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$869,900
3 Beds ⋅ 4 Baths
Set on one of Woodmoor’s established, tree-lined streets, 104 Williamsburg Drive is a quintessential 1940 Colonial—one of the original generation of homes that helped define this beloved Silver Spring neighborhood. With handsome traditional architecture, gracious proportions, and a generous, corner lot (nearly 10,000 square feet) and deep yard, this 3-bedroom, 2-full- and 2-half-bath home offers something increasingly rare: the character, scale, and craftsmanship of an original Woodmoor residence. Lovingly maintained by the same owners for 25 years, the home combines timeless architecture with thoughtful updates and a comfortable, versatile floor plan. A gracious center hall opens to a spacious living room with built-in bookcases and fireplace. French doors lead to a charming den/sunroom with cathedral ceiling, custom shelving, and built-in desk—an inviting retreat for reading, working, or simply enjoying the natural light. The formal dining room features crown and chair-rail molding and a beautiful built-in cabinet. The kitchen was thoughtfully expanded to create a generous breakfast area and convenient mudroom and has been continually updated with quality appliances, including Bosch refrigerator and dishwasher. The wood floors have just been refinished, and the kitchen and other areas have been freshly painted. A convenient main level powder room is on this level as well. Original windows have been replaced with quality energy-efficient windows, and the HVAC system was replaced circa 2020. Upstairs are three generously sized bedrooms and two full baths, including a spacious primary suite with walk-in closet and en-suite bath. A second bedroom also features a walk-in closet, and all bathrooms have been updated. The lower level adds valuable living space with a large family/recreation room featuring high ceilings, fireplace, half bath, new vinyl flooring, and a separate exit to the rear yard. A spacious laundry room provides additional storage and utility space. The result is a home that feels authentically Woodmoor—comfortable, welcoming, and full of the architectural character that makes the neighborhood so enduringly appealing. Just 1½ miles from the D.C. line, Woodmoor offers exceptional convenience along with a strong sense of community. Schools, parks, trails, tennis courts, and Four Corners shopping are all nearby, including Woodmoor Bakery, Santucci’s Deli, and Four Corners Pub. Trader Joe’s, Safeway, and Whole Foods are also close by. Bus service provides easy access to the Silver Spring Metro, and the Beltway is less than a mile away. Woodmoor is supported by an active Citizens Association—not an HOA—which sponsors community traditions including the Fourth of July Parade, Woodmoorstock, and holiday tree and menorah lightings. With its mature trees, welcoming streets, distinctive homes, and convenient access to Washington, D.C., Woodmoor remains one of Silver Spring’s most cherished neighborhoods.

104 Williamsburg Dr, Silver Spring

Listing courtesy of TTR Sotheby's International Realty. Contact: chevychase@ttrsir.com
$199,990
3 Beds ⋅ 2 Baths
Rare investor opportunity in a desirable, the well-established Woodmoor neighborhood. This brick-front ranch offers a solid footprint, full basement, and excellent potential for a complete renovation. The property is in need of full updating, making it an ideal project for an investor, rehabber, or buyer looking to create value through renovation. The full basement provides additional space and potential, while the surrounding neighborhood features strong comparable sales that support the investment opportunity. Property contains mold and is being sold strictly AS-IS. Seller will make no repairs. Bring your vision and capitalize on the potential!

17518 Green Meadow Ln, Hagerstown

Listing courtesy of Taylor Properties. Contact:

$675,000
3 Beds ⋅ 2 Baths
Nestled in a serene setting in Silver Spring's sought-after Woodmoor neighborhood, this charming Colonial, built in 1946 and thoughtfully renovated top to bottom, offers a perfect blend of classic character and modern comfort. The inviting interior features three spacious bedrooms and two full bathrooms, designed with upgrades that enhance everyday living — full electrical rewiring with a new panel, complete plumbing replacement, and recessed lighting throughout. The heart of the home is a light-filled kitchen and living area, where wood floors and a fully renovated kitchen come together with brand-new stainless steel appliances, including an air-fryer range, and an existing gas line ready for future conversion. A wood-burning fireplace adds warmth to the living room, creating a perfect spot to unwind during cooler months. The fully finished walkout basement offers wonderful flexibility, complete with a kitchenette, a full bath with walk-in shower, a laundry area with a new washer and dryer, and ample storage — ideal as a cozy family room, home office, guest suite, or play area, tailored to your needs. Step outside to a freshly rebuilt, maintenance-free Trex front porch overlooking newly landscaped grounds, planted with flowering cherry trees, crab apples, and a magnolia. The true showstopper is the backyard: a rare double lot spanning over 15,760 sq ft across two parcels, descending via brick steps into a scenic wooded ravine. With no rear neighbors and no street noise, it's a private retreat perfect for outdoor entertaining, quiet evenings, or even a pool — and with architectural expansion drawings already in hand, the possibilities for a large-scale addition are real and ready to explore. Located on one of Woodmoor's quietest streets within the Montgomery Blair High School cluster, you're just minutes from the Northwest Branch Trail, Pinecrest Park, the Woodmoor Shopping Center, and easy commuter access to downtown Silver Spring and D.C. With no association fees and ample on-street parking, this home offers comfort, flexibility, and a true sense of community — a rare find in Woodmoor. Going live with photos on 9/19. Open house 9/19 and 9/20.

240 Whitmoor Ter, Silver Spring

Listing courtesy of RLAH @properties. Contact:

$625,000
4 Beds ⋅ 3 Baths
Beautifully Updated Home on an Expansive Double Parcel in Sought-After Woodmoor Welcome to 130 Whitmoor Terrace, a beautifully updated home situated in one of Silver Spring’s most desirable neighborhoods. The property offers approximately 27,321 square feet of combined land and a rare opportunity to enjoy an exceptionally spacious homesite. The home offers approximately 1,932 square feet of above-grade living space, with attractive updates throughout. Highlights include refreshed kitchen and bathroom finishes, hardwood flooring, and recently installed carpeting. The finished lower level provides additional flexible living space that can be used as a recreation room, family room, home office, fitness area, or guest space. Additional property features include updated heating and cooling systems, roofing, exterior siding, and a detached shed that offers convenient storage or potential use as a workshop, studio, or hobby space. The expansive outdoor setting provides generous room for entertaining, gardening, recreation, or simply enjoying added privacy and open space. Located in the highly sought-after Woodmoor community, the home is close to Northwest Branch Trail, Pinecrest Park, Woodmoor Shopping Center, and a variety of dining, shopping, and recreational options. Commuters will appreciate convenient access to downtown Silver Spring, Washington, D.C., and major transportation routes. Situated within the Montgomery County Public Schools system, 130 Whitmoor Terrace offers a distinctive combination of updated interiors, flexible living space, substantial land, and an established neighborhood setting. This is a rare opportunity to own a well-maintained home on an oversized double parcel in the heart of Woodmoor.

130 Whitmoor Ter, Silver Spring

Listing courtesy of Compass. Contact: (202) 386-6330
$309,900
3 Beds ⋅ 2 Baths
MOVE IN READY! Welcome to this all-brick rancher offering comfortable one-level living in a convenient location near Halfway Park and a variety of local shopping, dining, and everyday amenities. This well-maintained home features 3 bedrooms and 1½ baths, with beautiful wood floors adding warmth and character throughout the living spaces. The full unfinished basement offers excellent potential for storage, a workshop, hobby space, or future finished living area. Outside, enjoy .28 acres and the convenience of a carport for covered parking. With its classic brick exterior, practical layout, fresh updates, and convenient location, this home is a great opportunity for buyers looking for a solid, comfortable rancher close to everything they need. Schedule you tour today!

10831 Rosewood Dr, Hagerstown

Listing courtesy of The KW Collective. Contact: 3017454450
$585,000
3 Beds ⋅ 2 Baths
Coming Soon!

102 Whitmoor Ter, Silver Spring

Listing courtesy of Northrop Realty. Contact: 4104651770
$629,000
5 Beds ⋅ 2 Baths
Opportunity knocks! Rare opportunity to own a home in Woodmoor, one of the most popular places on earth to live. Minutes to DC. This 5-bedroom, 2-bath home offers a spacious layout and plenty of potential for buyers looking to add their own updates and personal touches. The home needs some work, but the possibilities are exciting for someone ready to bring their vision to life. Situated on an oversized corner lot and just steps away from Pinecrest Park, this property offers an excellent setting with added space, privacy, and no immediate homes directly behind. It’s also conveniently located near schools, making the location especially appealing. With a great lot, desirable surroundings, and plenty of potential, this is an opportunity worth taking a closer look at. Bring your ideas and make this home your own!

319 Saint Lawrence Dr, Silver Spring

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$339,999
3 Beds ⋅ 1 Baths
THIS ONE IS A SHOWSTOPPER! Cue the orchestra and dim the lights...This PlayBill is filled with ACT 1, 2 and a Grand Finale! This beautifully refreshed and renewed three bedroom, 1 full bath ALL brick rancher is ready to take center stage! This home has had a full broadway and bright lights make over. A brand new kitchen, new appliances, lighting and hardware. New windows (2016) new roof (2023). New flooring and paint throughout will make your jazz hands non optional. The new bathroom and tub will have you doing pirouettes down stage. NO HOA means no back stage drama and cue stage left, on your own time. The backyard is fully fenced and two sheds are waiting for their moment in the spotlight. The fresh landscaping and overall care, make this home what it deserves. A STANDING OVATION. Welcome to Lincoln Ave. Get your tickets before the final curtain call.

10802 Lincoln Ave, Hagerstown

Listing courtesy of Century 21 Redwood Realty. Contact: (301) 365-0664
$575,000
3 Beds ⋅ 2 Baths
Beautifully renovated and move-in ready, this charming 2-level home offers 3 spacious bedrooms and 2 full baths in a highly convenient location. Recent updates include energy-efficient windows, a newer HVAC system for excellent heating and cooling efficiency, a newer roof and gutters (November 2023), and new pressure-treated side stairs leading to a newly installed concrete landing, brand new kitchen, renovate bathrooms and much more. The finished lower level features a separate side entrance, providing additional flexibility and living space. Enjoy outdoor living in the large, fully fenced backyard—perfect for relaxing, entertaining, or enjoying your private outdoor retreat. Ideally situated with easy access to Washington, DC, the NIH, Metro bus lines, Columbia Pike (US-29), I-495, Trader Joe’s, the NW Branch Trail, and the Kemp Mill area. Combining modern updates, comfort, and an unbeatable location, this home is ready for immediate occupancy.

121 Whitmoor Ter, Silver Spring

Listing courtesy of Samson Properties. Contact: 7033788810
$659,900
4 Beds ⋅ 2 Baths
VERY nice traditional brick colonial with detached garage in the very desirable community of Woodmoor. Convenient to Virginia and D.C., lots of shopping, cultural activities and public transportation including the Metro, this lovely home boasts a cozy living room with fireplace, an adjacent bonus room which could be a den, office or even a fifth bedroom. BRAND NEW ROOF ON HOUSE AND GARAGE. The totally remodeled kitchen is sure to please. The upper level features 3 bedrooms and a full bath and the lower level has a nice finished area with egress with another full bath in addition to the utility room. There is a deck off the kitchen and den and the lot is fenced and a really nice size which offers the potential to add on to the home! Offering character, space, and a highly desirable location, Wait no more! Make this one yours!!

10511 Lorain Ave, Silver Spring

Listing courtesy of The Exchange Real Estate Company LLC. Contact: 7179310511
$1,325,000
4 Beds ⋅ 4 Baths
The city of Silver Spring has been recognized by Fortune Magazine as the #1 place to live in America! We are pleased to introduce a thoughtfully expanded and fully rebuilt luxury Colonial set in one of the city’s most desirable neighborhoods, Woodmoor. The Design Build Group, known locally for their quality craftsmanship and attention to detail has delivered a architectural restoration of exceptional scale, finish, and livability—completely turnkey and designed for modern living. Nestled in a serene, tree-lined setting near protected parkland and forest trails, the property offers a rare blend of privacy, nature, and convenience. The exterior is entirely maintenance-free, with a timeless mix of brick, Hardie siding, metal accents, and thoughtfully designed outdoor spaces including classic covered porches and a private, fenced yard. Inside, nearly 3,000 square feet of finished living space unfolds with a sense of openness and purpose. Sunlit living and dining areas are anchored by a gas fireplace and enhanced by custom millwork, while a wet bar with granite butler’s pantry creates an effortless flow for dining and entertaining. A mudroom and powder lead to a gourmet kitchen featuring quartz countertops, generous cabinetry, a large peninsula and eat-in area designed for gathering. Upstairs, four (4) well-proportioned bedrooms include a striking primary suite with cathedral ceilings, multiple closets, and a spa-inspired bath with marble vanities, soaking tub, and walk-in rain shower. A full laundry room with sink and additional full bath anchor a designer-lit hallway with closets, completing the upper level. The finished lower level adds flexible living space with a large recreation area, kitchenette, and full bath—ideal for guests, entertaining, or extended stays—with direct access to the landscaped rear yard with a stand-alone workshop/shed. Every aspect of the home reflects careful planning and high-quality execution, from the systems and materials to the lighting and smart home features. The result is a pristine, move-in-ready residence offering comfort, efficiency, and enduring classical style. All of this within the vibrant Woodmoor community, known for its strong neighborhood feel, tree-lined streets, nearby parks, and easy access to shopping, dining, and commuter routes—creating a lifestyle that is both connected and quietly refined.

10104 Big Rock Rd, Silver Spring

Listing courtesy of TTR Sotheby's International Realty. Contact: chevychase@ttrsir.com
$655,000
4 Beds ⋅ 3 Baths
Price Adjustment- A rare opportunity to own a spacious rambler in the highly sought-after Woodmoor neighborhood, offering over 2,400 square feet of living space across two expansive levels. Step inside to a welcoming entry foyer that opens into an impressive living room, large enough to accommodate a baby grand piano. This light-filled space features four front-facing windows, a wood-burning fireplace, and seamless access to both the screened porch and formal dining area, creating an ideal flow for everyday living and entertaining. The screened porch provides a peaceful retreat overlooking the side yard, perfect for morning coffee or evening relaxation. The adjacent formal dining room connects to a well-appointed kitchen featuring a skylight, center island with seating, and abundant cabinet and prep space. Down the hallway, the main level offers three bedrooms and two full bathrooms. The primary suite includes a skylight, en-suite bath, and a walk-in closet. A convenient main-level washer and dryer add to the home’s functionality. The fully finished lower level provides an additional 1,200 square feet of living space, including a large family room with a second fireplace, a generously sized fourth bedroom, a third full bathroom, and a utility room. This level also offers direct access to the attached garage, a rare and highly desirable feature in Woodmoor. With its generous layout, thoughtful features, and prime location, this home presents an exceptional opportunity to make your mark in one of Silver Spring’s most beloved communities.

9807 Merwood Ln, Silver Spring

Listing courtesy of RLAH @properties. Contact: