Windham, CT Homes

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  /40

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,979 Sq Ft

  69 N Bedlam Rd, Chaplin, CT 06235

  Welcome to your Quintessential New England Equestrian Trial Riders Dream property! Featuring a lovingly preserved and updated antique Cape Cod home, a 40x50' newer five-stall barn with heated tack room and workshop located on a country road with almost 6 private acres of picturesque fenced pasture land adjacent to over 200 acres of preserved forest land and trails. Mansfield Hollow State Park is

  

  Tammy Lucier

  eXp Realty

  (860) 553-9423

  69 N Bedlam Rd, Chaplin, CT 06235
• 

  Explore Chaplin

• 

  $442,000 Sold Jul 10, 2025

  • 2,754 Sq Ft
  • $160/SF
  • 6 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1945

  168 Miller Rd, Chaplin, CT 06235

  Stunning 4-Bedroom Colonial with In-Law Apartment on 2.5 Acres - Fully Updated Welcome to this beautifully renovated 4-bedroom, 2-bath colonial offering over 2,700 sq ft of versatile living space, situated on a peaceful and private 2.5-acre lot. Boasting a stunning in-law apartment with its own private entrance and new appliances, this home is ideal for multigenerational living or added rental

  Crystal Gebhardt Coldwell Banker Realty

  168 Miller Rd, Chaplin, CT 06235
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  Est $618,394 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,764 Sq Ft

  119 Ridge Rd, Chaplin, CT 06235

  119 Ridge Rd, Chaplin, CT 06235
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  /36

  $339,900 Open Sun 10AM - 11:30AM

  • 3 Beds
  • 2.5 Baths
  • 2,440 Sq Ft

  52 Singleton Rd, Chaplin, CT 06235

  Welcome to your private retreat in Chaplin! This spacious 3-bedroom, 2-full bathroom ranch is set on just over 5 acres of peaceful, secluded land-perfect for those seeking privacy and a connection to nature. A small pond borders the property, adding charm and tranquility to the setting. The lower level features a large recreational room, ideal for a family room, office, or guest space, plus a

  

  Alexis John

  RE/MAX One

  (860) 846-4680

  52 Singleton Rd, Chaplin, CT 06235
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  $400,000 Sold Jul 03, 2025

  • 1,596 Sq Ft
  • $251/SF
  • 8 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2000

  31 Pumpkin Hill Rd, Chaplin, CT 06235

  Welcome to this beautifully updated 1,596 SF Cape-style home, perfectly situated on 2 peaceful acres along a non-through road. Completely turnkey and move-in ready, this charming 4-bedroom, 2-bath residence blends classic style with modern comfort. The main level offers incredible convenience with two spacious bedrooms, a full bath with laundry, and a stunning brand-new kitchen featuring stylish

  Jared Meehan RE/MAX Bell Park Realty

  31 Pumpkin Hill Rd, Chaplin, CT 06235
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  Est $186,315 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,050 Sq Ft

  257 Willimantic Rd, Chaplin, CT 06235

  257 Willimantic Rd, Chaplin, CT 06235
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  /9

  $149,900

  • 2 Beds
  • 1 Bath
  • 733 Sq Ft

  52 Park Dr, Chaplin, CT 06235

  Remodeled Mobile Home at the End of a Private Road on a Gorgeous 1.25 Acres! Private Level Lot with Two Bedrooms Plus Office!

  Antonio Incontro Countryside Realty

  52 Park Dr, Chaplin, CT 06235
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  $700,000 Sold Jun 27, 2025

  • 2,518 Sq Ft
  • $278/SF
  • 54 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2025

  4 Jackson Ln, Mansfield, CT 06250

  95% COMPLETE. MOVE-IN, IN JUNE to this stunning 4-bedroom, 2.5-bath Colonial which offers an impressive open floor plan with a spacious feeling & easy flow. The foyer welcomes you with French doors leading to a formal study, a spacious coat closet, & a convenient guest bath. The open staircase runs parallel to the entry, adding a unique design touch. Enjoy everyday easy living or entertaining in

  Sheri Shvonski List N Show LLC

  4 Jackson Ln, Mansfield, CT 06250
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  Est $320,607 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  73 Bolduc Ln, Chaplin, CT 06235

  73 Bolduc Ln, Chaplin, CT 06235
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  $384,900 Open Sat 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft

  184 Phoenixville Rd, Chaplin, CT 06235

  A unique blend of old-world charm and modern conveniences. Featuring 3 bedrooms and 2 baths, and 1,848 sqft sitting on 1.3 acres. Perfect for those looking for a piece of history with all the comforts of modern living. New windows, roof, landscaping, large garage, work shop, storage loft, parking for 6+ and more! An outdoor shower and private path straight to one of CT's most beautiful rivers. 2

  Derek Greene Derek Greene

  184 Phoenixville Rd, Chaplin, CT 06235
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  $335,000 Sold Jun 20, 2025

  • 1,388 Sq Ft
  • $241/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1954

  5 Chappell St, Chaplin, CT 06235

  This is the one - almost completely updated - turn key house ready for you! Almost 1400 sq ft, newly painted, refinished hard wood floors, brand new stainless steel appliances, Large living room with fireplace. Main level has full bath, 3 bedrooms with additional master bath. Bonus - heated finished basement with another half bath! Great for man cave, kids playroom etc. Large corner lot, level

  Glenn Stavens Aspen Realty Group

  5 Chappell St, Chaplin, CT 06235
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  Est $485,233 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,080 Sq Ft

  128 S Bear Hill Rd, Chaplin, CT 06235

  128 S Bear Hill Rd, Chaplin, CT 06235
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  /2

  $45,000

  • Land
  • 1.50 Acres
  • $30,000 per Acre

  284 Willimantic Rd, Chaplin, CT 06235

  Build your dream home on this approved 1.5-acre lot.

  Lisa Sader-Goede Aspen Realty Group

  284 Willimantic Rd, Chaplin, CT 06235
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  $360,000 Sold Jun 05, 2025

  • 1,282 Sq Ft
  • $281/SF
  • 26 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1951

  108 S Bedlam Rd, Chaplin, CT 06235

  Welcome to this quaint colonial home full of charm and updates. The interior has been fully remodeled over recent years. The warmth of the refinished hardwood floors, neutral color palette & flat ceilings give this home a sense of calm & tranquility. There are built-ins throughout the 1st floor in each room. The living room has a newer picture window, built-in shelves & a fireplace that once had

  Lindsey L. Niarhakos RE/MAX One

  108 S Bedlam Rd, Chaplin, CT 06235
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  Est $529,390 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  90 N Bedlam Rd, Chaplin, CT 06235

  90 N Bedlam Rd, Chaplin, CT 06235
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  /6

  $242,000

  • 2 Beds
  • 1 Bath
  • 928 Sq Ft

  Unlisted Address

  House, garage and 3 additional lots being sold as 1-sale. House is in very poor condition and not livable as it sits. Total acres are 19.46. Do not access the house without permission! Driveway turn around is available, do not proceed to last house's driveway!

  Roberta Cardinal RbRE, LLC

  Unlisted Address
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  $300,000 Sold May 12, 2025

  • 1,200 Sq Ft
  • $250/SF
  • 114 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1990

  114 Lynch Rd, Chaplin, CT 06235

  Step up onto the farmers porch, open the door to a true log home set back off the road on lightly wooded land with endless possibilities! This three bedroom home has wood beams and hardwood floors throughout! The stone fireplace in the living room with vaulted beamed ceilings creates a cozy room to enjoy! There's a room off the back that's framed in and ready to be finished. *** Back on the

  Nancy Bard Bard Real Estate, LLC

  114 Lynch Rd, Chaplin, CT 06235
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  Est $270,382 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,280 Sq Ft

  89 Chewink Rd, Chaplin, CT 06235

  89 Chewink Rd, Chaplin, CT 06235
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  /34

  $499,900

  • 2 Beds
  • 1.5 Baths
  • 2,954 Sq Ft

  192 Palmer Rd, Chaplin, CT 06235

  Tucked away at the end of a long, private driveway, this sprawling 2-bedroom ranch offers the ultimate in privacy and tranquility. Set on a picturesque 4-acre lot surrounded by nature, this home is perfect for those seeking a peaceful retreat with room to roam. Inside, you'll find a spacious and flexible floor plan with generous living areas, large windows that bring the outdoors in, and the ease

  Lisa Barstow Simply Sold Real Estate

  192 Palmer Rd, Chaplin, CT 06235
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  $315,000 Sold Apr 10, 2025

  • 1,924 Sq Ft
  • $164/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  46 Miller Rd, Chaplin, CT 06235

  This home has so much to offer, definitely, a must see! This Three-bedroom home has a great open floor plan with tons of natural lighting. The back wall is full of windows, wood beams and French doors that lead to a sizeable deck that overlooks your private backyard retreat. A short walk brings you to the large in-ground pool.

  Team DAnna Statewide Premier Prop. LLC

  46 Miller Rd, Chaplin, CT 06235
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  Est $307,821 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  304 S Bear Hill Rd, Chaplin, CT 06235

  304 S Bear Hill Rd, Chaplin, CT 06235
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  /2

  $139,000 Pending

  • Land
  • 12 Acres
  • $11,488 per Acre

  0 Hampton Rd Unit 170523717, Chaplin, CT 06235

  12.1 acre lot with frontage on Route 6 and Cross Road. Button Ball Brook runs through property. Could be a great home site, or potential commercial development with zone change. Rolling hills of gravel, mostly wooded.

  David Mieczynski National Realty Advisors LLC

  0 Hampton Rd Unit 170523717, Chaplin, CT 06235
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  $349,900 Sold Feb 14, 2025

  • 1,220 Sq Ft
  • $287/SF
  • 35 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1952

  60 Scotland Rd, Chaplin, CT 06235

  Fully updated ranch just freshly painted and hardwood floors refinish and is move in ready. This home sits on an one acre lot with a fenced in backyard ready for your pets. Everything has been updated in the past 12 years roof,vinyl siding,gutters,doors,garage doors,well tank and pump,water heater,electrical panel with generator hook up,septic tank and so much more. plenty of parking and

  Derek Greene Derek Greene

  60 Scotland Rd, Chaplin, CT 06235
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  Est $281,941 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  8 Chappell Street Extension, Chaplin, CT 06235

  8 Chappell Street Extension, Chaplin, CT 06235
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  /33

  $510,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,638 Sq Ft

  6 S Bear Hill Rd, Chaplin, CT 06235

  Welcome to Chaplin! Custom Built Ranch on 2.12 acres has 3 Bedrooms, 2 Full Bathrooms, Home Office, and First Floor Laundry. Large Open Floor Plan for the Family Room and Kitchen with Granite Countertops and Hardwood Floors. Primary Bedroom has Private Bath and Walk-in Closet. Central Air, Covered Front Porch, Deck, Large Walk-Out Basement, and 2 Car Attached Garage. Located on a quiet country

  Mary Ann Bohonowicz Berkshire Hathaway NE Prop.

  6 S Bear Hill Rd, Chaplin, CT 06235
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  $453,000 Sold Jan 22, 2025

  • 2,650 Sq Ft
  • $171/SF
  • 4 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2024

  260 Phoenixville Rd, Chaplin, CT 06235

  Beautiful Custom Ranch to be Built on Level Lot! Finished Basement! Whole House Generator! Fireplace! Front Porch! A Must See! New price with extras is $453,000.00

  Cathyann Schulte Countryside Realty

  260 Phoenixville Rd, Chaplin, CT 06235
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  Est $417,102 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,856 Sq Ft

  515 Tower Hill Rd, Chaplin, CT 06235

  515 Tower Hill Rd, Chaplin, CT 06235
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  /35

  $339,500 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,444 Sq Ft

  108 Federal Rd, Chaplin, CT 06235

  Great 3 bedroom home set on a private 3.99 acres! This home has so much to offer. As you enter into the fireplaced living room you'll notice the beautiful Brazilian teak hardwood floors that continue through the recently updated kitchen and into the large sun-filled great room. The kitchen features granite countertops, stainless steel appliances and plenty of of cabinet space. Off the kitchen is

  Kathleen Holland KW Legacy Partners

  108 Federal Rd, Chaplin, CT 06235
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  /30

  $340,000 Sold Jan 16, 2025

  • 1,584 Sq Ft
  • $215/SF
  • 6 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1992

  242 Tower Hill Rd, Chaplin, CT 06235

  Escape to the tranquility of this adorable cape nestled on over 3 acres of picturesque countryside. The current owners, in the last three years have installed a new furnace, well tank/well pump, septic riser, mini splits, a shed, updated the bath and added new flooring in the kitchen and some appliances. Perfect for nature lovers, with plenty of space to relax and unwind. The heated bonus room

  Valerie MacNeil Kazantzis Real Estate, LLC

  242 Tower Hill Rd, Chaplin, CT 06235
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  Est $283,897 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,413 Sq Ft

  128 Willimantic Rd, Chaplin, CT 06235

  128 Willimantic Rd, Chaplin, CT 06235
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  /40

  $420,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,726 Sq Ft

  5 Chaplin St, Chaplin, CT 06235

  Amazing opportunity to own this charming 1800's antique Colonial farmhouse, blending timeless character with modern updates, set on a beautiful, level 6.06-acre lot in a peaceful historic district. Offering 2,726 sq ft of living space, this serene property features two horse stalls, perfect for equestrian lovers or those simply seeking open space and quiet countryside living. Inside, you'll find

  Oz Pariser Premier Re Group LLC

  5 Chaplin St, Chaplin, CT 06235
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  $250,000 Sold Jan 16, 2025

  • 1,280 Sq Ft
  • $195/SF
  • 66 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1938

  775 Phoenixville Rd, Chaplin, CT 06235

  Welcome Home! Set on nearly 5 picturesque acres in the historic town of Chaplin, this property invites you to embrace the quintessential New England lifestyle. Nestled in a peaceful, wooded setting yet close to state parks, orchards, and farms, it gives the ideal balance of privacy and natural beauty. The main level exudes charm, featuring an open floor plan with a cozy dining area, a welcoming

  Patricia Martin Coldwell Banker Realty

  775 Phoenixville Rd, Chaplin, CT 06235
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  Est $439,219 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 1,950 Sq Ft

  10 Davis Rd, Chaplin, CT 06235

  10 Davis Rd, Chaplin, CT 06235
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  $369,000 Sold Dec 02, 2024

  • 1,892 Sq Ft
  • $195/SF
  • 20 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1910

  350 Phoenixville Rd, Chaplin, CT 06235

  Welcome to this beautifully renovated historic gem, once known as the Chaplin Grange! This exceptional property seamlessly blends classic charm with modern amenities, offering a unique living experience. Step inside to discover an expansive open-concept living space where the living room and kitchen flow effortlessly together, perfect for both relaxing and entertaining. The kitchen boasts

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  350 Phoenixville Rd, Chaplin, CT 06235
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  Est $380,273 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,814 Sq Ft

  3 Pumpkin Hill Rd, Chaplin, CT 06235

  3 Pumpkin Hill Rd, Chaplin, CT 06235
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  $353,000 Sold Oct 11, 2024

  • 960 Sq Ft
  • $368/SF
  • 27 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1990

  12 Mountain Laurel Ln, Chaplin, CT 06235

  Charming 3-Bedroom Ranch with Expansive Grounds, Privacy, New Appliances, and Hardwood Floors!! Nestled on a 5-acre estate surrounded by peaceful woods, this charming 3-bedroom, 1-bath ranch provides tranquil country living with modern conveniences. Built in 1990, the home spans 960 square feet and includes a walk-out basement with room for future expansion. Key Features: **Secluded Setting:

  Honglian Wu Home Selling Team

  12 Mountain Laurel Ln, Chaplin, CT 06235
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  Est $328,426 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft

  200 Phoenixville Rd, Chaplin, CT 06235

  200 Phoenixville Rd, Chaplin, CT 06235
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  $335,000 Sold Oct 11, 2024

  • 2,090 Sq Ft
  • $160/SF
  • 16 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1960

  9 Ridge Rd, Chaplin, CT 06235

  This ranch home with a fully finished walkout lower level with an apartment can meet a variety of living needs. Whether you are looking for one-level living, need an in-law set up, or desire to have an income producing unit...there is lots of potential! The 2-car garage is attached by a covered breezeway. The eat-in kitchen has new beautiful wood butcher block countertops and a white farmhouse

  Lindsey L. Niarhakos RE/MAX One

  9 Ridge Rd, Chaplin, CT 06235
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  Est $342,388 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 660 Sq Ft

  416 Hampton Rd, Chaplin, CT 06235

  416 Hampton Rd, Chaplin, CT 06235
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  $317,500 Sold Oct 04, 2024

  • 1,180 Sq Ft
  • $269/SF
  • 9 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1951

  36 Nollett Rd, Chaplin, CT 06250

  This cozy cape includes a large private lot, just under three acres, surrounded by woods. The home itself gives the perfect blend of comfort and space with 2 bedrooms, one full bathroom, and a newly renovated second floor. Second floor space would be a great opportunity for a large primary bedroom, possible office space, or family room. Enjoy the tranquility of country living with the convenience

  Rachel Mooney Naples Realty Group, LLC

  36 Nollett Rd, Chaplin, CT 06250

Showing Results 1 - 40, Page 1 of 18