Windham, CT Homes in ZIP Code 06377

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  /35

  $630,000

  • 3 Beds
  • 3 Baths
  • 1,833 Sq Ft

  245 Snake Meadow Hill Rd, Sterling, CT 06377

  FIRST TIME EVER ON THE MARKET!! Welcome to this incredible one owner owned home! This meticulously maintained private oasis is nothing shy of amazing. This lovely custom built ranch set in a private location yet minutes over the RI line and conveniently located to local amenities. Sitting on over 5.5+ acres of land! This nicely appointed home has 3 bedrooms & 3 full bathrooms. Stunning kitchen

  Skyla Gagnon RE/MAX Bell Park Realty

  245 Snake Meadow Hill Rd, Sterling, CT 06377
• 

  $405,000 Sold Jul 31, 2025

  • 1,612 Sq Ft
  • $251/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  276 Valley View Rd, Sterling, CT 06377

  COUNTRY RANCH w/ POSSIBLE INLAW ($90,000 addition in 2018) w/ BEAUTIFUL LARGE TREX deck for enjoying your evenings on 3.25 PRIVATE acres! MINI SPLITS, GRANITE COUNTERS, stainless appliances, GORGEOUS CUSTOM bathroom w/ TILED GLASS SHOWER and double GRANITE vanity w/ walk in closet next to bedroom w/ slider to deck. 2018 GUTTERS, 2014 NEW SEPTIC, 2019 WELL PUMP, 2018 ROOF, NEW hot water heater and

  Christine Johnson RE/MAX One

  276 Valley View Rd, Sterling, CT 06377
• 

  Est $462,000 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,137 Sq Ft

  6 Courtney Ln, Sterling, CT 06377

  6 Courtney Ln, Sterling, CT 06377
• 

  

  

  /40

  $550,000

  • 3 Beds
  • 3 Baths
  • 2,814 Sq Ft

  271 Snake Meadow Hill Rd, Sterling, CT 06377

  Looking for a custom built home that's set on a peaceful setting? Welcome to this one owner owned home! Located JUST MINUTES OVER the RI line! This private country oasis awaits. This home has it all, including additional & separate living space above the attached 2 car garage. Step food inside this gorgeous home entering through the large mudroom right off the garage which is perfect for New

  Skyla Gagnon RE/MAX Bell Park Realty

  271 Snake Meadow Hill Rd, Sterling, CT 06377
• 

  $610,000 Sold Jul 11, 2025

  • 1,404 Sq Ft
  • $434/SF
  • 10 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2022

  287 N Sterling Rd, Sterling, CT 06377

  Discover single-level living at its finest in this stunning ranch-style home, built in 2022, nestled on just under 40 acres of unique, breathtaking land. Perfect for a horse property, the expansive acreage offers ample space for stables, riding trails, or agricultural pursuits. Outdoor enthusiasts will love the serene Quanduck Brook, feeding the Moosup River on the property-both stocked with

  Daniel Deojay RE/MAX Bell Park Realty

  287 N Sterling Rd, Sterling, CT 06377
• 

  Est $483,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,688 Sq Ft

  239 Valley View Rd, Sterling, CT 06377

  239 Valley View Rd, Sterling, CT 06377
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  /36

  $419,900

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  367 Pine Hill Rd, Sterling, CT 06377

  Charming Ranch House in Tranquil Sterling, CT, welcome to your dream home in a small-town atmosphere! Nestled on a stunning 1.46-acre lot in the picturesque town of Sterling, Connecticut, this beautifully updated ranch house presents an exceptional blend of comfort and modern elegance. Two-bedroom, one-bathroom, updated flooring, newer appliances, perfectly designed for relaxation and nature

  Allen Gammons BHHS Commonwealth/Robert Paul

  367 Pine Hill Rd, Sterling, CT 06377
• 

  $137,500 Sold Jul 09, 2025

  • 1,920 Sq Ft
  • $72/SF
  • 7 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1750

  1100 Plainfield Pike, Sterling, CT 06377

  This home in the heart of Oneco is ready for your vision. Although the home is habitable, it is in need of complete rehab. Recent hot water heater and boiler. Most likely will need to be cash or rehab loan. Property being sold as is, owner will not do any repairs. Property being sold subject to shared driveway and shared well to be recorded prior to closing.

  Paul Stone Kazantzis Real Estate, LLC

  1100 Plainfield Pike, Sterling, CT 06377
• 

  Est $424,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,096 Sq Ft

  562 Sterling Rd, Sterling, CT 06377

  562 Sterling Rd, Sterling, CT 06377
• 

  

  /40

  $449,000

  • 3 Beds
  • 2 Baths
  • 2,467 Sq Ft

  226 Harris Rd, Sterling, CT 06377

  Spacious Raised Ranch with Modern Comforts and Country Charm in Sterling! Welcome to this beautifully expanded 3-bedroom, 2.5-bath raised ranch nestled on over an acre of serene countryside in Sterling. This home offers a perfect blend of comfort, space, and versatility, ideal for those seeking privacy and room to grow. Step inside to find a modern tile kitchen equipped with everything you need

  Coleen Brakenwagen Jason Mitchell Real Estate Connecticut LLC

  226 Harris Rd, Sterling, CT 06377
• 

  $117,500 Sold Jul 09, 2025

  • 720 Sq Ft
  • $163/SF
  • 7 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1948

  1092 Plainfield Pike, Sterling, CT 06377

  2 Bedroom, 1 Full Bath Ranch just a few miles from the Rhode Island line. This home is being sold as is, buyers agents perform your due diligence. Also check out 1100 Plainfield Pike which is also being sold separately (house next door) This home is being sold subject to a shared well and shared driveway agreement to be recorded prior to closing. Listing agent related to seller.

  Paul Stone Kazantzis Real Estate, LLC

  1092 Plainfield Pike, Sterling, CT 06377
• 

  Est $358,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,575 Sq Ft

  527 Saw Mill Hill Rd, Sterling, CT 06377

  527 Saw Mill Hill Rd, Sterling, CT 06377
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  /9

  $419,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,776 Sq Ft

  1 Johns Cir, Sterling, CT 06377

  * NEW CONSTRUCTION * LAST REMINAING LOT* Welcome to Sterling Hills Estates, where luxury meets convenience! This Brand New 2024 to be built Colonial offers the epitome of modern living. With Central Air and Hardwood flooring throughout, this home boasts City water and Sewer for added comfort. Picture yourself in the Gorgeous Granite Kitchen, complete with a view of the valley while you do

  Nicole Maine Lila Delman Compass

  1 Johns Cir, Sterling, CT 06377
• 

  $390,000 Sold Jul 01, 2025

  • 1,184 Sq Ft
  • $329/SF
  • 9 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 2020

  25 Logans Way, Sterling, CT 06377

  Highest and Best Offers by noon on Wednesday May 21. Welcome to this charming 3-bedroom, 2-bathroom home nestled at the end of a peaceful cul-de-sac. Built in 2020, 25 Logans Way offers modern living on a generous 2.49-acre lot, providing privacy and space for outdoor enjoyment. Inside, you'll discover a thoughtfully designed open floor plan that creates a welcoming atmosphere for both everyday

  Pasquale Corso RI Real Estate Services

  25 Logans Way, Sterling, CT 06377
• 

  Est $424,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,254 Sq Ft

  637 Margaret Henry Rd, Sterling, CT 06377

  637 Margaret Henry Rd, Sterling, CT 06377
• 

  

  /9

  $419,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,776 Sq Ft

  1 John's Cir Unit Lot 37, Sterling, CT 06377

  * NEW CONSTRUCTION * Last Remaning Lot *. Welcome to Sterling Hills Estates, where luxury meets convenience! This Brand New 2024 to be built Colonial offers the epitome of modern living. With Central Air and Hardwood flooring throughout, this home boasts City water and Sewer for added comfort. Picture yourself in the Gorgeous Granite Kitchen, complete with a view of the valley while you do

  Patrick Farrell Compass Connecticut, LLC

  1 John's Cir Unit Lot 37, Sterling, CT 06377
• 

  $465,000 Sold Jun 18, 2025

  • 2,558 Sq Ft
  • $182/SF
  • 3 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2000

  13 Woodland Rd, Sterling, CT 06377

  Private Retreat Abutting State Land - 4 Bed, 2.5 Bath on Nearly 4 Acres! Welcome to your own secluded haven in northeast Connecticut! Nestled on nearly 4 acres of pristine land that abuts Connecticut State Forest, this spacious 4-bedroom, 2.5-bathroom home offers the perfect blend of privacy and convenience. Located just minutes from the Rhode Island and Massachusetts state lines, you'll enjoy

  Cynthia Cingranelli-Tagliaferri Priority Real Estate Group,LLC

  13 Woodland Rd, Sterling, CT 06377
• 

  Est $595,223 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,184 Sq Ft

  242 Harris Rd, Sterling, CT 06377

  242 Harris Rd, Sterling, CT 06377
• 

  

  /39

  $499,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,820 Sq Ft

  910 Plainfield Pike, Sterling, CT 06377

  Welcome to 910 Plainfield Pike in charming Sterling, CT right on the RI line.! This beautifully maintained Colonial-style single-family home offers 1,820 sq ft of living space with 6 spacious rooms, including 3 bedrooms, 2 full baths, and a convenient half bath. Situated on a private 1.85-acre lot, the property features a newly paved driveway, two-car garage, and a large farmer's porch-perfect

  Paula Decubellis Re/Max Results

  910 Plainfield Pike, Sterling, CT 06377
• 

  $522,625 Sold Jun 09, 2025

  • 2,046 Sq Ft
  • $255/SF
  • 15 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1996

  350 Pine Hill Rd, Sterling, CT 06377

  Stunning 3-Bed, 2-Bath Post-and-Beam Home on 5.8 Acres with Trails and Privacy. Welcome to this extraordinary 3-bedroom, 2-bathroom home nestled on a tranquil 5.8-acre private lot, offering the perfect combination of seclusion, outdoor adventure, and modern living. This charming post-and-beam home boasts impressive features, including expansive four-wheeler and hiking trails, lush gardens, and a

  Sandy Deignan SD Realty Associates, LLC

  350 Pine Hill Rd, Sterling, CT 06377
• 

  Est $348,936 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,632 Sq Ft

  871 Gibson Hill Rd, Sterling, CT 06377

  871 Gibson Hill Rd, Sterling, CT 06377
• 

  

  /9

  $419,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,776 Sq Ft

  7 Johns Cir Unit Lot 34, Sterling, CT 06377

  * NEW CONSTRUCTION * Welcome to Sterling Hills Estates, where luxury meets convenience! This Brand New 2024 to be built Colonial offers the epitome of modern living. With Central Air and Hardwood flooring throughout, this home boasts City water and Sewer for added comfort. Picture yourself in the Gorgeous Granite Kitchen, complete with a view of the valley while you do dishes! Enjoy the ease of a

  Patrick Farrell Compass Connecticut, LLC

  7 Johns Cir Unit Lot 34, Sterling, CT 06377
• 

  

  /31

  $366,000 Sold May 30, 2025

  • 1,144 Sq Ft
  • $320/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  24 Sterling Ridge Ln, Sterling, CT 06377

  Entered for Comp Purposes

  Nicole Maine Lila Delman Compass

  24 Sterling Ridge Ln, Sterling, CT 06377
• 

  Est $605,000 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 4,524 Sq Ft

  547 Margaret Henry Rd, Sterling, CT 06377

  547 Margaret Henry Rd, Sterling, CT 06377
• 

  

  /29

  $409,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  8 John's Cir Unit Lot 33, Sterling, CT 06377

  * NEW CONSTRUCTION * See MLS 24006016 & 24006028 for additional styles, see plat map attached for available lots. Welcome to Sterling Hills Estates, where luxury meets convenience! This Brand New 2024 to be built Ranch offers the epitome of modern living. With Central Air and Hardwood flooring throughout, this home boasts City water and Sewer for added comfort. Picture yourself in the Gorgeous

  Patrick Farrell Compass Connecticut, LLC

  8 John's Cir Unit Lot 33, Sterling, CT 06377
• 

  $339,900 Sold May 29, 2025

  • 1,144 Sq Ft
  • $297/SF
  • 63 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  24 Sterling Ridge Ln Unit Lot 23, Sterling, CT 06377

  *Can be ready in 45 days or Less * See MLS 24006028 & 24006023 for additional styles, see plat map attached for available lots. Welcome to Sterling Hills Estates, where luxury meets convenience! This Brand New 2024 to be built Raised Ranch offers the epitome of modern living. With Central Air and Hardwood flooring throughout, this home boasts City water and Sewer for added comfort. Picture

  Patrick Farrell Compass Connecticut, LLC

  24 Sterling Ridge Ln Unit Lot 23, Sterling, CT 06377
• 

  Est $340,810 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,864 Sq Ft

  703 Margaret Henry Rd, Sterling, CT 06377

  703 Margaret Henry Rd, Sterling, CT 06377
• 

  

  /30

  $409,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  5 John's Cir Unit Lot 35, Sterling, CT 06377

  New Construction, Sold before print

  Patrick Farrell Compass Connecticut, LLC

  5 John's Cir Unit Lot 35, Sterling, CT 06377
• 

  $279,000 Sold May 27, 2025

  • 1,042 Sq Ft
  • $268/SF
  • 25 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1910

  480 Sterling Rd, Sterling, CT 06377

  Don't miss your chance to make this charming home yours! Nestled in the heart of Sterling, this cozy 3-bedroom, 1-bathroom home offers comfort and convenience. The kitchen flows seamlessly into the dining room and adjoining living room. With easy-to-clean, durable vinyl floors throughout, maintaining the space is a breeze. A custom staircase takes you upstairs to the bedrooms, along with

  Brianna Bienkiewicz Century 21 Guardian Realty

  480 Sterling Rd, Sterling, CT 06377
• 

  Est $301,406 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  119 Saw Mill Hill Rd, Sterling, CT 06377

  119 Saw Mill Hill Rd, Sterling, CT 06377
• 

  

  /9

  $399,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,776 Sq Ft

  3 John's Cir Unit Lot 36, Sterling, CT 06377

  * NEW CONSTRUCTION * See MLS 1355877 & 1355880 for additional styles, see plat map attached for available lots. Welcome to Sterling Hills Estates, where luxury meets convenience! This Brand New 2024 to be built Colonial offers the epitome of modern living in a Planned Unit Development. With Central Air & Hardwood flooring throughout, this home boasts City water & sewer for added comfort. Picture

  Patrick Farrell Compass Connecticut, LLC

  3 John's Cir Unit Lot 36, Sterling, CT 06377
• 

  

  /5

  $399,900 Sold May 16, 2025

  • 1,776 Sq Ft
  • $225/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  30 Sterling Ridge Ln, Sterling, CT 06377

  Entered for Comp Purposes

  Nicole Maine Lila Delman Compass

  30 Sterling Ridge Ln, Sterling, CT 06377
• 

  Est $438,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,512 Sq Ft

  169 Valley View Rd, Sterling, CT 06377

  169 Valley View Rd, Sterling, CT 06377
• 

  /2

  $510,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,707 Sq Ft

  241 Pine Hill Rd, Sterling, CT 06377

  Property has been entered for statistical purposes only.

  Richard Houle HomeSmart Professionals Real Estate

  241 Pine Hill Rd, Sterling, CT 06377
• 

  

  /19

  $375,000 Sold May 16, 2025

  • 1,144 Sq Ft
  • $328/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  26 Sterling Ridge Ln, Sterling, CT 06377

  Entered for Com Purposes

  Nicole Maine Lila Delman Compass

  26 Sterling Ridge Ln, Sterling, CT 06377
• 

  Est $306,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,121 Sq Ft

  1230 Plainfield Pike, Sterling, CT 06377

  1230 Plainfield Pike, Sterling, CT 06377
• 

  

  /40

  $509,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 1,908 Sq Ft

  294 Pine Hill Rd, Sterling, CT 06377

  Nestled on a sprawling 4.58-acre estate, this exquisite 4-bedroom, 2.5-bath contemporary colonial, completed in 1995, offers unparalleled privacy and timeless elegance. Step into a luminous open floor plan where sophistication meets comfort. The gourmet kitchen, a culinary masterpiece, boasts quartz countertops, high-end stainless steel appliances, recessed lighting, abundant storage, a

  Michael Hvizdo Coldwell Banker Realty

  294 Pine Hill Rd, Sterling, CT 06377
• 

  

  /19

  $340,000 Sold May 16, 2025

  • 1,144 Sq Ft
  • $297/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  22 Sterling Ridge Ln, Sterling, CT 06377

  Entered for Comp purposes

  Nicole Maine Lila Delman Compass

  22 Sterling Ridge Ln, Sterling, CT 06377
• 

  Est $362,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,429 Sq Ft

  1154 Plainfield Pike, Sterling, CT 06377

  1154 Plainfield Pike, Sterling, CT 06377
• 

  

  /3

  $85,000

  • Land
  • 1.87 Acres
  • $45,455 per Acre

  18 Ledge Hill Rd, Sterling, CT 06377

  Land was approved for a 3 bedroom home in 2004 - please do your due diligence with the town. Beautiful country lot that is high and dry to build your dream home. 4.5 Miles to 395 and close to RI line. 617Ft of road frontage.

  Christine Johnson RE/MAX One

  18 Ledge Hill Rd, Sterling, CT 06377

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