Windham County CT Homes for Sale

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  /13

  $799,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,900 Sq Ft

  36 Olde Meadow Rd, Woodstock, CT 06281

  TO BE CONSTRUCTED | Starting at $799,900 Welcome to Eastwood Estates, where luxury living meets the natural beauty and tranquility of Woodstock. Set on a picturesque 1.92-acre homesite bordering protected open space and framed by classic New England stone walls, this offering provides a rare opportunity to BUILD a custom home in one of the area's most desirable neighborhoods. Partner with an

  

  Tina Lajoie

  Signature Properties of New England

  36 Olde Meadow Rd, Woodstock, CT 06281
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  /38

  $429,557

  • 4 Beds
  • 2 Baths
  • 2,375 Sq Ft

  55 Mechanics St, Putnam, CT 06260

  Step into a world of timeless beauty and refined New England charm in this extraordinary 1922 Antique Colonial Victorian, perfectly nestled in the heart of Putnam, Connecticut. Rich with character, elegance, and architectural detail, this remarkable residence beautifully blends historic sophistication with thoughtful modern updates. From the moment you enter, you are welcomed by an absolutely

  Lisa Therecka Therecka & Associates LLC

  55 Mechanics St, Putnam, CT 06260
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  /40

  $1,995,000

  $505K PRICE DROP

  • Land
  • 153.1 Acres
  • $13,031 per Acre

  317 Bebbington Rd, Ashford, CT 06278

  CROOKES ORCHARD - A LEGACY FARM OF EXTRAORDINARY BEAUTY AND OPPORTUNITY! One of Northeast Connecticut's most beloved agricultural destinations, presents an exceptionally rare opportunity to acquire 153 contiguous acres of working orchard, farmland, & scenic countryside. The property encompasses approximately 32 acres of improved cropland w/sprawling hay fields, picturesque ponds, & Bebbington

  Kiara Rusconi William Raveis Real Estate

  317 Bebbington Rd, Ashford, CT 06278
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  /40

  $699,900

  • 5 Beds
  • 4 Baths
  • 3,018 Sq Ft

  1530 Hartford Pike, Killingly, CT 06243

  Step back in time while enjoying the comforts of today at this remarkable circa-1770 property, where timeless New England charm meets modern convenience. Set on nearly 4 private acres, this one-of-a-kind estate offers endless possibilities for multi-generational living, rental income, a hobby farm, or the perfect retreat. The beautifully maintained main residence showcases the character and

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  1530 Hartford Pike, Killingly, CT 06243
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  /20

  $325,000

  $25K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,998 Sq Ft

  70 Walnut St, Putnam, CT 06260

  Charming Victorian 2-family set up high and framed by a classic stone wall, situated on a spacious .45-acre lot and fully occupied with strong cash flow from day one. Both tenants are in yearly leases, providing stability and consistent income, and each unit features separate utilities with individual boilers, with tenants paying their own heat and electric to help maximize returns. The

  Tyrone Murphy REMAX Revolution

  70 Walnut St, Putnam, CT 06260
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  /23

  $267,000

  $53K PRICE DROP

  • 6 Beds
  • 2 Baths
  • 1,904 Sq Ft

  144 Prospect Ave, Danielson, CT 06239

  Price Improved.... Seller says Sell Sell Sell.. Looking for your next investment property?? Look no further. This home has been under agreement several times, but not because of inspection issues- the previous transactions couldn't move forward due to owner- occupied requirements from the solar. If you been searching for a home that's move in ready, while allowing you to update it at your own

  KAREN MILHEM Media Realty Group, Inc.

  144 Prospect Ave, Danielson, CT 06239
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  /35

  $599,000

  • 5 Beds
  • 4 Baths
  • 2,220 Sq Ft

  21 Linkkila Ln, Chaplin, CT 06235

  Private Country Retreat with In-Law Suite on Nearly 4 Acres. Welcome to 21 Linkkila Lane in Chaplin, Windham County, Connecticut-a beautifully updated log home offering exceptional privacy, flexible living space, and modern upgrades on nearly four picturesque acres. The main residence features three spacious bedrooms and three full bathrooms, highlighted by an extensively renovated kitchen,

  Derek Greene Derek Greene

  21 Linkkila Ln, Chaplin, CT 06235
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  /2

  $179,000

  • Land
  • 3.29 Acres
  • $54,407 per Acre

  0 Child Dome Rd Unit 24183833, Woodstock, CT 06281

  Rare opportunity to own a large tract of land in Woodstock, CT. This stunning location is one of the highest points in Woodstock. Surrounded by conservatory farmland, the views are for miles. The ride to this property, through the sparsely populated countryside, will surely give you the feel of the natural surroundings. Although located "far from the crowd" you are centrally located to Hartford,

  Bob Seele Coldwell Banker Realty

  0 Child Dome Rd Unit 24183833, Woodstock, CT 06281
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  /38

  $359,000

  Open House 8/08 $16K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 864 Sq Ft

  70 Hawkins Rd, Woodstock Valley, CT 06282

  Welcome to this charming 2-bedroom, 1.5-bath home that offers the perfect blend of comfort and convenience. Ideal for empty nesters, downsizers, or anyone looking for a fantastic condo alternative, this home provides the privacy of single-family living without the hassle HOA. Step inside and enjoy a warm and inviting layout with comfortable living spaces that make the home feel instantly

  Joyce Teixeira Dream Living Realty, LLC

  70 Hawkins Rd, Woodstock Valley, CT 06282
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  /29

  $579,900

  Open Sun 11AM - 1PM Coming Soon

  • 3 Beds
  • 2 Baths
  • 2,327 Sq Ft

  305 Fox Rd, Putnam, CT 06260

  Pristine 1998 Contemporary Cape, situated on 4.62 private and peaceful acres. Built to modern standards, pairing turn-of-the-millennium construction efficiency with a rare, spacious acreage footprint. Modern kitchen features granite countertops, eat-in and island seating, and access to a newly remodeled (2023) Wolf composite deck. The high-quality deck material contains no wood fillers, making it

  Debra Burns Berkshire Hathaway NE Prop.

  305 Fox Rd, Putnam, CT 06260
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  /2

  $200,000

  $50K PRICE DROP

  • Land
  • 34,848 Sq Ft
  • $250,000 per Acre

  35 S Main St, Brooklyn, CT 06234

  Bring your ideas for this commercial lot, centrally located in a high traffic area located right off route 6. Was previously approved for a 4800 sq.ft. retail/office building with two cutouts as an entrance/exit. Several options for commercial use such as retail shopping, office space, farmers market, restaurant, and more in the zoning regulations.

  Andrew Kausch Kazantzis Real Estate, LLC

  35 S Main St, Brooklyn, CT 06234
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  /8

  $594,900

  New Construction

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

  14 Hnath Rd, Ashford, CT 06278

  To Be Built in Ashford Meadow Estates is this stunning Custom Modern Farmhouse Ranch with Optional In-Law design. 4, 1 acre lots to choose from in Ashford's Newest 6 lot subdivision featuring picturesque land in Eastern CT's quiet corner, Bold & Elegant with striking exterior finish options like timber frame porch accents, board & batten siding, metal roof accents & black Andersen windows. An

  Mark Massaro Coldwell Banker Realty

  14 Hnath Rd, Ashford, CT 06278
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  /21

  $135,000

  • 2 Beds
  • 1 Bath
  • 1,063 Sq Ft

  34 Providence Rd, Brooklyn, CT 06234

  Offer deadline Monday 8/3 noon. Subject to Probate approval. CASH only. Conveying with contents of home. Car will be removed. Home has been occupied until recently. A rare chance to own and restore an original schoolhouse filled with historic charm and architectural character. Whether you're an investor, renovator, or preservation enthusiast, this property offers tremendous upside potential.

  Kristin DeMarco Coldwell Banker Realty

  34 Providence Rd, Brooklyn, CT 06234
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  /30

  $329,900

  $5K PRICE DROP

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

  74 Perry St Unit 183, Putnam, CT 06260

  Welcome to easy, low-maintenance condo living in the heart of Putnam! This well-appointed 2-bedroom, 1.5-bath home offers a bright and inviting main level featuring a sun-filled living room with beautiful hardwood floors and direct access to a private wood deck-perfect for seamless indoor/outdoor living. The kitchen is designed for both function and comfort, complete with a dining area, pantry

  Genevieve Botelho Lamacchia Realty

  74 Perry St Unit 183, Putnam, CT 06260
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  /34

  $339,900

  • 5 Beds
  • 2 Baths
  • 2,576 Sq Ft

  9 Carey Ave, Plainfield, CT 06374

  Welcome to 9 Carey Avenue in Plainfield, Connecticut, a spacious 5-bedroom legal two-family home currently being enjoyed by family members as a single-family residence with a private in-law apartment. Whether you're looking for a home for multi-generational living, an owner-occupied investment, or simply extra space for extended family or guests, this versatile property offers endless

  My Greene Team Keller Williams Leading Edge

  9 Carey Ave, Plainfield, CT 06374
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  /36

  $429,900

  $20K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 2,887 Sq Ft

  13 Bates Rd, Chaplin, CT 06235

  Spacious farmhouse living at its best! This charming 5-bedroom, 2 full bath, and 1 half bath home sits on an expansive 11 acres, offering endless possibilities for privacy, recreation, or hobby farming. Inside, you'll find hardwood flooring throughout and two cozy fireplaces that add warmth and character. The versatile layout includes two additional family rooms that could easily serve as extra

  Kristen Merrill Countryside Realty

  13 Bates Rd, Chaplin, CT 06235
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  /28

  $309,900

  • 4 Beds
  • 1.5 Baths
  • 1,320 Sq Ft

  30 Russ Rd, Willimantic, CT 06226

  Affordable & Move-in ready 4-bedroom, 1.5-bath Cape offering over 1,300 sq. ft. of comfortable living space, with potential to add more sqft in the semi-finished basement. Conveniently located near shopping, dining, and everyday amenities, as well as Eastern Connecticut State University and the University of Connecticut. Eligible for USDA financing, making homeownership more accessible for

  Viviana Penson-Rodriguez Leaf Realty Group, LLC

  30 Russ Rd, Willimantic, CT 06226
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  /36

  $699,900

  • 3 Beds
  • 2.5 Baths
  • 2,412 Sq Ft

  104 Hanover Rd, Canterbury, CT 06331

  Experience the perfect blend of timeless charm and upscale finishes in this nearly brand new* custom home. Best of all, there's still time to select some of the finishing touches and make this home uniquely yours. Designed with everyday living and entertaining in mind, this exceptional home offers 3 bedrooms, 2.5 baths, plus a versatile flex room ideal for a home office, fitness room, playroom,

  Cynthia Cingranelli-Tagliaferri Priority Real Estate Group,LLC

  104 Hanover Rd, Canterbury, CT 06331
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  /3

  $480,000

  New Construction

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  10 Indian Run Dr, Thompson, CT 06277

  Brand new construction offering easy, modern living! This thoughtfully designed home features 2 bedrooms and 2 full bathrooms with a bright, open floor plan perfect for today's lifestyle. The spacious kitchen showcases a center island, ideal for entertaining, and flows seamlessly into the living and dining areas. Enjoy an abundance of natural light from the many windows throughout. The primary

  Cary Marcoux RE/MAX Bell Park Realty

  10 Indian Run Dr, Thompson, CT 06277
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  /37

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,941 Sq Ft

  26 Old Putnam Road Extension, Danielson, CT 06239

  Welcome to 26 Old Putnam Road Extension, Plainfield-an impeccably maintained raised ranch offering nearly 2,000 square feet of finished living space in a quiet, convenient location. The bright, open-concept main level features a soaring vaulted ceiling, hardwood flooring, and abundant natural light. The updated kitchen boasts brand-new quartz countertops, newer appliances, and flows seamlessly

  Jennifer Mahr RE/MAX Bell Park Realty

  26 Old Putnam Road Extension, Danielson, CT 06239
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  /39

  $630,000

  Open Sun 11AM - 1PM

  • 3 Beds
  • 3 Baths
  • 3,340 Sq Ft

  373 Chase Rd, Thompson, CT 06277

  Welcome to your private, beautifully landscaped retreat in Thompson. This meticulous colonial offers generous space inside and out, featuring a stunning granitetopped kitchen with undercabinet lighting, JennAir cooktop, cabinetpacked storage, and a slider leading to the Trex deck. The open layout flows into a bright living room with a large island, plus a charming dining room and a cozy family

  Michelle Fanion Century 21 North East

  373 Chase Rd, Thompson, CT 06277
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  /8

  $300,000

  • 6 Beds
  • 2 Baths
  • 2,794 Sq Ft

  9 Providence St, Putnam, CT 06260

  OVERSIZED 2 car garage you could rent out for ADDITIONAL income! Paved driveway w/ plenty of parking, city water, sewer, city gas, it is vinyl sided and replacement windows and service upgrade according to field card. Estate Sale. 3 bedrooms EACH unit they each have their own laundry hook ups and covered porches and a backyard to enjoy. Estate owns the refrigerator and stove in each unit

  Christine Johnson RE/MAX One

  9 Providence St, Putnam, CT 06260
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  /39

  $529,900

  $20K PRICE DROP

  • 7 Beds
  • 3 Baths
  • 3,071 Sq Ft

  110 Church St, Putnam, CT 06260

  Welcome to the Albert C. Luke home in the heart of Putnam. This Queen Anne Victorian home has been well maintained. It's everything you'd expect in a restored Victorian home. Beautiful wood flooring, build-ins, four fireplaces all with custom carved mantels, and an updated kitchen that's modern with quartz countertops and a marble backsplash, while complimenting the era of the home. The first

  Jennifer Jones Premeer Real Estate Inc.

  110 Church St, Putnam, CT 06260
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  /2

  $400,000

  • Land
  • 3.2 Acres
  • $125,000 per Acre

  0 Putnam Rd Unit 24147722, Plainfield, CT 06332

  3.2 corner lot located at the Wauregan four corners. Currently zoned residential but has commercial potential. Buyer's and buyers agent to do all of your own due diligence with the town.

  Cary Marcoux RE/MAX Bell Park Realty

  0 Putnam Rd Unit 24147722, Plainfield, CT 06332
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  /40

  $699,000

  • 4 Beds
  • 2.5 Baths
  • 2,634 Sq Ft

  272 Horse Hill Rd, Ashford, CT 06278

  Nestled at the end of a long, winding driveway, this exquisite Colonial home offers timeless New England elegance on over three private, picturesque acres. Surrounded by classic stone walls, sprawling lawns, mature gardens, and inviting outdoor dining spaces, this exceptional property is a secluded retreat rich in historic details and charm. Inside, you'll find four spacious bedrooms with one on

  Jay Kelly William Raveis Real Estate

  272 Horse Hill Rd, Ashford, CT 06278
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  /29

  $165,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 848 Sq Ft

  96 Canterbury Rd Unit B, Plainfield, CT 06374

  Move right in to this charming 2-bedroom, 1-bath townhouse-style condominium. This inviting home features a bright and spacious living area and an eat in fully applianced kitchen & brand new carpeting throughout. The second level houses the full bathroom and two bedrooms. Enjoy low-maintenance living with the condo fee covering grounds maintenance, snow removal, trash pickup & water/sewer. The

  Lisa Gervais Team Bassett Realty LLC

  96 Canterbury Rd Unit B, Plainfield, CT 06374
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  /40

  $850,000

  $145K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 5,176 Sq Ft

  82 Kennerson Reservoir Rd, Eastford, CT 06242

  Experience exceptional waterfront living overlooking the beautiful 88-acre Kennerson Reservoir in scenic Eastford. This impressive 4-bedroom, 3-bath home offers breathtaking panoramic water views and the perfect blend of comfort and recreation. Enjoy kayaking, fishing, boating, swimming, and access to a shared beach.The main level features approximately 2,690 sq ft of living space, plus an

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  82 Kennerson Reservoir Rd, Eastford, CT 06242
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  /2

  $49,900

  • Land
  • 32,670 Sq Ft
  • $66,533 per Acre

  463 Mashamoquet Rd, Pomfret, CT 06259

  Raw land, situated at the corner of a state route and residential road. This desirable site in the heart of the quiet corner could be your next retreat!! The zoning RR is suitable for many rural residential uses. The .75 acre lot located on route 44 has a lovely babbling brook running along the side. Positioned parallel to the airline trail, this could be the BEST private camping site offering

  Robyn Letourneau Berkshire Hathaway NE Prop.

  463 Mashamoquet Rd, Pomfret, CT 06259
• 

  

  /3

  $179,000

  • Land
  • 2.9 Acres
  • $61,724 per Acre

  0 Child Dome Rd Unit 24183838, Woodstock, CT 06281

  Rare opportunity to own a large buildable lot in Woodstock, CT. This serene rear lot is located on one of the highest elevations in Woodstock. Surrounded by conservatory farmland, the views are for miles. The ride to this property, through the sparsely populated countryside, will surely give you the feel of the natural surroundings. Although located "far from the crowd" you are centrally located

  Bob Seele Coldwell Banker Realty

  0 Child Dome Rd Unit 24183838, Woodstock, CT 06281
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  /4

  $74,900

  $10K PRICE DROP

  • Land
  • 21,780 Sq Ft
  • $149,800 per Acre

  0 Baxter Rd Unit 24177023, Woodstock, CT 06281

  Build your dream home near the lake! This unique offering includes two adjoining parcels being sold together for a combined total of approximately 0.7 acres. The primary 0.5-acre parcel features a beautiful cleared and level homesite with open grassy space, ideal for new construction. Previous perc testing and a site development plan in 2008 outlines proposed home placement, septic system, and

  Donna Bertram Signature Properties of N.E.

  0 Baxter Rd Unit 24177023, Woodstock, CT 06281
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  /19

  $45,000

  $15K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 672 Sq Ft

  17 Wayne Dr, North Windham, CT 06256

  This is a well maintained, 1972, 2 Bedroom Bath and a half unit that has numerous updates that include updated kitchen and full bath, and replacement windows. There is enclosed porch, central air and large storage shed. There are some furnishings that can be included. Close to shopping, medical facilities and outdoor attractions. Park residence approval is required. the lot is $769 a month. This

  Clarence Russ Home Selling Team

  17 Wayne Dr, North Windham, CT 06256
• 

  /2

  $79,000

  $20K PRICE DROP

  • Land
  • 2.6 Acres
  • $30,385 per Acre

  106 Church St, Brooklyn, CT 06234

  Approved building lot on desirable street. Property is on a shared driveway.

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  106 Church St, Brooklyn, CT 06234
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  /22

  $424,900

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,524 Sq Ft

  44 Richmond Rd, Putnam, CT 06260

  Welcome to this totally re-built ranch done with new homeowners in mind. This home has been taken down to the studs and had the floor plan redesigned and put back together with brand new everything. The home features a very open and bright floor plan for the kitchen, dining, and living room space. The main level has two very good-sized rooms with the primary having its own bath with main level

  David White OwnerEntry.com

  44 Richmond Rd, Putnam, CT 06260
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  /2

  $180,000

  • Land
  • 17.36 Acres
  • $10,369 per Acre

  0 Boston Turnpike, Eastford, CT 06242

  17.3 wooded acres in a rural Eastford location right on Route 244. The property features a stone wall and ample space to build your dream home. Quiet setting, convenient to nearby towns and amenities. A great opportunity to build in a peaceful country area.

  Nicole Gleason CR Premier Properties

  0 Boston Turnpike, Eastford, CT 06242
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  /30

  $579,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,970 Sq Ft

  186 Brickyard Rd, Woodstock, CT 06281

  Enjoy the beautiful landscaping of this custom oversized ranch. Located on 6 acres, Recently cleared, private back yard perfect for entertaining, recreation and maybe a chicken or two. Double deck off the kitchen, that leads to above ground pool. This is your perfect summer spot! Kitchen with breakfast nook updated cabinets and stainless appliances, tile... Dining room follows kitchen to a one

  Amy Vinal Pine Knoll Real Estate

  186 Brickyard Rd, Woodstock, CT 06281
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  /2

  $750,000

  $450K PRICE DROP

  • Land
  • 19.37 Acres
  • $38,720 per Acre

  38-82 Ballouville Rd, Killingly, CT 06241

  41 lot approved sub-division (detached single family units). Town water & sewer reserved for project. Close to I-395 and Route 12. Total of 19.37 acres. For Sale $750,000. DIRECTIONS: I-395 S Exit 43. Turn left on Attawaugan Crossing Rd. Go straight on Ballouville Rd. Just past Church St. on left. I-395 N Exit 43. Turn right on Attawaugan Crossing Rd. Go straight on Ballouville Rd. Just past

  Norm Peck Signature Properties of N.E.

  38-82 Ballouville Rd, Killingly, CT 06241
• 

  

  /12

  $215,000

  $10K PRICE DROP

  • Land
  • 1.34 Acres
  • $160,448 per Acre

  115 Groveland Ave, Putnam, CT 06260

  Development Opportunity! Town-approved condominium project with fully engineered plans available by request, set on a private lot with views. This offering conveys development rights only for an approved condominium complex consisting of two existing townhouses and approvals for eight additional units to be built. Prior approvals are in place with the Town, underground utilities are on site, and

  Jennie Kesselman Berkshire Hathaway NE Prop.

  115 Groveland Ave, Putnam, CT 06260
• 

  

  /30

  $899,900

  • 4 Beds
  • 2.5 Baths
  • 2,982 Sq Ft

  233 Fire Tower Rd, Pomfret Center, CT 06259

  56 expansive ACRES of pristine Connecticut COUNTRYSIDE with quiet rural atmosphere. Space for HUNTING wildlife viewing and trails. Recreational Haven, Homestead with enough room for FARMING and timber. ENORMOUS 2400 square-foot GARAGE/WORKSHOP with 12 x 12 doors HEATED with two zones, office with a full bathroom and additional bathroom and its OWN Septic! DETACHED two car garage with (two NEW

  Christine Johnson RE/MAX One

  233 Fire Tower Rd, Pomfret Center, CT 06259
• 

  

  /29

  $439,900

  Open Sat 11AM - 1PM

  • 5 Beds
  • 2.5 Baths
  • 4,063 Sq Ft

  37 van Den Noort St, Putnam, CT 06260

  NEED PLENTY OF SPACE? YOU'LL FIND IT HARD TO FILL UP THIS HOME! OVER 4000 SQUARE FEET OF WELL CARED FOR LIVING AREA ON 3 FLOORS. BEAUTIFUL HARDWOOD FLOORS IN LR, HUGE EAT-IN KITCHEN, 5 TO 6 BEDROOMS AND A BATH ON EACH LEVEL. LOWER LEVEL FAMILY/GAME ROOM WITH WET BAR, RECREATION ROOM, AND MASSIVE MEDIA ROOM WHICH HAD BEEN USED FOR A PROFESSIONAL PHOTOGRAPHY STUDIO. ALL KINDS OF SROREAGE AREAS,

  Dick Weiss RE/MAX Bell Park Realty

  37 van Den Noort St, Putnam, CT 06260
• 

  

  /3

  $6,950,000

  • Land
  • 39 Acres
  • $178,205 per Acre

  67 Holmes Rd, Pomfret, CT 06259

  This 39 Acres of Open Space is being sold as a package, along with 433 Wrights Crossing Rd., Pomfret, MLS #24101484; and 13 Holmes Rd., 25.14 Acres of Open Space, MLS #24174011.

  Lisa Rollins Team Compass Connecticut, LLC

  67 Holmes Rd, Pomfret, CT 06259

Showing Results 41 - 80, Page 2 of 8