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Homes for Sale near Hillsmere Elementary School

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  • /6

    $253,500

    $4K PRICE INCREASE
    • Land
    • 10,018 Sq Ft
    • $1,102,174 per Acre

    3354 Arundel on The Bay Rd, Annapolis, MD 21403

    Rare opportunity to build your dream coastal retreat on this premium 50' x 200' lot in the highly sought-after waterfront community of Oyster Harbor! Instantly impressive, this beautifully manicured 0.23-acre parcel features a grand, half-moon driveway that offers elegant curb appeal and effortless pull-through access for vehicles or watercraft. This cleared and pristine canvas is ready for your

    Agent Photo

    Mark Brown JR.

    Real Estate Professionals, Inc.

    3354 Arundel on The Bay Rd, Annapolis, MD 21403
  • /53

    $1,200,000

    • 5 Beds
    • 4.5 Baths
    • 5,575 Sq Ft

    139 Stilly Way, Annapolis, MD 21403

    Nearly new and beautifully appointed, this exceptional 5-bedroom home with potential for a 6th bedroom offers impressive space, sophisticated finishes, and a coveted setting backing to Quiet Waters Park. A rare main level primary suite adds convenience and luxury, while thoughtfully designed living spaces provide exceptional flexibility for entertaining, working, and relaxing. The heart of the

    Agent Photo

    Cheryl Jersey-Lecourt

    Long & Foster Real Estate, Inc.

    139 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

    Mrs. Terri E Hill

    Builder Solutions Realty

    116 Stilly Way, Annapolis, MD 21403
  • /50

    $974,990

    New Construction $125K PRICE INCREASE
    • 4 Beds
    • 2.5 Baths
    • 3,846 Sq Ft

    3268 Kitty Duvall Dr, Annapolis, MD 21403

    Construction has began on this beautiful Schaefer Homes, design!!Discover an unparalleled opportunity to own a luxurious, newly constructed Colonial masterpiece in the prestigious Oyster Harbor community. This exquisite residence, set to be completed in 2026, boasts a sprawling 0.62-acre lot, offering ample space for outdoor entertaining and serene relaxation. With 4 spacious bedrooms and 2.5

    Agent Photo

    Jamie Richardson

    RE/MAX United Real Estate

    3268 Kitty Duvall Dr, 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

    Mrs. Terri E Hill

    Builder Solutions Realty

    113 Stilly Way, 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
  • /2

    $425,000

    Coming Soon Sep 24
    • 3 Beds
    • 1 Bath
    • 1,312 Sq Ft

    293 Cedar Ln, Annapolis, MD 21403

    Welcome to 293 Cedar Lane, a classic 1963 ranch on a private .27 acre lot in the water privileged community of Hillsmere Estates, steps from Quiet Waters Park and minutes to the South River. Original hardwood floors flow through the main level, where a living room with custom built in shelving opens to a galley kitchen with an electric stove top, wall oven, and dishwasher, full of potential for

    Kara Chaffin Donofrio Long & Foster Real Estate, Inc.

    293 Cedar Ln, Annapolis, MD 21403
  • /50

    $1,750,000

    • 4 Beds
    • 5 Baths
    • 3,836 Sq Ft

    3403 Hidden River View Rd, Annapolis, MD 21403

    Experience the best of Annapolis living in the sought-after, amenities-rich community of Fishing Creek Farm. Perfectly positioned to capture beautiful water views and surrounded by lush lawns and mature landscaping, this handsome brick-front Colonial offers a rare combination of timeless architecture, flexible living spaces, and an exceptional neighborhood lifestyle.A gracious foyer

    Brad Kappel TTR Sotheby's International Realty

    3403 Hidden River View Rd, Annapolis, MD 21403
  • /68

    $6,995,000

    • 4 Beds
    • 5.5 Baths
    • 5,771 Sq Ft

    3728 Ramsgate Dr, Annapolis, MD 21403

    Set on a spectacular point of land where the South River meets the Chesapeake Bay, this extraordinary waterfront estate captures some of the most breathtaking views in Annapolis. With coveted southern exposure, the property is immersed in sunlight from dawn to dusk, creating an ever-changing backdrop of sparkling water, passing sailboats, and panoramic Chesapeake vistas.Completely

    Brad Kappel TTR Sotheby's International Realty

    3728 Ramsgate Dr, Annapolis, MD 21403
  • /45

    $730,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,242 Sq Ft

    110 Lake View Dr, Annapolis, MD 21403

    **NEW PRICE — a fresh opportunity to call Hillsmere Shores home!** Just two blocks from the community’s private beach and playground on the South River, this updated 3-bedroom, 2-bath home puts one of Hillsmere’s best amenities practically at your doorstep. Watch the sunrise at the water, afternoons at the beach, and evenings watching sailboats and ships pass along the Chesapeake Bay are all part

    Danielle Franz EXP Realty, LLC

    110 Lake View Dr, Annapolis, MD 21403
  • /13

    $15,000

    $10K PRICE DROP
    • Land
    • 17,859 Sq Ft
    • $36,585 per Acre

    1227 Creek Dr, Annapolis, MD 21403

    ONLINE AUCTION: Bidding begins 9/16/2026, 10:00 AM. Bidding ends 9/18/2026, 12:40 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 Maryland's

    Adam Shpritz Ashland Auction Group

    1227 Creek Dr, Annapolis, MD 21403
  • /49

    $799,000

    $46K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,229 Sq Ft

    100 Oak Dr, Annapolis, MD 21403

    Price Improvement! Experience the best of Annapolis living in this beautifully updated 4-bedroom, 3-bath home located in a waterfront community. This move-in-ready home offers the perfect blend of modern updates, comfortable living, and an exceptional Chesapeake Bay lifestyle.The heart of the home has also been refreshed with updated kitchen countertops and appliances (2024/2025), making it

    Lauren Emrick Innovative Properties, Inc.

    100 Oak Dr, Annapolis, MD 21403
  • /52

    $685,000

    $25K PRICE DROP
    • 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
  • /10

    $280,000

    • 2 Beds
    • 2 Baths
    • 1,010 Sq Ft

    50 Sandstone Ct, Annapolis, MD 21403

    Welcome to 50-G Sandstone Court, nestled in the desirable Annapolis Overlook community, where comfort, convenience, and easy living come together. This beautifully maintained 2-bedroom, 2-bath condominium is truly move-in ready and offers a bright, welcoming atmosphere you'll be proud to call home.Step inside to discover a spacious, open-concept living area that creates the perfect

    Karen Richardson Coldwell Banker Realty

    50 Sandstone Ct, Annapolis, MD 21403
  • /86

    $300,000

    • 2 Beds
    • 2 Baths
    • 1,217 Sq Ft

    10 Hearthstone Ct Unit B, Annapolis, MD 21403

    Welcome home to this fantastic two bedroom, two bath condo. Located on the ground level with a view of grassy area, trees, and the community pool. Open concept for the living and dining room area, with a bump out used currently as an exercise area, but it can be anything your heart desires. The modern kitchen is updated with silestone countertops, stainless appliances and the range is brand new.

    Christopher Fuller Long & Foster Real Estate, Inc.

    10 Hearthstone Ct Unit B, Annapolis, MD 21403
  • /42

    $699,990

    Open Sat 11AM - 1PM $45K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,300 Sq Ft

    104 Groh Ln, Annapolis, MD 21403

    Some neighborhoods give you an address. Hillsmere gives you a way of life. At 104 Groh Lane, you’ll find a beautifully updated four-bedroom, three-bath home with approximately 2,300 square feet of finished living space, an exceptionally versatile floor plan, and a wonderful level, fenced backyard—all within one of Annapolis’ most beloved waterfront communities. Three bedrooms and two full baths

    Wendy Oliver Coldwell Banker Realty

    104 Groh Ln, Annapolis, MD 21403
  • /31

    $750,000

    Open Sat 1PM - 3PM $50K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,144 Sq Ft

    3280 Arundel on The Bay Rd, Annapolis, MD 21403

    Significant Price Improvement! Priced to sell, incredible value. Excellent Condition. Welcome to this beautifully maintained custom built Tudor Style home in this small coastal community. NO HOA!! Pride of ownership shows! With a primary suite on the main level and another primary suite on the upper level, this home is perfect for Multi-Generational Living and Accessibility! The upper level

    Deanna Marshall The KW Collective

    3280 Arundel on The Bay Rd, Annapolis, MD 21403
  • /23

    $685,000

    • 3 Beds
    • 3.5 Baths
    • 2,392 Sq Ft

    116 Bonny Way, Annapolis, MD 21403

    I am excited to share details regarding a stunning three-story townhouse that perfectly blends classic Annapolis living with modern luxury. One of the few homes with a wooded view from your living room.Located just minutes from downtown Annapolis, this home offers an ideal lifestyle with easy access to Washington D.C. or Baltimore. It is situated just steps from a trail leading directly

    Della Edwards Curtis Real Estate Company

    116 Bonny Way, Annapolis, MD 21403
  • /25

    $1,000,000

    • 5 Beds
    • 4.5 Baths
    • 9,960 Sq Ft

    1254 Washington Dr, Annapolis, MD 21403

    Rare waterfront redevelopment opportunity in Annapolis. The existing structure is a complete shell and requires a full renovation or rebuild. Ideal for investors, builders, or buyers looking to design and construct a custom waterfront home from the ground up.Located along the protected waters of Oyster Cove, the property includes a deep-water pier and boat house. The existing footprint

    Nadia Aminov Long & Foster Real Estate, Inc.

    1254 Washington Dr, Annapolis, MD 21403
  • /28

    $694,999

    $35K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,160 Sq Ft

    117 Pinecrest Dr, Annapolis, MD 21403

    Stunning 2400 sq ft remodeled home in Hillsmere! Situated on a lovely street and a large flat lot, this breathtaking home has been fully remodeled and offers some of the nicest finishes in the community! Entering through a charming 3 season room, youll be greeted by brand new lvp flooring throughout the home, a spacious family room that opens into your brand new kitchen. Kitchen features include

    Alex Estill Long & Foster Real Estate, Inc.

    117 Pinecrest Dr, Annapolis, MD 21403
  • /83

    $875,000

    $25K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,288 Sq Ft

    3249 Arundel on The Bay Rd, Annapolis, MD 21403

    Welcome to 3249 Arundel On The Bay Road, an exceptional custom contemporary estate situated on over one private acre in one of Annapolis’ most exclusive waterfront communities. Appraised at $1,097,000 in January 2026, this remarkable property offers an incredible opportunity for instant equity while delivering the luxury lifestyle today's discerning buyers seek. A dramatic two-story foyer

    Montaz McCray Keller Williams Capital Properties

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

    $425,000

    • 2 Beds
    • 1 Bath
    • 1,020 Sq Ft

    3545 Newport Ave, Annapolis, MD 21403

    Professional photography coming soon...Opportunity abounds in the sought after, water-privileged community of Arundel on the Bay! Located one house from the water, 30 yards from the beach, and sits on a double lot. This property offers potential for an investor, builder, or buyer looking to renovate using an FHA 203(k) or similar renovation loan. The home features two bedrooms, a den/office

    Ryan Briggs Anne Arundel Properties, Inc.

    3545 Newport Ave, Annapolis, MD 21403
  • /33

    $1,119,290

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

    112 Stilly Way, Annapolis, MD 21403

    Step into this impressive 4,336 square foot two-story home, where a welcoming foyer leads to a spacious open-concept main level designed for effortless entertaining and everyday living. The Great Room centers around a charming fireplace and flows seamlessly into the dining area and chef-inspired kitchen, complete with Frigidaire stainless steel appliances, Timberlake cabinetry with crown moulding

    Lennar Builder
    112 Stilly Way, Annapolis, MD 21403
  • /39

    $530,000

    Open Sun 12PM - 2PM $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,555 Sq Ft

    1252 Creek Dr, Annapolis, MD 21403

    Stunning Oyster Harbor – Coastal Charm Meets ComfortThis gorgeous property blends comfort, charm, and the best of coastal living. Nestled in the highly desirable Oyster Harbor community, residents enjoy water privileges and access to a sandy beach, picnic area, fishing pier, and playground—all just a short walk from the front door. Additional amenities include a community marina, boat

    Jessica Ricciardi Welder Keller Williams Flagship

    1252 Creek Dr, Annapolis, MD 21403
  • /33

    $329,000

    $31K 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

    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
  • /33

    $750,000

    Open Sat 12PM - 2PM
    • 3 Beds
    • 2.5 Baths
    • 2,289 Sq Ft

    304 Saddle Ridge Rd, Annapolis, MD 21403

    Pics are up! Pottery Barn Perfect best describes this perfect house in the sought after community of Hunt Meadow! Everything is done! Move right in! This 3/4 bedroom, 2.5 bath home has barn doors, great moldings, newer siding and windows, great deck overlooking a perfect sized fenced yard with Thermospa Hot Tub. Irrigation with rain sensor. Upgraded lighting. Kitchen and baths are renovated,

    Pamela Tierney Coldwell Banker Realty

    304 Saddle Ridge Rd, 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
  • /68

    $784,900

    • 4 Beds
    • 2.5 Baths
    • 3,177 Sq Ft

    402 Fair Hill Ct, Annapolis, MD 21403

    Welcome to this wonderfully updated and beautifully decorated home in sought-after Hunt Meadow! Ideally situated on a corner lot with a large yard, this cozy and inviting home offers the perfect blend of comfort, style, and location. One of the home’s standout features is the main-level primary bedroom, providing convenience and easy one-level living. With 4 bedrooms and 2½ baths, there is plenty

    Jack Papaleonti Academy Realty Inc.

    402 Fair Hill Ct, Annapolis, MD 21403
  • /3

    $96,000

    $46K PRICE INCREASE
    • Land
    • 10,018 Sq Ft
    • $417,391 per Acre

    3338 Arundel on The Bay Rd, Annapolis, MD 21403

    POST AUCTION! Make an offer, buy it now! 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 major traffic artery Forest Dr. This property is vacant.

    Adam Shpritz Ashland Auction Group LLC

    3338 Arundel on The Bay Rd, Annapolis, MD 21403
  • /47

    $1,285,000

    • 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
  • /51

    $769,900

    Open Sat 12PM - 2PM $229K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,156 Sq Ft

    278 Hillsmere Dr, Annapolis, MD 21403

    TIME TO MAKE YOUR MOVE!This is your chance to get into Hillsmere Shores, one of Annapolis’ most sought‑after waterfront communities. The exterior is deceiving — step inside to discover an unexpectedly open, bright, and airy interior that buyers don’t see every day.Sellers are highly motivated.If you’ve been waiting for the right Hillsmere home, this is it.The Hillsmere Shores

    Tommy Eicher Coldwell Banker Realty

    278 Hillsmere Dr, Annapolis, MD 21403
  • /46

    $2,685,000

    $295K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 5,082 Sq Ft

    3733 Thomas Point Rd, Annapolis, MD 21403

    Life takes on a different pace in Oakwood, where the calm waters of Fishing Creek and the South River provide an idyllic backdrop and effortless access to the Chesapeake Bay. With 93 feet of shoreline, a private pier with multiple slips, and a substantial 25,000-pound boat lift, this property is perfectly suited for boating enthusiasts and those who appreciate the beauty and tranquility of the

    Brad Kappel TTR Sotheby's International Realty

    3733 Thomas Point Rd, Annapolis, MD 21403
  • /24

    $309,900

    • 3 Beds
    • 2 Baths
    • 1,254 Sq Ft

    30 Sandstone Ct, Annapolis, MD 21403

    Welcome to this beautifully updated two level penthouse condo featuring three bedrooms, two full baths, and a thoughtfully designed open concept layout. The living and dining areas flow seamlessly together, while soaring ceilings and abundant natural light create a bright, spacious atmosphere. A cozy wood-burning fireplace adds warmth and charm. The elegant primary suite features a private en

    Arlene Harris Keller Williams Preferred Properties

    30 Sandstone Ct, Annapolis, MD 21403
  • /23

    $275,000

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    10 Sandstone Ct Unit K, Annapolis, MD 21403

    PRICE REDUCED FOR QUICK SALE! Back on the market with new photos! Welcome to this beautifully updated terrace-level condo offering the perfect blend of comfort and style. This 2-bedroom unit features fresh paint, brand-new carpet, and an upgraded kitchen complete with new countertops and stainless steel appliances. Enjoy easy single-level living with a spacious, open-concept layout that flows

    Sean Ussery CENTURY 21 New Millennium

    10 Sandstone Ct Unit K, Annapolis, MD 21403
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