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$602,500
4 Beds ⋅ 3 Baths ⋅ 24155964 MLS
Large Colonial with charm and character ready to call home! Offering privacy on its fabulous 4 acres with magical views and abundant sunlight. The home offers four large bedrooms with ample light that will surely please. The formal living room complete with a large picture window and marble fireplace will serve as a great place to relax at the end of a long day. The dining room is ready to host any event you plan, and has the space to welcome everyone over for dinner without scrambling for additional space. The eat in kitchen has 3 ovens and plenty of space to meal prep. The home also offers a den/study with a wet bar to gather in a relaxed environment or curl up to a book or cocktail. The Florida Room (Sunroom) is heated and has 2 sliders to the outdoors. Such a fun room to take in the views. Roof is 6 years old, and the chimneys have been repointed in the last 5 years.

321 Artillery Rd, Middlebury
$600,000
4 Beds ⋅ 3 Baths ⋅ 24131536 MLS
A grand Cape Cod-style home, nestled in a wonderful and convenient neighborhood. The interior has been freshly painted, and the main level features primarily hardwood flooring. Just off the foyer, you'll find a sunken living room that welcomes you. The spacious eat-in kitchen has been remodeled and opens to the formal dining room, making it perfect for entertaining. Adjacent to the kitchen is a cozy den, complete with a wood-burning fireplace, built-ins, and a skylight to bring in natural light. The primary bedroom suite, located on the main level, boasts a large walk-in closet, a full bath, and a sliding door that leads to a private deck. A second bedroom and another full bath are also conveniently situated on this level. Upstairs, you'll discover two generously sized bedrooms and a third full bathroom. The outdoor space features a multi-level deck, part of which is a screened-in porch, perfect for enjoying the wooded backyard. The basement offers ample storage and additional finished space. Recent upgrades include a new roof and central A/C compressor.

72 Carriage Dr, Middlebury
$600,000
4 Beds ⋅ 4 Baths ⋅ 24106017 MLS ⋅ Brookside BLDG.
Set your eyes on this gorgeous home which features 4 bedrooms, 2 full baths & 2 1/2 baths in Middlebury! This beautifully maintained home boasts classic architecture with modern updates, offering the perfect blend of charm and sophistication. You are welcomed as you enter through the front door by a beautiful family room with charming fireplace and high ceilings. From the family room you have an exceptional view of the beautiful kitchen which features beautiful countertops, ample cabinetry, island and stainless-steel appliances. Size of kitchen allows for table for every night dinners. Step into exquisite dining room which features beautiful decor with crown moldings. Layout of dining room is perfect for those holiday events and special occasions. Home office on main floor offers the perfect space for remote work or study. Beautiful hardwood floors on main level. Upstairs, you'll find four spacious bedrooms and 2 full bathrooms, perfect for family living. Each room offers ample natural light, generous closet space, and spacious layouts to suit your needs. Primary bedroom offers a perfect retreat with generous space and luxurious features. It boasts a large, comfortable layout with ample natural light streaming through both windows. Finished basement offers additional living space that enhances the overall appeal of the home. It includes a cozy family or media room, a dedicated recreation area, and ample storage options. A must see!

39 Independence Cir Unit 39, Middlebury
$600,000
4 Beds ⋅ 4 Baths ⋅ 24061887 MLS ⋅ Ridgewood BLDG.
Stunning Luxury Townhome in the Desirable Ridgewood Community. Beautifully upgraded 3/4-bedroom, 3.5-bathroom end-unit townhome with a 2-car garage, offering approximately 3,000 sq. ft. of luxurious living space. Enjoy the private yard, walk-out deck with all the enhancements, this home has more space than you can imagine. The main floor features an open-concept layout with oak floors, a spacious dining area, and a living room with a cozy gas fireplace. The eat-in kitchen is a chef's dream, boasting cherry wood cabinets, granite counters, a tile backsplash, and new WiFi-enabled LG stainless steel appliances. Step onto the back deck with its upgraded electric awning-perfect for relaxing or entertaining.Hardwood flrs on main flr. Upstairs, hardwood floors, the primary suite has been fully remodeled to perfection. The brand-new primary bath has a luxurious shower with double shower heads, a new double vanity, updated lighting, and stunning new tile floor. The custom-built walk-in closet offers ample storage. Two additional bedrooms, including one with a walk-in closet, and a shared bath with brand new shower/tub. The versatile loft with skylights can serve as a fourth bedroom or flex space. The finished basement offers a media/entertainment room, a fourth bedroom, and a remodeled full bath. Additional updates include a new WiFi water heater, new AC compressor, and new furnace. Turn-key home with premium upgrades, literally no maintenance. Newer paint throughout home. move o

6 Ridgewood Dr Unit 6, Middlebury
$599,900
2 Beds ⋅ 2 Baths ⋅ 24155123 MLS
Set on more than 4 peaceful, pastoral acres, this beautifully remodeled ranch offers the ideal blend of character, craftsmanship, and modern comfort. Lovingly restored during the owner's tenure, the home showcases thoughtful upgrades and timeless details throughout. A newly built oversized two car garage provides excellent storage and convenience. Inside, the custom kitchen-designed and crafted by Bushka Lumber & Millwork-anchors the heart of the home with exceptional quality and style. The adjoining dining area features the original stone bread oven, adding warmth and authenticity to the space. The great room is centered around a striking stone fireplace, creating a welcoming gathering place in every season. A three season sunroom extends the living area and invites you to enjoy the surrounding landscape-no curtains needed, just uninterrupted views of nature. The primary bedroom, originally two separate rooms, offers generous space and flexibility. Additional updates include newer mechanicals and new cedar siding on three sides, ensuring both comfort and longevity. A rare opportunity to own a true country retreat with craftsmanship, acreage, and privacy-all within desirable Middlebury.

428 Breakneck Hill Rd, Middlebury
$596,565
2 Beds ⋅ 2 Baths ⋅ 170591017 MLS ⋅ Granite Woods BLDG.
Welcome to Granite Woods, a unique, brand new in-town 55+ home community featuring 24 Cape-style classic homes in the heart of tranquil Middlebury Village, walkable to restaurants, coffee shops, shopping, and direct access to the popular Middlebury Greenway Trail. Phase One is currently underway offering five unique designs that make living in style easy for years of family enjoyment while emphasizing the ease of aging in place, with no step front entries and wide interior door openings. Amenities include a for-residents-only pickleball court, shuffleboard, and pavilion. The Birch features a New England-styled portico, single-story living with an open concept that inspires you to entertain. Two owner’s suites provide many options. The sunlit great room with a fireplace is perfect for family gatherings. The first of two owner’s suites complete with a walk-in closet and a handy mudroom with a bench seat with an adjacent laundry room complete the first floor. Second-floor options include an additional guest suite, and a loft, or a loft with an additional hobby space. The beauty, craftsmanship, customization, and attention to detail these homes offer, along with Award Winning Builders' project expertise, will ensure an enjoyable experience and future at Granite Woods. Nothing is as rewarding as customizing your home, let’s work together to make your dream home a reality! Alternate Plans Available!! Property owners have a Real Estate License

9 Oakwood Dr Unit 5, Middlebury
$595,000
3 Beds ⋅ 3 Baths ⋅ 24077750 MLS ⋅ Ridgewood At Middlebury BLDG.
Hickory Elite End-Unit Townhouse in sought after Ridgewood at Middlebury, nestled on a quiet cul-de-sac.Offering a blend of luxury, convenience, & top-tier amenities, this 3-bdrm, 3-ba home is designed for both comfort & style.As you step inside, rich dark hdwd flooring flows seamlessly thruout the main living areas, setting a tone of elegance.The expansive 2-story living & dining area is bathed in natural light, enhanced by Hunter Douglas window treatments for privacy & ambiance.At the heart of the home is the gourmet kitchen, featuring pristine white cabinetry, granite countertops, & high-end stainless steel appliances.Designed for both functionality & aesthetics, the kitchen opens to the inviting family rm, complete with a cozy gas fireplace-the perfect space for gatherings. With a 4 ft bumpout, french doors lead to the oversized patio with natural gas line grill, where you can relax and take in stunning sunset views while entertaining guests. The first-floor master bdrm is a serene retreat, boasting a spa-like ensuite bathrm & a spacious walk-in closet.A convenient main-level laundry rm adds to the ease of living along w/ a Generac generator for peace of mind during power outages.Upstairs, the loft area, along w/ 2 add'l bdrms and a full ba, provides privacy & comfort for family members or guests.The fully fin basement w/ sump pump is a standout feature, offering versatile space for a home theater, gym, or recreation room-truly setting this home apart.Schedule your tour!

7 Highridge Rd Unit 7, Middlebury
$593,360
3 Beds ⋅ 3 Baths ⋅ 24066786 MLS ⋅ Aberdeen Estates At Benson Woods BLDG.
An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. Unit 40 is an End Unit. Model unit coming Spring 2025. Phase 1 occupancy starting Summer 2025. Now taking deposits on Phase 2! A Planned Unit Development (PUD) - Built by Lovley Development, Inc. / Developed by Newport Realty Group. Agent related.

North Benson Rd Unit 40, Middlebury
$591,700
2 Beds ⋅ 2 Baths ⋅ 170547651 MLS ⋅ Granite Woods BLDG.
Welcome to Granite Woods, a unique, brand new in-town 55+ home community featuring 24 Cape-style classic homes in the heart of tranquil Middlebury Village, walkable to restaurants, coffee shops, shopping, and direct access to the popular Middlebury Greenway Trail. Phase One is currently underway offering five unique designs that make living in style easy for years of family enjoyment while emphasizing the ease of aging in place, with no step front entries and wide interior door openings. Amenities include a for-residents-only pickleball court, shuffleboard, and pavilion. The Willow offers a quaint-covered porch and single-story living with an open concept that inspires you to entertain. Two owner’s suites and an optional flex space provide many options. The bright sunlit great room with a fireplace is the perfect location for family gatherings and the first of two owners’ suites is complete with a walk-in closet. A mudroom with a bench seat and adjacent laundry room complete the first-floor. Second-floor options include an additional guest suite with a loft, or a loft with an additional hobby space. The beauty, craftsmanship, customization, and attention to detail these homes offer, along with Award Winning Builders' project expertise, will ensure an enjoyable experience and future at Granite Woods. Nothing is as rewarding as customizing your home, let’s work together to make your dream home a reality! Alternate Plans Available!! Property owners have a Real Estate License

15 Oakwood Dr Unit 8, Middlebury
$591,251
3 Beds ⋅ 3 Baths ⋅ 24070506 MLS ⋅ Aberdeen Estates At Benson Woods BLDG.
An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. Unit 35 is an End Unit. Phase 1 occupancy starting Summer 2025. Now taking deposits on Phase 2. Model unit coming Spring 2025! A Planned Unit Development (PUD) - Built by Lovley Development, Inc. / Developed by Newport Realty Group. Agent related.

North Benson Rd Unit 35, Middlebury
$590,000
3 Beds ⋅ 3 Baths ⋅ 24071251 MLS
Welcome to 138 Skyline Dr, Middlebury, CT a beautifully maintained ranch-style home with a finished basement and in-law suite! This home offers the perfect blend of comfort, convenience, and versatility. Step inside the main level to find three spacious bedrooms, that include a primary bedroom with ensuite bathroom, plus a bonus office space, a bright living area, and a well-appointed kitchen. The finished lower level provides a fantastic in-law suite, perfect for extended family or guests with separate washer/dryer hookup and entrance. Outside, the large backyard offers endless possibilities whether you're looking to entertain, garden, or simply relax. A two-car garage with EV charging station inside the garage as well as a long driveway that provides ample parking. Situated in a peaceful neighborhood yet conveniently close to schools, shopping, and major highways, this home is a must-see!

138 Skyline Dr, Middlebury
$587,500
4 Beds ⋅ 3 Baths ⋅ 24034677 MLS
Rare opportunity in Middlebury! Charming Colonial featuring over 2500 square feet of living space, 4 bedrooms, 2.1 baths, a 2 car garage, an eat-in kitchen with granite countertops and stainless steel appliances, dining area, living room with fireplace and built-ins, sunroom, and first floor primary suite with full bath. The second floor offers three spacious bedrooms, and a walk up attic. The outdoor space is incredible sitting on .99 acres with mature landscaping and a private, level backyard with a beautiful stone terrace. Great proximity to the greenway, restaurants, historic town green, parks and playgrounds. A true turn key property! Schedule your showing today.

117 Bronson Dr, Middlebury
$585,000
2 Beds ⋅ 3 Baths ⋅ 24059344 MLS ⋅ Benson Woods BLDG.
This bright and sunny home in the desirable 55+ community of Benson Woods combines country living with modern convenience. Located just minutes from shopping, town, and I-84, offering easy access for both relaxation and commuting. The spacious living room features cathedral ceilings, hardwood floors, and a cozy gas fireplace. The chef's kitchen includes granite countertops, ceiling-height cabinetry, and a double center island with an eating area. The main level features a private primary suite with two walk-in closets, a tray ceiling with a fan, and an en-suite bath. There's also a second bedroom, laundry room, and half bath. Upstairs, a large loft with a ceiling fan and double closet overlooks the living room. A full bath and versatile office/sewing room complete the upper level. The home is equipped with a whole-house stereo system, and the full, unfinished basement is plumbed for a future bath. The deck off the kitchen provides a private, wooded view. Although built in 2005, the interior was customized in 2014. This maintenance-free home gives the perfect blend of comfort and convenience in a peaceful, sought-after community.

111 Periwinkle Dr Unit 111, Middlebury
$585,000
4 Beds ⋅ 3 Baths ⋅ 24044579 MLS
Discover this elegant colonial-style home in Middlebury, set on 1.4 serene acres. With 4 bedrooms plus 2.5 baths, this residence offers a sun room for relaxation and a kitchen with abundant counter space for culinary adventures. The upper level features spacious bedrooms, with vaulted ceilings in the primary suite. En-suite bath is beautifully updated Laundry located on the main floor just off the powder room. Enjoy outdoor entertaining on the spacious deck with an electric awning, ideal for summer gatherings. Oversized walkout basement with wine cellar and wood burning stove. Experience the perfect blend of classic charm and modern convenience in a tranquil setting. many improvements including newer roof and Central Air.

89 Tyler Xing, Middlebury
$585,000
4 Beds ⋅ 3 Baths ⋅ 170607765 MLS
Elegance and stunning curb appeal will pull you into this well maintained colonial home, tucked away in a level, walkable neighborhood. The foyer greets you with gleaming hardwood floors, which is open to the sunken formal living room. The front to back living room offers a cozy gas burning fireplace and large windows to enjoy both back and front yard views. Around the corner, in the heart of the home, you will find the formal dining room, featuring French doors which lead to the screened in porch. Pocket doors give you privacy to the comfortable den with convenient built-ins and sliders to the screened in porch. The eat-in kitchen hosts ample cabinet space, granite countertops, double wall ovens, warming drawer and a breakfast bar making a perfect spot for meal prep and gatherings. The mudroom off of the kitchen offers a space to unload while entering the home from the garage, and close proximity to the washer and dryer. Four generous bedrooms including a full bath, cedar closet, and primary suite give the upper level a quiet spot to rest at the end of a long day. Central air throughout the home and newer windows keeps the home cool in the warmer months. A whole house generator for peace of mind. The beautifully manicured yard, off of the screened in porch, welcomes a game of catch or a backyard BBQ. Well appointed with both classic elegance and modern conveniences, plus a quiet location close to I84 and route 8 make this the perfect spot to call home.

82 Northwood Dr, Middlebury
$585,000
3 Beds ⋅ 2 Baths ⋅ 24122855 MLS
Built in 1911, this four square colonial has so many fabulous vintage qualities including a beautiful, generously sized front entry, arched doorways, custom moldings and so much more. The main level offers a spacious eat in kitchen, formal living and dining rooms as well as a 21 x 13 heated sunroom overlooking rolling hills and distant views. On the second level, 2 bedrooms and a beautifully remodeled full bath. The third level offers a finished bedroom as well as a spacious storage area. On the exterior, a gorgeous front porch, patio, gardens and a barn with 2 garages, an area for chickens. Beautiful gardens as well as a mini orchard: 4 apple trees, 2 Pear, Peach tree, Plum Tree and Cherry tree. (Some photos are from a previous listing so that the exterior shows the landscape.)Agents and prospective buyers: Please do not drive up the driveway unless you are there for a showing.

126 Colonial Ave, Middlebury
$580,000
3 Beds ⋅ 3 Baths ⋅ 24163482 MLS ⋅ Ridgewood At Middlebury BLDG.
Welcome to 36 Highridge Road, a beautifully maintained home in one of Middlebury's most desirable neighborhoods. Built in 2018 and lovingly cared for by its original and only owner, this property offers the perfect blend of modern construction, thoughtful upgrades, and low-maintenance living. Step inside to find a thoughtfully designed interior enhanced with upgraded molding, elegant cabinetry, and high-end appliances that elevate both style and functionality. The inviting living space is truly a showstopper, featuring soaring 30-foot ceilings and a stunning fireplace that creates a warm yet dramatic focal point-perfect for both relaxing and entertaining. Nestled on a highly sought-after cul-de-sac, this home offers both privacy and a true sense of community. Beyond the home itself, residents enjoy access to exceptional, fully loaded amenities including a beautiful clubhouse, resort-style pool, playground, tennis courts, and both indoor and outdoor basketball courts-perfect for an active and social lifestyle. This is a rare opportunity to own a newer construction home with premium upgrades in a prime location-don't miss it! Sale is contingent on seller finding suitable housing.

36 Highridge Road Unit 36, Middlebury
$579,900
3 Beds ⋅ 3 Baths ⋅ 170596284 MLS
The owner has reduced the price to sell! Don't miss your opportunity to call this home yours. Schedule your showing today. Seller is moving to new home in a few weeks, bring your offers!! Welcome home to Luxury!! This custom-built home with every upgrade and exceptional detail is ready to be called home today. Don't miss your opportunity to see this home and enjoy the finest amenities this property has to offer! This home is back on the market and ready to get under contract again. Come see this beautiful home and bring your offers!! Upon entering the driveway you will be greeted by exceptionally landscaped yards and gardens and have a full irrigation system. The landscape lighting allows you to take in beautiful views at any time of day! Enjoy 3 outdoor seating options including a walkway built with blue stone that leads to a private front porch with fans to keep you cool on those summer evenings. Included on this property is a separate driveway with tons of parking and a beautiful barn/workshop! The upper Mahogany back deck comes equipped with 6X6 posts and new aluminum railings. The home offers beautiful and pristine hardwood floors thru out. The kitchen is exceptional offering Cherry custom cabinets, Granite, and a separate Island with a wine chiller! The Wolf appliances including a subzero Industrial refrigerator finish off this room! An absolute MUST SEE!

563 Southford Rd, Middlebury
$577,962
2 Beds ⋅ 2 Baths ⋅ 170534747 MLS ⋅ Benson Woods BLDG.
Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds! Each of our 4 flexible floor plans offer modern amenities coupled with New England Charm. The Simsbury Elite style is our single level detached home with loft option. All homes afford single level living at its finest with second floor loft and 3rd bedroom options. They will feature quaint farm style porches, 2 car attached garages, open floor plans, full basements and some luxurious options! Great location close to town, shopping, restaurants, golf and major highways. Now taking reservations for Phase 1-

317 Hemlock Ln Unit 72, Middlebury
$577,000
4 Beds ⋅ 3 Baths ⋅ 24044033 MLS
Location, location, location! Perfectly nestled on a lovely Middlebury cul-de-sac. Welcome home to this 4 bedroom, 2 1/2 bath, well maintained colonial. A standout feature is a suitable main floor in-law suite which gives flexibility for owners to use as den, a family room. In addition, upon entering, you will find a comfortable, bright, formal living room with bay window, hardwood flooring, wood burning fireplace surrounded by lovely bookcases and built ins. Enjoy easy access for entertaining to a light and bright Formal dining room, with hardwood floors, leading to a large eat in kitchen with up-graded stainless appliances, Corian counters and handy pantry storage. From the kitchen, you will find a large extended deck for family gatherings. On the same floor, you will find a 1/2 bath, first floor bedroom with hardwood floors, and access to 2 more rooms to be used as needed for in-law or family use. sized bedrooms all with The second floor has hardwood floors throughout. The primary bedroom has a new walk-in closet and a remodeled bath with walk in shower. Middlebury Region 15 award winning schools, a lovely greenway in the center of town for long walks, bike riding and additional recreational activities. Excellent location only minutes to major highways for commuting and many fun filled days at Lake Quassapaug, swimming and boating for summer fun.

61 Carriage Dr, Middlebury
$575,000
3 Beds ⋅ 3 Baths ⋅ 24163914 MLS ⋅ Ridgewood At Middlebury BLDG.
Welcome to this beautifully maintained **Portman Elite** model in the highly desirable Ridgewood of Middlebury community. This bright and inviting home offers 3 bedrooms and 2.5 baths, thoughtfully designed for modern living and low maintenance comfort. The main level features an open layout with a spacious living area, dining space, and a well-appointed kitchen ideal for everyday living and entertaining. The first floor bedroom suite provides convenience and privacy, while two additional bedrooms a full bath and loft on the upper level offer excellent flexibility for guests, office space, or hobbies. A private outdoor patio extends the living space-perfect for seasonal dining and relaxation. Additional highlights include ample storage, an attached garage, and access to Ridgewood's exceptional amenities. Ideally located near local shops, restaurants, and commuter routes, this home blends comfort, convenience, and community living. Enjoy all Middlebury has to offer including walking trails, great restaurants and beautiful near by Lake Quassapaug. 90 minutes to NYC.

2 Arrowwood Ct Unit 2, Middlebury
$575,000
3 Beds ⋅ 4 Baths ⋅ 24084834 MLS ⋅ Ridgewood At Middlebury BLDG.
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 a vaulted breakfast area surrounded by windows, granite countertops, and stainless steel appliances. The first-floor primary suite boasts a generous walk-in closet and a full bath. Upstairs, a beautifully finished loft area offers another full bath, a walk-in closet, and two additional bedrooms. The lower level is a showstopper, featuring a built-in wet bar, plenty of space for entertaining, and direct access to a private outdoor patio. A private library/office and an additional full bath complete this level. Enjoy an unbeatable location just a short walk to the clubhouse, which includes an outdoor pool, gym, indoor basketball court, and tennis courts. With easy access to I-84, top-rated schools, and fantastic restaurants-plus just 30 minutes to the train to NYC-this home truly has it all! Don't miss this rare opportunity to own the original model home!

1 Dogwood Ct Unit 1, Middlebury
$575,000
2 Beds ⋅ 3 Baths ⋅ 170620528 MLS ⋅ Benson Woods BLDG.
Welcome to Benson Woods' pristine model home that is now available for purchase. With top tier quality appliances and finishes, this never before lived in free-standing ranch style condominium is move-in ready! Enter into an elegant foyer open to two story great room with corner gas fireplace and hardwood flooring. The gourmet eat in kitchen boasts a Wolf range, Wolf wall oven and a SubZero refrigerator. Other features include custom cherry cabinets, breakfast bar and granite counters. The primary suite features a tray ceiling, hardwood flooring, 2 walk in closets with custom shelving and a private full bath with jetted tub, heated floors and separate shower. The guest bedroom, laundry room and half bath complete the main level. The second floor features large loft overlooking the great room, a full bath and large walk-in cedar closet. The lower level includes large, finished recreation room with built in bar wine closet and loads of storage. Two car attached garage is currently being used as a sales office and will be turned back (bath removed) prior to closing. Benson Woods is an over 55 active adult community located just minutes to shopping and major highways.

103 Periwinkle Dr Unit 103, Middlebury
$574,900
5 Beds ⋅ 2 Baths ⋅ 24141966 MLS
Discover this classic 5-bedroom, 2-bath Colonial set on a private 1.67-acre lot in desirable Middlebury. This home features hardwood floors, a bright formal living room, and a spacious dining room that opens to a cozy three-season porch overlooking the yard. The kitchen offers brand-new stainless steel appliances and the convenient first-floor bedroom includes laundry for easy main-level living. Upstairs, additional bedrooms provide flexible options for a home office, playroom, or guest space. Outside, enjoy a detached barn with abundant workspace, perfect for hobbies, equipment and storage. There is also an oversized 2 car garage. The large, level property offers ample room for gardening, recreation, or future expansion. Located close to schools, parks, and major commuting routes, this home combines comfort, space, and convenience in one great Middlebury location.

292 Park Rd Extension, Middlebury
$571,000
4 Beds ⋅ 2 Baths ⋅ 24022758 MLS
Discover Your Dream Home: Nestled on a 2-acre lot, this well-maintained Cape-style home offers an idyllic retreat with 4 bedrooms, 2 full baths, and a 2-car garage, plus city water and sewers. Indulge in luxury in the remodeled eat-in kitchen featuring updated cabinets, quartz countertops, double ovens, and an electric cooktop, complemented by an island with a prep sink and french doors leading to the front and rear of the home. Flow effortlessly into the formal dining room boasting a tray ceiling, raised paneling, and built-in corner hutches, while the inviting living room exudes warmth with hardwood floors, crown molding, and a fireplace. Adjacent to the living room, a sunroom floods the space with natural light and serene views of the beautiful grounds. Retreat to the well-appointed bedrooms adorned with crown molding, and separated for privacy. Ascend to the finished walk-up attic that offers versatile space with a large bonus room featuring skylights, an electric fireplace, electric heat and a room ideal for crafting or a home office. Outside, a covered back patio with skylights and a fan overlooks the expansive acreage, inviting relaxation and enjoyment. Don't miss out on this exceptional opportunity and the possibilities that this home offers - come take a look!

183 Three Mile Hill Rd, Middlebury
$570,000
5 Beds ⋅ 4 Baths ⋅ 24066679 MLS
Grand, 5-bedroom, 4 bathroom, 3100sf+, fully updated, well maintained Middlebury Cape. This prodigious has been updated with a new heating system, central air, split systems, a new roof, well components and filtration and wood flooring throughout. The spacious, recently renovated kitchen adorns custom cabinetry, breath taking granite countertops and new stainless steel appliance package. Stately, well preserved wide plank wood flooring and a masonry fireplace enhance the sun-drenched living room and dining area. The oversized family room has a bay window and features sliders to a private Trex deck overlooking lush, emerald green, professionally landscaped grounds, bursting with floral delights and private gardens. The upper level offers three generous guest bedrooms with engineered wood flooring, and a grand primary bedroom suite with private balcony access which provides owners a peaceful oasis to rejoice. The mechanicals, roof, appliances, whole house generator and all major components of this home have been replaced during the current homeowner's stewardship. A detached, lower-level pole barn with 100-amp electrical service electric can be used as a fun indoor facility, or extra income with rental to third parties for equipment storage. Located conveniently close to highly rated Middlebury schools and close radius to Edgewood Bath and Tennis Club further round out the homes intrinsic appeal.

428 Benson Rd, Middlebury
$570,000
4 Beds ⋅ 3 Baths ⋅ 24033713 MLS
Welcome to 185 Curtis Farms Road in Middlebury! This beautiful home sits on 2.3 acres and features 4 bedrooms, 2.5 baths, and a finished basement. Enjoy the spaciousness of an oversized two-car garage and a 480 sq ft outdoor patio, perfect for entertaining. With a newer roof and modern amenities, this home offers convenience and comfort. Located in the award-winning Region 15 School District, it provides excellent educational opportunities. Experience the best of both worlds with a blend of modern living and a prime location.

185 Curtis Farms Rd, Middlebury
$569,900
3 Beds ⋅ 3 Baths ⋅ 24179784 MLS ⋅ Ridgewood At Middlebury BLDG.
Immaculate 3 bedroom 2.5 bathroom Portman unit in the Sought-After Ridgewood Community! Built by luxury Toll Brothers, with apprx. 2400 SqFt & a remodeled FINISHED BASEMENT. The main level features an open floor plan with gleaming hardwood floors, tons of natural light & hunter Douglas shades. The eat in kitchen offers stainless steel appliances, granite countertops, a gas cooktop that brings a warm area that's perfect for entertaining or just relaxing. Outside the kitchen, a private deck with a yard to entertain with upgraded steps. The spacious living room highlights a gas fireplace with a shiplap wall and a wood mantle. You also have a formal dining/ sitting area. Upstairs, the primary suite impresses most with vaulted ceilings, a large walk-in closet and a large bathroom w/ a tile shower & double vanity sink. 2nd bedroom includes vaulted ceilings and personal touches that make the room stand out. 3rd bedroom has a beautiful custom accent wall. Laundry room all on 2nd floor! The remodeled finished basement has beautiful New floors, custom built in shelving.. great room for a media/ entertainment play area or office. The garage is immaculate with custom shelving and built ins throughout for functionality and more storage. Resort-style amenities include an outdoor pool, gym, tennis and basketball courts, movie theater, clubhouse with pool table and lounge area. 1.25 hours from NYC. You can't build new construction at this price, take advantage. Book your home tour today

72 Ridgewood Dr Unit 72, Middlebury
$569,900
2 Beds ⋅ 2 Baths ⋅ 170527693 MLS ⋅ Benson Woods BLDG.
Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds! Each of our 4 flexible floor plans offer modern amenities coupled with New England Charm. The Simsbury Elite style is our single level detached home with loft option. All homes afford single level living at its finest with second floor loft and 3rd bedroom options. They will feature quaint farm style porches, 2 car attached garages, open floor plans, full basements and some luxurious options! Great location close to town, shopping, restaurants, golf and major highways. Now taking reservations for Phase 1-

207 Sugar Maple Way Unit 34, Middlebury
$569,500
3 Beds ⋅ 3 Baths ⋅ 24155854 MLS ⋅ Ridgewood At Middlebury BLDG.
Special end unit townhome filled with natural sunlight and serene pond views. Built in 2019 and meticulously maintained, this home offers the feel of new construction throughout. The main level features rich hardwood floors, expanded kitchen cabinetry, and access from the kitchen to a private, expanded deck, perfect for outdoor dining or relaxing. The living room includes a gas-burning fireplace and oversized windows that bring in abundant natural light. The finished lower level provides a comfortable family room and includes a rough-plumbed half bath for future expansion. Sliding doors lead to a level yard and small garden area. Upstairs, the primary suite offers a full bath and walk-in closet. Two additional bedrooms, a full hall bath, and a convenient laundry room complete the upper level. Two car garage, natural gas hook-up and direct water heater for ease. Located in the desirable Ridgewood community, residents enjoy access to an updated clubhouse, heated pool, indoor basketball court, fitness center, playground, and tennis courts. A beautiful, nature walking path is located directly behind this home. Conveniently situated in the heart of Middlebury with easy access to the Middlebury Greenway, Memorial Park, and I-84. Close proximity to Quassy Lake and area amenities. Exceptional value in both home and community.

1 Arrowwood Ct Unit 1, Middlebury

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