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Homes for sale in Windham County Connecticut - Page 1 of 2

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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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$469,000 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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$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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$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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$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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$589,900 19.5 acres 5 Beds | 3 Baths | 2987 sqft
27 Hartford Tpke (Farm), 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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$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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$449,000 23.13 acres 3 Beds | 2 Baths | 1 ½ Bath | 1672 sqft
146 Estabrooks Rd, Hampton, CT 06247 - Windham County

23.13 acres Hampton, CT

Outstanding Business Opportunity - This 23 acre horse farm property boarders the State Forest. Ride right out from the property onto the airline trail. This property features a 150X80 indoor riding arena with heated and a/c viewing room and attached barn with 14 stalls including a wash stall. Barn features a bathroom w/laundry. Turnouts and plenty of parking. Generator (negotiable) runs the house and smaller barn. 200X300 sand rink. Lighting down the driveway to the large barn. Six (6) fenced pastures. Business opportunity for boarding horses. The house is a raised ranch with 3 bedrooms 1.1 baths, large covered deck off the dining room. Extra storage under the deck. Come make this your new home.
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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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$364,900 2.84 acres 4 Beds | 3 Baths | 1 ½ Bath | 2500 sqft
10 Brookside Lndg, Putnam, CT 06260 - Windham County

2.84 acres Putnam, CT

This gorgeous ~2500 SF colonial with farmers porch is in an incredible subdivision close to the RI line! Construction has begun, and there is time to pick your finishes, colors, and more! The oversized entry way greets you with a half bath, formal dining room through to an oversized kitchen with island. Granite counters, hardwood floors, and stunning cabinets. Generous sized living room with propane fireplace and access to your oversized 20x12 deck!! If thats not enough there an office on the first floor, or could be a playroom! The second floor boasts a master suite that has his and hers walk in closets! 2 nicely sized bedrooms connected by a full bath, and a bonus/4th bedroom over the garage with plenty of storage space! Second floor laun
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$350,000 40 acres 3 Beds | 2 Baths | 2186 sqft
689 Pudding Hill Rd, Hampton, CT 06247 - Windham County

40 acres Hampton, CT

On the market for the first time in 50 years. A warm and inviting home on 40 acres is just waiting to become someone's cherished homestead. Recently painted and renovated, it offers generous sized, light filled rooms in over 2000 sq. ft of living space. Country Kitchen and Breakfast Room with decorative wainscoting, formal Dining and Living room w. fireplace and built-ins, Study/Office plus a Sunroom. A new full bathroom, laundry and mud room complete the first floor. The second floor has three sunny Bedrooms and one full bath. Plenty of storage in the attic. Two car garage. Two large barns and several sheds offer many possible uses. All on 40 open and lightly wooded acres.
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$350,000 3.38 acres 4 Beds | 3 Baths | 1 ½ Bath | 2500 sqft
14 St. James Place, Putnam, CT 06260 - Windham County

3.38 acres Putnam, CT

Custom built 4 bedroom, 2500 square foot colonial. Gas heat, central air, spacious and open floor plan. Second floor laundry, large master suite with full bath and walkin closet. Walkout basement, back deck, paved driveway. Lovely private lot at the end of the cul-de-sac.
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$349,900 2 acres 4 Beds | 3 Baths | 1 ½ Bath | 2400 sqft
125 Kapitulik, Thompson, CT 06255 - Windham County

2 acres Thompson, CT

Under deposit but more available nearby!! This gorgeous 2400 SF colonial with farmers porch is just minute from the highway on a non thru road! Completion will be early summer!! The warm colors and oversized entry way greet you with a half bath, formal dining room through to an oversized kitchen with island. Granite counters, hardwood floors, and stunning cabinets. Generous sized living room with propane fireplace and access to your oversized 20x12 deck!! If thats not enough there an office on the first floor, or playroom! The second floor boasts a master suite that has his and hers walk in closets! 2 nicely sized bedrooms connected by a full bath, and a bonus/4th bedroom over the garage with plenty of storage space! Second floor laundry,
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$349,900 12.4 acres 2 Beds | 2 Baths | 2896 sqft
564 Hubbard Rd, Danielson, CT 06239 - Windham County

12.4 acres Danielson, CT

Enjoy nature's spectacular changing seasons from every room in this fabulous architect designed contemporary home situated on over 12 acres. Windows throughout add natural light and the interesting floor plan with vaulted ceilings create a wonderful sense of space! A dramatic great room with fireplace, cathedral ceilings, exposed wood beams, stained glass window, and sliders to a deck spanning the length of the room is the centerpiece of this home. First floor master suite opens up via slider to a bluestone patio which overlooks a spacious yard, mature plantings, and a fire pit. Upstairs you will find the second bedroom with built in loft, bathroom, and two extra rooms as well as access to two additional decks to enjoy all nature has to off
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$345,000 2.08 acres 3 Beds | 2 Baths | 2354 sqft
43 Brookstone Dr, Sterling, CT 06377 - Windham County

2.08 acres Sterling, CT

Lovely custom ranch with exceptional attention to detail, inside and out. Bright open floor plan features spacious kitchen with stainless appliances, large dining area, living room with fireplace. First floor master bedroom suite plus two additional bedrooms, full bath and first floor laundry. Second floor has additional living area with an office/sitting room and large family room with heat and air conditioning. Beautiful, private back yard features patio with fire pit, pool with deck, and a volleyball court. Additional features include 300 ft paved driveway, shed, oversized two car garage, pretty front porch and landscaping. This one owner home has been beautifully maintained and is in immaculate, move-in condition.
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$339,000 1.7 acres 1659 sqft
792 Hartford Pike, Dayville, CT 06241 - Windham County

1.7 acres Dayville, CT

Killingly-Commercial Property with significant road frontage. Property has home and garage on site with 2 other larger commercial land parcels abutting. Located just east of Zips Diner and Killingly Commons.
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$328,000 2.35 acres 5 Beds | 3 Baths | 1 ½ Bath | 2878 sqft
162 James Rd, Ashford, CT 06278 - Windham County

2.35 acres Ashford, CT

Unique Stunning Contemporary Cape with an Open Sunny Floor Plan! Beautiful Wood Floors, Many Built Ins and Special Features, 3 Fireplaces and 3 Wood Stoves! This Very Spacious Home is Quietly Set Back in a Wooded Country Setting with 5 Bedrooms! Spacious Rooms, Master Bedroom Suite with a Fireplace and Full Bath, a Soaking Tub and Stall Shower. Lots of Closets, Storage and Oak Floors. Huge Great Room/Living Room with a Fireplace,Wood Stove and Plenty of Room for a Pool Table! Eat in Kitchen, Formal Dining Room with a Beautiful Stone Fireplace and another Separate Wood Stove. New Furnace, Many Updates with Beautiful Woodwork and Doors! Lovingly Maintained with a Huge Wrap Around Deck. Move Right In.
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$325,000 11.04 acres 4 Beds | 5 Baths | 1 ½ Bath | 4560 sqft
460 Brayman Hollow Rd, Pomfret, CT 06259 - Windham County

11.04 acres Pomfret, CT

Antique colonial with hardwood floors and the charm of yesteryear. Built in 1740, this house has over 4,000 sq ft of living space. 4 large bedrooms, 4 full baths and 1 half bath. It has an enclosed porch, inground pool, patio and wonderful grounds. This property is being sold with 3 other parcels for a total of 11.04 acres. One of the other parcels has a 3 room bungalow on it. Realtor related. Subject to third party approval
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$284,900 2.26 acres 4 Beds | 2 Baths | 1763 sqft
589 Brayman Hollow Rd, Pomfret, CT 06259 - Windham County

2.26 acres Pomfret, CT

This is your chance to own an incredible piece of history that has been completely renovated with modern amenities, layout and comforts yet has the charm of an antique! The home was completely renovated throughout ~2014 starting from the outside, roof, windows, paint, siding is in great condition! The interior was taken down to the studs and meticulously rebuilt to modern standards, yet kept the character and coziness of the original structure! Four generous sized bedrooms including one on the first floor with stenciled wood floors. Featuring 2 full bathrooms, 1 on the first floor, this lends itself to great living versatility. The completely renovated eat in kitchen with granite/butcher block counters is open to the living room. Living ro
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$249,900 2.3 acres 3 Beds | 3 Baths | 2337 sqft
35 Shuba Lane, Chaplin, CT 06235 - Windham County

2.3 acres Chaplin, CT

Very appealing Classic Cape on professionally designed acres on non-through street. Handsome fencing encloses the side and back areas, the large stone patio and covered porch as well as the cutest little barn anywhere. This spacious house has 3 4 Bedrooms, large Living room w. stone fireplace, formal Dining room, Kitchen w. Breakfast Bar plus a room perfect as office or exercise room. Rooms have oak, bamboo or tile flooring.The former garage was expertly transformed into what could be perfect in-law and guest quarters or even studio space. There are plenty of cabinets, appliances, a full bath and separate entrance. The mechanicals inc. Buderus furnace, generator, solar panels.
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$219,900 3.48 acres 4 Beds | 2 Baths | 1856 sqft
120 Littlefield Rd, Scotland, CT 06264 - Windham County

3.48 acres Scotland, CT

Beautiful well maintained country home in quiet friendly neighborhood. Close to UCONN and ECSU. exceptional elementary school with small classes fresh paint throughout oak hardwood flooring newer stainless steel apliances walkout basement with woodstove and halfwall large deck overlooking property level lot close to shopping and casinos Please click on the Virtual Tour for more photos and an important message.
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$219,900 3.48 acres 4 Beds | 2 Baths | 1862 sqft
120 Littlefield Rd, Scotland, CT 06247 - Windham County

3.48 acres Scotland, CT

Country home set on a quiet road. Large bedrooms with tons of space!! First floor bedroom could be the master bedroom. Wood floors, Large deck over looking private back yard. Plenty of room to add a garage if you desire. Walkout basement could be finished for additional living space or a great workshop.
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$219,000 2.9 acres 4 Beds | 2 Baths | 3020 sqft
172 Halls Hill Rd, Danielson, CT 06239 - Windham County

2.9 acres Danielson, CT

Own a piece of history! This beautiful antique colonial was once home to Captain Alex Gaston, whose son William Gaston became mayor of Boston and Governor of Massachusetts in 1875. The "Gaston Manse" has all of the rambling space and charm of a vintage home, and the caring updates from those who have lived in and loved this property. The current owners have painstakingly renovated the entire first floor, with a completely remodeled kitchen,full bath,dining room,and living room with an attached den (both with fireplaces). The kitchen includes brand new stainless steel appliances, custom wood counters, an antique island, and a built-in pantry. The large beehive fireplace serves as the centerpiece of the formal dining area, with plenty of sunl
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$204,900 0.69 acres 3684 sqft
15 Providence Rd, Brooklyn, CT 06234 - Windham County

0.69 acres Brooklyn, CT

Brooklyn-Village Commercial District Property with tremendous charm. This jewel sits on Route 6 at the intersection of Rt 169. Located between two churches this home/business offers over 3500 sq ft of space with some antique charm.
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$191,000 3.6 acres 4 Beds | 1 Bath | 1954 sqft
80 Doring Dr, Danielson, CT 06239 - Windham County

3.6 acres Danielson, CT

Killingly: Cape with 3 possibly 4 bedrooms situated on 3.6 acres on a secluded rear lot approximately 600 ft off North St. Home has 1 bath and 2 car detached garage. Newer windows, Well and Septic. Home also has handicap ramp and one first floor bedroom. Nicely maintained home which is close to town.
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$165,000 2 acres 5 Beds | 2 Baths | 1 ½ Bath | 3199 sqft
252 Main Street, Hampton, CT 06247 - Windham County

2 acres Hampton, CT

Stately home in Historic District on Hampton Hill. Known as "Maplehurst" this home's setting offers lovely views from its many windows. Light filled, generous sized rooms feature fireplaces, built-ins and hardwood floors throughout. Formal Living and Dining rooms, Library and Parlor plus 5 Bedrooms make it a very comfortable home with many nooks and crannies to explore. Beautiful moldings around doorways and windows hark back to a gracious lifestyle. With some tlc and appropriate upgrades, this grand dame will shine again. There's also a nice old barn and an apple orchard, all on 2 acres. Conveniently located - walk to Library, Post Office and Churches. Easy drive to EasternCt Univ, UCONN and major highways.
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$159,900 0.57 acres 6632 sqft
245 School St, Putnam, CT 06260 - Windham County

0.57 acres Putnam, CT

Great space with unlimited possibilities. Past use was a chiropratric office for many years. Plenty of off street parking and great visibility from route 44 across the street from the ball field. Would make a great office space or sandwich facility with town approvals a must. Has a two story barn attached that would make a great studio or other commercial use or could be a grand home with lots of storage. Many possibilities!
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$125,000 4.92 acres 3 Beds | 2 Baths | 1 ½ Bath | 1398 sqft
505 Porter Pond Rd, Sterling, CT 06377 - Windham County

4.92 acres Sterling, CT

Antique home dating back to 1740,still has many years left with some vision and work. Beautiful lot with mature trees and privacy. Original charm present with 3 stone fireplaces and woodwork. 3 bay garage has full walk up loft featuring office space and workshop. Will not go most financing. Peeling paint and major cosmetics needed.
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$105,000 3.3 acres 3 Beds | 2 Baths | 1 ½ Bath | 2536 sqft
85 Green Hollow Rd, Plainfield, CT 06354 - Windham County

3.3 acres Plainfield, CT

Colonial home with in law apartment. Needs extensive work, Cash or 203k only. Short sale. No disclosures due to this being an estate.