Vintage homes for sale & real estate in Highland Square, OH

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NEW 4 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Highland Square, OH:
Discover this wonderful condo at the Carlton House, conveniently situated across from Portage Country Club. This high-rise residence offers stunning views of the golf course throughout the year from its generous balcony. The main entrance leads to a spacious living room that is filled with bright natural light, thanks to the sliding glass doors. The kitchen provides plenty of workspace countertops, has a large pantry for storage, and comes complete with appliances. Both bedrooms provide ample storage and closet space, and are so large they can accommodate any size furniture. Additionally, the condo comes with a private storage room in the basement and a secure parking spot in the covered ga

$109,000

2 beds2 baths1,334 sq ft

275 N Portage Path Unit 7g, Akron, OH 44303

Private storage room • Generous balcony • Stunning views

OPEN SUN, 12:30PM TO 2PM

ABOUT THIS HOME
Vintage Home for sale in Highland Square, OH:
Fully renovated and ready to go! Come bear witness to this meticulously maintained centennial wonder, and you’ll see the best is yet to come! Situated in the heart of historic Highland Square and across the street from Hereford Park, this unique 3-4BR 1.5BA barn-style colonial showcases refinished hardwood floors through most of its 2300+ square feet! 1st floor features airy living room w/ bay window, brick gas fireplace & shiplap accent wall, adjacent to the sunroom w/ windows on two sides, spacious formal dining room for entertaining, updated eat-in kitchen w/ quartz counters, subway tile backsplash, SS appliances & double sink, gas range, built-in shoe bench, servant st

$285,000

3 beds1.5 baths2,333 sq ft

956 Wye Dr, Akron, OH 44303

Fully renovated • Quartz counters • Sunroom with windows

OPEN SAT, 1PM TO 3PM

ABOUT THIS HOME
Vintage Home for sale in Highland Square, OH:
Welcome home to this great condo in the Carlton House. Located across the street from Portage Country Club and on the fifth floor facing the golf course, you will have great views year round from the spacious balcony. The main entrance opens to a large living room with plenty of natural light coming in from the updated sliding glass doors to the balcony. Both bedrooms are large with ample storage. Newer stainless steal appliances, washer and dryer as well as a new furnace and hot water tank all have made this a move in ready condo. This condo includes a private storage room in the basement along with a secure parking spot. There is however plenty of overflow parking for family and guests on

$103,335

2 beds2 baths1,245 sq ft

275 N Portage Path Unit 5A, Akron, OH 44303

Private storage room • Secure parking spot • Spacious balcony

ABOUT THIS HOME
Vintage Home for sale in Highland Square, OH:
This is the house that you have been waiting for! Welcome home to 427 Kathleen Street. Nestled on a tucked away dead end street with a double lot in a highly sought after neighborhood, yet minutes from Highland Square and Cuyahoga Falls, and walking distance to King Elementary, this location cannot be beat, and offers plenty of space and privacy for you to enjoy. This stunning colonial exudes elegance and charm, and has been extensively updated from top to bottom! Upon entry you are greeted with an expansive living area that boasts tons of natural light and flows seamlessly into the dining room! The kitchen has been completely transformed offering all new cabinetry with tons of storage spac

$229,900

3 beds1 bath1,242 sq ft

427 Kathleen St, Akron, OH 44303

Added central air • All new electrical • Double lot

ABOUT THIS HOME
Vintage Home for sale in Highland Square, OH:
For Sale - 920 Bloomfield Ave 4 Bedrooms | 1.5 Bathrooms | Fully Updated Welcome home to this beautifully renovated 4-bedroom, 1.5-bath colonial! Located on Bloomfield Ave, this charming home blends classic character with modern updates, making it move-in ready for its next owner. Step inside to a bright, open layout featuring new flooring, fresh paint, and recessed lighting throughout. The spacious living room is highlighted by a decorative fireplace and flows seamlessly into the dining area and stunning updated kitchen. The kitchen boasts granite countertops, white shaker cabinets, tile backsplash, and stainless steel appliances – perfect for entertaining or everyday cooking. Upst

$174,900

4 beds1.5 baths1,417 sq ft

920 Bloomfield Ave, Akron, OH 44302

Decorative fireplace • Fully updated • Granite countertops

Property at 225 N Highland Ave, Akron, OH 44303, 4 beds, 2.5 baths

$289,900

4 beds2.5 baths1,801 sq ft

225 N Highland Ave, Akron, OH 44303

Property at 71 Dodge Ave, Akron, OH 44302, 5 beds, 2 baths

$149,900

5 beds2 baths1,920 sq ft

71 Dodge Ave, Akron, OH 44302

Property at 1066 Emma Ave, Akron, OH 44302, 4 beds, 2.5 baths

$140,000

4 beds2.5 baths1,708 sq ft

1066 Emma Ave, Akron, OH 44302

Property at 42 Belvidere Way, Akron, OH 44302, 3 beds, 1 bath

$174,999

3 beds1 bath1,572 sq ft

42 Belvidere Way, Akron, OH 44302

Property at 262 S Portage Path, Akron, OH 44302, 4 beds, 1 bath

$39,900

4 beds1 bath1,610 sq ft

262 S Portage Path, Akron, OH 44302

Property at 222 Rhodes Ave, Akron, OH 44302, 3 beds, 2 baths

$99,000

3 beds2 baths— sq ft

222 Rhodes Ave, Akron, OH 44302

Property at 141 Grand Ave, Akron, OH 44302, 3 beds, 1 bath

$95,000

3 beds1 bath— sq ft

141 Grand Ave, Akron, OH 44302

Property at 928 Bloomfield Ave, Akron, OH 44302, 3 beds, 1 bath

$70,000

3 beds1 bath1,463 sq ft

928 Bloomfield Ave, Akron, OH 44302

Property at 166 Marvin Ave, Akron, OH 44302, 3 beds, 2 baths

$162,500

3 beds2 baths1,008 sq ft

166 Marvin Ave, Akron, OH 44302

Property at 127 Hollinger Ave, Akron, OH 44302, 3 beds, 1 bath

$95,000

3 beds1 bath1,510 sq ft

127 Hollinger Ave, Akron, OH 44302

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ABOUT THIS HOME
Vintage Home for sale in Highland Square, OH:
Investment oppurtunity! This cosmetically updated single family home is leased for $1,295 per month through 06/14/26. Excellent choice for a seasoned or new investor seeking immediate rental income and a low-maintenance addition to their portfolio.

$115,000

4 beds1 bath1,457 sq ft

910 Bye St, Akron, OH 44320

4,617 sq ft lot • 2 garage spots • Somewhat walkable

ABOUT THIS HOME
Vintage Home for sale in Highland Square, OH:
Take a look at this freshly updated Colonial! Featuring three spacious bedrooms and one stylish bathroom, this charming residence provides character along with ample space and an abundance of natural light throughout the main level. As you enter, you're welcomed by an inviting L-shaped enclosed front porch. This space also features convenient washer and dryer hookups, adding functionality to your everyday living. The updated kitchen includes a single basin stainless steel sink, luxury vinyl flooring, a tile backsplash, and beautiful butcher block countertops. Exterior upgrades enhance the home’s appeal, with newly installed vinyl siding, a brand-new roof, and new gutters, providing pe

$89,900

3 beds1 bath1,184 sq ft

90 Nickel St, Akron, OH 44303

3,001 sq ft lot • Somewhat walkable

ABOUT THIS HOME
Vintage Home for sale in Highland Square, OH:
Completely Remodeled and ready to move in before the holidays! Endless counter space in the kitchen for cooking and gathering! Formal Dining Room with sliders to a small deck that goes to the fenced back yard! Living room has tons of natural lighting and a gas fireplace. Big enclosed front porch. Three bedrooms and an oversized full bathroom on the second floor. The third floor is the fourth bedroom. Full basement with tall ceilings! New furnace and HWT! Two car detached garage makes this home a terrific find!

$165,000

4 beds1.5 baths1,613 sq ft

434 Hillwood Dr, Akron, OH 44320

5,227 sq ft lot • 2 garage spots • Somewhat walkable

ABOUT THIS HOME
Vintage Home for sale in Highland Square, OH:
5 bedroom Finished attic totally remodeled home in 2024. Ready to move into. For sale alone or in package with 1005 Dewalt NW Canton, 1007 Dewalt NW Canton. Also completely rehabbed and code passed in 2025.

$110,000

5 beds2 baths2,664 sq ft

320 Wildwood Ave, Akron, OH 44320

6,250 sq ft lot • Garage • Somewhat walkable

ABOUT THIS HOME
Vintage Home for sale in Highland Square, OH:
Welcome to 366 Doyle Street, where modern style meets timeless charm. This beautifully renovated home has been completely redone from top to bottom, offering the perfect blend of comfort, function, and elegance. Step inside to discover brand-new flooring throughout, fresh paint, and 9-foot ceilings in the spacious living and dining rooms accented by coved crown molding. The brand-new kitchen is a showstopper—featuring soft-close white cabinetry, granite countertops, subway tile backsplash, and stainless steel appliances that shine beneath warm, modern lighting. The completely updated bathroom impresses with an oversized vanity topped with quartz, stylish finishes, and a fresh, modern

$149,900

3 beds1 bath1,593 sq ft

366 Doyle St, Akron, OH 44303

2,243 sq ft lot • Somewhat walkable

ABOUT THIS HOME
Vintage Home for sale in Highland Square, OH:
Welcome to this beautifully updated home located on the west side of Akron, just minutes from the Wallhaven area. This spacious 3-bedroom, 2-bathroom property combines modern updates with classic charm, offering comfortable living in a convenient location. Step inside to find a freshly remodeled interior with stylish finishes throughout. The main level features a bright living space, a nice size kitchen, and three comfortable bedrooms. Downstairs, the finished basement includes a full bathroom — perfect for a guest suite, home office, or additional living area. Enjoy outdoor living on the back patio deck, with a fully fenced backyard – ideal for pets, play, or entertaining. This

$289,999

3 beds2 baths1,650 sq ft

693 Roslyn Ave, Akron, OH 44320

7,261 sq ft lot • 2 garage spots • Somewhat walkable

Property at 478 Copley Rd, Akron, OH 44302, 4 beds, 1.5 baths

$155,000

4 beds1.5 baths2,374 sq ft

478 Copley Rd, Akron, OH 44302

Property at 462 Spaulding St, Akron, OH 44310, 3 beds, 2.5 baths

$67,000

3 beds2.5 baths1,332 sq ft

462 Spaulding St, Akron, OH 44310

Property at 888 Peckham St, Akron, OH 44320, 4 beds, 2 baths

$127,000

4 beds2 baths— sq ft

888 Peckham St, Akron, OH 44320

Property at 413 Crestwood Ave, Akron, OH 44302, 3 beds, 2 baths

$174,900

3 beds2 baths1,450 sq ft

413 Crestwood Ave, Akron, OH 44302

Property at 453 Briarwood Dr, Akron, OH 44320, 4 beds, 2 baths

$195,900

4 beds2 baths1,826 sq ft

453 Briarwood Dr, Akron, OH 44320

Property at 739 Roslyn Ave, Akron, OH 44320, 3 beds, 2.5 baths

$310,000

3 beds2.5 baths2,236 sq ft

739 Roslyn Ave, Akron, OH 44320

Property at 687 Moreley Ave, Akron, OH 44320, 3 beds, 1.5 baths

$187,900

3 beds1.5 baths1,570 sq ft

687 Moreley Ave, Akron, OH 44320

Property at 908 Stadelman Ave, Akron, OH 44320, 4 beds, 1 bath

$114,900

4 beds1 bath1,728 sq ft

908 Stadelman Ave, Akron, OH 44320

Property at 244 Crosby St, Akron, OH 44303, 3 beds, 3 baths

$149,950

3 beds3 baths1,946 sq ft

244 Crosby St, Akron, OH 44303

Property at 444 Evers St, Akron, OH 44310, 3 beds, 1 bath

$145,000

3 beds1 bath1,040 sq ft

444 Evers St, Akron, OH 44310

Property at 890 Work Dr, Akron, OH 44320, 4 beds, 2 baths

$115,000

4 beds2 baths— sq ft

890 Work Dr, Akron, OH 44320

Property at 900 Work Dr, Akron, OH 44320, 6 beds, 2 baths

$115,000

6 beds2 baths1,800 sq ft

900 Work Dr, Akron, OH 44320

Property at 617 Moreley Ave, Akron, OH 44320, 3 beds, 1.5 baths

$85,000

3 beds1.5 baths1,705 sq ft

617 Moreley Ave, Akron, OH 44320

Property at 533 Cuyahoga St, Akron, OH 44310, 3 beds, 1 bath

$114,999

3 beds1 bath1,544 sq ft

533 Cuyahoga St, Akron, OH 44310

Vintage Homes for Sale in Highland Square

There are currently 15 vintage homes for sale in Highland Square at a median listing price of $145K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Highland Square stay on the market for 38 days. Popular neighborhoods include Wallhaven, West Akron, Northwest Akron, Fairlawn Heights, and Merriman Valley. This map is refreshed with the newest listings in Highland Square every 15 minutes.

In the past month, 7 homes have been sold in Highland Square. In addition to houses in Highland Square, there was also 1 condo, 1 townhouse, and 2 multi-family units for sale in Highland Square last month. Highland Square is a moderately walkable neighborhood in Summit County with a Walk Score of 65. Highland Square is home to approximately 10,784 people and 2,817 jobs. Find your dream home in Highland Square using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Highland Square are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Highland Square. If you're looking to sell your home in the Highland Square area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Highland Square with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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