City/Oakwood Homes under $500,000

Welcome to the charming community of Oakwood, Ohio, where suburban tranquility meets urban convenience! Nestled in Montgomery County, Oakwood is a picturesque city that boasts tree-lined streets, beautiful parks, and a strong sense of community. Known for its excellent schools and family-friendly atmosphere, Oakwood is an ideal place for those looking to settle down in a vibrant and welcoming neighborhood.

If you're searching for a home that balances quality and affordability, you'll be delighted to know that Oakwood offers a variety of options under $500,000. Whether you're a first-time homebuyer, a growing family, or looking to downsize, you'll find an array of beautifully designed houses that cater to diverse lifestyles. From charming bungalows to spacious two-story homes, Oakwood's real estate market features properties that blend modern amenities with classic architectural styles.

Living in Oakwood means enjoying a wealth of local amenities. Indulge in the quaint shops and delightful eateries along Far Hills Avenue, or take a stroll through the lush parks that dot the area. With easy access to major highways, commuting to nearby cities like Dayton is a breeze, allowing you to enjoy the best of both worlds—peaceful suburban living and vibrant city life.

Discover your dream home in Oakwood today, where you can create lasting memories in a community that welcomes you with open arms. With homes available under $500,000, your ideal lifestyle in this enchanting city is just a step away!

Newest City/Oakwood Homes under $500,000

$309,900

3 Beds ⋅ 3 Baths ⋅ 972267 MLS ⋅ Alyssa Austin

Welcome home to this adorable Craftsman Style Bungalow! * Sitting a block from the heart of Oakwood, you have it all! * Walking distance to shops, restaurants & popular Dorothy Lane Market * You'll notice attention to detail in the Woodwork throughout * Beautiful archways & Built-ins give it that charm & character! * Kitchen Boasts Granite counters, SS appliances & open to Family room * Rounding out the first floor is the Primary & Full Bath * Upstairs you'll find a second Full Bath & 2 spacious Bedrooms * The Basement has room for so much potential - additional flex spaces of Office, Play room, Gym or just extra Storage! * 1 car Detached Garage & fenced yard off the Deck complete the Backyard * Call for your private showing today! * See attached list of updates *

150 Oak Knoll Drive, Oakwood

Courtesy of Alyssa Austin and Comey & Shepherd REALTORS

$325,000

3 Beds ⋅ 2 Baths ⋅ 972132 MLS ⋅ Jonathan Patterson

Discover this beautifully updated two-story Victorian-style home in Oakwood, where classic character meets modern comfort. Fresh landscaping and a spacious covered front porch create a welcoming first impression. Inside, a spacious foyer leads to an inviting living room filled with natural light from the bay window, with pocket doors connecting to the formal dining room. At the heart of the home, the remodeled wraparound kitchen features new shaker-style cabinetry, quartz countertops, a deep single-basin sink, and stainless steel appliances, with plenty of room for cooking and entertaining. A breakfast nook with additional cabinetry and counter space, a convenient powder room, and a separate laundry area with backyard access complete the first floor. Upstairs, built-in bookshelves add character to the staircase leading to three generously sized bedrooms, including a 14’ x 15’ primary bedroom with a bay window overlooking the street. The updated full bathroom features a tiled shower with a built-in soap niche, an oversized vanity, and new flooring and fixtures. An additional highlight is the lofted attic space, accessible by stairs in the middle bedroom. Finished with carpet and knee walls, this versatile area offers options for additional storage or flexible use. The full unfinished basement provides even more storage space. Outside, enjoy the spacious fenced backyard and detached two-car garage. Just a few short blocks from Edwin D. Smith Elementary, Wright Memorial Public Library, and Orchardly Park, this home combines timeless Victorian charm, thoughtful updates, and a convenient Oakwood location.

1723 Shroyer Road, Oakwood

Courtesy of Jonathan Patterson and Irongate Inc.

$359,900

6 Beds ⋅ 2 Baths ⋅ 971971 MLS ⋅ Austin R Castro

Charming Oakwood Duplex - offering great potential. Rent out both units or live in one and rent out the other. Each unit offers 3 bedrooms, 1 full bathroom, walk-in closet, living room, dining room, and kitchen. The property also includes a 2-car garage, off-street parking, and sits on a desirable tree-lined street. Notable updates include updated heating and air, refinished hardwood floors in both units and updated bathroom and kitchen countertops for #1925. #1923 pays $1500 on a month-to-month basis. #1925 pays $1,500/mo with a lease expiration of September 30,2027.

1923 Shroyer Road, Oakwood

Courtesy of Austin R Castro and Coldwell Banker Heritage

$379,000

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

$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

$350,000

3 Beds ⋅ 2 Baths ⋅ 968889 MLS ⋅ John Pawelski Jr

Charming 3-bedroom, 2-full-bath brick Cape Cod in Oakwood filled with classic character! Beautiful floors, original woodwork and a spacious living room with fireplace welcome you inside. The roomy upstairs offers a private third bedroom and full bath with a classic clawfoot tub. Enjoy an updated main-level bath, full basement with plenty of storage and workspace, covered rear porch, generous driveway and detached garage. Classic Oakwood charm with plenty of space to make your own! Agent owned.

406 Spirea Drive, Oakwood

Courtesy of John Pawelski Jr and Plum Tree Realty

$389,000

4 Beds ⋅ 2 Baths ⋅ 965924 MLS ⋅ Eric Weimer

Charming Oakwood home that boasts timeless character and thoughtful updates! The main level features beautifully refinished hardwood floors, complemented by a modern, neutral color scheme and stylish lighting throughout. Elegant baseboards, detailed woodwork, and arched doorways add to its appeal. The three-season room adjacent to the living area creates an open, airy atmosphere filled with natural light and provides extra space for relaxation. The kitchen has been updated with 42-inch cabinets, quartz countertops, a farmhouse sink, stainless steel appliances, large-format floor tiles, a beadboard backsplash, open shelving, and generous counter space. The primary bedroom includes built-in shelving, a walk-in closet, and additional storage options. Both full bathrooms have been renovated with vanities, tile work, fixtures, lighting, and linen closets. Outside, the home features a new poured patio, a cozy fire pit area, and a beautiful pergola—perfect for outdoor gatherings and entertaining. Brand new windows throughout with elegant Roman shades enhance the home's charm and energy efficiency. Located near several parks and local amenities, this wonderful home is ready for you to call it yours. Schedule a visit today!

252 Aberdeen Avenue, Oakwood

Courtesy of Eric Weimer and Glasshouse Realty Group

$399,800

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

$279,000

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.

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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®

City/Oakwood Homes under $500,000

Newest City/Oakwood Homes under $500,000

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