City/Oakwood Homes under $300,000

Welcome to Oakwood, Ohio – a charming suburban enclave nestled within Montgomery County that perfectly blends small-town warmth with modern conveniences. Known for its picturesque streets and friendly community, Oakwood offers a delightful living experience just minutes away from the vibrant city of Dayton.

This inviting subdivision is characterized by its beautiful tree-lined avenues, meticulously maintained parks, and a rich sense of history. Oakwood is renowned for its excellent school system, making it an ideal place for families looking to settle down in a nurturing environment. The community fosters a strong sense of belonging, with numerous local events and gatherings that bring neighbors together.

For those seeking affordable housing options, Oakwood boasts an impressive selection of homes priced under $300,000. These residences range from charming bungalows to cozy family homes, each offering unique architectural styles and character. With a variety of layouts, sizes, and features, there’s something to suit every taste and lifestyle. Many of these homes are situated on spacious lots, providing ample outdoor space for gardening, play, or simply enjoying the serene surroundings.

Living in Oakwood means enjoying easy access to local shops, dining, and recreational facilities, all while being part of a community that values connection and quality of life. Whether you’re a first-time homebuyer or looking to downsize, Oakwood presents an incredible opportunity to find your dream home in a welcoming and vibrant neighborhood. Come explore the beauty and charm of Oakwood, where your perfect home awaits!

Newest City/Oakwood Homes under $300,000

$273,750

2 Beds ⋅ 1 Baths ⋅ 969886 MLS

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

$269,900

3 Beds ⋅ 1 Baths ⋅ 969699 MLS

Move-in ready and full of potential. This 3-bedroom, 1-bath home offers 1,305 square feet of well-kept living space, a full unfinished basement, and a detached 2-car garage. Brand new and remodeled kitchen with new appliances. Hardwood floors run throughout the main level. The spacious living room centers on a fireplace and opens to a generous dining room, which leads into a kitchen with abundant counter space and ample cabinetry. Just off the kitchen you'll find rear-yard access and stairs to the basement, where the mechanicals, washer and dryer hookups, and plenty of storage are located. Three comfortable bedrooms and a full bath complete the main level. Outside, the fenced back yard offers room to relax, play, and entertain, with the detached 2-car garage just beyond. A new roof and soffits in 2022 mean the big-ticket item is already handled, leaving you free to add your own finishes and style. Freshly painted.

327 Patterson Road, Oakwood

Courtesy of Angela R Flory and eXp Realty

$289,900

3 Beds ⋅ 2 Baths ⋅ 960775 MLS

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 web site comes in part from the Broker Reciprocity™ program of the Multiple Listing Service of Greater Cincinnati. Real estate listings held by brokerage firms other than our company are marked with the Broker Reciprocity™ logo (the small house as shown to the left) and detailed information about them includes the name of the listing brokers. This data is up-to-date as of . Copyright 2026, MLS of Greater Cincinnati, Inc. All rights reserved. Information deemed reliable but not guaranteed.

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 Mark Ryan Group RE/MAX Victory + Affiliates 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®