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Some people move to Woodstock. Other people move to the part of Woodstock everyone else drives to. 165 Hubbard Road is the second one. Not five minutes from downtown. Not conveniently located near downtown. Actually IN downtown Woodstock. The restaurants. The boutiques. The coffee shops. The live music. The festivals. The nights when dinner turns into drinks and nobody has to volunteer to move the car. This is the Woodstock lifestyle people keep talking about, and from here, you can actually live it. And the house? Well, it understood the assignment. Three stories of beautiful architecture, brick arches, a ridiculously cute fenced-in front yard, and porches. So many porches. Big, covered, double-stacked front porches with ceiling fans and enough room to make you seriously reconsider how much time you spend indoors. Morning coffee? Porch. Afternoon reading? Different porch. Evening cocktail? You have options. Inside, the home is just as good-looking as the outside. Hardwood floors, beautiful trim, plantation shutters, and an open main living area that feels polished without being too precious to actually live in. The kitchen offers a generous island, plenty of cabinetry, and easy flow into the living spaces. There is even a built-in beverage station, because apparently this house knows how to host. The primary suite keeps things comfortable with built-in cabinetry, generous space, and a bathroom featuring dual vanities and a freestanding soaking tub. Four bedrooms and three and a half bathrooms offer flexibility across the home's three levels, while the two-car garage takes care of another practical detail. And then there is the elevator. Because three stories sound wonderful until you are carrying groceries, luggage, or a basket of laundry upstairs. The elevator handles the vertical commute so you can enjoy all that space without treating your own house like a stair-climbing competition. But here's the thing about 165 Hubbard Road. You can find beautiful kitchens. You can find big porches. You can find three-story homes and gorgeous bathrooms. What you cannot easily find is all of that in the middle of downtown Woodstock. Walk to dinner. Wander through the shops. Catch a concert. Meet friends for coffee. Come home and sit on your porch while the neighborhood settles into the evening. Three stories. Porches for days. An elevator. A fenced front yard. And a downtown Woodstock address that makes the whole thing even better. Some homes give you a great place to live. This one gives you a great place to live and a great place to be.

4 Beds ⋅ 4 Baths ⋅ 7859125 MLS

Some people move to Woodstock. Other people move to the part of Woodstock everyone else drives to. 165 Hubbard Road is the second one. Not five minutes from downtown. Not conveniently located near downtown. Actually IN downtown Woodstock. The restaurants. The boutiques. The coffee shops. The live music. The festivals. The nights when dinner turns into drinks and nobody has to volunteer to move the car. This is the Woodstock lifestyle people keep talking about, and from here, you can actually live it. And the house? Well, it understood the assignment. Three stories of beautiful architecture, brick arches, a ridiculously cute fenced-in front yard, and porches. So many porches. Big, covered, double-stacked front porches with ceiling fans and enough room to make you seriously reconsider how much time you spend indoors. Morning coffee? Porch. Afternoon reading? Different porch. Evening cocktail? You have options. Inside, the home is just as good-looking as the outside. Hardwood floors, beautiful trim, plantation shutters, and an open main living area that feels polished without being too precious to actually live in. The kitchen offers a generous island, plenty of cabinetry, and easy flow into the living spaces. There is even a built-in beverage station, because apparently this house knows how to host. The primary suite keeps things comfortable with built-in cabinetry, generous space, and a bathroom featuring dual vanities and a freestanding soaking tub. Four bedrooms and three and a half bathrooms offer flexibility across the home's three levels, while the two-car garage takes care of another practical detail. And then there is the elevator. Because three stories sound wonderful until you are carrying groceries, luggage, or a basket of laundry upstairs. The elevator handles the vertical commute so you can enjoy all that space without treating your own house like a stair-climbing competition. But here's the thing about 165 Hubbard Road. You can find beautiful kitchens. You can find big porches. You can find three-story homes and gorgeous bathrooms. What you cannot easily find is all of that in the middle of downtown Woodstock. Walk to dinner. Wander through the shops. Catch a concert. Meet friends for coffee. Come home and sit on your porch while the neighborhood settles into the evening. Three stories. Porches for days. An elevator. A fenced front yard. And a downtown Woodstock address that makes the whole thing even better. Some homes give you a great place to live. This one gives you a great place to live and a great place to be.

165 Hubbard Road, Woodstock

$890,000

LUXURY, LOCATION, AND LIFESTYLE – IN THE HEART OF DOWNTOWN WOODSTOCK Rarely does a Downtown Woodstock residence offer this combination of exceptional space, sophisticated finishes, corner unit natural light and true lock & leave convenience. Located in Woodstock Downtown’s sought after private community, 241 McAffee places the best of Woodstock just outside your door – restaurants, wine bars, breweries, coffee shops, boutique shopping, concerts, festivals, scenic walking/biking trails, and live entertainment – while offering an elevated retreat to come home to. A corner lot with just a small, shared wall on the second level, and nearly 3000 sq ft spanning three thoughtfully designed levels, this residence presents itself as a single-family home with the low maintenance ease and benefits of a townhome. The heart of the home is an entertainer’s delight - an expansive open concept living environment with chef’s kitchen, sitting room, breakfast area, formal dining and spectacular great room. The kitchen features Taj Mahal quartzite countertops and backsplash, a large chef’s island with a wide edge profile, cabinetry extending to the ceiling with undercounter lighting, walk-in pantry, Kitchen Aid appliances, double ovens and a separate ice maker. The kitchen flows into a light filled keeping room with a distinctive brick feature wall and direct access to the grilling porch. The dining room features a wall of floor-to-ceiling windows, a stunning Restoration Hardware chandelier, a largebar with lighted cabinetry, and beautiful quartzite countertops and backsplash. The spacious and elegant great room is enhanced by its coveted corner-unit setting, with expansive windows surrounding the space, a tile-surround fireplace flanked by handsome cabinets and floating shelves, and custom stained beams that add charm and elegance. A French door leads to the covered outdoor porch - perfect for relaxing and enjoying the Woodstock vibe. The upstairs features an oversized primary suite with a spa-inspired bath with dual vanities, soaking tub, generous shower and custom closet. A guest suite offers a private bath and large walk-in custom closet. The terrace level provides an additional bedroom, full bath and flexible space ideal for a den, office, exercise room or fourth bedroom. Woodstock Downtown is an exceptional neighborhood that offers the rare combination of true walkability and resort-style amenities. Residents enjoy PRIVATE access to a large resort style private swimming pool, amphitheater, and beautifully maintained park area, all while being able to walk or golf cart to everything Downtown Woodstock has to offer. Here, everyday living feels more like a getaway. Experience the rare combination of single-family home scale and privacy with the low maintenance ease of townhome living in the heart of Downtown Woodstock. A TURNKEY OPTION FOR THE DISCERNING BUYER – for those who prefer a completely effortless transition, the sellers are open to offering the home fully furnished, including furniture, artwork and décor by separate agreement, allowing you to step directly into the lifestyle Woodstock has to offer without the time and expense of furnishing a home of this scale. SPECIAL FEATURES: Elevator shaft frame for easy future installation, oversized water heater, corner unit with floor to ceiling windows, built-in ice maker, custom closets throughout, Nest thermostat, 10-foot ceilings on main level, custom granite garage floor and storage racks, covered extra concrete pad with gate for 3rd car or golf cart, premium lighting and customized motorized blinds and window coverings throughout the home, kitchen and bar quartzite countertops, large driveway allowing for additional parking, all-new exterior paint May 2026, and all-new interior paint refresh.

3 Beds ⋅ 4 Baths ⋅ 7830389 MLS ⋅ Woodstock Downtown BLDG.

LUXURY, LOCATION, AND LIFESTYLE – IN THE HEART OF DOWNTOWN WOODSTOCK Rarely does a Downtown Woodstock residence offer this combination of exceptional space, sophisticated finishes, corner unit natural light and true lock & leave convenience. Located in Woodstock Downtown’s sought after private community, 241 McAffee places the best of Woodstock just outside your door – restaurants, wine bars, breweries, coffee shops, boutique shopping, concerts, festivals, scenic walking/biking trails, and live entertainment – while offering an elevated retreat to come home to. A corner lot with just a small, shared wall on the second level, and nearly 3000 sq ft spanning three thoughtfully designed levels, this residence presents itself as a single-family home with the low maintenance ease and benefits of a townhome. The heart of the home is an entertainer’s delight - an expansive open concept living environment with chef’s kitchen, sitting room, breakfast area, formal dining and spectacular great room. The kitchen features Taj Mahal quartzite countertops and backsplash, a large chef’s island with a wide edge profile, cabinetry extending to the ceiling with undercounter lighting, walk-in pantry, Kitchen Aid appliances, double ovens and a separate ice maker. The kitchen flows into a light filled keeping room with a distinctive brick feature wall and direct access to the grilling porch. The dining room features a wall of floor-to-ceiling windows, a stunning Restoration Hardware chandelier, a largebar with lighted cabinetry, and beautiful quartzite countertops and backsplash. The spacious and elegant great room is enhanced by its coveted corner-unit setting, with expansive windows surrounding the space, a tile-surround fireplace flanked by handsome cabinets and floating shelves, and custom stained beams that add charm and elegance. A French door leads to the covered outdoor porch - perfect for relaxing and enjoying the Woodstock vibe. The upstairs features an oversized primary suite with a spa-inspired bath with dual vanities, soaking tub, generous shower and custom closet. A guest suite offers a private bath and large walk-in custom closet. The terrace level provides an additional bedroom, full bath and flexible space ideal for a den, office, exercise room or fourth bedroom. Woodstock Downtown is an exceptional neighborhood that offers the rare combination of true walkability and resort-style amenities. Residents enjoy PRIVATE access to a large resort style private swimming pool, amphitheater, and beautifully maintained park area, all while being able to walk or golf cart to everything Downtown Woodstock has to offer. Here, everyday living feels more like a getaway. Experience the rare combination of single-family home scale and privacy with the low maintenance ease of townhome living in the heart of Downtown Woodstock. A TURNKEY OPTION FOR THE DISCERNING BUYER – for those who prefer a completely effortless transition, the sellers are open to offering the home fully furnished, including furniture, artwork and décor by separate agreement, allowing you to step directly into the lifestyle Woodstock has to offer without the time and expense of furnishing a home of this scale. SPECIAL FEATURES: Elevator shaft frame for easy future installation, oversized water heater, corner unit with floor to ceiling windows, built-in ice maker, custom closets throughout, Nest thermostat, 10-foot ceilings on main level, custom granite garage floor and storage racks, covered extra concrete pad with gate for 3rd car or golf cart, premium lighting and customized motorized blinds and window coverings throughout the home, kitchen and bar quartzite countertops, large driveway allowing for additional parking, all-new exterior paint May 2026, and all-new interior paint refresh.

241 Mcaffee Street, Woodstock

$340,000

Woodstock Downtown Money Magazine voted TOP 50th Town to Live!!! Walkable to the best Restaurants, City Parks, Greenprint Trials, Boutiques, Shopping, Farmers Market, Elm Streets Art, New Amphitheater and much more. Stunning 1 Bedroom, 1 Full Bath (ON THE 4TH FLOOR -NO ONE ABOVE YOU) - Open Floorplan- oversized master suite with large shower. Gated Covered Parking Spot!!! THIS ONE WILL NOT LAST!!!!

1 Beds ⋅ 1 Baths ⋅ 7676352 MLS ⋅ Woodstock Downtown BLDG.

Woodstock Downtown Money Magazine voted TOP 50th Town to Live!!! Walkable to the best Restaurants, City Parks, Greenprint Trials, Boutiques, Shopping, Farmers Market, Elm Streets Art, New Amphitheater and much more. Stunning 1 Bedroom, 1 Full Bath (ON THE 4TH FLOOR -NO ONE ABOVE YOU) - Open Floorplan- oversized master suite with large shower. Gated Covered Parking Spot!!! THIS ONE WILL NOT LAST!!!!

360 Chambers Street Unit 411, Woodstock

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