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Exceptionally rare, The Howe Quarry Cliff House is a truly one-of-a-kind property set on 25+ private forested acres, dramatically positioned atop a cliff overlooking the historic quarry and pond. The setting offers remarkable 180-degree unobstructed views stretching from the Hartford skyline to Sleeping Giant in New Haven, the Connecticut River Valley, Portland Bridge, and the rolling fields of South Glastonbury-along with spectacular sunsets night after night. Designed to embrace its extraordinary surroundings, this custom-built single story home captures the views from nearly every room, including dramatic perspectives directly into the Quarry below. From the deck and porch, watch eagles & hawks soar at eye level and enjoy a sense of privacy that is difficult to find, all just minutes from the village of South Glastonbury. Recently renovated from top to bottom, the home blends naturally with its setting through warm, earthy tones, wood cabinetry, wide-board floors, and abundant windows. The main living and dining area features a striking floor-to-ceiling fireplace constructed with stone from the Quarry itself. The primary and guest bedrooms each offer beautifully appointed stone bathrooms inspired by the surrounding landscape. An attached two-car garage is complemented by an additional lower-level garage with direct basement access-ideal for ATVs, outdoor equipment, and recreational gear.

2 Beds ⋅ 3 Baths ⋅ 24201786 MLS

Exceptionally rare, The Howe Quarry Cliff House is a truly one-of-a-kind property set on 25+ private forested acres, dramatically positioned atop a cliff overlooking the historic quarry and pond. The setting offers remarkable 180-degree unobstructed views stretching from the Hartford skyline to Sleeping Giant in New Haven, the Connecticut River Valley, Portland Bridge, and the rolling fields of South Glastonbury-along with spectacular sunsets night after night. Designed to embrace its extraordinary surroundings, this custom-built single story home captures the views from nearly every room, including dramatic perspectives directly into the Quarry below. From the deck and porch, watch eagles & hawks soar at eye level and enjoy a sense of privacy that is difficult to find, all just minutes from the village of South Glastonbury. Recently renovated from top to bottom, the home blends naturally with its setting through warm, earthy tones, wood cabinetry, wide-board floors, and abundant windows. The main living and dining area features a striking floor-to-ceiling fireplace constructed with stone from the Quarry itself. The primary and guest bedrooms each offer beautifully appointed stone bathrooms inspired by the surrounding landscape. An attached two-car garage is complemented by an additional lower-level garage with direct basement access-ideal for ATVs, outdoor equipment, and recreational gear.

400 Dayton Rd, Glastonbury

$799,000

Welcome to 320 Overlook Rd a truly exceptional South Glastonbury residence, where refined design and meticulous attention to detail are evident throughout. Thoughtfully renovated and owned by an interior designer, this impeccably maintained home offers appoximately 3000 square feet of beautifully finished living space, including a 450-square-foot finished basement. The heart of the home is a stunning custom kitchen featuring exquisite beaded-inlay cabinetry and designer finishes. A dramatic double-sided gas fireplace adds warmth and elegance, while custom walls and architectural details create a sophisticated yet inviting atmosphere throughout. The spacious three-season porch is a standout feature, offering generous room for entertaining and relaxing while overlooking the beautifully landscaped grounds. Step outside to a gorgeous patio with pergola and dedicated seating area, surrounded by professionally designed gardens and gorgeous perennial plantings on nearly an acre of private, picturesque property. A large studio/office or potential fourth bedroom provides exceptional flexibility and includes its own private entrance-ideal for a home office, creative studio, guest suite, or multi-generational living. Every room reflects thoughtful design, quality craftsmanship, and impeccable taste. From the custom finishes to the professionally landscaped grounds, this is a truly special property.

3 Beds ⋅ 2 Baths ⋅ 24199837 MLS

Welcome to 320 Overlook Rd a truly exceptional South Glastonbury residence, where refined design and meticulous attention to detail are evident throughout. Thoughtfully renovated and owned by an interior designer, this impeccably maintained home offers appoximately 3000 square feet of beautifully finished living space, including a 450-square-foot finished basement. The heart of the home is a stunning custom kitchen featuring exquisite beaded-inlay cabinetry and designer finishes. A dramatic double-sided gas fireplace adds warmth and elegance, while custom walls and architectural details create a sophisticated yet inviting atmosphere throughout. The spacious three-season porch is a standout feature, offering generous room for entertaining and relaxing while overlooking the beautifully landscaped grounds. Step outside to a gorgeous patio with pergola and dedicated seating area, surrounded by professionally designed gardens and gorgeous perennial plantings on nearly an acre of private, picturesque property. A large studio/office or potential fourth bedroom provides exceptional flexibility and includes its own private entrance-ideal for a home office, creative studio, guest suite, or multi-generational living. Every room reflects thoughtful design, quality craftsmanship, and impeccable taste. From the custom finishes to the professionally landscaped grounds, this is a truly special property.

320 Overlook Rd, Glastonbury

$740,000

Welcome to 179 Sherwood Drive, a custom-built Colonial privately set on 1.37 acres in one of Glastonbury's most desirable neighborhoods. Offering over 3,250 square feet of beautifully designed living space, this exceptional 4-bedroom, 3-bath home combines timeless craftsmanship, comfort, and functionality. The sought-after first-floor primary suite provides a peaceful retreat, featuring separate walk-in closets and a luxurious bath with a whirlpool tub. A private first-floor office with French doors offers the perfect space for working from home. At the heart of the home, the impressive family room showcases soaring cathedral ceilings,4 skylights and a striking marble fireplace, creating a warm and inviting atmosphere for everyday living and entertaining. The spacious eat-in kitchen is filled with natural light from skylights and features granite countertops, a large center island, and abundant prep and storage space. Enjoy breathtaking Hartford skyline views from the sunroom or step outside to the large trex deck overlooking the beautifully landscaped, partially wooded grounds. The private setting provides the perfect backdrop for relaxing, entertaining, and enjoying nature. Additional features, full unfinished walkout basement with endless potential for future expansion, central vacuum, a security system, Kohler whole-house generator, roof de-icing system, and an attached two-car garage. Constructed with quality stone-and-clapboard. New roof 2025, new water heater 2026.

4 Beds ⋅ 3 Baths ⋅ 24195994 MLS

Welcome to 179 Sherwood Drive, a custom-built Colonial privately set on 1.37 acres in one of Glastonbury's most desirable neighborhoods. Offering over 3,250 square feet of beautifully designed living space, this exceptional 4-bedroom, 3-bath home combines timeless craftsmanship, comfort, and functionality. The sought-after first-floor primary suite provides a peaceful retreat, featuring separate walk-in closets and a luxurious bath with a whirlpool tub. A private first-floor office with French doors offers the perfect space for working from home. At the heart of the home, the impressive family room showcases soaring cathedral ceilings,4 skylights and a striking marble fireplace, creating a warm and inviting atmosphere for everyday living and entertaining. The spacious eat-in kitchen is filled with natural light from skylights and features granite countertops, a large center island, and abundant prep and storage space. Enjoy breathtaking Hartford skyline views from the sunroom or step outside to the large trex deck overlooking the beautifully landscaped, partially wooded grounds. The private setting provides the perfect backdrop for relaxing, entertaining, and enjoying nature. Additional features, full unfinished walkout basement with endless potential for future expansion, central vacuum, a security system, Kohler whole-house generator, roof de-icing system, and an attached two-car garage. Constructed with quality stone-and-clapboard. New roof 2025, new water heater 2026.

179 Sherwood Dr, Glastonbury

$648,888

You know that house where the listing says, "some updates needed" and suddenly your Saturday plans involve a dumpster, three contractors, and a trip to Home Depot? Yeah...this isn't that house. This fully updated 4-bedroom, 2 1/2-bathroom South Glastonbury-beauty sits on almost 2 ACRES and offers 2,382 square feet of living space, plus a 2-car garage. And the update list is giving serious "we already did all the expensive stuff" energy: NEW ROOF, NEW FULL HVAC SYSTEM, NEW WELL PUMP & TANK, UPDATED/NEW CHIMNEY, NEW WINDOWS, NEW PATIO, NEW LIGHTING...and MUCH MORE. Translation? You bring the moving truck. Someone else already brought the checkbook. -- Outside, nearly two acres gives you room to actually enjoy your property. Want a garden? Go for it. Pool? There's room. Backyard football league? Probably. Want to sit on the patio with a drink and tell everyone, "Yep, we bought this one"? Also acceptable. - Inside, you'll have plenty of room for family, guests, an office, or that one bedroom that mysteriously becomes a storage facility within six months of moving in.-Located in desirable South Glastonbury, close to everything that makes this area so popular-while still having the space and privacy that make you feel like you escaped somewhere.-4 bedrooms. 21/2 baths. 2,382 sq ft. 2-car garage. Fully updated.-The only thing this house appears to be missing is your stuff.-45 Toll Gate-Come see it before somebody else does-and then inevitably tells you, "We should have bought that!"

4 Beds ⋅ 3 Baths ⋅ 24206708 MLS

You know that house where the listing says, "some updates needed" and suddenly your Saturday plans involve a dumpster, three contractors, and a trip to Home Depot? Yeah...this isn't that house. This fully updated 4-bedroom, 2 1/2-bathroom South Glastonbury-beauty sits on almost 2 ACRES and offers 2,382 square feet of living space, plus a 2-car garage. And the update list is giving serious "we already did all the expensive stuff" energy: NEW ROOF, NEW FULL HVAC SYSTEM, NEW WELL PUMP & TANK, UPDATED/NEW CHIMNEY, NEW WINDOWS, NEW PATIO, NEW LIGHTING...and MUCH MORE. Translation? You bring the moving truck. Someone else already brought the checkbook. -- Outside, nearly two acres gives you room to actually enjoy your property. Want a garden? Go for it. Pool? There's room. Backyard football league? Probably. Want to sit on the patio with a drink and tell everyone, "Yep, we bought this one"? Also acceptable. - Inside, you'll have plenty of room for family, guests, an office, or that one bedroom that mysteriously becomes a storage facility within six months of moving in.-Located in desirable South Glastonbury, close to everything that makes this area so popular-while still having the space and privacy that make you feel like you escaped somewhere.-4 bedrooms. 21/2 baths. 2,382 sq ft. 2-car garage. Fully updated.-The only thing this house appears to be missing is your stuff.-45 Toll Gate-Come see it before somebody else does-and then inevitably tells you, "We should have bought that!"

45 Toll Gate Rd, Glastonbury

$599,999

Welcome to 712 Main Street, an exceptional historic residence in South Glastonbury, thoughtfully restored from top to bottom while preserving the timeless character and craftsmanship that make antique homes truly special. This remarkable home offers 4 bedrooms, including a stunning primary suite featuring new carpeting, a private en-suite bathroom, and an additional bonus room perfect for a home office, nursery, sitting area, or dressing room. A second bedroom also features its own en-suite bathroom, offering comfort and privacy for family or guests. Original hardwood floors throughout the home showcase the beauty and character of this historic property. The beautifully renovated kitchen features brand-new high-end appliances. A formal dining room, three fireplaces, and a conveniently located first-floor laundry room blend historic charm with modern functionality. A full bathroom on the main level adds convenience for everyday living and entertaining. No detail was overlooked in this extensive renovation. Updates include a new roof, siding, plumbing, electrical, heating system, and energy-efficient windows. All renovations were completed with proper permits and have passed inspections, providing peace of mind for years to come. Outside, enjoy a detached two-car garage with loft space for storage or a workshop, along with a separate shed. A rare opportunity to own a piece of South Glastonbury history with the comfort, efficiency, and elegance of a fully modernized home.

4 Beds ⋅ 4 Baths ⋅ 24192958 MLS

Welcome to 712 Main Street, an exceptional historic residence in South Glastonbury, thoughtfully restored from top to bottom while preserving the timeless character and craftsmanship that make antique homes truly special. This remarkable home offers 4 bedrooms, including a stunning primary suite featuring new carpeting, a private en-suite bathroom, and an additional bonus room perfect for a home office, nursery, sitting area, or dressing room. A second bedroom also features its own en-suite bathroom, offering comfort and privacy for family or guests. Original hardwood floors throughout the home showcase the beauty and character of this historic property. The beautifully renovated kitchen features brand-new high-end appliances. A formal dining room, three fireplaces, and a conveniently located first-floor laundry room blend historic charm with modern functionality. A full bathroom on the main level adds convenience for everyday living and entertaining. No detail was overlooked in this extensive renovation. Updates include a new roof, siding, plumbing, electrical, heating system, and energy-efficient windows. All renovations were completed with proper permits and have passed inspections, providing peace of mind for years to come. Outside, enjoy a detached two-car garage with loft space for storage or a workshop, along with a separate shed. A rare opportunity to own a piece of South Glastonbury history with the comfort, efficiency, and elegance of a fully modernized home.

712 Main St, Glastonbury

$554,000

South Glastonbury STUNNER! 90 S Mill is a true standout, where every inch has been thoughtfully designed, beautifully maintained, and finished with an exceptional attention to detail. From the moment you enter, the combination of style, quality, and effortless livability is apparent. The main living level features beautiful hardwood floors throughout and an open layout. The full updated kitchen opens seamlessly to the spacious dining and living areas, with smart storage, a large island, and gas cooking. The living room features soaring ceilings, beautiful windows, a gas fireplace, and a slider leading to an expansive deck overlooking a peaceful, wooded setting. The primary bedroom offers generous double closets and a beautifully remodeled full bath, while a second bedroom, second remodeled full bath and conveniently located laundry complete the main level. A spacious loft with skylights adds a versatile living area, perfect for a family room, office, play space, or quiet retreat. The lower level is an extraordinary extension of the home with over 900 square feet of finished, highly usable space. Three rooms, a full bath, multiple closets, a cedar closet, and plenty of natural light make this level exceptionally flexible. One room opens to the outdoors via sliders, while another features two full-size above-grade windows overlooking the surrounding landscape.

2 Beds ⋅ 3 Baths ⋅ 24198974 MLS ⋅ South Mill Village BLDG.

South Glastonbury STUNNER! 90 S Mill is a true standout, where every inch has been thoughtfully designed, beautifully maintained, and finished with an exceptional attention to detail. From the moment you enter, the combination of style, quality, and effortless livability is apparent. The main living level features beautiful hardwood floors throughout and an open layout. The full updated kitchen opens seamlessly to the spacious dining and living areas, with smart storage, a large island, and gas cooking. The living room features soaring ceilings, beautiful windows, a gas fireplace, and a slider leading to an expansive deck overlooking a peaceful, wooded setting. The primary bedroom offers generous double closets and a beautifully remodeled full bath, while a second bedroom, second remodeled full bath and conveniently located laundry complete the main level. A spacious loft with skylights adds a versatile living area, perfect for a family room, office, play space, or quiet retreat. The lower level is an extraordinary extension of the home with over 900 square feet of finished, highly usable space. Three rooms, a full bath, multiple closets, a cedar closet, and plenty of natural light make this level exceptionally flexible. One room opens to the outdoors via sliders, while another features two full-size above-grade windows overlooking the surrounding landscape.

90 S Mill Dr Unit 90, Glastonbury

$399,900

A Big Hug! Bring it in for this adorable, renovated Cape. Light streams from generous windows throughout, highlighting wide plank floors and immaculate upkeep. The kitchen and casual dining area feature 3 sides of multiple windows with views of the countryside below. Beautifully sited on a knoll, it highlights the rolling hills, and stone walls below. The home lives "larger" than its square footage thanks to a generous wooden porch which opens to the great room and kitchen. The kitchen, anchored by a handsome 8' granite island cooktop, is complemented by inset custom cabinetry. The adjacent dining room comfortably accommodates a 10' dining room table. The great room, warmed by a charming fireplace, is a generous and welcoming space. Upstairs two well-sized attractive bedrooms share an updated bath. The unfinished lower level has a slider and full size windows to the back of the property which floods with sunshine. This space could be customized for additional living space. A detached 2 car garage has room for gardening tools and sports equipment. This charmer is close to town and top schools with easy access to major highways. The entrance to Cotton Hollow/Roaring Brook is across the street for those nature lovers. Lean into the love.

2 Beds ⋅ 2 Baths ⋅ 24209530 MLS

A Big Hug! Bring it in for this adorable, renovated Cape. Light streams from generous windows throughout, highlighting wide plank floors and immaculate upkeep. The kitchen and casual dining area feature 3 sides of multiple windows with views of the countryside below. Beautifully sited on a knoll, it highlights the rolling hills, and stone walls below. The home lives "larger" than its square footage thanks to a generous wooden porch which opens to the great room and kitchen. The kitchen, anchored by a handsome 8' granite island cooktop, is complemented by inset custom cabinetry. The adjacent dining room comfortably accommodates a 10' dining room table. The great room, warmed by a charming fireplace, is a generous and welcoming space. Upstairs two well-sized attractive bedrooms share an updated bath. The unfinished lower level has a slider and full size windows to the back of the property which floods with sunshine. This space could be customized for additional living space. A detached 2 car garage has room for gardening tools and sports equipment. This charmer is close to town and top schools with easy access to major highways. The entrance to Cotton Hollow/Roaring Brook is across the street for those nature lovers. Lean into the love.

534 Hopewell Rd, Glastonbury

$399,900

Looking for easy living? This beautifully updated and meticulously maintained home may be just what you've been waiting for! Set on 2.70 private acres in the desirable Hopewell School District, this charming property offers a peaceful setting with plenty of room to relax and enjoy the outdoors. Sit on the welcoming front benches behind the classic white fence and enjoy what the world has to offer or explore the spacious private grounds. The home has undergone numerous updates since 2025, including an updated lower-level bathroom, a new kitchen backsplash, granite countertops and most windows replaced within the last year. A complete list of recent improvements is available for review. One of the standout features is the fully paid-off solar panel system, eliminating the monthly solar lease payment and potentially providing significant savings on electricity costs. The lower level also features a second bedroom and full bathroom, providing additional living space and flexibility for guests, a home office, or extended family. With its peaceful setting, extensive recent updates, solar savings, and generous acreage, this home offers a wonderful combination of comfort, privacy, and convenience.

2 Beds ⋅ 2 Baths ⋅ 24200054 MLS

Looking for easy living? This beautifully updated and meticulously maintained home may be just what you've been waiting for! Set on 2.70 private acres in the desirable Hopewell School District, this charming property offers a peaceful setting with plenty of room to relax and enjoy the outdoors. Sit on the welcoming front benches behind the classic white fence and enjoy what the world has to offer or explore the spacious private grounds. The home has undergone numerous updates since 2025, including an updated lower-level bathroom, a new kitchen backsplash, granite countertops and most windows replaced within the last year. A complete list of recent improvements is available for review. One of the standout features is the fully paid-off solar panel system, eliminating the monthly solar lease payment and potentially providing significant savings on electricity costs. The lower level also features a second bedroom and full bathroom, providing additional living space and flexibility for guests, a home office, or extended family. With its peaceful setting, extensive recent updates, solar savings, and generous acreage, this home offers a wonderful combination of comfort, privacy, and convenience.

931 Chestnut Hill Rd, Glastonbury

$389,000

This Classic American Farmhouse is located in the hills of South Glastonbury just a minutes from orchards, wineries and farms. The 1,105sq.ft. home is heated ( propane) and cooled by a new HVAC system. The interior has 3 bedrooms upstairs, an updated kitchen and bathroom, a cozy living room with gas fireplace, a sun room and dinning area that opens up to a new deck. The exterior has new siding, updated windows and a new basement bulkhead door. The house sits on a.8-acre lot at the end of a semi-private cul-de-sac.The lot is split by the driveway/road which the town plows and maintains.Outside is where this property really sets itself apart. Enjoy morning coffee on the new deck, evenings around the circular paver patio and fire pit,or simply take in the privacy of the surrounding woods and the properties meadow with the sound of Roaring Brook Nearby. Move-in ready and perfectly situated for anyone looking for an escape from a long day.

3 Beds ⋅ 1 Baths ⋅ 24199986 MLS

This Classic American Farmhouse is located in the hills of South Glastonbury just a minutes from orchards, wineries and farms. The 1,105sq.ft. home is heated ( propane) and cooled by a new HVAC system. The interior has 3 bedrooms upstairs, an updated kitchen and bathroom, a cozy living room with gas fireplace, a sun room and dinning area that opens up to a new deck. The exterior has new siding, updated windows and a new basement bulkhead door. The house sits on a.8-acre lot at the end of a semi-private cul-de-sac.The lot is split by the driveway/road which the town plows and maintains.Outside is where this property really sets itself apart. Enjoy morning coffee on the new deck, evenings around the circular paver patio and fire pit,or simply take in the privacy of the surrounding woods and the properties meadow with the sound of Roaring Brook Nearby. Move-in ready and perfectly situated for anyone looking for an escape from a long day.

77 Hopewell Hts, Glastonbury

$349,900

Brand New Roof & Skylight & A Brand New Price!! Charming New England-style farmhouse in desirable South Glastonbury! This 2-bed, 2-bath Colonial perfectly blends historic character with modern updates. Inside, you will find exposed beams, wide-plank wood flooring, recessed lighting, and skylights that fill the home with natural light. The spacious living room offers a warm, inviting space to relax, while the kitchen features updated appliances and flows effortlessly into the dining area and breakfast nook-an ideal layout for entertaining. The primary suite includes a private bath. The second bedroom is bright and comfortable, perfect for guests or a home office. Outside, you will find a private large, level yard and the sunny deck are made for outdoor gatherings. The mature landscaping is a gardener's dream. Highlighting sustainable hugelkultur gardens and an abundant variety of fruits, and flowers and trees, including apple, peach, cherry, fig, persimmon, and various berries alongside native perennials. Minutes from popular South Glastonbury restaurants and shops, Cotton Hollow and trails. While town records list the homes age as 1989 (renovation year) The Home is believed to date back to the mid-1800s. There are updated windows. New in 2022: well, dry well, water treatment/softener system, hot water heater, washer, dryer, refrigerator, dishwasher, and barnyard shed. Additionally there is an outdoor shed with power for home office. Come see it Today!

2 Beds ⋅ 2 Baths ⋅ 24204032 MLS

Brand New Roof & Skylight & A Brand New Price!! Charming New England-style farmhouse in desirable South Glastonbury! This 2-bed, 2-bath Colonial perfectly blends historic character with modern updates. Inside, you will find exposed beams, wide-plank wood flooring, recessed lighting, and skylights that fill the home with natural light. The spacious living room offers a warm, inviting space to relax, while the kitchen features updated appliances and flows effortlessly into the dining area and breakfast nook-an ideal layout for entertaining. The primary suite includes a private bath. The second bedroom is bright and comfortable, perfect for guests or a home office. Outside, you will find a private large, level yard and the sunny deck are made for outdoor gatherings. The mature landscaping is a gardener's dream. Highlighting sustainable hugelkultur gardens and an abundant variety of fruits, and flowers and trees, including apple, peach, cherry, fig, persimmon, and various berries alongside native perennials. Minutes from popular South Glastonbury restaurants and shops, Cotton Hollow and trails. While town records list the homes age as 1989 (renovation year) The Home is believed to date back to the mid-1800s. There are updated windows. New in 2022: well, dry well, water treatment/softener system, hot water heater, washer, dryer, refrigerator, dishwasher, and barnyard shed. Additionally there is an outdoor shed with power for home office. Come see it Today!

917 Hopewell Rd, Glastonbury