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Welcome to Pinebrook! The only homes on half acre plus homesites in Woodruff, SC with prime features and basement options. Introducing the exquisite Kendrick — a thoughtfully designed estate offering more than 3,700 square feet of refined living space on a picturesque over half-acre homesite on a desirable cul de sac location. Blending timeless elegance with modern sophistication, this exceptional residence showcases elevated finishes, expansive entertaining spaces, and seamless indoor-outdoor living. A welcoming covered front porch opens to a grand foyer flanked by a study with french doors, perfect for a home office — and an impressive formal dining room with coffered ceilings connected to a beautifully appointed butler’s pantry featuring abundant prep space and a generous walk-in pantry. At the heart of the home, the stunning open-concept kitchen and great room create an extraordinary gathering space. Designer details include staggered white cabinetry accented by a striking light wood island, Quartz countertops, designer tile backsplash, under-cabinet lighting, farmhouse sink, and a suite of gourmet stainless steel appliances including an electric cooktop, double wall ovens, and range hood. Cathedral ceilings and expansive windows fill the great room with natural light, while the adjoining breakfast area opens to a covered deck overlooking the expansive private backyard. Privately situated on the main level, the luxurious primary suite is a serene retreat featuring tray ceilings, an oversized walk-in closet, dual vanities, and a spa-inspired Roman shower with dual showerheads, built-in seating, and frameless glass enclosure. Additional main-level conveniences include a spacious mudroom, laundry area, and attached three-car garage. Upstairs, an elegant oak staircase leads to a versatile loft perfect for casual living or recreation. Secondary bedrooms are generously sized, including one with an en-suite bath and walk-in closet, while another enjoys access to a beautifully appointed full bath. The walk-out lower level offers exceptional flexibility with a private guest suite, full bath, kitchenette, expansive recreation space, and abundant storage — ideal for entertaining, multigenerational living, or extended guest accommodations. Smart home technology, energy-efficient design, and a dedicated local warranty team ensure long-term comfort and convenience. Premier living at Pinebrook, a captivating new home community centrally located between Spartanburg, SC and Woodruff, SC. Our thoughtfully designed single-family homes cater to diverse lifestyles with both main-level and second-level primary suites, offering flexibility and convenience. Experience the charm of classic architecture with our stunning craftsman-style exteriors featuring James Hardie ColorPlus Siding. Settled in a serene location, these estate homes sit on private half acre plus homesites. Offering select basement homesites and three car garages. Located near Three Pines Country Club, Interstate 85, and Interstate 26, Pinebrook offers the perfect blend of tranquility and accessibility. Pinebrook is a great opportunity in a premier location.

4 Beds ⋅ 4.5 Baths ⋅ 1598488 MLS

Welcome to Pinebrook! The only homes on half acre plus homesites in Woodruff, SC with prime features and basement options. Introducing the exquisite Kendrick — a thoughtfully designed estate offering more than 3,700 square feet of refined living space on a picturesque over half-acre homesite on a desirable cul de sac location. Blending timeless elegance with modern sophistication, this exceptional residence showcases elevated finishes, expansive entertaining spaces, and seamless indoor-outdoor living. A welcoming covered front porch opens to a grand foyer flanked by a study with french doors, perfect for a home office — and an impressive formal dining room with coffered ceilings connected to a beautifully appointed butler’s pantry featuring abundant prep space and a generous walk-in pantry. At the heart of the home, the stunning open-concept kitchen and great room create an extraordinary gathering space. Designer details include staggered white cabinetry accented by a striking light wood island, Quartz countertops, designer tile backsplash, under-cabinet lighting, farmhouse sink, and a suite of gourmet stainless steel appliances including an electric cooktop, double wall ovens, and range hood. Cathedral ceilings and expansive windows fill the great room with natural light, while the adjoining breakfast area opens to a covered deck overlooking the expansive private backyard. Privately situated on the main level, the luxurious primary suite is a serene retreat featuring tray ceilings, an oversized walk-in closet, dual vanities, and a spa-inspired Roman shower with dual showerheads, built-in seating, and frameless glass enclosure. Additional main-level conveniences include a spacious mudroom, laundry area, and attached three-car garage. Upstairs, an elegant oak staircase leads to a versatile loft perfect for casual living or recreation. Secondary bedrooms are generously sized, including one with an en-suite bath and walk-in closet, while another enjoys access to a beautifully appointed full bath. The walk-out lower level offers exceptional flexibility with a private guest suite, full bath, kitchenette, expansive recreation space, and abundant storage — ideal for entertaining, multigenerational living, or extended guest accommodations. Smart home technology, energy-efficient design, and a dedicated local warranty team ensure long-term comfort and convenience. Premier living at Pinebrook, a captivating new home community centrally located between Spartanburg, SC and Woodruff, SC. Our thoughtfully designed single-family homes cater to diverse lifestyles with both main-level and second-level primary suites, offering flexibility and convenience. Experience the charm of classic architecture with our stunning craftsman-style exteriors featuring James Hardie ColorPlus Siding. Settled in a serene location, these estate homes sit on private half acre plus homesites. Offering select basement homesites and three car garages. Located near Three Pines Country Club, Interstate 85, and Interstate 26, Pinebrook offers the perfect blend of tranquility and accessibility. Pinebrook is a great opportunity in a premier location.

630 Winstone Trail, Woodruff

Priced below appraised value!! Combining modern design with the peaceful freedom of a country retreat, this property offers an exceptional opportunity to own a private 9.92-acre haven just three minutes from downtown Woodruff. Tucked away at the end of a winding shared entrance, this property gives you the security and peace of mind of having a neighbor nearby, while unlocking a massive, completely private park-like sanctuary right out your back door.Step inside to an airy open-concept layout defined by wide-plank flooring and a fireplace anchoring the great room. The living area flows effortlessly into a chef's kitchen featuring crisp white cabinetry, granite countertops, and upgraded stainless steel appliances, including a gas range. Throughout the main level, oversized windows flood the interior with natural light and offer breathtaking, tranquil views of the surrounding hardwoods—creating a seamless "living in the trees" experience.The primary suite serves as a true sanctuary, featuring a spa-inspired ensuite with a deep soaking tub, walk-in shower, dual vanities, and a large walk-in closet. Upstairs, a versatile bonus area provides flexible space for a home gym, media room, or office.Outdoor living is elevated by a massive screened-in porch, providing the perfect vantage point to take in the quiet beauty of your nearly ten-acre backyard. Hiking trails have already been cut meandering throughout the nine acres, and providing adventure and serenity right outside your back door. As an added bonus, the property includes an RV parking pad equipped with dedicated electric and sewer hookups.This is an incredible value for acreage so close to town—priced below recent appraisal to support an immediate sale. Call your favorite agent to schedule your tour of the home and the land today!

3 Beds ⋅ 2 Baths ⋅ 1595824 MLS

Priced below appraised value!! Combining modern design with the peaceful freedom of a country retreat, this property offers an exceptional opportunity to own a private 9.92-acre haven just three minutes from downtown Woodruff. Tucked away at the end of a winding shared entrance, this property gives you the security and peace of mind of having a neighbor nearby, while unlocking a massive, completely private park-like sanctuary right out your back door.Step inside to an airy open-concept layout defined by wide-plank flooring and a fireplace anchoring the great room. The living area flows effortlessly into a chef's kitchen featuring crisp white cabinetry, granite countertops, and upgraded stainless steel appliances, including a gas range. Throughout the main level, oversized windows flood the interior with natural light and offer breathtaking, tranquil views of the surrounding hardwoods—creating a seamless "living in the trees" experience.The primary suite serves as a true sanctuary, featuring a spa-inspired ensuite with a deep soaking tub, walk-in shower, dual vanities, and a large walk-in closet. Upstairs, a versatile bonus area provides flexible space for a home gym, media room, or office.Outdoor living is elevated by a massive screened-in porch, providing the perfect vantage point to take in the quiet beauty of your nearly ten-acre backyard. Hiking trails have already been cut meandering throughout the nine acres, and providing adventure and serenity right outside your back door. As an added bonus, the property includes an RV parking pad equipped with dedicated electric and sewer hookups.This is an incredible value for acreage so close to town—priced below recent appraisal to support an immediate sale. Call your favorite agent to schedule your tour of the home and the land today!

1014 Edwards Road, Woodruff

RARE opportunity to own a private retreat-style property just minutes from Five Forks, Willow Creek Golf Course, BMW, and I-85. Nestled on approximately 12 acres, this unique property features a beautiful PRIVATE POND, flowing creek, screened porch, detached solar panels, chicken coop, and multiple outbuildings designed for flexibility and function. The custom log cabin offers rustic charm paired with practical accessibility features, including a custom ramp and wide doorways. A detached oversized two-car garage with workshop, flex building/studio, and additional storage shed provide endless possibilities for hobbies, recreation, workspace, or equipment storage. Whether you’re searching for a full-time residence, private getaway, or multi-use property with room to spread out, this one-of-a-kind setting delivers the privacy, natural beauty, and versatility that are increasingly hard to find. Enjoy peaceful water views, open space, and a lifestyle tailored for those who appreciate nature, recreation, and self-sufficiency, all in a convenient location close to shopping, dining, and major employers. Buyer to verify detached buildings and any intended alternate uses.

2 Beds ⋅ 2 Baths ⋅ 337519 MLS

RARE opportunity to own a private retreat-style property just minutes from Five Forks, Willow Creek Golf Course, BMW, and I-85. Nestled on approximately 12 acres, this unique property features a beautiful PRIVATE POND, flowing creek, screened porch, detached solar panels, chicken coop, and multiple outbuildings designed for flexibility and function. The custom log cabin offers rustic charm paired with practical accessibility features, including a custom ramp and wide doorways. A detached oversized two-car garage with workshop, flex building/studio, and additional storage shed provide endless possibilities for hobbies, recreation, workspace, or equipment storage. Whether you’re searching for a full-time residence, private getaway, or multi-use property with room to spread out, this one-of-a-kind setting delivers the privacy, natural beauty, and versatility that are increasingly hard to find. Enjoy peaceful water views, open space, and a lifestyle tailored for those who appreciate nature, recreation, and self-sufficiency, all in a convenient location close to shopping, dining, and major employers. Buyer to verify detached buildings and any intended alternate uses.

425 Cooper Bridge Rd, Woodruff

RARE opportunity to own a private retreat-style property just minutes from Five Forks, Willow Creek Golf Course, BMW, and I-85. Nestled on approximately 12 acres, this unique property features a beautiful PRIVATE POND, flowing creek, screened porch, detached solar panels, chicken coop, and multiple outbuildings designed for flexibility and function. The custom log cabin offers rustic charm paired with practical accessibility features, including a custom ramp and wide doorways. A detached oversized two-car garage with workshop, flex building/studio, and additional storage shed provide endless possibilities for hobbies, recreation, workspace, or equipment storage. Whether you’re searching for a full-time residence, private getaway, or multi-use property with room to spread out, this one-of-a-kind setting delivers the privacy, natural beauty, and versatility that are increasingly hard to find. Enjoy peaceful water views, open space, and a lifestyle tailored for those who appreciate nature, recreation, and self-sufficiency, all in a convenient location close to shopping, dining, and major employers. Buyer to verify detached buildings and any intended alternate uses.

2 Beds ⋅ 2 Baths ⋅ 1592767 MLS

RARE opportunity to own a private retreat-style property just minutes from Five Forks, Willow Creek Golf Course, BMW, and I-85. Nestled on approximately 12 acres, this unique property features a beautiful PRIVATE POND, flowing creek, screened porch, detached solar panels, chicken coop, and multiple outbuildings designed for flexibility and function. The custom log cabin offers rustic charm paired with practical accessibility features, including a custom ramp and wide doorways. A detached oversized two-car garage with workshop, flex building/studio, and additional storage shed provide endless possibilities for hobbies, recreation, workspace, or equipment storage. Whether you’re searching for a full-time residence, private getaway, or multi-use property with room to spread out, this one-of-a-kind setting delivers the privacy, natural beauty, and versatility that are increasingly hard to find. Enjoy peaceful water views, open space, and a lifestyle tailored for those who appreciate nature, recreation, and self-sufficiency, all in a convenient location close to shopping, dining, and major employers. Buyer to verify detached buildings and any intended alternate uses.

425 Cooper Bridge Road, Woodruff

Welcome to a stunning custom-built home with NO HOA, thoughtfully designed for space, comfort, beauty, warmth and easy of living in peaceful neighborhood at Three Pines Country Club in Woodruff. A welcoming covered front porch with elegant glass double doors sets the tone as you enter. This home features a well-planned open floor plan, soaring ceilings, wide-plank hardwood floors, electric fire place in the living room. Kitchen with a beautiful waterfall island that is truly the heart of this home. The primary suite features a large bedroom with cathedral ceiling, heated floor in the bathroom, double vanity and freestanding soaking tub and two separate custom -built walk-in closets. Upstairs, a spacious flex room + additional space with its own full bathroom. The outdoor living is just as impressive as the interior. A massive half covered rear deck features a tongue and groove pine ceiling, a fully equipped outdoor kitchen with a built-in grill and cabinetry for your relaxation after a long day. Golf lovers will appreciate that Three Pines has membership opportunities that can be purchased in addition. Every detail of this home was designed with intention. Every finish was chosen with care. This is not just a house- this is the one you've been waiting for. Don't miss this rare opportunity - schedule your showing today!

5 Beds ⋅ 5 Baths ⋅ 337283 MLS

Welcome to a stunning custom-built home with NO HOA, thoughtfully designed for space, comfort, beauty, warmth and easy of living in peaceful neighborhood at Three Pines Country Club in Woodruff. A welcoming covered front porch with elegant glass double doors sets the tone as you enter. This home features a well-planned open floor plan, soaring ceilings, wide-plank hardwood floors, electric fire place in the living room. Kitchen with a beautiful waterfall island that is truly the heart of this home. The primary suite features a large bedroom with cathedral ceiling, heated floor in the bathroom, double vanity and freestanding soaking tub and two separate custom -built walk-in closets. Upstairs, a spacious flex room + additional space with its own full bathroom. The outdoor living is just as impressive as the interior. A massive half covered rear deck features a tongue and groove pine ceiling, a fully equipped outdoor kitchen with a built-in grill and cabinetry for your relaxation after a long day. Golf lovers will appreciate that Three Pines has membership opportunities that can be purchased in addition. Every detail of this home was designed with intention. Every finish was chosen with care. This is not just a house- this is the one you've been waiting for. Don't miss this rare opportunity - schedule your showing today!

112 Oakwood Dr, Woodruff

Custom built home on 2+ acres in a private community with no HOA! Home is ready for you to pick colors and finishes! Home features LVP & tile flooring, electric fireplace, sunroom, covered wrap around front porch, tray ceilings, coffered ceilings, and custom carpentry throughout! Current lot is 2 acres with plenty of room for a pool or additional building. Small community encompassed by beautiful tree line. Equestrian enthusiast or just looking for more land? See additional photos. There is an additional 6 +/- acres available with custom horse stables and large barn with workshop, full living quarters, loft space & full kitchen built in. Minutes to I-26 & downtown Woodruff, 15 minutes to Simpsonville or Spartanburg, GSP airport is 20 minutes, and just 30 minutes to all that downtown Greenville has to offer.

3 Beds ⋅ 2.5 Baths ⋅ 1586373 MLS

Custom built home on 2+ acres in a private community with no HOA! Home is ready for you to pick colors and finishes! Home features LVP & tile flooring, electric fireplace, sunroom, covered wrap around front porch, tray ceilings, coffered ceilings, and custom carpentry throughout! Current lot is 2 acres with plenty of room for a pool or additional building. Small community encompassed by beautiful tree line. Equestrian enthusiast or just looking for more land? See additional photos. There is an additional 6 +/- acres available with custom horse stables and large barn with workshop, full living quarters, loft space & full kitchen built in. Minutes to I-26 & downtown Woodruff, 15 minutes to Simpsonville or Spartanburg, GSP airport is 20 minutes, and just 30 minutes to all that downtown Greenville has to offer.

406 Casey Road, Woodruff

The Yates II is a two-story home with five bedrooms and four-and-one-half baths. Upon entry, you are immediately greeted by an office with French doors. Next, you will find the formal dining room that leads to an open-concept great room and kitchen. A butler’s pantry connects the dining room to the kitchen. The spacious great room is open to the kitchen. The garage entry offers a functional organizational space and access to an optional first floor premier suite with a full bath. A powder room completes the first floor. Upstairs, there are three secondary bedrooms, each featuring walk-in closets. A media room and a large laundry room with sink and cabinets are also located on the second floor. The luxurious primary suite features a boxed ceiling, sitting room and dual closets with a dressing area. This home also includes a 2-car attached garage and a 2-car detached garage with attic space. Nestled in the desirable town of Reidville, this thoughtfully designed community offers 51 spacious homesites of half an acre or more, providing ample room for outdoor living, privacy, and relaxation. With home designs ranging from 1,600 to 4,000 square feet, Ben’s Crossing caters to a variety of lifestyles, from growing families to those looking for a peaceful retreat with extra space. Future amenities—including a cabana, playground, and pickleball courts—will enhance the community’s charm, fostering an active and welcoming environment. Ideally situated between Downtown Spartanburg and Downtown Greenville, residents enjoy easy access to both cities' dining, shopping, and entertainment, as well as major employment centers.

5 Beds ⋅ 4.5 Baths ⋅ 1581570 MLS

The Yates II is a two-story home with five bedrooms and four-and-one-half baths. Upon entry, you are immediately greeted by an office with French doors. Next, you will find the formal dining room that leads to an open-concept great room and kitchen. A butler’s pantry connects the dining room to the kitchen. The spacious great room is open to the kitchen. The garage entry offers a functional organizational space and access to an optional first floor premier suite with a full bath. A powder room completes the first floor. Upstairs, there are three secondary bedrooms, each featuring walk-in closets. A media room and a large laundry room with sink and cabinets are also located on the second floor. The luxurious primary suite features a boxed ceiling, sitting room and dual closets with a dressing area. This home also includes a 2-car attached garage and a 2-car detached garage with attic space. Nestled in the desirable town of Reidville, this thoughtfully designed community offers 51 spacious homesites of half an acre or more, providing ample room for outdoor living, privacy, and relaxation. With home designs ranging from 1,600 to 4,000 square feet, Ben’s Crossing caters to a variety of lifestyles, from growing families to those looking for a peaceful retreat with extra space. Future amenities—including a cabana, playground, and pickleball courts—will enhance the community’s charm, fostering an active and welcoming environment. Ideally situated between Downtown Spartanburg and Downtown Greenville, residents enjoy easy access to both cities' dining, shopping, and entertainment, as well as major employment centers.

206 Castlebar Street Unit Lot 51, Woodruff

25.75 ACRES- Beautiful land with fenced pastures, hardwoods, creek and barn. Build your dream home and have your own little slice of heaven. Pictures can't capture the splendor and beauty of this land. This property offers many possibilities. It is already set up for a farm, but could also be subdivided after purchase to allow for several homesites. Barn is 30 x 60. Mobile home is occupied and does not convey. It will be removed prior to closing. Please do not approach mobile home or disturb owners/occupants.

25.75 ACRES- Beautiful land with fenced pastures, hardwoods, creek and barn. Build your dream home and have your own little slice of heaven. Pictures can't capture the splendor and beauty of this land. This property offers many possibilities. It is already set up for a farm, but could also be subdivided after purchase to allow for several homesites. Barn is 30 x 60. Mobile home is occupied and does not convey. It will be removed prior to closing. Please do not approach mobile home or disturb owners/occupants.

240 Simmons Road, Woodruff

25.75 ACRES- Beautiful land with fenced pastures, hardwoods, creek and barn. Build your dream home and have your own little slice of heaven. Pictures can't capture the splendor and beauty of this land. This property offers many possibilities. It is already set up for a farm, but could also be subdivided after purchase to allow for several homesites. Barn is 30 x 60. Mobile home is occupied and does not convey. It will be removed prior to closing. Please do not approach mobile home or disturb owners/occupants. Appointment is required to visit and walk the land. It is easily walkable as much of it is level or gently sloping.

25.75 ACRES- Beautiful land with fenced pastures, hardwoods, creek and barn. Build your dream home and have your own little slice of heaven. Pictures can't capture the splendor and beauty of this land. This property offers many possibilities. It is already set up for a farm, but could also be subdivided after purchase to allow for several homesites. Barn is 30 x 60. Mobile home is occupied and does not convey. It will be removed prior to closing. Please do not approach mobile home or disturb owners/occupants. Appointment is required to visit and walk the land. It is easily walkable as much of it is level or gently sloping.

Woodruff

Very private 54.40 partially wooded acreage with abundant wildlife!! Great for residential, or recreational! Located just over a mile from I-26. No HOA. Hunting club opportunity! Several beautiful homesites! Tons of privacy but still convenient location to shopping and restaurants. Downtown Woodruff is only 4 miles away. Call me today for your private tour! Dominion Pipeline runs under the very front of property.

Very private 54.40 partially wooded acreage with abundant wildlife!! Great for residential, or recreational! Located just over a mile from I-26. No HOA. Hunting club opportunity! Several beautiful homesites! Tons of privacy but still convenient location to shopping and restaurants. Downtown Woodruff is only 4 miles away. Call me today for your private tour! Dominion Pipeline runs under the very front of property.

Woodruff

Very private 54.40 partially wooded acreage abundant with wildlife!! This property would be great for residential, or recreational. Located just over a mile from I-26. Awesome hunting club opportunity! Beautiful homesites! Several pretty home site areas that has tons of privacy but still convenient location to shopping and restaurants. Downtown Woodruff is only 4 miles away. Call me today for your private tour! Dominion Pipeline runs through the property.

Very private 54.40 partially wooded acreage abundant with wildlife!! This property would be great for residential, or recreational. Located just over a mile from I-26. Awesome hunting club opportunity! Beautiful homesites! Several pretty home site areas that has tons of privacy but still convenient location to shopping and restaurants. Downtown Woodruff is only 4 miles away. Call me today for your private tour! Dominion Pipeline runs through the property.

Roddy Road, Woodruff

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