Cloister Oaks Condos for Sale

Welcome to Cloister Oaks—a hidden gem nestled in the heart of Winston-Salem, North Carolina, where modern living meets serene surroundings. This charming subdivision, located in Forsyth County, is perfect for those seeking a vibrant community with easy access to all the amenities you desire.

Cloister Oaks boasts a selection of beautifully designed condos for sale, each offering a unique blend of comfort and style. With spacious layouts, contemporary finishes, and an abundance of natural light, these residences are perfect for both first-time buyers and those looking to downsize. Imagine sipping your morning coffee on a private balcony, surrounded by lush greenery and the tranquility that Cloister Oaks provides.

Residents here enjoy a wealth of nearby conveniences, including shopping centers, restaurants, and recreational parks. The community is well-connected to major highways, making it easy to explore all that Winston-Salem has to offer. Whether you’re in the mood for a cultural outing at a local art gallery or a leisurely stroll through one of the picturesque parks, you’ll find it all just minutes away.

Cloister Oaks is not just a place to live; it’s a lifestyle. With a friendly atmosphere and a strong sense of community, you’ll feel at home from the moment you arrive. Explore the condos for sale in Cloister Oaks today and discover the perfect blend of comfort, convenience, and charm in Winston-Salem, NC. Your dream home awaits!

Newest Cloister Oaks Condos for Sale

$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 .