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$599,900
3 Beds ⋅ 4 Baths ⋅ 968352 MLS ⋅ Jill Aldineh
Experience the perfect blend of mid-century modern architecture and expansive, private living in this highly sought-after West Oakwood retreat. Situated on nearly an acre at the end of a private lane off a cobblestone avenue, this home offers a tranquil escape with stunning views from every room. The thoughtfully designed circular floor plan creates an effortless flow for both daily life and large-scale entertaining. The heart of the home is a light-filled kitchen ffeaturing vaulted ceilings, a skylight, custom cabinetry, leathered luxury granite, and new double ovens. The spacious dining room blends seamlessly into s sun-drenched sunroom, while the expansive living room-anchored by a handsome brickfireplace-opens to an outdoor balcony providing the perfect setting for unwinding amidsts the lush grounds. The main level primary en suite is a private sanctuary with a seperate shower and tub. Two additional bedrooms are connected by a convenient Jack-and-Jill bathroom. The walk-out lower level offers incredible versatility, functioning as a complete apartment-style suite with its own full kitchen and bathroom-ideal for multigenerational living, guests, or a home office, The level features impressive Marvin multi-sliding doors that open to the expansive yard and patio. With a fully updated exterior (including a new roof, siding, gutters, fascia, and soffit) a three-car garage, and ample additional parking; this property is as practical as it is beautiful. Don't miss this rare opportunity to own a private, versatile home in one of Oakwood's most desirable locations.

1200 Oakwood Avenue, Oakwood

Courtesy of Jill Aldineh and RE/MAX Victory + Affiliates
$499,900
4 Beds ⋅ 3 Baths ⋅ 968565 MLS ⋅ Toni Donato Shade
Set in the heart of Oakwood, 148 Telford Avenue is one of the neighborhood's original Sears Craftsman homes. This 1920-built home offers an open floor plan for modern living while preserving its original character and detail. The main level is bright, open, and updated throughout. It starts at an inviting front foyer with plenty of room to welcome guests, and flows into both formal and informal living spaces, including a dining area with a built-in wood bench. Preparing dinner will be a joy in the updated kitchen, which opens to the family room. Four bedrooms provide room to spread out, including a primary suite with a generously sized, updated bathroom featuring a soaking tub and large walk-in shower. The finished basement adds significant everyday and entertaining space, including a third full bath—plus a surprise bonus space, perfect for watching your favorite team. Outdoors, enjoy the built-in firepit or fire up the grill and dine on the stamped concrete patio, all within a fully fenced yard. Conveniently located close to Smith Elementary and Wright Library, this walkable neighborhood offers shopping, dining, and easy access to downtown Dayton, WPAFB, major hospitals, and highways. This is a true gem—you won't want to miss it.

148 Telford Avenue, Oakwood

Courtesy of Toni Donato Shade and Coldwell Banker Heritage
$545,900
5 Beds ⋅ 4 Baths ⋅ 966912 MLS ⋅ Scot M Rife
Welcome to 220 Greenmount Boulevard, ideally situated along one of Oakwood’s most beautiful tree-lined boulevards. This classic brick Tudor blends timeless architectural character with extensive modern updates. Inside, you’ll find beautifully refinished hardwood floors, original architectural details, and spacious living areas filled with natural light. The completely renovated kitchen features new cabinetry, granite countertops, updated fixtures, and stainless steel appliances. Two full and two half bathrooms have also been tastefully updated with modern finishes. Additional improvements include new windows throughout and a new ductless mini-split system on the third floor, enhancing comfort and energy efficiency. The newly finished basement provides valuable additional living space and includes a convenient half bath—ideal for a family room, home office, fitness area, or recreation space. The third floor offers a spacious bonus room and an additional bedroom. Outside, enjoy a private backyard and a two-car garage with a new garage door and opener. Conveniently located near parks, schools, shopping, and dining, this move-in-ready home offers the perfect combination of historic elegance and modern convenience. Agent owned.

220 Greenmount Boulevard, Oakwood

Courtesy of Scot M Rife and Plum Tree Realty
$494,000
3 Beds ⋅ 3 Baths ⋅ 966719 MLS ⋅ Leigh A Walters
This delightful red brick cape cod is inviting with a brick-edged walkway to the entrance. The well-maintained yard and hydrangea bushes are stunning. Additionally, the home is situated in a convenient Oakwood neighborhood that is close to Shafor Park, schools and Community Center. The boulevard has great community parades and fun engaging activities. The interior of the home is warm and inviting and completely updated for today's living. Traditional, the living has a colonial mantel and fireplace. The wainscoting in the dining room is distinctive. Both rooms have beautiful hardwood floors and crown molding. An abundance of dark wood cabinetry and pantry are featured in the kitchen. An en suite bedroom and attached full bathroom with shower complete the first floor. Upstairs are two nice-sized bedrooms, an updated bath and lots of storage including a walk-in California closet. Plus, a secret room behind the bookcase. The basement level has a full bathroom, finished family room and separate office. The Back yard is a retreat with a covered patio cooking area, vegetable garden and inground swimming pool with an attractive fence. home also features 2 car detached garage with opener and storage. Call today for a private showing. Fireplace/chimney is operable yet is not warranted. New Roof 2020, New HVAC 2024

532 Shafor Boulevard, Oakwood

Courtesy of Leigh A Walters and Irongate Inc.
$819,000
4 Beds ⋅ 4 Baths ⋅ 966693 MLS ⋅ Joanne Cronin
Gorgeous French-Norman Tudor built in 1929 - an Oakwood residence where timeless character & modern living combined with an exceptional location blend together beautifully. Museum quality details: original leaded & stained-glass windows, French doors, bas-relief plaster & intricately detailed crown molding showcase this one-of-a-kind residence. Kitchen & dining room include original built-in cabinets. Living room is adjoined by an elevated dais that features roped columns, wrought-iron half-walls & features a polished marble & terrazzo floor that can be used as a music room, office, or gathering area. Guest bath & sunroom boast original Rookwood tile, which further elevates the overall prestige of the home. The home reveals an extraordinary level of craftsmanship not found in newer construction...even in Oakwood. Entrance opens to a center staircase, formal dining room w/original built-in china cabinet & an elegant living room anchored by a gracious hearth with unique plaster details. Chef's kitchen marries character with modern function, featuring custom cabinetry, granite countertops, stainless-steel appliances, commercial-style gas range, charming banquette, custom eat-in kitchen table, & original built-in china cabinet. Upstairs features well-appointed bedrooms and original built-in linen closet along with original iron light fixtures and wall sconces. Master bedroom features an ensuite full bath. Don't miss the finished LL complete with wood floors and full custom wainscotting that make the room a statement unto itself. Outside, the property extends the living experience with an outdoor fireplace, pergola, stone paths & gardens in a setting designed for relaxing, entertaining & enjoying the charm of the Oakwood community. A distinctive feature of the home is the wrought iron window boxes that, when filled with seasonal foliage, has prompted neighborhood children to refer to it as the "Fairytale" house...beautifully maintained & very rich in history.

2020 Coolidge Drive, Oakwood

Courtesy of Joanne Cronin and Irongate Inc.
$685,000
4 Beds ⋅ 4 Baths ⋅ 966582 MLS ⋅ Claire Dunn
Welcome to 311 Harman Blvd, a charming Tudor home in Oakwood, filled with warmth and architectural character. Located on a quiet, tree lined boulevard near Oakwood schools, the Oakwood Community Center and Dorothy Lane Market, this home offers convenient access to shopping, dining and downtown Dayton. Hardwood flooring flows through much of the main level. The remodeled open concept dining room, kitchen and family room creates a welcoming space for everyday living and entertaining. The kitchen features updated cabinetry, stainless steel appliances, updated flooring and a newer refrigerator. Heated floors add comfort to the family room, which also features a gas log fireplace and opens to a covered porch. Integrated indoor and outdoor Sonos audio enhances gatherings throughout the home and outdoor living areas. A first floor laundry area adds everyday convenience. The home offers four bedrooms, including an updated primary suite with a private bath and newer custom shower glass. The beautifully finished basement provides an impressive extension of the living space with a second family room, kitchenette and wet bar. Elevated finishes in both the full bathroom and kitchenette bring a polished feel to this flexible retreat. A built in Murphy bed provides comfortable guest accommodations while preserving valuable floor space. Outdoor features include updated landscaping, a patio, privacy fencing and a gated driveway. The oversized attached two car garage provides additional storage and workshop space. Major improvements include the roof in 2017, professional asbestos removal and encapsulation in 2023, chimney tuckpointing and masonry repairs in 2023, and a new water heater in 2024. Additional updates include fresh interior paint, reverse osmosis and whole house water filtration, subpanel grounding, attic gable screening, cleanout and pest deterrence. Blending timeless Tudor charm with modern comfort, this special Oakwood home is ready to welcome its next owners.

311 Harman Boulevard, Oakwood

Courtesy of Claire Dunn and Coldwell Banker Heritage
$487,500
3 Beds ⋅ 3 Baths ⋅ 964997 MLS ⋅ Robert Wilson
This charming Oakwood classic English Tudor home has so many custom and gracious features. The quality and craftmanship is on display from the moment you approach the 19x16 covered stone paved front porch with custom wood front door. Awesome 1st floor offers 26x13 living rm with fireplace, large formal dining rm, breakfast nook with wine bar with wine cooler/beverage refrig plus built-in planning desk and a beautiful remodeled kitchen with custom cabinets and Kitchen Aid appliances. Spacious 21x13 primary en suite bedroom with custom built-in closets and drawers. This home has beautiful hardwood floors. Finished basement offers spacious recreation room and large utility room with storage area. New boiler 2026. New 24x12 deck 2023. New washer & dryer 2022. Replacement windows. So many of the reasons people select Oakwood as their residence: Excellent public schools, historic charm and architecture, close knit community, proximity to downtown Dayton, strong city services, green spaces & recreation. Shafor Park is Oakwood's largest recreation complex & includes 3.3 acres of playground, ball-field, basketball court, six tennis courts & an outdoor pool. A special feature of Shafor Park includes a fountain where kids can play on hot summer days. The shelter house can be reserved for family & group picnics. Activities include summer day camp, tennis lessons, Ice Cream Social, Family Fall Festival and Christmas activities. Next to the pool and Shafor Park is the Oakwood Community Center which offers aerobics & ballet classes. The Oakwood dog park is only short distance away .Fireplaces & chimneys are not warranted.

144 Patterson Road, Oakwood

Courtesy of Robert Wilson and Irongate Inc.
$284,000
2 Beds ⋅ 2 Baths ⋅ 965272 MLS ⋅ Teresa M Gustafson
Price Reduced ! Charming Oakwood Bungalow with Timeless Character & Valuable Updates Welcome home to this classic Oakwood bungalow, where historic charm meets modern peace of mind. Thoughtfully designed to maximize every square foot, the finished lower level significantly expands the living space, offering endless possibilities for a family room, home office, workout area, or guest retreat. The home features two generously sized bedrooms and two full bathrooms a rare convenience for a home of this era. Relax on the inviting front porch and enjoy the charm of this tree-lined Oakwood neighborhood. Inside, you'll appreciate the original hardwood floors, rich woodwork, and charming kitchen with abundant cabinetry, stainless steel appliances, and an adjoining dining room that's perfect for everyday meals or entertaining. Step outside to a fully fenced backyard with plenty of space to relax, entertain, or let pets play, plus an oversized detached garage with alley access and additional storage. Major improvements include custom replacement windows (2018) that preserve the home's original character, a new roof (2024), and a professionally installed interior drainage system by Concrete Pro (June 2026) with a lifetime transferable warranty. The finished basement was also refreshed in July 2026 with new waterproof luxury vinyl plank flooring and fresh paint. Conveniently located near parks, shopping, restaurants, and the Fraze Pavilion, this move-in-ready home offers the perfect combination of character, functionality, and lasting value.

344 Hadley Avenue, Oakwood

Courtesy of Teresa M Gustafson and Glasshouse Realty Group
$1,425,000
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
$514,900
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
$565,000
3 Beds ⋅ 4 Baths ⋅ 963698 MLS ⋅ Jerry A George
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
$650,000
5 Beds ⋅ 4 Baths ⋅ 958423 MLS ⋅ Sean Pleiman
Rare Oakwood Setting - This spacious, mint condition 5-bedroom, 3 Full Bathrooms 1 Half Bath Cape Cod sits on a stunning, meticulously maintained half-acre yard with beautifully tiered landscaping and vibrant seasonal blooms. Inside, you'll find generous living spaces including a welcoming Center Hall entrance, warm Living Room with gas fireplace, formal Dining Room, and a sunny Family Room with serene garden views. In addition, there is an informal Breakfast/Dining Room with secondary front door entrance. The fully equipped kitchen has a Thermador gas range, Thermador double electric ovens and solid surface counters. Two large first floor bedrooms are located on either side of an upgraded bathroom and complete the first floor. Upstairs, the three bedrooms include a generous Primary Bedroom Suite with upscale Bathroom. A third full Bathroom is shared by the other two bedrooms. The Full Basement is comprised of a finished Recreation Room with half Bathroom, along with a bright and immaculate Utility Room that has Storage and Workshop areas. The two car Garage has pull down Attic storage. The wonderful, expansive private rear patio looks up to stone wall terracing and gardens. Located on highly desirable W. Hadley Road, this home has been thoughtfully updated over the past 25 years of ownership, blending comfort, character, and care throughout. Truly an exceptional home and setting.

156 W Hadley Road, Oakwood

Courtesy of Sean Pleiman and Irongate Inc.
$549,000
4 Beds ⋅ 3 Baths ⋅ 957784 MLS ⋅ Jill Aldineh
Welcome to this stunning brick two-story home nestled among mature trees on well over a half-acre, located in the award-winning Oakwood school district. With over $100k in upgrades, this residence exudes elegance and charm. The main level features one of the four spacious bedrooms, ideal for guests or as a home office, along with a fully updated main bathroom showcasing chic black tile and high-end finishes. The inviting living room boasts a cozy fireplace, while large windows fill the home with natural light. The open-concept design seamlessly connects the living area to the large dining room, creating an ideal atmosphere for entertaining. A quaint sunroom with a wood-burning stone fireplace provides additional space for relaxing or gatherings. The chef’s dream kitchen is equipped with a top-of-the-line Thermador range, a pot-filling station, a stunning glass tile backsplash, white cabinetry, and elegant quartz countertops, complete with an inviting eat-in banquet area. Upstairs, you’ll find three additional large bedrooms, each offering generous storage space, and the primary bedroom features dual closets for added convenience. The hallway bathroom has been beautifully remodeled with a stylish wood dual vanity and clean lines, ensuring a streamlined and modern look. The spacious basement offers endless possibilities, featuring new carpeting and a fresh remodel that creates an inviting atmosphere. Enjoy the charm of the original built-in bar. Convenience abounds with a two-car garage equipped with a new garage door and a breezeway that enhances accessibility. New HVAC 2023 over $18k, Water Heater 2024, Water Softener 2023, Basement finishes, carpeting, ceiling 2024 over $ 20k, Garage Door 2021 $3k, Thermador 6 burner Pro-Harmony range $7500, Don’t miss the opportunity to make this exquisite home yours!

84 Thruston Boulevard, Oakwood

Courtesy of Jill Aldineh and RE/MAX Victory + Affiliates
$379,900
3 Beds ⋅ 3 Baths ⋅ 953596 MLS ⋅ Jill Aldineh
Welcome to this charming Oakwood beauty, ideally situated near UD and the vibrant downtown, and within a short distance of a cozy coffee shop and a variety of dining options. This home features an inviting front porch, perfect for relaxing afternoons. Inside the porch, discover beautiful hardwood floors and a welcoming entry that leads to a bright living room seamlessly connected to a spacious dining room ideal for large gatherings. A bonus sunroom offers a delightful space for reading or a serene home office. The character-filled kitchen is highlighted by a built-in breakfast nook, perfect for casual meals. The second level features three bedrooms, including a generously sized primary bedroom with dual closets. The hall bathroom has been tastefully updated, enhancing this home’s lovely appeal. Additionally, a walk-up attic presents the possibility for a fourth bedroom, providing extra space for your needs. Brand new roof with full tear-off (2026). This enchanting home is ready and waiting for its new owners to make it their own.

506 Volusia Avenue, Oakwood

Courtesy of Jill Aldineh and RE/MAX Victory + Affiliates
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