan at Parkeside Preserve - Manor, Annapolis, MD 21403

    This expansive two-story home showcases a gracious design with abundant room to grow and entertain. Off the foyer is a formal dining room that complements the casual nook and breakfast room, plus a gourmet kitchen and a Great Room with a charming fireplace. On the second floor is a loft surrounded by three secondary bedrooms and a luxurious owner’s suite with a spa-style bathroom. A lower-level

    Lennar Builder
    201 Bonny Way Unit 36036624, Annapolis, MD 21403
  • /47

    $739,000

    $30K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,348 Sq Ft

    118 Treblis Way, Annapolis, MD 21403

    Price Reduced! Modern and “like-new” townhome ideally located just minutes to Downtown Annapolis and Eastport, offering easy access to waterfront dining, marinas, and shopping! This nearly new construction home at 118 Treblis Way showcases modern style, thoughtful enhancements, and effortless living in a prime Annapolis location. This home (Largest Model / 4 Levels) has been meticulously improved

    Joanna Dalton Coldwell Banker Realty

    118 Treblis Way, Annapolis, MD 21403
  • /12

    $1,800,000

    • Land
    • 2.07 Acres
    • $869,565 per Acre

    927 Old Annapolis Neck Rd, Annapolis, MD 21403

    Rare Builder Opportunity – Prime Minor Subdivision in Annapolis, MD (Anne Arundel County)Exceptional opportunity for builders and investors to acquire a newly divided minor subdivision totaling over 2 acres in highly desirable Annapolis, MD. These spacious, 4 buildable lots offer the perfect setting to create luxury custom homes in a sought-after location.Ideally situated just a couple of

    Ana Lopez Equity Property Investments

    927 Old Annapolis Neck Rd, Annapolis, MD 21403
  • /75

    $1,250,000

    • 5 Beds
    • 4.5 Baths
    • 4,692 Sq Ft

    128 Stilly Way, Annapolis, MD 21403

    Move-in ready and beautifully upgraded, welcome to 128 Stilly Way — a barely lived-in showpiece located in Annapolis’ sought-after Parkside Preserve community. Built in 2024 and offered in pristine condition, this exceptional residence combines the advantages of brand-new construction with the convenience of immediate enjoyment. No builder delays, no design center decisions, and no construction

    Dee Dee McCracken Coldwell Banker Realty

    128 Stilly Way, Annapolis, MD 21403
  • /35

    $709,000

    $6K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 1,809 Sq Ft

    110 Kuethe Dr, Annapolis, MD 21403

    An absolute must see! Stunning 4 bed 3 1/2 bath updated home in sought after Hillsmere Shores. This home just had cosmetic upgrades including but not limited to fresh paint throughout, new carpet, new fixtures, new appliances more. Home features two bedrooms upstairs to include a primary with his and hers walk in closets and a spa like primary bath. The second floor boasts two additional

    Meghan Winlack JAK Real Estate

    110 Kuethe Dr, Annapolis, MD 21403
  • /75

    $600,000

    $599K PRICE INCREASE
    • 3 Beds
    • 3.5 Baths
    • 1,812 Sq Ft

    3320 Arundel on The Bay Rd, Annapolis, MD 21403

    Welcome to 3320 Arundel on the Bay Road—where relaxed coastal living meets thoughtful design in the water-privileged community of Oyster Harbor. This beautifully maintained and upgraded 3-bedroom, 3.5-bath coastal-style home offers the perfect blend of indoor comfort and outdoor enjoyment. Inside, you’ll find an upgraded and inviting open plan design complemented by a cozy wood-burning fireplace,

    Creig Northrop Northrop Realty

    3320 Arundel on The Bay Rd, Annapolis, MD 21403
  • /75

    $1,750,000

    • 5 Beds
    • 4 Baths
    • 4,589 Sq Ft

    1207 Thomas Point Ct, Annapolis, MD 21403

    WELCOME TO THIS BEAUTIFULLY DESIGNED 5/6 BEDROOM, 4 FULL BATH BRICK BEAUTY IN THE HIGHLY SOUGHT AFTER WATER-PRIVILEGED COMMUNITY OF FISHING CREEK FARM! FROM THE MOMENT YOU ENTER, THE HOME FEELS BOTH ELEVATED AND INVITING WITH WELL-APPOINTED SPACES, NATURAL FLOW, AND QUALITY FINISHES THROUGHOUT. THE MAIN LEVEL OFFERS A TWO STORY FOYER AND A HOME OFFICE (OR MAIN LEVEL BEDROOM) WITH PLANTATION

    Kellie Gough McLendon Long & Foster Real Estate, Inc.

    1207 Thomas Point Ct, Annapolis, MD 21403
  • /13

    $25,000

    • Land
    • 17,859 Sq Ft
    • $60,976 per Acre

    1227 Creek Dr, Annapolis, MD 21403

    ONLINE AUCTION: Bidding begins 06/11/2026 @ 10:00 AM. Bidding ends 06/15/2026 @ 1:00 PM. List Price is Suggested Opening Bid. Deposit: $5,000. Tucked inside the sought-after Oyster Harbor community of Annapolis, this 0.41-acre homesite at 1227 Creek Dr offers something increasingly rare in Anne Arundel County: land in an established waterfront neighborhood just minutes from the heart of

    Adam Shpritz

    1227 Creek Dr, Annapolis, MD 21403
  • /47

    $710,000

    • 3 Beds
    • 2.5 Baths
    • 1,758 Sq Ft

    1180 Bay Highlands Dr, Annapolis, MD 21403

    Beautifully maintained and filled with natural light, this inviting home offers an open floor plan with vaulted ceilings, hardwood floors, and comfortable living spaces designed for both relaxing and entertaining. The spacious primary suite features a private sitting area and en-suite bath, while the cozy fireplace and rear deck create the perfect setting for everyday living. A fenced backyard

    Gary Durand CENTURY 21 New Millennium

    1180 Bay Highlands Dr, Annapolis, MD 21403
  • /41

    $799,900

    Open Sat 1PM - 3PM $25K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,144 Sq Ft

    3280 Arundel on The Bay Rd, Annapolis, MD 21403

    Welcome to this beautifully maintained custom built Tudor Style home! With a primary suite and full bath on the main level and another primary suite with full bath on the upper level, this home is perfect for multi-generational living! The upper level features 3 spacious bedrooms and 2 full baths; the main level has 1 bedroom and 1.5 bath; and the lower level has another full bath and several

    Deanna Marshall The KW Collective

    3280 Arundel on The Bay Rd, Annapolis, MD 21403
  • /3

    $525,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,668 Sq Ft

    1354 Moyer Rd, Annapolis, MD 21403

    Remarks and professional photos will be uploaded soon

    Nick Skudrna Long & Foster Real Estate, Inc.

    1354 Moyer Rd, Annapolis, MD 21403
  • /47

    $499,999

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    3365 Arundel on The Bay Rd, Annapolis, MD 21403

    Welcome Home!!! Beautiful Single Family Home, a peaceful retreat nestled in the water-privileged community of Oyster Harbor. Updates include all new oak hardwood flooring, custom kitchen cabinets with island and lots of counter space, quartz countertops and stainless steel appliances, sun filled living room, dining room, upscale bathrooms w/ custom tile and vanities, large bedrooms, private

    Olisa Akpati Fairfax Realty Select

    3365 Arundel on The Bay Rd, Annapolis, MD 21403
  • /33

    $345,000

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    40 Ironstone Ct Unit J, 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 Unit J, Annapolis, MD 21403
  • /45

    $1,079,990

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 4,483 Sq Ft

    Admiral Plan at Parkeside Preserve - Manor, Annapolis, MD 21403

    The largest floorplan in this collection, this expansive two-story home combines comfort with modern elegance. Standing at the heart of the first floor is an open-plan Great Room with a center fireplace, which melds into a well-equipped kitchen and both casual and formal dining areas to prioritize ease of living. All four bedrooms and a loft occupy the top level, including the lavish owner’s

    Lennar Builder
    201 Bonny Way Unit 36036625, Annapolis, MD 21403
  • /58

    $594,000

    • 4 Beds
    • 2 Baths
    • 1,679 Sq Ft

    129 Meade Dr, Annapolis, MD 21403

    Nestled in one of Annapolis's most beloved water-oriented communities, this 4-bedroom, 2 full bath home offers the space, updates, and lifestyle you've been waiting for. The spacious kitchen is perfect for entertaining with a passthrough window to make serving an ease. Unwind on the screened porch or take full advantage of the large fenced yard — perfect for garden parties or simply enjoying the

    Rachel Gontkovic EXP Realty, LLC

    129 Meade Dr, Annapolis, MD 21403
  • /3

    $500,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft

    406 Holly Dr, Annapolis, MD 21403

    Darlene Winegardner RE/MAX Executive

    406 Holly Dr, Annapolis, MD 21403
  • /50

    $10,850,000

    • 4 Beds
    • 7 Baths
    • 8,264 Sq Ft

    3344 Harness Creek Rd, Annapolis, MD 21403

    An extraordinary expression of waterfront luxury, this architecturally significant estate represents a rare convergence of world class design, craftsmanship, and lifestyle. Located within the prestigious enclave of Wimbledon Farms, surrounded by grand estates and moments from local vineyards and equestrian facilities, the residence was masterfully conceived by acclaimed architect Scarlett

    Brad Kappel TTR Sotheby's International Realty

    3344 Harness Creek Rd, Annapolis, MD 21403
  • /30

    $585,000

    • 3 Beds
    • 2.5 Baths
    • 2,160 Sq Ft

    3448 Cohasset Ave, Annapolis, MD 21403

    Located in the sought-after waterfront community of Arundel on the Bay, this 3-bedroom, 2.5-bath rancher offers relaxed coastal living with stunning bay views just minutes from downtown Annapolis. Stroll just blocks to the community beach, dock, boat ramp and playground to experience the charm of Chesapeake Bay living. Inside, an open floor plan features a cozy family room with a wood-burning

    Sarah Ernest Cummings & Co. Realtors

    3448 Cohasset Ave, Annapolis, MD 21403
  • /28

    $298,500

    $12K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,103 Sq Ft

    10 Sandstone Ct, Annapolis, MD 21403

    Welcome to this fully renovated, single level condo on the 2nd floor of the building. One of the most recently updated 2-bedroom unit in the community, featuring brand-new flooring throughout and a gorgeous new kitchen with granite countertops, new stainless steel appliances, and other modern finishes. The open-concept living area is spacious and inviting. Community amenities include an outdoor

    Branden Schroeder GybeSet Homes

    10 Sandstone Ct, Annapolis, MD 21403
  • /3

    $50,000

    • Land
    • 10,018 Sq Ft
    • $217,391 per Acre

    3338 Arundel on The Bay Rd, Annapolis, MD 21403

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group Website Bidding Platform Bidding begins 5/1/2026 @ 10:00 AM. Bidding ends 5/5/2026 @ 12:45 PM. List Price is Suggested Opening Bid. Deposit: $10,000. This +/- 10,000 ft2 parcel of land is located in Annapolis, MD within Anne Arundel County. It is just minutes away to Fishing Creek and Thomas Point Park. It offers easy access to

    Adam Shpritz Ashland Auction Group LLC

    3338 Arundel on The Bay Rd, Annapolis, MD 21403
  • /66

    $635,000

    • 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
  • /59

    $1,125,000

    Open Thu 4PM - 7PM $25K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,288 Sq Ft

    996 Headwater Rd, Annapolis, MD 21403

    Waterfront home nestled in the serene enclave of Kitty Creek; located right off the South River with easy access to the Chesapeake Bay. This recently updated home offers the perfect blend of luxury, comfort, and waterfront living. Inside, you’re welcomed by refinished hardwood floors and abundant natural light. The updated kitchen features new GE stainless steel appliances and opens to a cozy

    Amanda Greenfield Engel & Völkers Annapolis

    996 Headwater Rd, Annapolis, MD 21403
  • /51

    $750,000

    $50K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 1,964 Sq Ft

    1307 Blackwalnut Ct, Annapolis, MD 21403

    Tucked away on a quiet cul-de-sac, this beautifully maintained single-family home offers the perfect blend of privacy, space, and lifestyle. Situated on nearly half an acre backing to Blackwalnut Creek and serene wooded views, the outdoor setting is truly exceptional with a large play area, cozy fire pit, professional landscaping, irrigation system, and landscape lighting. Inside, you’ll find

    Sarah Martin Long & Foster Real Estate, Inc.

    1307 Blackwalnut Ct, Annapolis, MD 21403
  • /40

    $299,900

    $5K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,229 Sq Ft

    40 Greystone Ct Unit L, Annapolis, MD 21403

    Welcome to this fully renovated penthouse condo in the highly desirable Annapolis Overlook community. This spacious 2-bedroom, 2-bath residence features soaring 10-foot ceilings in the main living area, creating an airy, open feel filled with natural light, along with a cozy wood-burning fireplace perfect for cooler evenings. The thoughtfully designed open-concept layout flows seamlessly from the

    Kara Shaffer Engel & Völkers Annapolis

    40 Greystone Ct Unit L, Annapolis, MD 21403
  • /19

    $655,000

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,725 Sq Ft

    420 Edgemere Dr, Annapolis, MD 21403

    Welcome to your beautifully reimagined home in sought-after Hillsmere Shores—where timeless design meets effortless, move-in-ready living. This thoughtfully renovated 4-bedroom, 2-bath residence has been completely refreshed from top to bottom. At the heart of the home, a brand-new kitchen showcases modern finishes, stylish cabinetry, and all-new appliances, creating a space that’s as functional

    Brent Hardie TTR Sotheby's International Realty

    420 Edgemere Dr, Annapolis, MD 21403
  • /51

    $1,025,000

    Open Sat 1PM - 3PM
    • 4 Beds
    • 3 Baths
    • 4,061 Sq Ft

    124 E Bay View Dr, Annapolis, MD 21403

    Welcome to 124 E Bay View Drive, beautifully remodeled and ideally located in Hillsmere Shores, one of Annapolis’ most beloved water-oriented communities. Set along picturesque East Bay View Drive with water views, this thoughtfully updated home is just one block from the neighborhood beach with stunning water views, around the corner from the community marina, and a block away from the boat ramp

    Jennifer Gregorski Washington Fine Properties

    124 E Bay View Dr, Annapolis, MD 21403
  • /55

    $1,048,500

    Open Sun 10AM - 12PM $77K PRICE DROP
    • 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
  • /19

    $675,000

    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    3328 Shore Dr, Annapolis, MD 21403

    Amazing opportunity! Situated in one of Annapolis’ most desirable waterfront communities, Oyster Harbor, 3328 Shore Drive offers a premier corner-lot location with beautiful second-floor water views. Enjoy the coastal lifestyle with easy access to marinas, parks, the community beach, local dining, and the charm of nearby historic Annapolis. This property presents an incredible opportunity for

    Joanna Dalton Coldwell Banker Realty

    3328 Shore Dr, Annapolis, MD 21403
  • /74

    $1,949,000

    Open Sat 3PM - 5PM $51K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,620 Sq Ft

    3712 Gateshead Dr, Annapolis, MD 21403

    Price reduced!!! Nestled along the banks of Watergate Harbor with direct access to the South River, in the prestigious Watergate neighborhood of Annapolis, 3712 Gateshead Drive offers the ultimate waterfront lifestyle with waterviews from every room in the home. When you enter the home you are greeted with the marble flooring in the foyer which transitions beautifully to the gleaming hardwood

    Melissa Murray Compass

    3712 Gateshead Dr, Annapolis, MD 21403
  • /37

    $295,000

    $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,336 Sq Ft

    40 Greystone Ct Unit G, Annapolis, MD 21403

    Turnkey Investment Opportunity – 2 Bed, 2 Bath Condo with Tenant in Place + Rental Upside.Excellent opportunity for investors seeking immediate rental income with future growth potential. This well-maintained 2-bedroom, 2-bathroom condo is currently leased at $2,200/month, providing steady cash flow from day one, with market rents estimated around $2,600/month—offering clear upside.The

    Ramtin Zadeh Long & Foster Real Estate, Inc.

    40 Greystone Ct Unit G, Annapolis, MD 21403
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