Homes for Sale near Windy Hill Middle School

• 

  

  /2

  $75,000

  • Land
  • 8 Acres
  • $9,271 per Acre

  2955 Chesapeake Beach Rd, Chesapeake Beach, MD 20732

  8 acres of land off Chesapeake Beach Road

  

  Sarah Swann

  Baldus Real Estate, Inc.

  (443) 291-5954

  2955 Chesapeake Beach Rd, Chesapeake Beach, MD 20732
• 

  Explore Windy Hill Middle School

• 

  

  /2

  $99,990

  • Land
  • 0.13 Acre
  • $769,154 per Acre

  7536 C St, Chesapeake Beach, MD 20732

  This is a rare opportunity to own land and build new construction in the heart of Chesapeake Beach. Walk to everything the town has to offer. Just a short stroll to the boardwalk where you can watch the ships go by, see the sunrise, or walk to the town beach. This location is also walkable to restaurants, marinas, and concerts at the resort. It's the perfect spot to build your dream beach

  Adam Hoyt

  Keller Williams Flagship

  (443) 363-0471

  7536 C St, Chesapeake Beach, MD 20732
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  /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 and finishes

  Adam Hoyt

  Keller Williams Flagship

  (443) 785-6316

  7536 C St, Chesapeake Beach, MD 20732
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  /30

  $579,900

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  9333 Bay Ave, North Beach, MD 20714

  Live Where Every Day Feels Like a Vacation!9333 Bay Avenue | North Chesapeake Beach, MD. Great investment opportunity with a total of 3 lots. Build a second home and/or expand existing home. Your choice. Come take a look and see it for yourself.Step into timeless coastal luxury at 9333 Bay Avenue—an exceptional 3-bedroom, 2.5-bath bayfront retreat that invites you to live the life

  Van Mason Maryland Dream Home Realty

  9333 Bay Ave, North Beach, MD 20714
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  /18

  $524,900

  • 4 Beds
  • 2.5 Baths
  • 1,462 Sq Ft

  3600 4th St, North Beach, MD 20714

  Have you been searching for a 4-bedroom, 2.5-bath home that truly checks all the boxes? Welcome to 3600 4th Street—your next move! This beautiful home was fully updated in 2025. Step inside to discover a bright, modern kitchen featuring brand-new cabinets, sleek quartz countertops, stainless steel appliances, and luxury vinyl wide plank flooring that runs throughout the main level—perfect for

  Michelle Faig CENTURY 21 New Millennium

  3600 4th St, North Beach, MD 20714
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  /36

  $698,000

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

  2425 Woodland Ct, Chesapeake Beach, MD 20732

  3200 sq. ft. community 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 as well as bulk pick up and snow clearing by the Town. First floor formal dining with bay window, hardwood flooring, spacious family room with custom wall-to-wall built-in, upgraded kitchen

  Pamela Debnam Houwzer, LLC

  2425 Woodland Ct, Chesapeake Beach, MD 20732
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  /54

  $635,000

  • 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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  /40

  $625,000

  • 4 Beds
  • 2 Baths
  • 2,857 Sq Ft

  8236 Bayside Rd, Chesapeake Beach, MD 20732

  The perfect beach getaway! Nestled in the heart of Chesapeake Beach, this expansive residence offers an unparalleled opportunity to embrace coastal living at its finest. Imagine starting your day with a breathtaking sunrise from your water view balcony, as it rises over the Chesapeake Bay, followed by a leisurely stroll to the vibrant boardwalk of North Beach. Then end your day on the wonderful

  Greg Beckman Berkshire Hathaway HomeServices PenFed Realty

  8236 Bayside Rd, Chesapeake Beach, MD 20732
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  /27

  $550,000

  • 4 Beds
  • 1 Bath
  • 2,553 Sq Ft

  1325 Pushaw Station Rd, Sunderland, MD 20689

  Discover the tranquility of country living at 1325 Pushaw Station Rd, Sunderland, MD. Nestled on 27.5 wooded acres, this classic brick rancher offers peace, privacy, and potential. Featuring a cozy living room fireplace, spacious layout, and a finished basement, this home is perfect for those seeking space to grow, garden, or simply unwind. The property’s acreage provides endless options—create

  LaShanda Pullam CENTURY 21 New Millennium

  1325 Pushaw Station Rd, Sunderland, MD 20689
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  /64

  $599,900

  • 4 Beds
  • 3.5 Baths
  • 2,496 Sq Ft

  8207 Elm Ln, Chesapeake Beach, MD 20732

  Appraised at $636,000! Previous buyer couldn't perform and their loss is your opportunity! New custom built coastal home in Chesapeake Beach! Great location, in a sought after area, just a few blocks to all the restaurants, parks, boardwalks and beaches. Beautiful kitchen with granite countertops, stainless steel appliances, recessed lighting, ample sized pantry, countertop seating and open

  Conor Stueckler Keller Williams Flagship

  8207 Elm Ln, Chesapeake Beach, MD 20732
• 

  

  /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
• 

  

  /21

  $649,999

  • 8 Beds
  • 3 Baths
  • 3,840 Sq Ft

  7625 B St, Chesapeake Beach, MD 20732

  Waterview with street in front of you then the bay. It has 2 homes with 3 rentals presently. 1 home in front with side by side rentals their attached. Then a cottage in back with more lots. It would make a great spot for single family home or a family compound. There is new roof on back cottage. Presently have all 3 places rented. This property had 3 kitchens. 3 rentals Waterfront with walk way

  Debbie Buckingham Samson Properties

  7625 B St, Chesapeake Beach, MD 20732
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  /27

  $449,900

  • 4 Beds
  • 2.5 Baths
  • 1,736 Sq Ft

  3808 Chesapeake Beach Rd, Chesapeake Beach, MD 20732

  Welcome to 3808/3810 Chesapeake Beach Road – A Charming Coastal Retreat in the Heart of Town!This well-maintained home offers the perfect blend of comfort, functionality, and location—all just a short walk from the Chesapeake Bay. Nestled on two spacious lots with a large, fenced-in yard, this property provides ample green space and the potential for future expansion (please consult

  Danny Martin Keller Williams Flagship

  3808 Chesapeake Beach Rd, Chesapeake Beach, MD 20732
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  /15

  $199,000

  • Land
  • 0.15 Acre
  • $1,326,667 per Acre

  8314 Bayside Rd, Chesapeake Beach, MD 20732

  Ready to make your move to Chesapeake Beach? Not only that, are you ready to build the house of your dreams with a water view? Come walk the lot of 8314 Bayside road to picture your future mornings sipping coffee on your front porch. Public Sewer and water hookups already available as well as electricity! Only a couple of blocks from the Chesapeake Bay, this lot is not only convenient to the

  Haley Taylor Real Broker, LLC - Dunkirk

  8314 Bayside Rd, Chesapeake Beach, MD 20732
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  /38

  $449,990

  • 3 Beds
  • 4 Baths
  • 2,155 Sq Ft

  3816 Bedford Dr, North Beach, MD 20714

  Discover coastal living at its finest in this beautifully appointed home located at 3816 Bedford Drive, North Beach, MD. With 1,690 square feet of space, this charming residence features three spacious bedrooms, two full baths, two half baths, & a finished basement. Delight in the elegance of hardwood floors gracing the foyer, kitchen, and dining area. The modern kitchen is a chef's dream,

  William Gray Home Towne Real Estate

  3816 Bedford Dr, North Beach, MD 20714
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  /113

  $879,000

  • 3 Beds
  • 5 Baths
  • 2,566 Sq Ft

  8074 Windward Key Dr, Chesapeake Beach, MD 20732

  OPEN HOUSE 7/19 & 7/20!! Come join me and take a look at this beautifully renovated home!Excellent condition 3 bedroom 3 full bath and 2 half bath townhouse located in the desirable neighborhood of Windward Key! This perfectly located home has bay views out of every front window and water front views of the neighborhood marina on fishing creek in the back. Inside you will find a beautifully

  leah weeks Blue Dot Real Estate Bowie

  8074 Windward Key Dr, Chesapeake Beach, MD 20732
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  /41

  $499,900

  • 3 Beds
  • 3 Baths
  • 1,722 Sq Ft

  1237 Alta Dr, Sunderland, MD 20689

  Beautifully updated modern split foyer home on private, wooded lot. Open floor plan boasts bright, light filled kitchen with white, soft close cabinets, quartz countertops, spacious island, stainless steel appliances and dining area. The kitchen opens up to a large, brand new deck that boasts a magnificent forested view. The main level includes three bedrooms and two full bathrooms, highlighted

  David Jimenez RE/MAX Distinctive Real Estate, Inc.

  1237 Alta Dr, Sunderland, MD 20689
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  /23

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  8400 Pushaw Station Rd, Owings, MD 20736

  Owings, Calvert County - Great northern location within 1-hr to DC, Annapolis, Waldorf, and several military bases. Absolutely NO COVENANTS OR RESTRICTIONS. Home has 3 bedroom and 2 full baths. Master bedroom and one full bath is at one end of the home and the other two bedrooms and second full bath are at the other end. Nice large kitchen with dining area and patio doors to rear yard. Your

  Beverly Rasmussen RE/MAX Realty Group

  8400 Pushaw Station Rd, Owings, MD 20736
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  /26

  $1,200,000

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft

  3826 Harbor Rd, Chesapeake Beach, MD 20732

  Waterfront Property zoned Marine Commercial Residential which equates to so much potential located on Fishing Creek which leads out to the Chesapeake Bay. Features include 4 boat slips, Full Shedding Operation, Walk In Box, Shed. Views of the Water from one side faces Fishing Creek to the other side which face the Chesapeake Bay. 3 Bedrooms, 1 Bath (with additional bath rough in), Beautiful

  Tammy L Marlowe RE/MAX One

  3826 Harbor Rd, Chesapeake Beach, MD 20732
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  /45

  $485,000

  • 4 Beds
  • 2 Baths
  • 2,540 Sq Ft

  3902 13th St, Chesapeake Beach, MD 20732

  VA assumable 2.25% interest rate!!! Beautifully updated 4-bedroom, 2-bath rambler with a fully finished basement, offering approximately 2,500 sq ft on a spacious corner lot in Chesapeake Beach! You'll love the short walk to the Chesapeake Bay, local restaurants, shops, and the town grocery store. This home is conveniently located just 40 minutes to Joint Base Andrews and Washington, D.C.,

  Team Stueckler Keller Williams Flagship

  3902 13th St, Chesapeake Beach, MD 20732
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  /18

  $369,900

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  4006 6th St, North Beach, MD 20714

  ***OPEN HOUSE SUNDAY, JULY 20TH 1-3 PM*****Charming Coastal Cottage with Modern Flair – Just 2 Blocks from the Bay!**Welcome to 4006 6th Street, a lovingly renovated 2-bed, 1-bath gem that perfectly balances 1940s charm with today’s comforts. Bathed in natural light and boasting high ceilings, this single-level cottage features rich hardwood floors, an open-concept layout, and

  Danny Martin Keller Williams Flagship

  4006 6th St, North Beach, MD 20714
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  /67

  $369,000

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  2340 Forest Ridge Terrace, Chesapeake Beach, MD 20732

  Discover the perfect blend of modern comfort and coastal charm in this beautiful three bedrooms, 2.5-bath townhome in the Richfield Station community. Owner added $20,000 worth of gorgeous hardwood flooring on all levels and $5000 new steel appliances. Thoughtfully designed with an open and inviting layout, this home offers a warm and welcoming atmosphere from the moment you step inside. The

  Lydia Lin Allison James Estates & Homes

  2340 Forest Ridge Terrace, Chesapeake Beach, MD 20732
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  /39

  $500,000

  • 3 Beds
  • 2 Baths
  • 1,299 Sq Ft

  8321 Bayside Rd, Chesapeake Beach, MD 20732

  Welcome to 8321 Bayside Drive, a charming 3-bedroom, 2-bath home offering sweeping Chesapeake Bay water views in the quaint beach town of Chesapeake Beach. Enjoy peaceful mornings and stunning sunrises from your private deck, with the added benefit of community-owned bayfront property directly behind the home—ensuring your views are preserved.Inside, the home features an updated kitchen

  Bob Chew Samson Properties

  8321 Bayside Rd, Chesapeake Beach, MD 20732
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  /63

  $380,000

  • 3 Beds
  • 1 Bath
  • 1,242 Sq Ft

  3816 Chesapeake Beach Rd, Chesapeake Beach, MD 20732

  Want to live near the beach? This amazing 3 bedroom beach cottage is only 2 blocks from the Bay and sure to please. Large Family Room with plenty of natural light and hardwood floors. In the Kitchen you will find quartz counters, white kitchen cabinets, stainless steel appliances including a counter depth upgraded refrigerator with a see-through door. Washer and Dryer are off the Kitchen. The

  Jeanine Paxton RE/MAX One

  3816 Chesapeake Beach Rd, Chesapeake Beach, MD 20732
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  /59

  $824,900

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

  310 Owings Hill Ct, Owings, MD 20736

  Welcome to 310 Owings Hill Court, an exceptional home nestled on almost 3 acres in a serene, wooded setting at the end of a quiet cul-de-sac. With nearly 5,000 square feet of living space, this five-bedroom, 3.5-bath residence offers the perfect blend of comfort, elegance, and functionality.The main level offers a spacious, light-filled layout that’s perfect for both everyday living and

  Alexandra Boucher TTR Sotheby's International Realty

  310 Owings Hill Ct, Owings, MD 20736
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  /42

  $489,000

  • 3 Beds
  • 4 Baths
  • 1,928 Sq Ft

  3668 Bedford Dr, North Beach, MD 20714

  Live the Bayfront Dream in Style — North Beach Luxury Townhome! Tucked into the wooded enclave of San Francisco on the Bay—a private, sought-after community in charming North Beach—this luxury townhome blends coastal vibes with modern sophistication. North Beach is a picturesque Chesapeake Bay gem, known for its scenic boardwalk, sandy beaches, boutique shops, local coffeehouses, and

  Jason Donovan RE/MAX Leading Edge

  3668 Bedford Dr, North Beach, MD 20714
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  /108

  $1,150,000

  • 6 Beds
  • 4.5 Baths
  • 6,169 Sq Ft

  5 Cross Point Dr, Owings, MD 20736

  Beautiful, former model home in the sought after community of Cross Point with 4 FINISHED LEVELS on a 1 acre wooded homesite! Six (6) Bedrooms, Four (4) Full Baths, Powder Room, Two Story Foyer, Two Story Family Room, Finished Attic/Loft, Finished Basement w/2nd Kitchen, Finished Office on Main Level with separate outside & inside entrance and 2 Car Detached Garage. Main level Gourmet Kitchen

  Lynn Smithburger CENTURY 21 New Millennium

  5 Cross Point Dr, Owings, MD 20736
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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
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  /42

  $449,900

  • 3 Beds
  • 2.5 Baths
  • 2,064 Sq Ft

  6571 11th St, Chesapeake Beach, MD 20732

  Welcome to your hidden gem in the heart of Chesapeake Beach. This split-foyer beauty is tucked away, giving you that peace-and-quiet feel with easy access to the action. Step inside to a bright, open vibe with high ceilings and space that flows. The roof, windows, and doors? All newer—so you’ve got that fresh feel without the hassle. Upstairs brings you a sleek, newly updated ensuite—spa vibes,

  Danielle Sloan JPAR Real Estate Professionals

  6571 11th St, Chesapeake Beach, MD 20732
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  /113

  $929,500

  • 3 Beds
  • 5 Baths
  • 2,566 Sq Ft

  8074 Windward Key Dr, Chesapeake Beach, MD 20732

  OPEN HOUSE 6/21/25 Excellent condition 3 bedroom 3 full bath and 2 half bath townhouse located in the desirable neighborhood of Windward Key! This perfectly located home has bay views out of every front window and water front views of the neighborhood marina on fishing creek in the back. Inside you will find a beautifully remodeled kitchen with an open floor plan throughout and a cozy fire place

  leah weeks Blue Dot Real Estate Bowie

  8074 Windward Key Dr, Chesapeake Beach, MD 20732
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  /42

  $465,000

  • 4 Beds
  • 3 Baths
  • 1,860 Sq Ft

  3917 13th St, Chesapeake Beach, MD 20732

  Welcome to your new home! Everyday can be a vacation with this home’s proximity to the beach, a water park, and several hotels and resorts. This charming home boasts upgraded flooring, kitchen appliances, and bathrooms. The primary suite can be a sanctuary, with a fully remodeled bathroom. There is ample space to spread out and entertain with 3 additional bedrooms and 2 additional full

  Debora Jones CENTURY 21 New Millennium

  3917 13th St, Chesapeake Beach, MD 20732
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  /62

  $734,999

  • 5 Beds
  • 4 Baths
  • 3,700 Sq Ft

  7335 Quaking Dr, Sunderland, MD 20689

  VA ASSUMABLE LOAN AT 2.25%Lovely 5-Bedroom Home with some Great Features in Aspen WoodsThis 5-bedroom, 4-full bathroom home sits on 1.5 acres in the desirable Aspen Woods subdivision. Coming down the driveway you'll notice the usable front yard, the spacious front porch, perfect for relaxing in the morning or catching the sunsets in the evening, and the detached 2 car garage for

  Susan Cleary RE/MAX One

  7335 Quaking Dr, Sunderland, MD 20689
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  /34

  $368,000

  • 3 Beds
  • 2.5 Baths

  8005 Forest Ridge Dr Unit 9, Chesapeake Beach, MD 20732

  OPEN HOUSE Sunday, 7/27/25 2:00-4:00 pm. Owner offering a two-year Home Warranty. Both inspection & appraisal were completed and reflected in the price Appraisal OF March 2025. Richfield Station gem, great home with tons of natural light, and recessed lighting throughout. Installed Feb. 2024 - Sleek newer laminate wood flooring on main level, upgraded carpet on upper level. The main level

  Lauren Leggett Long & Foster Real Estate, Inc.

  8005 Forest Ridge Dr Unit 9, Chesapeake Beach, MD 20732
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  /2

  $90,000

  • Land
  • 3.00 Acres
  • $30,000 per Acre

  6650 Solomons Island Rd N, Sunderland, MD 20689

  3 wooded acres available in the heart of Calvert County. This lot is part of an estate sale but there is documentation that the lot was perced a very long time ago. It would need to be renewed, but we have documents for the original perc test. This lot is beautiful and in a great location for commuting, schools, shopping, nature trails, etc. Call today!

  Kadie Gertz RE/MAX One

  6650 Solomons Island Rd N, Sunderland, MD 20689
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  /64

  $899,900

  • 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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  /3

  $80,000

  • Land
  • 1.34 Acres
  • $59,701 per Acre

  8410 Pushaw Station Rd, Owings, MD 20736

  CALVERT COUNTY'S FINEST - OWINGS, MD - This beautiful acre building lot offers the perfect blend of privacy and convenience, located in a peaceful, quiet neighborhood with distant neighbors. Surrounded by mature trees, this property is ideal for those seeking a serene, natural setting without the restrictions of an HOA. Nestled in the countryside, you can enjoy the tranquility of rural living

  Beverly Rasmussen RE/MAX Realty Group

  8410 Pushaw Station Rd, Owings, MD 20736
• 

  

  /12

  $599,000

  • Land
  • 2.07 Acres
  • $289,372 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

  Sherri Verdon RE/MAX One

  125 Prospect Dr, Sunderland, MD 20689
• 

  

  /4

  $100,000

  • Land
  • 1.09 Acres
  • $91,743 per Acre

  3664 Brookeside Dr, Chesapeake Beach, MD 20732

  Calvert County PERC evaluation completed and filed on 04/11/2023 for a 4,000-4,999 square foot home, 1.09 acre lot in Chesapeake Beach.

  Richard Polish Sid Sells Maryland Realty

  3664 Brookeside Dr, Chesapeake Beach, MD 20732
• 

  

  /10

  $179,000

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

  6520 18th St, Chesapeake Beach, MD 20732

  Only three lots left! Cleared and previously perced. Buyer responsible for updates and permitting. Bring your builders. Just 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
• 

  

  /14

  $199,000

  • Land
  • 5 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

Showing Results 1 - 40, Page 1 of 2