City/Oakwood Homes with Detached Garage

Welcome to the charming subdivision of City/Oakwood, nestled in the heart of Oakwood, Montgomery County, Ohio. This idyllic community offers a perfect blend of tranquility and convenience, making it a sought-after location for homebuyers.

One of the standout features of the homes in City/Oakwood is the detached garage option. Whether you're looking for extra storage space, a workshop area, or simply prefer the aesthetic appeal of a detached garage, these homes cater to your needs.

Living in City/Oakwood means enjoying a peaceful suburban lifestyle while being just a stone's throw away from urban amenities. With tree-lined streets, well-manicured lawns, and a strong sense of community, this subdivision provides an ideal setting for families, professionals, and retirees alike.

Residents of City/Oakwood have easy access to top-rated schools, parks, shopping centers, and dining options, ensuring that everything you need is within reach. The real estate market in City/Oakwood offers a variety of housing options, from cozy bungalows to spacious family homes, ensuring there's something for everyone.

If you're looking for a place to call home that combines small-town charm with modern conveniences, look no further than City/Oakwood in Oakwood, Ohio. Come and discover the beauty and tranquility that this subdivision has to offer – your dream home awaits!

Newest City/Oakwood Homes with Detached Garage

$369,900

3 Beds ⋅ 2 Baths ⋅ 965067 MLS ⋅ Katie Slone

Welcome home to this charming 3-bedroom, 1.5-bath brick home in the heart of Oakwood! Filled with character and thoughtful updates, this home beautifully blends timeless details with a fresh, modern feel. Step inside to gorgeous hardwood floors, arched doorways, crown molding and a stunning stone fireplace that serves as the centerpiece of the inviting living room. The bright dining room features beautiful built-ins and flows into the updated kitchen with tons of cabinetry, stainless steel appliances and a subway tile backsplash. An additional natural light-filled living space off the back of the home offers plenty of flexibility for a family room, playroom or entertaining space, with sliding doors leading directly to the backyard. Upstairs you’ll find three bedrooms with hardwood floors and an updated full bath. The home also features an unfinished basement with laundry and storage, and a 2-car detached garage. Outside, enjoy a fenced backyard with patio space perfect for relaxing or entertaining. Full of charm, character and modern touches, this adorable Oakwood home is ready for its next owner!

320 Claranna Avenue, Oakwood

Courtesy of Katie Slone and Howard Hanna Real Estate Serv

$695,000

5 Beds ⋅ 4 Baths ⋅ 963147 MLS ⋅ Cynthia A Buckreus

Welcome to this classic Oakwood home, lovingly maintained by its long-time owners and brimming with timeless character and charm. Ideally located within walking distance of schools, the park, the community center, and Ashley's Pastry Shop, this exceptional home offers the perfect blend of historic elegance and modern comfort. A charming brick walkway leads to the inviting covered front porch—an ideal spot to enjoy your morning coffee or unwind at the end of the day. Offering approximately 3,600 square feet of living space, the home showcases gorgeous original hardwood floors, a sweeping staircase, rich woodwork, elegant wainscoting, and crown molding throughout. The welcoming foyer is flanked by a spacious living room with a beautiful fireplace and a formal dining room, creating an ideal setting for both everyday living and entertaining. A bright sunroom, surrounded by walls of windows, provides the perfect space for a home office, den, or reading room. French doors from the main living areas create a seamless flow to the outdoors. The updated eat-in kitchen features a center island, granite, abundant cabinetry, and a convenient butler's pantry with a sink that connects directly to the dining room—perfect for hosting gatherings. Just off the kitchen, the family room addition offers new carpet. A half bath is tucked away. Upstairs, the spacious primary suite includes generous closets and an en suite bath. Two additional bedrooms and an updated full bathroom complete the second level. The finished third floor adds incredible flexibility with two more bedrooms featuring new carpet and a full bathroom. Outside, enjoy the beautifully landscaped yard and stamped concrete patio + a detached two-car garage completes this exceptional home. Filled with warmth and character, this classic Oakwood home is ready to welcome its next owners.

145 Wisteria Drive, Oakwood

Courtesy of Cynthia A Buckreus and Coldwell Banker Heritage

$414,900

4 Beds ⋅ 3 Baths ⋅ 963250 MLS ⋅ Jamie Curtis

Experience contemporary, energy-efficient living in this beautifully renovated home, where timeless character meets modern design. A substantial interior renovation transformed the home with major mechanical and structural upgrades, creating a move-in-ready property with exceptional quality and peace of mind. The thoughtfully redesigned floor plan features four bedrooms, 2.5 bathrooms, a dedicated home office, and a semi-finished basement, offering flexible living space. At the heart of the home is the stunning open-concept living and dining area anchored by the kitchen featuring an oversized quartz island, custom cabinetry, and stainless steel appliances. The main level also offers a bedroom, a full bath, a convenient half bath, office space, and a redesigned staircase that enhances the home's flow. Upstairs, raised vaulted ceilings create an airy feel throughout the three additional bedrooms and full bathroom, while newer windows fill the space with abundant natural light. Extensive improvements completed during the renovation include reinforced structural framing, engineered hardwood flooring throughout, solid wood three-panel doors, upgraded insulation, fresh drywall and paint, all-new electrical wiring with upgraded service and breaker panels, new plumbing supply and drain lines, an energy-efficient HVAC system, and a heat pump water heater. A security system with remote monitoring capability adds an additional layer of convenience and peace of mind. Outside, the deck, fencing, and yard provide a wonderful opportunity for the next owner to customize and create their own outdoor retreat while enjoying the confidence that the home's major interior improvements have already been completed.

346 Corona Avenue, Oakwood

Courtesy of Jamie Curtis and BHHS Professional Realty

$390,000

3 Beds ⋅ 2 Baths ⋅ 960648 MLS ⋅ Timothy A Williams

Discover a harmonious blend of classic charm and modern living at this delightful Oakwood residence, where inviting curb appeal and thoughtful design create an immediate sense of home. This two-story property offers 1906 square feet of comfortable living space, featuring three bedrooms and one and a half bathrooms. The welcoming front porch, adorned with classic columns, sets a serene tone amidst landscaped greenery and mature trees, inviting peaceful moments outdoors. Inside, the living area boasts gleaming hardwood floors and a classic brick fireplace, providing a cozy focal point for relaxation. Abundant natural light illuminates this adaptable space, further enhanced by built-in shelving. The contemporary kitchen is a chef's delight, equipped with sleek granite countertops, a practical kitchen island, and stainless steel appliances including a dishwasher, microwave, range, and refrigerator. Recessed lighting and tile flooring complete this bright and functional space. Bedrooms offer comfort and tranquility, with options featuring plush carpeting or warm hardwood floors, and ceiling fans for optimal airflow. The main level seamlessly connects the kitchen to the living area, promoting an open and engaging environment. An unfinished basement provides ample utility space, laundry facilities with a dryer, and extensive storage or potential for a workshop. The property's exterior features maintenance free vinyl siding, complemented by a detached garage. A charming brick patio offers a private outdoor retreat, perfect for entertaining or quiet contemplation. Located in a desirable neighborhood with sidewalks and mature trees, this home offers both privacy and community appeal.

241 Orchard Drive, Oakwood

Courtesy of Timothy A Williams and Glasshouse Realty Group

$335,000

3 Beds ⋅ 2 Baths ⋅ 961475 MLS ⋅ Toni Donato Shade

Oakwood charm meets move-in ready perfection at 406 East Drive. From the moment you step onto the covered front porch, you'll feel right at home. Inside, hardwood floors and updated windows set a warm, bright tone throughout the home. Kitchen is fully functional with eat in dining space. But if you enjoy formal dining the you’ll love the spacious dining room. The bright and airy finished basement adds valuable and cozy living space. Three generous sized bedrooms and tastefully updated full bath complete the 2nd floor. Outdoors, the paver patio is the perfect spot to unwind or host. Impeccably cared for and ready for its next chapter — don't miss this one.

406 East Drive, Oakwood

Courtesy of Toni Donato Shade and Coldwell Banker Heritage

$319,900

3 Beds ⋅ 2 Baths ⋅ 960775 MLS ⋅ Jerry E Williams

Discover this timeless residence nestled in the desirable Oakwood neighborhood and within the Oakwood School District! Offering both classic charm and modern comforts, this captivating two-story home features three bedrooms and one and a half baths; and it includes 1482 square feet of living space plus 442 sq ft for a full, (semi) finished basement (assessor data). A Detached Two-Car Garage and Driveway provide very convenient Off-Steet Parking and additional storage. A welcoming screened front porch invites serene outdoor relaxation, perfect for enjoying tranquil afternoons. Inside, the home boasts rich hardwood flooring throughout the main living areas, complemented by abundant natural light that creates an inviting atmosphere. The living room is a focal point, enhanced by a faux fireplace and elegant built-in cabinetry; a stylish chandelier illuminates the dining space. The kitchen features sleek countertops, stainless appliances including a range, dishwasher, and refrigerator, and a functional layout ensuring meal preparation is a breeze. A quaint office/flex space is tucked away. Upstairs, each bedroom offers generous windows, warm hardwood floors, and ceiling fans, providing comfortable and naturally lit retreats. The property also includes a versatile basement, presenting excellent opportunities for future customization. Step outside to a spacious wooden deck with a pergola, ideal for entertaining guests or simply unwinding in your private backyard. Located on a 0.15-acre lot, this residence offers a harmonious blend of classic elegance and practical living in a vibrant community. Convenient to Shopping, dining, parks and more!

242 Lonsdale Avenue, Oakwood

Courtesy of Jerry E Williams and Wright-Patt Realty, Inc.

$850,000

4 Beds ⋅ 5 Baths ⋅ 960407 MLS ⋅ Kamela Kordik

Set on two separately deeded (PID Q71-01005-0020 & Q71-01005-0021), beautifully landscaped lots , on one of Oakwood's most inviting streets, this brick home blends the character of its 1925 origins with top-to-bottom updates that make it feel entirely current. All wood floors were just refinished and many rooms have fresh paint. Inside, the completely reimagined kitchen is the centerpiece — custom in every detail, designed for both daily living and entertaining. The owner's suite opens onto a covered balcony with custom spiral stairway leading to the rear yard and features an elegant dressing room with custom built-ins alongside a fully updated bathroom; a level of finish rarely found. The Pella replacement windows throughout the main house and new custom insulated arched windows in the sunroom bring in natural light while keeping the home's classic exterior profile intact. Four bedrooms and 2 full and 3 half bathrooms offer generous room across aprox. 3194 square feet above grade, with a finished basement providing additional flexible space. A gas log fireplace anchors the main living area with warmth and presence, while French doors connect it to both the sunroom, the rear porch and yard. Step outside to an expansive covered rear porch that overlooks a stone and granite outdoor kitchen — a thoughtfully built extension of the entertaining space, that includes, a pizza oven, built in grill, cook top refrigerator and a wood burning fireplace — surrounded by mature landscaping on a lot that stands out even in this neighborhood. A detached two-car garage, with built-in stairs to a second-floor storage area, completes the picture. A Generac whole house generator, keeps the entire house and garage running during any potential power outages. Safe in basement conveys. Located just a couple of blocks from the shops of Oakwood and dining along Far Hills Avenue, this is a home worth seeing in person. Listing agent is the owner

24 Monteray Road, Oakwood

Courtesy of Kamela Kordik and Kamela & Company Realty

$715,000

5 Beds ⋅ 4 Baths ⋅ 954415 MLS ⋅ Emily Pelligra

Situated on one of Oakwood’s most coveted tree-lined streets, this stately Colonial offers timeless elegance, refined updates, and an exceptional location adjacent to Harman Elementary and just one block from Smith Gardens. Boasting over 3,200 square feet, five bedrooms, and four beautifully updated bathrooms, this remarkable residence seamlessly blends classic charm with modern luxury. A welcoming entry introduces hardwood floors, soaring ceilings, and the formal living room features a stunning custom fireplace with an elegant wood mantel and built-in bookcases, creating a warm yet sophisticated gathering space. The expansive formal dining room showcases distinctive built-ins, stylish pendant lighting, and French doors that seamlessly connect to the family room. Filled with natural light, the spacious family room opens directly to the rear patio, creating effortless indoor-outdoor living and entertaining. Designed for both everyday comfort and elevated entertaining, the chef’s kitchen is beautifully appointed with granite countertops, custom cabinetry, a Viking range, center island with seating and prep sink, and a dedicated beverage center. The second level offers four spacious bedrooms and three fully updated bathrooms featuring modern finishes and designer vanities. The luxurious primary suite serves as a private retreat with a generous walk-in closet and beautifully appointed en suite bath. The remodeled third level provides exceptional privacy and flexibility, ideal as a fifth bedroom, guest suite, home office, or bonus living space, complete with a convenient second laundry area. The walk-out lower level offers abundant storage and additional laundry space. Both washers and dryers along with the basement freezer, will convey. Outdoor living is equally impressive with a beautifully designed paver patio, expansive backyard, detached two-car garage, and additional parking pad. A rare opportunity to own a distinguished Oakwood residence!

712 Oakwood Avenue, Oakwood

Courtesy of Emily Pelligra and Coldwell Banker Heritage

$279,900

3 Beds ⋅ 2 Baths ⋅ 954666 MLS ⋅ Marisa Murrow

Back on the market due to buyer's financing falling through! You'll find all the historic Oakwood charm you'd expect in this 3 bedroom, 1.5 bath home in the heart of town! From the moment you step inside, there's an unmistakable feeling of home. The warmth of the original hardwood floors, the craftsmanship of custom built-ins and the inviting fireplace create a sense of comfort. The main floor offers a classic layout with a cozy living room, featuring built-in shelves and a beautiful fireplace. The spacious dining room is perfect for gatherings, with a bonus room off the back that could easily serve as a home office or workout space, complete with half bath. Thoughtful updates include a refreshed kitchen where soft-close cabinets and a dishwasher were added while preserving the vintage farmhouse sink. Sip your morning coffee or enjoy sunsets on the peaceful covered front porch! Follow the turned wooden staircase upstairs, to discover 3 bedrooms with even more custom, old world storage. Tucked away like a secret retreat, the sleeping porch in this historic home is located on the north side, off one of the bedrooms. Perfect for cozying up with a book or savoring a glass of wine on a cool summer evening, this is sure to be your new favorite hideaway! The additions of a new furnace (2025), newer tankless water heater (2021) and opener on the oversized garage door (2025) make this home as functional as it is charming! With a fully fenced backyard and spacious deck for relaxing or entertaining, this home offers the ideal setting for comfort, privacy and outdoor enjoyment! VA assumable loan at 2.75%!!

303 Hadley Avenue, Oakwood

Courtesy of Marisa Murrow and Keller Williams Community Part

$539,000

4 Beds ⋅ 3 Baths ⋅ 952777 MLS ⋅ Joanne Cronin

Picture perfect home on a boulevard, in an Oakwood "sweet spot"close to schools, library, and the Oakwood Community Center. This home was lovingly owned & updated for over 63 years. Originally a 3 bedroom, a two story addition in 1975 (approximately) converted it into a 4 bedroom adding another full and 1/2 bath. Property spans approximately 3300 sq ft. including the unfinished basement. Charming front porch with brick pavers greet you as you enter the formal living room with fireplace focal point. Spacious dining room built in cabinets. Both rooms access the fully equipped eat-in kitchen. The kitchen is centrally located between dining/living and family room and accesses the full unfinished basement. The family room is impressive with wood burning fireplace, south & west windows providing natural light, a half bath, large coat closet and access to rear yard. Second floor boasts four bedrooms - one is primary with designated full bath. Three other bedrooms offer plenty of closet space and share a full bath. Two of the original bedrooms were converted into one and was used as an office/craft room. Wall could be restored and home could easily converted to a five bedroom home! This home will exceed your expectations. Schedule your showing today.

24 Greenmount Boulevard, Oakwood

Courtesy of Joanne Cronin and Irongate Inc.

$399,900

3 Beds ⋅ 3 Baths ⋅ 953596 MLS ⋅ Jill Aldineh

Welcome to this charming Oakwood beauty, ideally situated near UD and the vibrant downtown, and within a short distance of a cozy coffee shop and a variety of dining options. This home features an inviting front porch, perfect for relaxing afternoons. Inside the porch, discover beautiful hardwood floors and a welcoming entry that leads to a bright living room seamlessly connected to a spacious dining room ideal for large gatherings. A bonus sunroom offers a delightful space for reading or a serene home office. The character-filled kitchen is highlighted by a built-in breakfast nook, perfect for casual meals. The second level features three bedrooms, including a generously sized primary bedroom with dual closets. The hall bathroom has been tastefully updated, enhancing this home’s lovely appeal. Additionally, a walk-up attic presents the possibility for a fourth bedroom, providing extra space for your needs. Brand new roof with full tear-off (2026). This enchanting home is ready and waiting for its new owners to make it their own.

506 Volusia Avenue, Oakwood

Courtesy of Jill Aldineh and RE/MAX Victory + Affiliates

Start Your Search

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of the Dayton Area Board of Realtors® MLS IDX Database. Real estate listings from the Dayton Area Board of Realtors® MLS IDX Database held by brokerage firms other than Real Estate Company are marked with the IDX logo and are provided by the Dayton Area Board of Realtors® MLS IDX Database. Information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in. Copyright© 2026 Dayton Area Board of Realtors®