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97 Shadylawn Drive, Winston-Salem
$474,900
4 Beds ⋅ 4 Baths ⋅ 1213434 MLS
Lovingly maintained 4-bedroom brick home in sought-after New Sherwood! A spacious dining room with classic wainscoting and a bay window sets the tone, while the formal living room opens beautifully to the entry. The kitchen features a large island peninsula with seating for six, plus a dining area that flows into the den—perfect for everyday living and entertaining. Enjoy the serene sunroom nestled among the trees, complete with plantation shutters. Upstairs offers four bedrooms. One bedroom is a flexible room connected to the primary suite—ideal for a nursery, office, or private owner’s retreat. The lower level provides exceptional versatility with a playroom, office, flex space, and full bath. Two-car garage. Conveniently located just minutes from highways, shopping, dining, and more!

97 Shadylawn Drive, Winston-Salem

3563 Milhaven Road, Winston-Salem
$469,900
3 Beds ⋅ 2 Baths ⋅ 1231461 MLS
Very nicely renovated Cape Cod in Sherwood Forest area. Was custom built for long-time Judge Harvey Lupton. Beautiful 1.27 acre lot slopes gently down to a stream in a wooded meadow. Wood floors throughout. Den could easily be a 4th BR. Statelyfir and knotty pine paneling in numerous rooms. Nice built-ins in some rooms. New decking and roof 2026. Refurbished kitchen with new stainless steel appliances. New LED lighting, fixtures, and GFI circuits. Newly refinished wood floors. Fresh paint throughout. New basement steps. Washer and dryer connections on main floor and in basement. New above-ground oil tank. New concrete floor front porch 2010. Most rooms are oversized. Tremendous potential finishable space in daylight basement.

3563 Milhaven Road, Winston-Salem

380 Hollinswood Avenue, Winston-Salem
$469,900
4 Beds ⋅ 4 Baths ⋅ 1226480 MLS
Welcome home to 380 Hollinswood Avenue in the sought after Ashford neighborhood! This beautiful brick home offers the perfect blend of space, comfort, and convenience. The oversized living room provides plenty of room to gather with family and friends, while the eat-in kitchen and formal dining room make everyday living and entertaining effortless. The spacious primary suite is a true retreat, complete with a private en suite bathroom featuring a large soaking tub and separate shower. Generously sized secondary bedrooms offer plenty of space for everyone. The finished basement is an entertainer's dream with a built-in bar, half bath, and endless possibilities for a game room, media room, or bonus living space. Step outside to the expansive back deck, perfect for grilling, relaxing, or hosting summer get-togethers. All of this in a convenient location close to shopping, dining, and everyday amenities—don't miss your chance to make this incredible home yours!

380 Hollinswood Avenue, Winston-Salem

3972 Poindexter Avenue, Winston-Salem
$464,900
4 Beds ⋅ 5 Baths ⋅ 1227028 MLS
Priced over 10K under apprised value! Ask your realtor about our incentives! Back on the market 10/2 at NO fault of seller. This inviting property features a bright, open layout w/ spacious living areas designed for both everyday living & entertaining. The kitchen offers ample cabinet & counter space, flowing seamlessly into the dining & living areas to create a warm & welcoming atmosphere. The generously sized bedrooms provide comfortable retreats, including a primary suite w/ a private space to relax & unwind. Basement is perfect for a multi stage family w/ den, bedroom & full bath ready for you adult kids or in-laws. Outside, enjoy a yard w/ room for gardening, play, entertaining, or simply enjoying the outdoors. Ideally located near Shattalon Lake, Chadwick Pool, shopping, dining & amazing Forsyth Co School system! Tons of updates to incl: NEW ROOF(under warranty), New deck, Tankless HWH, New HVAC on 2nd floor (all updates under 5 years old).

3972 Poindexter Avenue, Winston-Salem

9103 N NC Highway 109, Winston-Salem
$459,000
4 Beds ⋅ 3 Baths ⋅ 1237510 MLS
Fully remodeled mini-homestead on 3.75 private acres in Davidson County. This 4BR/2.5BA home boasts a skylit kitchen with SS appliances, soft-close cabinets, USB ports, and a main-level primary suite with walk-in closet and jetted tub. Upstairs features 2 bedrooms, full bath, and a den with multiple built-ins. Multi-zone inverter HVAC (new 2nd-floor system 2026), fresh paint, and an ~800 sq ft unfinished basement. Detached building boasts a finished, climate-controlled office plus a wired workshop! Outside enjoy a fenced yard, 32x16 deck, covered porch, 2 chicken coops, goat enclosure, covered grilling area, and invisible pet fence. The sale conveys a 2018 Jayco RV (sleeps 10), all kitchen appliances (new dishwasher), 2 washers, 2 dryers, and a 7-ft upright freezer! Additional adjacent 1-acre available as well . 1-yr home warranty included. Rare turnkey acreage backing up to Meadowlands! Sold as-is. Some photos have been virtually rendered.

9103 N NC Highway 109, Winston-Salem

852 Westover Avenue, Winston-Salem
$450,000
3 Beds ⋅ 3 Baths ⋅ 1239497 MLS
Charming Buena Vista home on almost half-acre cul-de-sac lot in sought after neighborhood! Features include beautiful hardwood floors, a primary suite with private bath, walk-in closet, and an adjoining library/office with built-in bookshelves, as well as a spacious eat-in kitchen with fireplace. Two additional bedrooms, one with a half bath, and separate full bath make this an ideal family home. Rounding out the floor plan are a generous open space with both a dining and living room with a fireplace, and a separate den. The large unfinished and dry basement offers added convenience and storage.  The floor plan is generous with a wonderful flow to the space and natural light in every room. Located just around the corner from Buie’s Market and Diamondback Grill, within an excellent public school district, the neighborhood also offers easy access to hospitals, shopping, and the interstate.

852 Westover Avenue, Winston-Salem

1236 Huntingdon Road, Winston-Salem
$450,000
3 Beds ⋅ 3 Baths ⋅ 1239444 MLS
Well maintained, one level home offering timeless character, beautiful hardwood floors throughout, and an abundance of storage. The spacious living room features a cozy fireplace and built-in shelving, while the heated and cooled sunroom provides the perfect spot to relax and enjoy the natural light. The vintage kitchen retains its original solid wood cabinetry and opens into the spacious den, creating a comfortable flow for everyday living and entertaining. The generously sized primary bath features a separate garden tub and shower, double vanity, and walk-in closet. Additional highlights include a two car garage with built in shelving and a workbench, a partial basement ideal for storage, and an attic with permanent stairs for easy access. Enjoy the backyard with a storage building featuring electricity, interior & exterior lighting, & pull-down attic storage. A major bonus of the property is the 50-year roof installed in 2021, with a transferable warranty.

1236 Huntingdon Road, Winston-Salem

1259 W 4th Street, Winston-Salem
$450,000
1230897 MLS
Turnkey investment opportunity in Winston-Salem’s historic West End! This fully furnished duplex has operated as a mid-term furnished rental since 2022 and as an Airbnb prior. Each unit offers 2 bedrooms, 1 full bath, and an in-unit washer and dryer. The upper/ground-level unit features central heating and air, while the lower unit is served by three mini-split systems, including a living room unit replaced in summer 2025. Roof replaced in 2025. Property is being sold fully furnished, offering the next owner flexibility for furnished, mid-term, or traditional rental use. Home could also be a great investment for someone looking to house hack into a fantastic neighborhood. Enjoy a prime West End location known for its tree-lined streets, historic architecture, parks, and convenient access to downtown Winston-Salem, dining, shopping, and area medical centers. Property is Agent owned.

1259 W 4th Street, Winston-Salem

1911 Margaret Street, Winston-Salem
$449,999
1198467 MLS
Turnkey opportunity to own an established salon in a convenient commercial location. Situated on a spacious 0.49-acre lot, this property offers an excellent opportunity for an owner-operator or investor looking to step into an existing salon setting, with the potential for immediate continued use. The property provides ample parking, easy access and a functional setup ready for a new owner to make it their own. Ideally located less than one mile from I-40 and approximately 11 minutes from downtown Winston-Salem, with close proximity to retail, dining, and surrounding businesses. Zoned GB, the property offers flexibility for future expansion or redevelopment, making this more than just a salon- it's an opportunity to own a well-positioned commercial property with long-term potential. A rare combination of an established salon, turnkey opportunity and commercial location. Call to schedule your appointment today! Owner Financing Available.

1911 Margaret Street, Winston-Salem

5299 Jacobs Way, Winston-Salem
$449,900
3 Beds ⋅ 2 Baths ⋅ 1238807 MLS
First time offering for sale since custom construction in 2005! Wonderfully maintained, move-in ready one-level home w/ bonus room in the desirable, convenient Prestwick neighborhood. Thoughtfully designed with an easy-flowing floor plan, generously sized rooms, upgraded kitchen cabinetry w/ granite countertops. The spacious primary suite offers a relaxing retreat with dual vanities, separate soaking tub/shower, and two large walk-in closets. Split-bedroom design provides excellent privacy for family and guests. Versatile room just off the kitchen can serve as a formal dining room, sunroom, or flexible living space. The inviting great room features a vaulted ceiling and gas fireplace, creating a warm and welcoming gathering space. The covered porch is perfect for entertaining or relaxing while overlooking the spacious backyard. New roof Spring 2026 and new carpet on the main level September 2026. A beautifully cared-for home ready for its next chapter! See Agent Only.

5299 Jacobs Way, Winston-Salem

125 Rannoch Court, Winston-Salem
$449,000
3 Beds ⋅ 2 Baths ⋅ 1238590 MLS
Huge Price improvement! -20k WOW! Rare opportunity. Exceptional setting with woods behind & common area across the street. This immaculate custom home combines upscale finishes with easy living— & an HOA that handles most exterior maintenance, including yard care & gutter cleaning. (maintenance chart in attachments) Inside, vaulted ceilings, beautiful light flooring & a lovely kitchen open to the great room create an inviting atmosphere. The soothing primary suite offers a relaxing retreat, while the upstairs bonus room features a striking barn door. Attic space provides additional storage. New efficient tankless water heater. Enjoy the covered front porch or unwind on the screened porch overlooking the rear patio & wooded backdrop. Four-sided brick construction, a two-car garage & move-in-ready. Neighborhood amenities include sidewalks, tennis and pickleball, with optional pool and golf memberships. A beautiful setting, convenient location and more time to enjoy it all! Come & See.

125 Rannoch Court, Winston-Salem

4814 Selwyn Drive, Winston-Salem
$445,000
4 Beds ⋅ 4 Baths ⋅ 1228119 MLS
New construction with custom charm! This brand new 4 bed, 3.5 bath home offers the perfect blend of style, comfort, and functionality. Step inside to a bright, open living space highlighted by vaulted ceilings and a stunning double-sided fireplace that seamlessly connects the living room and kitchen. The thoughtfully designed kitchen features a spacious island, gas cooktop, and dining area overlooking the spacious backyard, ideal for everyday living and entertaining. The main level primary suite serves as a peaceful retreat with a spa-inspired bath, walk-in double shower, and generous walk-in closet. Upstairs, you'll find three additional bedrooms, including a second primary suite, plus two full baths. Situated on over half an acre, the property also includes a dedicated workshop perfect for hobbies, storage, or creative projects. Conveniently located near shopping and dining, this move-in-ready home delivers the space, flexibility, and modern finishes you've been searching for!

4814 Selwyn Drive, Winston-Salem

6004 Santa Maria Drive, Winston-Salem
$445,000
3 Beds ⋅ 3 Baths ⋅ 1225335 MLS
A standout opportunity in Pioneer Estates, this beautifully refreshed ranch offers over 2,000 sq ft of effortless one-level living on a serene 1.4-acre homesite surrounded by mature trees. The interior has been thoughtfully revamped with new luxury plank flooring, updated bathrooms, and a reconfigured layout that expands the primary suite into an oversized retreat complete with a huge walk-in closet and en-suite bathroom. The newly upgraded kitchen features brand-new stainless steel appliances and a clean, modern feel that flows throughout the home. Fresh, neat, and truly move-in ready. Outside, you’ll find 2-car carport parking plus a 1-car detached garage—ideal for storage, a workshop, or conversion into the perfect hobby space or getaway. The property offers the best of both worlds: peaceful privacy just beyond the bustle, yet conveniently close to all the amenities Winston-Salem has to offer. A rare gem in a sought-after neighborhood.

6004 Santa Maria Drive, Winston-Salem

4926 Leinbach Drive, Winston-Salem
$443,900
5 Beds ⋅ 3 Baths ⋅ 1235944 MLS
PRICED TO SELL! Come see this 5 bedrooms and 2.5 bathrooms new build within the city limits of Winston-Salem. Designed with style and functionality in mind, this home offers a bright open-concept floor plan filled with natural light. The gourmet kitchen showcases stainless steel appliances, premium finishes, and space for cooking and entertaining. The main level includes a spacious living room with an accent wall, a guest bedroom and half bath. Luxury LVP flooring and plush carpet extend throughout the home. Upstairs, the primary suite offers a generous walk-in closet, spa-inspired ensuite, and dual vanities. Three additional bedrooms, a full bath with double sinks, and an upstairs laundry room complete the second floor. Enjoy the large rear deck, perfect for relaxing. A two-car garage and upscale finishes complete this move-in-ready home. Schedule your private showing today!

4926 Leinbach Drive, Winston-Salem

117 Marian Lane, Winston-Salem
$443,000
4 Beds ⋅ 3 Baths ⋅ 1230839 MLS
Located in Sherwood Forest, this open-concept home blends original character with modern functionality. Majorly renovated in 2019, it features refinished hardwood floors, abundant natural light, and an updated kitchen with generous workspace for cooking and entertaining. Three renovated full bathrooms and a finished basement with a bedroom, full bath, and bonus area provide flexible space for guests, a home office, or multigenerational living. A spacious deck and adjoining gravel fire pit area, extends the home’s gathering and entertaining space beyond the interior. The nearly half-acre lot is fenced on three sides and offers a balance of open lawn, shaded areas, established landscaping, as well year-round privacy plantings. A garden shed and expanded, refinished driveway add unique opportunities for practical storage and generous off-street parking. Agent is related to seller.

117 Marian Lane, Winston-Salem

5275 Jacobs Way, Winston-Salem
$440,000
3 Beds ⋅ 2 Baths ⋅ 1237183 MLS
Welcome to this beautifully maintained brick home in the sought-after Prestwick neighborhood! Designed primarily for single-level living with an upper-level bonus room, this home features a split-bedroom floor plan, low thresholds & spacious rooms. The vaulted living room with gas fireplace flows into a light-filled sunroom, creating an inviting space for everyday living and entertaining. The sunny eat-in kitchen offers ample cabinetry, Corian countertops and tile backsplash, with easy access to both the sunroom and large rear deck with retractable awning. The primary suite features a tray ceiling, two closets and en-suite bath with double vanities & walk-in shower. Generously sized secondary bedrooms provide plenty of flexibility for guests or a home office. Major updates include a 2022 roof and 2025 heating & cooling system. Enjoy a low HOA and convenient access to dining, shopping, schools and everyday amenities.

5275 Jacobs Way, Winston-Salem

3915 Chadwyck Court, Winston-Salem
$439,990
5 Beds ⋅ 4 Baths ⋅ 1239866 MLS
Discover this spacious 5-bedroom, 3.5-bath home in the Chadwyck community of Winston-Salem. Features include an open floor plan, two-story foyer, main-level primary suite, kitchen with granite countertops and stainless steel appliances, and a gas-log fireplace. Upstairs offers 4 additional bedrooms and a versatile bonus room. Bedrooms 2 and 3 have a shared full bath with dual vanities. Enjoy a large deck overlooking a landscaped yard with fruit trees and a creek. Additional highlights include a mudroom, laundry connections on both levels, an attached 2-car garage, and access to the neighborhood pool. Conveniently situated on a cul-de-sac across from the Chadwyck Club's wooded setting. Updates include HVAC (2024) and water heater (2026).

3915 Chadwyck Court, Winston-Salem

2460 Dog Leg Drive, Winston-Salem
$439,900
4 Beds ⋅ 4 Baths ⋅ 1235962 MLS
Welcome home to this stunning, exceptionally spacious 4-bedroom, 3.5-bathroom single-family residence offering 3,165 square feet of pristine living space. Nestled in a convenient Winston-Salem location, this property perfectly combines modern comfort with everyday functionality. Step inside to discover an inviting, open-concept main floor designed for effortless entertaining and daily living. Upstairs, you will find generous bedroom accommodations, including a tranquil primary suite designed as a true private retreat. Enjoy ultimate convenience just minutes away from local hospitals, premier dining, and shopping hubs. Residents also gain access to fantastic neighborhood amenities, including community sidewalks and a refreshing neighborhood pool. Don't miss your chance to own this gorgeous Forsyth County home! Schedule your private showing today.

2460 Dog Leg Drive, Winston-Salem

106 Bishop Street, Winston-Salem
$439,000
3 Beds ⋅ 3 Baths ⋅ 1226665 MLS
Big Price Reduction. Motivated Seller. This gem was built in 1955, but might as well be new. Totally updated and remodeled within the last few years. Located on a large, beautiful corner lot. The oversized two car garage was added along with an extra large workshop. Owner is a licensed general contractor and has gone above and beyond to make his personal home fabulous and unique. You will love the screened in porch and spacious deck off the main level above the garage. Lower level would make a perfect in-law or teen suite with it's own kitchenette. Two wood burning fireplaces, one on main level and lower level. Too many extras and custom features to list here. Please see attached disclosure with full list of work done since 2018. One bedroom and another bonus room on lower level that could be used as an office, fitness room, craft room and has been used as a 4th bedroom. You don't want to miss this home!

106 Bishop Street, Winston-Salem

1016 Fenimore Street, Winston-Salem
$439,000
3 Beds ⋅ 3 Baths ⋅ 1224948 MLS
Fantastic opportunity in the heart of Ardmore. 1016 Fenimore is sure to impress with an incredible kitchen featuring an abundance of granite counter space, classic white cabinetry, stainless steel appliances, a gorgeous tile backsplash, oversized island, spacious pantry, and a cozy breakfast area perfect for everyday living. The main level offers a warm and inviting layout with generously sized living and dining spaces, beautiful hardwood floors, and a gas log fireplace. The outdoor living space is truly a standout, featuring a screened porch, deck, covered patio, and fully fenced backyard — perfect for entertaining, relaxing, or enjoying the outdoors. The basement offers endless possibilities with a massive bonus room, dedicated workshop space, and convenient garage access. Don’t miss the thoughtfully updated bathrooms and all the charm this Ardmore gem has to offer. With a brand new 2026 HVAC and furnace! This one is a must-see!

1016 Fenimore Street, Winston-Salem

2858 Eland Drive, Winston-Salem
$436,900
4 Beds ⋅ 4 Baths ⋅ 1236042 MLS
Beautiful New Construction in Winston Salem on 1/2 acre lot ... Kitchen offering massive countertop space, soft closed cabinets, granite countertops, stainless/black appliances, pantry, gray shaker cabinetry - 42 inch cabinets..Spacious Breakfast Area & Formal Dining room...Two story foyer...Living Room has plenty of space for any of your furniture desires and a gas log fireplace too with tile surround... Hall Coat Closet.. 1/2 bath with custom vanity ... Upper level offers 4 bedrooms, Laundry Room and Hall Linen Closet...Spacious Primary Bedroom with Walk in Closet .. Beautiful Primary Bathroom with oversized, tiled surround, soaker tub/shower combo, Double Vanity, Tile Flooring, Privacy Toilet Closet... Secondary 'primary' bedroom with attached full bathroom with tub/shower combo ... Two additional bedrooms with hall bathroom with tub/shower combo...LVP throughout, Gas Water Heater, Oversized Garage with EV Charger already installed...13 x 12 back patio

2858 Eland Drive, Winston-Salem

4840 Spilsby Lane, Winston-Salem
$435,000
3 Beds ⋅ 3 Baths ⋅ 1238948 MLS
Welcome home to 4840 Spilsby Lane, tucked on a quiet street in the beautiful Sherwood Forest neighborhood! This charming brick ranch has all the makings of your dream home, with the convenience of main-level living and a beautiful fenced backyard perfect for relaxing or entertaining on the back deck. Inside, enjoy a sunny living room, cozy den, and gorgeous open kitchen that serves as the heart of the home. The primary suite offers a private en suite bath, while the basement provides even more possibilities with a bonus room and recreation space perfect for hobbies, a home gym, or movie nights. Complete with a one-car garage plus extra unfinished storage space and plenty of charm, this home is one you won't want to miss. Schedule your showing today!

4840 Spilsby Lane, Winston-Salem

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