City/Oakwood Real Estate

Welcome to City/Oakwood, a hidden gem nestled in the heart of Montgomery County, Ohio. This charming subdivision seamlessly blends suburban tranquility with urban convenience, making it an ideal place for families, professionals, and retirees alike.

City/Oakwood boasts a rich history and a vibrant community spirit. With tree-lined streets, beautifully maintained parks, and a strong sense of neighborhood pride, residents enjoy a welcoming atmosphere that feels like home. The area is known for its excellent schools, making it a prime choice for families seeking quality education and a safe environment for their children to thrive.

As you explore City/Oakwood, you’ll discover an array of amenities that cater to every lifestyle. From quaint local shops and delightful eateries to modern fitness centers and recreational facilities, there’s something for everyone. The community hosts various events throughout the year, fostering connections among residents and celebrating the unique character of the area.

Nature enthusiasts will appreciate the nearby parks and green spaces, perfect for leisurely strolls, picnics, or weekend adventures. With easy access to major highways and public transportation, commuting to downtown Dayton or other surrounding areas is a breeze, allowing you to enjoy the best of both worlds.

Whether you’re searching for your first home, a cozy retreat, or a place to settle down, City/Oakwood offers a diverse range of real estate options tailored to your needs. Come experience the warmth and charm of this delightful community, where every day feels like a breath of fresh air. Welcome home to City/Oakwood!

Newest Listings in City/Oakwood

$369,900

3 Beds ⋅ 2 Baths ⋅ 965067 MLS

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

$695,000

5 Beds ⋅ 4 Baths ⋅ 963147 MLS

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

$575,000

3 Beds ⋅ 4 Baths ⋅ 963698 MLS

A rare find in Oakwood! This beautiful Oakwood Colonial offers timeless character, quality updates, and exceptional curb appeal. Included in the sale is an additional adjacent parcel, providing expanded green space, and endless possibilities to enjoy one of Oakwood's most picturesque settings. This stunning 3-bedroom, 2 full bath, 2 half bath home features spacious living areas, hardwood flooring throughout much of the home and replacement interior doors and windows that provide updated style and efficiency. The massive primary bedroom easily accommodates king size furniture with room to spare. The redesigned kitchen offers granite countertops, generous cabinetry, and an inviting layout for everyday living. The finished lower level boasts a huge Family Room with a wood burning fireplace and an additional flex room, while built-in storage throughout the home adds both character and functionality. Step outside to professionally landscaped grounds featuring ambient landscape lighting, multiple outdoor living areas, and a hot tub that conveys with the property. Additional highlights include a breezeway, attached two-car garage with dedicated workshop space, and mature landscaping that enhances the home's exceptional curb appeal. Ideally located near Oakwood schools, parks, shopping, and dining, this amazing property offers the perfect blend of classic charm, modern updates, and an included adjacent lot - a rare combination in one of Oakwood's most sought-after neighborhoods. All info believed accurate, please rely on your own verifications.

345 Dellwood Avenue, Oakwood

Courtesy of Jerry A George and BHHS Professional Realty

$414,900

4 Beds ⋅ 3 Baths ⋅ 963250 MLS

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

$625,000

3 Beds ⋅ 3 Baths ⋅ 962360 MLS

Welcome home to this beautifully maintained single-story brick ranch nestled in Oakwood’s highly sought-after Golden Triangle. Offering a thoughtful floor plan, timeless charm, and exceptional storage throughout, this residence combines comfort and functionality in an unbeatable location. The home is built on a double lot with a full basement. The inviting eat-in kitchen features elegant granite countertops and ample workspace including a built-in kitchen desk, while built-in cabinetry in the breakfast room, hallway, and family room adds both character and convenience. The cozy family room is the perfect gathering space, complete with one of two gas-burning fireplaces that create a warm and welcoming atmosphere. With three spacious bedrooms, two full baths, and one half bath, this home provides comfortable accommodations for family and guests alike. Generous closet space throughout ensures plenty of room for organization and storage. Primary bedroom offers a cedar-lined closet. A bright and airy sitting room offers year-round enjoyment and serene views of the lush, private backyard, creating a peaceful retreat in every season. The full basement expands the living space and includes a dedicated workshop along with multiple storage areas to meet all your hobby and organizational needs. Additional highlights include two gas-burning fireplaces, abundant built-in storage, and a beautifully landscaped setting that enhances the home’s appeal. This exceptional Oakwood property offers the perfect blend of classic craftsmanship, modern convenience, and a prime Golden Triangle location. Information is believed accurate yet rely on your own inspections & measurements. New gas water heater installed 2021. Water Softener, Humidifier, Extra Refrigerator/Freezer will be conveyed. Oakwood Occupancy Inspection has been completed and Certificate issued.

249 Greenmount Boulevard, Oakwood

Courtesy of Benita J Wenzler and Howard Hanna Real Estate Serv

$390,000

3 Beds ⋅ 2 Baths ⋅ 960648 MLS

Discover a harmonious blend of classic charm and modern living at this delightful Oakwood residence, where inviting curb appeal and thoughtful design create an immediate sense of home. This two-story property offers 1906 square feet of comfortable living space, featuring three bedrooms and one and a half bathrooms. The welcoming front porch, adorned with classic columns, sets a serene tone amidst landscaped greenery and mature trees, inviting peaceful moments outdoors. Inside, the living area boasts gleaming hardwood floors and a classic brick fireplace, providing a cozy focal point for relaxation. Abundant natural light illuminates this adaptable space, further enhanced by built-in shelving. The contemporary kitchen is a chef's delight, equipped with sleek granite countertops, a practical kitchen island, and stainless steel appliances including a dishwasher, microwave, range, and refrigerator. Recessed lighting and tile flooring complete this bright and functional space. Bedrooms offer comfort and tranquility, with options featuring plush carpeting or warm hardwood floors, and ceiling fans for optimal airflow. The main level seamlessly connects the kitchen to the living area, promoting an open and engaging environment. An unfinished basement provides ample utility space, laundry facilities with a dryer, and extensive storage or potential for a workshop. The property's exterior features maintenance free vinyl siding, complemented by a detached garage. A charming brick patio offers a private outdoor retreat, perfect for entertaining or quiet contemplation. Located in a desirable neighborhood with sidewalks and mature trees, this home offers both privacy and community appeal.

241 Orchard Drive, Oakwood

Courtesy of Timothy A Williams and Glasshouse Realty Group

$335,000

3 Beds ⋅ 2 Baths ⋅ 961475 MLS

Oakwood charm meets move-in ready perfection at 406 East Drive. From the moment you step onto the covered front porch, you'll feel right at home. Inside, hardwood floors and updated windows set a warm, bright tone throughout the home. Kitchen is fully functional with eat in dining space. But if you enjoy formal dining the you’ll love the spacious dining room. The bright and airy finished basement adds valuable and cozy living space. Three generous sized bedrooms and tastefully updated full bath complete the 2nd floor. Outdoors, the paver patio is the perfect spot to unwind or host. Impeccably cared for and ready for its next chapter — don't miss this one.

406 East Drive, Oakwood

Courtesy of Toni Donato Shade and Coldwell Banker Heritage

$895,000

5 Beds ⋅ 3 Baths ⋅ 960696 MLS

Beautiful New Kitchen, Charming Summer House! Step inside 55 Park Road and find old world charm blended with renovations in keeping with the character of this special property. Situated on nearly a half-acre, discover the storybook like setting complete with gardens, fountain, patios and summer house that overlooks the private backyard. Inside discover an incredible new kitchen, thoughtfully designed to maximize storage and workspace complete with custom vent hood over the gas range and built-ins throughout. The light-filled great room has French doors to the patios and flows into the dining room. The home office and living room have southern and western views. Upstairs find a large primary suite, full bath and great walk-in closets as well as three guest rooms, full bath and a charming bedroom on the third floor. The graceful, circular drive sets allows for easy parking for family and friends.

55 Park Road, Oakwood

Courtesy of Felix S McGinnis and Coldwell Banker Heritage

$319,900

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.

$850,000

4 Beds ⋅ 5 Baths ⋅ 960407 MLS

Set on two separately deeded (PID Q71-01005-0020 & Q71-01005-0021), beautifully landscaped lots , on one of Oakwood's most inviting streets, this brick home blends the character of its 1925 origins with top-to-bottom updates that make it feel entirely current. All wood floors were just refinished and many rooms have fresh paint. Inside, the completely reimagined kitchen is the centerpiece — custom in every detail, designed for both daily living and entertaining. The owner's suite opens onto a covered balcony with custom spiral stairway leading to the rear yard and features an elegant dressing room with custom built-ins alongside a fully updated bathroom; a level of finish rarely found. The Pella replacement windows throughout the main house and new custom insulated arched windows in the sunroom bring in natural light while keeping the home's classic exterior profile intact. Four bedrooms and 2 full and 3 half bathrooms offer generous room across aprox. 3194 square feet above grade, with a finished basement providing additional flexible space. A gas log fireplace anchors the main living area with warmth and presence, while French doors connect it to both the sunroom, the rear porch and yard. Step outside to an expansive covered rear porch that overlooks a stone and granite outdoor kitchen — a thoughtfully built extension of the entertaining space, that includes, a pizza oven, built in grill, cook top refrigerator and a wood burning fireplace — surrounded by mature landscaping on a lot that stands out even in this neighborhood. A detached two-car garage, with built-in stairs to a second-floor storage area, completes the picture. A Generac whole house generator, keeps the entire house and garage running during any potential power outages. Safe in basement conveys. Located just a couple of blocks from the shops of Oakwood and dining along Far Hills Avenue, this is a home worth seeing in person. Listing agent is the owner

24 Monteray Road, Oakwood

Courtesy of Kamela Kordik and Kamela & Company Realty

$715,000

5 Beds ⋅ 4 Baths ⋅ 954415 MLS

Situated on one of Oakwood’s most coveted tree-lined streets, this stately Colonial offers timeless elegance, refined updates, and an exceptional location adjacent to Harman Elementary and just one block from Smith Gardens. Boasting over 3,200 square feet, five bedrooms, and four beautifully updated bathrooms, this remarkable residence seamlessly blends classic charm with modern luxury. A welcoming entry introduces hardwood floors, soaring ceilings, and the formal living room features a stunning custom fireplace with an elegant wood mantel and built-in bookcases, creating a warm yet sophisticated gathering space. The expansive formal dining room showcases distinctive built-ins, stylish pendant lighting, and French doors that seamlessly connect to the family room. Filled with natural light, the spacious family room opens directly to the rear patio, creating effortless indoor-outdoor living and entertaining. Designed for both everyday comfort and elevated entertaining, the chef’s kitchen is beautifully appointed with granite countertops, custom cabinetry, a Viking range, center island with seating and prep sink, and a dedicated beverage center. The second level offers four spacious bedrooms and three fully updated bathrooms featuring modern finishes and designer vanities. The luxurious primary suite serves as a private retreat with a generous walk-in closet and beautifully appointed en suite bath. The remodeled third level provides exceptional privacy and flexibility, ideal as a fifth bedroom, guest suite, home office, or bonus living space, complete with a convenient second laundry area. The walk-out lower level offers abundant storage and additional laundry space. Both washers and dryers along with the basement freezer, will convey. Outdoor living is equally impressive with a beautifully designed paver patio, expansive backyard, detached two-car garage, and additional parking pad. A rare opportunity to own a distinguished Oakwood residence!

712 Oakwood Avenue, Oakwood

Courtesy of Emily Pelligra and Coldwell Banker Heritage

$525,000

4 Beds ⋅ 3 Baths ⋅ 958974 MLS

Gorgeous Custom Home greets you with a welcoming front porch and stone-accented columns, then unfolds into an open-concept main level designed for modern living and entertaining. Enjoy a chef-friendly kitchen with quartz countertops, appliances convey-range can be easily converted to gas, large Island, plentiful soft close cabinetry, versatile dining area and durable LVP flooring that flows into a great room anchored by a gas fireplace. Sliding doors open to a deck and private rear patio for seamless indoor-outdoor entertaining. The upstairs owner's suite is bright and spacious, featuring a generous walk-in closet and en-suite bath, while three additional bedrooms, feature oversized closets, a convenient upstairs laundry, and full bath complete the upstairs. You'll find pleasant views offered out each window. The walk-out lower level is nearly finished with carpet and includes a full bath rough-in, ideal for additional living space, media room, or guest suite. Dual Zone A/C, Side entry garage. Excellent location close to schools, parks, downtown Oakwood and Dayton Riverscape. This low maintanance home is conveniently located for an easy commute whatever the destination.

225 Pointe Oakwood Way, Oakwood

Courtesy of Jennifer J Durbin and Irongate 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®