Colonial

4403 WINDING OAK DRIVE

OLNEY , MD 20832

MLS#: MDMC2177070

$899,900

Status: Closed
Listing number: MDMC2177070
Listing provided by: Compass
Listing agent phone: None
Last update: 5 months ago
On site: 6 months ago
Browse Properties
OATLAND FARM - Residential

Property

Beds

4

Full Baths

3

1/2 Baths

1

Year Built

2000

Sq.Footage

3,494

Pictures coming 5/1/2025 for this beautifully well maintained and updated private home backing to woods. First showings start on 5/2/2025 . Welcome to 4403 Winding Oak Drive, an exquisite residence nestled in the charming neighborhood of Olney, MD. This elegant home offers an expansive 3,494 square feet of living space, seamlessly blending style and comfort to provide a truly inviting environment. Step inside and be greeted by a grand foyer that sets the stage for the home's sophisticated interior. The open-concept design ensures fluid movement throughout, enhancing the sense of space and ease. The home's generous lot size of 12,086 square feet offers ample outdoor space for relaxation and entertainment, making it an ideal setting for hosting gatherings or enjoying quiet moments amidst nature. The lushly landscaped grounds provide a serene backdrop, enhancing the overall tranquility of the property. Conveniently located close to both DC, Northern VA and Baltimore, the ICC, 270, 495 and 95 while surrounded by parks and trails, this home offers you the best of both worlds! Please note: The tax assessor states the square footage on the house is 5,018. The floor plans state closer to just under 4,000. Sellers and Compass make no warranty as to the exact square footage of this home. Thank you OPEN HOUSE CANCELED for 5/4/25 Whether you are entertaining guests or enjoying a peaceful evening at home, the versatile living areas cater to every lifestyle need. Discover the perfect blend of elegance and functionality at 4403 Winding Oak Drive — your new haven awaits.

Features & Amenities

Interior

  • Other Interior Features

    Eat-in Kitchen, Open Floorplan

  • Total Bedrooms

    4

  • Bathrooms

    3

  • 1/2 Bathrooms

    1

  • Above Grade Finished Area

    3494.0

  • Basement YN

    YES

  • Cooling YN

    YES

  • Cooling

    Central Air, Electric

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Natural Gas, Forced Air

  • Pet friendly

    N/A

Exterior

  • Garage

    Yes

  • Garage spaces

    2

  • Construction Materials

    Vinyl Siding

  • Parking

    Garage, Driveway, Attached

  • Pool

    Yes

  • Pool Features

    None

  • Waterfront YN

    NO

  • View

    Trees/Woods

Area & Lot

  • Lot Size(acres)

    0.28

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Colonial

Price

  • Sales Price

    $899,900

  • Tax Amount

    8650.0

  • Sq. Footage

    3, 494

  • Price/SqFt

    $257

HOA

  • Association

    Yes

  • Association Fee

    $61

  • Association Fee Frequency

    Monthly

  • Association Fee Includes

    N/A

School District

  • Elementary School

    N/A

  • Middle School

    N/A

  • High School

    N/A

Property Features

  • Foundation Details

    Slab

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

Schedule a Showing

Showing scheduled successfully.

<
>
IN PERSON
VIA CHAT

What is 3 + 4 ?


Change time

Mortgage calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.

Your payment

Principal and Interest:

$

Property taxes:

$

HOA fees:

$

Total loan payment:

$

Total interest amount:

$

Location

County

MONTGOMERY

Elementary School

Middle School

High School

Listing Courtesy of Susan P Fitzpatrick , Compass

RealHub Information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. RealHub website owner shall not be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

Agent MarylandSandbox

FOUNDER

MarylandSandbox

Call Maryland today to schedule a private showing.

(980) 000-0000

maryland.sandbox@realhub365.com


* Listings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work please click here to review our DMCA policy and learn how to submit a takedown request.© 2024 FMLS.
Pictures coming 5/1/2025 for this beautifully well maintained and updated private home backing to woods. First showings start on 5/2/2025 . Welcome to 4403 Winding Oak Drive, an exquisite residence nestled in the charming neighborhood of Olney, MD. This elegant home offers an expansive 3,494 square feet of living space, seamlessly blending style and comfort to provide a truly inviting environment. Step inside and be greeted by a grand foyer that sets the stage for the home's sophisticated interior. The open-concept design ensures fluid movement throughout, enhancing the sense of space and ease. The home's generous lot size of 12,086 square feet offers ample outdoor space for relaxation and entertainment, making it an ideal setting for hosting gatherings or enjoying quiet moments amidst nature. The lushly landscaped grounds provide a serene backdrop, enhancing the overall tranquility of the property. Conveniently located close to both DC, Northern VA and Baltimore, the ICC, 270, 495 and 95 while surrounded by parks and trails, this home offers you the best of both worlds! Please note: The tax assessor states the square footage on the house is 5,018. The floor plans state closer to just under 4,000. Sellers and Compass make no warranty as to the exact square footage of this home. Thank you OPEN HOUSE CANCELED for 5/4/25 Whether you are entertaining guests or enjoying a peaceful evening at home, the versatile living areas cater to every lifestyle need. Discover the perfect blend of elegance and functionality at 4403 Winding Oak Drive — your new haven awaits.

4403 WINDING OAK DRIVE

Message successfully sent.

What would you like to know?

What is 3 + 4 ?

Related Properties

Welcome to the fantastic neighborhood of Lake Hallowell and this captivating colonial located on a choice lot backing up to green space! The centerpiece of the neighborhood is beautiful Lake Hallowell which includes a 1.5 mile walking path that loops around the lake. The community enjoys an abundance of green space and wooded areas, numerous walking paths, and features a community pool, tennis/pickleball courts, and three playgrounds. The home is highlighted by a welcoming full length covered front porch, three finished levels of living space totaling approximately 3,685 square feet, a level walk-out lower level with in-law suite which includes a kitchenette with new 2025 dishwasher, private full bathroom, two living areas that can be used as a bedroom, family room, and/or office, and an upper level primary bedroom suite with separate sitting room with gas fireplace, walk-in closet with built-ins, and upgraded private bath with new double bowl vanity and new shower. Additionally, the lower level features a second full bathroom, large recreation room with custom wet bar, and a laundry room, the main level enjoys formal living room, separate dining room, tablespace kitchen with access to a large wood deck, new stainless steel wall oven and microwave, granite tops, and breakfast bar, family room with wood-burning fireplace, remodeled powder room, and spacious foyer, the upper level has three additional bedrooms and an upgraded full bathroom. Don’t miss the large two-car garage, freshly stained deck, and paver front walkway, side walkway to rear basement door, and patio. The roof was replaced in September of 2023, driveway repaved in March 2024, water heater replaced in September of 2024, and the HVAC system replaced in 2016. The home is also conveniently located within minutes to Olney’s shopping and restaurant area, public and private schools, Med Star Montgomery Medical Center, and a short drive to the ICC highway. You are going to love making this your home and neighborhood!
#MDMC2204728

OLNEY

17715 LITTLE HAVEN LANE

5 Beds

4 Baths

3,856 Sq.Ft.

$859,000

MLS#: MDMC2204728

Tucked away on a quiet cul-de-sac in the sought-after Lake Hallowell community, 18101 Littlebrooke Drive is a stately brick colonial offering over 5,800 square feet of living space. This 7-bedroom, 5-bathroom home was thoughtfully designed for comfort and flexibility, featuring a MAIN-LEVEL BEDROOM WITH A FULL BATH—perfect for guests or multigenerational living. Upstairs, you'll find four generously sized bedrooms and THREE FULL BATHROOMS as well as the SECOND-FLOOR LAUNDRY. The fully finished walkout basement includes 2 additional bedrooms, a full bath, an expansive rec room, and 2 bonus rooms, ideal for a home office, gym, or playroom. The home boasts hardwood floors, two cozy fireplaces, and a spacious backyard perfect for entertaining or relaxing in privacy. A rare OVERSIZED 3-CAR GARAGE offers ample room for vehicles, storage, and hobbies. With easy access to community amenities like a pool, playgrounds, walking trails, and tennis courts—and just minutes from top-rated schools, parks, and Olney’s charming downtown—this home checks every box for comfort, style, and convenience.
#MDMC2203974

OLNEY

18101 LITTLEBROOKE DRIVE

7 Beds

5 Baths

5,881 Sq.Ft.

$1,000,000

MLS#: MDMC2203974

Stunning 5-Bedroom Brick Front Colonial in Brooke Manor, Olney! Welcome to this beautifully appointed Colonial home in the highly sought-after Brooke Manor community. Designed for both comfort and sophistication, this residence offers the perfect blend of style, functionality, and modern living. Step into a grand two-story foyer that opens to a bright, expansive floor plan filled with natural light. The main level features gleaming hardwood floors, vaulted ceilings, and recessed lighting throughout. A private library/home office provides a quiet retreat for work or study. The all-new gourmet kitchen is a chef’s dream, featuring elegant cabinetry, quartz countertops, a custom backsplash, stainless steel appliances, and a premium ZLINE gas range. The kitchen opens to a sunken family room accented by decorative hardwood inlays, a cozy fireplace, and direct access to a large screened porch and two rear decks overlooking a serene, tree-lined backyard — perfect for relaxing or entertaining. A formal dining room, a full bath, and a convenient main-level laundry room complete this level. Upstairs, the luxurious primary suite offers a peaceful escape with a comfortable sitting area, dual closets, and a beautifully updated spa-inspired bathroom with a dual-sink vanity. Three additional spacious bedrooms and an updated hall bath complete the upper level. The fully finished walkout basement extends your living space, featuring luxury vinyl flooring, a large recreation room, a second full kitchen, a fifth bedroom with a sitting area, and an additional den or gym — ideal for guests, extended family, or entertaining. Every detail of this home has been thoughtfully finished, including crown molding, chair rail accents, and hardwood flooring on both the main and upper levels. Freshly painted throughout with new windows and new doors, this home is move-in ready. The two-car garage with new doors provides convenience and ample storage. Perfectly located in Olney, just minutes from shopping, restaurants, parks, golf courses, and top-rated schools, with easy access to ICC-200 and Georgia Avenue. Only a short drive to Rockville Town Center and beyond! Don’t miss this rare opportunity to own a beautifully updated home in one of Olney’s most desirable communities!
#MDMC2205806

OLNEY

16702 GOOSENECK TERRACE

5 Beds

4 Baths

4,682 Sq.Ft.

$1,050,000

MLS#: MDMC2205806

Welcome to 4008 Barnsley Lane, Olney, MD Where elegance and warmth meet in perfect harmony, this fully reimagined home has been transformed with love and precision, offering a sanctuary of modern beauty and comfort. From the moment you arrive, you’ll sense the care in every detail. Step inside and be greeted by a sweeping open-concept layout, elevated by soaring ceilings and an abundance of natural light. The refinished hardwood floors stretch gracefully through the living spaces, while subtle recessed lighting highlights architectural angles and draws your eye toward the beautifully crafted finishes. At the heart of this home is the chef’s dream kitchen, a space that’s as breathtaking as it is functional. Brand-new custom cabinets rise with intention, wrapping around a generous center island that invites conversation and conviviality. Stainless steel, high-end appliances await, ready to support intimate dinners or festivities in grand style. Just beyond the kitchen, step out onto a spacious composite deck overlooking a perfectly flat, kid-friendly backyard, an ideal space for summer barbecues, playtime, or peaceful evenings under the stars. It’s a private retreat designed for connection, laughter, and lasting memories. Every room flows seamlessly into the next, each corner reflecting a thoughtful blend of timeless design and modern ease. This is more than a house, it’s a home crafted for comfort, joy, and a richly lived life.
#MDMC2201706

OLNEY

4008 BARNSLEY LANE

5 Beds

4 Baths

2,818 Sq.Ft.

$883,500

MLS#: MDMC2201706

Beautiful 4-Bedroom Colonial Backing to Woods in Desirable James Creek! Tucked away on a private drive off a quiet cul-de-sac, this stunning colonial offers the perfect blend of elegance, comfort, and privacy. Backing to serene wooded views, the home features 4 spacious bedrooms, including a luxurious primary suite with a large sitting room—a perfect retreat after a long day. Step inside to find gleaming hardwood floors throughout the main level, a grand two-story foyer, and a dramatic two-story family room with a floor-to-ceiling brick fireplace. The gourmet kitchen includes a butler’s pantry, mudroom, and plenty of cabinet space—ideal for both everyday living and entertaining. Enjoy the outdoors year-round from the screened-in porch or the deck with a peaceful wooded backdrop—perfect for relaxing or hosting gatherings. A main-level library provides a quiet space for work or study, and a large unfinished basement offers endless possibilities—ready for your finishing touches to create the perfect recreation room, gym, or guest suite. Located in the sought-after James Creek community, this home is just moments from parks, shopping. Don’t miss this rare opportunity to own a home that combines timeless charm, modern comfort, and an unbeatable location!
#MDMC2200658

OLNEY

18200 LITTLEBROOKE DRIVE

4 Beds

2 Baths

3,048 Sq.Ft.

$800,000

MLS#: MDMC2200658

Don’t miss this beautifully maintained 4-level split ( former model home/Edgewater), in the highly sought-after Olney. Ideally located on a quiet cul-de-sac/ landscaped 0.4-acre lot, which is perfect for play equipment and badminton. (You can always renovate a home but it can't be moved to a cul de sac), This approximately 3,736 sq. ft. residence, the largest model in the neighborhood, offers: 4 generous-sized bedrooms, (including a primary ensuite) and 4 updated full ceramic bathrooms: 2 full and 2 powder rooms. Most major systems have been replaced in the last 5 years: HVAC, (except compressor), Hot water heater, kitchen appliances and roof. Other features include a spacious deck, replaced windows, oversized 2-car attached garage w new My Q opener, main level family room, ( conveniently adjoining kitchen, and mud room). The mud room can be converted to a laundry room. A few steps down is a walkout recreation room (or second family room,), second powder room and large storage closet. Below is a large unfinished basement perfect for storage ( new washer and older dryer) Once inside this lovingly maintained home you'll appreciate the gleaming hardwood floors throughout the main and second levels and freshly painted interior. The home is perfect for both entertaining and everyday living. Specifically, the main level has a marble floored foyer, and 2 closets, spacious living room w large bow window (crown molding throughout the formal rooms ), separate dining room, family room w wood burning fireplace, another closet and large box window. This room adjoins the conveniently placed kitchen which features: 3 year old gas range, new microwave, new stainless steel refrigerator, double porcelain sink, ceramic backsplashes and leads to a butler's pantry and updated private ceramic powder room, (the first of two). Enjoy cooking and hosting on the expansive deck thru the side door located thru the butler's pantry. Both the deck and the lower patio overlook a pristine, private backyard. Upstairs are the 4 bedrooms, including a primary ensuite having an updated vanity area (double closet) and separate full renovated bath. In addition, there's a renovated hall bath and the 3 other bedrooms. From the main level foyer, a few steps down is the second family room or recreation room (new insulated door to the patio). On this floor, there's a conveniently located 2nd. powder room, for guests, and a large storage closet. The garage access is also located on this level. Below, is the pristine unfinished basement, perfect for extra storage (has new washer and older dryer), This is where you'll find the utility area housing the 3 year old furnace and 3 year old hot water heater. This is the one you've been waiting for: move-in condition, full of charm, and close to shopping, neighborhood parks, schools and hospital. ( Olney Mill Swim Club/ Membership optional.)
#MDMC2193642

OLNEY

18921 CLOVER HILL LANE

4 Beds

2 Baths

3,736 Sq.Ft.

$795,900

MLS#: MDMC2193642

Welcome to 17209 Sandy Knoll Drive — A Beautiful Home in the Heart of Cashell Manor! Nestled in the highly sought-after Cashell Manor community of Olney, this charming 4-bedroom, 2-full and 2-half bath colonial offers the perfect blend of space, comfort, and classic style. Set on a peaceful, tree-lined street, the home sits on a generous 0.31-acre lot in a cul-de-sac with beautiful mature landscaping and great curb appeal. Step inside to find a bright, inviting floor plan featuring hardwood floors, a spacious living room, and a formal dining area perfect for entertaining and easy access to the deck — ideal for relaxing or hosting memorable gatherings. Enjoy the cozy family room with a huge double window looking out to the front yard and a wood-burning fireplace. Upstairs, the primary suite offers ample closet space and a private bath, while three additional bedrooms provide plenty of room for family, guests, or a home office. The finished lower level adds versatility, with space for a recreation room, gym, or media area, along with extra storage. Outside, enjoy a large deck that spans almost the entire back of the home and a backyard that’s perfect for play, pets, or gardening. The home also includes a two-car garage and is part of an established neighborhood. Located within minutes of schools, local parks, and Olney’s popular shopping and dining destinations, this home combines suburban tranquility with everyday convenience.
#MDMC2205400

OLNEY

17209 SANDY KNOLL DRIVE

4 Beds

2 Baths

2,766 Sq.Ft.

$750,000

MLS#: MDMC2205400

Welcome to Olney Mill Absolutely Stunning 4-Level, 5 Bedroom, 3.5 Bath Home — Checking All the Boxes! Prepare to be impressed by this completely reinvented classic split-level home — beautifully updated to meet today’s modern lifestyle while preserving timeless craftsmanship and charm. Step into the open-concept custom island kitchen, the true heart of the home! Featuring sleek white shaker cabinetry, quartz countertops with a waterfall edge, exquisite porcelain tile backsplash, LED recessed and pendant lighting, and a stainless & glass range hood vented to the exterior — truly fit for a chef! Complete with GE stainless steel appliances, this kitchen flows seamlessly to the expansive entertaining deck and multi-level patio overlooking the fully fenced backyard. Upstairs, you’ll find four spacious bedrooms and two beautifully updated baths, including a phenomenal owner’s suite with a spa-inspired bathroom — complete with a fully custom glass-enclosed shower. The top two levels feature brand-new ¾” hardwood flooring, maintaining that warm, traditional home feel loved by so many. Head down to the family room on level three, where you can cozy up by the wood-burning fireplace, surrounded by stunning marbled porcelain tile. The full-light guest suite and adjoining guest ensuite with dual sinks and another custom shower make this space ideal for visitors — they may never want to leave! The fourth level offers an incredible fully finished game room with a wet bar, abundant cabinet storage, and a large closet for all your gear. This wide open space is perfect for a movie room, yoga studio, pool table, or your very own man cave or she shed — the possibilities are endless! Additional highlights include: Wood-look wide plank porcelain tile on the lower levels — stylish, durable, and low-maintenance LED recessed lighting and ceiling fans throughout,Storage galore with a dedicated carport storage area and backyard shed. Fun surprises! Beautiful Crown molding, chair railings, solid oak flush floor vents, exhaust lights in the bathrooms with Bluetooth speakers.....you will surely find more. Don't miss this Exceptional opportunity!!
#MDMC2205068

OLNEY

18816 STONEYHURST STREET

5 Beds

3 Baths

3,295 Sq.Ft.

$799,999

MLS#: MDMC2205068

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here