Oakwood Real Estate

Oakwood: A Charming City in Montgomery County, Ohio

Nestled in the heart of Montgomery County, Ohio, lies the picturesque city of Oakwood. Known for its tree-lined streets, welcoming community, and rich history, Oakwood is a hidden gem that offers a high quality of life for its residents.

Located just a short drive from downtown Dayton, Oakwood provides the perfect balance between small-town charm and urban convenience. The city boasts a strong sense of community, with numerous local events and gatherings that bring neighbors together. Whether it's the annual Oakwood Summer Fest or the vibrant farmers market, there is always something happening in this lively city.

Oakwood is renowned for its excellent school system, making it an ideal place for families to settle down. The Oakwood City School District consistently ranks among the top in the state, offering a comprehensive and well-rounded education to students of all ages.

Nature enthusiasts will appreciate the abundance of parks and green spaces in Oakwood. Smith Gardens, a local favorite, features beautiful flower beds, walking trails, and a serene pond, providing the perfect backdrop for a leisurely stroll or a peaceful picnic.

If you're a history buff, Oakwood has plenty to offer. The city is home to numerous historic landmarks, including the Wright Memorial Public Library, which pays homage to the famous Wright brothers who hailed from nearby Dayton.

With its charming atmosphere, excellent schools, and convenient location, Oakwood is a city that truly has it all. Whether you're looking for a tight-knit community or a place to raise a family, Oakwood is a city worth considering.

Newest Listings in Oakwood

$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

$1,500,000

5 Beds ⋅ 5 Baths ⋅ 963498 MLS ⋅ David Moyer

An Oasis in the heart of Oakwood. Built into a hillside and singular in its architecture. Conceived in 1973 and cared for to its highest expression through more than $550,000 in meticulous, designer-led renovations. This 5,823 sq. ft. contemporary masterpiece commands a full acre in Oakwood with five bedrooms, five baths, and a floor plan that moves with 360-degree access to the property. The kitchen is a statement unto itself: a complete gut renovation completed in December 2023 featuring quartzite countertops and backsplashes, custom cabinetry, premium Monogram ovens, cooktop, and refrigerator, a Fisher & Paykel dishwasher, and designer finishes curated for the buyer who refuses to compromise. The iconic two-sided fireplace anchors the living spaces, while original pocket doors and soaring volumes speak to the home's architectural heritage. Step outside to discover an expansive new ipe hardwood deck, one of the most durable and luxurious decking materials on earth, completed in 2026 over a fully engineered new roof system. The private pool offers the perfect backdrop for entertaining and evening serenity. A stunning final architectural addition that ties the home's exterior together beautifully is scheduled for completion by mid-October 2026 and includes limestone steps and retaining walls leading to the driveway and front yard. This is a one-of-a-kind property, ready to enjoy.

921 Runnymede Road, Oakwood

Courtesy of David Moyer and Keller Williams Advisors Rlty

$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

$345,000

3 Beds ⋅ 2 Baths ⋅ 964754 MLS ⋅ Ryan Gillen

Welcome to this beautifully remodeled 3-bedroom, 2-bath home in the heart of Oakwood, blending timeless charm with modern updates. The classic exterior and covered front porch offer a warm welcome, while refinished hardwood cherry floors and solid wood doors add to the home's character throughout. The kitchen has been thoughtfully redesigned with high-end quartz countertops, cabinetry, updated flooring, stylish lighting, and stainless steel appliances offering the perfect blend of form and function. The spacious living room features a cozy gas fireplace flanked by custom built-ins, perfect for relaxing or entertaining. The basement has been refreshed with new LVP flooring, drywall, and baseboards, providing additional flexible living or storage space. A detached 1-car garage and fantastic curb appeal complete the package. With a perfect mix of vintage charm and thoughtful renovations, this move-in ready Oakwood gem is one you won’t want to miss!

9 Wiltshire Boulevard, Oakwood

Courtesy of Ryan Gillen and Keller Williams Community Part

$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

$524,900

3 Beds ⋅ 3 Baths ⋅ 964222 MLS ⋅ Tracy Rife

Welcome to this beautifully maintained 3-bedroom, 2.5-bath home nestled in the heart of Oakwood. Situated within easy walking distance of the Oakwood Club, Dorothy Lane Market, and the Shoppes of Oakwood, this home offers the lifestyle buyers dream about. Step inside to discover hardwood floors throughout the main level and a freshly painted interior that feels bright and move-in ready. The spacious open kitchen is a true showstopper, featuring granite countertops, recessed lighting, a 5 stage reverse osmosis system, and built-in cabinetry that blends timeless craftsmanship with modern function—perfect for both everyday living and entertaining. The convenient first-floor primary bedroom offers comfort and flexibility, while the updated upstairs bathroom adds a fresh, contemporary touch to the second level. Downstairs, the full finished basement provides generous additional living space ideal for a family room, home office, gym, or guest retreat. Outside, the large yard is an entertainer's paradise, plenty of room for summer gatherings, gardening, or simply relaxing in your own private oasis. The location truly can't be beat, with beautiful parks, top-rated golf courses, boutique shopping, and beloved local dining all just moments from your front door. Homes in this sought-after Oakwood neighborhood don't come along often. Come experience the perfect blend of classic character, modern updates, and walkable convenience—schedule your private showing today!

24 Peach Orchard Road, Oakwood

Courtesy of Tracy Rife and Glasshouse Realty Group

$465,000

3 Beds ⋅ 3 Baths ⋅ 963162 MLS ⋅ David E Roth

Welcome Home to this Oakwood Beauty - ALL Brick Classic Style Home Offering 3 Bedrooms + 3 Bathrooms and Over 2,000+ Sq/ft. of finished living space includes a lower level 20X17 Family/Rec Room!! Located just West of 48 - short walk to Graeters Ice Cream, Oakwood Club - DLM and Fair Ridge Park! Maintenance Free & Loaded with curb appeal! Beautiful Original Hardwood Floors throughout. Massive Primary Suite Features EnSuite with dual sinks and walk-in closet! Kitchen features SS Appliances. Bathrooms have been updated - Updated windows - Furnace 2021 - Water Heater 2022. Two Car Attached Garage.

204 Hilltop Avenue, Oakwood

Courtesy of David E Roth and Keller Williams Advisors Rlty

$669,900

3 Beds ⋅ 3 Baths ⋅ 964179 MLS ⋅ Tan N Gray

Welcome to a masterclass in home renovation in the highly desirable Oakwood area. Over the last six years, this property has undergone a top-to-bottom transformation. Every major system has been upgraded and absolutely no corner has been cut. Inside, original hardwood floors guide you through light-filled spaces, including a cozy living room with a custom TV cabinet and a gas fireplace with updated chimney liners, caps, and crowns. The kitchen has been renovated kitchen with custom cabinetry, newer appliances with a separate breakfast nook and corner bench seating. A convenient first floor bedroom, full updated bath, spacious living and dining rooms complete the main floor. The upper level features a custom library nook with custom bookcases, desk, and seating. Two oversized bedrooms with plenty of closets featuring custom lighting and outlets and second full bath. The fully finished, dry basement serves as an ideal in-law suite or entertainment hub, complete with a second kitchen, office/4th bedroom option, living area, storage, laundry (with a newer Samsung washer/dryer set), and a third full bath. The mechanical upgrades offer ultimate, worry-free peace of mind: Brand-new roof with 6 wind turbines, LeafGuard gutter system, and modified dormer flashing. Dual HVAC units for multi-level climate control and an upgraded 200-amp panel with a whole-house surge protector. Level 1 & Level 2 (fast charge) electric vehicle chargers installed. Newer water lines, 2 water heaters (always have hot water!), water softener, and radon mitigation system. Outside, relax in your fully fenced backyard oasis featuring a custom gazebo, shed, swing set, and trampoline. Parking is a breeze with a spacious 2-car carport plus 2-car attached garage with natural stone flooring. Take a stroll down to Shafor Park or to the Oakwood Community Center which hosts a full range of athletic activities including volleyball, tennis, spring and fall soccer, swim team and swimming. Call today!

233 Patterson Road, Oakwood

Courtesy of Tan N Gray and Glasshouse Realty Group

$139,900

964054 MLS ⋅ Adam Martin

If your home search has shifted from "buying" to "building," 4031 Pointe Oakwood Way is the exact parcel you need. Situated in the highly sought-after Pointe Oakwood development, this ~0.40-acre lot offers a rare opportunity to construct new in the award-winning Oakwood City School District. The most valuable feature of this property is its open builder status. You are not locked into a developer's mandatory contractor; you have the complete freedom to bring your own custom builder and design a floor plan tailored to your specific lifestyle. Site preparation is simplified, as the lot is cleared (not heavily wooded) and ready for development. Essential utilities, including city water and sanitary sewer, are already available at the street, saving you critical time and upfront infrastructure costs. Location is the ultimate amenity here. Set near the historic Sugar Camp area, the property provides immediate connectivity to local parks, the University of Dayton, Miami Valley Hospital, and the shops of downtown Oakwood. Premium, open-builder parcels in this district rarely hit the market. Walk the lot today and start designing your future.

4031 Pointe Oakwood Dr, Oakwood

Courtesy of Adam Martin and Howard Hanna Real Estate Serv

$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

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