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Homes for Sale near South Kent School

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  • /8

    $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. This scenic location offers a peaceful setting with stunning views, serving up a perfect blend of natural beauty and New England charm. Situated in New Milford, Front of the Mountain Road has a rural feel while still providing easy access to the amenities in town and nearby

    Agent Photo

    Sharon Watson Stokland

    List N Show LLC

    (860) 752-1571

    34 Front of the Mountain Rd, New Milford, CT 06776
  • /16

    $375,000

    • 4 Beds
    • 3 Baths
    • 3,697 Sq Ft

    45 Riverdale Dr, Wingdale, NY 12594

    SHORT SALE! SALE SUBJECT TO BANK APPROVAL! THIS IS THE PERFECT HOME FOR THE EXTENDED FAMILY. 4+ BEDROOMS 3 FULL BATHS FULLY FINISHED BASEMENT. A TOTAL OF 3 CAR GARAGE, NICELY LANDSCAPED AND WITHIN CLOSE PROXIMITY TO ALL AMENITIES. BACKYARD SLOPES DOWN TO THE TEN MILE RIVER, GREAT CUL DE SAC LOCATION AND MORE. WELL KEPT. Additional Information: ParkingFeatures:1 Car Attached,2 Car Detached.

    Agent Photo

    Patricia Cannizzaro

    Century 21 Alliance Rlty Group

    (845) 493-3468

    45 Riverdale Dr, Wingdale, NY 12594
  • /39

    $964,900

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

    427 Long Mountain Rd, New Milford, CT 06776

    Experience luxury living in Merryall Section of New Milford, just 8 minutes from the historic New Milford Green. Ideally situated only 15 minutes to Metro-North, Kent, Sherman, and the scenic Litchfield Hills, this elegant Colonial home blends convenience, comfort and timeless charm. The elegant 4- Bedroom, 4.5 bath Colonial offers nearly 4,848 square feet of refined living space, set on a

    Bob Camillone Berkshire Hathaway NE Prop.

    427 Long Mountain Rd, New Milford, CT 06776
  • /40

    $1,795,000

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

    168 Cobble Rd, Kent, CT 06757

    Escape to this mountaintop retreat with sweeping, unobstructed views located off one of the most desirable scenic roads in the Litchfield Hills. Set in complete privacy, this four-bedroom home offers a perfect blend of comfort and sophistication with an open-concept layout designed for both relaxation and entertaining. The chef's kitchen, featuring a central island, flows seamlessly into a cozy

    Steve Pener William Pitt Sotheby's Int'l

    168 Cobble Rd, Kent, CT 06757
  • /40

    $1,250,000

    • 3 Beds
    • 2 Baths
    • 1,796 Sq Ft

    159 Merryall Rd, New Milford, CT 06776

    Painted River is a rare offering in the Merryall community of New Milford, Litchfield County. Set at the end of a 400-foot private drive, this 6+ acre property offers complete seclusion with direct frontage on the West Aspetuck River. River views, glowing westerly sunsets, and preserved frontage guarantee privacy for years to come. Groomed walking trails weave through fenced meadows and mature

    Jake Garay Serhant Connecticut, LLC

    159 Merryall Rd, New Milford, CT 06776
  • /42

    $899,000

    • 4 Beds
    • 3 Baths
    • 1,850 Sq Ft

    73 Lake Ellis Rd, Wingdale, NY 12594

    Welcome to your private equestrian retreat, just 4 miles from the Harlem–Valley Wingdale Train Station, 4 miles to charming Kent, CT, a mile away to the Appalachian Trail & easy access to Route 7 & Route 22. Set on a secluded private road off Lake Ellis, this property offers both convenience & privacy. Equestrian amenities include a main barn with 6 (12x10) stalls w/ hay loft, heated wash stall,

    Christine Ricci Keller Williams NY Realty

    73 Lake Ellis Rd, Wingdale, NY 12594
  • /31

    $1,395,000

    • 4 Beds
    • 3.5 Baths
    • 3,247 Sq Ft

    73 Long River Rd, Sherman, CT 06784

    This elegant four-bedroom home, built in 2021, is perfectly sited on 1.8 acres of professionally landscaped, private grounds. Designed for effortless single-level living, it features an open-concept layout with a chef's kitchen and center island, a welcoming living room with fireplace, and a sunlit dining area that all flows seamlessly to a covered porch with views toward the Housatonic River.

    Steve Pener William Pitt Sotheby's Int'l

    73 Long River Rd, Sherman, CT 06784
  • /35

    $1,275,000

    • 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
  • /43

    $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

    $820,000

    • 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
  • /37

    $810,000

    • 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
  • /27

    $499,000

    • 3 Beds
    • 1.5 Baths
    • 1,816 Sq Ft

    10 Biliski Rd, New Milford, CT 06776

    Charming Country Retreat on 2.69 Private Acres Escape to this inviting 1,816 sq. ft. home tucked away on a peaceful country road and surrounded by natural beauty. Set on 2.69 acres with gardens and distant hillside views, this property offers the perfect blend of privacy and charm. A large, sun-filled galley kitchen featuring wood floors, a cozy fireplace, and plenty of space for casual dining.

    John Sniffen William Pitt Sotheby's Int'l

    10 Biliski Rd, New Milford, CT 06776
  • /39

    $539,000

    • 4 Beds
    • 2 Baths
    • 2,760 Sq Ft

    48 Gaylord Rd, Gaylordsville, CT 06755

    Step into history with this one-of-a-kind antique Colonial, dating back to the 1700s and once serving as a Revolutionary War-era tavern. Legend has it, even George Washington passed through these doors to rally his troops and plan their next move-making this home not just a residence, but a true piece of history. Nestled on 2 peaceful acres in the charming village of Gaylordsville, this

    Debra Tricarico Houlihan Lawrence

    48 Gaylord Rd, Gaylordsville, CT 06755
  • /29

    $539,000 Open Sat 11AM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 2,176 Sq Ft

    27 Bridle Rd, New Milford, CT 06776

    Welcome home! Check out this spacious 4-bedroom Colonial set on a level lot in Upper Merryall. The main level features a roomy living room, formal dining room, and an eat-in kitchen, complemented by a comfortable family room with a wood-burning fireplace. Upstairs offers four well-proportioned bedrooms and two full bathrooms. Outdoor living is enhanced by a cedar deck overlooking the private rear

    Kurt Stoffel Coldwell Banker Realty

    27 Bridle Rd, New Milford, CT 06776
  • /40

    $489,900

    • 4 Beds
    • 2 Baths
    • 1,613 Sq Ft

    49 Quaker Ridge Rd, Sherman, CT 06784

    Cape on Quaker Ridge! Looking for an affordable entry into Sherman? This 4-bedroom, 2-bath Cape, set at the end of a quiet cul-de-sac on sought-after Quaker Ridge Road, offers just that-plus a premium 2.28-acre lot. Owned by the same owner for over 40 years, this home is ready for its next chapter and new owners to enjoy for decades to come. Opportunities for expansion are plentiful, with an

    Todd Sargent Coldwell Banker Realty

    49 Quaker Ridge Rd, Sherman, CT 06784
  • /27

    $425,000

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

    80 N Main St Unit 1A1, Kent, CT 06757

    This inviting 2-bedroom condo is just steps from shopping, restaurants, and Kent's charming sidewalks-perfect for an afternoon stroll through the village. As soon as you open the door, sunlight fills the living and dining area, highlighting the cozy wood-burning fireplace. The kitchen and two full baths have been tastefully updated with granite counters, modern cabinetry, and easy-care laminate

    Toni Soule Bain Real Estate

    80 N Main St Unit 1A1, Kent, CT 06757
  • /40

    $2,395,000

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

    14 Straight Rd, Kent, CT 06757

    Private Estate with Panoramic Views in Coveted Kent Hollow. Tucked at the end of a quiet country lane, this rare 15+ acre estate offers stunning views, complete privacy, and timeless New England charm. Perfectly perched to overlook the beauty of Kent Hollow, the property blends refined living with the tranquility of nature. The 4-bedroom, 4 bath (2 Full, 2 Half) main residence is designed for

    Pels Matthews W. Raveis Lifestyles Realty

    14 Straight 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
  • /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
  • /17

    $340,000

    • 2 Beds
    • 1 Bath
    • 1,774 Sq Ft

    16 Gaylord Rd, Gaylordsville, CT 06755

    Light-Filled Ranch on a Quiet, Conveniently located Lot. Welcome to this light, bright, and truly charming ranch home, perfectly situated on a picturesque 0.86-acre lot. This home offers an easy and flexible floor plan ideal for both everyday living and entertaining. The eat-in kitchen is open and welcoming, while the finished lower-level family room (not included in total square footage)

    Dave Fairty Regency Real Estate, LLC

    16 Gaylord Rd, Gaylordsville, CT 06755
  • /22

    $279,000

    • Land
    • 5.46 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
    • 15.47 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

    $489,000

    • 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
  • /6

    $489,000

    • Land
    • 13.47 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
  • /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
  • /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
  • /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
  • /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
    • 40.16 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
  • /31

    $1,895,000

    • Land
    • 17.94 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
  • /37

    $1,500,000

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

    13 Cobble Heights Rd, Kent, CT 06757

    You'll find this Tudor and Stucco style home nestled on 8 private acres with a pond, on a private road 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 has a separate entrance and includes a large living area, a bedroom and full bathroom. There are 3 stunning stone fireplaces with custom designed mantels that

    Janet Nelson William Pitt Sotheby's Int'l

    13 Cobble Heights 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
  • /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
  • /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
  • /17

    $225,000 Pre-Foreclosure

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    152 S Kent Rd, Gaylordsville, CT 06755

    This 3BR 1 Bath ranch offers opportunities. Use your vision and expertise to transform the property to modern day living. Quiet location- closed to many CT peaceful towns as well. Sold "as is" where is.

    Donna Myjak CRS,SRES,SRS Berkshire Hathaway NE Prop.

    152 S Kent Rd, Gaylordsville, CT 06755
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