Homes for Sale near Pomperaug Regional High School

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  /38

  $599,000

  • 4 Beds
  • 3.5 Baths
  • 2,691 Sq Ft

  66 Artillery Rd, Middlebury, CT 06762

  Antique lovers alert! Enjoy this quintessential 1803 Colonial on 1.026 acres, nestled within the picturesque conservation protected 7.3 acre land containing Fenn Pond. You'll own a piece of history, with the privacy, character and tradition of its era, including wide board floors, 7 fireplaces, and front and back staircases. Delightful finds everywhere! The magical setting contains stone walls,

  Mary Helen Levine Mary Helen Levine Real Estate LLC

  66 Artillery Rd, Middlebury, CT 06762
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  /28

  $721,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,290 Sq Ft

  3 Pine Ridge Unit 23, Middlebury, CT 06762

  Welcome to Granite Woods - 2024 HOBI Award Winner for Best Detached 55+ Community. Only six homes remain in this in-town neighborhood featuring 24 detached Cape-style homes in the heart of Middlebury Village. Enjoy the peace, privacy, and independence of a stand-alone home with no shared walls, all within a low-maintenance community designed for active 55+ living. Ideally located, Granite Woods

  Robert Michaud Michaud Real Estate

  3 Pine Ridge Unit 23, Middlebury, CT 06762
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  /23

  $619,000 New Construction

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft

  1 Pine Ridge Unit 24, Middlebury, CT 06762

  Welcome to Granite Woods - 2024 HOBI Award Winner for Best Detached 55+ Community. Only six homes remain in this in-town neighborhood featuring 24 detached Cape-style homes in the heart of Middlebury Village. Enjoy the peace, privacy, and independence of a stand-alone home with no shared walls, all within a low-maintenance community designed for active 55+ living. Ideally located, Granite Woods

  Robert Michaud Michaud Real Estate

  1 Pine Ridge Unit 24, Middlebury, CT 06762
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  /2

  $675,000 Open Sat 10AM - 1PM

  • 2 Beds
  • 2.5 Baths
  • 3,144 Sq Ft

  732 Hulls Hill Rd, Southbury, CT 06488

  Welcome to 732 Hulls Hill Road! This unique contemporary is truly one of Southbury's hidden gems. Built in 2016, this thoughtfully designed 2-3 bedroom, 2-bath home blends modern comfort with elegant style, perfect for both entertaining and everyday living. Step inside to discover stunning natural wood details, soaring ceilings, a bright and open layout. The heart of the home is the chef's

  Michelle Pavia William Raveis Real Estate

  732 Hulls Hill Rd, Southbury, CT 06488
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  /36

  $345,000 Open Sat 1PM - 3PM

  • 2 Beds
  • 2.5 Baths
  • 1,298 Sq Ft

  26 Far View Commons Unit 26, Southbury, CT 06488

  Beautifully updated 2BR, 2.5BA unit townhouse in Far View Commons! This move-in-ready home offers a bright, open floor plan with hardwood floors, and abundant natural light and a cozy wood-burning fireplace. Enjoy peace and privacy from the oversized rear deck, which backs directly onto the scenic Larkin State Bridle Trail-ideal for walking, biking, or enjoying nature. Upstairs, the primary

  Carla Moreira Keller Williams Realty

  26 Far View Commons Unit 26, Southbury, CT 06488
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  /26

  $375,000 Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,432 Sq Ft

  699 Woodvale Dr Unit B, Southbury, CT 06488

  This beautiful bright and sunny Sherman model is nestled privately in a small cluster on Woodvale Drive. In the winter, you can see the 13th tee of the nearby golf course, but in summer privacy prevails on the large deck. Lovely landscaping at the entrance. Updated kitchen with stainless steel appliances and large eating area. Elegant dining area at the end of the living room, both overlooking

  Joan King William Raveis Real Estate

  699 Woodvale Dr Unit B, Southbury, CT 06488
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  /31

  $624,900 Open Sat 12PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,560 Sq Ft

  297 Whittemore Rd, Middlebury, CT 06762

  This well maintained home offers lots of space for the expanding family or simply one level living for the downsizer with guests to entertain. Truly a MUST SEE! Remodeled kitchen, gleaming oak floors, fireplaced dining room for those traditional holidays. Large Open Great Room with lots of Natural Sunlight. Full Walk Up Attic for possible expansion if needed. Lower level boasts a full bathroom

  Susan Belmonte Coldwell Banker Realty

  297 Whittemore Rd, Middlebury, CT 06762
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  /8

  $216,000

  • Land
  • 1.04 Acres
  • $207,692 per Acre

  28 Pine Hollow Dr, Middlebury, CT 06762

  Non-conforming conforming two Barns on property.

  Derek Greene Derek Greene

  28 Pine Hollow Dr, Middlebury, CT 06762
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  /37

  $660,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  6 Brookside Dr, Middlebury, CT 06762

  Welcome to 6 Brookside Drive in Middlebury, CT-a beautifully maintained 3,745 sq ft colonial-style home in the desirable Brookside subdivision. This versatile residence offers 4 bedrooms and 4 bathrooms across three finished levels, ideal for multigenerational living. The open-concept main floor features vaulted ceilings, a gas fireplace, a gourmet eat-in kitchen with smart appliances, and a

  Nutan Pawar DreamHomes Realty LLC

  6 Brookside Dr, Middlebury, CT 06762
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  /40

  $225,000

  • 1 Bed
  • 1 Bath
  • 928 Sq Ft

  504 Heritage Village Unit A, Southbury, CT 06488

  Experience the exceptional offerings of Heritage Village, a vibrant 55+ Active Adult community, in this affordable, conveniently located 1-bedroom, 1-bath Carriage House-model. This model has the lowest HOA fees in the community. Highlights include: A no-step walk from the garage/parking areas to the unit, with plenty of nearby guest parking. Custom window blinds are installed on the newer

  Wendy Kudej Coldwell Banker Realty

  504 Heritage Village Unit A, Southbury, CT 06488
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  /16

  $389,900

  • 3 Beds
  • 1 Bath
  • 1,327 Sq Ft

  215 White Birch Dr, Southbury, CT 06488

  Charming 3-bedroom ranch on quiet dead-end street. This one level living home features central air, a cozy fireplace and a jetted bathtub. Enjoy the spacious, private backyard with two decks, perfect for relaxing or entertaining. It is located a short distance to all of Southbury's great shopping and a movie theater. It is walking distance to Lake Zoar. Great commute to New York via I-84, Exit

  Joyce Skowronski Joyce M.Skowronski,R.E. Broker

  215 White Birch Dr, Southbury, CT 06488
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  /33

  $549,900

  • 3 Beds
  • 2.5 Baths
  • 2,160 Sq Ft

  110 Glenwood Ave, Middlebury, CT 06762

  Nestled on a private, set-back lot surrounded by beautifully landscaped gardens, this classic 3-bedroom Colonial offers timeless appeal and modern comfort. A welcoming country-style front porch invites you inside, where a dramatic two-story foyer sets the tone. To your right, a flexible formal living room or a convenient spot for a home office, complete with elegant French doors leading to the

  Christina Zainc BHGRE Bannon & Hebert

  110 Glenwood Ave, Middlebury, CT 06762
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  /13

  $319,000

  • 2 Beds
  • 1 Bath
  • 942 Sq Ft

  7 Greenwich Dr, Southbury, CT 06488

  Welcome to 7 Greenwich Drive, a charming ranch-style home nestled in a quiet Southbury neighborhood. This well-maintained 2-bedroom, 1-bath home offers 942 square feet of comfortable living space, set on nearly half an acre. This home features a functional layout with spacious bedrooms and a bright living area. Enjoy peaceful outdoor living on your private patio, with plenty of additional space

  Alex Camargo eXp Realty

  7 Greenwich Dr, Southbury, CT 06488
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  /30

  $499,000

  • 4 Beds
  • 3 Baths
  • 2,438 Sq Ft

  306 Brown Brook Rd, Southbury, CT 06488

  Charming Cape in Sought-After Purchase Neighborhood of Southbury! Tucked away in a quiet, private setting on 1.45 acres, this 4-bedroom, 3-bath Cape-style home offers the perfect blend of space, flexibility, and potential. Located in the desirable Purchase neighborhood of Southbury, this property is a rare find for buyers seeking peace, privacy, and the chance to make a home their own. The layout

  Jonna Dibble BHGRE Bannon & Hebert

  306 Brown Brook Rd, Southbury, CT 06488
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  /35

  $279,000

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  664 Heritage Village, Southbury, CT 06488

  Move in ready & ready for entertaining, this Hawthorne awaits its new owners. You'll be wowed by the fully renovated, fully applianced dream kitchen where the wall between the kitchen & great room was opened up to give you max storage in the lower cabinets while allowing the flow of air, light & conversation between the two rooms. The focal point is the fireplace with its economical propane

  Ruth Zeiss William Raveis Real Estate

  664 Heritage Village, Southbury, CT 06488
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  /2

  $699,900

  • Land
  • 6 Acres
  • $116,070 per Acre

  Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762

  This is an exceptional opportunity to create your dream home in an area of fine homes. Three lots, sold as a package, provide over six acres of stunning land in one of Middlebury's most desirable neighborhoods. Extending the road will be necessary for the three separate lots unless they are combined into a single parcel. Enjoy picturesque views of Mirey Pond.

  Mary Ann Hebert BHGRE Bannon & Hebert

  Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762
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  /28

  $300,000

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  669 Heritage Village Unit B, Southbury, CT 06488

  Come see this beautifully renovated and move in ready "Hawthorne" Model, with 2-Bedrooms, 2-Full Bathrooms on a single level. This home was completely renovated less than three years ago, with new flooring, cabinetry, countertops, showers, and appliances. In addition, an energy efficient split heating/cooling system has been installed in the home with three separate zones. The home is just a

  Scott Hellriegel Berkshire Hathaway NE Prop.

  669 Heritage Village Unit B, Southbury, CT 06488
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  /29

  $219,000 Open Mon 1PM - 3PM

  • 1 Bed
  • 1 Bath
  • 928 Sq Ft

  79 Heritage Village Unit B, Southbury, CT 06488

  Turnkey Carriage House in serene Heritage Village - 55+ Living at Its Finest! Move right in and make it your own! This beautifully maintained Carriage House, nestled in a quiet corner of the sought-after 55+ Heritage Village, is freshly painted in neutral tones-ready for your personal touch. Step onto the secluded side deck and enjoy peaceful mornings with nothing but birdsong in the background.

  Gabby Addison Keller Williams Realty

  79 Heritage Village Unit B, Southbury, CT 06488
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  /2

  $85,000

  • Land
  • 0.45 Acre
  • $188,889 per Acre

  440 Lake Shore Dr, Middlebury, CT 06762

  Build your dream cottage on this waterfront building lot on the desirable Long Meadow Pond. The lot is located near the end of a low traffic cul-de-sac. It is a great opportunity

  Florence DeDampierre W. Raveis Lifestyles Realty

  440 Lake Shore Dr, Middlebury, CT 06762
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  /15

  $315,000

  • 2 Beds
  • 2 Baths
  • 1,071 Sq Ft

  9 Heritage Cir Unit D, Southbury, CT 06488

  All ages welcome! Located in the desirable community of Heritage Circle, this Hawthorne model offers both functionality and an open feel. The spacious dining area is great for hosting, while the living room features a fireplace for cozy evenings at home. An eat-in kitchen provides a casual space for everyday meals, and two bedrooms and two full bathrooms offer flexibility for guests, a home

  Lori Parr Berkshire Hathaway NE Prop.

  9 Heritage Cir Unit D, Southbury, CT 06488
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  /15

  $449,900

  • 4 Beds
  • 1.5 Baths
  • 1,904 Sq Ft

  88 W Purchase Rd, Southbury, CT 06488

  Opportunity knocks! Very spacious 4 bedroom house with 1 1/2 baths and almost 2000 sq ft, oversized bedrooms, huge living room with eat-in kitchen. This house has over 2 acres and is set back on a beautiful country road, surrounded by stonewalls and has the feeling of old New England. Sit out on the open stone patio or if you want some shade or the weather is bad there is a covered area.

  Lisa Sader-Goede Aspen Realty Group

  88 W Purchase Rd, Southbury, CT 06488
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  /22

  $549,900

  • 3 Beds
  • 2 Baths
  • 1,847 Sq Ft

  11 Heritage Crest Unit B, Southbury, CT 06488

  Highly desirable 3 bedroom, 2 bathroom, "Roxbury" style condo with attached 2 car garage! Heritage Crest is a delightful, all-ages community of roughly 100 homes offering amenities including an inground pool and tennis court. Stylish modern renovation of the kitchen which includes contrasting cabinets, granite counters, black appliances and a peninsula with electric cooktop. The living and dining

  Frank Cass Joseph Bette REALTORS Inc

  11 Heritage Crest Unit B, Southbury, CT 06488
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  /40

  $289,900

  • 1 Bed
  • 1 Bath
  • 928 Sq Ft

  953 Heritage Village Unit A, Southbury, CT 06488

  Spacious Carriage House model located in award winning Heritage Village, a 55+ community in a peaceful country setting, yet close to shopping and activities. Beautifully renovated 1 BR/ 1 bath Ranch unit. This unit has been tastefully redone with a new kitchen including cabinets, granite countertops, porcelain tile floor and new appliances. Walk in shower with glass sliding doors, tile walls and

  Paul Duh Realty ONE Group Connect

  953 Heritage Village Unit A, Southbury, CT 06488
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  /30

  $265,000

  • 2 Beds
  • 2 Baths
  • 1,044 Sq Ft

  231 Heritage Village Unit C, Southbury, CT 06488

  Come see this amazing "Ethan Allen" Model, with 2 beds, 2 full baths, and some of the best views the community has to offer. The unit is peaceful and ready for you to move right in, with newly updated flooring, cabinetry, and counter tops throughout. The unit holds the perfect amount of well-lit space, with a spectacular sights of the golf course and town from your private balcony or bay window.

  Scott Hellriegel Berkshire Hathaway NE Prop.

  231 Heritage Village Unit C, Southbury, CT 06488
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  /36

  $439,000

  • 2 Beds
  • 2 Baths
  • 1,432 Sq Ft

  106 Heritage Village Unit A, Southbury, CT 06488

  Welcome to your new home, a fabulous mix of elegance, style, and convenience. This 2- bedroom, 2-full bath Sherman model unit has been completely renovated with the latest conveniences and quality, high-end finishes. This unit is all about ease of living, from its short, flat walk from the garage to the front door, to the nearby guest parking, to the many thoughtful updates you will find inside.

  Jacqueline Ruppert Berkshire Hathaway NE Prop.

  106 Heritage Village Unit A, Southbury, CT 06488
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  /39

  $550,000

  • 3 Beds
  • 3 Baths
  • 2,696 Sq Ft

  175 W View Rd, Southbury, CT 06488

  The one you have waited for is here! Fantastic single level with lower level in-law potential! Beautiful, spacious and updated three-bedroom, three full bath Ranch with wonderful open floor plan is perfectly set back on a quiet cul-de-sac near the Southford Falls park. The exterior of the home was professionally painted in 2022 and the mechanicals have been updated and regularly serviced. In 2022

  Renee Mascia RE/MAX Right Choice

  175 W View Rd, Southbury, CT 06488
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  /27

  $319,000

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  15 Midland Trail, Southbury, CT 06488

  Welcome to this charming Cape-style home, ideally situated just minutes from I-84, offering unbeatable convenience for commuting and easy access to local shopping, dining, and entertainment. This cozy 2-bedroom, 1-bathroom home features an updated kitchen, an inviting living space filled with natural light, and a private covered deck perfect for relaxing outdoors.The under-house garage provides

  Shawna Mucherino Coldwell Banker Realty

  15 Midland Trail, Southbury, CT 06488
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  /31

  $739,900

  • 4 Beds
  • 3 Baths
  • 2,764 Sq Ft

  110 Silver Beech Rd, Southbury, CT 06488

  LOCATION, LOCATION, LOCATION! Nestled on a spacious 1.39-acre lot in a quiet cul-de-sac, this lovingly maintained home is just minutes from local and state parks, scenic trails, and outdoor recreation. Owned by the same family for 35 years-only the second owners-this property exudes pride of ownership throughout. The first floor features a bright, spacious living room with fireplace, a formal

  Nancy Langrock William Raveis Real Estate

  110 Silver Beech Rd, Southbury, CT 06488
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  /39

  $995,000

  • 4 Beds
  • 3.5 Baths
  • 4,496 Sq Ft

  593 Park Road Extension, Middlebury, CT 06762

  This spacious, custom built home sits on a 6+ acre lot with a large garden area & a barn with 2 garage doors, loft area & an attached green house! The main house features a grand foyer with granite flooring, a very large, formal dining room & a generous sized formal living room/music room. The eat-in kitchen area is large enough to hold an 8 seat table & chairs & has slider access to the deck.

  Jackie Desmarais Showcase Realty, Inc.

  593 Park Road Extension, Middlebury, CT 06762
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  /24

  $515,000

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

  43 Ridgewood Dr Unit 43, Middlebury, CT 06762

  Enjoy living a relaxing and luxurious lifestyle in a most desirable community. As you step into this beautifully appointed, light filled townhome, you can appreciate the open floorplan. This Portman model offers hardwood flooring on the main level and features an eat-in kitchen open to the living/dining room with a gas fireplace for ambiance and warmth. Accessible from the kitchen dining area,

  Donna Bannon BHGRE Bannon & Hebert

  43 Ridgewood Dr Unit 43, Middlebury, CT 06762
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  /26

  $200,000

  • 1 Bed
  • 1 Bath
  • 928 Sq Ft

  917 Heritage Village Unit B, Southbury, CT 06488

  This Carriage House Model has a 1 Bedroom, 1 Bathroom primary suite, spacious living room with fireplace, bay window seats, and cozy deck. This is a one-of-a-kind location in the desirable Hilltop area of Heritage Village with a short, flat walk to the from door, and ample guest parking nearby. A rare find. From this location, you're just a short walk to the pool, pickleball courts, tennis court,

  Scott Hellriegel Berkshire Hathaway NE Prop.

  917 Heritage Village Unit B, Southbury, CT 06488
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  /40

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft

  115 Marney Dr, Middlebury, CT 06762

  Welcome to 115 Marney Drive! This spacious split level home has so much to offer to a family of any size! Not only does it have 3 bedrooms and 2.5 baths, it also has a large living room and dining area great for entertainment. The lower level has a finished bedroom and den with fireplace for additional guests. This house has had many updates since 2018 including a new roof and gutters with gutter

  Allysa DeRosa Mapleridge Realty

  115 Marney Dr, Middlebury, CT 06762
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  /40

  $259,900 Open Thu 5PM - 6:30PM

  • 3 Beds
  • 2 Baths
  • 1,348 Sq Ft

  197 Lee Farm Dr, Southbury, CT 06488

  Wonderful lakeside Lifestyle! Sit On The Dock, Fish, Boat, Swim, Skate, Relax! Dappled View Of Lake Zoar. Level lawn, room for garden. Pleasant Central Air. Lower level living suite with full bath, private entrance to patio, peek-a view of the water. Enjoy Life! Walk to neighborhood playground. Rent out the Veteran's Hall for your party of 60. Easy to Lake Zoar Boat Launch. Savor the fabulous

  Joel Matson Divine Realty, LLC

  197 Lee Farm Dr, Southbury, CT 06488
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  /16

  $239,900 Open Thu 5PM - 6:30PM

  • 2 Beds
  • 1 Bath
  • 968 Sq Ft

  203 Lee Farm Dr, Southbury, CT 06488

  Enjoy your waterside retreat. Charming Lake Zoar setting. Enjoy the sweet Southbury lifestyle. Go eagle-spotting at Shepaug Dam, Camping at Kettletown State Park. Picnicking at Southford Falls State Park. Hiking at Waldo State Park. Dobbin and you amble the bridle trails at Larkin State Park. Excellent library, fine Heritage Village Golf. World class antiquing. Marvelous Region 15 schools. Good

  Joel Matson Divine Realty, LLC

  203 Lee Farm Dr, Southbury, CT 06488
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  /17

  $419,900

  • 2 Beds
  • 2 Baths
  • 1,398 Sq Ft

  128 Heritage Village Unit A, Southbury, CT 06488

  Move right into this beautifully Remodeled Country House unit. The Open Floor Plan is perfect for entertaining family and friends. Living room has a Custom Fireplace with an Electric insert - New ceiling fan and Window seat . Large Dining area with New fixture and Sliders leading to Private Extended I kPatio. Remodeled Kitchen with Quartz counters - New lighting fixtures - Two unique ceiling fans

  Joan Oricchio Berkshire Hathaway NE Prop.

  128 Heritage Village Unit A, Southbury, CT 06488
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  /37

  $560,000

  • 3 Beds
  • 2.5 Baths
  • 2,122 Sq Ft

  39 Ridgewood Dr Unit 39, Middlebury, CT 06762

  Luxury living in this stunning 2122+ SqFt Portman ELITE END unit in sought Ridgewood community. This 3-bed, 2.5-bath home boasts exquisite upgrades, including a 3-foot extended bump out on both floors, hardwood floors, 9-ft ceilings, recessed lighting, custom crown, chair trail and mantle molding w/ custom beams. The open floor plan brings tons of natural light, offering serene forest views. The

  Jay Irvine Serhant Connecticut, LLC

  39 Ridgewood Dr Unit 39, Middlebury, CT 06762
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  /40

  $725,000

  • 3 Beds
  • 2.5 Baths
  • 2,628 Sq Ft

  49 Kettletown Woods Rd, Southbury, CT 06488

  Discover the charming Colonial in Southbury that you've been searching for! This beautifully bright and meticulously maintained home is nestled in a peaceful cul-de-sac neighborhood in a prime location in town. Offering a perfect combination of space, privacy, and comfort, it's the ideal place to call home. The spacious family room features vaulted ceilings with exposed beams, multiple skylights,

  Scott Hellriegel Berkshire Hathaway NE Prop.

  49 Kettletown Woods Rd, Southbury, CT 06488
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  /28

  $589,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 3 Baths
  • 2,088 Sq Ft

  76 Three Mile Hill Rd, Middlebury, CT 06762

  Meticulously maintained and completely renovated in 2024, this move-in-ready home is a true masterpiece of thoughtful design. Located in one of Middlebury's most desirable neighborhoods, this 4 bedroom, 3 full bath home is a gem not to be missed. From the moment you step inside, you feel the warmth and coziness of the home combined with the ease of modern living. The updated kitchen boasts

  Lisa Clarke Dave Jones Realty, LLC

  76 Three Mile Hill Rd, Middlebury, CT 06762
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  /34

  $640,000

  • 3 Beds
  • 3.5 Baths
  • 3,477 Sq Ft

  1 Dogwood Ct Unit 1, Middlebury, CT 06762

  Wow-this is it! The original model home is back on the market for the first time, offering exceptional quality and design. This desirable Dickinson-style home, originally built as the model, is impeccably finished on all three levels. The spacious dining area flows seamlessly into a vaulted living room with a cozy fireplace and sliders leading to a private deck. The light-filled kitchen features

  Joyce Drakeley Drakeley Real Estate, Inc.

  1 Dogwood Ct Unit 1, Middlebury, CT 06762
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  /28

  $279,000

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft

  405 Heritage Village Unit B, Southbury, CT 06488

  It's time to make life a little easier. Move right into this Krueger pond, Heritage-model condo set in the vibrant, Heritage Village 55+ community. This meticulously-kept end unit features 2 generously-sized bedrooms and 2 full bathrooms. Gleaming, luxury vinyl plank is easy-to-maintain and showcased throughout most of the home. The spacious living and dining area is equipped with a cozy, gas

  Leah Schroeder KW Legacy Partners

  405 Heritage Village Unit B, Southbury, CT 06488

Showing Results 41 - 80, Page 2 of 4