Oakwood Homes with Detached Garage

Welcome to Oakwood, Ohio—a charming city nestled within Montgomery County that beautifully balances suburban tranquility with urban convenience. Known for its tree-lined streets, friendly neighborhoods, and a strong sense of community, Oakwood offers residents a delightful lifestyle enriched by a variety of amenities, parks, and local events.

One of the standout features of homes in Oakwood is the abundance of properties boasting detached garages. These versatile spaces provide not only shelter for your vehicles but also serve as perfect workshops, storage areas, or creative studios. Imagine having a dedicated space just steps away from your home where you can pursue hobbies, work on projects, or simply have extra room for your belongings.

The architectural charm of Oakwood homes, paired with the practicality of detached garages, makes this city an attractive option for families, professionals, and retirees alike. With a strong emphasis on education, Oakwood is home to top-rated schools and a welcoming community that hosts various events throughout the year, fostering connections among residents.

Additionally, Oakwood's proximity to Dayton allows for easy access to a plethora of dining, shopping, and entertainment options, while still preserving the peaceful atmosphere that makes this city so special. Whether you're looking to buy your first home or seeking a tranquil place to retire, Oakwood offers a unique blend of comfort and convenience that is hard to resist. Come explore the inviting charm of Oakwood and discover your dream home with a detached garage today!

Newest Oakwood Homes with Detached Garage

$629,900

4 Beds ⋅ 4 Baths ⋅ 964618 MLS ⋅ Emily Pelligra

Welcome to this exceptional 1916 Craftsman, meticulously maintained and thoughtfully updated to blend historic character with today's modern conveniences. An Oakwood treasure, this home sits on one of the community's most desirable tree-lined streets, just minutes from parks, restaurants, schools, and major highways. The expansive covered front porch provides a welcoming place to relax and leads to an impressive foyer which introduces the home's warmth and craftsmanship. The elegant living room features striking Palladian windows, exposed ceiling beams, a beautiful fireplace, and French doors opening to both the front porch and rear patio. Bathed in natural light, the gracious dining room is perfect for gatherings, with a fireplace and glass doors opening to the porch. The spacious kitchen offers abundant cabinetry, generous workspace, and newer appliances. The family room features custom built-ins, a whole-home speaker system, and access to the private backyard. Hardwood floors extend throughout the main and second levels, complemented by a mudroom and first-floor powder room. Upstairs, the expansive primary suite offers generous closet space and a luxurious en suite bath with heated floors, soaking tub, separate shower, and dual vanity. Three additional spacious bedrooms, two full baths, and a second-floor laundry room provide exceptional convenience. The unfinished attic offers abundant storage, while the bright walk-out basement with high ceilings, plentiful windows, and a half bath (toilet only) provides potential for additional living space. An original carriage garage offers storage for lawn equipment, while the oversized two-car garage easily accommodates larger vehicles. Professionally landscaped grounds and exterior lighting complete this remarkable property. A rare opportunity to own one of Oakwood's distinguished historic homes, where timeless craftsmanship and thoughtfully integrated modern amenities create an exceptional place to call home.

254 Schenck Avenue, Oakwood

Courtesy of Emily Pelligra and Coldwell Banker Heritage

$304,000

2 Beds ⋅ 2 Baths ⋅ 965272 MLS ⋅ Teresa M Gustafson

Charming Oakwood Bungalow with Timeless Character & Valuable Updates Welcome home to this classic Oakwood bungalow, where historic charm meets modern peace of mind. Thoughtfully designed to maximize every square foot, the finished lower level significantly expands the living space, offering endless possibilities for a family room, home office, workout area, or guest retreat. The home features two generously sized bedrooms and two full bathrooms a rare convenience for a home of this era. Relax on the inviting front porch and enjoy the charm of this tree-lined Oakwood neighborhood. Inside, you'll appreciate the original hardwood floors, rich woodwork, and charming kitchen with abundant cabinetry, stainless steel appliances, and an adjoining dining room that's perfect for everyday meals or entertaining. Step outside to a fully fenced backyard with plenty of space to relax, entertain, or let pets play, plus an oversized detached garage with alley access and additional storage. Major improvements include custom replacement windows (2018) that preserve the home's original character, a new roof (2024), and a professionally installed interior drainage system by Concrete Pro (June 2026) with a lifetime transferable warranty. The finished basement was also refreshed in July 2026 with new waterproof luxury vinyl plank flooring and fresh paint. Conveniently located near parks, shopping, restaurants, and the Fraze Pavilion, this move-in-ready home offers the perfect combination of character, functionality, and lasting value.

344 Hadley Avenue, Oakwood

Courtesy of Teresa M Gustafson and Glasshouse Realty Group

$255,000

2 Beds ⋅ 1 Baths ⋅ 965199 MLS ⋅ Jennifer Blackburn

Welcome to this charming Oakwood bungalow home that sits perfectly on an eye-catching corner lot! Surrounded by professional landscaping and mature trees, you will be sure to appreciate the character of this home. Featuring sanded original hardwood flooring, two bedrooms and a remodeled bathroom with stunning high temperature fired 17 inch Spanish tile sprawling from floor to ceiling! The kitchen needs updated but is functional and new hard wood flooring for the kitchen is on site. The freshly painted basement extends under the entire house and front porch, making it a great flex space for entertainment, play area and additional storage. The entire plumbing of the home is copper with extensive isolating ball valves and all weather outdoor faucets. The drain lines and the water heater have all been updated within the last three years. A new water line from the street connection was installed in 2023. A new 200 amp electrical supply and beaker box has been installed that service the washer/dryer and a few other lines have been connected. A new 6 inch guttering system was just installed - 2026. Enjoy morning coffee over looking the beautiful tulip tree on the large, covered front porch or entertain on the back paved patio. Two fruit bearing peach trees (white & yellow) are planted in the Hathaway tree lawn. The back yard is sheltered from the sidewalk with well maintained trees and bushes, while the newly planted Arborvitae trees, provide you with the privacy that you have always desired. The detached two car garage provides extra storage and peace of mind. This well maintained home is ideally located just blocks from the Oakwood Club, Dorothy Lane Market, and the Shops of Oakwood. The property is being sold as-is but has been well taken care of. Don’t miss your chance to make your dream a reality.

301 Monteray Avenue, Oakwood

Courtesy of Jennifer Blackburn and Agora Realty Group

$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

$450,000

4 Beds ⋅ 3 Baths ⋅ 964996 MLS ⋅ Toni Donato Shade

Tucked into Oakwood's coveted Schantz Park Historic District — a National Register neighborhood laid out by industrialist Adam Schantz Jr. and landscaped by the Olmsted Brothers of Central Park fame — this 1916 Craftsman carries a century of character with modern ease. Rich original woodwork, gleaming hardwood floors, beamed ceilings, and a substantial wood-burning fireplace anchor the living spaces, echoing the craftsmanship that made this district famous. The kitchen has been thoughtfully reimagined with granite counters, cherry cabinetry, tile backsplash, and stainless appliances, while a two-story addition adds a generous main-level family/media room the original architects never imagined. Unwind on the screened patio, a shaded retreat for morning coffee or evening gatherings. Four bedrooms, 2.5 baths, and roughly 2,258 square feet of storied living. Ideally located within walking distance of the University of Dayton and the Brown Street shops and restaurants, and just minutes from area hospitals, Wright-Patterson AFB, Downtown Dayton and more. Some addresses aren't just built, they're inherited.

6 Glendora Avenue, Oakwood

Courtesy of Toni Donato Shade and Coldwell Banker Heritage

$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

$215,000

3 Beds ⋅ 1 Baths ⋅ 964352 MLS ⋅ Kathy A Winter

Discover timeless charm and remarkable potential at this delightful brick residence in the sought after Oakwood Community. This inviting home, boasts a great location just steps from Orchardly Park! Step inside to find original hardwood floors that extend through a generously sized living space, featuring a classic fireplace with a stone surround that anchors the room. The functional kitchen provides ample counter space, a double basin sink, and a range, offering a canvas ready for your modern refresh. Hardwood flooring also graces the versatile dining area, complete with a built-in corner cabinet. Three tranquil bedrooms, each featuring warm wood flooring and abundant natural light, offer comfortable retreats. The functional bathroom provides essential amenities. An exciting feature of this property is the cleverly utilized attic space, transformed into a versatile bonus room complete with a skylight for natural illumination, offering additional living possibilities. There is even a sink upstairs which means that plumbing has been started if you should want to add an additional bath at some time. The spacious, unfinished basement presents endless potential for customization, storage, and future development, including a functional laundry area. You will also find an Oakwood 1/2 bath in the basement as well. Outside, the property includes a private, verdant backyard partially enclosed by a tall wooden fence, ideal for relaxation or entertaining. A paved driveway leads to a detached two-car garage, providing convenient parking and extra storage. Relax on the patio out back on summer evenings. This residence offers an exceptional opportunity to create your dream home in the desirable Oakwood School system.

407 Wonderly Avenue, Oakwood

Courtesy of Kathy A Winter and Coldwell Banker Heritage

$550,000

4 Beds ⋅ 4 Baths ⋅ 963939 MLS ⋅ Olivia Nicodemus

Welcome to one of the timeless homes nestled in Oakwood’s prestigious Golden Triangle where historic craftsmanship & thoughtful modern updates come together beautifully. From the inviting covered front porch to the original hardwood floors, picture rails, wide trim, & charming period details throughout, this home celebrates the character that makes Oakwood so lovely. Even the original cast iron fireplace damper remains as a reminder of the home's remarkable history. The heart of the home is the beautifully remodeled kitchen featuring KraftMaid cabinetry, granite countertops, an oversized center island, abundant storage & a JennAir gas range, creating a space that blends modern function with classic style. Formal living & dining rooms offer generous entertaining space, while the breakfast room provides the perfect spot to relax with morning sun, coffee & a good book. With three finished levels, this home offers exceptional flexibility. The third floor serves as a private bedroom suite complete with its own full bath, making it ideal for a primary retreat, a teenager's dream or guest suite. The finished lower level adds even more living space with a spacious 23' x 13' rec room, cork flooring, granite-topped bar & plenty of room for entertaining. Outside, enjoy the large rear deck, detached two-car garage & a prime location just moments from Oakwood schools, Community Center, parks, restaurants, & shopping. If you've been searching for an authentic Oakwood home that preserves its historic soul while offering today's conveniences, 62 E Dixon Avenue is a rare opportunity!

62 E Dixon Avenue, Oakwood

Courtesy of Olivia Nicodemus and Streetlight Realty LLC

$295,000

3 Beds ⋅ 2 Baths ⋅ 963760 MLS ⋅ Erin Kristbaum

Welcome to this charming Oakwood home just blocks from the heart of the community, offering easy access to coffee shops, restaurants, parks, and local shopping. This beautifully updated residence features a welcoming front porch, gleaming hardwood floors throughout, and an abundance of natural light that fills every room. The thoughtfully designed layout provides first-floor bedrooms and bathrooms for convenient single-level living, while the upstairs owner's suite serves as a private retreat complete with a spacious walk-through closet and full bathroom. The freshly updated kitchen showcases crisp white cabinetry, sleek black countertops, herringbone tile backsplash, and stainless steel appliances including refrigerator, range/oven, dishwasher, and microwave—all included with the sale. A decorative brick fireplace adds warmth and character to the main living area, and elegant arched doorways enhance the home's classic appeal. Step outside to the newly added deck, perfect for relaxing, entertaining, and enjoying outdoor meals in the fenced backyard. Additional features include a full basement offering ample storage and a detached two-car garage. Located within the highly regarded Oakwood City School District, this move-in-ready home combines timeless charm with modern updates in a walkable neighborhood. Some photos have been virtually staged to help you envision the possibilities.

2105 Shroyer Road, Oakwood

Courtesy of Erin Kristbaum and CENTURY 21 The Gene Group

$374,900

3 Beds ⋅ 2 Baths ⋅ 963762 MLS ⋅ Bryan M Barker

Welcome to this charming Cape Cod in the highly sought-after Oakwood community! The location is hard to beat just a few homes from Orchardly Park, complete with a park and newly installed pickle ball courts, only blocks from local dining, shopping, and everything that makes Oakwood so desirable. Inside, you'll appreciate the thoughtful updates completed by the current owner. The beautifully remodeled kitchen serves as the heart of the home, while the updated bathrooms add modern style and convenience. For added peace of mind, the basement has been professionally waterproofed and there's not an area that hasn't been improved by the current homeowners. The spacious primary suite offers exceptional flexibility, creating the perfect private retreat, home office, sitting room, or whatever best fits your lifestyle. The air conditioning unit out back while a bit older has been recently checked and ensured that it is in proper working order. However, the homeowners have thrown in a home warranty for added peace of mind. The upstairs closet is listed as a 4th bedroom in the auditors site and has been utilized as such. Whether you're searching for your first home, your next home, or your forever home, this move-in-ready Cape Cod is one you won't want to miss. Schedule your showing today!

323 Orchard Drive, Oakwood

Courtesy of Bryan M Barker and BHHS Professional Realty

$295,000

2 Beds ⋅ 2 Baths ⋅ 963537 MLS ⋅ Tammy Murphy

Welcome home to this charming Oakwood classic where timeless character meets today's lifestyle. Located in the highly desirable Oakwood School District, this home offers 2 bedrooms plus a versatile second-story loft currently configured as a home office that could also serve as a third bedroom, 1.5 bathrooms, 1,452 square feet of living space, and a semi-finished full basement. Original details—including hardwood floors, crown molding, the original front door, fireplace, and inviting covered front porch—blend seamlessly with thoughtful updates throughout. The sun-filled living room opens to the dining room, creating comfortable gathering spaces, while the updated eat-in kitchen features granite countertops, stainless steel appliances, retro cabinetry, luxury vinyl tile flooring, an exposed brick chimney, and a cozy breakfast nook. Upstairs, the flexible loft provides an ideal work-from-home space or reading area, while the original hardwood flooring remains beneath the carpet in the bedrooms. The finished basement expands the home's functionality with an additional living area, half bath, laundry, and generous storage. Enjoy relaxing on the covered front porch, entertaining on the rear deck, or spending time in the fenced backyard. Additional features include updated windows, recently painted exterior, and a detached 1.5-car garage. One of this home's standout features is its location. Enjoy the convenience of nearby shopping and dining, with parks, the library, schools, and everyday amenities just a short walk away. If you're looking for classic Oakwood charm, flexible living spaces, and a location that makes it easy to enjoy the neighborhood, this home is one you won't want to miss.

336 Peach Orchard Avenue, Oakwood

Courtesy of Tammy Murphy and R H 2 L

$259,900

3 Beds ⋅ 1 Baths ⋅ 963489 MLS ⋅ David Hochwalt

Discover the charm, character, and value of this beautifully updated 3-bedroom, 1-bath Cape Cod in Oakwood. Thoughtfully maintained and truly move-in ready, this home features over $20,000 in recent improvements, including a brand-new front porch, new driveway, professionally refinished hardwood floors, and fresh landscaping that creates exceptional curb appeal from the moment you arrive. Inside, timeless charm meets everyday comfort, while the full unfinished basement offers endless possibilities to expand, create a home gym, workshop, or simply enjoy abundant storage. Outside, you'll find a hard-to-come-by oversized backyard with plenty of room to entertain, garden, play, or simply relax. Perfectly positioned just 700 steps from Orchardly Park and within walking distance of Oakwood schools, the Shops of Oakwood, and Dorothy Lane Market, this home offers the ideal blend of convenience and community. Finding a turnkey home in Oakwood at this price point is increasingly rare—don't miss your opportunity to own one of the area's best values.

430 Claranna Avenue, Oakwood

Courtesy of David Hochwalt and Glasshouse Realty Group

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