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Homes for Sale near Glenwood Middle School

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  • /26

    $450,000

    • Land
    • 3.36 Acres
    • $133,929 per Acre

    2686 Jennings Chapel Rd, Woodbine, MD 21797

    2686 Jennings Chapel Rd, Woodbine, MD 217973.36 Acres | 1 Well & 1 Septic - Buildable Lot | No HOA | Equestrian-AdjacentA Rare Offering in Coveted Western Howard CountyLocated in one of Maryland’s most sought-after communities, this exceptional 3.36-acre level lot offers the perfect blend of privacy, natural beauty, and accessibility. Nestled in the heart of Western Howard County—consistently

    Agent Photo

    Dawn Chaikin

    Berkshire Hathaway HomeServices PenFed Realty

    (443) 363-1452

    2686 Jennings Chapel Rd, Woodbine, MD 21797
  • /39

    $1,300,000

    • 4 Beds
    • 3 Baths
    • 2,314 Sq Ft

    342 Watersville Rd, Mount Airy, MD 21771

    Welcome to your slice of paradise in Howard County! This stunning 63.5-acre property is a dream come true for anyone looking to embrace the simple beauty of rural living. Picture this: a spacious 2,400 sq ft ranch built in 2014, with an inviting open main area that’s perfect for gatherings. The house faces south, giving you breathtaking views of fields, trees, and rolling hills right from your

    Katrina Hebert Douglas Realty LLC

    342 Watersville Rd, Mount Airy, MD 21771
  • /80

    $1,200,000

    • 4 Beds
    • 5 Baths
    • 5,515 Sq Ft

    725 Chessie Crossing Way, Woodbine, MD 21797

    Offered for the first time by its original owner, this custom-built brick colonial sits gracefully on three private acres and offers over 5,500 square feet of refined living space. With fresh interior paint, beautifully renovated bathrooms, and exceptional outdoor living spaces, this home blends timeless elegance with thoughtful updates inside and out.A long, private driveway leads to the stately

    Karen Nelson Northrop Realty

    725 Chessie Crossing Way, Woodbine, MD 21797
  • /77

    $1,300,000

    • 5 Beds
    • 6 Baths
    • 7,816 Sq Ft

    16900 Old Sawmill Rd, Woodbine, MD 21797

    Nestled on a beautifully landscaped 1-acre lot, this breathtaking home offers over 8,000 sq. ft. of masterfully designed living space. A stunning brick façade, a picturesque walkway, and an extended driveway leading to a side-entry 3-car garage set the tone for the elegance that awaits within.Step through the grand two-story foyer, where gleaming hardwood floors create an ambiance of

    Lisa Kittleman The KW Collective

    16900 Old Sawmill Rd, Woodbine, MD 21797
  • /83

    $1,250,000

    • 6 Beds
    • 3.5 Baths
    • 4,590 Sq Ft

    3109 Spring House Ct, Woodbine, MD 21797

    Magnificent Estate in Warfields Grant on Over an Acre. Nestled in Woodbine’s prestigious Warfields Grant community, this exquisite 5,000+ sq. ft. estate offers unparalleled luxury and an exceptional private retreat backyard, complete with a heated in-ground swimming pool and a walkout lower level with a second kitchen, 2 bedrooms, and a full bathroom. Lovingly maintained, this 6 bedroom, 3.5

    Mike Clevenger Northrop Realty

    3109 Spring House Ct, Woodbine, MD 21797
  • /87

    $1,690,000 Open House 5/17

    • 5 Beds
    • 6 Baths
    • 6,286 Sq Ft

    15620 Linden Grove Ln, Woodbine, MD 21797

    Experience luxury, modern convenience, and energy efficiency in this Toll Brothers estate located in the prestigious Linden Grove community. Boasting 6 bedrooms, 4 full baths, 2 half baths, and 6,286 sqft of meticulously designed living space, this home sits on a 1+ acre lot and offers the perfect blend of elegance and cutting-edge technology.A grand two-story foyer welcomes you into a

    Javon Burden Keller Williams Preferred Properties

    15620 Linden Grove Ln, Woodbine, MD 21797
  • /74

    $1,399,990

    • 5 Beds
    • 6 Baths
    • 5,905 Sq Ft

    15305 Sweetbay St, Woodbine, MD 21797

    Spacious and infused with natural daylight, this desirable model has over 6,000+ finished square feet of luxury space – 5 Bedroom 6 FULL Bath. Home is situated in the sought-after and lovely BELLE HAVEN ESTATES neighborhood. Built on a LUXURY PREMIUM rectangular lot. Featuring an all-brick front, 1+ acre lot set the tone for the rest of the home. Walk into an open hardwood floor foyer with Bed

    Surya Reddi Samson Properties

    15305 Sweetbay St, Woodbine, MD 21797
  • /61

    $1,120,000

    • 5 Beds
    • 3.5 Baths
    • 5,341 Sq Ft

    18311 Chelsea Knolls Dr, Mount Airy, MD 21771

    Stunning former model home in sought-after school district in Howard County, Mount Airy! Nestled on a quiet cul-de-sac, this exquisite Avalon model by Ryan Homes was built in 2015 and once served as the community’s model home. Perfectly situated on nearly an acre backing to trees, this property offers a serene and private setting with ample space for recreation and

    Carla Viviano Viviano Realty

    18311 Chelsea Knolls Dr, Mount Airy, MD 21771
  • /78

    $1,695,000

    • 5 Beds
    • 4.5 Baths
    • 5,912 Sq Ft

    15036 Scottswood Ct, Woodbine, MD 21797

    Unmatched Luxury in Western Howard CountyThis is a RARE opportunity to own one of Howard County’s most exclusive estates! Nestled on 5 pristine acres, this One-of-a-Kind Southern Cape Cod masterpiece redefines luxury living with 5 generously sized bedrooms, 4.5 bathrooms, and exceptional indoor-outdoor spaces that elevate every lifestyle.From the moment you arrive, you're welcomed by

    Rebecca Mason Cummings & Co. Realtors

    15036 Scottswood Ct, Woodbine, MD 21797
  • /108

    $1,280,000

    • 6 Beds
    • 4.5 Baths
    • 8,088 Sq Ft

    818 Hoods Mill Rd, Cooksville, MD 21723

    EXPANSIVE 6BR/4.5BA COLONIAL PRIVATELY TUCKED AWAY ON NEARLY 5 ACRES. ELEGANT 2-STORY FOYER WITH SWEEPING STAIRCASE. FORMAL LIVING ROOM & DINING ROOM PERFECT FOR ENTERTAINING. FABULOUS CHEF'S KITCHEN BOASTS GRANITE COUNTERS, CUSTOM BACKSPLASH, ISLAND, BREAKFAST AREA AND ADJOINING FAMILY ROOM WITH SOARING CEILING AND WOOD STOVE WITH 2-STORY STONE SURROUND. THE UPPER LEVEL HAS A LARGE PRIMARY

    Barry Nabozny RE/MAX Premier Associates

    818 Hoods Mill Rd, Cooksville, MD 21723
  • /32

    $1,999,900 New Construction

    • 5 Beds
    • 5.5 Baths
    • 6,700 Sq Ft

    14069 Monticello Dr, Cooksville, MD 21723

    OPPORTUNITY We have the following property with NEW CONSTRUCTION listed below. NEW CONSTRUCTION PROPERTY Western Howard County Price - Starting at $1.999M, Dependent on Build Timing and Final Options Selected Victorian Grace at Monticello 14069 Monticello Drive - Due to Construction, All Property Visits Require Owner or Builder Present The Home and Garage is of superior

    Jonathan Minerick Homecoin.com

    14069 Monticello Dr, Cooksville, MD 21723
  • /52

    $1,195,000 Open Sat 11AM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 4,920 Sq Ft

    3124 Ellerslie Ct, Glenwood, MD 21738

    Set on a rise in the peaceful enclave of Glen Manor, this home is perfectly located between Glenelg HS and its feeder schools, Bushy Park ES and Glenwood MS. The main level has a huge kitchen/family room combination which provides a great setting for family time. The kitchen includes plenty of 42” solid wood cabinetry, granite countertops with a preparation island, and ss appliances with

    Randy Scourtis Berkshire Hathaway HomeServices PenFed Realty

    3124 Ellerslie Ct, Glenwood, MD 21738
  • /26

    $325,000

    • 2 Beds
    • 1 Bath
    • 728 Sq Ft

    417 Twin Arch Rd, Mount Airy, MD 21771

    Charming and thoughtfully remodeled in 2020, this single-family home offers 728 square feet of stylish living space with 2 bedrooms and 1 full bath, nestled in the peaceful setting of Mount Airy. A long private driveway leads to a welcoming front porch, setting the tone for the inviting interior. Step inside to an open-concept main level with contemporary finishes and soaring vaulted ceilings.

    Bob Lucido Keller Williams Lucido Agency

    417 Twin Arch Rd, Mount Airy, MD 21771
  • /8

    $299,900

    • Land
    • 6 Acres
    • $48,371 per Acre

    1252 Underwood Rd, Sykesville, MD 21784

    Blank canvas awaits for you to build your perfect estate! You will fall in love with this beautiful 6.2 acre lot nestled among preserved AG land in Western Howard County. The long stately driveway is grown over but leads back to the original old house which has collapsed. The approved house site is located at the old house site which has an awesome view of the stream and pond. Let your

    Chuck Zepp EXP Realty, LLC

    1252 Underwood Rd, Sykesville, MD 21784
  • /52

    $899,000

    • 5 Beds
    • 3.5 Baths
    • 4,951 Sq Ft

    2016 Meadow Tree Ct, Cooksville, MD 21723

    Step into this captivating Colonial gracefully tucked away in the idyllic landscape of Western Howard County, where breathtakingly beautiful views of the Penn Oaks Winery and majestic skylines magnificently unfold before your eyes. Set on over an acre of lush, tranquil surroundings, this home boasts 4 large sized bedrooms on the upper level recently updated with new carpet. The main level

    Benjamin Daniels The KW Collective

    2016 Meadow Tree Ct, Cooksville, MD 21723
  • /105

    $700,000

    • 4 Beds
    • 3.5 Baths
    • 4,314 Sq Ft

    15256 Callaway Ct, Glenwood, MD 21738

    This expansive, light-filled end-unit home is located in the Villas at Cattail Creek — a vibrant 55+ active adult community! Offering over 4,000 square feet of finished living space across all three levels, this home provides full main-level living plus a separate, independent living area on the lower level.The main level features gleaming hardwood floors throughout. A private office with French

    Alicyn DelZoppo Northrop Realty

    15256 Callaway Ct, Glenwood, MD 21738
  • /67

    $997,000

    • 4 Beds
    • 2.5 Baths
    • 4,013 Sq Ft

    870 Hoods Mill Rd, Cooksville, MD 21723

    Welcome to this beautifully maintained custom-built home, thoughtfully designed and constructed in 2002 and nestled on a serene and spacious 5 acre lot. This property offers the perfect blend of quality craftsmanship, privacy, and pride of ownership! From the moment you arrive, you'll appreciate the attention to detail and care that has gone into this exceptional home and property. The two

    Reta Sponsky Cummings & Co. Realtors

    870 Hoods Mill Rd, Cooksville, MD 21723
  • /62

    $939,999

    • 5 Beds
    • 3.5 Baths
    • 4,999 Sq Ft

    17025 Hardy Rd, Mount Airy, MD 21771

    Welcome to 17025 Hardy Road – Your Private Oasis in the Heart of Mount Airy. Nestled along the tranquil country roads of Mount Airy, this exquisite home offers over 5,400 square feet of luxurious living space where timeless elegance meets everyday functionality. Set on a beautifully landscaped lot, this one-of-a-kind property delivers the perfect blend of upscale living and thoughtful amenities

    Alex Bounan Long & Foster Real Estate, Inc.

    17025 Hardy Rd, Mount Airy, MD 21771
  • /39

    $524,999

    • 4 Beds
    • 3 Baths
    • 2,110 Sq Ft

    15921 Frederick Rd, Woodbine, MD 21797

    This Property is being sold "AS-IS/WHERE IS" Welcome to 15921 Frederick Rd, a historic single-family home nestled in the Lisbon area of Woodbine, Maryland. Built in 1900, this residence offers a blend of classic charm and modern convenience.**Property Details:**- **Bedrooms:** 4- **Bathrooms:** 2.5- **Living Space:** Approximately 2,310 sq ft- **Lot Size:** 0.71 acresThe home is situated on a

    Aaron LaMere Century 21 Redwood Realty

    15921 Frederick Rd, Woodbine, MD 21797
  • /14

    $375,000

    • Land
    • 3.60 Acres
    • $104,167 per Acre

    0 Duvall Rd Unit MDHW2049414, Woodbine, MD 21797

    Beautiful 3.595 acre building lot in sought after Western Howard County. Large gently sloping homesite with amazing views in Woodbine MD. Land opportunities like this are hard to come by so reach out today to find out more. Perc test complete.

    Ross Wilhelm Compass

    0 Duvall Rd Unit MDHW2049414, Woodbine, MD 21797
  • /54

    $800,000

    • 3 Beds
    • 3 Baths
    • 4,089 Sq Ft

    3703 Cattail Greens Ct, Glenwood, MD 21738

    Beautiful brick-front Colonial residence offering 4,089 square feet, 3 bedrooms, and 3 full baths in sought-after Villas at Cattail Creek. Step into a gracious foyer where a full bathroom and a bedroom await just beyond elegant columns to the right. Hardwood floors continue into the well-appointed study with French doors, while a convenient main floor laundry room—with washer and dryer replaced

    Bob Lucido Keller Williams Lucido Agency

    3703 Cattail Greens Ct, Glenwood, MD 21738
  • /60

    $772,500

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

    3309 Stapleton Dr, Glenwood, MD 21738

    Welcome to this stunning modern home, where meticulous craftsmanship meets contemporary elegance. Situated on a beautifully landscaped 1 acre lot, this property boasts exceptional hardscaping and a fully fenced rear yard with a charming split-rail design. From the moment you arrive, you’ll appreciate the paved driveway leading to a spacious two-car garage, which not only provides ample storage

    Joseph Wathen RE/MAX Advantage Realty

    3309 Stapleton Dr, Glenwood, MD 21738
  • /54

    $780,000

    • 4 Beds
    • 3.5 Baths
    • 3,122 Sq Ft

    425 Twin Arch Rd, Mount Airy, MD 21771

    Tucked at the end of a tree-lined drive, this beautifully updated colonial home offers a peaceful retreat with sweeping hilltop views. From the covered front porch, take in the tranquility of the surrounding landscape.Step inside to a warm and welcoming main level featuring hardwood floors and a smart, flowing layout. The updated kitchen is a standout, featuring crisp white cabinetry,

    Jeffrey Ganz Century 21 Redwood Realty

    425 Twin Arch Rd, Mount Airy, MD 21771
  • /29

    $700,000

    • Land
    • 9 Acres
    • $79,545 per Acre

    14459 Frederick Rd, Cooksville, MD 21723

    8.8 acre lot in Howard County. Unique opportunity to build your dream home. Sale includes 14459 & 14439 Frederick Rd. Approved Perc, call for details.

    Holly Greenstreet Hyatt & Company Real Estate, LLC

    14459 Frederick Rd, Cooksville, MD 21723
  • /93

    $4,499,999

    • 7 Beds
    • 11 Baths
    • 16,279 Sq Ft

    3415 Shady Ln, Glenwood, MD 21738

    Unparalleled quality and craftsmanship is evident at once upon entering through the oversize double doors of this executive luxury home. Custom built by the Award Winning, Bethel Regency Homes in 2021 with 7 Bedrooms and 8/3 Baths. The completely finished 8-car capacity Garages are a car collector's dream. The athlete or fitness enthusiast will appreciate the Gym and sunken indoor Sport Court

    Keisha McClain Hubble Bisbee Christie's International Real Estate

    3415 Shady Ln, Glenwood, MD 21738
  • /39

    $600,000

    • 3 Beds
    • 2 Baths
    • 2,140 Sq Ft

    652 W Watersville Rd, Mount Airy, MD 21771

    **REDUCED**Come see this GREAT 3 bedroom, 2 full bath, all brick Rancher that sits on just under 4 acres in Howard County! Pull up the circular driveway and come right inside, you'll love the gorgeous hardwood floors throughout the main level. The family room to your left has a bay window, recessed lights and wood-burning fireplace for cozy nights at home and to your right is the kitchen,

    Lynn Ikle Redfin Corp

    652 W Watersville Rd, Mount Airy, MD 21771
  • /25

    $675,000

    • Land
    • 1.18 Acres
    • $572,034 per Acre

    15309 Leondina Dr, Glenwood, MD 21738

    Design & Build your own Estate Home! 1.18 Acre Estate Homesite located within the Vineyards at Cattail Creek, a Private Community of Custom Designed Homes, for those who appreciate the extraordinary w/plenty of open spaces & quiet country lanes to bike, jog or just take a leisurely stroll & acres of woods to discover & enjoy. (Perc completed, Well Included)

    Diane Kenworthy Northrop Realty

    15309 Leondina Dr, Glenwood, MD 21738
  • /40

    $774,999

    • 5 Beds
    • 3 Baths
    • 3,431 Sq Ft

    14816 Bushy Park Rd, Woodbine, MD 21797

    Welcome to this stunning 5-BR, 3-FB home in the heart of Woodbine! This turn-key residence offers bright and open interiors, featuring rich hardwood floors throughout. The EXPANSIVE family room boasts an oversized window, flooding the space with natural light, and a cozy wood stove for added warmth. The modern kitchen is a chef’s dream, complete with stainless steel appliances, sleek granite

    Sean Der Compass

    14816 Bushy Park Rd, Woodbine, MD 21797
  • /20

    $275,000

    • Land
    • 3.02 Acres
    • $91,060 per Acre

    2669 Roxbury Mills Rd, Glenwood, MD 21738

    What a unique opportunity-to Build Pickle Courts! Are you looking for land that is un-encumbered? This property has many opportunity uses such as, a storage lot, cell tower, parking lot, recreation lot or some other type of recreational courts. There is a well onsite. The septic field was approved back in the late 80's but recently has failed for conventional and sand mound systems in 2023.

    Cindy DelZoppo Northrop Realty

    2669 Roxbury Mills Rd, Glenwood, MD 21738
  • /98

    $5,000,000

    • 16 Beds
    • 12 Baths
    • 16,270 Sq Ft

    16449 Ed Warfield Rd, Woodbine, MD 21797

    Culturally, historically, and architecturally significant, Oakdale, circa 1838 and 1898, ancestral home of Maryland Governor Edwin Warfield, is a magnificent estate on a tranquil 180-acre tract only 20 miles from both the Washington and Baltimore beltways. On The National Register of Historic Places, the main house boasts 24 rooms and 5.1 baths, comprising over 9,500 sq. ft. Impressive, original

    Richard Watson Long & Foster Real Estate, Inc.

    16449 Ed Warfield Rd, Woodbine, MD 21797
  • /102

    $5,000,000

    • 16 Beds
    • 12 Baths
    • 16,270 Sq Ft

    16449 Ed Warfield Rd, Woodbine, MD 21797

    Culturally, historically, and architecturally significant, Oakdale, circa 1838 and 1898, ancestral home of Maryland Governor Edwin Warfield, is a magnificent estate on a tranquil 180-acre tract only 20 miles from both the Washington and Baltimore beltways. On The National Register of Historic Places, the main house boasts 24 rooms and 5.1 baths, comprising over 9,500 sq. ft. Impressive, original

    Richard Watson Long & Foster Real Estate, Inc.

    16449 Ed Warfield Rd, Woodbine, MD 21797
  • /19

    $295,000

    • Land
    • 1.25 Acres
    • $236,000 per Acre

    15948 Union Chapel Rd, Woodbine, MD 21797

    CORNER LOT ON 1.25 ACRES. EXISTING WELL & SEPTIC! GREAT PROPERTY OPEN TO ANY TYPE OF BUSINESS! USED TO BE DAISY TRADING POST!

    Jennifer Drennan Taylor Properties

    15948 Union Chapel Rd, Woodbine, MD 21797
  • /23

    $2,900,000 New Construction

    • 4 Beds
    • 4.5 Baths

    15309 Leondina Dr, Glenwood, MD 21738

    Design and build your own estate Home! 1.18 acre estate homesite located within the Vineyards at Cattail Creek, a private community of custom designed homes, for those who appreciate the extraordinary with plenty of open spaces & quiet country lanes to bike, jog or just take a leisurely stroll & acres of woods to discover & enjoy. New construction - to be built home. Bring your builder or use

    Diane Kenworthy Northrop Realty

    15309 Leondina Dr, Glenwood, MD 21738
  • /23

    $2,700,000 New Construction

    • 4 Beds
    • 4.5 Baths

    15309 Leondina Dr, Glenwood, MD 21738

    Design and build your own estate Home! 1.18 acre estate homesite located within the Vineyards at Cattail Creek, a private community of custom designed homes, for those who appreciate the extraordinary with plenty of open spaces & quiet country lanes to bike, jog or just take a leisurely stroll & acres of woods to discover & enjoy. New construction - to be built home. Bring your builder or use

    Diane Kenworthy Northrop Realty

    15309 Leondina Dr, Glenwood, MD 21738
  • /10

    $1,075,000 Coming Soon

    • 6 Beds
    • 3 Baths
    • 5,060 Sq Ft

    719 Chessie Crossing Way, Woodbine, MD 21797

    Custom built home on 4 acres of beautiful, lush grounds. Large foyer entry welcomes you into this well-maintained home built for family gatherings and entertaining. Features include recently refinished hardwood floors throughout the main and upper levels, 9-foot ceilings on the main level, stained wood trim doors and Pella windows throughout. Propane heats the house and hot water. Interior

    John Fontana Keller Williams Realty Centre

    719 Chessie Crossing Way, Woodbine, MD 21797
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