Homes for Sale near Windy Hill Middle School

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  /56

  $600,000

  • 3 Beds
  • 3 Baths
  • 2,757 Sq Ft

  8205 F St, Chesapeake Beach, MD 20732

  This is no cookie-cutter home! Welcome to 8205 F Street — a rare Acorn Deck House in Chesapeake Beach, designed to celebrate light, warmth, and natural materials. Known for their signature post-and-beam construction, soaring ceilings, and walls of glass, Acorn Deck Houses are architectural icons that blur the line between indoors and out — and this one delivers that feeling in full. Expansive,

  

  Angelica Dennis

  Keller Williams Capital Properties

  (410) 220-4311

  8205 F St, Chesapeake Beach, MD 20732
• 

  Explore Windy Hill Middle School

• 

  

  

  /40

  $500,000

  • 4 Beds
  • 3 Baths
  • 1,776 Sq Ft

  8815 Falling Leaf Dr, Owings, MD 20736

  Discover the perfect blend of privacy and modern comfort in this stunning home, completely renovated to the studs. Nestled down a private driveway on over 3.5 acres, this property offers both tranquility and style. The main level features three spacious bedrooms, including a serene primary suite with a spa-inspired ensuite bath. Two additional bedrooms share a beautifully updated full bathroom.

  Dorothy Bistransin Redfin Corp

  8815 Falling Leaf Dr, Owings, MD 20736
• 

  

  

  /40

  $575,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 2,151 Sq Ft

  9101 Greenwood Ave, North Beach, MD 20714

  Situated on three lots within town limits. With beach access, town water and sewer. All one level living with new HVAC, new windows and door, remodeled bathrooms, new floors, new paint throughout. Stainless steel appliances. Large primary with ensuite, and cedar closet. Separate room with own entrance to be used as possible office. Large expansive living room with bar and full brick propane

  Erica Baker TTR Sotheby's International Realty

  9101 Greenwood Ave, North Beach, MD 20714
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  /35

  $749,000

  • 4 Beds
  • 3.5 Baths
  • 2,520 Sq Ft

  8240 Harrison Blvd, Chesapeake Beach, MD 20732

  WELCOME HOME!Nestled in the desirable Richfield Station community, this stunning colonial home boasts a blend of elegance and comfort, perfect for family living and entertaining. With four spacious bedrooms and three and a half baths, this residence offers ample space for everyone.Step inside to find a welcoming living room that seamlessly flows into a separate dining area, ideal for

  Chrystal Dove CENTURY 21 New Millennium

  8240 Harrison Blvd, Chesapeake Beach, MD 20732
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  /52

  $769,000

  • 5 Beds
  • 4.5 Baths
  • 3,740 Sq Ft

  215 Hoile Ln, Huntingtown, MD 20639

  Nestled in the serene Twin Lakes community, this charming 3,700+ sq. ft. home blends comfort, style, and timeless appeal. The classic brick exterior, extensive hardscaping, and inviting outdoor living spaces make it perfect for both relaxation and entertaining. Enjoy summer barbecues on the deck or unwind on the porch, surrounded by nature on a peaceful 2.31-acre lot.Roof was replaced

  ANEHRU HAMADU Long & Foster Real Estate, Inc.

  215 Hoile Ln, Huntingtown, MD 20639
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  /54

  $604,990

  • 4 Beds
  • 2.5 Baths
  • 3,070 Sq Ft

  140 Hoile Ln, Huntingtown, MD 20639

  Step into timeless elegance and thoughtful design with this custom-built all-brick colonial, perfectly situated on over an acre of land in the prestigious Twin Lakes community—known for its premier homes and sought-after school district. At the heart of the home is an upgraded kitchen that combines function and style. It features Corian countertops, stainless steel appliances, deep double sink,

  Frank McKnew RE/MAX Realty Group

  140 Hoile Ln, Huntingtown, MD 20639
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  /43

  $725,000

  • 5 Beds
  • 3.5 Baths
  • 3,626 Sq Ft

  56 Cross Point Dr, Owings, MD 20736

  This one has a ASSUMABLE VA LOAN available at 2.25% interest rate! THATS A HUGE SAVINGS ON YOUR MONTHLY PAYMENT!! IF PURCHASING A HOME THAT IS TRULY MOVE-IN READY, peace of mind that you won’t move in and have to start doing a bunch of repairs is on your list, THIS ONE CHECK ALL OF THE BOXES!! The owners have done all of the updating on this one so you can have peace of mind in your new home! New

  Tracey Bellotte Coldwell Banker Realty

  56 Cross Point Dr, Owings, MD 20736
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  /59

  $689,900

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  9642 Boyds Turn Rd, Owings, MD 20736

  Renovated Farmhouse on near 11 Acres Move right in to this beautifully updated 4BR/2BA farmhouse featuring a first-floor owner’s suite, spacious living areas, and thoughtful upgrades throughout—including a new roof, siding, and HVAC. Set on 10.95 scenic acres with community pond access, the property offers privacy and wide-open country living just minutes from local shops and an easy commute to

  Adam Boerckel RE/MAX One

  9642 Boyds Turn Rd, Owings, MD 20736
• 

  /2

  $550,000 Coming Soon

  • 5 Beds
  • 4.5 Baths
  • 2,883 Sq Ft

  331 C Jones Rd, Sunderland, MD 20689

  Tucked away on a picturesque lot in Northern Calvert County, this home has so much to offer. The main level of the home includes an open floor plan, eat-in kitchen, dining room, and a bonus room perfect for an office or formal living room. Also included on the main level is a large primary bedroom and bathroom with a walk-in shower. On the second floor, there are TWO additional primary bedrooms

  Dawn Riley RE/MAX One

  331 C Jones Rd, Sunderland, MD 20689
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  /30

  $355,000

  • 3 Beds
  • 2.5 Baths

  2330 Forest Ridge Terrace, Chesapeake Beach, MD 20732

  Welcome Home!This beautifully maintained 3-bedroom, 2.5-bath townhouse offers comfort, convenience, and style in one of the area’s most desirable, family-friendly communities. Featuring brand new carpet and fresh paint throughout, this home is move-in ready and waiting for you!Enjoy a spacious one-car garage, open living and dining area, and a well-equipped kitchen on the main level.

  Tresha Davis Coldwell Banker Realty

  2330 Forest Ridge Terrace, Chesapeake Beach, MD 20732
• 

  

  /17

  $500,000

  • 4 Beds
  • 3 Baths
  • 1,864 Sq Ft

  3420 Mary Lou Ln, Chesapeake Beach, MD 20732

  Set in the heart of Northern Calvert County, this delightful home offers a peaceful escape surrounded by nature while keeping you close to all the best of the Chesapeake Bay lifestyle. Beaches, boardwalks, marinas, local dining, shopping, and scenic trails are just minutes away, yet the property feels like your own private hideaway. Step onto the charming front porch, added just four years ago,

  Sarah Reynolds Keller Williams Realty

  3420 Mary Lou Ln, Chesapeake Beach, MD 20732
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  /102

  $849,500 Open Sun 1PM - 3PM

  • 4 Beds
  • 5 Baths
  • 3,049 Sq Ft

  8074 Windward Key Dr, Chesapeake Beach, MD 20732

  Welcome to 8074 Windward Key Drive – a stunning four-level coastal townhome offering sweeping double sided water views, stylish updates, and exceptional outdoor living on every floor! Perfectly situated in the sought-after Windward Key community, this residence delivers the best of Chesapeake Bay living with resort-style amenities and thoughtful modern design throughout. Step inside to a bright,

  Pattee McInerney Scott McInerney RE/MAX One

  8074 Windward Key Dr, Chesapeake Beach, MD 20732
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  /49

  $419,000

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  2905 Galway Ln, Chesapeake Beach, MD 20732

  This is a GREAT value in the sought after neighborhood of The Highlands. Home had a Kitchen Remodel and New Floors and Bathroom in 2023 * New Roof 2013 * Good Sized yard goes BEYOND the fence back to the trees. This is a Single Family home at a townhome price! Finished Lower Level offers a 2nd Family room area and a space that could be a 4th BR/Gym/Office/Den - whatever you wish! Enjoy all the

  Lara Owings RE/MAX Realty Group

  2905 Galway Ln, Chesapeake Beach, MD 20732
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  /31

  $400,000

  • 4 Beds
  • 3 Baths
  • 1,894 Sq Ft

  4012 10th St, North Beach, MD 20714

  Welcome to 4012 10th Street, just a half mile from beach access at no cost! Located right in the heart of charming North Beach — a wonderful opportunity to own a comfortable, well-positioned home in the “Jewel of the Chesapeake Bay”. This 4 bedroom 3 full bath single-family home built in 1998, was designed thoughtfully by the Original Owners with an efficient footprint for open space and today's

  Joseph McDonnell Corner House Realty

  4012 10th St, North Beach, MD 20714
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  /35

  $299,999

  • 2 Beds
  • 1 Bath
  • 719 Sq Ft

  6122 6th St, Chesapeake Beach, MD 20732

  Welcome to charming 6122 6th St, nestled within the Chesapeake Beach community. This home is back on the market with a new well, new roof, covered outdoor living area, separate fenced in yard, and overall refresh. This cozy home features two bedrooms, a remolded bathroom, and a spacious kitchen with lots of storage and brand-new appliances. The open floor plan allows unlimited opportunities for

  Tiffany Oliver RE/MAX One

  6122 6th St, Chesapeake Beach, MD 20732
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  /3

  $89,000

  • Land
  • 0.15 Acre
  • $593,333 per Acre

  8922 Louisville Ave, North Beach, MD 20714

  BUILD BY THE BAY. The lovely resort town of North Chesapeake Beach has so much to offer. Easy commute to major destinations and AFB. Please check out the websites for North Beach and Chesapeake Beach. Level lot just 7 Blocks to the Boardwalk/Bay. Owner/agent

  Robyn Day RE/MAX One

  8922 Louisville Ave, North Beach, MD 20714
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  /2

  $99,000

  • Land
  • 1.2 Acres
  • $82,500 per Acre

  0 10th St, Chesapeake Beach, MD 20732

  Great opportunity in Chesapeake Beach — less than an hour from Washington, DC! Vacant 1.2-acre lot conveniently located near restaurants, marinas, and the beach. Buyer must verify all zoning, utility, and building requirements. Lot includes wetland area and may require additional approvals prior to construction.Property sold AS-IS. Buyer is fully responsible for all due diligence regarding

  Cristhian Huamani Tia Realty. LLC

  0 10th St, Chesapeake Beach, MD 20732
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  /30

  $499,900

  • 5 Beds
  • 3 Baths
  • 1,872 Sq Ft

  3813 8th St, North Beach, MD 20714

  ***LOAN ASSUMPTION- AWESOME 2.625%!!** Stunning 5-Bedroom Home with In-Law Suite or Airbnb Income Potential! Welcome to this beautifully updated 5-bedroom, 3 full bathroom home offering flexible living spaces, modern upgrades, and exceptional potential for rental income. The optional in-law suite, media room, or play area make it ideal for multi-generational living or entertaining. The current

  Heather Hall Hyatt & Company Real Estate LLC

  3813 8th St, North Beach, MD 20714
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  /15

  $309,900

  • 2 Beds
  • 1 Bath
  • 798 Sq Ft

  3932 6th St, North Beach, MD 20714

  Seller offering 3% toward buyer’s closing costs with a full-price offer. Welcome to 3932 6th Street, located in North Beach! This beautifully REFRESHED 2-bedroom, 1 bath home sits just 4 blocks from the Chesapeake Bay in the heart of North Beach! Freshly painted and newly carpeted bedrooms, it's move-in ready for you to start enjoying the laid-back lifestyle North Beach has to offer. The best

  Heather Grierson CENTURY 21 New Millennium

  3932 6th St, North Beach, MD 20714
• 

  

  /27

  $475,000

  • 3 Beds
  • 4 Baths
  • 2,206 Sq Ft

  8910 Louisville Ave, North Beach, MD 20714

  The seller's have relocated the home waits for you! Enjoy the privacy your home offers with all the charm the Twin Beaches has to offer. This three level colonial sits at the end of a quiet street. As you enter the main level of the home there is an office to the right and a half bath across from the office. The kitchen has a huge pantry which opens up to the dining area. You can walk out

  Beth Carroll Hutchins Properties

  8910 Louisville Ave, North Beach, MD 20714
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  /53

  $499,000

  • 4 Beds
  • 3.5 Baths
  • 3,286 Sq Ft

  3761 Bedford Dr, North Beach, MD 20714

  Welcome to 3761 Bedford Dr, a rare and expansive 4-level end-unit townhome in the desirable San Francisco by the Bay community of North Beach, MD. Backing to a peaceful wooded area, this home offers the perfect mix of luxury, privacy, and low-maintenance living. Inside, you'll find hardwood floors throughout the main level and upper floors—including the entire fourth-level primary suite, which

  Dawn Riley RE/MAX One

  3761 Bedford Dr, North Beach, MD 20714
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  /64

  $849,950 Open Sun 12:30PM - 2:30PM

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  9000 Bay Ave Unit 401 & 402, North Beach, MD 20714

  Welcome to this stunning, one-of-a-kind penthouse condo, offering unparalleled views of the Chesapeake Bay and the beach. Located in the coveted town of North Beach , this unique home combines two original units (401 & 402), creating a vast and luxurious living space that truly showcases the best of waterfront living. As you step through the front door, you’re greeted by breathtaking views

  Pattee McInerney Scott McInerney RE/MAX One

  9000 Bay Ave Unit 401 & 402, North Beach, MD 20714
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  /33

  $385,000

  • 2 Beds
  • 2 Baths
  • 792 Sq Ft

  3936 5th St, North Beach, MD 20714

  Welcome to coastal living at its finest! This beautifully maintained 2-bedroom, 2-bathroom home is perfectly located just moments from the beach and the boardwalk, offering the ideal blend of relaxation, convenience, and Chesapeake Bay charm.Enjoy your morning coffee or evening breeze on the spacious deck, with room for outdoor dining and seasonal décor. The property also offers a fenced

  Bonnie O'Donnell RE/MAX One

  3936 5th St, North Beach, MD 20714
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  /85

  $1,650,000

  • 6 Beds
  • 4.5 Baths
  • 3,387 Sq Ft

  9318 Atlantic Ave, North Beach, MD 20714

  Perched on three expansive lots with prime frontage, this North Beach home offers breathtaking water views from nearly every window and multiple decks overlooking the Chesapeake Bay. Refinished hardwood floors in a light tone with both warm and cool graining complement the freshly painted interiors, while design-inspired tile and finishes elevate every renovated bathroom. Modern updates include

  Kristi Neidhardt Northrop Realty

  9318 Atlantic Ave, North Beach, MD 20714
• 

  

  /71

  $498,500

  • 3 Beds
  • 2 Baths
  • 2,283 Sq Ft

  3709 29th St, Chesapeake Beach, MD 20732

  **OWNER SAYS BRING ALL OFFERS!!**Welcome to your Chesapeake Bay retreat—where comfort, style, and location come together beautifully. Just minutes from the water, with seasonal water views, arrive to this home's front door on the expansive front patio! This pristine, recently remodeled home offers a light-filled, open-concept layout that’s truly turn-key. Step inside to discover gleaming

  Sam Barbieri RE/MAX United Real Estate

  3709 29th St, Chesapeake Beach, MD 20732
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  /18

  $379,900

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  6245 3rd St, Chesapeake Beach, MD 20732

  Beautifully maintained 3-bedroom, 2-bath rambler nestled on a private corner lot. Step inside to find an open and inviting layout featuring LVP flooring throughout, offering both style and durability. The heart of the home is the bright white kitchen, perfect for cooking and entertaining with its clean design and functional layout. Spacious primary suite includes a full en-suite bath, while two

  Jordon DeGennaro O'Brien Realty ERA Powered

  6245 3rd St, Chesapeake Beach, MD 20732
• 

  

  /39

  $499,000

  • 3 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  3757 Bedford Dr, North Beach, MD 20714

  This rare four story end unit townhome showcases effortless indoor-outdoor living, has oversized double decks with views of the estuary and a large finished basement. The main level flows into outdoor spaces ideal for relaxing or hosting, while three comfortable bedrooms, all with walk in closets, provide ample private space. The extra light from the end unit windows brightens up the entire home.

  Stephanie Glaubitz Home Towne Real Estate

  3757 Bedford Dr, North Beach, MD 20714
• 

  /2

  $24,999

  • Land
  • 1.09 Acres
  • $22,935 per Acre

  3664 Brookeside Dr, Chesapeake Beach, MD 20732

  Vacant Lot 1.09 acres in Existing Neighborhood. Great Value! Build your dream home. Perc eval completed in April 2023. Fantastic location in Chesapeake Beach!

  Daniel Lusk McWilliams/Ballard Inc.

  3664 Brookeside Dr, Chesapeake Beach, MD 20732
• 

  

  /39

  $600,000

  • 4 Beds
  • 3.5 Baths
  • 2,370 Sq Ft

  2050 Horace Ward Rd, Owings, MD 20736

  NEW PRICE for Your Own Private Oasis in Northern Calvert County!Welcome to 2050 Horace Ward Rd—where comfort, space, and location come together in perfect harmony! Nestled on two beautiful, usable acres with NO HOA, this charming home offers the freedom to live and play your way. Enjoy the inviting front porch, newly stained expansive back deck, fresh exterior light fixtures, updated

  Joan Stansfield Samson Properties

  2050 Horace Ward Rd, Owings, MD 20736
• 

  

  /32

  $484,000

  • 4 Beds
  • 2.5 Baths
  • 2,012 Sq Ft

  3600 4th St, North Beach, MD 20714

  Fully updated in 2025, this 4-bedroom, 2.5-bath home is move-in ready and designed for modern family living. Major updates include a new roof, siding, 6” gutters, gutter guards, windows, doors and Trex decking on the front and back. Inside, enjoy fresh paint, new luxury vinyl wide plank flooring on the main level, new carpet, and updated interior doors.The kitchen has been completely

  Michelle Faig CENTURY 21 New Millennium

  3600 4th St, North Beach, MD 20714
• 

  

  /30

  $675,000

  • 4 Beds
  • 3.5 Baths
  • 3,180 Sq Ft

  2425 Woodland Ct, Chesapeake Beach, MD 20732

  Richfield Station (upgrades ongoing - see new pics!) 3200 sq. ft. home located in the small municipal Town of Chesapeake Beach. Woodland Court is a conveniently located cul-de-sac in Northern Calvert County. Local services include weekly trash/recycle/bulk pick up and snow clearing by the Town. First floor formal dining with bay window, hardwood flooring, spacious family room with custom

  Pamela Debnam Houwzer, LLC

  2425 Woodland Ct, Chesapeake Beach, MD 20732
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  /34

  $499,900

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

  3719 3rd St, North Beach, MD 20714

  The appraisal came in at list price, but the buyer decided to back out.Charming Rancher in the Heart of North Beach – “The Jewel of the Chesapeake Bay”Welcome to your coastal retreat in the picturesque waterfront town of North Beach, Maryland—renowned for its scenic boardwalk, sandy beach, and vibrant, small-town charm. Nestled just blocks from the bay, this beautifully landscaped

  Jason Donovan RE/MAX Leading Edge

  3719 3rd St, North Beach, MD 20714
• 

  

  /15

  $699,000

  • 4 Beds
  • 2 Baths
  • 1,682 Sq Ft

  4006 1st St, North Beach, MD 20714

  Situated on one lot, the property also includes two separately deeded building lots, with the potential for a third buildable lot pending additional engineering - ideal for developers, investors, or those seeking a family compound .Nestled just a few blocks from the boardwalk, sandy beach and local restaurants, this spacious Cape Cod offers charm and opportunity. The home features 4 bedrooms and

  Laura Peruzzi RE/MAX One

  4006 1st St, North Beach, MD 20714
• 

  

  /12

  $589,000

  • Land
  • 2.07 Acres
  • $284,541 per Acre

  125 Prospect Dr, Sunderland, MD 20689

  2+ ACRE COMMERCIAL PROPERTY LOCATED PROMINENTLY ALONG THE ROUTE 2/4 SPLIT IN CALVERT COUNTY, MD! OWNER FINANCING AVAILABLE!!!! This is a PRIME LOCATION - among an existing industrial hub, adjacent to well-established businesses including Morgan E. Russell, Walton's Welding, Fabrication, and Scheibel Construction. This property is zoned for commercial light industrial which is ideal for businesses

  Sherri Verdon RE/MAX One

  125 Prospect Dr, Sunderland, MD 20689
• 

  

  /14

  $199,000

  • Land
  • 5.37 Acres
  • $37,058 per Acre

  6852 Old Bayside Rd, Chesapeake Beach, MD 20732

  LOT IS ACCESSED AT END OF 18TH STREET! Only 3 lots left in this community! Large, private wooded lot with several site options. Moments to the Chesapeake Bay/Beach and all its amenities: Water park, dining, crabbing, gambling, charter boats, fishing and endless fun. Previous Perc but will need new, buyer responsible for renewals and permitting. Seller to install street after sale.

  Robyn Day RE/MAX One

  6852 Old Bayside Rd, Chesapeake Beach, MD 20732
• 

  

  /9

  $95,000

  • Land
  • 0.48 Acre
  • $197,917 per Acre

  6510 18th St, Chesapeake Beach, MD 20732

  Three spacious lots remaining. Cleared and previous perc. Minutes to Chesapeake Bay amenities: Boardwalk, charter boat fishing, crabs, dining, gambling.

  Robyn Day RE/MAX One

  6510 18th St, Chesapeake Beach, MD 20732
• 

  

  /9

  $179,000

  • Land
  • 0.73 Acre
  • $245,205 per Acre

  6520 18th St, Chesapeake Beach, MD 20732

  Ready for your builder. Three lots remaining. Previous Perc. Moments to resort life at the beach. Antique stores, restaurants, pubs, quaint shops, charter fishing and fun in the sun.

  Robyn Day RE/MAX One

  6520 18th St, Chesapeake Beach, MD 20732
• 

  

  /5

  $699,990 New Construction

  • 4 Beds
  • 2.5 Baths

  7536 C St, Chesapeake Beach, MD 20732

  RARE opportunity to own a BRAND NEW home with a VIEW OF THE CHESAPEAKE BAY! WALK to restaurants, shops, boardwalk, Brownie's Beach, marinas, concerts at the resort, and so much more from this location in the heart of Chesapeake Beach. Less than an hour away from Washington, D.C. it's the perfect commuter location too. You don't want to miss this rare find. Enjoy picking your colors

  Team Stueckler Keller Williams Flagship

  7536 C St, Chesapeake Beach, MD 20732
• 

  

  /10

  $499,900 Coming Soon

  • 4 Beds
  • 3 Baths
  • 1,012 Sq Ft

  7410 Dakota Ave, Chesapeake Beach, MD 20732

  WELCOME to this Split Fabulous, more pictures coming soon!New roof, new siding and more

  Linda Stock RE/MAX One

  7410 Dakota Ave, Chesapeake Beach, MD 20732
• 

  

  /10

  $475,000 Coming Soon

  • 4 Beds
  • 3 Baths
  • 2,192 Sq Ft

  550 Carla Dr, Huntingtown, MD 20639

  If you’ve ever dreamed of having your own mini-farm without giving up convenience, this is the one. Sitting on three level, open acres in the heart of Huntingtown, this beautifully maintained home has room for everyone, two- and four-legged alike. NO HOA.Inside, you’ll find spacious bedrooms and three full baths, freshly painted with new carpet, new light fixtures, and large, sunny rooms

  Dawn Riley RE/MAX One

  550 Carla Dr, Huntingtown, MD 20639

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