Cypress Run Real Estate

Welcome to Cypress Run, a hidden gem nestled in the heart of Greenville, South Carolina. This picturesque subdivision offers a perfect blend of suburban tranquility and urban convenience, making it an ideal choice for families, professionals, and retirees alike.

Cypress Run is characterized by its charming tree-lined streets and beautifully landscaped homes, each exuding unique character and style. Residents enjoy spacious lots that provide ample outdoor space for gardening, play, or simply soaking in the serene surroundings. The community is designed with a focus on nature, featuring lush green spaces and scenic walking trails that invite you to explore the great outdoors right from your doorstep.

One of the standout features of Cypress Run is its family-friendly atmosphere. The subdivision is located within the highly-rated Greenville County School District, ensuring that children receive a quality education. Additionally, the community is just a short drive from popular parks, recreational facilities, and shopping centers, offering residents easy access to a variety of amenities.

For those who appreciate a vibrant social scene, downtown Greenville is only minutes away. Here, you'll find an array of dining options, boutique shops, and cultural attractions, all set against the backdrop of the beautiful Reedy River. Whether you're looking for a cozy café or a lively evening out, downtown Greenville has something for everyone.

Cypress Run is more than just a place to live—it's a community where neighbors become friends and memories are made. Come discover the charm of Cypress Run and see why so many choose to call this wonderful subdivision home!

Newest Listings in Cypress Run

$520,000

3 Beds ⋅ 2 Baths

Tucked away at the end of a quiet cul-de-sac in the desirable Cypress Run Community, 21 Windmill Way is the kind of home that feels just as good as it looks! Beautifully maintained and truly MOVE-IN READY, this 3-bedroom, 2-bath home features an EXPANSIVE BONUS ROOM that offers endless possibilities for a home office, gym, or playroom. The inviting open floor plan also includes beautiful wood floors, high ceilings, crown molding, and an abundance of attic storage. The heart of the home is the warm and welcoming living room, highlighted by a handsome BUILT-IN BOOKCASE and a cozy GAS FIREPLACE with custom tiling. The large kitchen offers plenty of cabinetry and generous counter space, making everyday living and entertaining effortless. The primary suite is a retreat of its own, featuring a spacious en-suite bath with a jetted soaking tub, a separate walk-in shower, and plenty of closet space. Just off the primary is an impressive DRESSING ROOM complete with custom built-ins and shelving—an incredible space for keeping everything beautifully organized. One of the home's standout features is the huge HEATED & COOLED FLORIDA ROOM with tile flooring, providing a wonderful year-round living space for relaxing, entertaining, or simply enjoying views of the backyard. And what a backyard it is! Situated on ONE OF THE LARGEST LOTS in the neighborhood, the expansive yard is beautifully landscaped and surrounded by mature trees for added privacy. A large deck creates the perfect setting for cookouts, gatherings, and outdoor entertaining—with plenty of backyard space to create the outdoor oasis you've been dreaming of. All of this is located in a fantastic Greenville location, just minutes from Woodruff Road shopping, dining, everyday conveniences, and easy interstate access. The home is also set up for FIBER OPTIC INTERNET for the convenience of working from home. BEAUTIFUL LANDSCAPING that becomes even more stunning when the flowers are in full bloom! Call and schedule your private showing today!

21 Windmill Way, Greenville

$450,000

4 Beds ⋅ 3 Baths

Full brick 1.5 story in popular Greenville subdivision, Cypress Run! Split floor plan with primary suite on main floor plus jack and jill style additional 2 bedrooms on opposite side of the house. Upstairs is a full bedroom suite plus large bonus ( currently being used as media room and projector remains.) Easy access to just about everything including back routes to the mall and downtown Greenville, Mauldin and Simpsonville! Just a few minutes from Woodruff Road attractions, shopping and dining, theaters. The kitchen has eat in area with built in side buffet. Lots of walk in storage, Irrigation system, and insect prevention system. New roof 2019, new HVAC system 2023, gas fireplace and terrific private backyard with screened porch, nicely landscaped and wood privacy fence. Location is everything and this one is prime.

2 Windmill Way, Greenville

$425,000

3 Beds ⋅ 2 Baths

Buyers can receive a reduced interest rate with an acceptable contract and financed with Katie Myers at PrimeLending for all contracts written through September 30th. Available for qualifying loan types only. This beautifully maintained 3-bedroom, 2-bath brick home offers the ease of one-level living with timeless finishes, including hand scraped hardwood floors throughout, elegant moldings, fresh warm white paint, and spacious living areas designed for everyday comfort. The inviting great room features a trey ceiling, recessed lighting, and a cozy fireplace, while the bright 4 season sunroom is the perfect place to enjoy your morning coffee or unwind with a good book. The well-appointed kitchen offers abundant cabinetry, polished granite countertops, tile backsplash, stainless steel appliances, a casual breakfast area, and a built-in desk that's ideal for staying organized, working from home, or managing everyday tasks. The spacious primary suite includes two closets including a generous walk-in closet, dual vanities with granite countertops, separate shower, water closet, and relaxing jetted tub. Enjoy added peace of mind with a newer architectural roof (2018) and newer HVAC (less than 2 years old), NEW water heater, plus the convenience of a courtyard side-entry two-car garage and generous driveway. The neighborhood itself adds to the lifestyle, as an active community with a walkable setting that invites morning walks, evening strolls, and more time outdoors. People are always out and about when the weather is nice either walking their dogs, riding their bikes, or just hanging out with their friends to get their steps in! It’s an appealing choice if you're looking for a connected neighborhood feel while still enjoying convenient access to shopping, dining, recreation, and everyday essentials. Located just minutes from shopping, dining, medical facilities, downtown Greenville, I-385, and I-85, this move-in ready home offers exceptional accessibility to everything Greenville has to offer. Whether you're looking to simplify, downsize without sacrificing comfort, or simply enjoy a quiet, established neighborhood in an unbeatable location, 4 Windmill Way is ready to welcome you home.

4 Windmill Way, Greenville

$450,000

3 Beds ⋅ 2 Baths

Welcome to 111 Bouchillion Drive in the Cypress Run community, ideally located between Roper Mountain Road and Woodruff Road for quick access to shopping, dining, and daily conveniences while still offering a sense of privacy. Extremely competitive price for this beauty! This well maintained 3 bedroom, 2 bathroom home with a bonus room features highly desirable one level living with a functional and inviting layout. The spacious living room serves as the heart of the home and flows easily into the kitchen, which includes a breakfast area, adjacent dining room, pantry, and brand-new stainless steel appliances that will convey with the sale. A walk-in laundry room is conveniently located just off the garage entry to the home. Tucked toward the rear of the home, a dedicated office/flex space provides a quiet workspace separate from the main living areas. The primary suite offers a private retreat with an updated bathroom featuring a large walk-in shower and modern finishes. Two additional bedrooms are positioned on the other end of the home and share an updated hall bath. Upstairs, the bonus room adds flexible space for a home office, media room, or playroom. Enjoy outdoor living on the spacious screened porch and adjoining patio, perfect for relaxing or entertaining. This home combines comfort, functionality, and a prime location. Schedule your showing today! **Buyers can receive a FREE 1 point rate reduction the first year, with an acceptable contract and financed with Kendall Fox at PrimeLending. Available for qualifying loan types only.**

111 Bouchillion Drive, Greenville

$525,000

3 Beds ⋅ 2 Baths

Welcome to the highly sought-after Cypress Run subdivision, ideally located between Woodruff Road and Roper Mountain Road with quick access to shopping, dining, and GSP Airport. This beautifully maintained, all-brick home features 3 bedrooms and 2 full baths, showcasing a desirable split-bedroom floor plan. Filled with abundant natural light, the open-concept layout offers all bedrooms on the main level, plus a versatile bonus room upstairs—perfect for a home office, media room, or guest space. Thoughtfully updated, the home boasts new architectural roofing, pre-engineered hardwood flooring throughout (with ceramic tile in the bathrooms), granite kitchen countertops and bathroom sinks, and fresh interior paint. Additional upgrades include new light fixtures, a new refrigerator, garbage disposal, and a stackable washer and dryer that convey with the home. The breakfast room features a charming custom window seat nook, while the backyard offers a newly added patio—ideal for entertaining. One standout feature is the oversized screened porch, now converted into a stunning all-seasons room that the seller truly enjoys—perfect for relaxing year-round. The two car garage has extra storage space and a side yard door for easy entry. If you are looking for a low maintenace home, that is move in ready, this is it! This decorator’s personal home combines style, comfort, and convenience—don’t miss your opportunity to make it yours!

231 Bouchillion Drive, Greenville

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The Listings data contained on this website comes from various participants of The Multiple Listing Service of Greenville, SC, Inc. Internet Data Exchange. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The properties displayed may not be all the properties available. All information provided is deemed reliable but is not guaranteed. © 2026 Greater Greenville Association of REALTORS®. All Rights Reserved. Last Updated