Glastonbury 5 Bedroom Properties for Sale

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Newest Glastonbury 5 Bedroom Homes and Condos for Sale

$1,200,000

5 Beds ⋅ 5 Baths ⋅ 24216897 MLS

Experience timeless elegance and exceptional craftsmanship in this stunning, close to newly built, 5-bedroom, 4.5-bath home, blending luxurious finishes with modern functionality. A dramatic two-story foyer welcomes you to beautifully appointed interiors featuring coffered ceilings, a graceful barrel archway, oak floors, and exquisite custom millwork. Designed for everyday living and entertaining, the showstopping designer kitchen boasts premium appliances, elegant countertops, and an oversized eat-in dining area overlooking the living room, creating a seamless, open-concept gathering place. An entertainer's delight perfect for gatherings or a relaxed evening at home. A stylish mudroom with custom built-in bench seating adds convenience and organization, while a first-floor bedroom with a full bath offers flexibility for guests, multigenerational living, or even a home office. Upstairs, the luxurious primary suite provides a private retreat, complete with an impressive, oversized walk-in closet that offers the space and storage anyone would dream of. The walk-out basement presents endless possibilities for additional living space, a home gym, recreation area, or a potential media room. An in-ground sprinkler system adds convenience to outdoor maintenance. Combining classic sophistication with modern colonial design, this exceptional home offers upscale finishes, thoughtful details, and inviting spaces designed for comfortable living and effortless entertaining.

241 Old Farms Rd, Glastonbury

$950,000

5 Beds ⋅ 4 Baths ⋅ 24200253 MLS

Welcome to this exceptional 5-bedroom, 3.5-bath Colonial offering approximately 3,800 square feet of beautifully designed living space in one of South Glastonbury's most desirable neighborhoods. Perched high above the surrounding landscape, this home enjoys beautiful views of the Connecticut River and surrounding farmland. From the moment you enter, you'll appreciate the thoughtful design, spacious layout, and wonderful blend of comfort and elegance. The main level offers a wonderful balance of open-concept living spaces and thoughtfully designed rooms for both everyday living and entertaining. At the heart of the home, the spacious eat-in kitchen features custom cabinetry, granite countertops, a pantry, and a charming breakfast nook overlooking the surrounding farmland and Connecticut River. The kitchen flows seamlessly into the family room, where a beautiful brick fireplace creates a warm and welcoming gathering space, while the adjoining dining room and living room offer additional spaces for entertaining and relaxing. A dedicated home office provides the perfect work-from-home setting, and the private fifth bedroom with a full bath offers exceptional flexibility as a guest suite, au pair space, or first-floor bedroom.

513 Tryon St, Glastonbury

$1,399,999

5 Beds ⋅ 4 Baths ⋅ 24204242 MLS

Perched high above the South Glastonbury countryside, this extraordinary two-residence property offers a rare opportunity to combine luxury living with income potential. Sweeping orchard views, breathtaking sunsets and distant Hartford skyline views create an unforgettable setting with exceptional appeal for multigenerational living, luxury rentals or potential short-term rental use, subject to applicable approvals. Two parcels. Two residences. Multiple possibilities. The property includes 571 Woodland St, with the residences on approximately 1 acre, plus 541 Woodland St, an additional approximately 1-acre parcel. The main residence offers 4 bedrooms, 2 full baths, soaring ceilings, walls of glass, private balconies, sauna and attached 3-car garage. The private guest residence features 1 bedroom plus loft, 2 full baths, kitchen, living and dining areas, fireplace, laundry and private balcony. Ideal for an owner-occupant seeking supplemental income or an investor exploring luxury rental opportunities. A distinctive lifestyle property where privacy, flexibility and investment potential converge.

571 Woodland St, Glastonbury

$619,900

5 Beds ⋅ 4 Baths ⋅ 24203680 MLS

LOCATION ALERT!!! Incredible offering with 5 bedrooms, 3.1 baths and a deceptively spacious interior that delivers far more room than you might expect! Ideally located on a quiet neighborhood street with easy access to in-town shopping, restaurants, schools, commuter routes and downtown Hartford. SOLAR panels are not leased-see agent to agent remarks. Inside, the flexible floor plan includes two main-level bedrooms, perfect for guests, multigenerational living or a home office, while still offering spacious living areas throughout. Stunning family room with stone fireplace, vaulted ceilings and access to back patio. An updated kitchen features a smart refrigerator and dishwasher, touchless sensor faucet and propane cooking, complemented by WiFi-monitored oil and propane tank gauges for added convenience. Outside, a huge paver patio creates an expansive space for entertaining, dining and relaxing, overlooking a private backyard framed by mature trees. With 5 bedrooms, generous room sizes, modern updates, smart-home features and a surprisingly spacious layout, this home combines the space buyers want with a location that keeps everyday conveniences close by. Home warranty: upto Oct 2027 - transferable to new owner

25 Hampshire Dr, Glastonbury

$1,100,000

5 Beds ⋅ 3 Baths ⋅ 24205617 MLS

Unbelievable opportunity--first time offered in many decades! With 10 rolling acres, views of Hartford, 2 houses and 2 large commercial barns, this property (the original Berruti family farm) is waiting for your dreams! Imagine what you could do... Build your dream home? Develop a family compound? Own your own vineyard or orchard? Build an investment portfolio? Let your imagination run wild (subject to the town building and zoning regulations.

136 Chestnut Hill Rd, Glastonbury

$499,000

5 Beds ⋅ 3 Baths ⋅ 24206462 MLS

Welcome to this spacious 5-bedroom, 2.5-bath home in a highly sought-after Glastonbury location. With 2,186 square feet, this home offers plenty of space and flexibility, including three bedrooms, a full bath, an eat-in kitchen with a slider to access outside and laundry all on the first floor-ideal for those looking for the option of one-floor living.The main level also features a versatile rear den with a fireplace and separate exterior entrance, making it well suited for a home office, guest space, playroom, or additional living area. Upstairs, you'll find two generously sized bedrooms and a large full bath. Outside, enjoy an expansive deck overlooking a flat, fully fenced yard-perfect for entertaining and everyday outdoor living. Stellar location, public water and sewer, 1 car garage...book your showing today!

17 Sherman Rd, Glastonbury

$7,200,000

5 Beds ⋅ 8 Baths ⋅ 24191237 MLS

The wait is over-the Grand Dame of South Glastonbury is now available. Perched atop one of Connecticut's most breathtaking settings, this extraordinary custom French chateau commands sweeping views stretching to Massachusetts, along with spectacular sunsets over the Hartford skyline.A true labor of love, this remarkable estate reflects more than 13 years spent sourcing the finest materials and architectural inspirations from the grand estates of France and Newport, Rhode Island. Inside, every detail has been thoughtfully curated to capture the authenticity and elegance of a classic French chateau. Eight custom fireplaces imported from Europe, exquisite chandeliers inspired by Versailles, hand-crafted Habersham cabinetry, and premium Miele appliances define the stunning chef's kitchen. Each room offers its own distinct character, showcasing exceptional craftsmanship through intricate millwork, hand carved limestone fireplaces, Brazilian walnut and marble flooring, ornate medallions, solid mahogany doors, custom wrought iron, and a magnificent circular marble staircase. Step into a world of timeless elegance, where uncompromising quality and artistry are evident at every turn. Every room enjoys breathtaking views, from the spectacular primary suite to the attached guest house. Enter the primary retreat through its dramatic rotunda, leading to extraordinary custom closets, a luxurious spa bath, and a bedroom featuring a private balcony and a stunning marble-and-brass fireplace.

105 Crystal Ridge Rd, Glastonbury

$1,399,999

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

$950,000

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

$1,635,000

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

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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Glastonbury 5 Bedroom Properties for Sale

Newest Glastonbury 5 Bedroom Homes and Condos for Sale

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