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101 Henderson Street, Woodstock
$1,350,000
5 Beds ⋅ 6 Baths ⋅ 10708626 MLS
Just steps from the vibrant heart of Downtown Woodstock, this fully custom-built home offers a rare blend of luxury, privacy, and true walkability in one of the area's most energetic and beloved communities. Set on more than half an acre, the property delivers the space and comfort of a private estate while placing you just moments from Woodstock's acclaimed restaurants, boutique shops, local parks, live music, and year-round festivals. Inside, the home reflects thoughtful design and craftsmanship throughout, with open living spaces. The chef's kitchen serves as the heart of the home, featuring an oversized island, premium appliances, and seamless flow into the main gathering spaces. Natural light fills the interiors, highlighting custom details and beautifully designed living areas that connect effortlessly to the outdoor spaces. The home offers five spacious bedrooms and four full bathrooms, along with flexible spaces designed for modern living - including a dedicated office for working from home and a private home gym. Tucked above it all, a rooftop deck provides an elevated retreat and a unique vantage point to enjoy sunset views, morning coffee, or evening gatherings under the stars. Step outside and the lifestyle truly comes to life. The courtyard-style backyard feels like your own private resort, anchored by a saltwater pool and hot tub that create the perfect setting for warm summer afternoons and relaxed evenings. Just beyond, a fully appointed pool house adds incredible flexibility to the property, complete with an additional bedroom, one and a half bathrooms, and a game room - ideal for hosting guests, extended stays, or creating a separate space for entertaining. Homes offering this level of custom craftsmanship, outdoor living, and walkability to Downtown Woodstock are incredibly rare. Here, you'll experience the best of both worlds - a one-of-a-kind custom residence with room to spread out, paired with the dynamic, walkable lifestyle that makes Downtown Woodstock one of the most exciting places to live in Cherokee County.

101 Henderson Street, Woodstock

101 Henderson Street, Woodstock
$1,350,000
5 Beds ⋅ 6 Baths ⋅ 7732502 MLS
Just steps from the vibrant heart of Downtown Woodstock, this fully custom-built home offers a rare blend of luxury, privacy, and true walkability in one of the area’s most energetic and beloved communities. Set on more than half an acre, the property delivers the space and comfort of a private estate while placing you just moments from Woodstock’s acclaimed restaurants, boutique shops, local parks, live music, and year-round festivals. Inside, the home reflects thoughtful design and craftsmanship throughout, with open living spaces. The chef’s kitchen serves as the heart of the home, featuring an oversized island, premium appliances, and seamless flow into the main gathering spaces. Natural light fills the interiors, highlighting custom details and beautifully designed living areas that connect effortlessly to the outdoor spaces. The home offers five spacious bedrooms and four full bathrooms, along with flexible spaces designed for modern living — including a dedicated office for working from home and a private home gym. Tucked above it all, a rooftop deck provides an elevated retreat and a unique vantage point to enjoy sunset views, morning coffee, or evening gatherings under the stars. Step outside and the lifestyle truly comes to life. The courtyard-style backyard feels like your own private resort, anchored by a saltwater pool and hot tub that create the perfect setting for warm summer afternoons and relaxed evenings. Just beyond, a fully appointed pool house adds incredible flexibility to the property, complete with an additional bedroom, one and a half bathrooms, and a game room — ideal for hosting guests, extended stays, or creating a separate space for entertaining. Homes offering this level of custom craftsmanship, outdoor living, and walkability to Downtown Woodstock are incredibly rare. Here, you’ll experience the best of both worlds — a one-of-a-kind custom residence with room to spread out, paired with the dynamic, walkable lifestyle that makes Downtown Woodstock one of the most exciting places to live in Cherokee County.

101 Henderson Street, Woodstock

169 Hubbard Road, Woodstock
$972,000
3 Beds ⋅ 3 Baths ⋅ 10672122 MLS
Custom designed French Colonial Hedgewood home! Gated, private yard and driveway on a large end lot with additional parking and ample overhead storage. This stunning master on main has three porches, amazing for our outdoor lovers. Beautiful bricked floor foyer catches your eyes immediately along with the 4' wide staircase. The entire main level has 5" pine plank flooring-tung oil finish that you don't see often. Enjoy some peace and quiet in the living/library room with access to one of your patios. Open concept kitchen with new appliances that remain with the home, including a new gas range and cooktop! Custom size fireplace with an antique mantle in the family room. Screened flagstone porch off family room & private brick patio, perfect for coffee in the morning! Lower level includes two additional bedrooms, full bathroom with stunning tile work, a secondary kitchen and living space, perfect for the in-laws AND a breathtaking wine cellar fully stocked that remains with the home! Additional items: Security system installed and renewed by subscription Gas water heater added a recirculating pump Generac - whole house generator Gutter guards added New fence at the entrance New stone landscaping on the west side of the house Bidet added in 2025 All appliances will remain with home (most appliances are new)

169 Hubbard Road, Woodstock

169 Hubbard Road, Woodstock
$972,000
3 Beds ⋅ 3 Baths ⋅ 7703129 MLS
Custom designed French Colonial Hedgewood home! Gated, private yard and driveway on a large end lot with additional parking and ample overhead storage. This stunning master on main has three porches, amazing for our outdoor lovers. Beautiful bricked floor foyer catches your eyes immediately along with the 4' wide staircase. The entire main level has 5" pine plank flooring-tung oil finish that you don’t see often. Enjoy some peace and quiet in the living/library room with access to one of your patios. Open concept kitchen with new appliances that remain with the home, including a new gas range and cooktop! Custom size fireplace with an antique mantle in the family room. Screened flagstone porch off family room & private brick patio, perfect for coffee in the morning! Lower level includes two additional bedrooms, full bathroom with stunning tile work, a secondary kitchen and living space, perfect for the in-laws AND a breathtaking wine cellar fully stocked that remains with the home! Additional items: Security system installed and renewed by subscription Gas water heater added a recirculating pump Generac - whole house generator Gutter guards added New fence at the entrance New stone landscaping on the west side of the house Bidet added in 2025 All appliances will remain with home (most appliances are new)

169 Hubbard Road, Woodstock

109 Linton Street, Woodstock
$875,000
4 Beds ⋅ 3 Baths ⋅ 10596394 MLS
Rare Downtown Woodstock GEM! If you've ever strolled through the heart of Woodstock, you know this home! Perfectly situated on a corner lot just steps from Adair Park and vibrant Downtown Woodstock, this 1954 charmer has been fully renovated while keeping its character intact. Sitting on nearly half an acre with no HOA, this spacious 3,300 sq. ft. home offers 4 bedrooms and 3 bathrooms, including a master suite on the main level. The bright, open-concept main floor boasts modern finishes and thoughtful details that make it both stylish and welcoming. The finished basement is a game-changer - featuring a bedroom, full bath, kitchenette, bonus space, and generous storage, making it perfect for guests, in-laws, or even an income opportunity. Enjoy the spacious lot with a large deck and plenty of parking, all within walking distance to Woodstock's boutique shops, local dining, parks, and year-round events. Don't miss this rare opportunity to own a piece of Downtown Woodstock living! Showings begin on 9/12/2025.

109 Linton Street, Woodstock

109 Linton Street, Woodstock
$875,000
4 Beds ⋅ 3 Baths ⋅ 7640049 MLS
Rare Downtown Woodstock GEM! If you’ve ever strolled through the heart of Woodstock, you know this home! Perfectly situated on a corner lot just steps from Adair Park and vibrant Downtown Woodstock, this 1954 charmer has been fully renovated while keeping its character intact. Sitting on nearly half an acre with no HOA, this spacious 3,300 sq. ft. home offers 4 bedrooms and 3 bathrooms, including a master suite on the main level. The bright, open-concept main floor boasts modern finishes and thoughtful details that make it both stylish and welcoming. The finished basement is a game-changer — featuring a bedroom, full bath, kitchenette, bonus space, and generous storage, making it perfect for guests, in-laws, or even an income opportunity. Enjoy the spacious lot with a large deck and plenty of parking, all within walking distance to Woodstock’s boutique shops, local dining, parks, and year-round events. Don’t miss this rare opportunity to own a piece of Downtown Woodstock living!

109 Linton Street, Woodstock

125 Hubbard Road, Woodstock
$840,000
4 Beds ⋅ 5 Baths ⋅ 10730220 MLS
This Stunning Townhome is truly one of a kind. Beautiful Gated Courtyard with Spacious Covered Porch Welcomes you Home. Truly the Perfect place to relax. Fantastic Chefs Kitchen has custom cabinets and a 6 Burner Stove, Breakfast Bar & Gorgeous Shiplap. The Grand Dining Room has floor to ceiling windows that showcase the Romantic Courtyard. Upstairs is your large Master Suite with a Spa Like Bathroom, Laundry room, & Two Additional Bedrooms each with a Full Bath. The Terrace level has another Bedroom, Full Bath, a Second Laundry Room, Additional space for Storage & 2 Car Garage. Every room in this home is Gorgeous. Amenities include, Pool & Park. Walking distance to Downtown Woodstock restaurants, amphitheater, parks and shops. FRESHLY PAINTED!!!!

125 Hubbard Road, Woodstock

360 Chambers Street, Woodstock
$505,000
2 Beds ⋅ 2 Baths ⋅ 10804362 MLS
Welcome to comfort and effortless living in the heart of Woodstock's downtown premier gated community on Chamber's Street! Discover the perfect blend of luxury living and suburban charm in this 2-bedroom, 2-bath home w/all one-level, easy living and gorgeous views! Freshly painted patio! As one of the larger floor plans, this meticulously maintained, inviting open plan offers a spectacular kitchen that seamlessly connects the living area, dining room, and large covered outdoor balcony, all bathed in natural light. Freshly painted and with an open, airy layout, this split plan unit features soaring 1O1/2-foot ceilings and 8-foot doors. There are wood floors in most rooms and closets while tile flooring adorns both bathrooms. Crown molding throughout the home provides a fine finishing touch! Unlike many units this one has a completely upgraded & renovated high-end kitchen! Cabinets with glass fronts at the top adorned with lighting. Culinary enthusiasts will appreciate the LG stainless steel appliances,ample cabinetry, &versatile island for casual dining or entertaining.The quartz countertops & backsplash are complimented w/ undermount cabinet lighting. Soft-close pullouts and drawers make for easy handling and 42" uppers provide for addtl storage. Extended island is more than 5 feet by nearly 7 feet w/pullouts providing storage. Step outside to the quiet extended balcony w/eastern exposure & panoramic views that maximize the stunning landscape. The freshly painted balcony is further enhanced w/outdoor fans and lighting, perfect for year-round relaxation or entertainment. This third-floor home doesn't overlook Main Street or downtown, but rather it faces eastward over treetops, providing lovely sunrises along w/peace & quiet located in a downtown community. The balcony is large enough for seating more than eight people comfortably. Windows are 76 inches, along w/an 8-foot balcony door, all & have automatic/programmable shades. This split plan offers 2 bedrms & 2 full baths. Private primary suite has a large, outfitted walk-in closet, dual vanities, a separate water closet, a stand-alone shower, and a large bathtub. The laundry closet in bathroom allows for a stackable full-size washer & dryer. The spacious second bedroom has a full bath with linen storage as well and is ideal for guests or turn this room into a den or home office. It also has an outfitted walk-in closet. Upgrades in 2024: New kitchen with LG stainless steel appliances; new hot water heater; new ceiling fans in living area and both bedrooms; walk-in closets outfitted and adaptable/changeable; utility closet holds the HVAC, hot water heater and offers additional storage space; new internal ceiling exhaust fan for the dryer duct; HVAC duct work, new HVAC coil (2026) w/warranty, dryer vent, and other venting cleaned; all walls, doors, crown molding, and baseboards painted; outdoor ceiling fans and light. This unit also includes two covered beneath the building side-by-side parking spaces near the unit's lobby door. The HOA takes care of a secured building, underneath building convenient parking garage, outdoor spaces, entrance and exit gates, a large community pool with outdoor BBQ grills and neighborhood parks, building lobbies, common spaces, onsite dog park, along with trash, and recycling services. There are even spaces in the parking garage for bicycles & guest parking passes. Step outside to varying restaurants, numerous boutique shops and cafes, breweries, neighborhood and city parks and trails; walk to the city amphitheater for one of the free concerts, stroll over to the Woodstock Art House for a show, or meander through downtown to the Reaves House Visual Arts Center. Woodstock is an inviting and a social city, and this residence combines privacy with those conveniences. Do not miss the opportunity to own this beautiful condo home. Schedule your private tour today and experience elevated living in one of Woodstock's premier communities.

360 Chambers Street, Woodstock

360 Chambers Street Unit 309, Woodstock
$505,000
2 Beds ⋅ 2 Baths ⋅ 7802589 MLS ⋅ Downtown Woodstock BLDG.
Welcome to comfort and effortless living in the heart of Woodstock's downtown premier gated community on Chamber's Street! Discover the perfect blend of luxury living and suburban charm in this 2-bedroom, 2-bath home w/all one-level, easy living and gorgeous views! Freshly painted patio! As one of the larger floor plans, this meticulously maintained, inviting open plan offers a spectacular kitchen that seamlessly connects the living area, dining room, and large covered outdoor balcony, all bathed in natural light. Freshly painted and with an open, airy layout, this split plan unit features soaring 1O½-foot ceilings and 8-foot doors. There are wood floors in most rooms and closets while tile flooring adorns both bathrooms. Crown molding throughout the home provides a fine finishing touch! Unlike many units this one has a completely upgraded & renovated high-end kitchen! Cabinets with glass fronts at the top adorned with lighting. Culinary enthusiasts will appreciate the LG stainless steel appliances,ample cabinetry, &versatile island for casual dining or entertaining.The quartz countertops & backsplash are complimented w/ undermount cabinet lighting. Soft-close pullouts and drawers make for easy handling and 42" uppers provide for addtl storage. Extended island is more than 5 feet by nearly 7 feet w/pullouts providing storage. Step outside to the quiet extended balcony w/eastern exposure & panoramic views that maximize the stunning landscape. The freshly painted balcony is further enhanced w/outdoor fans and lighting, perfect for year-round relaxation or entertainment. This third-floor home doesn't overlook Main Street or downtown, but rather it faces eastward over treetops, providing lovely sunrises along w/peace & quiet located in a downtown community. The balcony is large enough for seating more than eight people comfortably. Windows are 76 inches, along w/an 8-foot balcony door, all & have automatic/programmable shades. This split plan offers 2 bedrms & 2 full baths. Private primary suite has a large, outfitted walk-in closet, dual vanities, a separate water closet, a stand-alone shower, and a large bathtub. The laundry closet in bathroom allows for a stackable full-size washer & dryer. The spacious second bedroom has a full bath with linen storage as well and is ideal for guests or turn this room into a den or home office. It also has an outfitted walk-in closet. Upgrades in 2024: New kitchen with LG stainless steel appliances; new hot water heater; new ceiling fans in living area and both bedrooms; walk-in closets outfitted and adaptable/changeable; utility closet holds the HVAC, hot water heater and offers additional storage space; new internal ceiling exhaust fan for the dryer duct; HVAC duct work, new HVAC coil (2026) w/warranty, dryer vent, and other venting cleaned; all walls, doors, crown molding, and baseboards painted; outdoor ceiling fans and light. This unit also includes two covered beneath the building side-by-side parking spaces near the unit's lobby door. The HOA takes care of a secured building, underneath building convenient parking garage, outdoor spaces, entrance and exit gates, a large community pool with outdoor BBQ grills and neighborhood parks, building lobbies, common spaces, onsite dog park, along with trash, and recycling services. There are even spaces in the parking garage for bicycles & guest parking passes. Step outside to varying restaurants, numerous boutique shops and cafes, breweries, neighborhood and city parks and trails; walk to the city amphitheater for one of the free concerts, stroll over to the Woodstock Art House for a show, or meander through downtown to the Reaves House Visual Arts Center. Woodstock is an inviting and a social city, and this residence combines privacy with those conveniences. Do not miss the opportunity to own this beautiful condo home. Schedule your private tour today and experience elevated living in one of Woodstock's premier communities.

360 Chambers Street Unit 309, Woodstock

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