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$299,900

ATTENTION! One of Oakwood’s best values for a three-bedroom, two full bath home, with more than 2,000 square feet of living space! This charming brick home features an inviting living room with a fireplace, stainless steel kitchen appliances, a spacious upstairs primary suite with a private bath, and a finished lower-level family room. Outside, enjoy the 2025 backyard patio, mature trees, and detached garage. Major improvements include a new sewer line, main roof, gutters, gutter guards, and chimney lining and cap in 2024; garage roof in 2021; and whole-house plumbing and a fireplace insert in 2020. So sit back, enjoy the weather, and have peace of mind, knowing the major stuff is already taken care of!

3 Beds ⋅ 2 Baths ⋅ 967530 MLS ⋅ Zachary Baird

ATTENTION! One of Oakwood’s best values for a three-bedroom, two full bath home, with more than 2,000 square feet of living space! This charming brick home features an inviting living room with a fireplace, stainless steel kitchen appliances, a spacious upstairs primary suite with a private bath, and a finished lower-level family room. Outside, enjoy the 2025 backyard patio, mature trees, and detached garage. Major improvements include a new sewer line, main roof, gutters, gutter guards, and chimney lining and cap in 2024; garage roof in 2021; and whole-house plumbing and a fireplace insert in 2020. So sit back, enjoy the weather, and have peace of mind, knowing the major stuff is already taken care of!

406 Triangle Avenue, Oakwood

Courtesy of Zachary Baird and Keynote Realty

$525,000

Welcome to 19 Lookout Dr. This elegant colonial is a show stopper! Upon arrival, you'll be greeted by the stunning facade, well manicured landscaping and secluded lot. Approaching from the charming, stone walkway, the covered, two tiered front porch/patio with relaxing porch swing will invite you to explore what this home has to offer! Once inside, the gleaming hardwood flooring flows throughout the first floor, bringing you into the spacious living room with wood burning fireplace. The living room opens to both the formal dining room and the renovated kitchen. Heading into the dining room, you'll find amazing views of the secluded back yard. The renovated kitchen features stainless steel appliances, pegged hardwood flooring, newer cabinets, granite countertops and a eat-in area. From the other side of the dining room, you'll find the first floor bedroom/office, full bathroom, hallway with built-ins and an enclosed porch filled with windows overlooking the private lot. Upstairs features a landing which opens to an office or reading nook overlooking the back yard, a hallway that leads to the 4 second floor bedrooms and 2nd full bathroom. The bedrooms feature radiant hardwood flooring and ample light. Three of the four bedrooms are impressively large! The primary bedroom features double closets for added storage! The walk out basement offers massive potential if someone wants to finish the lower level. The basement boasts the large laundry room, a canning room, a large utility room that opens to a spacious rec room and extra storage room. Access to the attached garage is through the basement and features storage and an automatic opener. Outside, the property features a long wrap around driveway that leads to the rear of the home. The vast yard offers room for enjoyment, gardening, family gatherings and much, much more! Don't wait on this one, it will be snatched up quickly! Call for a private tour today!

4 Beds ⋅ 2 Baths ⋅ 967392 MLS ⋅ Stephen S Payne

Welcome to 19 Lookout Dr. This elegant colonial is a show stopper! Upon arrival, you'll be greeted by the stunning facade, well manicured landscaping and secluded lot. Approaching from the charming, stone walkway, the covered, two tiered front porch/patio with relaxing porch swing will invite you to explore what this home has to offer! Once inside, the gleaming hardwood flooring flows throughout the first floor, bringing you into the spacious living room with wood burning fireplace. The living room opens to both the formal dining room and the renovated kitchen. Heading into the dining room, you'll find amazing views of the secluded back yard. The renovated kitchen features stainless steel appliances, pegged hardwood flooring, newer cabinets, granite countertops and a eat-in area. From the other side of the dining room, you'll find the first floor bedroom/office, full bathroom, hallway with built-ins and an enclosed porch filled with windows overlooking the private lot. Upstairs features a landing which opens to an office or reading nook overlooking the back yard, a hallway that leads to the 4 second floor bedrooms and 2nd full bathroom. The bedrooms feature radiant hardwood flooring and ample light. Three of the four bedrooms are impressively large! The primary bedroom features double closets for added storage! The walk out basement offers massive potential if someone wants to finish the lower level. The basement boasts the large laundry room, a canning room, a large utility room that opens to a spacious rec room and extra storage room. Access to the attached garage is through the basement and features storage and an automatic opener. Outside, the property features a long wrap around driveway that leads to the rear of the home. The vast yard offers room for enjoyment, gardening, family gatherings and much, much more! Don't wait on this one, it will be snatched up quickly! Call for a private tour today!

19 Lookout Drive, Oakwood

Courtesy of Stephen S Payne and Keller Williams Community Part

$284,000

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.

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

$285,000

Welcome home to this charming Oakwood classic where timeless character meets today's lifestyle. Located in the highly desirable Oakwood School District, this home offers 2 bedrooms plus a versatile second-story loft currently configured as a home office that could also serve as a third bedroom, 1.5 bathrooms, 1,452 square feet of living space, and a semi-finished full basement. Original details—including hardwood floors, crown molding, the original front door, fireplace, and inviting covered front porch—blend seamlessly with thoughtful updates throughout. The sun-filled living room opens to the dining room, creating comfortable gathering spaces, while the updated eat-in kitchen features granite countertops, stainless steel appliances, retro cabinetry, luxury vinyl tile flooring, an exposed brick chimney, and a cozy breakfast nook. Upstairs, the flexible loft provides an ideal work-from-home space or reading area, while the original hardwood flooring remains beneath the carpet in the bedrooms. The finished basement expands the home's functionality with an additional living area, half bath, laundry, and generous storage. Enjoy relaxing on the covered front porch, entertaining on the rear deck, or spending time in the fenced backyard. Additional features include updated windows, recently painted exterior, and a detached 1.5-car garage. One of this home's standout features is its location. Enjoy the convenience of nearby shopping and dining, with parks, the library, schools, and everyday amenities just a short walk away. If you're looking for classic Oakwood charm, flexible living spaces, and a location that makes it easy to enjoy the neighborhood, this home is one you won't want to miss.

2 Beds ⋅ 2 Baths ⋅ 963537 MLS ⋅ Tammy Murphy

Welcome home to this charming Oakwood classic where timeless character meets today's lifestyle. Located in the highly desirable Oakwood School District, this home offers 2 bedrooms plus a versatile second-story loft currently configured as a home office that could also serve as a third bedroom, 1.5 bathrooms, 1,452 square feet of living space, and a semi-finished full basement. Original details—including hardwood floors, crown molding, the original front door, fireplace, and inviting covered front porch—blend seamlessly with thoughtful updates throughout. The sun-filled living room opens to the dining room, creating comfortable gathering spaces, while the updated eat-in kitchen features granite countertops, stainless steel appliances, retro cabinetry, luxury vinyl tile flooring, an exposed brick chimney, and a cozy breakfast nook. Upstairs, the flexible loft provides an ideal work-from-home space or reading area, while the original hardwood flooring remains beneath the carpet in the bedrooms. The finished basement expands the home's functionality with an additional living area, half bath, laundry, and generous storage. Enjoy relaxing on the covered front porch, entertaining on the rear deck, or spending time in the fenced backyard. Additional features include updated windows, recently painted exterior, and a detached 1.5-car garage. One of this home's standout features is its location. Enjoy the convenience of nearby shopping and dining, with parks, the library, schools, and everyday amenities just a short walk away. If you're looking for classic Oakwood charm, flexible living spaces, and a location that makes it easy to enjoy the neighborhood, this home is one you won't want to miss.

336 Peach Orchard Avenue, Oakwood

Courtesy of Tammy Murphy and R H 2 L

$319,900

Welcome home to this charming classic two-story offering 2 bedrooms and 2 full bathrooms in one of the area's most desirable neighborhoods! Rich hardwood floors add timeless character, while the bright and inviting sunroom provides the perfect space to enjoy your morning coffee, relax with a book, or entertain guests. The functional floor plan features two spacious bedrooms and a full bath on the upper level, with a second full bathroom located in the full unfinished basement—offering endless possibilities for additional living space, a recreation room, home gym, or workshop. Step outside to discover an adorable backyard, perfect for gardening, pets, family gatherings, or simply unwinding after a long day. A one-car garage provides added convenience and storage. Location is everything, and this home delivers! Situated in a highly sought-after area of town, you'll enjoy the convenience of walking to schools, parks, shopping, and everyday amenities. Classic charm, an unbeatable location, and room to make it your own—don't miss the opportunity to call this wonderful home yours. Schedule your private showing today!

2 Beds ⋅ 2 Baths ⋅ 962443 MLS ⋅ Rhonda Hunter

Welcome home to this charming classic two-story offering 2 bedrooms and 2 full bathrooms in one of the area's most desirable neighborhoods! Rich hardwood floors add timeless character, while the bright and inviting sunroom provides the perfect space to enjoy your morning coffee, relax with a book, or entertain guests. The functional floor plan features two spacious bedrooms and a full bath on the upper level, with a second full bathroom located in the full unfinished basement—offering endless possibilities for additional living space, a recreation room, home gym, or workshop. Step outside to discover an adorable backyard, perfect for gardening, pets, family gatherings, or simply unwinding after a long day. A one-car garage provides added convenience and storage. Location is everything, and this home delivers! Situated in a highly sought-after area of town, you'll enjoy the convenience of walking to schools, parks, shopping, and everyday amenities. Classic charm, an unbeatable location, and room to make it your own—don't miss the opportunity to call this wonderful home yours. Schedule your private showing today!

300 Wiltshire Boulevard, Oakwood

Courtesy of Rhonda Hunter and Irongate Inc.

$445,000

Lovingly cared for by the same owner for almost 40 years, this exceptional Oakwood residence seamlessly blends timeless character with thoughtful modern updates. Offering more than 2,200 square feet of living space, this spacious home features 5 bedrooms, 2 beautifully remodeled bathrooms, and an ideal location in the heart of Oakwood. From the moment you enter, you'll appreciate the home's original picture molding, abundant natural light, fresh paint, new carpeting, and elegant new chandeliers and recessed lighting. The versatile floor plan includes both a formal living room and a comfortable family room on the main level, along with a first-floor full bathroom—perfect for guests or multi-generational living. The updated kitchen is designed for both everyday living and entertaining, featuring brand-new appliances installed in 2026, ample workspace, and an adjoining dining and eat-in area that creates a welcoming gathering space for family and friends. Extensive improvements provide peace of mind for years to come, including a newer HVAC system, newer hot water heater, newer windows, whole-house siding, updated electrical system, new garage door (2026), new skylight (2026), and sump pump (2026). The roof was replaced in 2014, with the garage roof completed in 2013. Rarely does a home combine this level of space, character, location, and investment in updates. Move-in ready and Seller has purchased top of the line Home warranty for the new buyer the home has passed Oakwood Occupancy inspection, this is a wonderful opportunity to own a truly special Oakwood home. The fireplace (nonoperational) and chimney are not warranted and will convey in as-is condition. Seller has already passed Oakwood Presale Inspection.

5 Beds ⋅ 2 Baths ⋅ 957653 MLS ⋅ Emily Pelligra

Lovingly cared for by the same owner for almost 40 years, this exceptional Oakwood residence seamlessly blends timeless character with thoughtful modern updates. Offering more than 2,200 square feet of living space, this spacious home features 5 bedrooms, 2 beautifully remodeled bathrooms, and an ideal location in the heart of Oakwood. From the moment you enter, you'll appreciate the home's original picture molding, abundant natural light, fresh paint, new carpeting, and elegant new chandeliers and recessed lighting. The versatile floor plan includes both a formal living room and a comfortable family room on the main level, along with a first-floor full bathroom—perfect for guests or multi-generational living. The updated kitchen is designed for both everyday living and entertaining, featuring brand-new appliances installed in 2026, ample workspace, and an adjoining dining and eat-in area that creates a welcoming gathering space for family and friends. Extensive improvements provide peace of mind for years to come, including a newer HVAC system, newer hot water heater, newer windows, whole-house siding, updated electrical system, new garage door (2026), new skylight (2026), and sump pump (2026). The roof was replaced in 2014, with the garage roof completed in 2013. Rarely does a home combine this level of space, character, location, and investment in updates. Move-in ready and Seller has purchased top of the line Home warranty for the new buyer the home has passed Oakwood Occupancy inspection, this is a wonderful opportunity to own a truly special Oakwood home. The fireplace (nonoperational) and chimney are not warranted and will convey in as-is condition. Seller has already passed Oakwood Presale Inspection.

338 Forrer Boulevard, Oakwood

Courtesy of Emily Pelligra and Coldwell Banker Heritage