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Cheshire Homes for Sale

Newest Norfolk, CT Homes For Sale

$2,950,000
10 Beds ⋅ 9 Baths ⋅ 24199298 MLS
There are houses that have history, and houses in which history remains remarkably present. Set on six acres in the storied Litchfield County village of Norfolk, 16-18 Laurel Way is an exceptional country estate designed by Alfredo S.G. Taylor, the architect whose distinctive work is woven into the architectural identity of this quietly sophisticated corner of Connecticut. From the moment of arrival, the house reveals an extraordinary level of detail. The front entrance, framed by beautiful leaded-glass sidelights, sets the tone for interiors rich in craftsmanship, proportion, and character. Across an expansive 22 rooms, original architectural elements unfold one after another-handsome millwork, beautifully considered transitions between rooms, intimate corners, and grander spaces designed for gathering. Four fireplaces anchor the interiors, lending warmth and a sense of permanence to a house that feels both substantial and deeply personal. The scale is impressive, but it is the detail that gives the house its soul. Taylor's architecture was rooted in a sensitivity to place, and here the relationship between house and landscape feels particularly complete. Windows frame views of the grounds and gardens, while rooms open naturally toward the outdoors, creating the easy rhythm of a great New England country house. Beyond the main residence, six acres of mature grounds create a private world of lawns, established gardens, and quiet outdoor rooms.

16-18 Laurel Way, Norfolk
$549,000
4 Beds ⋅ 3 Baths ⋅ 24202134 MLS
Set on 2.8 acres overlooking Hall Meadow Brook, this 4-bedroom, 3-bathroom home offers exceptional single-level living with plenty of room to grow in a desirable Litchfield County setting. The open-concept living area features a wood-burning stove and a sunny bay window, creating a warm and inviting gathering space. The spacious dining area flows seamlessly into the kitchen and provides direct access to the patio, making indoor-outdoor entertaining effortless. The tastefully remodeled kitchen is equipped with stainless steel appliances, generous counter space, and abundant storage. The primary suite includes a walk-in closet and an updated bathroom featuring a jacuzzi-style tub and oversized shower. Three additional bedrooms and a full bathroom complete the main level. Downstairs, the partially finished basement offers flexible living space ideal for a cozy den, recreation room, home office, or gym, along with an adjoining full bathroom. A detached two-car garage with a finished attic provides even more potential for expansion, hobbies, or workspace. Outside, the back patio, complete with a dining area and hot tub, is perfectly suited for year-round entertaining. The covered front porch overlooks the open lawn and Hall Meadow Brook as it meanders through the property. Move-in ready yet offering ample opportunity to personalize and expand, this Norfolk property combines comfort, versatility, and the charm of Litchfield County living.

1226 Litchfield Rd, Norfolk
$279,000
4 Beds ⋅ 1 Baths ⋅ 24199835 MLS
Step into the character and charm of this classic farmhouse-style Colonial at 117 Greenwoods Road E in Norfolk, where timeless details meet an exciting opportunity to complete the home's transformation and make it your own. Set on a .62-acre lot, this 4 bedroom, 1 bath home offers high ceilings, hardwood flooring throughout much of the home, generous room sizes, and the kind of character that is hard to recreate. Renovations have already been started, with substantial improvements completed along the way, including the removal of the home's original plaster and installation of drywall, removal of knob-and-tube wiring, an updated 200-amp electrical panel, mineral wool insulation, foundation patching, and the addition of a new glulam beam with concrete-filled steel columns and footings. More recent improvements include exterior paint in 2022 and a new roof in 2023. The spacious kitchen offers plenty of room to create a gathering space that fits your vision and features an updated kitchen floor along with a gas line for the oven. Just beyond, the living room is anchored by a fireplace with a propane insert, with a new propane tank and gas line installed in 2023, creating a cozy centerpiece for the home. The large dining area, beautiful hardwood floors, and tall ceilings continue the home's classic farmhouse feel, while 4 bedrooms provide plenty of flexibility.

117 Greenwoods Rd E, Norfolk
$625,000
4 Beds ⋅ 3 Baths ⋅ 24200250 MLS
This very pretty village Victorian with lovely gardens was built in 1900 and has been well-cared for over the years. Many original features include cut glass and stained-glass windows, a full-width front porch with original fieldstone foundation, original fir and pine floors and 2 fireplaces.

58 Maple Ave, Norfolk
$620,000
4 Beds ⋅ 2 Baths ⋅ 24198002 MLS
Welcome to this beautiful 4-bedroom Colonial, privately situated on 9.16 acres, offering the perfect blend of space, character, and peaceful country living. Inside, you'll find a spacious kitchen with plenty of room for gathering and entertaining, while striking exposed wood-beam ceilings with warm wood-plank accents add incredible character and charm to the home. One of the highlights is the beautiful sunroom, an inviting space to relax, enjoy your morning coffee, or simply take in the peaceful surroundings year-round. Outside, the expansive acreage offers an incredible sense of privacy and tranquility, with plenty of room to enjoy the outdoors. A detached three-car garage provides generous space for vehicles, storage, hobbies, or a workshop. With four bedrooms, abundant living space, over nine acres, and a setting that feels tucked away from it all, this property is a wonderful opportunity to enjoy private country living with room to make it your own. Many thoughtful upgrades- NEW SEPTIC, NEW WASHER AND DRYER, NEW MICROWAVE, NEW SHOWERS, UPGRADED ELECTRICAL SYSTEM, NEW PAINT THROUGHOUT THE HOME, NEW PROPANE SYSTEM.

70 Colebrook Rd, Norfolk
$499,000
5 Beds ⋅ 3 Baths ⋅ 24193456 MLS
A piece of Norfolk's founding history is ready for its next steward. The Josiah Pettibone Tavern - home of Revolutionary War Colonel Giles Pettibone and birthplace of Ozark explorer Levi Pettibone - offers 3,523 sq ft of authentic antique Colonial on 1.01 level acres in the heart of Norfolk village. Six brick fireplaces, original stagecoach door, beamed ceilings, and a state-champion black locust standing watch since the 1800s. Legally configured as a two-family with two kitchens - a grandfathered use no longer available without Special Permit in this zone - live in the main house while the second unit offsets your costs, or restore it as a grand single residence. Town sewer at the street, documented survey, walkable to the village green and Infinity Hall. Offered as-is: this is a renovation project, bring your vision! Homes with this provenance, location, and flexibility do not repeat!!

10 North St, Norfolk
$499,000
5 Beds ⋅ 3 Baths ⋅ 24193303 MLS
A piece of Norfolk's founding history is ready for its next steward. The Josiah Pettibone Tavern - home of Revolutionary War Colonel Giles Pettibone and birthplace of Ozark explorer Levi Pettibone - offers 3,523 sq ft of authentic antique Colonial on 1.01 level acres in the heart of Norfolk village. Eight brick fireplaces, original stagecoach door, beamed ceilings, and a state-champion black locust standing watch since the 1800s. Legally configured as a two-family with two kitchens - a grandfathered use no longer available without Special Permit in this zone - live in the main house while the second unit offsets your costs, or restore it as a grand single residence. Town sewer at the street, documented survey, walkable to the village green and Infinity Hall. Offered as-is: this is a renovation project, bring your vision! Homes with this provenance, location, and flexibility do not repeat!!

10 North St, Norfolk
$4,200,000
6 Beds ⋅ 8 Baths ⋅ 24192442 MLS
Nestled within the absolute privacy of the 1,700-acre Doolittle Lake Company woods, this beautifully maintained 100-acre estate across two parcels features a magnificent 5,670-square-foot 1780 Center Hall Colonial blending colonial and Art Deco charm. Painstakingly relocated in the 1930s by architect Robert Carrere, the home boasts grand reception rooms with wide red pine floors, two wet bars, and nine wood-burning fireplaces. Authentic 1930s nostalgia is preserved through functioning rotary dial phones and butler bells, while the gourmet kitchen is updated with a fireplace, custom cabinetry with antique glass, and a unique trout-cleaning fish sink on the back porch. The main floor opens to stone-walled perennial gardens and a custom, heated oval gunite pool, complete with a dramatic arched pool house featuring kitchenette, half bath, dressing rooms, and an outdoor shower. Upstairs, the primary suite offers a private sitting area, fireplace, and steam shower alongside three large ensuite bedrooms with fireplaces, and a playroom. A private ensuite studio bedroom sits above the heated three-car garage, offering perfect accommodations for staff or guests.

210 Doolittle Dr, Norfolk
$799,000
2 Beds ⋅ 3 Baths ⋅ 24189465 MLS
Formerly known as Breezy Hill Farm, this exceptional 12.38-acre property lives up to its name, offering peaceful surroundings and refreshing breezes year-round. Set on two parcels, the beautifully renovated post-and-beam home seamlessly blends historic character with modern amenities. Completed in 2017, the extensive renovation included all new electrical, plumbing, spray foam insulation, flooring, kitchen, and bathrooms. The heart of the home is the spacious kitchen and dining area, featuring a large island with prep sink, granite countertops, gas cooktop, double wall ovens, and a woodstove set on a striking granite curbstone hearth. A sliding door opens to the expansive deck overlooking the beautifully landscaped, solar-heated in-ground pool. The inviting living room showcases original barn beams, preserving the property's rich history, while a bright foyer and convenient powder room complete the main level. An unfinished walkout room overlooking the pool offers endless possibilities as a family room, studio, fitness space, or recreation room. Upstairs, the primary suite offers vaulted ceilings with exposed beams, a generous walk-in closet, and a beautifully appointed bath with a walk-in shower and skylight. A second bedroom includes its own full bath, and a third bedroom provides flexible space for guests or a home office. Equestrian enthusiasts will appreciate the barn with four horse stalls, an indoor animal space, and a large garage with two overhead doors.

394 Winchester Rd, Norfolk
$749,000
3 Beds ⋅ 4 Baths ⋅ 24188179 MLS
Down a long private drive, this light-filled, artisan-built Cape blends over 5 acres of meadow and woods with Haystack Mountain views into a rare setting-complete privacy and close to town, summer music concerts, and the local swimming hole. Native cherry hardwood floors, solid wood doors, and wood trim run throughout. A central chimney anchors two fireplaces, while the main-floor primary suite allows for easy one-level living. Efficient mini-split heating and cooling provide year-round comfort, with a furnace for the coldest winter days. The upper level offers two bedrooms, a full bath, abundant storage, and an unfinished skylit room with potential for a studio, office, or additional living space. A mostly finished, dry walkout basement adds valuable living space with a recreation room, full bath, and French doors leading outdoors. Another room offers numerous possibilities. Featuring a 2021 roof and an oversized Western red cedar deck completed in 2024, this well-maintained home is move-in ready.

129 Sunset Ridge Rd, Norfolk
$599,000
4 Beds ⋅ 4 Baths ⋅ 24184788 MLS
Situated on 2.6 peaceful acres, this unique property offers exceptional space and flexibility for multigenerational living, rental potential, or a private guest residence. Offering 5 bedrooms, 3 full baths, and 1 half bath. The main residence features 3 bedrooms and 2 full baths, with the primary living quarters located above the oversized garage. This spacious upper level offers an open-concept living room, kitchen with dining area, the master bedroom has a walk-in closet and private bath, two additional bedrooms, a second full bath, and a private deck overlooking the peaceful surroundings. The in-law suite provides its own private living space with 2 bedrooms, 1.5 baths, spacious living room, dining room, kitchen, laundry room. Whether used for extended family, guests, or a private home office, this flexible layout offers endless possibilities. Car enthusiasts, hobbyists, and contractors will appreciate the impressive 40' x 40' heated garage, featuring radiant floor heat, a 12,000-pound two-post automotive lift, and abundant space for vehicles, equipment, or workshop projects. Additional year-round comfort is provided by a pellet stove and an energy-efficient mini-split system for supplemental heating and cooling. Minutes from the village center, hiking and biking trails, state parks, skiing, and dining.

155 Winchester Rd, Norfolk
$1,700,000
4 Beds ⋅ 3 Baths ⋅ 24188553 MLS
55 Golf Drive, Norfolk, CT 06058. Handsome 1935 Craftsman-style house on 2.79 acres surrounded by quiet, private land. The layout is gracious, and the rooms are spacious. There are 3,681 square feet of living area, a large living room with central fireplace, an equally large screened porch with stone pillars off the living room, a dining room/library room with secret office, a renovated kitchen, a main bedroom suite on the first floor and 3 additional bedrooms plus 2 additional full baths, The sunny stone terrace is gently surrounded by flower garden beds. Updates complement the style of the house. The house is being offered furnished for $1,700,000 except for seller's art and personal items.

55 Golf Dr, Norfolk
$6,650,000
6 Beds ⋅ 6 Baths ⋅ 24186864 MLS
Known as "The Bungalow", this spectacular Tudor-inspired estate set on 43.8 private acres is one of architect Alfredo S.G. Taylor's finest designs. Built in 1908 for a Remington Arms heiress, the home seamlessly blends Gilded Age grandeur with exceptional modern luxury. The dramatic great hall features soaring 40-foot timber ceilings, a monumental stone fireplace, and exquisite fieldstone and half-timber construction. Thoughtfully updated throughout, the home offers a stunning new eat-in chef's kitchen complete with a butler's pantry and premium appliances, including a True glass-door refrigerator, Miele dishwasher, Wolf warming drawers, Sub-Zero wine and beverage refrigerator, and an exceptional custom range with handcrafted hood. The luxurious marble-clad bathrooms have been beautifully renovated with Kohler fixtures, while custom cabinetry, updated electrical systems, and meticulous craftsmanship elevate every space. Spectacular balconies and a wraparound veranda extend from the main living areas, providing breathtaking views across the surrounding landscape. Offering 6 bedrooms, 6 bathrooms, and 6,766 square feet of living space, the estate is set amid lightly wooded grounds with expansive northern vistas. Additional amenities include a guest house, barn, formal gardens, and a picturesque pond. Approached by a winding, newly improved drive, the residence sits atop a private ridge and culminates in a gracious porte-cochere, creating a sense of arrival rarely found.

310 Litchfield Rd, Norfolk
$7,250,000
5 Beds ⋅ 5 Baths ⋅ 24177235 MLS
Introducing: Katsura. It might surprise you to learn that the ultimate lake wilderness retreat you've been searching for in Maine, Vermont, or Montana is actually hidden right here in the foothills of Connecticut. Perfectly positioned just over two hours from NYC, Katsura Lodge is a masterclass in privacy, offering a rare opportunity to truly escape into nature. Set at the end of a gated, long private crushed stone driveway, this 118-acre unspoiled woodland sanctuary offers approximately a mile of pristine frontage on Winchester Lake. It is the ultimate luxury camp. A place to unplug, exhale, and reconnect with family and friends. Offering over 5,000 square feet of sophisticated living space, this custom built, 5 bedroom contemporary residence integrates beautifully with its surroundings. Exceptional craftsmanship including heart pine and stone floors, custom cherry cabinetry, and soaring cathedral ceilings creates an elevated, warm aesthetic. In the great room, an impressive double-height fireplace, crafted from stones sourced directly from the property, anchors the space, while a cozy windowed reading nook invites quiet afternoons. Seemingly endless Albertini sliding glass doors erase the line between indoors and out, framing captivating views of the manicured grounds and the water. The home is designed for seamless entertaining on any scale. A gourmet chef's kitchen features top-of-the-line appliances, an adjoining wet bar, and a spacious wine cellar.

841 Winchester Rd, Norfolk
$595,000
5 Beds ⋅ 2 Baths ⋅ 24172329 MLS
Historic Norfolk Village Home on 3.4 Acres Classic Litchfield County setting defines this 3.4-acre property at the edge of Norfolk village. Lovingly held within the same family for generations, this captivating 1907 antique home sits on flat, open land with a classic large country barn, hay fields, and a spring-fed seasonal brook. The charming five-bedroom, two-bath residence retains its finest period details: welcoming front and side porches, original wood trim, stained glass windows, and hardwood floors. The full two-story layout features 9.5-foot ceilings and generous room proportions on the first floor, various sized bedrooms on the second, a walk-up attic above, and a full basement below. Sun-filled and tranquil, this home awaits your vision - whether renovation or preservation, the bones are excellent. Nestled in a lovely neighborhood and only minutes away from Norfolk's coveted amenities, this offering is a rare opportunity.

31 Sunset Ridge Rd, Norfolk
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