Oakwood Homes under $500,000

Welcome to Oakwood, Ohio—a charming city nestled in Montgomery County, known for its picturesque neighborhoods, vibrant community spirit, and rich historical heritage. Just a stone's throw from the bustling city of Dayton, Oakwood offers residents the perfect blend of suburban tranquility and urban convenience.

Oakwood is renowned for its excellent school system, making it a highly sought-after destination for families. The city boasts beautiful tree-lined streets, lovely parks, and a variety of local shops and restaurants, creating an inviting atmosphere that feels like home. Whether you’re enjoying a leisurely afternoon at one of the community parks or exploring the quaint boutiques along Far Hills Avenue, Oakwood radiates warmth and charm.

For those looking to settle down in this delightful city, Oakwood offers a range of homes priced under $500,000. From charming bungalows to spacious family residences, there’s something for everyone. These homes often feature classic architecture, modern amenities, and lush yards—perfect for both first-time buyers and those looking to downsize.

Living in Oakwood means enjoying a close-knit community while still having easy access to the cultural and recreational activities of nearby Dayton. With a variety of homes available at an affordable price point, now is the perfect time to discover your dream home in this enchanting city. Experience the Oakwood lifestyle, where community, comfort, and charm come together seamlessly. Come explore the possibilities today!

Newest Oakwood Homes under $500,000

$350,000

3 Beds ⋅ 2 Baths ⋅ 970681 MLS ⋅ Lisa M Burke

Welcome Home to this classic Ranch bungalow! Built in 1951, this house has great bones and includes features of the mid-century era with great updates. The wood floors gleam in the light from many windows on the main level. Two Bedrooms each include two closets with a full Bathroom in between. Upstairs is another cozy bedroom with a good size closet and additional attic storage. Back on the main level, the wall between Dining Room and Kitchen has been removed to create an open space with flexibility for meals with a few people or a crowd...Granite countertops, updated cabinets and SS appliances make cooking a breeze. The Basement has also been finished, offering plenty of space for entertaining and recreation. A Full Bathroom is conveniently located here, along with a bonus Guest/Exercise Room and a Laundry Room. Out back is a fantastic Back Yard complete with Patio, Fire Pit, an awesome sledding hill and Detached Garage. New roof (complete tear-off) and gutters in September 2026. See this house today and make your new home dreams a reality!

512 Volusia Avenue, Oakwood

Courtesy of Lisa M Burke and Coldwell Banker Heritage

$479,900

4 Beds ⋅ 3 Baths ⋅ 970808 MLS ⋅ Janet L Miller

The classic stucco exterior anchors this two-story residence, believed to be an original farm home in Oakwood. A large, covered porch measuring ten by thirty-one feet leads to an air lock entry room. Inside, the spacious living room features a full wall gas fireplace with shelving, while the adjacent library offers its own fireplace. The formal dining room accommodates a large table alongside other furniture. The kitchen is outfitted with a large island, Corian counters, and KraftMaid cabinetry featuring many drawers, plus one cabinet with a roll-out pantry. A butler pantry hosts an additional oven, access to a half bath, and entry to the rear two-tier deck. 1st and 2nd floors feature hardwood flooring. The second floor features four bedrooms and two full baths, all situated off a large hallway with built-in cabinets, drawers, and a large linen closet. The primary bedroom bathroom is accessible from both the bedroom and the hallway, while an additional hall bath services the remaining three bedrooms. One of the remaining bedrooms contains a dummy fireplace, and all bedrooms feature closet space. From this level, stairs lead to the third-level walk-up attic, with loads of possibilities. The basement is divided into four distinct areas including laundry, mechanical, storage, and a rec room that features a built-in bar. Outside, the property features a carriage house garage with room for three cars and overhead storage. The two-tier deck overlooks a large stone bar-b-que on the 0.32-acre lot. The rear yard offers ample recreation area. Recent maintenance includes a painted stucco exterior, six-inch gutters with leaf filters installed on the home and top gutters of the garage, and vinyl windows installed in 2000. Additionally, the basement was professionally waterproofed in 2007 with a transferable warranty, the air conditioning was updated in 2018, and a new water heater was installed in 2024. Be sure and put this most unusual home on your list to view!

355 East Drive, Oakwood

Courtesy of Janet L Miller and RE/MAX HomeBase

$389,900

3 Beds ⋅ 2 Baths ⋅ 970457 MLS ⋅ Kunal N Patel

Over $60,000 in improvements since purchased in 2022! This beautifully maintained stone and brick Cape Cod combines character with thoughtful updates throughout. Hardwood floors flow through much of the home, while the open, light-filled layout makes the living spaces feel warm and inviting. The kitchen features granite countertops, stainless steel appliances, ample soft-close cabinetry, and a peninsula with additional seating that opens to the dining area. French doors lead to the 3-season room, surrounded by windows and offering flexible additional living space, mudroom functionality, and convenient access to the attached, extended 2-car garage. Two bedrooms and an updated full bath are located on the main level. Upstairs, the spacious primary suite feels like its own retreat with two walk-in closets, built-ins, a mini-split for added comfort, and an updated en suite bath featuring a double vanity and an oversized custom shower. The clean basement provides plenty of storage and additional possibilities. Major improvements include kitchen flooring (2026), HVAC (2025), roof and gutter covers (2024), primary suite mini-split, cedar front fence, garage door motor, electrical improvements, and more. A complete list of over $60,000 in improvements is available for review. With major systems addressed, a turnaround driveway, attached 2-car garage, and a functional layout, this home is ready for its next chapter

418 Harman Boulevard, Oakwood

Courtesy of Kunal N Patel and Glasshouse Realty Group

$419,500

3 Beds ⋅ 3 Baths ⋅ 970423 MLS ⋅ Georgiana C Nye

Welcome to Pointe Oakwood! This home is built by Peebles and you don't want to miss making this property your home! This sunny and bright 2,023 sq. ft. home offers an inviting floor plan, beautiful natural light and an exceptional location close to UD, downtown Dayton and all that downtown Oakwood has to offer. The open main living area is designed for easy living and entertaining, with a spacious kitchen featuring a generous eating bar and a vaulted living room filled with large windows. A fireplace anchors the space and creates a warm focal point, while the living area opens to a private wood deck for relaxing or enjoying your morning coffee. The first-floor primary suite offers comfort and convenience with a large walk-in closet, dual sinks and a tiled walk-in shower. The main level also includes a second bedroom, full bath and utility room. Upstairs, a spacious loft provides flexible living space along with a third bedroom and another full bath—perfect for guests, an office or a private retreat. ALL carpet is brand new from Bockrath's in 2026. A 2-car attached garage adds everyday convenience. Nestled in a quiet, desirable neighborhood with an amazing location, this Pointe Oakwood home offers the perfect blend of comfort, space and accessibility.

238 Pointe Oakwood Way, Oakwood

Courtesy of Georgiana C Nye and Coldwell Banker Heritage

$350,000

3 Beds ⋅ 2 Baths ⋅ 970243 MLS ⋅ Georgiana C Nye

Totally adorable 1.5-story brick home in the heart of Oakwood! This charming 3-bedroom, 2-full-bath home offers a wonderful location just two doors from a neighborhood park and only two blocks from the Shops of Oakwood. Walk to shops, restaurants, parks and more! Inside, beautiful hardwood floors shine throughout much of the home, adding warmth and character. The updated kitchen is stylish and functional, making it a true highlight of the home. Two bedrooms and a full bath are conveniently located on the main level. From the dining room, access the three-season porch that stretches across the back of the home and provides wonderful additional living space—perfect for morning coffee, relaxing or enjoying the seasons. Upstairs, the primary suite is roomy, with built-in cabinets and bookcases, tons of closet space, a separate full bath and access to a private upper level deck. The clean, dry basement offers excellent storage and utility space. Outside, there is a deck for your outdoor enjoyment, that is accessed from the three season porch, a sweet yard, and partial fence. Charming, updated and wonderfully located—this is Oakwood living at its best!

212 Dell Park Avenue, Oakwood

Courtesy of Georgiana C Nye and Coldwell Banker Heritage

$400,000

3 Beds ⋅ 3 Baths ⋅ 969973 MLS ⋅ Laurie Westheimer

Classic Oakwood charm meets modern comfort- offering nearly 2,000 SF above grade plus almost 1,200 SF of finished lower-level living space. Thoughtfully updated while preserving its timeless character, this home combines the warmth and craftsmanship of a classic Oakwood residence with the space and amenities today's buyers are seeking. Best of all, you're just a short walk from downtown Oakwood. A welcoming enclosed front porch sets the tone before you step inside to discover rich architectural details including hardwood floors, arched doorways, original built-ins, custom plantation shutters, and abundant natural light. The spacious living room is anchored by a beautiful fireplace flanked by original built-in cabinetry and flows seamlessly into the formal dining room. The thoughtfully remodeled kitchen features solid wood shaker-style cabinetry, granite countertops, stainless steel appliances, pantry storage, and generous workspace. There are two bedrooms on the main level (one with built-in Murphy bed), while the entire second floor is dedicated to a private primary retreat complete with a walk-in closet and en suite bath—a rare feature for an Oakwood home of this era. Brand-new carpet throughout provides a fresh, move-in-ready feel while complementing the home's timeless appeal. The expansive finished lower level offers more versatile living space, perfect for a family room, recreation area, home office, fitness room, or hobby space. An oversized laundry room with extensive built-in cabinetry provides exceptional storage and organization. Thoughtful improvements include a remodeled kitchen (2017), dimensional shingle roof (2017), high-efficiency HVAC (2022), tankless water heater (2022), updated electrical, updated lighting, brand-new carpet throughout main floor and luxury vinyl installed throughout the basements (2026). New battery back up for sump pump in 2026. Outside, you'll find professionally landscaped grounds and a detached 2-car garage.

327 East Drive, Oakwood

Courtesy of Laurie Westheimer and BHHS Professional Realty

$365,000

3 Beds ⋅ 2 Baths ⋅ 969929 MLS ⋅ Morgan Marie Means

Welcome to this charming 3-bedroom, 1.5-bath two-story home in desirable Oakwood! Offering 1,308 sq. ft. of living space, this home features a spacious living room with beautiful wood beams, a full basement, and a 2-car detached garage. The fenced-in backyard offers a great space for relaxing or entertaining with fire pit and fireplace under the pergola which was all built in 2022. Enjoy the front porch and back deck, along with a driveway replaced in 2021. Brand new siding in 2021. The kitchen is open to the dining room which offers a great space to entertain. This home is in an phenomenal location, with shopping, restaurants, and more just a short distance away. Conveniently located near The Greene and WPAFB, this home offers easy access to everyday conveniences, dining, shopping, and entertainment. Furnace 2017. A/C 2017. Roof 2017. Dishwasher 2017. Microwave 2017. Water Heater 2020

416 Monteray Avenue, Oakwood

Courtesy of Morgan Marie Means and Irongate Inc.

$273,750

2 Beds ⋅ 1 Baths ⋅ 969886 MLS ⋅ Donna S Deaton

You won't want to miss out on this Oakwood home offering beautiful hardwood floors throughout. The kitchen features maple cabinetry and stainless steel appliances, a greenhouse window, while double hung windows bring in plenty of natural light. The semi finished basement offers additional space for a rec room, office, workout area or future finishing. Outside, enjoy a fenced yard and oversized detached garage with opener, providing excellent parking and overhead storage. HVAC replaced in 2015. Conveniently located near shopping, dining, parks and everything Oakwood has to offer, all within the Oakwood School District. Property is being sold AS IS to settle an estate. Rooms are virtually staged.

443 Triangle Avenue, Oakwood

Courtesy of Donna S Deaton and RE/MAX Victory + Affiliates

$348,000

3 Beds ⋅ 2 Baths ⋅ 969705 MLS ⋅ Jessika Webb

Classic Oakwood charm with an added note of peace of mind. The sellers report no basement water leaks during their 18 years of ownership, a particularly noteworthy feature given recent flooding concerns in the Dayton area. This two-story home offers three bedrooms, two full baths, and a flexible main-level layout with both a living room and separate family room. The finished basement provides additional space for recreation, hobbies, a home office, or storage. A detached two-car garage adds convenient parking and storage space. Located just a short walk from the elementary school and the Shops of Oakwood, this home offers comfortable living and a convenient Oakwood location.

306 Telford Avenue, Oakwood

Courtesy of Jessika Webb and Ownerland Realty, Inc.

$399,900

3 Beds ⋅ 2 Baths ⋅ 969619 MLS ⋅ Jey Ellis

This amazing cape cod is full of character and warmth and features lots of updates! You will realize right away when you see the beautiful curb appeal that you are about to see a wonderful home inside and out. A very open layout awaits when you walk through the door to the spacious living room, separate dining and updated kitchen. Two good-sized bedrooms are on the main level with a fully remodeled bath in between. The primary bedroom suite on the 2nd level is stunning! With the ceiling raised to the beams, the space is incredible and contemporary with built in shelves and a huge bathroom featuring a walk-in closet! There is a lovely enclosed breeze way just off the kitchen in addition to a small deck that houses a hot tub. This area also allows access to the two car garage with overhead storage. This one is ready for you to call home! Schedule your private tour today.

350 Greenmount Boulevard, Oakwood

Courtesy of Jey Ellis and Coldwell Banker Heritage

$399,900

6 Beds ⋅ 3 Baths ⋅ 967865 MLS ⋅ Emily Gay

Investment opportunity in desirable Oakwood! This well-maintained duplex offers 2,200+ square feet of living space, with two spacious units featuring approximately 1,100 square feet each, 3 bedrooms and 1 full bathroom per unit. Both units are nicely updated and currently occupied, providing immediate rental income with leases extending into 2027. The first-floor unit features a new bathroom, fresh carpet and paint, and updated fixtures. The second-floor unit has been thoughtfully updated with a new kitchen featuring granite countertops and stainless-steel appliances, new bathroom, fresh paint, and updated fixtures. A full basement provides substantial additional space and potential for future value-add improvements. Current rents are $1,600/month for the first-floor unit through 8/31/27 and $1,700/month for the second-floor unit through 9/30/27. Owner currently pays water, sewer, and trash, with one water meter averaging approximately $180/month. This is a great opportunity to expand your portfolio in the highly desirable Oakwood area.

1920-1922 Shroyer Road, Oakwood

Courtesy of Emily Gay and Agora Realty Group

$454,900

4 Beds ⋅ 3 Baths ⋅ 969153 MLS ⋅ Tami Holmes

Timeless elegance, exceptional privacy, and historic charm come together in this remarkable 1913 residence nestled in the heart of Oakwood. Set far back from the road and surrounded by beautiful, mature landscaping, this 4bedroom, 3-bath home offers a rare sense of seclusion while remaining perfectly positioned in one of Oakwood’s most desirable settings.From the moment you arrive, the inviting front porch—complete with a classic porch swing—sets the tone for a home filled with warmth, character, and architectural distinction. Step inside to discover stunning original hardwood floors that showcase the craftsmanship and history of the home. The gracious living room is anchored by a beautiful gas fireplace, creating an elegant yet comfortable gathering space. Thoughtful updates complement the home’s original character, including a beautifully renovated primary en suite bathroom that creates a sophisticated and relaxing private retreat.Outside, the backyard feels like a sanctuary of its own. Lush, mature landscaping and thoughtfully designed outdoor spaces provide exceptional privacy and a picturesque setting for entertaining, relaxing, or enjoying peaceful evenings at home.Adding to the property’s appeal is an impressive detached carriage house offering parking for up to four vehicles—an extraordinary find in Oakwood. Beyond the garage space, additional unfinished areas provide tremendous potential for future living quarters, a guest suite, home office, studio, or entertaining space, with the opportunity to add another bathroom. Walkable to all of the Brown street restaurants and you will love the winter views of the city from upstairs and the Carillon Christmas Tree from the living room windows! Rich in history while thoughtfully enhanced for modern living, this distinctive Oakwood residence offers an exceptional combination of original character, privacy,and understated luxury. There is an invisible fence that surrounds the whole property.

204 W Schantz Avenue, Oakwood

Courtesy of Tami Holmes and Tami Holmes Realty

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