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Set on a scenic hilltop, this enchanting property offers views and 1,000 feet of frontage along the stunning Green River, complete with private swimming holes. The landscape is a beautiful blend of rolling meadows, mixed woodland, gardens & stone walls--creating a magical setting. The property also includes a charming sleeping cottage, a utility shed, & a storage shed, offering flexibility for guests, hobbies, or additional storage. The main home is filled with natural light, featuring expansive windows that frame the surrounding views, along with a spacious front deck ideal for relaxing or entertaining during three seasons. Inside, the home exudes warmth and character, with rich wood accents, exposed beam work, and an abundance of handcrafted cabinetry throughout. Enter through the front porch into a welcoming mudroom with wood flooring, bench, and closet, along with direct access to the attached two-car garage with electric doors and overhead storage. The kitchen is both charming and functional, offering wood and tile countertops, ash flooring, maple cabinetry, walk-in pantry, and a convenient laundry area. Adjacent, the formal dining room features wide pine flooring, brick fireplace with propane stove insert, and patio doors that open to the front deck. The expansive living room is anchored by a brick hearth with wood stove, and is complemented by numerous handcrafted built-ins, including desks, and large windows that flood the space with light, along with access to the side yard. The first floor also includes an intimate bedroom with dressing area and a nearby tiled bath. Upstairs, a spacious landing leads to the primary bedroom with walk-in closet and built-in desk, an additional generously sized bedroom, a dedicated office, and a second tiled bathroom. This is an opportunity to own a thoughtfully designed, light-filled home in an extraordinary natural setting-where charm, privacy and beauty come together seamlessly. House is not in flood zone, only the river.

3 Beds ⋅ 2 Baths ⋅ 5095214 MLS

Set on a scenic hilltop, this enchanting property offers views and 1,000 feet of frontage along the stunning Green River, complete with private swimming holes. The landscape is a beautiful blend of rolling meadows, mixed woodland, gardens & stone walls--creating a magical setting. The property also includes a charming sleeping cottage, a utility shed, & a storage shed, offering flexibility for guests, hobbies, or additional storage. The main home is filled with natural light, featuring expansive windows that frame the surrounding views, along with a spacious front deck ideal for relaxing or entertaining during three seasons. Inside, the home exudes warmth and character, with rich wood accents, exposed beam work, and an abundance of handcrafted cabinetry throughout. Enter through the front porch into a welcoming mudroom with wood flooring, bench, and closet, along with direct access to the attached two-car garage with electric doors and overhead storage. The kitchen is both charming and functional, offering wood and tile countertops, ash flooring, maple cabinetry, walk-in pantry, and a convenient laundry area. Adjacent, the formal dining room features wide pine flooring, brick fireplace with propane stove insert, and patio doors that open to the front deck. The expansive living room is anchored by a brick hearth with wood stove, and is complemented by numerous handcrafted built-ins, including desks, and large windows that flood the space with light, along with access to the side yard. The first floor also includes an intimate bedroom with dressing area and a nearby tiled bath. Upstairs, a spacious landing leads to the primary bedroom with walk-in closet and built-in desk, an additional generously sized bedroom, a dedicated office, and a second tiled bathroom. This is an opportunity to own a thoughtfully designed, light-filled home in an extraordinary natural setting-where charm, privacy and beauty come together seamlessly. House is not in flood zone, only the river.

1736 River Rd, Guilford

$651,000

A truly magical setting! If you've never experienced the blissfulness of the Green River Village and its historic covered bridge and crib dam/waterfall and one of the most spectacular swimming holes imaginable, it's a must visit southern Vermont destination. Nestled in this picturesque valley village is this charming old home privately situated on 53.5 acres only a short stroll up the driveway from this beautiful waterfall scene. With its open fields, outstanding sun exposure, pond, stonework, established gardens, berry bushes and apple, pear and peach trees this setting will transport you back in time. The towering old growth sugar maples around the house are true giants and are one of the first things that will make your jaw drop as you enter the peaceful homestead. The house needs work but with this stunning location and unique property attributes it's deserving and worthy of the investment. The 4-bedroom, 2.5 bath home features original fir flooring throughout the old portion and oak flooring in the addition, a huge 18' X 34' living/dining room a fireplace and massive hearth, a country kitchen with antique wood cookstove, an office/study (or 1st floor bedroom) and a small bath and laundry on the main level and 3 bedrooms, bath and the primary bedroom suite upstairs. The central heating system was propane hot water baseboard but is not functional at present. The owner currently heats with wood only. Freshly painted in 2025. Roof replaced with standing seam metal in 2005. Property is enrolled in the Use Value Appraisal (current use) with 8 acres excluded encompassing the open land, gardens and pond area around the home site. The true southern exposure, local views of the hills surrounding the river valley, access to the river and the privacy this property provides is special and very difficult to find.

4 Beds ⋅ 3 Baths ⋅ 5088798 MLS

A truly magical setting! If you've never experienced the blissfulness of the Green River Village and its historic covered bridge and crib dam/waterfall and one of the most spectacular swimming holes imaginable, it's a must visit southern Vermont destination. Nestled in this picturesque valley village is this charming old home privately situated on 53.5 acres only a short stroll up the driveway from this beautiful waterfall scene. With its open fields, outstanding sun exposure, pond, stonework, established gardens, berry bushes and apple, pear and peach trees this setting will transport you back in time. The towering old growth sugar maples around the house are true giants and are one of the first things that will make your jaw drop as you enter the peaceful homestead. The house needs work but with this stunning location and unique property attributes it's deserving and worthy of the investment. The 4-bedroom, 2.5 bath home features original fir flooring throughout the old portion and oak flooring in the addition, a huge 18' X 34' living/dining room a fireplace and massive hearth, a country kitchen with antique wood cookstove, an office/study (or 1st floor bedroom) and a small bath and laundry on the main level and 3 bedrooms, bath and the primary bedroom suite upstairs. The central heating system was propane hot water baseboard but is not functional at present. The owner currently heats with wood only. Freshly painted in 2025. Roof replaced with standing seam metal in 2005. Property is enrolled in the Use Value Appraisal (current use) with 8 acres excluded encompassing the open land, gardens and pond area around the home site. The true southern exposure, local views of the hills surrounding the river valley, access to the river and the privacy this property provides is special and very difficult to find.

2416 Stage Rd, Guilford

$610,000

A picturesque, private home with lovely views from every room. Set back from the road in a pastoral setting, it is quiet and tranquil. The moment you enter through the front covered porch, you are greeted by abundant natural light and breathtaking views. The open floor concept is inviting, and the beautiful timbers were milled from the land. The original owner, who has owned the home for 47 years, adores it. The spacious and peaceful living room features a soothing fireplace. The first floor has a large primary bedroom, a full bath, a laundry room, and another room perfect for an office or bonus room. Upstairs are two spacious bedrooms and another full bathroom. The full basement is ideal for a workshop, featuring additional heat with a wood boiler and a walk-out exit. The 10 x 27 screened-in porch is ideal for family gatherings, and the expansive Trex decks, along with the alluring pool and hot tub, will create lasting memories. The location offers seclusion and accessibility, situated minutes from the historic Guilford Country store and Interstate 91. You will love coming home and never want to leave. Additional 2.8 +/- acreage available for $89,000 only with house purchase.

3 Beds ⋅ 2 Baths ⋅ 5087831 MLS

A picturesque, private home with lovely views from every room. Set back from the road in a pastoral setting, it is quiet and tranquil. The moment you enter through the front covered porch, you are greeted by abundant natural light and breathtaking views. The open floor concept is inviting, and the beautiful timbers were milled from the land. The original owner, who has owned the home for 47 years, adores it. The spacious and peaceful living room features a soothing fireplace. The first floor has a large primary bedroom, a full bath, a laundry room, and another room perfect for an office or bonus room. Upstairs are two spacious bedrooms and another full bathroom. The full basement is ideal for a workshop, featuring additional heat with a wood boiler and a walk-out exit. The 10 x 27 screened-in porch is ideal for family gatherings, and the expansive Trex decks, along with the alluring pool and hot tub, will create lasting memories. The location offers seclusion and accessibility, situated minutes from the historic Guilford Country store and Interstate 91. You will love coming home and never want to leave. Additional 2.8 +/- acreage available for $89,000 only with house purchase.

49 Oles Dr, Guilford

$475,000

This property is arguably one of the most extraordinary pieces of land of its size in southeastern Vermont. With 106+- acres; The view from the top of the 6-acre field is nothing short of spectacular with sweeping extensive views & beautiful sunsets. Peace and tranquility abound. Nature abounds here, with the northern property line marked by an ancient, magnificent stone wall that separates Guilford and Brattleboro. If those walls could talk, what stories they could tell! In spring, you will know when the honey locust trees bloom on Star Dust Hill; the fragrance drifts through the air—it's truly magical. Established as part of Kindness Farm circa 1785, the property holds traces of history waiting to be discovered as you explore its ecologically diverse acreage. The land features a long road frontage, and power and internet are available at the street. Access to town is via well-maintained roads. This would be a perfect spot for equestrians to live out their dreams. The dark night sky is excellent for stargazing, and the property boasts hundreds of feet along the clear, cool waters of Broad Brook. In the neighborhood is The Bonnyvale Environmental Education Center. Easy access to downtown Brattleboro with a bucolic setting. A little over 2 hours to Boston and 3.5 hours to NYC, 35 minutes to Mount Snow.

5049450 MLS

This property is arguably one of the most extraordinary pieces of land of its size in southeastern Vermont. With 106+- acres; The view from the top of the 6-acre field is nothing short of spectacular with sweeping extensive views & beautiful sunsets. Peace and tranquility abound. Nature abounds here, with the northern property line marked by an ancient, magnificent stone wall that separates Guilford and Brattleboro. If those walls could talk, what stories they could tell! In spring, you will know when the honey locust trees bloom on Star Dust Hill; the fragrance drifts through the air—it's truly magical. Established as part of Kindness Farm circa 1785, the property holds traces of history waiting to be discovered as you explore its ecologically diverse acreage. The land features a long road frontage, and power and internet are available at the street. Access to town is via well-maintained roads. This would be a perfect spot for equestrians to live out their dreams. The dark night sky is excellent for stargazing, and the property boasts hundreds of feet along the clear, cool waters of Broad Brook. In the neighborhood is The Bonnyvale Environmental Education Center. Easy access to downtown Brattleboro with a bucolic setting. A little over 2 hours to Boston and 3.5 hours to NYC, 35 minutes to Mount Snow.

2745 Bonnyvale Rd, Guilford

$425,000

This one is the right one! So very special, nestled in the countryside just waiting.... So many options to choose from...a first floor main bedroom is perfect for aging in place, an x gen who still lives at home, in-law suite...or...perfect for an Air B&B. The other main bedroom features a walk out to the upper gardens, vaulted ceilings, room for a private getaway or reading nook. Plenty of space in between with lovely shiny wood floors, an open floor plan so you can direct the cook...working away in the modern wrap kitchen with center island, huge windows and lots of light. And everywhere you look is green, stone walls, gardens, shady trees and just plain Vermont country. Pop across the road to the banks of the Broad Brook and dip your toes. Great mud room...but...No mud season here, just beautiful snowfalls, glowing foliage and chirping birds. Enjoy it all from the huge deck and let the OTHERS wish they were here. Open House - Saturday, July 26th from 11 am - 1 pm

4 Beds ⋅ 2 Baths ⋅ 5052961 MLS

This one is the right one! So very special, nestled in the countryside just waiting.... So many options to choose from...a first floor main bedroom is perfect for aging in place, an x gen who still lives at home, in-law suite...or...perfect for an Air B&B. The other main bedroom features a walk out to the upper gardens, vaulted ceilings, room for a private getaway or reading nook. Plenty of space in between with lovely shiny wood floors, an open floor plan so you can direct the cook...working away in the modern wrap kitchen with center island, huge windows and lots of light. And everywhere you look is green, stone walls, gardens, shady trees and just plain Vermont country. Pop across the road to the banks of the Broad Brook and dip your toes. Great mud room...but...No mud season here, just beautiful snowfalls, glowing foliage and chirping birds. Enjoy it all from the huge deck and let the OTHERS wish they were here. Open House - Saturday, July 26th from 11 am - 1 pm

17 Tinker Hill Rd, Guilford

$367,500

Beautiful north and westerly views! This sweet 2-bedroom, 2-bath, low maintenance home with a 2-car garage was built in 2004 and handsomely sits perched atop of a gentle hill and overlooks the rolling knolls and the pretty fields below. A stone's throw to the historic Guilford Store and Cafe- have your morning coffee and muffin there, at your kitchen table or out on your side deck overlooking the views. The property is located on maple tree-lined country dead-end road bordered by a stone wall and less than 1.5 miles to exit 1. You are close to it all yet in a bucolic rural setting. Inside the home, you will find updated kitchen with new appliances, enormous windows that allow for an abundance of light and access to the views, and easy to care for floors. There is a nice flow to the home. Owner have recently invested an upwards of approx. $25,000.00 into materials and labor to rough-in, insulate and plumb the basement for additional living space and a full bath. The garage is over-sized and has french doors in case you'd like to convert some of it into studio space. The property has its own delicious well water and is on town sewer. The town of Guilford has no zoning restrictions. Owners have priced this extremely fairly so make your appointment ASAP. This sale is contingent on them closing on suitable housing, in which they are currently under contract.

2 Beds ⋅ 2 Baths ⋅ 5065647 MLS

Beautiful north and westerly views! This sweet 2-bedroom, 2-bath, low maintenance home with a 2-car garage was built in 2004 and handsomely sits perched atop of a gentle hill and overlooks the rolling knolls and the pretty fields below. A stone's throw to the historic Guilford Store and Cafe- have your morning coffee and muffin there, at your kitchen table or out on your side deck overlooking the views. The property is located on maple tree-lined country dead-end road bordered by a stone wall and less than 1.5 miles to exit 1. You are close to it all yet in a bucolic rural setting. Inside the home, you will find updated kitchen with new appliances, enormous windows that allow for an abundance of light and access to the views, and easy to care for floors. There is a nice flow to the home. Owner have recently invested an upwards of approx. $25,000.00 into materials and labor to rough-in, insulate and plumb the basement for additional living space and a full bath. The garage is over-sized and has french doors in case you'd like to convert some of it into studio space. The property has its own delicious well water and is on town sewer. The town of Guilford has no zoning restrictions. Owners have priced this extremely fairly so make your appointment ASAP. This sale is contingent on them closing on suitable housing, in which they are currently under contract.

257 Partridge Rd, Guilford

$350,000

3 Beds ⋅ 1 Baths ⋅ 5112317 MLS

3242 Tater Ln, Guilford

$325,000

Welcome to a bright, airy home that blends comfort, character, and convenience! Set on 1.26 acres of sunny lawn and wooded privacy, this four-bedroom, two-bath property offers inviting, freshly painted living spaces, central air, and efficient baseboard radiant heat. The living room features a welcoming fireplace, while the kitchen includes a woodstove setup and comes fully applianced with a dishwasher, refrigerator, gas stove, microwave, washer, and dryer. Upstairs, the primary bedroom makes a memorable impression with its vaulted ceiling and exposed brick chimney, adding warmth and architectural charm. Floors are easy to maintain light-toned vinyl planks with carpeted stairs for quiet. Practical features include a drilled well and town sewer, offering ease of ownership in a desirable setting. The location is especially convenient, just a short distance to Exit 1, making it easy to access nearby services, commuting routes, and local amenities. With character-filled details and a 1.26-acre setting, this property is ready to welcome its next owner.

4 Beds ⋅ 2 Baths ⋅ 5101085 MLS

Welcome to a bright, airy home that blends comfort, character, and convenience! Set on 1.26 acres of sunny lawn and wooded privacy, this four-bedroom, two-bath property offers inviting, freshly painted living spaces, central air, and efficient baseboard radiant heat. The living room features a welcoming fireplace, while the kitchen includes a woodstove setup and comes fully applianced with a dishwasher, refrigerator, gas stove, microwave, washer, and dryer. Upstairs, the primary bedroom makes a memorable impression with its vaulted ceiling and exposed brick chimney, adding warmth and architectural charm. Floors are easy to maintain light-toned vinyl planks with carpeted stairs for quiet. Practical features include a drilled well and town sewer, offering ease of ownership in a desirable setting. The location is especially convenient, just a short distance to Exit 1, making it easy to access nearby services, commuting routes, and local amenities. With character-filled details and a 1.26-acre setting, this property is ready to welcome its next owner.

36 Pauls Rd Unit 6-259, Guilford

$301,000

Discover classic country living in this inviting 3-bedroom, 1-bath home situated on a generous 5-acre parcel. The property blends simple, comfortable living with wide-open outdoor possibilities — think gardening, large or small livestock, or just relax. Inside, the home greets you with a bright living area, a functional kitchen with ample counter space, and three well-proportioned bedrooms served by a single, updated full bathroom. Wood-accent details and original charm. Outside, the expansive lot provides privacy and endless potential: fenced in arena, a handy outbuilding or workshop, and plenty of room for future additions like a garage, or outbuildings. Quiet country roads, starry nights, and the sounds of nature make this an ideal retreat from the bustle, while nearby town amenities and commuter routes remain within easy reach. Don’t miss this rare chance to own five acres and a cute as can be home.

3 Beds ⋅ 1 Baths ⋅ 5067195 MLS

Discover classic country living in this inviting 3-bedroom, 1-bath home situated on a generous 5-acre parcel. The property blends simple, comfortable living with wide-open outdoor possibilities — think gardening, large or small livestock, or just relax. Inside, the home greets you with a bright living area, a functional kitchen with ample counter space, and three well-proportioned bedrooms served by a single, updated full bathroom. Wood-accent details and original charm. Outside, the expansive lot provides privacy and endless potential: fenced in arena, a handy outbuilding or workshop, and plenty of room for future additions like a garage, or outbuildings. Quiet country roads, starry nights, and the sounds of nature make this an ideal retreat from the bustle, while nearby town amenities and commuter routes remain within easy reach. Don’t miss this rare chance to own five acres and a cute as can be home.

2380 Guilford Center Rd, Guilford

$275,000

Discover a truly transformative living experience at here where modern architectural design meets the serene landscapes of Guilford, Vermont. This exceptional property features a permanent yurt conversion, meticulously crafted into a sophisticated single-family residence situated on a prime 1.5-acre parcel. The interior is characterized by soaring radial ceilings and an open-concept layout that feels both expansive and intimate. At the heart of the home, a high-efficiency pellet stove sits on a stone hearth providing a warm, grounding focal point for the main living area that is perfectly complemented by the rustic wooden beams and lattice-work walls. Ductless mini splits provide additional heat in the winter and a/c in the summer! The chef’s kitchen is a bold design statement, featuring striking cobalt blue cabinetry contrasted with sunny yellow accents, warm butcher-block countertops, and premium stainless steel appliances including a built-in wall oven and glass cooktop. Unlike traditional seasonal structures, this home is fully equipped for year-round permanent living, boasting a modern bathroom complete with a deep soaking tub, integrated laundry station with a stacked washer and dryer, and contemporary fixtures. The property also includes a versatile detached workshop or barn with a green metal roof, providing ample space for creative projects, storage, or a home studio. Whether you are seeking a peaceful full-time sanctuary or a world-class retreat, this Guilford gem offers an unparalleled opportunity to live within a piece of functional art. With its strategic location on Weatherhead Hollow Road, you enjoy the ultimate privacy of the Vermont countryside while remaining connected to the vibrant local community. Open House Sunday April 26th 12pm-2pm

1 Beds ⋅ 1 Baths ⋅ 5085145 MLS

Discover a truly transformative living experience at here where modern architectural design meets the serene landscapes of Guilford, Vermont. This exceptional property features a permanent yurt conversion, meticulously crafted into a sophisticated single-family residence situated on a prime 1.5-acre parcel. The interior is characterized by soaring radial ceilings and an open-concept layout that feels both expansive and intimate. At the heart of the home, a high-efficiency pellet stove sits on a stone hearth providing a warm, grounding focal point for the main living area that is perfectly complemented by the rustic wooden beams and lattice-work walls. Ductless mini splits provide additional heat in the winter and a/c in the summer! The chef’s kitchen is a bold design statement, featuring striking cobalt blue cabinetry contrasted with sunny yellow accents, warm butcher-block countertops, and premium stainless steel appliances including a built-in wall oven and glass cooktop. Unlike traditional seasonal structures, this home is fully equipped for year-round permanent living, boasting a modern bathroom complete with a deep soaking tub, integrated laundry station with a stacked washer and dryer, and contemporary fixtures. The property also includes a versatile detached workshop or barn with a green metal roof, providing ample space for creative projects, storage, or a home studio. Whether you are seeking a peaceful full-time sanctuary or a world-class retreat, this Guilford gem offers an unparalleled opportunity to live within a piece of functional art. With its strategic location on Weatherhead Hollow Road, you enjoy the ultimate privacy of the Vermont countryside while remaining connected to the vibrant local community. Open House Sunday April 26th 12pm-2pm

757 Weatherhead Hollow Rd, Guilford

$225,000

Tucked back off the road, equidistant between Brattleboro, Vermont and Bernardston, MA, this “cute-as-a-button,” chalet-influenced cape is an excellent opportunity for a cozy, 3-bedroom home or an Airbnb, on a 7.9-ac lot in beautiful Guilford, Vermont. Nice mix of sun and shade. Excellent gardening spot. High-speed internet available. Single-level living is possible, with a first-floor bedroom and its own private entrance to the spacious full bath. Comfortable, wood-paneled living room with a grand, stone fireplace soaring up to the cathedral ceiling. Fireplace is ready for efficient woodstove insert, or keep authentic. Two additional bedrooms (or alternative use) on second floor. Traditional oil-fired hot-air furnace as primary heat. Detached, 20’ x 12’, 1-car garage. Don’t miss this affordable Guilford, country property. Delayed showings begin August 1, 2025.

3 Beds ⋅ 1 Baths ⋅ 5053696 MLS

Tucked back off the road, equidistant between Brattleboro, Vermont and Bernardston, MA, this “cute-as-a-button,” chalet-influenced cape is an excellent opportunity for a cozy, 3-bedroom home or an Airbnb, on a 7.9-ac lot in beautiful Guilford, Vermont. Nice mix of sun and shade. Excellent gardening spot. High-speed internet available. Single-level living is possible, with a first-floor bedroom and its own private entrance to the spacious full bath. Comfortable, wood-paneled living room with a grand, stone fireplace soaring up to the cathedral ceiling. Fireplace is ready for efficient woodstove insert, or keep authentic. Two additional bedrooms (or alternative use) on second floor. Traditional oil-fired hot-air furnace as primary heat. Detached, 20’ x 12’, 1-car garage. Don’t miss this affordable Guilford, country property. Delayed showings begin August 1, 2025.

5704 Coolidge Hwy, Guilford

part of 215 Part Of 215 Melendy Hill Road, Guilford

$101,000

Just past the Guilford Store and a short drive up Melendy Hill Rd sits this 23.60+/- acres of forest land. This wonderful property offers 2 delightful brooks, Broad Brook to the west and north and a smaller brook that’s closer to Melendy Hill Rd. The parcel features a mixed forest consisting of large stands of pine and hemlock with the east side offering a good mix of hardwoods. Great views should be visible from the height of the land with cutting. Wildlife of all varieties call this land home and it could be your perfect getaway spot or full-time home too.

5065293 MLS

Just past the Guilford Store and a short drive up Melendy Hill Rd sits this 23.60+/- acres of forest land. This wonderful property offers 2 delightful brooks, Broad Brook to the west and north and a smaller brook that’s closer to Melendy Hill Rd. The parcel features a mixed forest consisting of large stands of pine and hemlock with the east side offering a good mix of hardwoods. Great views should be visible from the height of the land with cutting. Wildlife of all varieties call this land home and it could be your perfect getaway spot or full-time home too.

part of 215 Part Of 215 Melendy Hill Road, Guilford

$65,000

This two story home offers 3 bedrooms/1 bathroom with 1,490 sq. ft. of living space. The property sits on a 0.50 acre lot. The first floor has a kitchen with wooden cabinets and granite countertops, wood flooring and a carpeted living room. A dedicated laundry area is also included. The property features a barn in the backyard for storage. Exterior highlights include a covered front entry, driveway parking, and a side deck for outdoor use. Mature trees surround the lot, providing a natural setting.

3 Beds ⋅ 1 Baths ⋅ 5060709 MLS

This two story home offers 3 bedrooms/1 bathroom with 1,490 sq. ft. of living space. The property sits on a 0.50 acre lot. The first floor has a kitchen with wooden cabinets and granite countertops, wood flooring and a carpeted living room. A dedicated laundry area is also included. The property features a barn in the backyard for storage. Exterior highlights include a covered front entry, driveway parking, and a side deck for outdoor use. Mature trees surround the lot, providing a natural setting.

7 Nichols Dr, Guilford