Homes for Sale near Key School

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  /37

  $375,000

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft

  122 Roselawn Rd, Annapolis, MD 21403

  Welcome to 122 Roselawn Road, a beautifully renovated single-family home in the heart of Annapolis, MD. This 2-bedroom, 1-bathroom gem offers the perfect blend of modern upgrades and timeless charm. Step inside to discover fresh finishes and an open layout, making this home warm and inviting. Enjoy cooking in the gourmet kitchen featuring stainless steel appliances, ample cabinet space, and sleek

  

  Litra Simms

  Simms and Associates

  (410) 237-0887

  122 Roselawn Rd, Annapolis, MD 21403
• 

  

  

  /17

  $1,047,590 New Construction

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

  106 Stilly Way, Annapolis, MD 21403

  This stunning home, available for delivery in April, boasts high-end upgrades throughout. It features a first-floor owner's suite, plus three additional bedrooms on the second level, along with two full bathrooms and a spacious loft. The gourmet kitchen is a chef’s dream, complete with custom cabinetry and an open-concept design. The impressive two-story family room with soaring ceilings creates

  

  Terri Hill

  Builder Solutions Realty

  (443) 347-5495

  106 Stilly Way, Annapolis, MD 21403
• 

  

  

  /20

  $1,019,990 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,806 Sq Ft

  122 Stilly Way, Annapolis, MD 21403

  Photos are for illustration purposes. Agents must accompany buyer during first visit to the community.

  

  Terri Hill

  Builder Solutions Realty

  (443) 665-8307

  122 Stilly Way, Annapolis, MD 21403
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  /32

  $1,200,000

  • 4 Beds
  • 2.5 Baths
  • 2,322 Sq Ft

  160 Green St, Annapolis, MD 21401

  Step into a piece of Annapolis history with the Philip Clayton House, a cherished landmark dating back to 1834. Perfectly situated within walking distance to the City Dock, U.S. Naval Academy, and the vibrant shops and restaurants of Downtown Annapolis, this residence blends timeless character with everyday convenience. Over nearly two centuries, the home has undergone thoughtful renovations and

  Lucie Dulin Compass

  160 Green St, Annapolis, MD 21401
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  /2

  $850,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  316 Chester Ave, Annapolis, MD 21403

  Welcome to this beautiful home in the sought out neighborhood of Eastport. This home is charming with beautiful hardwood floors and spacious back yard - perfect for entertaining. Ready for the next home owner to make it their own! Great water views of Seashell Marina and Butlers Marina. For the love of nature and water views you will be right at home! Don't miss your chance to own in this highly

  Vita Makle Clark Realty Group, LLC

  316 Chester Ave, Annapolis, MD 21403
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  /86

  $589,000

  • 3 Beds
  • 5 Baths
  • 2,272 Sq Ft

  710 Agnes Dorsey Place, Annapolis, MD 21401

  Finally the Move in Ready 3 bedroom 3 full plus two half bath bright, spacious home with all the amenities and upgrades you have been waiting for! Prime Annapolis location! Bright Cheery, Spacious, fresh and ready for you! beautifully finished town home boasting oversized 2 car garage , gourmet open spacious kitchen with quartz countertops. Entertain or relax in the open kitchen, dining, living

  Susan Hartman O'Conor, Mooney & Fitzgerald

  710 Agnes Dorsey Place, Annapolis, MD 21401
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  /67

  $879,900

  • 5 Beds
  • 3.5 Baths
  • 2,818 Sq Ft

  3581 S River Terrace, Edgewater, MD 21037

  Stunningly Renovated Colonial in Sought-After Loch Haven. Welcome to this beautifully updated colonial, where no expense was spared in creating a perfect blend of modern elegance and timeless charm. Located in the highly desirable, amenity-rich community of Loch Haven, this home offers luxurious living both inside and out. From the moment you arrive, the inviting front porch with new Azek

  Colleen Smith EXP Realty, LLC

  3581 S River Terrace, Edgewater, MD 21037
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  /32

  $700,000

  • 2 Beds
  • 1.5 Baths
  • 988 Sq Ft

  24 Fleet St, Annapolis, MD 21401

  Welcome to 24 Fleet St—a beautifully maintained 2-bedroom, 1.5-bath row home nestled in the heart of historic downtown Annapolis. This classic home blends timeless character with modern comforts, featuring hardwood floors throughout, exposed brick accents, and a sunlit living space perfect for relaxing or entertaining. The updated kitchen includes stainless steel appliances, granite countertops,

  Shane Hall Compass

  24 Fleet St, Annapolis, MD 21401
• 

  

  /73

  $1,575,000

  • 4 Beds
  • 3.5 Baths
  • 4,887 Sq Ft

  3509 Monarch Dr, Edgewater, MD 21037

  Welcome to 3509 Monarch Drive, a private and pristine retreat nestled on a quiet street in South River Colony—Edgewater’s premier resort-style neighborhood with pools, tennis and pickleball courts, playgrounds, and access to the community golf course (separate membership).As you approach the stately brick-front exterior, the home’s curb appeal is immediately evident, surrounded by lush, manicured

  Kristen Boyer Berkshire Hathaway HomeServices PenFed Realty

  3509 Monarch Dr, Edgewater, MD 21037
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  /63

  $799,900 Open Sat 11AM - 1PM

  • 5 Beds
  • 4.5 Baths
  • 3,636 Sq Ft

  3325 Cedar Dr, Edgewater, MD 21037

  Room to Roam, Water to Wander – 5BR Beauty in Glebe Heights! Welcome to this perfectly positioned 5-bedroom, 4.5-bath home located in the sought after water-oriented community of Glebe Heights located on Glebe Bay just off the South River in Edgewater. Enjoy exclusive access (with just a small nominal fee) to the neighborhood pier, boat slips, beach, and fire pit, all just steps or a golf cart

  Dori Savani Douglas Realty, LLC

  3325 Cedar Dr, Edgewater, MD 21037
• 

  

  /35

  $619,900

  • 4 Beds
  • 3.5 Baths
  • 2,000 Sq Ft

  125 Lejeune Way, Annapolis, MD 21401

  Luxury Living in the Heart of Annapolis – Welcome to Admiral SquareTucked into the vibrant, highly desirable community of Admiral Square, this impeccably maintained 4-bedroom, 3.5-bath townhome offers the perfect blend of upscale comfort, modern convenience, and prime Annapolis living. Just minutes from the historic district, world-class restaurants, waterfront charm, and the Chesapeake Bay,

  Jason Donovan RE/MAX Leading Edge

  125 Lejeune Way, Annapolis, MD 21401
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  /30

  $975,000

  • 4 Beds
  • 2.5 Baths
  • 2,964 Sq Ft

  1206 Southwind Ct, Annapolis, MD 21403

  Welcome to this bright and beautiful 4-bedroom, 2.5-bath colonial tucked in the trees with timeless curb appeal and room to grow.From the moment you pull into the wide driveway and see the wraparound front porch, you'll feel right at home. Step inside to find freshly updated spaces filled with natural light—wood floors, neutral paint, and a welcoming layout that flows effortlessly from room to

  Chris Craddock EXP Realty, LLC

  1206 Southwind Ct, Annapolis, MD 21403
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  /64

  $850,000

  • 4 Beds
  • 3.5 Baths
  • 3,439 Sq Ft

  308 Mcdonough Rd, Annapolis, MD 21401

  OPEN HOUSE on May 3rd/4th from 11-1!Discover the charm of this true architectual gem, located in the sought after neighborhood of Admiral Heights. From intricate moldings, custom built ins, and original hardwood flooring, every detail tells a story. This mid century modern home stands out with its one-of-a-kind style and solid craftsmanship. This home features four generously sized bedrooms,

  Kevin Stodd EXP Realty, LLC

  308 Mcdonough Rd, Annapolis, MD 21401
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  /30

  $800,000 Open Sat 12:30PM - 2:30PM

  • 3 Beds
  • 4 Baths
  • 2,468 Sq Ft

  651 Genessee St, Annapolis, MD 21401

  Welcome to 651 Genesee Street — a rare find in the heart of Annapolis!This beautifully private property backs to serene woods on a spacious .45 acre lot, all while being just a short walk to the Naval Academy Stadium, West Annapolis, and downtown across the Rowe Blvd bridge. Enjoy the best of both worlds: peaceful seclusion with city conveniences just steps away.The home is move-in ready and

  Justin Disborough Samson Properties

  651 Genessee St, Annapolis, MD 21401
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  /20

  $550,000

  • 1 Bed
  • 1 Bath
  • 768 Sq Ft

  316 Burnside St Unit 208, Annapolis, MD 21403

  Welcome to 316 Burnside Street, Unit #208 — a charming one-bedroom, one-bath condominium nestled in the heart of Annapolis. This inviting residence features beautiful luxury vinyl plank flooring, a recently installed water heater (2024), and central A/C for year-round comfort. This flexible layout offers additional sleeping accommodations with a Murphy bed in the dining area and a sleeper sofa.

  Bob Chew Berkshire Hathaway HomeServices PenFed Realty

  316 Burnside St Unit 208, Annapolis, MD 21403
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  /52

  $805,000

  • 4 Beds
  • 3.5 Baths
  • 2,780 Sq Ft

  3106 Riverwalk Ct, Annapolis, MD 21403

  Tucked away on a peaceful cul-de-sac in the highly sought after Blackwalnut Cove neighborhood, this beautifully updated home offers over 3,000 square feet of stylish and functional living space. Backing up to the serene Peninsula Park, enjoy a spacious backyard perfect for outdoor living and entertaining – all just a short stroll to the highly-rated (5-star!) Hillsmere Elementary School.Step

  Markus Smith Samson Properties

  3106 Riverwalk Ct, Annapolis, MD 21403
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  /103

  $975,000

  • 4 Beds
  • 4.5 Baths
  • 4,494 Sq Ft

  709 Pilot House Dr, Annapolis, MD 21401

  A former model home in Kingsport! Step into an inviting two story foyer that sets the tone for the entire residence! This home offers a blend of elegance and functionality. Many updates have been done by current homeowners. A three story, three-sided brick home on a corner lot that emanates timeless elegance. This home has two inviting front porches for relaxation. Entering the two story

  Anne Tkacik Long & Foster Real Estate, Inc.

  709 Pilot House Dr, Annapolis, MD 21401
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  /38

  $545,000

  • 3 Beds
  • 3.5 Baths
  • 2,202 Sq Ft

  167 Spring Place Way, Annapolis, MD 21401

  Beautifully-maintained home in the Riva Trace (Spring Place) community. Enjoy a spacious main floor layout with kitchen that connects to open living and dining areas. Step out onto a cozy deck with views of trees, perfect for grilling and relaxation. Upper floor has spacious primary bedroom with walk-in closet and ensuite bathroom with soaking tub and separate shower. Two other bedrooms share a

  Grace Belkot RE/MAX Advantage Realty

  167 Spring Place Way, Annapolis, MD 21401
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  /93

  $1,100,000

  • 5 Beds
  • 5 Baths
  • 4,432 Sq Ft

  3310 Leritz Ln, Edgewater, MD 21037

  Spacious, stylish and luxurious colonial in sought after Turnbull Estates on Glebe Bay. VA assumable loan at 5.125%! This 5 bedroom, 3 FB, 2 HB home offers over 5000 finished SF! The heart of the home - the fully redesigned kitchen - boasts white cabinets, sleek quartz countertops, a quaint breakfast bar, an island, a deep sink, induction cooktop, double convection oven/microwave combo,

  Tracey McCallum Chaney Homes, LLC

  3310 Leritz Ln, Edgewater, MD 21037
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  /33

  $475,000

  • 3 Beds
  • 2.5 Baths
  • 1,775 Sq Ft

  2119 Hideaway Ct Unit 48, Annapolis, MD 21401

  Luxury Living in the Heart of Annapolis – Creekside Cove EleganceWelcome to Creekside Cove—a serene, tree-lined alcove community tucked into the heart of Annapolis, the unofficial sailing capital of the world. With its charming historic downtown, vibrant restaurants, boutique shopping, waterfront festivals, and proximity to both D.C. and Baltimore, this location offers the perfect balance of

  Jason Donovan RE/MAX Leading Edge

  2119 Hideaway Ct Unit 48, Annapolis, MD 21401
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  /57

  $995,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  1080 Mayo Rd, Edgewater, MD 21037

  STUNNING WATERFRONT VIEWS - EXCEPTIONAL LOT & SCREENED-IN PORCH - THE ULTIMATE LUXURY RETREAT! Welcome to 1080 Mayo Rd; a beautifully updated cottage on Ramsey Bay, offering 54 feet of water frontage, a gorgeously landscaped private yard, and the screened-in porch with eastern exposure that you’ve been dreaming of. This property is a haven for boaters, anglers, and outdoor enthusiasts alike;

  Rick Cantore RE/MAX Advantage Realty

  1080 Mayo Rd, Edgewater, MD 21037
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  /56

  $800,000

  • 4 Beds
  • 3 Baths
  • 2,752 Sq Ft

  2651 Ogleton Rd, Annapolis, MD 21403

  Welcome to 2651 Ogleton Road — where lifestyle meets location!Nestled in the sought-after waterfront community of Annapolis Roads, this beautifully updated 4-bedroom, 3-bath home offers nearly 3,000 square feet of living space, sitting gracefully atop a lush and private .62-acre lot. The home is surrounded by mature trees and professionally landscaped gardens — and the fully fenced backyard with

  Sandra K. Libby Long & Foster Real Estate, Inc.

  2651 Ogleton Rd, Annapolis, MD 21403
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  /28

  $524,990

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

  2040 Puritan Terrace, Annapolis, MD 21401

  Beautiful end unit townhome in a highly desirable location just outside downtown Annapolis with easy access to Rt. 50. This home boasts hardwood flooring throughout with large bay windows offering plenty of natural light. The main level has a spacious family room, powder room, dining area, deck access as well as a gourmet kitchen. This luxurious kitchen offers granite countertops, a large

  Travis Mahaffey Anne Arundel Properties, Inc.

  2040 Puritan Terrace, Annapolis, MD 21401
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  /33

  $1,100,000 Open House 5/18

  • 4 Beds
  • 3.5 Baths
  • 3,148 Sq Ft

  711 Genessee St, Annapolis, MD 21401

  Welcome to 711 Genessee Street – where modern luxury meets the heart of Annapolis charm. Located in the coveted West Annapolis School District, this newer construction stunner (built in 2021) offers the perfect blend of upscale finishes, smart design, and unbeatable location—all within walking distance to shops, dining, and everything you love about Annapolis living.Step inside to find a main

  Michelle Triolo Compass

  711 Genessee St, Annapolis, MD 21401
• 

  

  /35

  $950,000

  • 2 Beds
  • 2 Baths
  • 990 Sq Ft

  3904 Dogwood Trail, Edgewater, MD 21037

  Spectacular .45 acre waterfront gem just off the South River in the sought after Shoreham Beach community! Arrive by car or by boat, and enjoy the private dock for boating, fishing, crabbing, viewing the AMAZING sunsets and seasonal fireworks displays. Huge lot with endless possibilities at this premier waterfront property! Enter the front of the home on the waterfront side into the sunroom

  Missy Raffa RE/MAX Realty Group

  3904 Dogwood Trail, Edgewater, MD 21037
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  /74

  $976,000

  • 3 Beds
  • 3 Baths
  • 2,060 Sq Ft

  704 Severn Ave, Annapolis, MD 21403

  Welcome to 704 Severn Avenue, a beautifully maintained Cape Cod three-bedroom, three-full-bath home in the heart of Eastport. An ornamental cherry tree, 10-year-old annual lantana, lilacs, azaleas, tulips, and more are absolutely beautiful and blooming throughout the year. Entering the home you are greeted with a wooden staircase leading to the upstairs bedrooms, to the right is the perfect

  Sarah Luisi Keller Williams Flagship

  704 Severn Ave, Annapolis, MD 21403
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  /38

  $985,000

  • 4 Beds
  • 2.5 Baths
  • 2,176 Sq Ft

  1141 Mainsail Dr, Annapolis, MD 21403

  Welcome to 1141 Mainsail Drive, a renovated Classic Colonial style home located in the sought-after Waterfront Community of Anchorage. This 4-bedroom, 2.5-bathroom property has undergone over $200,000 in renovations over the past 20 years while preserving its classic colonial charm. This beautiful corner lot has a newly repaved driveway, a 2-car garage and is only a block away from the

  Ani Gonzalez-Brunet Coldwell Banker Realty

  1141 Mainsail Dr, Annapolis, MD 21403
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  /43

  $874,000

  • 3 Beds
  • 2 Baths
  • 1,388 Sq Ft

  503 Burnside St, Annapolis, MD 21403

  Charming Eastport Bungalow in Prime Location!You can’t beat the location of this well maintained Eastport bungalow—lovingly cared for by the same family for over 85 years! Nestled in one of Annapolis's most sought-after neighborhoods, this home blends classic character with modern updates. Start your day on the welcoming screened front porch, the perfect spot for morning coffee. Inside, the home

  Georgie Berkinshaw Coldwell Banker Realty

  503 Burnside St, Annapolis, MD 21403
• 

  

  /37

  $369,000

  • 2 Beds
  • 2 Baths
  • 1,543 Sq Ft

  410 Hamlet Club Dr Unit 305, Edgewater, MD 21037

  Welcome to your dream home in the heart of the vibrant 55+ community of The Hamlets at South River Colony! This stunning 2-bedroom, 2-bathroom condo, located at 410 Hamlet Club Dr, Edgewater, MD 21037, offers the perfect blend of modern comfort and low-maintenance living. Spanning approximately 1,550 sq. ft., this bright and airy residence boasts an open floor plan with 9-foot ceilings, cleaned

  Brian Graham Engel & Völkers Annapolis

  410 Hamlet Club Dr Unit 305, Edgewater, MD 21037
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  /126

  $4,650,000

  • 6 Beds
  • 9 Baths
  • 12,374 Sq Ft

  840 Childs Point Rd, Annapolis, MD 21401

  One-of-a-kind Waterfront Luxury in Annapolis, Maryland! Secluded on 2.59 lush, park-like acres along the shores of one of the Chesapeake Bay’s most serene and protected tributaries, this exceptional estate offers an unparalleled blend of privacy, elegance, and premier waterfront living rarely found in Annapolis. From the moment you arrive down the tree-lined drive, a sense of calm and

  David Orso Berkshire Hathaway HomeServices PenFed Realty

  840 Childs Point Rd, Annapolis, MD 21401
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  /87

  $2,600,000

  • 4 Beds
  • 4.5 Baths
  • 3,470 Sq Ft

  1011 Dulaney Ln, Annapolis, MD 21403

  Introducing a coastal gem with artistic touches… Nestled by the waterfront, this property offers a luxurious blend of functional design and artisan craftsmanship. With approximately 2,000 sq. ft. of Timbertek decking, relax on the master bedroom's private balcony with soft down-lighting or lounge on the carefully crafted deck seating under the bow window's gentle glow. Walk along durable brick

  Shane Hall Compass

  1011 Dulaney Ln, Annapolis, MD 21403
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  /32

  $875,000 Open Thu 4:30PM - 6:30PM

  • Land
  • 0.49 Acre
  • $1,785,714 per Acre

  1411 West St, Annapolis, MD 21401

  Located just across from the Annapolis Library and minutes from the heart of downtown, this 1940s home blends preserved historic charm with prime land potential. Set on a large, flat lot, it offers original refinished pine floors, arched entryways, solid wood doors, and built-in features that speak to a level of craftsmanship rarely found today.The main level includes two bedrooms and a full

  Kara Chaffin Donofrio Long & Foster Real Estate, Inc.

  1411 West St, Annapolis, MD 21401
• 

  

  /23

  $565,000

  • 4 Beds
  • 2 Baths
  • 1,826 Sq Ft

  1019 Timber Creek Dr, Annapolis, MD 21403

  Welcome to 1019 Timber Creek Drive—an updated 4-bedroom, 2-bath home nestled in a quiet, tree-lined Annapolis neighborhood just minutes from downtown and Eastport. Inside, you’ll find fresh paint, new kitchen, new flooring, new carpet, and a bright layout featuring hardwood floors, a cozy wood-burning fireplace, and newly renovated bathrooms. The kitchen offers modern appliances and plenty of

  Shane Hall Compass

  1019 Timber Creek Dr, Annapolis, MD 21403
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  /38

  $975,000 Open Fri 4PM - 7PM

  • 3 Beds
  • 3.5 Baths
  • 2,080 Sq Ft

  227 West St, Annapolis, MD 21401

  Welcome to 227 West Street: where historic charm meets modern elegance in the thriving Murray Hill neighborhood. This upscale townhome offers a rare opportunity to own a beautifully designed residence in one of the most walkable, culturally rich neighborhoods in the city.Thoughtfully built in 2013 by Bozzuto, this 3-bedroom, 3.5-bath home blends contemporary comfort with timeless appeal. Step

  Jen Denney EXP Realty, LLC

  227 West St, Annapolis, MD 21401
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  /29

  $524,900 Open Sat 2PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 1,581 Sq Ft

  801 Selby Blvd, Edgewater, MD 21037

  Beautiful house a great value. community waterfront stunning views park includes basketballl court , play equipment community center/

  Michele Nwuli Keller Williams Flagship

  801 Selby Blvd, Edgewater, MD 21037
• 

  

  /25

  $5,000

  • 4 Beds
  • 2 Baths
  • 1,932 Sq Ft

  3730 Thomas Point Rd, Annapolis, MD 21403

  Waterfront home in Oakwood Community w/ unsurpassed views of S. River and Bay. Newly renovated gourmet kitchen w/ island. Main level 2 BR 1 bath. Spacious open living area, F/R with wood-burning F/P. Hard wood FL through out. 2-Car garage w/ lots of workspace and storage. New 100 foot pier. Tranquil location, steps from Thomas Point Park. Pets case-by-case.

  Amiram Levi Realty Advantage of Maryland LLC

  3730 Thomas Point Rd, Annapolis, MD 21403
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  /43

  $4,995,000

  • 4 Beds
  • 4.5 Baths
  • 3,250 Sq Ft

  54 River Dr, Annapolis, MD 21403

  Gorgeous coastal style home in the coveted Bay Ridge community with stunning and thoughtful renovations that highlight the expansive Chesapeake and Bay Bridge views! The extensive renovation by M Homes elevated the appeal and functionality of the home by adding 2 additional ensuite bedrooms and laundry room on the 2nd level and much more. No expense was spared to make this a home of distinction,

  Brad Kappel TTR Sotheby's International Realty

  54 River Dr, Annapolis, MD 21403
• 

  

  /22

  $2,390,000

  • Land
  • 0.22 Acre
  • $10,863,636 per Acre

  48 E Lake Dr, Annapolis, MD 21403

  Once-in-a-Lifetime Opportunity to Build Your Dream Waterfront Home in Bay Ridge. Don't miss your chance to own the last remaining waterfront lot in the prestigious and highly sought-after Bay Ridge community. This is a rare opportunity to design and build your dream home on a premium lot offering 57 feet of serene waterfront on protected Lake Ogleton. Enjoy breathtaking, unobstructed views and

  Colleen Smith EXP Realty, LLC

  48 E Lake Dr, Annapolis, MD 21403
• 

  

  /12

  $449,900

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  1643 Oldtown Rd, Edgewater, MD 21037

  Professional Photos Coming! Recently renovated and move-in ready, one-story home situated on an oversized level lot, and just steps away from one of the community beaches, and waterfront! All major items have been taken care of. A brand-new HVAC system was installed in April of 2025, the attic was insulated in January of 2025, crawl space was encapsulated in January 2025, new water softener

  Judy Lemme Long & Foster Real Estate, Inc.

  1643 Oldtown Rd, Edgewater, MD 21037
• 

  

  /7

  $415,000

  • 4 Beds
  • 1 Bath
  • 1,180 Sq Ft

  202 Lakeview Ave, Edgewater, MD 21037

  Charming cottage nestled in the peaceful water-privileged community of Beverly Beach (which is a special tax district with a minimal fee of $50.00 Yr!). Beverly Beach offers beautiful walking trails and even a neighborhood beach on the Chesapeake Bay! Full of character and warmth, this 4-bedroom, 1-bathroom home provides the perfect blend of cozy charm and relaxed coastal living, with a bright,

  Kelly Kindig Douglas Realty, LLC

  202 Lakeview Ave, Edgewater, MD 21037

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