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Homes for Sale near Kent School

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  • /20

    $356,500

    • 3 Beds
    • 1.5 Baths
    • 1,108 Sq Ft

    39 Maple Ln, Dover Plains, NY 12522

    Accepted Offer OK to show but there are 2 back up offers. Multiple offers Highest and best due Monday 09/22/25 by 4:00PM39 Maple Lane, Dover Plains, NY is being offered for sale for the first time since it was built in 1970. There is a blacktop driveway, a fenced in level yard and an ELEVATOR from ground level to upper level. This home appears to be well built and offers plenty of

    Agent Photo

    Larry Havens

    Havens Real Estate

    (845) 506-8855

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

    $419,000

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

    105 S Nellie Hill Rd, Dover Plains, NY 12522

    OPEN HOUSE 10/26 from 11 to 2. The seller's family has moved abroad. They are very motivated. See new Price! 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

    Agent Photo

    Larry Havens

    Havens Real Estate

    (845) 478-1624

    105 S Nellie Hill Rd, Dover Plains, NY 12522
  • /37

    $875,000

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    103 Geer Mountain Rd, South Kent, CT 06785

    Set well back from the road across Bull Mountain Brook is this incredibly private brookside home on South Kent's lauded Geer Mountain Rd. Perched over the brook the house offers 1750 sq. ft. of wood floors, three fireplaces, open floorplan and plenty of windows for views and sunlight. There are three bedrooms with the primary on the main level for ease and comfort. The screened porch offers a

    Chris Garrity Bain Real Estate

    103 Geer Mountain Rd, South Kent, CT 06785
  • /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
  • /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
  • /33

    $2,300,000

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

    221 Fuller Mountain Rd, Kent, CT 06757

    This extraordinary residence is a masterful blend of timeless architectural inspiration and modern luxury, offering a rare opportunity to own a home that is both a work of art and a private retreat. Designed in homage to the style of Frank Lloyd Wright, it features hipped roofs with wide eaves, long horizontal lines, and a seamless integration with the natural landscape. The house is set well

    Steve Pener William Pitt Sotheby's Int'l

    221 Fuller Mountain Rd, Kent, CT 06757
  • /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
  • /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
  • /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
  • /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. A Truly Enchanting c1850 Country Retreat That Blends Timeless Character with Refined Comfort. 2-3 Bed, 3-Bath Main House Offers; Gracious Proportions, High Ceilings, 3 Fireplaces, and Exquisite Period Detailing Throughout. A Separate Grand Antique Converted Barn-Skillfully Transformed into a Dramatic Guest House & Entertaining Space-Boasts Soaring Beamed

    Graham Klemm Klemm Real Estate Inc

    278A Kent Cornwall 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
  • /36

    $350,000 Open Sun 11AM - 2PM

    • 2 Beds
    • 1 Bath
    • 1,296 Sq Ft

    228 Dog Tail Corners Rd, Wingdale, NY 12594

    228 Dog Tail Corners – Country Charm with Endless Potential. Welcome to this classic 1928 family home, brimming with country charm and timeless character. With hardwood floors, a welcoming living room, and a handy entryway mudroom, this home offers both comfort and functionality throughout. The kitchen is ready to be reimagined into your dream cooking and gathering space. The first-floor features

    Peggy MacLeay-Generoso McGrath Realty Inc

    228 Dog Tail Corners Rd, Wingdale, NY 12594
  • /18

    $215,000

    • 2 Beds
    • 2 Baths
    • 1,680 Sq Ft

    140 Dove Dr, Dover Plains, NY 12522

    This home is in very good condition and located in a well maintained 55 and over community.Monthly rent includes: taxes, water, streetlights and garbage pickup .

    Richard Rennia Richard A. Rennia

    140 Dove Dr, Dover Plains, NY 12522
  • /17

    $64,900

    • 2 Beds
    • 2 Baths
    • 924,924 Sq Ft

    62 Cardinal Ct, Dover Plains, NY 12522

    This home is in good condition and is located in a well maintained 55 and over community. Monthly rentincludes: taxes, water, streetlights and garbage pickup.

    Richard Rennia Richard A. Rennia

    62 Cardinal Ct, Dover Plains, NY 12522
  • /16

    $89,900

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    108 Bluebird Way, Dover Plains, NY 12522

    This home is in good condition and located in a well maintained 55 and over community. Monthly rent includes: taxes, water, streetlights and garbage pickup.

    Richard Rennia Richard A. Rennia

    108 Bluebird Way, Dover Plains, NY 12522
  • /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
  • /9

    $90,000

    • 2 Beds
    • 1 Bath

    94 Park Dr, Dover Plains, NY 12522

    55 AND OVER ONLY...NICE 2 BEDROOM ONE BATH EAT IN KITCHEN, SCREENED IN PORCH. CENTRAL AC, BACK DECK JUST PAINTED. NICE QUIET PARK.

    KIMBERLY DIGIACOMO Tassone Realty Corp.

    94 Park Dr, Dover Plains, NY 12522
  • /40

    $8,000,000

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

    33 Nodine Pasture Rd, Kent, CT 06757

    West Wind Hill, a bespoke country estate on 389 acres sits on the crest of a plateau overlooking panoramic protected views. Classic stone and shingle manor house with formal courtyard sited perfectly to experience spectacular sunsets and fairytale mists combined with the upmost in privacy. Access is via a private gated road that winds through trees, past old stone walls with glimpses of open

    Jill Sloane Brown Harris Stevens

    33 Nodine Pasture Rd, Kent, CT 06757
  • /18

    $449,900

    • 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
  • /38

    $380,000

    • 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
  • /26

    $597,500

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

    132 S Kent Rd, South Kent, CT 06785

    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 also includes a

    Steve Pener William Pitt Sotheby's Int'l

    132 S Kent Rd, South Kent, CT 06785
  • /2

    $180,000

    • Land
    • 5 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 Redfin Real Estate

    591 Bog Hollow Rd, Wassaic, NY 12592
  • /40

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,397 Sq Ft

    42 Lime Kiln Rd, Dover Plains, NY 12522

    Perfectly set back on beautiful park-like property showcasing spectacular panoramic mountain views and a small babbling brook at the back of the property that flows from the Ten Mile River. Bright spacious floor plan features hardwood floors through first floor, updated granite & maple kitchen with stainless steel appliances, and a recently remodeled bath with a custom tile & seamless glass

    Susan Todd BHHS Hudson Valley Properties

    42 Lime Kiln Rd, Dover Plains, NY 12522
  • /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
  • /4

    $299,000

    • Land
    • 12.18 Acres
    • $24,548 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
    • 20.15 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
  • /23

    $895,000

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

    0 Spooner Hill Rd Unit 24077524, Kent, CT 06785

    Discover a rare opportunity to own over 40 acres of pristine land in the picturesque Litchfield Hills. 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 equestrian paradise. Located in Kent, a vibrant and

    Patricia Guarantano William Pitt Sotheby's Int'l

    0 Spooner Hill Rd Unit 24077524, Kent, CT 06785
  • /5

    $340,000

    • Land
    • 5.5 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
    • 14.87 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
    • 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
  • /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

    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

    $395,000

    • Land
    • 13.79 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
  • /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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