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Homes for Sale near South Kent School

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  • /40

    $799,000

    • 4 Beds
    • 3.5 Baths
    • 2,511 Sq Ft

    165 Merryall Rd, New Milford, CT 06776

    Modern Farmhouse Retreat in Historic Merryall with exceptional River Frontage! Tucked away on almost 6 peaceful acres along the West Aspetuck River, this beautiful home has it all! Private trails, lower meadow and swimming hole...bring your kayaks! Thoughtfully designed and impeccably built using only the highest-quality materials, this property is a true haven in one of the area's most scenic

    Agent Photo

    Rebecca Doh

    W. Raveis Lifestyles Realty

    (860) 821-4619

    165 Merryall Rd, New Milford, CT 06776
  • /39

    $964,900

    • 4 Beds
    • 4.5 Baths
    • 4,848 Sq Ft

    427 Long Mountain Rd, New Milford, CT 06776

    Welcome to the desirable Merryall section of New Milford, one of the town's premier neighborhoods known for low taxes and expansive properties, and exceptional privacy. Just 15 min. to Metro-North and convenient to Kent, Sherman, and the scenic Litchfield Hills. Experience the perfect blend of peace and privacy while staying close to shops, dining, and everyday conveniences. This elegant

    Agent Photo

    Robert Leonard

    Berkshire Hathaway NE Prop.

    (860) 321-1043

    427 Long Mountain Rd, New Milford, CT 06776
  • /7

    $189,900

    • Land
    • 3.04 Acres
    • $62,467 per Acre

    34 Front of the Mountain Rd, New Milford, CT 06776

    34 Front of The Mountain Road in New Milford is a premier parcel where you can enjoy the tranquility of Litchfield County. Embrace the rare opportunity to a wow house or quiet cabin on scenic Front of The Mountain Road. This property offers a peaceful setting with stunning views, providing a perfect blend of natural beauty and New England charm. Situated in New Milford, Front of the Mountain Road

    Agent Photo

    Sharon Watson Stokland

    List N Show LLC

    (860) 237-3995

    34 Front of the Mountain Rd, New Milford, CT 06776
  • /40

    $825,000

    • 4 Beds
    • 4.5 Baths
    • 2,234 Sq Ft

    360 Old State Route 22, Dover Plains, NY 12522

    A rare offering in today’s market - gorgeous River Front Home with calming water views and fishing every day right in your own back yard. Renovated and updated 3 bedroom home with a one bedroom pool house that doubles as a guest cottage. All the amenities you would expect in the best resort style property. Open concept Living and Dining area with 2 sets of French doors opening to an expansive

    Judy Albert BHHS Hudson Valley Properties

    360 Old State Route 22, Dover Plains, NY 12522
  • /34

    $895,000

    • 6 Baths
    • 5,952 Sq Ft

    685 Kent Rd, Gaylordsville, CT 06755

    Church for sale! Available to be used as a new denomination, or converted to a residence. Beautiful sanctuary complete with pews with more in balcony. It has several large meeting/class rooms and an office, with two restrooms. Could be converted into a very cool house! There is also a 2931 sf 3BR antique rectory house on the property, part of which has been rented as a residence and part of

    Richard Pomerantz William Pitt Sotheby's Int'l

    685 Kent Rd, Gaylordsville, CT 06755
  • /25

    $1,049,000

    • 4 Beds
    • 3.5 Baths
    • 3,350 Sq Ft

    42 Long River Rd, Sherman, CT 06784

    Spend your summer in this beautiful, gated community playing golf on the signature 18-hole course, enjoying a game of tennis or swimming in the heated in ground pool. There is full-service club house complete with a pro shop, pub and restaurant. You can enjoy dining on the patio that overlooks the greens. Inquire about membership details. The home is ready for immediate occupancy, so come up and

    Cynthia Szentkuti Ridgefield Homes Realty

    42 Long River Rd, Sherman, CT 06784
  • /21

    $1,295,000

    • 2 Beds
    • 2 Baths
    • 1,933 Sq Ft

    39 Treasure Hill Rd, South Kent, CT 06785

    Dream retreat in South Kent on nearly 25 high acres with potential to create views of rolling hills to the west. Private and quiet on one of Kent's most prestigious and scenic roads, This quaint cottage style contemporary is nestled well off the road yet is only minutes to the vibrant New England Village of Kent and around the corner to Lake Waramaug for golf, tennis, swimming, hiking trails,

    Karen Casey William Pitt Sotheby's Int'l

    39 Treasure Hill Rd, South Kent, CT 06785
  • /37

    $840,000

    • 4 Beds
    • 4.5 Baths
    • 3,808 Sq Ft

    43 Gaylord Rd, Gaylordsville, CT 06755

    This historic 18th-century Gaylord family homestead in New Milford, Connecticut, offers a perfect blend of authentic period charm and thoughtful modern enhancements. Set on picturesque grounds at 43 Gaylord Road, this distinctive Litchfield County property features versatile living spaces including an open-concept kitchen, living room, inviting Sun Room, formal dining room, and a cozy Snuggery

    Liza Reiss Elyse Harney Real Estate

    43 Gaylord Rd, Gaylordsville, CT 06755
  • /39

    $1,685,000

    • 4 Beds
    • 4.5 Baths
    • 5,475 Sq Ft

    1 Cloverleaf Farm S, Sherman, CT 06784

    Experience the epitome of modern luxury in this expansive contemporary home with captivating long-range southerly VIEWS! This architectural masterpiece is designed with an open plan that seamlessly integrates living, dining and kitchen spaces, creating an environment perfect for sophisticated entertaining and comfortable daily living. Culinary adventures await in the state-of-the-art kitchen,

    Alan O'Doherty William Pitt Sotheby's Int'l

    1 Cloverleaf Farm S, Sherman, CT 06784
  • /37

    $1,500,000

    • 4 Beds
    • 3.5 Baths
    • 6,000 Sq Ft

    13 Cobble Heights Rd, Kent, CT 06757

    Nestled on 8 private acres with a pond, on a private road, this house is in the picturesque town of Kent, CT. The home has 10 rooms including 4 bedrooms, 3 full bathrooms and 2 half baths. A large guest wing with a separate entrance includes a sitting/living room, 1 bedroom and a full bathroom. There are 3 beautiful stone fireplaces that provide warmth and ambiance to the living room, kitchen and

    Janet Nelson William Pitt Sotheby's Int'l

    13 Cobble Heights Rd, Kent, CT 06757
  • /2

    $1,195,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,675 Sq Ft

    60 Long River Rd, Sherman, CT 06784

    River Oaks Golf Course New Construction!! Sherman's best value. New construction 4 bedroom 4.5 bath colonial with open floorplan and 2 primary bedrooms. (main level and upper) Propane heat and Central Air. Composite decking. 9 Ft ceilings on the main level. 3 car attached garage. Hardwood floors throughout. Center island kitchen with large pantry and granite/quartz counters. All bedrooms have

    Joe Chemero Coldwell Banker Realty

    60 Long River Rd, Sherman, CT 06784
  • /19

    $439,000

    • 2 Beds
    • 1.5 Baths
    • 1,252 Sq Ft

    80 N Main St Unit 5B5, Kent, CT 06757

    An exceptional opportunity in the heart of Kent's vibrant village center, just steps from shops and restaurants. This beautifully maintained two-bedroom Kent Hills condo has been thoughtfully updated with numerous recent improvements. The sun-filled kitchen is stylishly appointed and flows seamlessly into the open living and dining area, anchored by a handsome fireplace. Both spaces extend to a

    Steve Pener William Pitt Sotheby's Int'l

    80 N Main St Unit 5B5, Kent, CT 06757
  • /50

    $445,000

    • 3 Beds
    • 2 Baths
    • 2,072 Sq Ft

    26 Nicole Ln, Wingdale, NY 12594

    Charming and fully remodeled, this 3-bedroom, 2-bath raised ranch in the desirable Woodwinds subdivision offers modern comfort and timeless appeal. With a fully fenced yard, spacious deck, and detached oversized 2-car garage, this home is move-in ready and designed for easy living. Recent updates include a new roof (2022), new furnace (2024), new water softener system (2023), refreshed central

    Andrea Rudkowski Closer Real Estate

    26 Nicole Ln, Wingdale, NY 12594
  • /10

    $129,000

    • Land
    • 2.00 Acres
    • $64,500 per Acre

    28 Webatuck Rd, Gaylordsville, CT 06755

    Opportunity awaits to build your dream home on this exceptional 2-acre parcel featuring over 300 feet of private Wimisink Brook frontage. With some site work already completed-including curb cut, roughed-in driveway from 200 feet of road frontage, foundation excavation, deep and perc tests, and septic fields installed for a 4-bedroom home-you can start building sooner. The homesite sits high

    Dawn Grabover Keller Williams Realty

    28 Webatuck Rd, Gaylordsville, CT 06755
  • /10

    $400,000

    • 2 Beds
    • 2 Baths
    • 1,225 Sq Ft

    80 N Main St Unit 4A1, Kent, CT 06757

    Wonderful first floor, corner condo in downtown Kent. This unit comes with two separate garages right next to the unit with 2 extra parking spaces that no other unit has and creating very easy access to unit. North side looks out to pastures of butting properties. Exceptional setting.

    David Bain Bain Real Estate

    80 N Main St Unit 4A1, Kent, CT 06757
  • /18

    $290,000

    • 2 Beds
    • 1 Bath
    • 1,362 Sq Ft

    20 Hemlock Ln, Wingdale, NY 12594

    Welcome to this 2 bedroom raised ranch nestled on a quiet cul-de-sac. Offering a perfect blend of privacy and comfort, this home features a spacious, tree-lined yard-ideal for relaxing, entertaining, or gardening. Step out onto the cozy deck and enjoy your morning coffee. Inside, the layout offers functional living space with great natural light and potential to make it your own. The highlight of

    Crystal Neceda Briante Realty Group, LLC

    20 Hemlock Ln, Wingdale, NY 12594
  • /14

    $500,000

    • 3 Beds
    • 2 Baths
    • 1,818 Sq Ft

    41 Meetinghouse Terrace, New Milford, CT 06776

    Nestled in a serene and private neighborhood, this beautiful contemporary Cape-style home offers the perfect balance of peaceful living and convenience. Just minutes from downtown New Milford, you'll enjoy easy access to everything the area has to offer, including a golf course, health club, library, medical facilities, playgrounds, tennis courts, and more. Step inside to discover a spacious,

    Alex De Camargo eXp Realty

    41 Meetinghouse Terrace, New Milford, CT 06776
  • /22

    $279,000

    • Land
    • 5 Acres
    • $51,099 per Acre

    LOT 30 Long River Rd, Sherman, CT 06784

    This exceptional 5.46-acre parcel, perfectly positioned on Long River Road, is the largest homesite in the private community of River Oaks Country Club. The lightly wooded setting offers privacy and a natural backdrop for your custom residence with potential for sweeping long views that capture the beauty of the Berkshire foothills. Club River Oaks provides access to world-class amenities,

    Donna Kennedy Keller Williams Realty

    LOT 30 Long River Rd, Sherman, CT 06784
  • /25

    $630,000

    • 4 Beds
    • 2.5 Baths
    • 2,469 Sq Ft

    132 S Kent Rd, South Kent, CT 06785

    Don't miss this exceptional opportunity in desirable South Kent. This four-bedroom Colonial offers beautiful views and a spacious, light-filled layout. The main level features an inviting kitchen with an island, seamlessly connected to the living and dining room anchored by a cozy fireplace. Two sets of French doors lead to a sunroom addition, perfect for relaxing or entertaining. The main level

    Steve Pener William Pitt Sotheby's Int'l

    132 S Kent Rd, South Kent, CT 06785
  • /9

    $275,000

    • Land
    • 15 Acres
    • $17,776 per Acre

    0 Cricket Hill Rd, Wingdale, NY 12594

    This land is ready for you to fulfill your dreams. 15.47 acres in a pastoral setting. With multiple potential hilltop building sites, choose your view from awe inspiring western sunsets to eastern mountain views overlooking the Ten Mile River. There is plenty of room up top to build your country escape and fulfill your dreams, whether it is adding a barn for a small hobby farm, avid collector,

    Brian McGrath McGrath Realty Inc

    0 Cricket Hill Rd, Wingdale, NY 12594
  • /28

    $459,000

    • 1 Bed
    • 1.5 Baths
    • 3,660 Sq Ft

    696 Kent Rd, New Milford, CT 06755

    A Wonderful Opportunity To Own This Large Multi-Use Commercial And Residential Property! Located In The Hamlet of Gaylordsville In New Milford CT. Beautiful Location That Has Access To The Housatonic River. Located On Kent Road That Has Direct Access To N.Y. & Neighboring CT Towns. This Property Also Has A Beautiful Scenic View & Is Very Private. A Wonderful Combination Of Residential & Retail!

    Dennis Guido Coldwell Banker Realty

    696 Kent Rd, New Milford, CT 06755
  • /40

    $6,200,000

    • 4 Beds
    • 5 Baths
    • 6,236 Sq Ft

    57 Indian Trail Rd, New Milford, CT 06776

    Welcome to Hollow Farm,an ultra-private 77 acre estate nestled in the heart of Connecticut,where luxury meets history and modern amenities. This exceptional property is a testament to refined living, boasting a main residence that seamlessly blends historic charm with contemporary systems. As you step inside,you are greeted by original wood floors that lead you through a home warmed with radiant

    Pat Lahoud William Pitt Sotheby's Int'l

    57 Indian Trail Rd, New Milford, CT 06776
  • /38

    $499,000

    • 3 Beds
    • 2 Baths
    • 2,702 Sq Ft

    12 Webatuck Rd, Gaylordsville, CT 06755

    Discover the perfect blend of charm and functionality with this exceptional 10-room antique Colonial, ideally suited for horse lovers and nature enthusiasts. Set on picturesque grounds fronting both a brook and a river, the property features a barn, fenced paddocks, and direct access to dirt roads and riding trails-ideal for horseback riding, hiking, or ATV adventures. Inside, the home exudes

    Stephen Mele Houlihan Lawrence

    12 Webatuck Rd, Gaylordsville, CT 06755
  • /38

    $548,000

    • 2 Beds
    • 2 Baths
    • 1,425 Sq Ft

    10 Anderson Rd E, Sherman, CT 06784

    MOVE IN READY! Looking for a country retreat, weekend home, artist escape or a work from home space? This charming, ranch home set in a beautiful serene setting has your name on it. This home has great flow and allows the peaceful outside space in- you can feel this the minute you walk through the front door. The living room has almost a full wall of windows showcasing the private garden with

    Ginny Gordon-O’Neill William Raveis Real Estate

    10 Anderson Rd E, Sherman, CT 06784
  • /40

    $1,850,000

    • 4 Beds
    • 4.5 Baths
    • 3,790 Sq Ft

    168 Cobble Rd, Kent, CT 06757

    Welcome to 168 Cobble Rd! Better than new 4 bedroom custom colonial on 14.45 private acres with breathtaking mountain views. Enjoy your morning coffee and dramatic sunsets on your full length deck or private balcony. Open layout features chef's kitchen, soaring ceilings, beams, skylights, and lots of windows. The kitchen is fully equipped with Wolf gas range and Bosch refrigerator and dishwasher.

    Joe Chemero Coldwell Banker Realty

    168 Cobble Rd, Kent, CT 06757
  • /6

    $489,000

    • Land
    • 13 Acres
    • $36,303 per Acre

    430 Long Mountain Rd Unit LOT 3, New Milford, CT 06776

    Amazing opportunity to buy land or custom build in gated 4 lot community in the country with privacy, beautiful mountain views and each lot has the use of 10 acres of open space. Plus the neighborhood backs up to farmland and open space. Lot 3 is 13.47 acres and there is room for a pool/outbuilding. 3500 sq ft minimum home size and architectural review. Other lots to choose or owner can build to

    Joe Chemero Coldwell Banker Realty

    430 Long Mountain Rd Unit LOT 3, New Milford, CT 06776
  • /50

    $865,000

    • 4 Beds
    • 6 Baths
    • 4,788 Sq Ft

    211 Cricket Hill Rd, Dover Plains, NY 12522

    This is the one—an exceptional and truly special property offering the perfect blend of refined living, natural beauty, and flexibility. Set against a breathtaking countryside backdrop, this Colonial Farmhouse-style home is nestled on just over 5 private, picturesque acres—perfectly suited for horses, weekend escapes, or year-round living. With nearly 4,800 square feet of thoughtfully crafted

    Sherri Malone Coldwell Banker Realty

    211 Cricket Hill Rd, Dover Plains, NY 12522
  • /9

    $289,000

    • Land
    • 2.99 Acres
    • $96,559 per Acre

    430 Long Mountain Rd Unit LOT 1, New Milford, CT 06776

    Amazing opportunity to buy land or custom build in gated 4 lot community in the country with privacy, beautiful mountain views and each lot has the use of 10 acres of open space. Plus the neighborhood backs up to farmland and open space. Lot 1 is 3 acres and there is room for a pool. 3500 sq ft minimum home size and architectural review. Other lots to choose or owner can build to suit. (lots

    Joe Chemero Coldwell Banker Realty

    430 Long Mountain Rd Unit LOT 1, New Milford, CT 06776
  • /33

    $599,000

    • 4 Beds
    • 4.5 Baths
    • 3,088 Sq Ft

    763 Old State Route 22, Dover Plains, NY 12522

    For those seeking the ultimate in charm and comfort, The Preston House, one of the accommodations at the renowned Old Drovers Inn Bed and Breakfast, is now available for sale. This beautifully renovated 3,088 SF colonial blends old-world elegance with modern conveniences, offering a truly unique living experience. Steeped in history, the home features period architectural details throughout,

    Brian McGrath McGrath Realty Inc

    763 Old State Route 22, Dover Plains, NY 12522
  • /31

    $595,000

    • 5 Beds
    • 3 Baths
    • 2,596 Sq Ft

    310 S Kent Rd, South Kent, CT 06785

    This captivating antique property, located in South Kent, is a treasure trove of history, set against the backdrop of Kent's rolling hills. The residence, rich in character, features original details that tell a story of craftsmanship and care. Some of the details that offer a unique nod to the past, include hand-hewn beams, repurposed from a local barn and heart pine hardwood floors that have

    Phil Fox William Pitt Sotheby's Int'l

    310 S Kent Rd, South Kent, CT 06785
  • /11

    $169,000

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    14 SE Mountain Rd, Wingdale, NY 12594

    RARE FIND !! FULLY DETACTED 3 BR / 1 BTH / SPLIT LEVEL SINGLE FAMILY HOUSE W UNFIN. BSMT & FULL REAR DECK W LARGE WRAP AROUND BACK YARD LOCATED IN THE HEART OF PEACE AND TRANQILITY OF WINGDALE.. Featurning 3 BR's + WALK IN LARGE PANTRY ( 1st Floor Walk In Bedroom) Living Room, Kitchen, Basement, Large Back & Side Yard. Septic Tank for plumbing and Underground Oil Tank For Heating (SELLER NOT

    Crystal Jones Voro LLC

    14 SE Mountain Rd, Wingdale, NY 12594
  • /33

    $429,000

    • 2 Beds
    • 2 Baths
    • 1,144 Sq Ft

    593 Old State Route 22, Dover Plains, NY 12522

    Discover a remarkable, unique country retreat featuring 2 bedrooms and 2 full bathrooms. This home was completely and impeccably renovated in 2022. Nestled on 3.1 acres of private land, this exquisite property offers peace and tranquility as well as wide open spaces just up the hill behind the home with amazing mountain views. When you enter this open concept home, you immediately feel the

    MAUREEN MCELDUFF MULLANEY BHHS Hudson Valley Properties

    593 Old State Route 22, Dover Plains, NY 12522
  • /5

    $1,495,000

    • Land
    • 110 Acres
    • $13,591 per Acre

    00 Anderson Rd, Sherman, CT 06784

    Welcome to this extraordinary 110-acre parcel of land, a true gem for those seeking natural beauty and endless possibilities. With its breathtaking views and vast expanse of open land, this property offers the perfect canvas to build your dream home. This remarkable parcel also presents an incredible opportunity for developers wth the potential for an 18-lot subdivision. Imagine creating a

    Carolyn Morrison William Pitt Sotheby's Int'l

    00 Anderson Rd, Sherman, CT 06784
  • /18

    $895,000

    • Land
    • 40 Acres
    • $22,286 per Acre

    0 Spooner Hill Rd Unit 24077524, Kent, CT 06785

    Beautiful land! Discover a rare opportunity to own over 40 acres of pristine land in the picturesque Litchfield Hills, just waiting for your vision. This expansive property features beautiful old stone walls, lush woodlands, and a combination of level and gently rolling terrain-perfect for a variety of uses. Imagine building your dream estate, starting a gentleman's farm, or creating an

    Patricia Guarantano William Pitt Sotheby's Int'l

    0 Spooner Hill Rd Unit 24077524, Kent, CT 06785
  • /40

    $599,000

    • 4 Beds
    • 3.5 Baths
    • 2,700 Sq Ft

    609 Long Mountain Rd, New Milford, CT 06776

    Welcome Home to this private and scenic property in the beautiful town of Gaylordsville!! As you enter the mudroom, take your shoes off and get cozy because this house is filled with so much charm. Kitchen with concrete counters, tile floor and seated island, perfect for entertaining. Plenty of storage space in the well thought out pantry. As you enter the living area you will see hardwood floors

    Joe Chemero Coldwell Banker Realty

    609 Long Mountain Rd, New Milford, CT 06776
  • /31

    $1,895,000

    • Land
    • 18 Acres
    • $105,630 per Acre

    73 Upper Kent Hollow Rd, Kent, CT 06757

    The most exquisite building lot in Litchfield County! Stunning 300 degree views of seemingly endless rolling mountains in every direction. Enjoy both Sunrise and Sunsets on this completely private 18+/- acres. The rough driveway is installed and it's easy to traverse. The site is full cleared, blasted, scraped and flattened with retaining walls installed to make it ready to start building.

    Stacey Matthews W. Raveis Lifestyles Realty

    73 Upper Kent Hollow Rd, Kent, CT 06757
  • /2

    $599,000

    • Land
    • 8 Acres
    • $74,875 per Acre

    0 Route 22 Unit ONEH6222664, Dover, NY 12594

    Raw Land - Located on Route 22 in Wingdale/Dover Plains. Approximately 8 acres. The Town of Dover is progressing with a comprehensive rezoning initiative to allow multifamily dwellings to be built OR commercial use buildings IE shopping centers or other uses. Available is survey, and several documents limited topo, tax map, ariels etc. Proposal of a large box store drawings available but not

    Lydia Nioras Commerce Properties

    0 Route 22 Unit ONEH6222664, Dover, NY 12594
  • /13

    $2,800,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 4,000 Sq Ft

    430 Long Mountain Rd Unit LOT 1, New Milford, CT 06776

    Amazing opportunity build in gated 4 lot community in the country with privacy, beautiful mountain views and each lot has the use of 10 acres of open space. High end custom homes with pool and pool house! Plus the neighborhood backs up to farmland and open space. Breathtaking Views! Other lots to choose or owner can build to suit. (lots range from 3 to 16 acres). Great location for weekend

    Joe Chemero Coldwell Banker Realty

    430 Long Mountain Rd Unit LOT 1, New Milford, CT 06776
  • /36

    $1,275,000 Coming Soon

    • 3 Beds
    • 3.5 Baths
    • 2,736 Sq Ft

    30 Studio Hill Cir, Kent, CT 06757

    This home offers the best of the Litchfield Hills lifestyle - spacious acreage, historic New England charm, and proximity to both New York City and Boston. Beautiful contemporary on 3.3 private acres surrounded on three sides by protected Open Space, providing exceptional privacy and views of pastures and hills, but a quick drive to downtown Kent. The great room (living room/ dining room) has an

    Deborah Bain Bain Real Estate

    30 Studio Hill Cir, Kent, CT 06757
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