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Homes for Sale near Kent School

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  • /21

    $359,000

    • 3 Beds
    • 1.5 Baths
    • 1,628 Sq Ft

    39 Maple Ln, Dover Plains, NY 12522

    Deal Fell Through Back on the MarketFor the first time this well constructed 3-bedroom, 1.5 bath home on a huge level lot is being offered to settle the Estate. Each room is well proportioned, ample closets, the ceiling height is 7'6", the home is dated, the carpets are worn and need to be replaced. Under the carpet there is hardwood floors that will change the complexion 110%. The lower

    Agent Photo

    Larry Havens

    Havens Real Estate

    (845) 506-8855

    39 Maple Ln, Dover Plains, NY 12522
  • /23

    $469,000

    • 3 Beds
    • 2 Baths
    • 1,523 Sq Ft

    105 S Nellie Hill Rd, Dover Plains, NY 12522

    Circa 1952 - A delightful home that has been totally transformed into a casually elegant masterpiece.The roof was replaced in 2012. The siding was replaced in 2022. The interior of the home was totally redone in 2024.The floors are exquisite, the tiled baths are luxurious, the kitchen is a dream (quartz counter and back splash), and the flow is welcoming. The sun filled deck supports

    Agent Photo

    Larry Havens

    Havens Real Estate

    (845) 478-1624

    105 S Nellie Hill Rd, Dover Plains, NY 12522
  • /40

    $2,395,000

    • 4 Beds
    • 2.5 Baths
    • 3,392 Sq Ft

    14 Straight Rd, Kent, CT 06757

    AAA location in Kent Hollow just west of Lake Waramaug. Extremely private 15+ acres at end of Straight Road with 3-4 bedroom, 2.5 bath main residence and 2 bedroom, 2 bath guesthouse. Primary house sits high on the property down a long driveway with views of Kent Hollow ridgelines. The 1950's modern style guesthouse is discretely located half way along the driveway. Features of the house include

    Pels Matthews W. Raveis Lifestyles Realty

    14 Straight Rd, Kent, CT 06757
  • /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
  • /29

    $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

    $2,300,000

    • 4 Beds
    • 5 Baths
    • 5,512 Sq Ft

    221 Fuller Mountain Rd, Kent, CT 06757

    As you approach this radiant modern homestead, a gracefully winding driveway crosses the picturesque Jack brook on a newly restored wood trestle bridge, framed by specimen trees and meticulously crafted stonework, creating a breathtaking entrance. The home's expansive design seamlessly blends indoor and outdoor living, offering a harmonious flow throughout. At its heart, a striking stone

    Holly Leibrock Elyse Harney Real Estate

    221 Fuller Mountain Rd, Kent, CT 06757
  • /26

    $1,750,000

    • 3 Beds
    • 3 Baths
    • 2,272 Sq Ft

    278A Kent Cornwall Rd, Kent, CT 06757

    Utterly Magical Kent Compound with Pool. c1850 2-3 Bedroom, 3 Bath Main House with High Ceilings, 3 Fireplaces & Wonderful Period Details. Separate Grand Antique Party Barn/Guest House with 1 Bedroom & 2 Full Baths; High Ceilings; Beams & Views. Central Gunite Pool with Cabana & 2-Car Garage. Less than 5 Min to the Center of Kent CT & 20 Min to Metro North Train.

    Graham Klemm Klemm Real Estate Inc

    278A Kent Cornwall Rd, Kent, CT 06757
  • /33

    $369,000

    • 2 Beds
    • 2 Baths
    • 1,700 Sq Ft

    50 Lake Ellis Rd, Wingdale, NY 12594

    Tastefully updated colonial situated on one acre park-like property. Flexible and versatile floor plan offers spacious renovated kitchen w/quartz counters & stainless appliances, huge living room, first floor mudroom/laundry room, two first floor bedrooms and full bathroom. Second floor includes three additional rooms plus full bathroom. New vinyl flooring, fresh paint, new furnace, water heater

    Dan Axtmann BHHS Hudson Valley Properties

    50 Lake Ellis Rd, Wingdale, NY 12594
  • /18

    $475,000

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft

    441 Segar Mountain Rd, South Kent, CT 06785

    This spacious ranch style house has a new roof, new vinyl siding, some new windows and new deck plus covered front porch. Remodeled eat in kitchen has white shaker style cabinets with granite counter tops, hardwood flooring and stainless steel appliances. Living room has bay window, hardwood floors and fireplace. Two good size bedrooms plus two fully remodeled bathrooms. Formal dining room. There

    Barry Mackiewicz A-Gold Action Realty

    441 Segar Mountain Rd, South Kent, CT 06785
  • /19

    $439,000 Open Sun 10:30AM - 12PM

    • 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
  • /2

    $150,000

    • Land
    • 2.71 Acres
    • $55,351 per Acre

    0 S Kent Rd Unit 24121645, Kent, CT 06757

    Build your dream home on this 2.71 acre lot in South Kent. Enjoy the beautiful town of Kent with wonderful restaurants, shops, art galleries, hiking trails and Kent Falls State Park. Enjoy fly fishing and boating on the Housatonic River. Metro North train nearby to get to NYC. Kent has consistently received national recognition, being named one of America's most beautiful main streets by Reader's

    Janet Nelson William Pitt Sotheby's Int'l

    0 S Kent Rd Unit 24121645, Kent, CT 06757
  • /38

    $400,000

    • 4 Beds
    • 3 Baths
    • 1,792 Sq Ft

    263 Bog Hollow Rd, Wassaic, NY 12592

    Welcome to this beautifully renovated 4-bedroom, 3-bath Colonial style home nestled on 2.9 private acres in the charming town of Amenia, NY. The open concept living room features a pellet stove and access to the kitchen and 1st floor bathroom. The kitchen hs stainless steel appliances and butcher block counters and cute breakfast nook. The laundry room is on the first floor. Aslo on the main

    Christopher Ferraro RE/MAX Town & Country

    263 Bog Hollow Rd, Wassaic, NY 12592
  • /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
  • /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
  • /14

    $80,000

    • Land
    • 1.01 Acres
    • $79,208 per Acre

    15 Evan Rd, Dover Plains, NY 12522

    Attention builders and end users! Level, cleared and shovel ready 1 acre lot in the heart of Dover Plains! Current 4 bedroom BOHA, no fill required for the septic. Backing up to 16+ acres of farm land, come build your dream home today! Bring your own builder or ask about options. Excellent location, minutes to town, the Town of Amenia, Wassaic Train Station, culinary grade restaurants shops and

    Justin LaFalce KW MidHudson

    15 Evan Rd, Dover Plains, NY 12522
  • /2

    $180,000

    • Land
    • 5.00 Acres
    • $36,000 per Acre

    591 Bog Hollow Rd, Wassaic, NY 12592

    Discover the perfect blend of peace, privacy, and potential with this beautiful 5-acre residential building lot located in the scenic hamlet of Wassaic, NY. Nestled in the heart of Dutchess County, this spacious parcel offers a rare opportunity to build your dream home or weekend retreat surrounded by nature. With ample space for a custom residence, gardens, and outdoor living areas, the

    Tiffiany West RE/MAX Distinguished Hms.&Prop

    591 Bog Hollow Rd, Wassaic, NY 12592
  • /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
  • /4

    $350,000

    • Land
    • 12 Acres
    • $28,736 per Acre

    00 Old Homestead Ln, Kent, CT 06757

    Build your dream home at 17 Old Homestead Ln, South Kent in St. John's Peak. Set in the bucolic foothills of the Litchfield Hills, St Johns Peak is one of Connecticut's most bucolic enclaves. Enjoy unmatched tranquility and natural wonder on this sprawling and park-like 12+ acre property. Enjoy the beloved downtown of Kent to absorb the culture and natural beauty of Litchfield Hills and

    Jaime Richichi William Pitt Sotheby's Int'l

    00 Old Homestead Ln, Kent, CT 06757
  • /9

    $399,999

    • Land
    • 20 Acres
    • $19,851 per Acre

    0 Stonewall Unit 39, Kent, CT 06757

    Desirable acreage within the scenic St Johns Peak in Kent! Under ground utilities, private road located at the end of culdesac

    Diane Carroll The Washington Agency

    0 Stonewall Unit 39, Kent, CT 06757
  • /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
  • /5

    $340,000

    • Land
    • 6 Acres
    • $61,818 per Acre

    00 Upper Kent Hollow Rd, Kent, CT 06757

    Approximately 5.5 acres in south Kent. This is a top location abutting major estates and just minutes to the state beach at Lake Waramaug and the Lake Waramaug County Club (beach, tennis, golf, clubhouse dining). This property is equi-distant between the charming villages of Kent, New Preston and Washington. Bring your architect and build your dream. 1 hour 45 minutes to NYC. Offer is subject to

    Stacey Matthews W. Raveis Lifestyles Realty

    00 Upper Kent Hollow Rd, Kent, CT 06757
  • /12

    $425,000

    • Land
    • 15 Acres
    • $28,581 per Acre

    0 W Woods Rd Unit 1 24061899, Kent, CT 06757

    This nearly 15 acres of quiet woods, nestled between National Audubon lands to the north and NW Land Conservancy to the south, assures ultimate privacy while only minutes from the center of Sharon, CT. Located on a quiet gravel town road, a gently sloping driveway winds its way to a lovely, flat clearing with stonewalls, large native trees offering a natural building site. Sloping easily to the

    Chris Garrity Bain Real Estate

    0 W Woods Rd Unit 1 24061899, Kent, CT 06757
  • /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
  • /36

    $8,000,000

    • 6 Beds
    • 8 Baths
    • 8,933 Sq Ft

    Unlisted Address

    Perched on the crest of a plateau overlooking panoramic, protected views, West Wind Hill, a bespoke country estate on 389± acres, straddles Kent, CT and Amenia, NY. Experience this truly magnificent classic stone and shingle manor house sited perfectly to experience lush sunsets and fairytale mists with the upmost in privacy. Only eight minutes from the center of Kent and less than two

    Joseph Lorino Brown Harris Stevens HV LLC

    Unlisted Address
  • /40

    $8,000,000

    • 4 Beds
    • 5.5 Baths
    • 5,400 Sq Ft

    23 Mauwee Brook Rd, Kent, CT 06757

    "The Falls." Prominent Modernist Architect, Charles Gwathmey of Guggenheim Museum renovation fame, designed this masterpiece in one of the most beautiful locations, offering dramatic views, cascading waterfall, nestled on 40+ acres of beautifully landscaped grounds with serene stream and extensive stonework. The property boasts a breathtaking western view of the Litchfield Hills. Just minutes to

    Kathryn Clair William Pitt Sotheby's Int'l

    23 Mauwee Brook Rd, Kent, CT 06757
  • /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

    $395,000

    • Land
    • 14 Acres
    • $28,644 per Acre

    1 W Woods Rd, Kent, CT 06757

    Desirable West Woods location for this 13.975 acres, bordering Sharon Land Trust property. Lightly wooded, with a gentle stream crossing near the northern boundary of the parcel. The high ground at the southern end of the lot provides an ideal building site with potential western views. Minutes to town and Wassaic train service to NYC.

    David Taylor Elyse Harney Real Estate

    1 W Woods 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
  • /35

    $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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