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$304,000

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.

2 Beds ⋅ 2 Baths ⋅ 965272 MLS ⋅ Teresa M Gustafson

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

$1,500,000

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.

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

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!

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

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!

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

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!

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

$360,000

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!

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.

$559,900

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.

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

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!

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