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Homes for sale in Windham County Connecticut - Page 1 of 3

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$1,650,000 93 acres 4 Beds | 2 Baths | 1 ½ Bath | 3600 sqft
54 Joy Road, Woodstock, CT 06281 - Windham County

93 acres Woodstock, CT

Location! Location! Location! This property is situated in the heart of the Last Green Valley in one of the premier towns, Woodstock, Connecticut. Just an hours drive from Boston, Hartford and Providence, Woodstock is known for its quiet country living, beautiful winding roads, rolling hills, historical homes, and incredible schools both public and private. This property offers complete privacy with two long, winding driveways. At 93 acres, the land is rich and fertile, with abundant water, excellent well water, a one-acre pond, views of rolling New England hills, beautiful newly constructed barns and spacious a custom-built home that feels like an English cottage with plenty of room for your family. This property and much of the surrou
Erick Taylor
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$474,000 3 acres 4 Beds | 3 Baths | 1 ½ Bath | 3392 sqft
341 River Road, Putnam, CT 06260 - Windham County

Spectacular Historical Home

Spectacular historical home! Set on 3 secluded acres and surrounded by woodland trails this home boasts 7 working fireplaces, wide pine floors throughout, soap stone sinks, Sturbridge Village lighting and impressive forged hardware. Home has been lovingly restored with modern conveniences, central air, high efficiency heating system, gas ranges, all new systems and blown in insulation. This perfect homestead has summer kitchen which is fantastic for the gardener and all their bounty which can also be stored in the large walk in pantry. Mudroom with half bath, laundry and plenty of storage is a great space to come in from a day spent outdoors. Large timber frame barn can house livestock or horses and natural stone boundaries makes this th
Grace Golden Equine Homes Real Estate, LLC
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$450,000 20.7 acres 3 Beds | 2 Baths | 1969 sqft
79 New Sweden, Woodstock, CT 06281 - Windham County

Tranquil horse farm!

Set well off a country road you will find this tranquil and peaceful farmhouse. Sitting atop a small hill the home has views of it's lower pastures, small orchard and large barn. Beautiful restored barn has 7 stalls with room for more, running water, updated electricity, tackroom and feedroom areas. Store enough hay for the season in the large walk up loft. Old riding ring can be brought back with a little work. Your horses will love the hidden, shaded pastures and the abundant trails. Perfect mornings begin on the large screened in porch off your large country kitchen with new appliances and walk in pantry and laundry room. Living room with beamed ceiling and woodstove is a perfect winter retreat. Elegant yet cozy foyer greats guests and l
Grace Golden Equine Homes Real Estate, LLC
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$345,000 4.2 acres
562 Senexet Road No 1, Woodstock, CT 06281 - Windham County

Fairlytale Equestrian Property

Fairytale equestrian property!! Dreamlike covered porch invites you in to this well maintained antique cape. Foyer with widepine boards and original banister welcomes you. Family and living rooms can be separated by large pocket doors. Both rooms have impressive floor to ceiling windows and family room has a gas fireplace. Impressive soapstone counters and deep sink accent the custom wood cabinetry in the kitchen. Stainless steel gas range perfect for the cook! Large bright bonus room has walk in closet, french doors and full bath could easily be converted to a mainfloor master. Morning coffee on the deck will afford you impressive views of the properties gardens and barns. Timberframe barn has walk up loft, attached run in shed and worksho
Grace Golden Equine Homes Real Estate, LLC
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$1,900,000 94 acres 7 Beds | 5 Baths | 1 ½ Bath | 10000 sqft
50 Bull Hill Road, Woodstock, CT 06281 - Windham County

94 Acres Waterfront

Beautiful Arts & Crafts style Bungalow on 94 private acres! Breathtaking views from all the buildings of your very own 10 acre Johnson pond. The main house has 4055 square feet with 11 rooms, 5-6 Bedrooms and 4 baths. It was thoroughly renovated in 1995 by one of the country's leading Stickley / Arts and Crafts dealers. The Guest house has over 1000 square feet, nice size kitchen, large open living / dining area, 1 bedroom & 1 full bath and great deck overlooking the water. The property also has a large 5159 square foot heated commercial building, complete with office area, kitchen area and a bath. This home was featured in American Bungalow magazine for it's incredible Arts & Craftman style design! The property has a small fishing cabin by
Carol Ryniewicz Coldwell Banker
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$799,900 25 acres 5 Beds | 2 Baths | 4 ½ Baths | 5726 sqft
134 Union Rd, Eastford, CT 06242 - Windham County

134 Union Rd

Historic 1733 4 BR Colonial plus in-law apartment annex, 21 acres abutting Yale University Forest, 6 min from I-84, fully equipped 55 seat restaurant (converted post & beam barn) w/commercial kitchen, land all tested w/engineered site plan designs complete for 8 additional two bedroom guest (or year round) dwellings (capacity 32 occupants), no zoning, perfect for hospitality or retreat center, inn, events & functions facility, micro brewery, winery, cidery, private school, training facility, horse property, condo conversion, income rental units, time share, micro farming for specialty foods/herbs/spices, honey bee farm, etc. The Jonathan Hayward house features wideboard floors throughout, 5 fireplaces including beehive oven in the main keep
Dennis Duga Northeast Realty
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$549,900 32.5 acres 4 Beds | 3 Baths | 1 ½ Bath | 2 sqft
1733 Connecticut 169, Woodstock, CT 06281 - Windham County

1733 RT 169

Extraordinary grounds and setting! Gorgeous 32.5 acres with wide expanse of high, open and private acreage, good for horses, no restrictions on animals, organic farming (existing cornfield), or a perfect gentleman's farm, located across the street from 100+ acre sanctuary w/40 acre pond, year round babbling brook (the Little River). This property is 4 tracts of land in 2 states with potential to build multiple homes without subdivision. Zoning allows for agriculture uses, home occupations, accessory buildings, bed and breakfasts, up to 2 additional units used for student housing per dwelling, or, with a permit; equestrian academy, commercial kennels, houses of worship or related private schools, multi family buildings, etc.Tastefully mainta
Dennis Duga Northeast Realty
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$499,900 21 acres 4 Beds | 2 Baths | 1 ½ Bath | 2400 sqft
79 Fitzgerald Road, Brooklyn, CT 06234 - Windham County

79 Fitzgerald Rd

Rare peaceful & bucolic setting; 2 homes on 21 acres, granite 2 car garage, 80 x 24 post & beam barn, owns trout stocked Blackwell's Brook w/land on both east and west sides at the covered bridge! The 1,600 sq ft 3 br 2 bath cape has been completely gutted with all new systems installed, ready to finish. The 800 sq ft 1 bedroom waterfront caretaker's house has additional loft sleeping area, stone fire pit. Many stonewalls, historic sauna, great for animals, horses, gentleman's farm, family compound, etc. Rehab work performed on the main house includes all new plumbing, electric, heating, central air, roof, windows, doors, structural, insulation, well, etc. Location 35 min to Norwich, 43 min to Worcester & 46 min to Providence.
Dennis Duga Northeast Realty
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$349,900 2.84 acres 3 Beds | 3 Baths | 1 ½ Bath | 1896 sqft
21 Ulasik Rd, Canterbury, CT 06331 - Windham County

2.84 acres Canterbury, CT

A peaceful country setting for a classic colonial home in rural Canterbury. Beautiful custom open floor plan Colonial. Large front to back Living room with gas Fireplace. Large custom eat in Kitchen complete with Stainless appliances. Formal Dining Room. Large Master Suite, Walk In Closet and full bath. Hardwood floors in both Dining room and Living room . Mother Nature casts her spell each day on the nearly 3 acres that surround this custom designed and quality built home. Dressed to impress, this pleasing Colonial offers a layout perfect for entertaining and enjoying life. Summer days spent at the pool . The impressive foyer opens to a bright living room with soaring ceilings, fireplace and dining room with a slider to a peaceful and pr
Amy Rio
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$299,900 2.94 acres 4 Beds | 3 Baths | 2072 sqft
47 Sherman Rd, Woodstock Valley, CT 06282 - Windham County

47 Sherman Rd

Country living at it's best with privacy, serenity and room for everyone! 4 bedroom 3 bath home directly on the Still River in beautiful Woodstock; cast for trout and own your own beaver pond in your back yard yet just 10 minutes from I-84 and just 32 minutes from Buckland Hills, the largest Mall/Shopping complex in the state of CT! Quality craftsmanship is everywhere with wood and tile floors, granite counter tops, built in appliances (Jenn-air range top), fireplace, a deck overlooking the protected stream flowage (beaver love this spot) front country sitting porch. Full walk up unfinished 3rd floor is ready to finish for studio or game room. Enjoy all the recreation this area has to offer!
Dennis Duga Northeast Realty
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$299,900 1.4 acres 3756 sqft
817 Providence Pike, Danielson, CT 06239 - Windham County

1.4 acres Danielson, CT

Worthwhile venture at owning a highly visible commercial property set on Rt 6. Building and parking lot are two separate lots-- heightened potential for a variety of uses in future development. Currently being used as a pizza restaurant. Furniture not included. Ask for details regarding kitchen items. Hard to miss the from the 500' of road frontage on a busy route in town. This is an ideal opportunity waiting to be pounced on.
Amy Rio
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$274,900 3.75 acres 3 Beds | 1 Bath | 1 ½ Bath | 1454 sqft
35 Ragged Hill Rd, Pomfret, CT 06259 - Windham County

Pomfret Mini Farm

First time ever on the market! Charming, mini-estate/ horse farm, quality built with so many unique features and upgrades. Open concept living dining area plan, 1950's Ranch w/ 3 bedrooms, fireplaces, new roof, numerous upgrades all on a quiet side Pomfret street. Location, location, location! Gently sloping prime pasture, handsome stone walls galore and numerous outbuildings, (need some TLC), ready for your finishing touches. Dont wait on this one!
Dennis Duga Northeast Realty
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$349,000 4 acres 3 Beds | 3 Baths | 2489 sqft
218 Green Hollow Rd, Danielson, CT 06239 - Windham County

4 acres Danielson, CT

A stunning home you will fall in love with! Very well maintained and lovingly cared for. If you're looking for a comfortable, care free home, look no more! Enjoy a plunge in the heated pool, with privacy for your enjoyment. A wonderful glass enclosed sunroom, just off the back of the home, also heated to enjoy all seasons! The grounds are carefully landscaped with many perennials, birds, and other wild life to watch from any room in the home. The paved driveway is partially shared with the neighbor to the rear of the property. Central air keeps the home cool during those hot summer days. The detached 2 car garage has power and a furnace, to keep you toasty warm while working on your projects or crafts. One car garage under home. Keep out of
Beverly A Peterson AllPoints Realty
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$320,000 4 acres 3 Beds | 2 Baths | 2583 sqft
87 South Brook Rd, Hampton, CT 06247 - Windham County

4 acres Hampton, CT

Lovingly cared for 3 bedroom home with 2 car garage, deck, covered front porch, 30' family room, Huge Country style Kitchen with dine in area, formal dining room, Master suite with full bathroom, 13' walk in closet and a 13x13 private sitting room. A real comfortable home.
Beverly A Peterson AllPoints Realty
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$309,900 9 acres 3 Beds | 2 Baths | 2196 sqft
53 Cheney Rd, Pomfret, CT 06259 - Windham County

9 acres Pomfret, CT

You must see this gorgeous 2,196 square foot ranch style log cabin home situated on 8.7 acres of beautiful fenced pasture in Pomfret, CT. This 3 bedroom, 2 bath home includes an open floor plan consisting of an oversized great room, kitchen, and dining area. You will also enjoy a 3 season sunroom and a 26x12 deck out back for hours of relaxation. This home is absolutely ideal for all horse lover s! The 1,080 square foot barn has 5 stalls, a grain room, and can hold up to 800 bales of hay in the loft. If you are seeking a cozy and private home setting in rural New England, with acres of land for your horses to run free, this place is an absolute must see! This listing consists of two adjoining parcels, #53 on 2.6 acres and #59 on 6.1 acres f
Beverly A Peterson AllPoints Realty
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$305,000 16 acres 4 Beds | 1 Bath | 1580 sqft
65 Miller Rd, Canterbury, CT 06331 - Windham County

16 acres Canterbury, CT

Antique home in need of many repairs. Owners never lived on the premises. There is an amazing barn in the back and the home is located on 16 acres. Also a chicken coop to recreate or use as a artist studio. Buyers must do their due diligence with inspections as the owner has no knowledge. Could be an amazing project to someone who is adventurous. With imagination and willingness to live in an antique home this could be a very fruitful experience. additional acres available in the same neighborhood. Some buildable. Call for information.
Beverly Peterson Century 21 AllPoints Rlty
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$289,900 4 acres 4 Beds | 3 Baths | 1 ½ Bath | 3116 sqft
137 Green Hollow Rd, Danielson, CT 06239 - Windham County

4 acres Danielson, CT

Looking for AMAZING and Unique? Look here! Beautiful Post and Beam home with over 3100 sf of Warmth and Coziness. This home was once a carriage house/ barn and converted into a wonderful place to call home. There are still sliding barn doors separating the dining and great rooms. The great room has soaring 2 story cathedral ceilings with wood beams, raised hearth fireplace with wall barn board accents. Wide board flooring, second story loft/family area overlooks the great room. Large Kitchen with island, open pantry and dining area with window seating and entry to side decking. There are 4 bedrooms including the master suite that offers vaulted ceilings a full bath with shower/tub. First floor laundry room and craft area, 2 decks, garage, f
Beverly A Peterson AllPoints Realty
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$245,000 2 acres 3 Beds | 2 Baths | 2201 sqft
135 Station Rd, Scotland, CT 06280 - Windham County

2 acres Scotland, CT

This beauty sits on 2.5 acres of land lined with pear, apple, and plum trees. Imagine yourself on a porch swing while the wild peacock and the deer stroll by. This home needs a little TLC, however it has great flow, the rooms are a great size, the upstairs bedrooms even bigger and there is SO much closet space you may have to go shopping just to fill them all up, there is a spacious walk out basement and possible bonus room or man/woman cave above the garage, oh yes and did i mention, it is handicap accessible as well. Come by for a showing, and experience the peace and tranquility this home has to offer you
Beverly Peterson Century 21 AllPoints Rlty
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$125,000 1 acres 3 Beds | 1 Bath | 1140 sqft
31 Lovell Ln, Canterbury, CT 06331 - Windham County

1 acres Canterbury, CT

L-Shaped 1140 Square Foot Three Bedroom Ranch Home situated on Acre+ Home site! Property offers Attached Expanded Garage, Workshop, and Storage Areas with additional 1400 Squae Feet of usable space! Main Home Floor Plan Features Applianced Kitchen, Dining Room, Central Living Room, 3 Bedrooms and Full Bath! Attached 21'x36' Garage and Workshop Space previously used in Home Business Operations with adjoining 24'x28' Work/Storage Space. Home needs some updating. 2 Storage Sheds, Paved Drive, Oil Fired Heat, 100 AMP Service, Full Basement! Potential Plus! No Public Records Found for Septic System or Well Information.
Beverly A Peterson AllPoints Realty
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$1,900,000 94.01 acres 6 Beds | 6 Baths | 1 ½ Bath | 4055 sqft
50 Bull Hill Rd, Woodstock, CT 06281 - Windham County

94.01 acres Woodstock, CT

Beautiful Arts and Crafts style Bungalow on 94 private acres! Breathtaking views from all the buildings of your very own 10 acre Johnson pond. The main house has 4055 square feet with 11 rooms, 5-6 Bedrooms and 4 baths. It was thoroughly renovated in 1995 by one of the country's leading Stickley / Arts and Crafts dealers. The Guest house has over 1000 square feet, nice size kitchen, large open living / dining area, 1 bedroom and 1 full bath and great deck overlooking the water. The property also has a large 5159 square foot heated commercial building, complete with office area, kitchen area and a bath. This home was featured in American Bungalow magazine for it's incredible Arts and Craftman style design! The property has a small fishing
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$650,000 12.8 acres 4 Beds | 4 Baths | 1 ½ Bath | 4334 sqft
60 Pomfret Rd, Brooklyn, CT 06234 - Windham County

12.8 acres Brooklyn, CT

An important and impressive piece of CT history, this house displays the plaque of the National Register of Historic Places.In 1825, it was purchased by prominent abolitionist George Benson and is eligible for listing on the Connecticut Freedom trail.The five bay Georgian house is an architectural jewel with the main block and ell. Great care has been taken during an extensive renovation to upgrade the structure while retaining the historic characteristics. This home is immaculate, no details were spared. Updates include a gourmet kitchen, 12 over 12 windows, central air, updated baths, custom made stain glass windows and lamps, beautiful wood and tile floors, updated and immaculate basement including built in drainage and sump, and thre
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$589,900 19.5 acres 5 Beds | 3 Baths | 2987 sqft
27 Hartford Turnpike, Eastford, CT 06242 - Windham County

19.5 acres Eastford, CT

WELCOME TO SCARLET OAK FARM! Former horse boarding farm (easily to go back to) and currently a grass fed beef farm. 40 x 60 barn with 40 x 14 equipment shed. 12 x 12 tack room, grain room, isolation stall and metal grated windows. Capacity of 4-16 stalls. Barn has it's own well, basement shop and 100 amp service. Loft holds 1200 bales of hay. Corbett self waterer. Fenced paddocks and fields. 3 Run ins (10 x 20). 120 x 80 sand riding arena. Miles of trails. Abuts the Natchaug State Forest. Fruit trees- Apple, Cherry and Plum. Vegetable garden area. Chicken Coop. /- 15 acres of cleared land & /- 5 wooded acres. 4 BR, 2 BA Cape with a 1-2 BR, 1 BA Apartment with it's own entry. Heat with the outdoor wood boiler. The main home features a r
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$525,000 3.4 acres 4 Beds | 3 Baths | 1 ½ Bath | 2302 sqft
Lot 21-6-17 Almada Dr, Brooklyn, CT 06234 - Windham County

3.4 acres Brooklyn, CT

Spectacular views from this 3.42 acre lot! Gorgeous custom designed energy efficient home to be built on this exceptional property. The contemporary ranch has over 2300 square feet of living space on the main level and an additional 500 square feet in the finished walkout lower level. Open floor plan features designer kitchen with granite counters and large center island, spacious dining room and living room with 12 foot coffered ceilings, and built in shelving surrounding fireplace. Large master suite, plus three additional bedrooms and first floor laundry. Walkout lower level has huge family room and half bath. Beautiful finish work, large dramatic windows, back deck and porch for enjoying the views. This home is rated Tier 3 Green
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$492,500 3.2 acres 5 Beds | 5 Baths | 1 ½ Bath | 5106 sqft
366 Thompson Rd, Thompson, CT 06277 - Windham County

3.2 acres Thompson, CT

The Horatio Holbrook house, built in 1819, boasts over 5000 square feet of living area. This gracious home features, five bedrooms, and four and and a half baths. The combination of baths and beds lends itself to multiple suites. In 2002, an addition was built which features a large eat in kitchen and butlers pantry on the main floor, and a master bedroom suite above. The gourmet kitchen is bright and airy with expansive views of and access to the patio and private yard. The grounds are lovely, set on over 3 level acres. The barn has three levels with parking for 4 cars on the main level. This property is an architectural jewel, if you love historic homes, don't miss this one.
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$475,000 33.49 acres 3 Beds | 2 Baths | 1690 sqft
22 Palmer Rd, Scotland, CT 06264 - Windham County

33.49 acres Scotland, CT

Hidden Paradise in the Quiet Corner... 33 acre property with many possibilities. Beautiful ranch style home set high on the hill with a 20'x10' porch over looking the valley. This home features a large working kitchen with a center island open to the dining area with large windows to enjoy the sunshine through out the day. For the cool evenings enjoy time in front of the fireplace in the living area. This home also offers a master bedroom suite with a separate shower and full tub with double vanity. This property has 12-15 acres of cleared land for hay or pasture. A 48x24 barn with 2 stalls and room for more and storage for 400 bales of hay. With an attached paddock area. All this and a separate family in-law residence on the property. Bo
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$465,000 99.9 acres 3 Beds | 1 Bath | 1260 sqft
301 North Rd, Ashford, CT 06278 - Windham County

99.9 acres Ashford, CT

Property includes 3 parcels - 301 North Rd which is a lovely cape style home on 25.9 acres, the 59 acre parcel across the street which includes Sabo Pond, and a 15 acre parcel on the corner of North Rd and Summer Lane. An exceptional opportunity to own nearly 100 acres on North Rd.
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$443,000 5.01 acres 4 Beds | 2 Baths | 4010 sqft
41 Newport Rd, Sterling, CT 06377 - Windham County

5.01 acres Sterling, CT

If you are looking for a beautiful home that has been loved and well cared for this is the home for you. Wait till you see all the charm this home offers which includes oak staircase, oak fireplace mantle, pocket doors, 2 staircases, raised panel doors plus so much more. Yes its older but also modern. Three floors of living and then add in the basement area if needed. 5 acres with 9 stall 40x60 post and beam barn with hay loft and heated workshop, fenced pasture, shed, orchard, vegetable garden, and perennial flower beds.
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$425,000 17 acres 8 Beds | 7 Baths | 1 ½ Bath | 6003 sqft
19 Centre Pike, Eastford, CT 06242 - Windham County

17 acres Eastford, CT

INCOME POTENTIAL!!! 3 homes in one on a VERY large, VERY private 17 acre parcel. 8 acres are in the Town of Eastford with the Main House and 9 acres are in the Town of Woodstock. Live in one and rent the others!!! Perfect for a large family, Elder Care, Handicap housing, Boarding House, Church, or any combination. Main house was built in 1992 but 2 huge additions were added in late 2010. Six decks both covered and open. 200 amp separate service for all 3 units w/Extra Meter for new structures. Separate utilities. New Roof, New Vinyl Siding, 8x12 Shed with power,(3) 275 Oil Tanks, Spiral and Real Wood oversized Stairs ,Heated Garage, Welding plug & 20 FT Workbench W/Cabinets in Garage, Utility Sink, Jet Tub, Dry Basement, 2 New oil burner
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$400,000 30.64 acres 5 Beds | 4 Baths | 3176 sqft
380 N Society Rd, Canterbury, CT 06331 - Windham County

30.64 acres Canterbury, CT

Beautiful Colonial boasting over 3,100 square feet with 5 bedrooms and 4 full baths. Enjoy broad sweeping views of a magnificent 30 acre estate. The 2 story foyer with architectural columns lead to the dining and living rooms. Nicely appointed center island kitchen and open floor plan make the ideal setting for entertaining. First floor master bedroom suite with whirlpool bath. Another 1st floor bedroom is ideally suited as an office. 3 more generously sized bedrooms and a full bath are located on the 2nd floor. Features include: 9 foot tray ceiling, central air, fireplace, 2 car garage, huge walk out basement & energy efficient multi-zone heat. There is even a 24KVA diesel powered emergency whole house generator! The 16x18 deck is the perf
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$395,000 6.89 acres 4 Beds | 4 Baths | 1 ½ Bath | 4476 sqft
104 Windham Center Rd, Windham, CT 06280 - Windham County

6.89 acres Windham, CT

Wonderful Greek Revival home built in 1780/1835. Completely redone by New England Design in 2005-2006. A grand home Featuring hardwood flooring, 3 fireplaces, formal dining room, huge 35x17 family room and a formal office with built ins. Beautiful manicured gardens and walkways. Stamped concrete patio and sitting area. Huge two story barn for storage and 3 car parking area.