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Windham County CT Homes for Sale with Pool

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  • /40

    $649,900

    • 4 Beds
    • 2.5 Baths
    • 2,682 Sq Ft

    37 Pulpit Rock Rd, Woodstock, CT 06281

    Location, location, location! Tucked away on a quiet scenic road just steps from historic Woodstock Hill and Woodstock Academy, this classic Colonial offers 2,682 sq. ft. of timeless charm on 1.6 acres-one of the most desirable and private settings in Woodstock. Inside, wide-plank oak floors, exposed beams, and two fireplaces create a warm and inviting atmosphere. The open kitchen and dining

    Agent Photo

    Carol Ryniewicz

    CR Premier Properties

    (860) 854-3110

    37 Pulpit Rock Rd, Woodstock, CT 06281
  • /40

    $845,000

    • 3 Beds
    • 3.5 Baths
    • 2,209 Sq Ft

    5 Kies Rd, Killingly, CT 06239

    **Welcome to Your Dream Home!** Nestled on over 5 picturesque acres, this stunning 3+ bedroom, 3.5 bathroom residence is a sanctuary of comfort and style, surrounded by state forest and adjacent to an expansive 20+ acres of untouched land. Experience the perfect blend of nature and luxury in this meticulously maintained property. **Key Features:** - **Comfort Year-Round:** Enjoy year-round

    Rene Barbeau RE/MAX Bell Park Realty

    5 Kies Rd, Killingly, CT 06239
  • /40

    $799,000

    • 3 Beds
    • 4 Baths
    • 2,323 Sq Ft

    223 Barlow Cemetery Rd, Woodstock, CT 06281

    Discover modern luxury living in this stunning 2011-built Colonial. Perfectly situated on a picturesque waterfront lot with privately owned pond frontage, this thoughtfully designed home offers a lifestyle of elegance and comfort. The home offers 3 bedrooms, two full baths, and two half baths. You will love the classic oak flooring, crown molding, and light-filled living spaces. The finished

    John Downs Berkshire Hathaway NE Prop.

    223 Barlow Cemetery Rd, Woodstock, CT 06281
  • /40

    $772,500

    • 3 Beds
    • 4 Baths
    • 3,610 Sq Ft

    310 S Bigelow Rd, Hampton, CT 06247

    The William Bennett home built in 1738. This home stayed in the same family until the 1940's. In the 1980's the home was purchased by 2 architects who added the addition in 1987. The 3 story addition blends modern amenities. This home offers lots of fun space....3-4 bedrooms, 4 full baths and 1 half bath a large kitchen with a private porch, lower level could be a great in-law, home office, or

    Mark Benard Brunet and Company Real Estate

    310 S Bigelow Rd, Hampton, CT 06247
  • /40

    $1,100,000

    • 5 Beds
    • 4 Baths
    • 5,079 Sq Ft

    76 Mill Brook Ln, Woodstock, CT 06281

    Tucked away on 6.5 private acres in the prestigious MillBrook Estates, this 5,000+ sq ft custom home offers an exceptional blend of elegance, functionality, and luxury. A long paved drive leads to this stately residence, featuring 5 bedrooms, multiple living areas, and rich architectural details throughout. The grand foyer with a hydraulic chandelier sets the tone for the craftsmanship found

    Katie Totten William Raveis Real Estate

    76 Mill Brook Ln, Woodstock, CT 06281
  • /16

    $330,000

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft

    15 Courtney Ln, Dayville, CT 06241

    Welcome to this inviting three-bedroom, one-bath ranch-style home located in the serene and picturesque "Quiet Corner" of Northeastern Connecticut. Built in 1989, this single-floor residence offers approximately 960 sq ft of thoughtfully designed living space on a tidy 0.26-acre level lot. Features a center island, elegant granite countertops, tile flooring, and ample cabinet space-perfect for

    Kathleen Brunelle First Choice Realty

    15 Courtney Ln, Dayville, CT 06241
  • /39

    $2,995,000

    • 5 Beds
    • 4.5 Baths
    • 5,977 Sq Ft

    66 Bebbington Rd, Ashford, CT 06278

    PROMINENT 55-ACRE EQUESTRIAN FACILITY w/PRIMARY 6,000SF RESIDENCE w/2 APARTMENTS! Nestled amid a peaceful countryside, this exceptional horse property presents a rare opportunity to acquire a versatile estate that seamlessly combines elegant residential living w/impressive equestrian facilities. A turnkey sanctuary for those seeking solitude, sophistication, & functionality. A private gated entry

    Kiara Rusconi William Raveis Real Estate

    66 Bebbington Rd, Ashford, CT 06278
  • /31

    $349,999

    • 5 Beds
    • 2.5 Baths
    • 1,952 Sq Ft

    240 Walnut St, Willimantic, CT 06226

    Hill Section of Willimantic, this beautifully well maintained Victorian Home at top of the hill offers rest and relaxing in quiet classic neighborhood. Many original features including pocket doors, moldings and stained glass window. Hardwood and tile throughout. 5 bedrooms, 2.5 baths, finished attic and finished basement with kitchenette and bath for in-law unit for potential rental income. 2

    Kathy Dubay I.M.A. Realty LLC

    240 Walnut St, Willimantic, CT 06226
  • /31

    $335,000

    • 2 Beds
    • 1 Bath
    • 1,409 Sq Ft

    53 Calvin Burnham Rd, Hampton, CT 06247

    Looking for a peaceful haven that combines country living with the easy access to Hartford and Providence? This property fits the bill. With two bedrooms generous storage and radiant heat, this home offers a relaxing retreat. Recent updates to the kitchen and bathroom enhanced the living experience, including new kitchen cabinets and floorings, as well as a convenient view of the living room.

    Lisa Weagle Kazantzis Real Estate, LLC

    53 Calvin Burnham Rd, Hampton, CT 06247
  • /8

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,862 Sq Ft

    64 Bailey St, Brooklyn, CT 06234

    This 3-bedroom, 2-bath contemporary home offers a great opportunity for buyers looking to add their own finishing touches. Several walls have been rebuilt, giving the home a strong structural start. The layout includes a spacious living area, updated baths, and generous bedroom sizes. It just needs some finish work to bring it to its full potential. Being sold as-is, this property is perfect

    Carolyn Bassett Remax Host of Homes

    64 Bailey St, Brooklyn, CT 06234
  • /40

    $469,000

    • 3 Beds
    • 2 Baths
    • 2,467 Sq Ft

    226 Harris Rd, Sterling, CT 06377

    Spacious Raised Ranch with Modern Comforts and Country Charm in Sterling! Welcome to this beautifully expanded 3-bedroom, 2.5-bath raised ranch nestled on over an acre of serene countryside in Sterling. This home offers a perfect blend of comfort, space, and versatility, ideal for those seeking privacy and room to grow. Step inside to find a modern tile kitchen equipped with everything you need

    Coleen Brakenwagen Jason Mitchell Real Estate Connecticut LLC

    226 Harris Rd, Sterling, CT 06377
  • /39

    $339,000

    • 4 Beds
    • 2 Baths
    • 2,218 Sq Ft

    16 Center St, Putnam, CT 06260

    Come see this wonderful & charming farmhouse style home. With a little updating/ painting this home would bring this home back to its glory. Eat in kitchen with side pantry area. First floor full bathroom. Secondary staircase to upstairs. Formal living room large enough for that oversized table, buffet, and china closet you may have. Fireplaced living room with good floors and coffered ceilings

    Robin Smith RE/MAX Bell Park Realty

    16 Center St, Putnam, CT 06260
  • /40

    $1,190,000

    • 6 Beds
    • 5 Baths
    • 4,071 Sq Ft

    349 Pomfret St, Pomfret Center, CT 06259

    349 Pomfret Street, Pomfret Center, Connecticut - Historic Charm Meets Modern Living Step into New England history with this beautifully restored property in the heart of Pomfret Center. Originally known as Stilleben Cottage, this stately home is one of just twelve original Bradley Cottages and is proudly listed on the National Register of Historic Places. Formerly the Cobscroft Inn, the

    Jennifer Mahr RE/MAX Bell Park Realty

    349 Pomfret St, Pomfret Center, CT 06259
  • /30

    $64,900

    • 2 Beds
    • 1 Bath
    • 450 Sq Ft

    91 Meadowside Rd, Woodstock, CT 06281

    Welcome to Beautiful Meadowside of Woodstock Campground, your home away from home! This is a rare opportunity to own your very own campsite along with the 1991 Mallard 38' x 140" x 12' Model with a Custom built sunroom attached located in the back of the campground. Enjoy the peace and serenity of nature. The camper is made up of 2 full/queen beds, the full bathroom is spacious with a tub, toilet

    Kerri Mullen CR Premier Properties

    91 Meadowside Rd, Woodstock, CT 06281
  • /40

    $1,220,000

    • 3 Beds
    • 3.5 Baths
    • 3,460 Sq Ft

    180 Jericho Rd, Pomfret Center, CT 06259

    A one of a kind stunning Contemporary Ranch custom built by the current owners! Set on a level 17 acre lot that has been partially cleared for recreational activities & built-in heated pool. This home is a private, quiet sanctuary for you and yours! The exterior has aggregate bricks that sparkle in the sun, limestone sills/steps, & vinyl siding in sides/back. The home was designed with an open

    Armand Colello Executive Real Estate Inc.

    180 Jericho Rd, Pomfret Center, CT 06259
  • /34

    $475,000

    • 4 Beds
    • 3 Baths
    • 2,860 Sq Ft

    144 Underwood Rd, Putnam, CT 06260

    Welcome home to this expansive 4-bedroom, 3-bathroom split-level style home which offers plenty of space and comfort! The upper level features a bright and airy living room that flows seamlessly into the kitchen and dining area. The kitchen is complete with granite countertops, stainless steel appliances, and a convenient breakfast bar. Down the hall, the expansive primary suite impresses with

    Andrew Bruce Lamacchia Realty

    144 Underwood Rd, Putnam, CT 06260
  • /32

    $350,000

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    12 John St, Danielson, CT 06239

    Welcome to your dream home, a beautifully renovated residence brimming with modern charm! This light-filled, airy home features an open-concept kitchen and dining area, perfect for entertaining. The gourmet kitchen boasts sleek granite countertops, a spacious island, and a breakfast bar. A convenient mudroom leads to the backyard and driveway, complete with a deck ideal for an above-ground pool.

    Nicholas Tomanelli Coldwell Banker Realty

    12 John St, Danielson, CT 06239
  • /28

    $289,900

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft

    34 Pleasant St, Plainfield, CT 06374

    NOTE: Units are priced to sell! These newly renovated units will not last!

    Benjamin Carbone Lamacchia Realty

    34 Pleasant St, Plainfield, CT 06374
  • /25

    $279,900

    • 3 Beds
    • 1.5 Baths
    • 1,429 Sq Ft

    34 Pleasant St Unit 8, Plainfield, CT 06374

    NOTE: Units are priced to sell! These newly renovated units will not last!

    Benjamin Carbone Lamacchia Realty

    34 Pleasant St Unit 8, Plainfield, CT 06374
  • /25

    $249,900

    • 3 Beds
    • 1.5 Baths
    • 1,259 Sq Ft

    34 Pleasant St Unit 7, Plainfield, CT 06374

    NOTE: Units are priced to sell! These newly renovated units will not last!

    Benjamin Carbone Lamacchia Realty

    34 Pleasant St Unit 7, Plainfield, CT 06374
  • /24

    $229,900

    • 2 Beds
    • 1 Bath
    • 1,215 Sq Ft

    34 Pleasant St Unit 6, Plainfield, CT 06374

    NOTE: Units are priced to sell! These newly renovated units will not last!

    Benjamin Carbone Lamacchia Realty

    34 Pleasant St Unit 6, Plainfield, CT 06374
  • /24

    $254,900

    • 2 Beds
    • 1 Bath
    • 1,343 Sq Ft

    34 Pleasant St Unit 5, Plainfield, CT 06374

    NOTE: Units are priced to sell! These newly renovated units will not last!

    Benjamin Carbone Lamacchia Realty

    34 Pleasant St Unit 5, Plainfield, CT 06374
  • /25

    $284,900

    • 3 Beds
    • 1 Bath
    • 1,314 Sq Ft

    34 Pleasant St Unit 4, Plainfield, CT 06374

    NOTE: Units are priced to sell! These newly renovated units will not last!

    Benjamin Carbone Lamacchia Realty

    34 Pleasant St Unit 4, Plainfield, CT 06374
  • /23

    $239,900

    • 2 Beds
    • 1 Bath
    • 1,188 Sq Ft

    34 Pleasant St Unit 3, Plainfield, CT 06374

    NOTE: Units are priced to sell! These newly renovated units will not last!

    Benjamin Carbone Lamacchia Realty

    34 Pleasant St Unit 3, Plainfield, CT 06374
  • /40

    $449,900

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

    23 Hell Hollow Rd, Sterling, CT 06354

    Vacation at home. Fantastic home with amazing backyard. Open dining/living room combination with breakfast bar that leads out to a Trex deck that overlooks the pool, large patio area with fire pit, and horseshoe pit. First floor laundry in updated bathroom. Walkout finished lower level has massive family room, guest room, and 1/2 bath. Solar installed 3 years ago so many years of great savings

    Alexis Devlin Coldwell Banker Realty

    23 Hell Hollow Rd, Sterling, CT 06354
  • /39

    $1,986,000

    • 4 Beds
    • 3.5 Baths
    • 5,104 Sq Ft

    175 Pulpit Rock Rd, Woodstock, CT 06281

    A once-in-a-generation opportunity. Please visit this stunning Georgian estate situated on 55 hilltop acres in desirable Woodstock, CT. Enjoy breathtaking long views all the way to Rhode Island! A few of the exceptional assets offered include an elegant in-law apartment, a large 6 stall horse barn with office, an inviting in-ground pool, and 25 acres of fenced open pasture. As you approach the

    John Downs Berkshire Hathaway NE Prop.

    175 Pulpit Rock Rd, Woodstock, CT 06281
  • /37

    $399,999

    • 3 Beds
    • 1.5 Baths
    • 1,922 Sq Ft

    3 Woodstock Ave W, Putnam, CT 06260

    This character-filled home sits on a private and generous 1.39-acre lot-offering room to breathe, space to grow, and plenty of possibilities. With 1,922 square feet, this 3-bedroom, 1.5 bath residence is move-in ready and full of potential for the right buyer with vision and energy. Durable HardiePlank fiber cement siding wraps the home in timeless style and long-term protection-resisting

    Beth Fournier Compass Connecticut, LLC

    3 Woodstock Ave W, Putnam, CT 06260
  • /23

    $29,900

    • 1 Bed
    • 1 Bath
    • 300 Sq Ft

    25 Route 197 Unit Lot 40, Woodstock, CT 06281

    Price Improvement! Welcome to your home away from home! This is your opportunity to own your very own campsite located in in the beautiful Meadowside of Woodstock community! Included is a 1995 33' Corsica Cobra 30BH trailer that has been well cared for. The trailer has a queen bed and a bunk room with two additional sleeping bunks, a full bath with a standup shower and an eat-in kitchen. There is

    Keri Roy Kazantzis Real Estate, LLC

    25 Route 197 Unit Lot 40, Woodstock, CT 06281
  • /4

    $465,000

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

    50 High St, Moosup, CT 06354

    This expansive Cape Cod-style home is a hidden gem, situated on 2.72 acres with a wraparound driveway complemented by an additional parking area. The two-car garage is located beneath the house, and the home features spacious rooms with ample storage throughout. The dining room boasts a beautiful fieldstone fireplace, while the bar area is carpeted wall-to-wall. The kitchen offers abundant

    Liz Lavallee Dawn Taylor Real Estate

    50 High St, Moosup, CT 06354
  • /39

    $419,900

    • 3 Beds
    • 2 Baths
    • 1,892 Sq Ft

    13 Foster St, Danielson, CT 06239

    Charming 3-Bedroom Raised Ranch - Fully Renovated! Move right into this beautifully updated 3-bedroom, 2-bathroom raised ranch, offering modern finishes and a spacious layout. The interior has been recently renovated and features fresh paint and all-new vinyl plank flooring throughout. The brand-new kitchen is a showstopper with new cabinets, sleek quartz countertops, and new stainless steel

    Tanya McDermott Berkshire Hathaway NE Prop.

    13 Foster St, Danielson, CT 06239
  • /7

    $499,900 Coming Soon

    • 3 Beds
    • 3 Baths
    • 3,024 Sq Ft

    15 Highview Dr, Dayville, CT 06241

    Welcome to Zadora Heights! Spacious colonial style home with 3-5 bedrooms, 3 full bathrooms and 3024 sqft. This freshly painted home features updated lighting, hardwood floors, living room with a wood burning fireplace, updated kitchen and baths. The partially finished walkout basement, with a full bath, offers plenty of additional space for either a large family room, space for large workout

    Christine Costa Kazantzis Real Estate, LLC

    15 Highview Dr, Dayville, CT 06241
  • /38

    $399,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 2,591 Sq Ft

    141 Old Town Rd, Ashford, CT 06278

    GORGEOUS AND READY FOR SUMMER FUN! The sparkling water of the 16x32 inground pool is calling you! This fabulous Cape features an updated kitchen with grey cabinets, gas stove, stainless steel appliances, QUARTZ counters and tile backsplash! The dining area is open to the living room with vaulted ceiling, fireplace and refinished hardwood floors. With a 1st floor bedroom and full bath, this home

    Tracy Wagner Rockoff Realty

    141 Old Town Rd, Ashford, CT 06278
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