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$1,075,000
4 Beds ⋅ 3 Baths
Welcome to 8 Winding Oak Drive, a beautifully maintained Colonial nestled on a desirable corner lot in the sought-after Oatland Farm community of Olney. This elegant 4-bedroom, 2.5-bath home features an attached two-car garage, formal living and dining rooms, a butler's pantry, and a spacious primary suite complete with a private ensuite bath. Thoughtfully designed for both everyday living and entertaining, this home offers timeless charm in one of Montgomery County's most established neighborhoods. Conveniently located near parks, shopping, dining, and major commuter routes, this is an exceptional opportunity to call Olney home.

8 Winding Oak Ct, Olney

Listing courtesy of RLAH @properties. Contact: 2025188781
$1,250,000
5 Beds ⋅ 3 Baths
Nestled on more than 6.5 picturesque acres, this exceptional equestrian estate seamlessly blends timeless Cape Cod architecture with the tranquility of country living. Surrounded by beautifully landscaped grounds and scenic walking paths, the property is thoughtfully designed for both horse enthusiasts and those seeking a private retreat. Outdoor amenities include a detached two-car garage, hot tub, patio, storage shed, outdoor riding arena with sand footing, fenced pasture with paddock, and three stall shed row barn with tack room. A classic brick exterior welcomes you into an elegant interior where stunning hardwood floors and refined architectural details create an atmosphere of warmth and sophistication. The formal living room showcases soaring ceilings, crown molding, graceful arched doorways, custom built-in bookcases, and a wood-burning fireplace framed by a traditional mantel and decorative accents. Adjacent to the living room, the formal dining room is perfectly suited for both intimate gatherings and grand entertaining, featuring crown molding, chair railing, and charming built-in corner bookcases. The sunroom offers a versatile space filled with natural light, highlighted by slate flooring, exposed brick accents, and captivating views of the surrounding grounds. Designed with both beauty and function in mind, the gourmet kitchen features 42-inch cabinetry with pull-out drawers, granite countertops, stainless steel appliances, and convenient access to the mudroom with ceramic tile flooring. The main level features a spacious primary suite or guest retreat, complete with a serene neutral palette and a beautifully appointed en-suite bath adorned with timeless tile. Upstairs, a second primary suite option awaits, featuring two walk-in closets, large sun-filled windows, central vacuum, and elegant arched doorways. A generously sized secondary bedroom with a walk-in closet, hall linen closet, and full bath with ceramic tile and a tub-shower combination completes the upper level. The fully finished lower level offers exceptional flexibility for today’s lifestyle needs. A spacious recreation room, an additional bedroom with a potential walk-in closet, an office or optional fourth bedroom, a full bath, and an expansive utility and laundry room provide abundant living space. A second full kitchen further enhances the lower level, creating an ideal setup for extended guest accommodations, an au pair suite, or multigenerational living. Offering the perfect balance of luxury, privacy, and equestrian functionality, this remarkable estate enjoys convenient access to I-70, US-29, and MD-200, providing easy travel to downtown Baltimore, Washington, D.C., and destinations beyond. Transferable home warranty offered!

16510 Batchellors Forest Rd, Olney

Listing courtesy of Northrop Realty. Contact: 4105310321
$1,000,000
4 Beds ⋅ 5 Baths
Welcome to 3505 John Carroll Drive, an expansive, beautifully maintained home offering over 5,000 finished square feet of living space with 4 bedrooms, 3 full bathrooms and 2 half bathrooms. Step inside to a spacious two-story foyer with an inviting living room to the left featuring crown molding, chair rail and a charming window seat. The heart of the home is the remodeled kitchen, expanded in 2006 to create an open-concept gathering space with a dining area and sitting room equipped with a cozy wood-burning fireplace. Featuring stainless steel appliances, granite countertops, ceramic tile flooring, abundant cabinetry and fantastic natural light, this space is ideal for both everyday living and entertaining family and friends! A door off this space provides easy access to the fully rear fenced yard and patio. The stunning great room offers soaring cathedral ceilings, an impressive floor-to-ceiling brick wood-burning fireplace and access to the spacious rear deck. A main level bedroom tucked away down its own hallway with an adjacent full bath provides the perfect setup for an in-law suite, au pair quarters or private guest accommodations. A powder room completes the main level. Heading upstairs, experience a true Owner's oasis! Double doors open to a corridor that is spacious enough for a dresser and mirror, creating the perfect dressing area before entering the primary suite. This private hallway also provides access to a large walk-in closet, beautifully updated primary bathroom and laundry room (an additional washer and dryer hookup is available in the lower level). The primary bedroom features hardwood flooring and windows on three sides, filling the room with amazing natural light. Two additional bedrooms and a full bathroom are on the upper level. A loft that overlooks the family room is both functional and picturesque, featuring an entire wall of built-in shelving, the perfect spot to curl up in a chair with your favorite book and ample space for a large desk for a home office or homework station. The finished lower level provides outstanding flexibility with plenty of room for a recreation room, home gym, workshop, hobby space, or whatever combination best fits your needs. A half bath and multiple storage rooms complete this level. You can truly see this home has been well kept and cared for by the Owners with many updates and improvements throughout the years. In 1996, an addition was constructed to add the great room, loft, main level bedroom, full bathroom and basement excavation beneath the great room. In 2006, the kitchen was expanded and remodeled, the primary suite was added and a crawl space was constructed beneath the kitchen. More recent updates and improvements include: 2026 - HVAC Zone 1, 2026 – Hardwoods Refinished In Great Room & 1st Floor Hallway, 2026 – New Hardwood Flooring In Loft & Closet Room, 2026 – Fireplace Chimney Swept, 2026 – Shower Wall Tiles Replaced In Main Level Full Bath, 2026 – Luxury Vinyl Plank Floor In Main Level Half Bath, 2026 – Mirror In Main Level Half Bath, 2026 – Refrigerator, 2026 – Luxury Vinyl Plank Floor In Primary Closet & Upper Level Laundry Room, 2026 – Built-In Shelves In Loft Painted, 2026 – Exterior Light On Garage, 2026 – Exterior Doors Painted, 2026 – Interior of Garage Painted, 2024 – Roof, 2024 – Back Deck, 2024 – Interior Paint Throughout Home, 2024 – Sump Pump, 2019 – HVAC Zone 2. Minutes from great shopping, dining and entertainment! This home combines space, comfort and versatility in a beautiful neighborhood setting —book your showing today!

3505 John Carroll Dr, Olney

Listing courtesy of RE/MAX Realty Group. Contact:

$1,250,000
5 Beds ⋅ 3 Baths
Nestled on more than 6.5 picturesque acres, this exceptional equestrian estate seamlessly blends timeless Cape Cod architecture with the tranquility of country living. Surrounded by beautifully landscaped grounds and scenic walking paths, the property is thoughtfully designed for both horse enthusiasts and those seeking a private retreat. Outdoor amenities include a detached two-car garage, hot tub, patio, storage shed, outdoor riding arena with sand footing, fenced pasture with paddock, and three stall shed row barn with tack room. A classic brick exterior welcomes you into an elegant interior where stunning hardwood floors and refined architectural details create an atmosphere of warmth and sophistication. The formal living room showcases soaring ceilings, crown molding, graceful arched doorways, custom built-in bookcases, and a wood-burning fireplace framed by a traditional mantel and decorative accents. Adjacent to the living room, the formal dining room is perfectly suited for both intimate gatherings and grand entertaining, featuring crown molding, chair railing, and charming built-in corner bookcases. The sunroom offers a versatile space filled with natural light, highlighted by slate flooring, exposed brick accents, and captivating views of the surrounding grounds. Designed with both beauty and function in mind, the gourmet kitchen features 42-inch cabinetry with pull-out drawers, granite countertops, stainless steel appliances, and convenient access to the mudroom with ceramic tile flooring. The main level features a spacious primary suite or guest retreat, complete with a serene neutral palette and a beautifully appointed en-suite bath adorned with timeless tile. Upstairs, a second primary suite option awaits, featuring two walk-in closets, large sun-filled windows, central vacuum, and elegant arched doorways. A generously sized secondary bedroom with a walk-in closet, hall linen closet, and full bath with ceramic tile and a tub-shower combination completes the upper level. The fully finished lower level offers exceptional flexibility for today’s lifestyle needs. A spacious recreation room, an additional bedroom with a potential walk-in closet, an office or optional fourth bedroom, a full bath, and an expansive utility and laundry room provide abundant living space. A second full kitchen further enhances the lower level, creating an ideal setup for extended guest accommodations, an au pair suite, or multigenerational living. Offering the perfect balance of luxury, privacy, and equestrian functionality, this remarkable estate enjoys convenient access to I-70, US-29, and MD-200, providing easy travel to downtown Baltimore, Washington, D.C., and destinations beyond.

16510 Batchellors Forest Rd, Olney

Listing courtesy of Northrop Realty. Contact: 4105310321
$2,700,000
7 Beds ⋅ 9 Baths
Near the end of a quiet street in Trotters Glen, this extraordinary Toll Brothers Craftsman estate immediately commands attention with its stone-clad exterior, dual front entrances, soaring 8-foot double doors, and unmistakable architectural presence. Set on a premium wooded homesite, the home offers more than 10,700 square feet of finished living space designed for both grand entertaining and everyday comfort. Inside, rich hardwood flooring, custom millwork, tray ceilings, and a breathtaking two-story great room with exposed beam ceilings create a sense of elegance at every turn. Natural light pours through expansive walls of glass, while oversized retractable sliders seamlessly connect the family room and gourmet kitchen to the composite deck overlooking panoramic wooded views. The result is an effortless indoor-outdoor lifestyle rarely found in the area. The kitchen is designed to impress, anchored by a massive double-width island, a 48-inch built-in Monogram refrigerator, stainless steel Monogram double wall ovens, a six-burner Monogram gas range, and a butler’s pantry. The conservatory adds a stunning gathering space filled with natural light, adjoining one of two private multi-generational suites on the main level providing exceptional flexibility. The upper-level features four additional bedroom suites with private bathrooms and walk-in closets. The remarkable owner’s retreat has a sitting room, two-sided fireplace, dual boutique-style closets, and a spa-inspired bath centered around a freestanding soaking tub. The walk-out lower level extends the experience with a theater room, recreation spaces, second kitchen with bar, guest suite, patio access, and abundant storage. Conveniently located near Olney amenities, parks, golf, and MD-200, this is luxury living without compromise.

2865 Seabiscuit Dr, Olney

Listing courtesy of Bankers Real Estate Brokerage Firm LLC.. Contact:

$1,250,000
10 Beds ⋅ 4 Baths
A rare opportunity awaits with this unique property offering a total of 2.58 acres across two adjoining parcels, including the homesite and the additional lot located directly behind it. Bring your rehabbers, lovers of homes that need TLC, and all your buyers that want to fix up a home and give this one new life. Whether you're seeking extra privacy, room to expand, or exploring future investment potential, this expansive offering provides endless possibilities. The additional acreage creates a picturesque setting while offering flexibility for a variety of uses. Buyers and agents are encouraged to perform their own due diligence with the county regarding subdivision potential, permitted uses, and any future development opportunities. Bring your masks and sneakers! Please don't bring anyone into the home under the age of 18. There could be mold and microbial growth and other fun things once inside.

17036 Georgia Ave, Olney

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$1,195,000
4 Beds ⋅ 5 Baths
Gorgeous colonial in sought after Norbeck Grove ! Nestled on one of the rare premium lots backing to Rock Creek Park with wooded views and exceptional privacy. Step inside to a sun filled family room featuring soaring 2 story ceiling, a cozy gas fireplace and an abundance of windows. The spacious kitchen is complete with large island with seating, table space, and adjoining sunroom with walk out access to the patio -perfect for entertaining! Separate dining and living room offer additional gathering spaces. A private home office provides the perfect work from home space. Upstairs you will find 4 generously sized bedrooms including primary suite with expansive en-suite bathroom. The finished lower walk out level offers spacious recreation room. home gym, bonus room, and full bath. Located in beautiful Olney MD close to commuter routes, and wonderful school district. Major replacements- roof (2022) and windows (2024).

18522 Rushbrooke Dr, Olney

Listing courtesy of Samson Properties. Contact: 3018542155
$1,124,000
5 Beds ⋅ 5 Baths
Some homes are decorated. This one was designed. Set on a quiet street and lush, private lot in sought-after Olney, 4620 Brightwood Road is the personal residence of a professional designer — and it shows in every single detail. This is not a house that was styled for photos. This is a home that was built to live beautifully, every day. This jewel has 5 bedrooms, 3 full baths on the upper level, as well as a full bath on the lower floor with rear walk-up stairs to the retreat-like yard with an expansive deck. From the moment you step inside, the designer's vision is unmistakable. Warm, layered palettes. Intentional material choices. Custom finishes that most buyers spend years trying to source. Recent renovations have elevated every space — kitchens, baths, and living areas that feel simultaneously fresh and timeless. The result is a home that does something rare: it's move-in ready and move-in inspiring. Mature landscaping frames the classic exterior with its lush grass cover and beautiful trees in the oasis rear yard, while the interiors tell a far more contemporary story — one of texture, craft, and considered living. Thoughtful drapery, curated tile, elevated fixtures, and a cohesive design language that flows from room to room without a single false note. Located in one of Montgomery County's most desirable communities, with top-rated schools, easy access to major commuter routes, and the charm of a neighborhood that actually feels like one. Opportunities like this don't come along often. When a designer sells their own home, the market should pay attention. UPDATES 2020/2021 & ADDITIONAL FEATURES: Rich herringbone flooring in the family room and upper hallway Wood kitchen cabinetryRaised the height of main level doors Mud room has washer/dryer hookup (owner moved to lower level) Gas fireplace - cleaned, new tile and mantle Primary bath renovated with marble and high-end materials Connected bathroom on upper level has bluetooth in lights Custom closets throughout Custom Plantation shutters throughout Walk-up stairs excavated to back yard from lower level Water softener added New windows 2-Zone HVAC (approximately 2017 by previous owners) Oversized gutters Landscape lighting and golf-course envy lush grass Garage door replaced and driveway renovated Roof/HVAC replaced 2017 by previous owners

4620 Brightwood Rd, Olney

Listing courtesy of Compass. Contact: (240) 219-2422
$1,125,000
4 Beds ⋅ 4 Baths
Elegant, Light-Filled Home in Sought-After Barnsley Manor. Welcome to the perfect blend of space, comfort, and modern updates in one of Olney's most desirable neighborhoods. Whether you're hosting family and friends or looking for the ideal place to grow, this beautifully maintained home offers an exceptional lifestyle in the peaceful community of Barnsley Manor. From the moment you step inside, you're greeted by a dramatic two-story foyer and gorgeous new luxury vinyl plank flooring that flows throughout the main living areas. Sunlight pours into the home, highlighting the spacious formal living and dining rooms, perfect for entertaining or everyday gatherings. At the heart of the home is an inviting family room featuring a cozy wood-burning fireplace and a breathtaking wall of windows that fills the space with natural light. All original windows have been replaced with low-maintenance vinyl-clad windows, providing lasting beauty without the upkeep. The updated kitchen is designed to impress, offering quartz countertops, refreshed cabinetry, a large center island with seating, abundant storage, a generous pantry, and ample space for casual dining. Step outside through the sliding glass doors to enjoy the beautifully hardscaped patio overlooking a private, fenced backyard—ideal for outdoor entertaining, grilling, or relaxing. The main level also features a private home office, convenient powder room, and a spacious laundry/mudroom with access to the oversized two-car garage. A custom four-foot bump-out enhances both the garage and the luxurious primary suite above, adding valuable living and storage space. Upstairs, the expansive primary retreat offers soaring cathedral ceilings, room for a sitting area, two walk-in closets, and a spa-inspired ensuite complete with dual vanities, a soaking tub, separate shower, and dressing area. A second bedroom enjoys its own private bath, while two additional bedrooms share a Jack-and-Jill bathroom. Every bedroom includes a walk-in closet, providing exceptional storage throughout. The enormous walk-up lower level is ready for your vision, featuring a rough-in for a full bathroom, abundant storage, and endless possibilities for additional living space, a recreation room, home gym, or media room. Recent Updates Include: · New luxury vinyl plank flooring · Fresh interior paint · Updated kitchen · Updated bathrooms · New front walkway · Replacement vinyl-clad windows throughout Residents of Barnsley Manor enjoy outstanding community amenities, including walking trails, a playground, tennis and pickleball courts, basketball courts, neighborhood events, and a community pool. Conveniently located just minutes from Olney's shopping, dining, parks, and both public and private schools, this home offers the perfect balance of tranquility and accessibility. Beautifully updated, thoughtfully designed, and ideally located—this exceptional home truly has it all. Don't miss your opportunity to make it yours! NO FRONT FOOT BENEFIT FEE

5019 Tothill, Olney

Listing courtesy of Weichert, REALTORS. Contact:

$1,390,000
This unique property is currently used as both a medical office and a residence. Located off the main road in Olney, MD, it offers excellent business exposure. Additionally, the property is situated between two other Special Exception properties: a veterinary office and an assisted living facility. It is also located just a quarter mile from MedStar Hospital, making it especially attractive as a healthcare office. The property offers a truly special and serene atmosphere, serving as both a primary residence and a healthcare office—currently home to a chiropractor. Situated on one acre of land in central Olney, it is nestled in a thriving community along the well-traveled Route 108. The primary residence spans approximately 3,526 square feet and includes four bedrooms and four bathrooms. The office portion of the property offers an additional 1,710 square feet. The home features a 2-car garage, a family room, a living room, a formal dining room, and ample outdoor space for entertainment. There is also plenty of parking available for visitors. The property consists of two wings built in 1945 and 1993, respectively. While zoned as residential, it offers great potential for conversion into various property types by right, including a Bed & Breakfast, embassy, residential care facility, house of worship, and several other options. Permitted uses by right include: Bed & Breakfast One-family detached dwelling unit Embassy Farm tenant dwelling/mobile home Small group home Mobile home (permanently attached) Public utility buildings or other public uses Adult foster care home Residential care facilities (up to 8 persons) Ambulance/rescue squad/fire station Childcare facility Houses of worship Opportunity housing projects Libraries/museums Parks/playgrounds Agricultural uses/farm market

2701 Olney Sandy Spring Rd, Olney

Listing courtesy of TTR Sotheby's International Realty. Contact: chevychase@ttrsir.com
$1,200,000
Rare Development Opportunity in Prime Olney Residential Location! This unique offering includes both an R200-zoned parcel of land and a charming Cape Cod-style home, providing an ideal investment/development opportunity. Together, these parcels—one with a single-family home & Detached Garage built in 1957 and the other as additional land—offer a total of 2.98 acres (1.5 acres + 1.48 acres) potential for 5 total lot subdivision. Existing Home Features: Living Space: 1,818 sq. ft. above grade, Unfinished Basement:1,511 sq. ft. with mechanical storage and laundry area, Bedrooms: 4 total (2 on the main level, 2 on the upper level) Bathrooms: 2 full bathrooms (one on each level) Additional Spaces: Living room, dining room, family room, and an enclosed rear porch Side Porch & Deck (decking requires replacement; please exercise caution when viewing) Detached two-car garage for added convenience, Brick and vinyl siding, Gutters & Downspouts: Aluminum, Windows: Metal double-hung. HOME & LAND SOLD STRICTLY "AS IS" Public water and sewer is on the street, buyer is responsible for any further future development process & utilities connections fees associated with the purchase . Don't miss this opportunity to invest in a versatile property in a desirable Olney location! Cross listed in Residential Bright id # MDMC2155786 FIRST OPEN HOUSE 11/17/24 12-2PM.

Briars Rd, Olney

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,200,000
4 Beds ⋅ 2 Baths
Rare Development Opportunity in Prime Olney Residential Location! This unique offering includes both an R200-zoned parcel of land and a charming Cape Cod-style home, providing an ideal investment/development opportunity. Together, these parcels—one with a single-family home & Detached Garage built in 1957 and the other as additional land—offer a total of 2.98 acres (1.5 acres + 1.48 acres) potential for 5 total lot subdivision. Existing Home Features: Living Space: 1,818 sq. ft. above grade, Unfinished Basement:1,511 sq. ft. with mechanical storage and laundry area, Bedrooms: 4 total (2 on the main level, 2 on the upper level) Bathrooms: 2 full bathrooms (one on each level) Additional Spaces: Living room, dining room, family room, and an enclosed rear porch Side Porch & Deck (decking requires replacement; please exercise caution when viewing) Detached two-car garage for added convenience, Brick and vinyl siding, Gutters & Downspouts: Aluminum, Windows: Metal double-hung. HOME & LAND SOLD STRICTLY "AS IS" Public water and sewer is on the street, buyer is responsible for any further future development process & utilities connections fees associated with the purchase . Don't miss this opportunity to invest in a versatile property in a desirable Olney location! Cross listed in Land Bright id #MDMC2155798 Additional parcel Tax ID #160800707723 conveys

4201 Briars Rd, Olney

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: