Kent, CT Homes

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  $1,650,000

  $145K PRICE DROP

  • 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
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  /33

  $12,000 Per Month

  • 6 Beds
  • 4 Baths
  • 4,698 Sq Ft
  • House for Rent

  141 Geer Mountain Rd, South Kent, CT 06785

  TIME TO PLAN YOUR SUMMER VACATION! OR RENT YEARLY! Available June and July. Call for Summer Pricing! Enjoy country living in this stunning location with spectacular views and total privacy. Only 90 minutes from NYC. Swim in the heated gunfire pool. Explore the homes 142 acres. Plenty of room for family and friends who want to experience the beauty of Litchfield County. There is a 6 Bedroom main

  Sharon McGuire William Pitt Sotheby's Int'l

  141 Geer Mountain Rd, South Kent, CT 06785
• 

  $300,000

  Sold Sep 05, 2025

  7 Pheasant Run Rd Unit 1, Kent, CT 06757

  • 3 Beds
  • 1.5 Baths
  • 1,560 Sq Ft
  • Built 1981

  Last Sold Summary

  • $192/SF
  • 56 Days On Market

  Current Estimated Value $321,625

  Last Listing Agent Doug Hagen Starr Team at LPT Realty

  7 Pheasant Run Rd Unit 1, Kent, CT 06757
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  Not Listed For Sale

  49 Botsford Rd, Kent, CT 06757

  • Built 1949

  49 Botsford Rd, Kent, CT 06757

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent David Bain Bain Real Estate
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  /18

  $995,000

  $255K PRICE DROP Under Contract Pre-Foreclosure

  • 3 Beds
  • 3 Baths
  • 3,296 Sq Ft

  308 Skiff Mountain Rd, Kent, CT 06757

  A remarkable 139-acre property located up on Skiff Mountain surrounded by 7,000 acres of protected lands. Most of the property is conserved under the Forest Legacy Program, with building envelopes to include the existing home, barns and detached garage. The value is simply the location and the home can either be renovated or torn down to prepare for building new. The home site overlooks a

  John Harney William Pitt Sotheby's Int'l

  308 Skiff Mountain Rd, Kent, CT 06757
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  $20,000 Per Month

  • 4 Beds
  • 2 Baths
  • 2,165 Sq Ft
  • House for Rent

  594 Skiff Mountain Rd, Kent, CT 06757

  Spend your summer atop Skiff Mountain with a jaw-dropping views, hidden privacy a poolside paradise! Situated at over 1300 feet of elevation and beside expansive hay fields, this is the spot only the envied get to enjoy. Generations have enjoyed these breathtaking views from sunrise to sunset. Relax and take in the pastoral setting over a 10 acre hayfield that expands to miles of viewshed across

  Chris Garrity Bain Real Estate

  594 Skiff Mountain Rd, Kent, CT 06757
• 

  $2,400,000

  Sold Aug 05, 2026

  100 N Main St, Kent, CT 06757

  • 4 Beds
  • 6 Baths
  • 5,345 Sq Ft
  • Built 1800

  Last Sold Summary

  • 8% Below List Price
  • $449/SF
  • 30 Days On Market

  Current Estimated Value $2,577,970

  Last Listing Agent Jeff Phillips William Pitt Sotheby's Int'l

  100 N Main St, Kent, CT 06757
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  Est $611,463

  Not Listed For Sale

  2 Tamshell Dr, Kent, CT 06757

  • 3 Beds
  • 2.5 Baths
  • 2,242 Sq Ft
  • Built 1979

  2 Tamshell Dr, Kent, CT 06757

  Last Sold Summary

  • 69 Days On Market

  Last Listing Agent Vince McGough McGough Realty Corp.
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  $525,000

  • Land
  • 8.22 Acres
  • $63,869 per Acre

  0 Mount Mauwee Rd, Kent, CT 06757

  8.22 acre parcel in private and exclusive St. John's Peak subdivision of Kent! Take the winding road through this peaceful and secluded area to find your future home site! With road frontage of 75 feet, the topography of this lot is mostly level, and it gently slopes down from the approved home site to the Mauwee Brook. 2004 Perc/Soil tests on file with the health district, was previously

  Katherine Parlato Drakeley Real Estate, Inc.

  0 Mount Mauwee Rd, Kent, CT 06757
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  /5

  $20,000 Per Month

  • 3 Beds
  • 3 Baths
  • 2,384 Sq Ft
  • House for Rent

  40 Camps Flat Rd, South Kent, CT 06785

  Experience the ultimate country retreat with this charming, fully furnished 3-bedroom, 3-bathroom cottage set on 13+ private acres. Available for the Academic year or Winter rental, this inviting property features a heated saltwater gunite pool, a separate guest cottage, beautifully maintained grounds, and perennial gardens. The main residence boasts a sun-filled kitchen with an eat-in area, a

  Vanessa Henderson William Pitt Sotheby's Int'l

  40 Camps Flat Rd, South Kent, CT 06785
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  $440,000

  Sold Nov 19, 2025

  80 N Main St Unit 10, Kent, CT 06757

  • 2 Beds
  • 1.5 Baths
  • 1,201 Sq Ft
  • Built 1980

  Last Sold Summary

  • 2% Below List Price
  • $366/SF
  • 56 Days On Market

  Current Estimated Value $394,054

  Last Listing Agent Sharon Hartwick William Pitt Sotheby's Int'l

  80 N Main St Unit 10, Kent, CT 06757
• 

  Est $628,870

  Not Listed For Sale

  16 Botsford Rd, Kent, CT 06757

  • 3 Beds
  • 2 Baths
  • 1,896 Sq Ft
  • Built 1992

  16 Botsford Rd, Kent, CT 06757

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Sharon Hartwick William Pitt Sotheby's Int'l
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  $1,139,000

  • 4 Beds
  • 4 Baths
  • 4,442 Sq Ft

  11 Stone Fences Ln, Kent, CT 06785

  This exquisitely appointed Colonial estate has the WOW factor! At its heart lies an opulant living room, where soaring cathedral ceilings meet a wall of grand windows, inviting the outdoors in, while a bespoke fireplace serves as a luminous anchor of comfort. The expansive, double height windows provide dramatic light to the open plan living/ dining/ kitchen. Miele and Bosch appliances are

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

  11 Stone Fences Ln, Kent, CT 06785
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  $20,000 Per Month

  • 3 Beds
  • 3 Baths
  • 2,777 Sq Ft
  • House for Rent

  16 Anderson Acres, Kent, CT 06757

  Experience the ultimate August retreat at 16 Anderson Acres Road, a contemporary masterpiece perched in the heart of Kent. This architectural gem is designed to blur the lines between luxury and nature, offering unrivaled panoramic views that stretch for miles from nearly every room in the house. Whether you are sipping your morning coffee in the open-concept living space or unwinding by the

  Phil Fox William Pitt Sotheby's Int'l

  16 Anderson Acres, Kent, CT 06757
• 

  $577,000

  Sold Oct 21, 2025

  311 Kent Rd, Kent, CT 06757

  • 3 Beds
  • 1.5 Baths
  • 1,548 Sq Ft
  • Built 1947

  Last Sold Summary

  • 3% Below List Price
  • $373/SF
  • 31 Days On Market

  Current Estimated Value $616,128

  Last Listing Agent Steve Pener William Pitt Sotheby's Int'l

  311 Kent Rd, Kent, CT 06757
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  Est $1,383,234

  Not Listed For Sale

  123 Kent Hollow Rd, Kent, CT 06757

  • 4 Beds
  • 4 Baths
  • 2,492 Sq Ft
  • Built 2017

  123 Kent Hollow Rd, Kent, CT 06757

  Last Sold Summary

  • 112 Days On Market

  Last Listing Agent Steve Pener William Pitt Sotheby's Int'l
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  /14

  $335,000

  $30K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,622 Sq Ft

  Unlisted Address

  Close to Kent's village shops and restaurants, this well-appointed townhouse offers the ease of in-town living with the feel of a private retreat. The main level centers on a light-filled living room with fireplace that opens to a spacious deck - a natural gathering spot with long sunset views. The formal dining room connects to a separate back deck, quiet and shaded, ideal for morning coffee.

  Steve Pener William Pitt Sotheby's Int'l

  Unlisted Address
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  /20

  $3,500 Per Month

  • 4 Beds
  • 2 Baths
  • 2,436 Sq Ft
  • House for Rent

  42 South Rd, Kent, CT 06757

  Fantastic private Kent, CT home with oodles of space to enjoy. Lightly furnished rental that offers easy access to the village of Kent in a 3 acre wooded setting with a spacious lawn. The home has large rooms that provides considerable public space and ample bedrooms. There is plenty of rooms for offices and for living. Oak flooring throughout all in top condition. The country kitchen fits a full

  Chris Garrity Bain Real Estate

  42 South Rd, Kent, CT 06757
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  /17

  $1,095,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 2,244 Sq Ft

  262 Kent Cornwall Rd, Kent, CT 06757

  Set well back from the road on more than 29 private acres, this single-level three-bedroom home offers something increasingly rare in Litchfield Hills: commanding western views, serious acreage, and the freedom to make it entirely your own. Originally built in 1962 with genuine mid-century sensibility, the home is low-slung and organized around an open living concept with a fireplace, dining

  Steve Pener William Pitt Sotheby's Int'l

  262 Kent Cornwall Rd, Kent, CT 06757
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  Est $426,616

  Not Listed For Sale

  80 N Main St Unit 28, Kent, CT 06757

  • 2 Beds
  • 2.5 Baths
  • 1,624 Sq Ft
  • Built 1987

  80 N Main St Unit 28, Kent, CT 06757

  Last Sold Summary

  • 64 Days On Market

  Last Listing Agent Karen Casey William Pitt Sotheby's Int'l
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  /39

  $1,825,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,910 Sq Ft

  68 Anderson Rd, Kent, CT 06757

  Tucked along the scenic beauty of Anderson Road-one of Kent's most coveted addresses - this enchanting country estate offers a true escape. A pea-stone driveway guides you past lush landscaping, field stone walkways, the charming 1835 main house, and on toward the stunning barns, revealing the property's timeless elegance, piece by piece. The main residence brims with original character - wide

  Stacey Matthews W. Raveis Lifestyles Realty

  68 Anderson Rd, Kent, CT 06757
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  $2,900 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,596 Sq Ft
  • House for Rent

  317 Skiff Mountain Rd, Kent, CT 06757

  Discover the perfect balance of peaceful country living and modern comfort at this renovated, partially furnished 3-bedroom, 2-bathroom home, offering approximately 1,550+ square feet of thoughtfully designed living space. Nestled along one of Kent's most scenic country roads on sought-after Skiff Mountain, this inviting residence provides a private retreat surrounded by nature while remaining

  Samantha Behm William Pitt Sotheby's Int'l

  317 Skiff Mountain Rd, Kent, CT 06757
• 

  $555,000

  Sold Apr 27, 2026

  132 S Kent Rd, South Kent, CT 06785

  • 4 Beds
  • 2.5 Baths
  • 2,469 Sq Ft
  • Built 1979

  Last Sold Summary

  • 12% Below List Price
  • $225/SF
  • 260 Days On Market

  Current Estimated Value $585,049

  Last Listing Agent Steve Pener William Pitt Sotheby's Int'l

  132 S Kent Rd, South Kent, CT 06785
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  Not Listed For Sale

  5 Weantinoge Ln, Kent, CT 06757

  5 Weantinoge Ln, Kent, CT 06757

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Donna Kennedy Compass Connecticut, LLC
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  /40

  $6,500,000

  $2M PRICE DROP

  • 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
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  /40

  $6,000 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,296 Sq Ft
  • House for Rent

  47 Johnson Rd, Kent, CT 06757

  Embrace the art of living well at Poetess Place, a haven designed for writers, birders, and nature lovers, tucked away on a private riverfront perch in the heart of picturesque Kent, CT. This lovingly remodeled 3-bedroom cottage, each room adorned with queen-sized comfort, invites you into a world of warmth and serenity. Wake up to the soothing melody of the Housatonic River and be captivated by

  Inna Agujen Coldwell Banker Realty

  47 Johnson Rd, Kent, CT 06757
• 

  $540,000

  Sold Oct 21, 2025

  310 S Kent Rd, South Kent, CT 06785

  • 5 Beds
  • 3 Baths
  • 2,596 Sq Ft
  • Built 1900

  Last Sold Summary

  • 17% Below List Price
  • $208/SF
  • 153 Days On Market

  Current Estimated Value $531,521

  Last Listing Agent Phil Fox William Pitt Sotheby's Int'l

  310 S Kent Rd, South Kent, CT 06785
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  Est $481,275

  Not Listed For Sale

  80 Kent Hollow Rd, South Kent, CT 06785

  • 3 Beds
  • 2 Baths
  • 1,095 Sq Ft
  • Built 1957

  80 Kent Hollow Rd, South Kent, CT 06785

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent David Bain Bain Real Estate
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  /40

  $1,250,000

  • 1 Bed
  • 2 Baths
  • 1,056 Sq Ft

  178 Carter Rd, Kent, CT 06757

  Western-facing views from this homestead spanning over 50 acres in Kent. Immerse yourself in nature, where you can hike, mountain bike, cross-country ski, fish, or hunt on your own land! A delightful 1-Bedroom residence boasts an open-concept living and kitchen area that seamlessly transitions to an elevated deck, ideal for enjoying sunset mountain views. Enjoy the home just the way it is, expand

  Liza Reiss Elyse Harney Real Estate

  178 Carter Rd, Kent, CT 06757
• 

  $2,175,000

  Sold Aug 28, 2025

  19 Old Paddock Ln, South Kent, CT 06785

  • 4 Beds
  • 3.5 Baths
  • 3,421 Sq Ft
  • Built 2025

  Last Sold Summary

  • 13% Below List Price
  • $636/SF
  • 76 Days On Market

  Current Estimated Value $1,657,272

  Last Listing Agent Phil Fox William Pitt Sotheby's Int'l

  19 Old Paddock Ln, South Kent, CT 06785
• 

  Est $2,018,145

  Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • 4.5 Baths
  • 3,801 Sq Ft
  • Built 2003

  Unlisted Address

  Last Sold Summary

  • 98 Days On Market

  Last Listing Agent Graham Klemm Klemm Real Estate Inc
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  /36

  $475,000

  • 3 Beds
  • 1 Bath
  • 1,680 Sq Ft

  39 Johnson Rd, Kent, CT 06757

  Charming Country Cottage in the Heart of Kent Tucked away on a peaceful private road just a short walk from the vibrant village of Kent. This charming country cottage offers the perfect blend of privacy, convenience, and classic New England character. Surrounded by picturesque meadows and mountain views and located near the scenic Housatonic River, this home provides a tranquil setting while

  Rebecca Ward William Pitt Sotheby's Int'l

  39 Johnson Rd, Kent, CT 06757
• 

  $410,000

  Sold Sep 15, 2025

  128 S Kent Rd, South Kent, CT 06785

  • 2 Beds
  • 2 Baths
  • 2,480 Sq Ft
  • Built 1955

  Last Sold Summary

  • 18% Below List Price
  • $165/SF
  • 97 Days On Market

  Current Estimated Value $449,545

  Last Listing Agent Dave Fairty E.J. Murphy Realty

  128 S Kent Rd, South Kent, CT 06785
• 

  Est $6,589,215

  Not Listed For Sale

  27 Macedonia Brook Rd, Kent, CT 06757

  • 5 Beds
  • 4.5 Baths
  • 7,632 Sq Ft
  • Built 1827

  27 Macedonia Brook Rd, Kent, CT 06757

  Last Sold Summary

  • 736 Days On Market

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty
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  /40

  $915,000

  • 4 Beds
  • 3 Baths
  • 2,380 Sq Ft

  221 Segar Mountain Rd, Kent, CT 06757

  Beautifully renovated antique colonial on 4.5 private acres with a tumbling brook. Hardwood floors and original beams throughout, two wood- burning fireplaces, custom lighting, original wide-plank floors in some rooms, and a gorgeous, country kitchen with built-in appliances, including a warming drawer. The formal dining room anchors the heart of the home, with a small private study for multiple

  Deborah Bain Bain Real Estate

  221 Segar Mountain Rd, Kent, CT 06757
• 

  $310,000

  Sold Mar 19, 2026

  80 N Main St Unit 2A1, Kent, CT 06757

  • 1 Bed
  • 1 Bath
  • 858 Sq Ft
  • Built 1971

  Last Sold Summary

  • 4% Above List Price
  • $361/SF
  • 36 Days On Market

  Current Estimated Value $306,367

  Last Listing Agent Steve Pener William Pitt Sotheby's Int'l

  80 N Main St Unit 2A1, Kent, CT 06757
• 

  Est $1,270,098

  Not Listed For Sale

  51 Elizabeth St, Kent, CT 06757

  • 4 Beds
  • 3.5 Baths
  • 3,866 Sq Ft
  • Built 2010

  51 Elizabeth St, Kent, CT 06757

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Chris Garrity Bain Real Estate
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  /38

  $1,795,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,950 Sq Ft

  56 Richards Rd, South Kent, CT 06785

  Escape the pace of everyday life and embrace the beauty of country living in this spacious contemporary home, perfectly situated abutting conserved land with exceptional recreational amenities. Offering 4 bedrooms and 3.5 baths, the home features an open-concept floor plan designed for both comfortable living and effortless entertaining. The sunken living room is anchored by an elegant gas

  Stacey Matthews W. Raveis Lifestyles Realty

  56 Richards Rd, South Kent, CT 06785
• 

  $381,000

  Sold Oct 17, 2025

  73 Kent Cornwall Rd, Kent, CT 06757

  • 2 Beds
  • 1 Bath
  • 718 Sq Ft
  • Built 1930

  Last Sold Summary

  • 9% Above List Price
  • $531/SF
  • 37 Days On Market

  Current Estimated Value $390,824

  Last Listing Agent Shannon Tully McGrath Realty Inc.

  73 Kent Cornwall Rd, Kent, CT 06757
• 

  Est $1,229,000

  Not Listed For Sale

  2 Cobble Heights Rd, Kent, CT 06757

  • 4 Beds
  • 4.5 Baths
  • 4,236 Sq Ft
  • Built 1991

  2 Cobble Heights Rd, Kent, CT 06757

  Last Sold Summary

  • 120 Days On Market

  Last Listing Agent William Bolls Compass Connecticut, LLC

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