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101 Tipperary Lane, Winston-Salem
$275,000
4 Beds ⋅ 3 Baths ⋅ 1236069 MLS
101 Tipperary Ln is a single-story Winston-Salem home built in 1950, with four bedrooms, two full bathrooms and a half bathroom across 2,003 square feet of living area. The kitchen features cabinetry, stainless steel appliances and a tiled backsplash, opening to a dining area with a fireplace. A separate living room and hardwood flooring create distinct gathering spaces. The primary bedroom includes a walk-in closet and an adjoining bathroom with a shower. Set on a 9,583-square-foot lot, the home also has a backyard, a paved driveway and a detached storage building. Included 100-Day Home Warranty with buyer activation

101 Tipperary Lane, Winston-Salem

Listing courtesy of Opendoor Brokerage LLC. Contact:

4819 Gladwyn Drive, Winston-Salem
$385,000
3 Beds ⋅ 3 Baths ⋅ 1230780 MLS
Move-in ready with numerous recent updates and endless possibilities on a nearly 1-acre lot in Winston-Salem! Fresh LVP flooring, interior paint, updated kitchen countertops and backsplash, painted cabinetry, and a new cooktop give this home a refreshed feel. **The real standout is the lower level, offering its own private, step-free exterior entrance, full kitchen, living area, updated full bathroom, and flexible bedroom/office space!** Perfect for an in-law or guest suite, multigenerational living, or exploring rental income opportunities! Consider the potential for long-term tenants, traveling healthcare professionals, or short-term stays to help offset your mortgage payment, subject to applicable regulations and approvals. Extensive exterior clearing has opened up the spacious backyard, creating even more room to enjoy. Convenient to hospitals, medical facilities, shopping, dining, and major roadways. A unique opportunity offering space, flexibility, and income potential!

4819 Gladwyn Drive, Winston-Salem

Listing courtesy of Image Realty Group. Contact:

155 Monroe Street, Winston-Salem
$279,000
3 Beds ⋅ 2 Baths ⋅ 1228928 MLS
Welcome home to 155 Monroe Street! This generous 3-bedroom, 2-bath home offers main-level living with an upstairs bonus room [(not included in the total square footage (see agent only remarks)]. The kitchen opens up into a vaulted ceiling and would make a great area for entertaining. The primary suite features a private bath with a garden tub and skylight for extra light. Outside features a spacious backyard with plenty of room for entertaining. The home is within a short distance to shopping, restaurants and heathcare facilities.

155 Monroe Street, Winston-Salem

Listing courtesy of Keller Williams Realty Elite. Contact:

3634 Old Vineyard Road, Winston-Salem
$325,000
3 Beds ⋅ 2 Baths ⋅ 1227518 MLS

3634 Old Vineyard Road, Winston-Salem

Listing courtesy of NorthGroup Real Estate. Contact:

3817 Fritz Street, Winston-Salem
$206,500
2 Beds ⋅ 1 Baths ⋅ 1224260 MLS
Open House Tuesday, June 23 from 4-6 pm. Nestled among mature trees on a quiet street just off Country Club Road in the convenient South Fork area, this charming 1947 cottage offers character, comfort, and affordability. Featuring 2 bedrooms and 1 bath, the home blends timeless appeal with practical updates, including a roof & gutters replaced in 2020, low-maintenance vinyl siding, and gas heat. Beautiful hardwood floors add warmth throughout the home, while the spacious deck provides the perfect place to relax and enjoy the peaceful setting. The basement offers excellent storage, workshop space, or future possibilities. Conveniently located near shopping, dining, hospitals, parks, and major highways, you'll enjoy easy access to everything Winston-Salem has to offer. Whether you're a first-time buyer, downsizing, or investing, this affordable cottage is a wonderful opportunity.

3817 Fritz Street, Winston-Salem

Listing courtesy of Keller Williams Realty. Contact:

310 Meadows Circle, Winston-Salem
$130,000
2 Beds ⋅ 2 Baths ⋅ 1224599 MLS
Convenient, affordable, and updated! Home buyers and Investors take note! Well maintained by the current owners. Features include: New flooring, granite countertops and tiled backsplash in the galley kitchen, fresh paint, 9 foot ceilings, refreshed bathrooms, living room with fireplace and balcony access, 2nd bedroom with balcony, ensuite primary, and storage. Conveniently located off S Peace Haven Rd and Hwy 421! Schedule your showing today! See Agent Only.

310 Meadows Circle, Winston-Salem

Listing courtesy of Keller Williams Realty Elite. Contact:

4112 Country Club Road Unit #1034, Winston-Salem
$364,500
4 Beds ⋅ 3 Baths ⋅ 1214311 MLS
The Lenox floorplan offers approximately 2,548 sq ft, 4 bedrooms, and 2.5 bathrooms with upgraded features throughout. The main level includes an open-concept Great Room, Dining Area, private Study, and a well-appointed Kitchen with a large island and abundant cabinetry. 9’ ceilings on the first floor enhance the open feel. Upstairs, the Primary Suite features a private bath with dual vanities, tiled walk-in shower with transom window, garden tub, and a spacious walk-in closet. Additional highlights include a loft, secondary bedrooms, and a laundry room with folding table. Exterior features include an oversized 2-car garage and a 0.41-acre homesite with no HOA.

4112 Country Club Road Unit #1034, Winston-Salem

Listing courtesy of TLS Realty LLC. Contact:

4051 Gordon Court, Winston-Salem
$190,000
3 Beds ⋅ 2 Baths ⋅ 1201855 MLS
Welcome to this charming property that boasts a neutral color paint scheme throughout, giving it a modern and elegant touch. The kitchen is a chef's dream with all stainless steel appliances. Step outside to enjoy the patio in the back yard, perfect for entertaining or simply relaxing. The property also includes a storage shed for additional space. This home is a perfect blend of style and functionality. Don't miss out on this unique opportunity to own a home that combines comfort and convenience in one package.. Included 100-Day Home Warranty with buyer activation

4051 Gordon Court, Winston-Salem

Listing courtesy of Opendoor Brokerage LLC. Contact:

1076 Jonestown Road, Winston Salem
$343,900
3 Beds ⋅ 3 Baths ⋅ 4314083 MLS
• 3 Beds, 2.5 Baths • Spacious Mudroom • His-and-Hers Closets Discover the Durham floor plan at Sycamore Court in Winston-Salem—a thoughtfully crafted two-story home that blends timeless charm with modern comfort. Featuring 3 spacious bedrooms, 2.5 bathrooms, and elegant stone accents on the exterior, this home is designed to suit a variety of lifestyles. The open-concept main level creates a seamless flow between the kitchen, dining area, and family room—perfect for hosting guests or enjoying quiet evenings at home. A spacious mudroom located just off the garage entrance adds everyday convenience and helps keep things organized. Upstairs, the generous primary bedroom serves as a private retreat, complete with his-and-hers closets for ample storage and easy organization. Secondary bedrooms offer flexibility for a home office, nursery, or guest space. Large windows throughout the home invite abundant natural light, enhancing the warm and functional layout. Thoughtful details and a modern design ensure both comfort and style. Located in the desirable, family-friendly Sycamore Court community, the Durham offers convenient access to local parks, schools, shopping, dining, and major employers—making it an ideal place to call home.

1076 Jonestown Road, Winston Salem

Listing courtesy of LGI Homes NC LLC. msceau@lgihomes.com
1046 Jonestown Road, Winston Salem
$366,900
4 Beds ⋅ 3 Baths ⋅ 4314067 MLS
10 Minutes from Downtown Winston-Salem! 4 Bedrooms • Open-Concept Main Floor • Upstairs Laundry Convenient to All Bedrooms! The Davidson at Sycamore Court offers the perfect blend of modern design and everyday comfort in a prime Winston-Salem location. This spacious two-story home features an open-concept layout with a chef-ready kitchen complete with granite countertops, stainless steel appliances, and a large center island that opens to the dining and family rooms—perfect for entertaining or daily living. The thoughtfully designed floor plan provides the space and function today's homeowners need. Situated in the desirable Sycamore Court community, residents enjoy easy access to local parks, major employers, and area attractions, making this home as convenient as it is stylish.

1046 Jonestown Road, Winston Salem

Listing courtesy of LGI Homes NC LLC. msceau@lgihomes.com
1076 Jonestown Road, Winston-Salem
$343,900
3 Beds ⋅ 3 Baths ⋅ 1199553 MLS

1076 Jonestown Road, Winston-Salem

Listing courtesy of LGI HOMES NC, LLC. Contact:

1046 Jonestown Road, Winston-Salem
$366,900
4 Beds ⋅ 3 Baths ⋅ 1176270 MLS
Presenting the Davidson floor plan at Sycamore Court in Winston-Salem—this stylish 4-bedroom home offers the perfect blend of modern living and functionality. The open-concept design makes it ideal for hosting guests or enjoying time with family. The gourmet kitchen, featuring granite countertops, stainless steel appliances, and a generous island, effortlessly connects to the family room and dining area, creating a welcoming space for all. Located in the Sycamore Court community, this home provides convenient access to parks, major employers, and local attractions.

1046 Jonestown Road, Winston-Salem

Listing courtesy of LGI HOMES NC, LLC. Contact:

“ Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Some IDX listings have been excluded from this website. Properties may or may not be listed by the office/agent presenting the information © 2026 Canopy MLS as distributed by MLS GRID”

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The information from this search is provided by the High 'Country Multiple Listing Service. Please be aware that not all listings produced from this search will be of this real estate company. All information is deemed reliable, but not guaranteed. Please verify all property information before entering into a purchase.”

Listings provided courtesy of Triangle MLS, Inc. of NC, Internet Data Exchange Database. Information deemed reliable but not guaranteed. © 2026 Triangle MLS, Inc. of North Carolina. Data last updated .

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