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Perched high above the South Glastonbury countryside, this extraordinary retreat offers breathtaking sunsets, sweeping views across rolling orchards to the Hartford skyline, and a sense of peace that is truly unforgettable. Two parcels, two residences, one extraordinary lifestyle. This is a home that simply cannot be fully captured in words or photographs-it must be experienced in person. From the breathtaking views and unforgettable sunsets to the thoughtful spaces, unique amenities, and peaceful surroundings, every corner reveals something special. It's more than a home; it's a lifestyle waiting to be felt. Cherished by one family and offered for the very first time, the property includes 2 parcels: 571 Woodland St, featuring the residence on approximately 1 acre, and 541 Woodland St, an additional approximately 1-acre lot. Walls of glass, soaring ceilings & private balconies bring the spectacular setting indoors. The main residence offers 4 bedrooms, 2 full baths, an open floor plan, private sauna & attached 3-car garage. The attached guest residence has its own living area, kitchen, dining space, laundry, fireplace, loft, 1 bedroom, 2 full baths & private balcony-ideal for multigenerational living, guests or a private retreat, with potential for yearly or short-term rental income, subject to applicable approvals, to help offset homeownership expenses.

5 Beds ⋅ 4 Baths ⋅ 24184457 MLS

Perched high above the South Glastonbury countryside, this extraordinary retreat offers breathtaking sunsets, sweeping views across rolling orchards to the Hartford skyline, and a sense of peace that is truly unforgettable. Two parcels, two residences, one extraordinary lifestyle. This is a home that simply cannot be fully captured in words or photographs-it must be experienced in person. From the breathtaking views and unforgettable sunsets to the thoughtful spaces, unique amenities, and peaceful surroundings, every corner reveals something special. It's more than a home; it's a lifestyle waiting to be felt. Cherished by one family and offered for the very first time, the property includes 2 parcels: 571 Woodland St, featuring the residence on approximately 1 acre, and 541 Woodland St, an additional approximately 1-acre lot. Walls of glass, soaring ceilings & private balconies bring the spectacular setting indoors. The main residence offers 4 bedrooms, 2 full baths, an open floor plan, private sauna & attached 3-car garage. The attached guest residence has its own living area, kitchen, dining space, laundry, fireplace, loft, 1 bedroom, 2 full baths & private balcony-ideal for multigenerational living, guests or a private retreat, with potential for yearly or short-term rental income, subject to applicable approvals, to help offset homeownership expenses.

571 Woodland St, Glastonbury

$650,000

Rare find!!! Authentic New England charm is preserved within this thoughtfully expanded 3,346 sq-ft (2,866 above grade) colonial-style home featuring additions and upgrades that provide modern conveniences and open spaces for today's lifestyle. Public utilities and solar too! The modern jewel, a stunning 2013 addition, adds a spectacular main-level primary suite with soaring ceilings, gleaming hardwood floors, abundant natural light, spacious walk-in closet, and a spa-inspired en-suite bath (clawfoot soaking tub and a walk-in steam shower). On the lower level of this addition you'll find two rooms, one with an impressive fireplace, separated by French doors for extra privacy. A large picture window overlooks the enchanting level back yard complete with babbling brook and hand crafted stone walls. Also on the main level is the beautifully updated kitchen, featuring granite countertops, large center island, soaring ceilings, ample dining space, and direct access to the rear patio for everyday enjoyment and easy outdoor entertaining. Adjacent is the formal dining room that showcases the second of this home's three fireplaces and serves as a beautiful reminder of the property's historic roots. Continuing on, you'll find wide plank original wooden floors, another fireplace, and the original wooden front door. A 1st floor office nook, an inviting four-season sunroom with walls of windows, plus a full bath with laundry round out this main level

4 Beds ⋅ 3 Baths ⋅ 24178336 MLS

Rare find!!! Authentic New England charm is preserved within this thoughtfully expanded 3,346 sq-ft (2,866 above grade) colonial-style home featuring additions and upgrades that provide modern conveniences and open spaces for today's lifestyle. Public utilities and solar too! The modern jewel, a stunning 2013 addition, adds a spectacular main-level primary suite with soaring ceilings, gleaming hardwood floors, abundant natural light, spacious walk-in closet, and a spa-inspired en-suite bath (clawfoot soaking tub and a walk-in steam shower). On the lower level of this addition you'll find two rooms, one with an impressive fireplace, separated by French doors for extra privacy. A large picture window overlooks the enchanting level back yard complete with babbling brook and hand crafted stone walls. Also on the main level is the beautifully updated kitchen, featuring granite countertops, large center island, soaring ceilings, ample dining space, and direct access to the rear patio for everyday enjoyment and easy outdoor entertaining. Adjacent is the formal dining room that showcases the second of this home's three fireplaces and serves as a beautiful reminder of the property's historic roots. Continuing on, you'll find wide plank original wooden floors, another fireplace, and the original wooden front door. A 1st floor office nook, an inviting four-season sunroom with walls of windows, plus a full bath with laundry round out this main level

539 Hopewell Rd, Glastonbury

$460,000

Nestled in the scenic hills of South Glastonbury, this charming 3-bedroom, 2-bath single-family home offers breathtaking views. Set on just under one acre, this picturesque lot along sought-after Matson Hill Road, this home is surrounded by rolling farmland, orchards and berry farms. Inside, enjoy a warm and inviting layout featuring a cozy fireplace, comfortable living spaces, and natural light throughout. The peaceful setting provides a true retreat while still being just minutes from Glastonbury center, local shops, dining, and top-rated schools. Whether relaxing by the fire or enjoying the tranquil outdoor surroundings, this property captures the charm and character of South Glastonbury living.

3 Beds ⋅ 2 Baths ⋅ 24157751 MLS

Nestled in the scenic hills of South Glastonbury, this charming 3-bedroom, 2-bath single-family home offers breathtaking views. Set on just under one acre, this picturesque lot along sought-after Matson Hill Road, this home is surrounded by rolling farmland, orchards and berry farms. Inside, enjoy a warm and inviting layout featuring a cozy fireplace, comfortable living spaces, and natural light throughout. The peaceful setting provides a true retreat while still being just minutes from Glastonbury center, local shops, dining, and top-rated schools. Whether relaxing by the fire or enjoying the tranquil outdoor surroundings, this property captures the charm and character of South Glastonbury living.

309 Matson Hill Rd, Glastonbury

$950,000

21.15 acres of land available in Glastonbury- see MLS #24175914 for additional information. Do not walk the property without permission from the listing agent.

24177960 MLS

21.15 acres of land available in Glastonbury- see MLS #24175914 for additional information. Do not walk the property without permission from the listing agent.

2501 Old Hebron Rd, Glastonbury

$950,000

Welcome to this private 21-acre parcel in Glastonbury featuring a charming early-1900s home surrounded by peaceful natural beauty. Rich with character and potential, the home offers an opportunity for thoughtful modernization and renovation to bring it to its full potential. Whether you're seeking a private estate setting with expansive acreage, an investment opportunity with two existing tenants in place, or exploring the future subdivision possibilities (subject to town approvals), this unique property offers exceptional versatility and value. Rarely does an opportunity like this become available in such a desirable location. Owner Financing Available. Please do not trespass.

5 Beds ⋅ 4 Baths ⋅ 24175914 MLS

Welcome to this private 21-acre parcel in Glastonbury featuring a charming early-1900s home surrounded by peaceful natural beauty. Rich with character and potential, the home offers an opportunity for thoughtful modernization and renovation to bring it to its full potential. Whether you're seeking a private estate setting with expansive acreage, an investment opportunity with two existing tenants in place, or exploring the future subdivision possibilities (subject to town approvals), this unique property offers exceptional versatility and value. Rarely does an opportunity like this become available in such a desirable location. Owner Financing Available. Please do not trespass.

2501 Old Hebron Rd, Glastonbury

$3,250,000

280-300 Matson Road presents a rare opportunity to acquire scenic agricultural- Rural Residential land in one of the most desirable areas of South Glastonbury. Currently operating as a spray-free berry farm and orchard, the property features gently rolling land, open fields, and sweeping views overlooking Hartford and the Connecticut River Valley. Adding to the long-term value and privacy of the setting, a neighboring farm is protected by a land trust, ensuring the surrounding landscape will remain preserved and free from future development. The property's natural beauty and expansive acreage create exceptional potential for a variety of future uses. The land is well suited for continued agricultural operations, a private family compound, or potential residential development. Its picturesque setting also lends itself to agritourism concepts such as a vineyard, brewery, farm store, farm bakery, or seasonal farmers market. With stunning views, protected neighboring farmland, and flexible possibilities, 280-300 Matson Road offers a unique opportunity to create a destination property while preserving the charm of Connecticut's agricultural landscape. Do not walk the property without permission

24161859 MLS

280-300 Matson Road presents a rare opportunity to acquire scenic agricultural- Rural Residential land in one of the most desirable areas of South Glastonbury. Currently operating as a spray-free berry farm and orchard, the property features gently rolling land, open fields, and sweeping views overlooking Hartford and the Connecticut River Valley. Adding to the long-term value and privacy of the setting, a neighboring farm is protected by a land trust, ensuring the surrounding landscape will remain preserved and free from future development. The property's natural beauty and expansive acreage create exceptional potential for a variety of future uses. The land is well suited for continued agricultural operations, a private family compound, or potential residential development. Its picturesque setting also lends itself to agritourism concepts such as a vineyard, brewery, farm store, farm bakery, or seasonal farmers market. With stunning views, protected neighboring farmland, and flexible possibilities, 280-300 Matson Road offers a unique opportunity to create a destination property while preserving the charm of Connecticut's agricultural landscape. Do not walk the property without permission

280-300 Matson Hill Rd, Glastonbury

$1,635,000

To Be Built- Exceptional New Construction in Crosby II Subdivision by Renowned Builder Reggie Jacques- known for decades of experience & for developing many of Glastonbury's most desirable neighborhoods. The proposed layout offers beautiful architecture, strong curb appeal, & a flexible floor plan designed for modern living. Main level features a dramatic two-story family room w/ a fireplace, custom built-ins, and a wall of windows that fills the space with natural light. Family room flows seamlessly into the kitchen, offering the opportunity to design your dream kitchen with endless possibilities. Formal living & dining rooms add elegance to the first floor, along with a bedroom and full bath that can easily serve as a study, office, or playroom. A convenient mudroom will also be added off the garage. Upstairs, the luxurious primary suite impresses with his-and-hers walk-in closets and a spacious bath featuring a tile shower and a soaking tub. Two additional bedrooms share a Jack-and-Jill bath, while a fourth bedroom includes its own private bath and walk-in closet. All bedrooms are generously sized. A convenient laundry room off the primary suite completes the second floor. The lot is currently being cleared and sits on 1.12 acres, offering a level yard and space for a large patio. Located in an extremely desirable neighborhood with limited availability, this is a rare opportunity to build your dream home in Crosby II.

5 Beds ⋅ 5 Baths ⋅ 24158783 MLS

To Be Built- Exceptional New Construction in Crosby II Subdivision by Renowned Builder Reggie Jacques- known for decades of experience & for developing many of Glastonbury's most desirable neighborhoods. The proposed layout offers beautiful architecture, strong curb appeal, & a flexible floor plan designed for modern living. Main level features a dramatic two-story family room w/ a fireplace, custom built-ins, and a wall of windows that fills the space with natural light. Family room flows seamlessly into the kitchen, offering the opportunity to design your dream kitchen with endless possibilities. Formal living & dining rooms add elegance to the first floor, along with a bedroom and full bath that can easily serve as a study, office, or playroom. A convenient mudroom will also be added off the garage. Upstairs, the luxurious primary suite impresses with his-and-hers walk-in closets and a spacious bath featuring a tile shower and a soaking tub. Two additional bedrooms share a Jack-and-Jill bath, while a fourth bedroom includes its own private bath and walk-in closet. All bedrooms are generously sized. A convenient laundry room off the primary suite completes the second floor. The lot is currently being cleared and sits on 1.12 acres, offering a level yard and space for a large patio. Located in an extremely desirable neighborhood with limited availability, this is a rare opportunity to build your dream home in Crosby II.

79 Crosby Rd, Glastonbury

$1,750,000

To Be Built - Exceptional Home in Prestigious Crosby II Subdivision by Renowned Builder Reggie Jacques. This stunning new construction will be crafted by one of Glastonbury's most respected builders known for his decades of experience and exceptional skill in developing many of Glastonbury's most desirable subdivisions. This future home will offer a sophisticated layout featuring an open-concept, soaring ceilings, highest grade level finishes, and 9' ceilings on every floor. Grand family room, flexible first-floor bedroom suite (ideal for guests or multigenerational living), and opportunity to design every detail in kitchen, baths... Luxurious primary suite, expansive rooms throughout and exceptional architectural details will create a truly impressive living experience. Buyers will have the opportunity to customize finishes and tailor the layout and overall design of the home to fit their lifestyle including the Kitchen- with many options available. Premier Lot-Set in the sought-after Crosby II neighborhood sitting on over 2 acres of land, this home will stand out for its luxury, curb appeal, and craftsmanship. Don't miss your chance to build your dream home in one of Glastonbury's finest communities.

5 Beds ⋅ 6 Baths ⋅ 24094237 MLS

To Be Built - Exceptional Home in Prestigious Crosby II Subdivision by Renowned Builder Reggie Jacques. This stunning new construction will be crafted by one of Glastonbury's most respected builders known for his decades of experience and exceptional skill in developing many of Glastonbury's most desirable subdivisions. This future home will offer a sophisticated layout featuring an open-concept, soaring ceilings, highest grade level finishes, and 9' ceilings on every floor. Grand family room, flexible first-floor bedroom suite (ideal for guests or multigenerational living), and opportunity to design every detail in kitchen, baths... Luxurious primary suite, expansive rooms throughout and exceptional architectural details will create a truly impressive living experience. Buyers will have the opportunity to customize finishes and tailor the layout and overall design of the home to fit their lifestyle including the Kitchen- with many options available. Premier Lot-Set in the sought-after Crosby II neighborhood sitting on over 2 acres of land, this home will stand out for its luxury, curb appeal, and craftsmanship. Don't miss your chance to build your dream home in one of Glastonbury's finest communities.

105 Crosby Rd, Glastonbury

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