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$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
$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
$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
$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
$295,000
3 Beds ⋅ 2 Baths ⋅ 963760 MLS ⋅ Erin Kristbaum
Welcome to this charming Oakwood home just blocks from the heart of the community, offering easy access to coffee shops, restaurants, parks, and local shopping. This beautifully updated residence features a welcoming front porch, gleaming hardwood floors throughout, and an abundance of natural light that fills every room. The thoughtfully designed layout provides first-floor bedrooms and bathrooms for convenient single-level living, while the upstairs owner's suite serves as a private retreat complete with a spacious walk-through closet and full bathroom. The freshly updated kitchen showcases crisp white cabinetry, sleek black countertops, herringbone tile backsplash, and stainless steel appliances including refrigerator, range/oven, dishwasher, and microwave—all included with the sale. A decorative brick fireplace adds warmth and character to the main living area, and elegant arched doorways enhance the home's classic appeal. Step outside to the newly added deck, perfect for relaxing, entertaining, and enjoying outdoor meals in the fenced backyard. Additional features include a full basement offering ample storage and a detached two-car garage. Located within the highly regarded Oakwood City School District, this move-in-ready home combines timeless charm with modern updates in a walkable neighborhood. Some photos have been virtually staged to help you envision the possibilities.

2105 Shroyer Road, Oakwood

Courtesy of Erin Kristbaum and CENTURY 21 The Gene Group
$575,000
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
$360,000
3 Beds ⋅ 2 Baths ⋅ 961880 MLS ⋅ Peter Davies
This Oakwood gem is an absolute charmer! Enter through the double front doors beneath the stately portico and step into the entry room with its elegant, curving staircase.The entire home is filled with natural light filtering through custom, slatted blinds. The dining room has an outside/inside feel thanks to the windows and door that open onto the terrace and backyard. The kitchen wall has been opened up to make a perfect connection to the dining room, and a greenhouse window over the sink keeps the kitchen bright and sunny. The main floor also includes one bedroom and a nearby half bathroom. It’s also very suitable for a study or home office. Ascend the curving staircase to the second floor landing and find two generously sized bedrooms and a luxuriously updated bathroom, complete with a soaking tub and separate shower. [1] The finished basement with a gas log fireplace and a dining area with custom cabinetry is a perfect addition to the living space. Outside, the landscaped backyard offers a tiled terrace, gazebo, BBQ area, raised beds, rock garden, and an herb garden with plenty of delicious tomatoes ready for the new owners!

360 East Drive, Oakwood

Courtesy of Peter Davies and Irongate Inc.
$335,000
3 Beds ⋅ 2 Baths ⋅ 961475 MLS ⋅ Toni Donato Shade
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
$850,000
4 Beds ⋅ 5 Baths ⋅ 960407 MLS ⋅ Kamela Kordik
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
$559,900
4 Beds ⋅ 4 Baths ⋅ 959194 MLS ⋅ Joanne Cronin
Offering this beautifully crafted brick Tudor built in 1983 and located in the coveted Golden Triangle of Oakwood, this custom-built residence blends timeless architecture with the comfort and functionality today's buyers desire. Featuring approximately 2,969 square feet, 4 bedrooms, and 3.5 baths, the home offers exceptional space for both everyday living and elegant entertaining. A dramatic two-story foyer welcomes you inside, where hardwood floors, refined formal spaces, and abundant natural light create an atmosphere of warmth and sophistication. The remodeled eat-in kitchen showcases granite countertops, updated cabinetry, and seamless flow into the inviting family room anchored by a striking stone fireplace and custom built-ins. Upstairs, 4 spacious bedrooms and three full baths provide flexibility for family, guests, or work-from-home living, while an additional bonus room with private balcony offers endless possibilities as a study, playroom, or fifth bedroom. Outdoor living is equally impressive with a covered patio ideal for entertaining, relaxing evenings, or morning coffee overlooking the beautifully maintained grounds. Previous updates including roof, gutters, and water heater add peace of mind, while the attached two-car garage and finished lower-level recreation space complete the home's exceptional appeal. Perfectly positioned near schools, parks, and the community center, this is a rare opportunity to own a distinctive Oakwood property that combines character, location, and lifestyle.

215 Beverly Place, Oakwood

Courtesy of Joanne Cronin and Irongate Inc.
$499,900
4 Beds ⋅ 4 Baths ⋅ 957698 MLS ⋅ Mike Temple
Nestled in the highly sought-after community of Oakwood and within walking distance of award-winning schools, this custom-built two-story home is situated on a rare double lot surrounded by mature trees and lush landscaping, pavered patio area, offering exceptional privacy, space, and location. Built with quality craftsmanship in 1978, features over 2,700 square feet of living space, plus a fully finished basement, providing ample room for both everyday living and entertaining. From the moment you enter, you'll appreciate the home's solid construction, timeless design, and opportunity to add your own personal style. The home offers multiple spacious living areas, highlighted by two wood-burning fireplaces with blowers that create a warm and inviting atmosphere. Andersen wood windows fill the interior with natural light, including a stunning bay window in the breakfast area overlooking the picturesque backyard and a charming box window in the family room accented by custom built-in bookshelves. The generously sized kitchen is designed for both functionality and gathering, featuring abundant cabinetry, extensive counter space, and all appliances included. A formal dining room provides the perfect setting for holiday celebrations, family dinners, and entertaining guests. The expansive primary suite serves as a private retreat, offering plenty of room for furnishings, a large 11' x 7' walk-in closet, and a beautifully updated bath complete with a custom ceramic-tiled shower. The fully finished basement offers incredible versatility and can easily accommodate a recreation room, media center, game room, fitness area, or play space. Recent improvements include a complete roof w/ tear off (2023), new carpet in the living room, dining room, staircase, and primary bedroom, as well as a new water heater (2023). Spacious floor plan, this home presents a wonderful opportunity to personalize and build equity in one of the area's most desirable neighborhoods. A must see!

317 Greenmount Boulevard, Oakwood

Courtesy of Mike Temple and RE/MAX Alliance 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.
$574,900
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
$895,000
5 Beds ⋅ 5 Baths ⋅ 954935 MLS ⋅ Eric Weimer
A stunning residence designed to impress, this immaculate Italianate-style colonial exudes timeless elegance. Boasting five bedrooms and five bathrooms across three stories, including a finished basement and an attached two-car garage with a newer driveway, this home combines grandeur with practicality. Before stepping inside, your attention will be drawn to the expansive yard, a charming porch with curved arches and wood beams, and a distinctive rounded front door that sets the tone for the home's character. Upon entering, the foyer welcomes you with a graceful curved staircase crowned by a classic chandelier. Adjacent to the foyer is a spacious living room featuring soaring ceilings, original wood flooring, a cozy fireplace, and a sunroom adorned with a green tiled fountain—an original feature of the home. Large windows and French doors flood the interior with natural light, enhancing the home's inviting atmosphere. The generous eat-in kitchen has been thoughtfully updated, offering double ovens and stainless steel appliances for modern convenience. The primary suite is a retreat in itself, showcasing beautiful wood beams, a renovated full bathroom, and a double-entry sitting room. Throughout the residence, character and sophistication blend seamlessly, creating a perfect harmony of historic charm and contemporary updates. Located in the heart of Oakwood, this exceptional home is a true treasure.

25 W Thruston Boulevard, Oakwood

Courtesy of Eric Weimer and Glasshouse Realty Group
$399,900
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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