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Homes for Sale near Glenwood Middle School

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  • /30

    $450,000

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

    2686 Jennings Chapel Rd, Woodbine, MD 21797

    2686 Jennings Chapel Rd, Woodbine, MD 21797 3.36 Acres | Buildable Lot | * Updated Perc Test Successfully completed 7-31-25!, Well, Electric, & CableNo HOA | Equestrian-Adjacent A Rare Offering in Coveted Western Howard County Located 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.

    Agent Photo

    Dawn Chaikin

    Berkshire Hathaway HomeServices PenFed Realty

    (443) 363-1452

    2686 Jennings Chapel Rd, Woodbine, MD 21797
  • /52

    $5,300,000

    • 3 Beds
    • 2 Baths
    • 2,233 Sq Ft

    2698 Jennings Chapel Rd, Woodbine, MD 21797

    MAGNIFICENT 63-ACRE EQUESTRIAN ESTATELocated in Western Howard County, Maryland Whether you’re seeking an equestrian paradise or a luxurious private estate, your search ends here. This extraordinary property, nestled in Maryland’s highly sought-after Western Howard County Horse Country, offers breathtaking panoramic views framed by mature forest—delivering elegance, exclusivity, and privacy.

    Agent Photo

    Dawn Chaikin

    Berkshire Hathaway HomeServices PenFed Realty

    (410) 304-6489

    2698 Jennings Chapel Rd, Woodbine, MD 21797
  • /8

    $849,999 Coming Soon

    • 3 Beds
    • 4 Baths
    • 3,956 Sq Ft

    1629 Brittle Branch Way, Woodbine, MD 21797

    Nestled on 3 peaceful acres in Woodbine, this beautifully maintained CUSTOM builder brick home boasts 3 bedrooms and 2 1⁄2 baths on the main level, 9' ceilings in the family room, kitchen, living and dining room, along with a large gourmet kitchen featuring a center island, 42”h natural maple wall cabinets and upgraded stainless steel appliances. The lower level is fully finished with an

    Agent Photo

    Vicki Baxter

    Cummings & Co. Realtors

    (410) 888-0037

    1629 Brittle Branch Way, Woodbine, MD 21797
  • /60

    $1,480,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 4,813 Sq Ft

    2686 -B Jennings Chapel Rd, Woodbine, MD 21797

    2686 Jennings Chapel Rd, Woodbine, MD 217973.36 Acres | Private Well | No HOA | Adjacent to Premier Equestrian Facility Explore custom home options for this lot with Timberlake Design Build one of Maryland's premier custom home builders. Build Your Dream Home with Timberlake Design Build – Luxury Living in Western Howard CountyWelcome to a truly rare opportunity in one of Maryland’s most

    Agent Photo

    Dawn Chaikin

    Berkshire Hathaway HomeServices PenFed Realty

    (410) 983-3522

    2686 -B Jennings Chapel Rd, Woodbine, MD 21797
  • /116

    $1,699,999

    • 6 Beds
    • 7 Baths
    • 7,569 Sq Ft

    3595 Willow Birch Dr, Glenwood, MD 21738

    We invite you to visit Willow Birch Estate, a stunning brick home in the Cattail Creek community, now offered at $1.699M. Don’t miss your chance to own more than 7,500 sq ft of finished living space on a professionally landscaped acre-plus corner lot! A sweeping circular drive, brick-paved walkway, and double-door entry lead into a dramatic two-story foyer with a grand dual staircase and

    Varun Vasudeva HomeSmart

    3595 Willow Birch Dr, Glenwood, MD 21738
  • /76

    $1,245,000

    • 6 Beds
    • 4 Baths
    • 4,553 Sq Ft

    15606 Bushy Park Rd, Woodbine, MD 21797

    Private driveway. Do NOT drive past listed property to turn. Only use the space in front of the garage to park and turn around. Thank you for your understanding. Back on the market, another buyer's loss, your gain! Stunning contemporary 5,400+ sqft home on 4.4 acres, fully updated with exceptional design. Flooded with light, featuring architectural details, 6 bedrooms (2 per level), and a

    Jack Mager Redfin Corp

    15606 Bushy Park Rd, Woodbine, MD 21797
  • /13

    $1,599,900

    • 5 Beds
    • 5.5 Baths
    • 4,535 Sq Ft

    863 Morgan Station Rd, Woodbine, MD 21797

    Introducing Catonsville Homes in Woodbine! Construction is set to commence in January with completion anticipated in Summer 2026. Catonsville Homes proudly presents the Ryleigh floorplan, which will be meticulously crafted on a spacious 1.118-acre homesite. As you approach, you'll be drawn in by the inviting full porch, featuring a stylish metal seam roof, complemented by a stone-to-grade front

    David Scranton Compass

    863 Morgan Station Rd, Woodbine, MD 21797
  • /85

    $1,200,000

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft

    15521 Foxpaw Trail NW, Woodbine, MD 21797

    Welcome to 15521 Foxpaw NW Trail, a spectacular Colonial nestled in the prestigious Foxport community. This residence blends timeless elegance with modern updates, featuring a brand-new roof, renovated kitchen and bathrooms, updated HVAC, and more. Inside, gleaming hardwood floors, classic moldings, and sun-filled interiors create an inviting ambiance. The grand two-story foyer is flanked by

    Mike Clevenger Northrop Realty

    15521 Foxpaw Trail NW, Woodbine, MD 21797
  • /94

    $1,100,000

    • 4 Beds
    • 4.5 Baths
    • 5,509 Sq Ft

    15300 Doe Hill Ct, Woodbine, MD 21797

    Welcome to 15300 Doe Hill Court, a spectacular Colonial residence tucked away in the prestigious Wellington West community. Brimming with timeless elegance and thoughtful design, this home showcases gleaming hardwood floors on the main and upper levels, along with classic moldings, and sun-drenched interiors that exude warmth and sophistication. Step inside the grand two-story foyer, gracefully

    Anthony Friedman Northrop Realty

    15300 Doe Hill Ct, Woodbine, MD 21797
  • /51

    $1,099,000

    • 4 Beds
    • 2.5 Baths
    • 3,226 Sq Ft

    16005 Fields End Ct, Woodbine, MD 21797

    A true Southern Living gem! Designed by renowned architect William Poole, this exquisite semi-custom residence perfectly marries classic charm with modern luxury. The upgraded exterior finishes—including recently replaced siding, fascia, soffit, and gutters, premium roof —promise the quality that awaits inside. Step into over 3,200+ finished square feet across the upper two floors and be amazed

    Karen Thompson Berkshire Hathaway HomeServices PenFed Realty

    16005 Fields End Ct, Woodbine, MD 21797
  • /73

    $1,379,800

    • 7 Beds
    • 4.5 Baths
    • 7,348 Sq Ft

    15501 Bushy Tail Run, Woodbine, MD 21797

    Welcome to this stunning contemporary home, set on 3.14 private acres, thoughtfully designed to combine luxury with modern comfort. Nestled on a serene private lot, this residence is ideal for both entertaining guests and enjoying tranquil everyday living. Step into the impressive 2-story foyer through striking double front doors, featuring sleek marble tile. Expansive Pella windows and

    Lily Alvarado Long & Foster Real Estate, Inc.

    15501 Bushy Tail Run, Woodbine, MD 21797
  • /38

    $1,799,900 New Construction

    • 5 Beds
    • 5.5 Baths
    • 4,960 Sq Ft

    869 Morgan Station Rd, Woodbine, MD 21797

    Nestled on a picturesque 1.15-acre lot, this to-be-built custom home by Catonsville Homes features the exquisite Chapel Hill II model, offering a perfect blend of luxury and comfort. Boasting an impressive 4,960 square feet above grade, this home is adorned with high-end upgrades and thoughtful design elements throughout. The exterior welcomes you with a charming wrap-around front porch accented

    David Scranton Compass

    869 Morgan Station Rd, Woodbine, MD 21797
  • /32

    $1,899,999 New Construction

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

    14069 Monticello Dr, Cooksville, MD 21723

    Western Howard County Price - Starting at $1.899M, Dependent on Build Timing, Final Options Selected, and As-Built Victorian Grace at Monticello 14069 Monticello Drive - The Home and Garage is of superior construction and construction materials. This IS NOT a "builder spec" home. It measure around 6,700 sq. ft. including the basement, main living levels, third floor, garage and covered decking.

    Jonathan Minerick Homecoin.com

    14069 Monticello Dr, Cooksville, MD 21723
  • /14

    $1,250,000 New Construction

    • 5 Beds
    • 7 Baths
    • 6,800 Sq Ft

    16365 Camalo Dr, Mount Airy, MD 21771

    An incredible opportunity to purchase this stunning piece of land and custom build the home of your dreams! The seller has taken the time and expense of working with an established architect to design and provide an exquisite floor plan that includes not just well thought out interior details, but showcases an outdoor oasis with hardscaping, an in ground pool, sport/tennis court, and more! THERE

    Lauren Shapiro Long & Foster Real Estate, Inc.

    16365 Camalo Dr, Mount Airy, MD 21771
  • /24

    $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
  • /13

    $950,000

    • Land
    • 68.12 Acres
    • $13,946 per Acre

    17794 Old Frederick Rd, Mount Airy, MD 21771

    Discover one of Howard County’s rare large-acre opportunities — 68± acres of gently rolling farmland and woodland along Old Frederick Road in the Mount Airy area. With one homesite allowed, the property is protected under a county preservation easement, ensuring it will remain a beautiful, open rural landscape for generations to come. While the development rights have been sold, the easement

    Cindy Loverde Realty Concepts, Inc.

    17794 Old Frederick Rd, Mount Airy, MD 21771
  • /49

    $850,000

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

    18151 New Cut Rd, Mount Airy, MD 21771

    A rare log home retreat on 11+ peaceful acres in Mount Airy. Welcome to one of the most charming and inviting ranch-style log homes in Howard County — a true needle in a haystack set on 11 sprawling acres of serene countryside. Opportunities like this in beautiful, peaceful Howard County are few and far between.This custom-built, single-level home offers just under 1,600 sqft of thoughtfully

    Joseph McDonnell Corner House Realty

    18151 New Cut Rd, Mount Airy, MD 21771
  • /68

    $849,000

    • 3 Beds
    • 2.5 Baths
    • 2,124 Sq Ft

    16020 Fields End Ct, Woodbine, MD 21797

    Beautiful ranch-style residence offering 3 bedrooms, 2.5 bathrooms, and 2,124 finished square feet in sought-after Warfields Grants. Lush landscaping and timeless curb appeal welcome you to the open-concept main level, where hardwood floors flow from the foyer into the carpeted dining room, creating a warm and inviting first impression. The dining room opens seamlessly to the living room, where

    Bob Lucido Keller Williams Lucido Agency

    16020 Fields End Ct, Woodbine, MD 21797
  • /25

    $499,900

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft

    2440 Millers Mill Rd, Cooksville, MD 21723

    Welcome to 2440 Millers Mill Rd, Cooksville MD – a rare turnkey investment and lifestyle opportunity in the heart of Howard County. Priced at $499,900, this fully renovated and tenant-occupied colonial home offers the perfect combination of modern comfort, timeless character, and immediate rental income. Set on a picturesque 0.93-acre lot in a quiet and peaceful neighborhood, the property has

    Sibo Wang UnionPlus Realty, Inc.

    2440 Millers Mill Rd, Cooksville, MD 21723
  • /54

    $475,000

    • 4 Beds
    • 3 Baths
    • 2,928 Sq Ft

    599 Gaither Rd, Sykesville, MD 21784

    Listed significantly below market value (approximately $300k) to reflect immediate needs such as siding repair or replacement, bathroom repairs and more. This property will not qualify for conventional financing. Buyers must be prepared for cash purchase, hard money loan, or renovation loan. Located in Howard County on 5+ acres, with top rated schools, this home is waiting to be restored to its

    Zugell Jamison Cummings & Co. Realtors

    599 Gaither Rd, Sykesville, MD 21784
  • /68

    $947,500 Open Sat 12PM - 2PM

    • 6 Beds
    • 3 Baths
    • 3,218 Sq Ft

    15474 Roxbury Rd, Glenwood, MD 21738

    Escape to your own world with this stunning six-bedroom, three-full bath brick rancher nestled on a magnificent 5-acre lot, offering unparalleled amenities including an astro-turf sports field and a fenced-in, in-ground swimming pool. The main level showcases luxury living with refinished hardwood floors, fresh paint, and bright vinyl double-pane windows throughout. Highlights include a cozy

    John Burgess Samson Properties

    15474 Roxbury Rd, Glenwood, MD 21738
  • /2

    $185,000

    • Land
    • 1.06 Acres
    • $174,528 per Acre

    0 Route 144 Unit MDHW2060312, Cooksville, MD 21723

    Available vacant lot in exceptional location. 1.06 wooded acres

    Bob Lucido Keller Williams Lucido Agency

    0 Route 144 Unit MDHW2060312, Cooksville, MD 21723
  • /14

    $300,000

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

    16657 Frederick Rd, Mount Airy, MD 21771

    Bring your vision and creativity to this Mount Airy property offering endless potential! Situated on Frederick Road, this home is ready for renovation and provides a solid opportunity to restore or redesign to your taste. The property features a detached garage for parking, storage, or workshop space, along with a welcoming covered porch perfect for enjoying the outdoors. Inside, the layout

    Sarah Reynolds Keller Williams Realty

    16657 Frederick Rd, Mount Airy, MD 21771
  • /3

    $249,900

    • 1,728 Sq Ft

    15904 Frederick Rd, Lisbon, MD 21765

    OPEN CANVAS FOR INVESTORS OR SAVY HOMEBUYERS.SELLING AS -IS***TEXT LISTING AGENT FOR ACCESS*** Welcome to this unique opportunity in the heart of Lisbon, Maryland! This vacant building, zoned B1, presents a blank canvas for your creative vision, offering the flexibility to transform it into a cozy residence or a thriving commercial space. Location:Nestled in the picturesque town of

    Mario Banegas Taylor Properties

    15904 Frederick Rd, Lisbon, MD 21765
  • /5

    $350,000

    • Land
    • 1.34 Acres
    • $261,194 per Acre

    15740 Union Chapel Rd, Woodbine, MD 21797

    Rare 1 + Acre Buildable Lot in Howard County – Prime Location an area of strong supporting value homes. Tucked away in one of Howard County’s most desirable areas, this mostly level and tree studded property offers the perfect blend of privacy, natural beauty and convenience, Mature trees give you a jump start on landscaping and provide a serene backdrop for your dream home while still leaving

    Tracy Diamond EXP Realty, LLC

    15740 Union Chapel Rd, Woodbine, MD 21797
  • /10

    $450,000

    • Land
    • 1.15 Acres
    • $391,304 per Acre

    869 Morgan Station Rd, Woodbine, MD 21797

    Build Your Dream Home at 869 Morgan Station Rd, Woodbine, MD (Lot 4) -- Chapel Hill II by Catonsville Homes -- Nestled in the picturesque countryside of Howard County, this beautiful one-acre homesite at 869 Morgan Station Road offers a rare opportunity to craft a custom residence in a brand new rural community. With a builder tie-in to the award-winning Catonsville Homes, your dream of a

    Rick Cantore RE/MAX Advantage Realty

    869 Morgan Station Rd, Woodbine, MD 21797
  • /29

    $499,000

    • Land
    • 8.8 Acres
    • $56,705 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, Owner is willing to work through the permit process for this property for an extra fee.

    Holly Greenstreet Hyatt & Company Real Estate, LLC

    14459 Frederick Rd, Cooksville, MD 21723
  • /26

    $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
  • /102

    $4,500,000

    • 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-acres 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
  • /25

    $650,000

    • Land
    • 1.29 Acres
    • $503,876 per Acre

    3734 Sofia Ct, Glenwood, MD 21738

    Design & Build your own Estate Home! 1.29 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

    3734 Sofia Ct, Glenwood, MD 21738
  • /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
  • /3

    $1,849,900 New Construction

    • 4 - 5 Beds
    • 4.5 - 5.5 Baths
    • 5,740 Sq Ft

    Wellington Plan at Cattail Chase Overlook, Woodbine, MD 21797

    Williamsburg Homes Builder
    3759 Jennings Chapel Rd Unit 38521251, Woodbine, MD 21797
  • /4

    $1,789,900 New Construction

    • 4 - 5 Beds
    • 3.5 - 5.5 Baths
    • 5,305 Sq Ft

    Rutledge Plan at Cattail Chase Overlook, Woodbine, MD 21797

    Williamsburg Homes Builder
    3759 Jennings Chapel Rd Unit 38521239, Woodbine, MD 21797
  • /9

    $775,000 Open Thu 5PM - 6PM

    • 4 Beds
    • 3 Baths
    • 2,444 Sq Ft

    3211 Hayloft Ct, Woodbine, MD 21797

    Beautifully Updated 4 Bedroom, 3 Bath Home with 2-Car Garage. Welcome home to this charming and spacious residence featuring a covered front porch, inviting fireplace, and a main-level bedroom converted from living space with adjacent laundry area, adding both warmth and convenience throughout. The home has been freshly painted and features new carpet in the main-level bedroom and family room.

    Veronica Sniscak Compass

    3211 Hayloft Ct, Woodbine, MD 21797
  • /2

    $1,750,000 Coming Soon

    • 3 Beds
    • 3.5 Baths
    • 3,561 Sq Ft

    2716 Jennings Chapel Rd, Woodbine, MD 21797

    Worth the wait! This home is very special so be prepared when it comes on the market in March! Rarely does a home like this come available with almost 30 acres (most of which is fenced pasture), ride or hike directly into Patuxent River State Park, fantastic 8 stall center aisle barn with large tack room, wash stall and hay storage, riding ring and a well-maintained home. As you drive down the

    Lauren McBain RE/MAX Realty Centre, Inc.

    2716 Jennings Chapel Rd, Woodbine, MD 21797
  • /38

    $162,500

    • Land
    • 3 Acres
    • $54,167 per Acre

    2925 Route 97, Glenwood, MD 21738

    ONLINE AUCTION: Property being sold with 2935 Route 97 (MDHW2059702). Bidding begins 12/3/2025 @ 10:00 AM. Bidding ends 12/5/2025 @ 11:20 AM. List Price is Suggested Opening Bid. 3 acre lot of land. Deposit: $50,000.

    Adam Shpritz Ashland Auction Group LLC

    2925 Route 97, Glenwood, MD 21738
  • /38

    $162,500

    • 3 Beds
    • 1.5 Baths
    • 1,512 Sq Ft

    2935 Route 97, Glenwood, MD 21738

    ONLINE AUCTION: Property being sold with 2925 Route 97 (MDHW2059982). Bidding begins 12/3/2025 @ 10:00 AM. Bidding ends 12/5/2025 @ 11:20 AM. List Price is Suggested Opening Bid. 3 Story Detached Home w/Shed located in Glenwood, Maryland within Howard County. Residents can enjoy the nearby attractions such as Wester Regional Recreational Park, Howard County Fairgrounds, & Willow Spring Golf

    Adam Shpritz Ashland Auction Group LLC

    2935 Route 97, Glenwood, MD 21738
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