Windham County CT Homes for Sale

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  /11

  $550,000

  • Land
  • 43.3 Acres
  • $12,702 per Acre

  0 N Canterbury Rd, Canterbury, CT 06331

  Discover the beauty and character of this stunning 43.3-acre parcel featuring a perfect blend of wooded areas and open fields, offering endless possibilities for your dream home, private retreat, recreational getaway, or future investment. A shared drive provides access beginning at a truly unique feature - an old covered bridge located on the property that is proudly listed on the National

  Danielle Bakanowsky Kazantzis Real Estate, LLC

  0 N Canterbury Rd, Canterbury, CT 06331
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  /7

  $39,900

  • Land
  • 4.2 Acres
  • $9,500 per Acre

  46 North Rd, Windham, CT 06280

  Great opportunity to own a lot of record at a great price, approx. 3.9-4.2 acres. Offered as raw land. No formal survey available, all soil testing and surveying to be done by the potential owner. Great location, North Rd. is Route 14, across from the Windham Center School.

  

  Rick Nassiff

  KW Legacy Partners

  46 North Rd, Windham, CT 06280
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  /7

  $594,900

  New Construction

  • 4 Beds
  • 2 Baths
  • 2,000 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
• 

  

  

  /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
• 

  

  

  /40

  $1,995,000

  $855K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,723 Sq Ft

  158 W Quasset Rd, Woodstock, CT 06281

  Extraordinary Waterfront Estate. Set on an exceptional 5.5-acre private lot with 265 feet of shoreline frontage, this completely rebuilt luxury residence offers a rare opportunity to own one of Woodstock's premier lakefront properties. Arrive via a long, newly paved private driveway that winds through a tranquil setting before revealing this stunning waterfront retreat. Offering 3,971 square

  Skyla Gagnon RE/MAX Bell Park Realty

  158 W Quasset Rd, Woodstock, CT 06281
• 

  

  /39

  $880,000

  • 4 Beds
  • 5 Baths
  • 5,087 Sq Ft

  48 Grey Fox Landing, Woodstock, CT 06281

  Welcome to this exceptional custom-built ranch, perfectly situated at the end of a peaceful cul-de-sac in South Woodstock. Offering a great blend of luxury, comfort, and versatility, this impressive home boasts 2,822 square feet of beautifully designed main-level living space, with over 5000 square feet of total finished living area including the private in-law apartment above the garage and the

  Lynn Converse RE/MAX Bell Park Realty

  48 Grey Fox Landing, Woodstock, CT 06281
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  /4

  $89,900

  • Land
  • 6.27 Acres
  • $14,338 per Acre

  0 Drain St, Hampton, CT 06247

  This lot was created in 2005. Perc tests are 20 years old and might change based on where the home is desired to be located on the property.

  Mae Lyons Stonehouse Real Estate Co., LLC

  0 Drain St, Hampton, CT 06247
• 

  

  /4

  $499,900

  • Land
  • 11.15 Acres
  • $44,834 per Acre

  117 Riverside Dr, North Grosvenordl, CT 06255

  Great opportunity awaits on this 11 acre multi use property that runs along the airline trail. Some of the many potential uses would be townhouses, duplex's, multi families and single family homes. Gravel is on site. City sewer and 3 phase power. This property is located near 395 which is great for easy commuting into Massachusetts. .

  Cary Marcoux RE/MAX Bell Park Realty

  117 Riverside Dr, North Grosvenordl, CT 06255
• 

  /2

  $1,295,000

  • Land
  • 12.8 Acres
  • $101,172 per Acre

  99 Azud Rd, Thompson, CT 06277

  Fully approved and shovel ready for 60 Multi Family Units! Affordable project can be developed in phases. Public sewer available, private well and 3 Phase Power. Close to the airline trail for hiking and cycling. Conveniently located restaurants and shopping. Close proximity to the casinos, Worcester, Providence, Boston and the Rhode Island and Ct Shoreline.

  Cary Marcoux RE/MAX Bell Park Realty

  99 Azud Rd, Thompson, CT 06277
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  /36

  $419,900

  $30K 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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  /24

  $595,000

  • Land
  • 100 Acres
  • $5,950 per Acre

  259 Quarry Rd, Woodstock, CT 06281

  Discover the possibilities on this exceptional 100-acre parcel on Quarry Road in scenic Woodstock, Connecticut. Boasting approximately 1,900 feet of road frontage, this expansive property offers a rare combination of privacy, natural beauty, and development potential. The current owner has already cleared three beautiful potential building sites, each positioned to take advantage of the

  

  Carol Ryniewicz

  CR Premier Properties

  259 Quarry Rd, Woodstock, CT 06281
• 

  

  /40

  $999,900

  $200K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,393 Sq Ft

  46 Cemetery Rd, Canterbury, CT 06331

  Exceptional opportunity to own a private country estate featuring a well-maintained Cape-style log home set on 41.83 acres of beautiful land. This charming residence offers 3 bedrooms and 2 full bathrooms, with a comfortable floor plan that includes a spacious family room and a recreation room in the lower level, providing plenty of space for relaxation, entertainment, and hobbies. Enjoy your

  Kevin Brignole Spaulding Realty Group, LLC

  46 Cemetery Rd, Canterbury, CT 06331
• 

  

  /40

  $500,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,284 Sq Ft

  30 Grant Hill Rd, Brooklyn, CT 06234

  Custom passive solar Contemporary set on 5+ private acres surrounded by natural beauty and peaceful scenery. A 5-year-young sunroom with tile flooring offers flexible space for relaxing, gardening, or enjoying year-round views of the landscape. Step outside to the spacious deck, ideal for outdoor dining or quiet mornings overlooking the tranquil setting. The inviting living room features a newer

  

  Mary Collins

  Berkshire Hathaway NE Prop.

  30 Grant Hill Rd, Brooklyn, CT 06234
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  /10

  $249,900

  • Land
  • 25.7 Acres
  • $9,724 per Acre

  220 Plains Rd, Windham, CT 06280

  Wonderful potential development opportunity. Road frontage on 2 roads, approximately 1350' of frontage on Plains Rd., and approximately 450' of frontage on Anna Maria Ln., and existing cul-du-sac subdivision. Possible 7-8 lots subdivision to be created.

  

  Rick Nassiff

  KW Legacy Partners

  220 Plains Rd, Windham, CT 06280
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  /6

  $150,000

  • Land
  • 4.25 Acres
  • $35,294 per Acre

  406 Sabin St, Putnam, CT 06260

  Rare opportunity to acquire a potential residential development site located within a Qualified Opportunity Zone in Putnam. Previously approved subdivision plans in 2008 along with updated conceptual plans completed in 2022 provide valuable groundwork for future development. The property was designed for a proposed 12-unit subdivision with city water and sewer available, offering excellent future

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  406 Sabin St, Putnam, CT 06260
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  /40

  $2,950,000

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

  282 & 260 Searles Rd, Pomfret, CT 06259

  A rare and refined country estate offering privacy, luxury, and elegance on over 53 acres in scenic Pomfret. This extraordinary 4,442 sq ft custom, Tennessee fieldstone home includes 4 bedrooms and 5 baths-including a private in-law apartment/second primary suite with its own entrance. An additional 16+ acre building lot provides development potential. Surrounded by forest and adjacent to 175

  John Downs Berkshire Hathaway NE Prop.

  282 & 260 Searles Rd, Pomfret, CT 06259
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  /5

  $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
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  /40

  $1,395,000

  $55K PRICE DROP

  • 4 Beds
  • 5.5 Baths
  • 6,394 Sq Ft

  1374 Route 171, Woodstock Valley, CT 06282

  Set on 10.3 private acres in desirable Woodstock Valley, "Blue Heron Glade" offers a rare blend of privacy, natural beauty, and thoughtfully designed living spaces in Connecticut's Quiet Corner. A long private driveway with a charming cobblestone bridge leads to this exceptional property surrounded by stone walls, abundant wildlife, and a large pond frequented by blue herons. The main residence

  Kristen Kaskela Berkshire Hathaway NE Prop.

  1374 Route 171, Woodstock Valley, CT 06282
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  /34

  $239,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 3,243 Sq Ft

  259 Ference Rd, Ashford, CT 06278

  Rare value-add and redevelopment opportunity situated on 3.5 acres with over 3,200 square feet of existing space. Currently configured as a mixed-use commercial property, this expansive parcel offers strong potential for multifamily conversion, redevelopment, expansion, mixed-use investment, income-producing use, or possible additional building opportunities, subject to buyer due diligence and

  Michelle Gutierrez Social & Co Realty

  259 Ference Rd, Ashford, CT 06278
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  /23

  $379,000

  $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft

  222 Tower Hill Rd, Chaplin, CT 06235

  Beautifully set on 4.02 scenic acres in Chaplin, Connecticut, this charming 3-bedroom, 2-bath home offers the perfect blend of character, privacy, and versatility. Featuring approximately 1,600 square feet, the home showcases soaring vaulted ceilings, stunning exposed beams, and an inviting open-concept kitchen, dining, and living area filled with natural light. The finished lower level offers a

  Lisa Therecka Therecka & Associates LLC

  222 Tower Hill Rd, Chaplin, CT 06235
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  /34

  $638,777

  $11K PRICE DROP

  • 10 Beds
  • 5 Baths
  • 3,389 Sq Ft

  120 North St, Willimantic, CT 06226

  Income producing multi family property offering a strong opportunity for investors or owner occupants alike. One unit is currently not leased, providing immediate leasing potential or flexibility for owner occupancy. Property presents the opportunity to generate rental income with additional upside potential over time. Detached garage offers added utility with potential for storage, workshop

  Michelle Mandel Carl Guild & Associates

  120 North St, Willimantic, CT 06226
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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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  /2

  $100,000

  • Land
  • 3.85 Acres
  • $25,974 per Acre

  70 Cutler Rd, Dayville, CT 06241

  lovely lot 3.5 acres lot great location builders opportunity

  Ned Murtha Coastal Properties Group

  70 Cutler Rd, Dayville, CT 06241
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  /2

  $100,000

  • Land
  • 8.5 Acres
  • $11,765 per Acre

  43 Fall Brook Rd, Danielson, CT 06239

  lovely 8.5 acre lot , raw land

  Ned Murtha Coastal Properties Group

  43 Fall Brook Rd, Danielson, CT 06239
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  /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
• 

  

  /3

  $6,950,000

  • Land
  • 25.16 Acres
  • $276,232 per Acre

  13 Holmes Rd, Pomfret, CT 06259

  This 25.16 Acres of Open Space is being sold as a package along with 433 Wrights Crossing Rd., Pomfret, MLS #24101484, and 67 Holmes Rd. 39 Acres of Open Space, MLS #24174026.

  Lisa Rollins Team Compass Connecticut, LLC

  13 Holmes Rd, Pomfret, CT 06259
• 

  

  /40

  $6,950,000

  • 12 Beds
  • 9 Baths
  • 10,517 Sq Ft

  433 Wrights Crossing Rd, Pomfret Center, CT 06259

  Welcome to Bark Meadow Farm, a 127-acre legacy estate once cherished by the Gulden mustard family in CT's "Quiet Corner." The journey begins at a majestic entrance, where a striking allee of century-old maples stands alongside magnificent oaks nearing 200 years of age. This multi-generational compound offers 12 bedrooms & 7.2 bathrooms across three year-round residences. At the heart is the 1799

  Lisa Rollins Team Compass Connecticut, LLC

  433 Wrights Crossing Rd, Pomfret Center, CT 06259
• 

  

  /22

  $299,900

  • Land
  • 79 Acres
  • $3,796 per Acre

  00 Ide Perrin Rd, Woodstock, CT 06281

  On a private road surrounded by unspoiled natural beauty, this remarkable 79-acre property offers exceptional privacy and endless potential. Two brooks enhance the landscape - Lebanon Brook along the western boundary and Porter Pond Brook to the east. The land features a mix of wetlands and highlands, heavily wooded with abundant timber resources. Create your secluded homestead in the wilderness

  

  Catherine Howard

  Berkshire Hathaway NE Prop.

  00 Ide Perrin Rd, Woodstock, CT 06281
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  /9

  $285,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  37 Ruth St, Danielson, CT 06239

  Discover the potential in this fixer-upper featuring an ideal floor plan with spacious, flowing living areas and endless possibilities to make it your own. The open and functional layout offers great bones for a renovation project, with generously sized rooms, abundant natural light, and a seamless flow perfect for modern living and entertaining. Whether you're an investor, flipper, or buyer

  

  Elizabeth Scranton

  Kazantzis Real Estate, LLC

  37 Ruth St, Danielson, CT 06239
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  /31

  $699,000

  Open Sat 10AM - 12PM $121K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,344 Sq Ft

  81 Anderson Rd, Pomfret Center, CT 06259

  Welcome to this timeless 4 bedroom Contemporary Colonial estate offering over 3000 square feet of refined living space, nestled in the heart of scenic Pomfret. This stately home blends classic New England charm and privacy in the cul-de-sac neighborhood.Step inside this grand entryway to find rich wood flooring throughout lending warmth and sophistication to every room. The main level boasts a

  Kathy Rickey Signature Properties of N.E.

  81 Anderson Rd, Pomfret Center, CT 06259
• 

  /2

  $90,000

  • Land
  • 5.09 Acres
  • $17,682 per Acre

  35 Brooklyn Rd, Canterbury, CT 06331

  Located in area of new homes. Slightly wooded. Great location to build your new home.

  Maura Von Deck Von Deck Realty, LLC

  35 Brooklyn Rd, Canterbury, CT 06331
• 

  

  /39

  $874,000

  $125K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,808 Sq Ft

  254 Beaver Hill Rd, North Windham, CT 06256

  Hidden Acres is a rare opportunity to own 70+ secluded acres where rustic charm, craftsmanship, and modern functionality come together. Tucked away in a private setting, this extraordinary farm features a 14,400-square-foot equestrian facility with a 12-stall barn and indoor riding arena, ideal for horse enthusiasts, trainers, or those seeking a premier recreational property. A heated

  Lori Vogel William Raveis Real Estate

  254 Beaver Hill Rd, North Windham, CT 06256
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  /13

  $170,000

  • Land
  • 3.4 Acres
  • $50,000 per Acre

  6 Broad St, Killingly, CT 06239

  This UNIQUE BEAUTIFUL 3.4-acre lot is truly a must see. Walk past the existing old barn, look to the right and then walk all the way down on the left, it is simply beautiful! Zoned - RESIDENTIAL HIGH DENSIITY there are so many possibilities for use. Single-family, two-family, and multi-family dwellings, Professional office or customary home occupation, uses allowed with special permit

  Belinda Culp Berkshire Hathaway NE Prop.

  6 Broad St, Killingly, CT 06239
• 

  

  /39

  $454,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,710 Sq Ft

  37 Valley View Dr Unit 14A, Killingly, CT 06241

  Upscale new-construction end-unit condo featuring 3 bedrooms, 2.5 baths, and a 1-car garage. This beautifully designed home offers an open-concept layout, modern finishes, and abundant natural light throughout. The spacious walk-out basement provides additional living or storage potential. Located on a quiet cul-de-sac, this desirable end unit combines privacy, comfort, and convenience in a

  Colleen Rybacki Brunet and Company Real Estate

  37 Valley View Dr Unit 14A, Killingly, CT 06241
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  /38

  $454,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,710 Sq Ft

  39 Valley View Dr Unit 14B, Killingly, CT 06241

  To Be Built!! Still time to customize your new home with the builder! Upscale condo's with all End Units. Stainless Steel Appliances included, Granite Counter Tops (upgrades available). Work closely with builder to make this house your new custom home in a beautiful community setting with walking trails around the Preserve. Fully furnished model unit on site to show. Leave the lawn care and

  Colleen Rybacki Brunet and Company Real Estate

  39 Valley View Dr Unit 14B, Killingly, CT 06241
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  /25

  $355,000

  $24K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  57 Beaver Dam Rd, Woodstock Valley, CT 06282

  Adorable year-round home on Lake Bunggee, ideally located across from a private beach with stunning lake views. The main level features vaulted ceilings and an open-concept layout connecting the living room, dining area, and kitchen. There are two bedrooms on the main floor, along with a finished room on the lower level for added space. Enjoy not only the beautiful lake views but also a private

  

  Carol Ryniewicz

  CR Premier Properties

  57 Beaver Dam Rd, Woodstock Valley, CT 06282
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  /35

  $749,900

  $200K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 3,004 Sq Ft

  524 Wauregan Rd, Brooklyn, CT 06234

  Welcome to this exceptional, custom built brick home, set on a stunning piece of property where quality, craftsmanship, and timeless design come together beautifully. From the moment you step inside, you will appreciate the vaulted ceilings, open layout, and impressive mix of hardwood, marble and tile flooring. The heart of the home features a beautifully designed kitchen with quartz countertops,

  

  Mandy Gruslin

  Kazantzis Real Estate, LLC

  524 Wauregan Rd, Brooklyn, CT 06234
• 

  

  /12

  $204,500

  $11K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,446 Sq Ft

  85 Wauregan Rd, Danielson, CT 06239

  Check out this antique Cape just minutes from downtown Danielson! This home has 3 bedrooms located on the upper floor, with plenty of flexible space. The primary floor has many wonderful features including a large kitchen that opens up to the back deck, a full bath, and a dining space. Enjoy overlooking the yard from the enclosed deck! Plumbing did not hold positive air pressure at the time of

  Ryan King Aspen Realty Group

  85 Wauregan Rd, Danielson, CT 06239
• 

  

  /40

  $1,025,000

  $325K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 5,459 Sq Ft

  354 Pomfret St, Pomfret Center, CT 06259

  At the end of a long private drive on six rolling acres sits the 1880 Clark Cottage at Wintergreen, a Pomfret estate on the National Register of Historic Places. It's a rare antique that asks nothing of you: 19th-century craftsmanship paired with a fully renovated chef's kitchen and a spa-inspired primary bath, impeccably maintained throughout. Approximately 5,000 square feet span three finished

  Ranee Bibisi LAER Realty Partners

  354 Pomfret St, Pomfret Center, CT 06259
• 

  /2

  $90,000

  • Land
  • 4.25 Acres
  • $21,176 per Acre

  45 Brooklyn Rd, Canterbury, CT 06331

  Located on country Rd. Lightly treed lot. Perc tested and septic plans available.

  Maura Von Deck Von Deck Realty, LLC

  45 Brooklyn Rd, Canterbury, CT 06331

Showing Results 201 - 240, Page 6 of 8