Cloister Oaks Real Estate

Welcome to Cloister Oaks, a charming subdivision nestled in the heart of Winston-Salem, North Carolina. This vibrant community offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike.

Cloister Oaks is characterized by its beautifully landscaped streets, where mature trees and well-maintained gardens create an inviting atmosphere. The homes here showcase a variety of architectural styles, from classic brick facades to modern designs, catering to diverse tastes and preferences. Each property is thoughtfully designed, offering spacious layouts and ample outdoor space, perfect for entertaining or enjoying quiet evenings at home.

Residents of Cloister Oaks enjoy easy access to a wealth of amenities. Just a short drive away, you'll find a plethora of shopping options, dining establishments, and recreational facilities. The nearby Hanes Mall is a shopper's paradise, while local restaurants serve up everything from Southern comfort food to international cuisine. For outdoor enthusiasts, the area is dotted with parks and green spaces, providing opportunities for hiking, picnicking, and enjoying nature.

Cloister Oaks is also conveniently located near major highways, making commutes to downtown Winston-Salem and surrounding areas a breeze. The community is served by top-rated schools, ensuring that families have access to quality education.

Experience the warmth and charm of Cloister Oaks, where a friendly community atmosphere meets the conveniences of modern living. Come explore your new home in this delightful Winston-Salem neighborhood today!

Newest Listings in Cloister Oaks

$289,000

4 Beds ⋅ 3 Baths ⋅ 1229500 MLS

Welcome home to this spacious property offering room to spread out, both inside and out! The inviting eat-in kitchen provides the perfect gathering space for everyday living and entertaining. Downstairs, you'll find an expansive unfinished basement currently being used as additional living space, offering incredible flexibility for a recreation room, home gym, office, or hobby area (not included in the heated square footage). Car enthusiasts, hobbyists, or those needing extra storage will appreciate the two garages, while the beautiful 1+ acre lot provides plenty of outdoor space for gardening, play, or simply enjoying the peaceful surroundings. Conveniently located with no HOA, this home offers endless possibilities to make it your own. Schedule your private showing today!

4365 Wakeman Drive, Winston-Salem

$139,900

2 Beds ⋅ 2 Baths ⋅ 1227999 MLS

Move right into this beautifully updated second level condo featuring 2 bedrooms and 2 full baths. Fresh paint, new flooring, and modern updates throughout make this home truly move in ready. You will love the vaulted ceilings, spacious covered deck, and functional layout. The refrigerator, washer, and dryer all convey, making your move even easier. If you are looking for affordable, low maintenance living in Winston Salem, this one is a must see!

116 Cloister Oaks Circle, Winston-Salem

$104,900

2 Beds ⋅ 1 Baths ⋅ 1223400 MLS

Nestled in a quiet, secluded community just off Silas Creek Parkway, this condo offers comfort, convenience, and value. Enjoy spacious rooms, a clean, well maintained interior and a private porch perfect for relaxing with your morning coffee or unwinding at the end of the day. Conveniently located close to shopping, restaurants, medical facilities and I-40, this home places everyday necessities just minutes away. Spend your summers cooling off at the neighborhood pool while enjoying the peaceful setting this community provides. Whether you're searching for a place to call home or a turnkey investment opportunity, this condo is the opportunity you've been waiting for. This won't last long so schedule your showing today! New water heater (2025) installed by a licensed plumber. Currently occupied month to month.

500 Trent Court, Winston-Salem

$145,900

2 Beds ⋅ 2 Baths ⋅ 1210687 MLS

Turnkey investment opportunity in Cloister Oaks—$1,200/month, currently rented. This 2BR/2BA upper-level condo offers an open, functional layout with laminate flooring, a cozy fireplace, and a kitchen featuring granite countertops and tile backsplash. The private balcony with storage and prime location directly across from the community pool add to the appeal. With HOA covering water and sewer, this is a low-maintenance, income-producing property ready to add to your portfolio from day one.

118 Cloister Oaks Circle, Winston-Salem

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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 .