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223 Carriage Dr, Middlebury
$670,000
4 Beds ⋅ 4 Baths ⋅ 24160037 MLS
A timeless center hall colonial set in one of Middlebury's most cherished neighborhoods. This beautifully maintained home features a custom kitchen with Subzero refrigeration, Wolf gas cooktop and double ovens, marble countertops, and built-in wine storage. Hardwood floors run throughout the main living areas, where a warm and inviting family room with a gas log fireplace sits just off the kitchen. The formal living room, anchored by a handsome fireplace, opens to a bright library with built-in bookcases. The home offers four bedrooms, including a spacious primary suite with a dressing room and a remodeled bath. A finished lower level room with built-ins and a private walkout entrance provides flexible space for work, hobbies, or guests. A whole house generator, newer windows and roof are just a few of the updates. The backyard is a true retreat, featuring mature landscaping, an expansive bluestone patio, and a deck with a pergola-ideal for outdoor dining and relaxation. Enjoy Middlebury's charming amenities, including local restaurants, the Greenway walking path, a nearby winery, and the town green. Conveniently located within 90 miles of NYC and approximately 2.5 hours to Boston

223 Carriage Dr, Middlebury
117 Periwinkle Dr Unit 117, Middlebury
$669,900
3 Beds ⋅ 4 Baths ⋅ 24125307 MLS ⋅ Benson Woods BLDG.
No detail has been overlooked in the stunning remodel of this elegant home in Benson Woods, Middlebury's premier active adult community. Perched on a premium lot with serene views of the Eight Mile River, this residence offers 3-4 bedrooms, 2 full baths, and 2 half baths across a thoughtfully designed layout. Step inside to discover custom interior trim, rich wood flooring, and a chef's kitchen that will delight culinary enthusiasts - featuring a natural gas Wolf stove, Sub-Zero refrigerator, custom cabinetry, quartz countertops, and a walk-in pantry. The sunlit breakfast area opens seamlessly to a newly renovated Trex deck, perfect for morning coffee or evening gatherings. The main-floor primary suite is a true retreat, boasting dual walk-in closets with custom organizers and an updated bath with premium fixtures. A second bedroom and laundry room complete the main level. Upstairs, guests will enjoy a spacious third bedroom, full bath, and a loft overlooking the dramatic great room below. The finished walk-out lower level adds even more versatility, with a generous great room, dedicated wine room, and exercise space. French doors lead to a charming bluestone patio, ideal for relaxing or entertaining. Benson Woods offers privacy and tranquility, yet remains close to shopping, dining, swim and tennis clubs, and scenic walking trails. This is more than a home - it's a lifestyle of comfort, elegance, and connection.

117 Periwinkle Dr Unit 117, Middlebury
130 Fairhaven Dr, Middlebury
$668,000
3 Beds ⋅ 3 Baths ⋅ 24184080 MLS
Ideal location! Beautiful 3-bedroom, 3.5-bath colonial situated at the end of a private cul-de-sac in desirable Middlebury, just minutes from the highway. This bright, sun-filled home features hardwood floors throughout, a spacious family room, custom kitchen with quartz countertops, stainless steel gas range, plus a formal dining room with a brick fireplace. Relax in the skylit sunroom or enjoy the finished lower level with walkout, ideal for an in-law setup, recreation room, or home office. Above the two car garage there is a separate room that could be used as a possible fourth bedroom. Step outside to a spacious, two tiered deck overlooking an exceptionally private backyard with an above ground pool. This house is set on nearly 3 acres, backing directly to the Middlebury Land Trust with an additional shed. This home offers the perfect combination of comfort, privacy, and convenience. Schedule your private showing today!

130 Fairhaven Dr, Middlebury
200 Northridge Dr, Middlebury
$650,000
3 Beds ⋅ 3 Baths ⋅ 24190947 MLS
Welcome to this beautifully updated contemorary ranch offering an open floor plan, vaulted ceilings, and an inviting sense of space. Nestled among million dollar homes, this property combines comfort, style, and an exceptional location. The spacious living area features a cozy wood burning fireplace and flows seamlessly into the renovated kitchen with abundant cabinetry, a breakfast bar, a coffee station, and a convenient nook, ideal for a home office or a place to sit and relax, overlooking the patio through sliding glass doors. The renovated full bath adds modern appeal, while the private primary suite offers its own full bath, with modern cabinetry, and thoughtfully tucked away closets. Freshly painted inside and out, the home has a clean, warm feel throughout. Outside, enjoy professionally landscaped grounds highlighted by a beautiful rose garden and a brand new Kloter Farm shed. The lower level welcomes you with a foyer leading to a versatile den or flex space, while the expansive basement offers endless possibilities for future living space, a workshop, or abundant storage. Additional features include central air conditioning, new well tank and updated softener, new gutters and downspouts with leaf guards, new hot water heater, new fiberglass doors and an attached two car garage. Move in just in time for the new school year and enjoy all that the award-winning Region 15 School District has to offer!

200 Northridge Dr, Middlebury
168 N Farm Rd, Middlebury
$650,000
4 Beds ⋅ 4 Baths ⋅ 24178550 MLS
Nestled in the highly sought-after North Farm neighborhood, this exceptional 4BR, 3.5 bath Colonial is beautifully situated on 2.34 private acres offering the perfect blend of classic charm and comfortable living. A generous entry foyer welcomes you into a thoughtfully designed home featuring a formal living room with fireplace, elegant formal dining room and a spacious eat-in kitchen complete with pantry and breakfast bar. The inviting family room is the heart of the home, showcasing vaulted ceilings, exposed wood beams, wide plank hardwood floors and a dramatic floor-to ceiling fireplace. A dedicated study/office with built-in bookcases and a versatile bonus room provide flexible space for today's lifestyle needs. Outdoor living is equally impressive with double decks overlooking an expansive pool and serene backyard, ideal for entertaining and relaxing all summer long. This is a rare opportunity to own a beautiful property in one of the area's most desirable neighborhoods.

168 N Farm Rd, Middlebury
51 Cross Rd, Middlebury
$645,000
4 Beds ⋅ 4 Baths ⋅ 24141874 MLS
Highest and Best by Wednesday, 12/10, 6pm. Welcome to this beautifully maintained Colonial nestled in the highly sought-after Curtis Farms neighborhood. Thoughtfully designed, this home blends classic charm with modern comfort. The gorgeous kitchen offers abundant cabinetry, granite countertops, and a gas cooktop overlooking the breakfast bar, which enjoys a view of the stone-faced fireplace. A small butler's bar provides seamless access to the elegant formal dining room. Arched entryways throughout the main level enhance the home's architectural character. The newly tiled, sunroom offers picturesque views of the backyard, an ideal space for gathering or quiet relaxation. The formal living room features a stately built-in with a dedicated nook perfectly suited for work, study, or reading. Recently refinished hardwood floors, fresh paint, and tasteful new fixtures extend throughout the home, creating a sophisticated and cohesive aesthetic. The upper level includes 3 bedrooms, including a serene primary suite with a walk-in closet and a gorgeous en-suite bath. The newly renovated, finished basement offers versatility with a stylish kitchenette, wide-plank vinyl flooring, a renovated full bath, and a bedroom with a walk-in closet, making it ideal as an in-law space, guest suite, private office, or recreational retreat. Fully fenced backyard with covered outdoor kitchen, heated pool with new liner and cover, and shed. Brand new roof and new whole-house water system.

51 Cross Rd, Middlebury
1 Independence Cir Unit 1, Middlebury
$630,000
4 Beds ⋅ 3 Baths ⋅ 24177570 MLS ⋅ Brookside Of Middlebury BLDG.
Nestled within the highly sought-after Brookside of Middlebury, this exceptional 4-bedroom, 2.5-bath Colonial offers timeless elegance, sophisticated design, and luxurious living throughout. Meticulously maintained, this impressive residence features a spacious, light-filled floor plan ideal for both refined entertaining and everyday comfort. The stunning eat-in kitchen serves as the heart of the home, showcasing a center island, granite countertops, tile backsplash, all new stainless steel appliances. Beautiful formal dining room, inviting living room, private office/den, and an expansive family room with fireplace create the perfect blend of warmth and sophistication. A slider leads to a beautiful Trex deck, offering seamless indoor-outdoor living and the perfect setting for relaxing or entertaining. Upstairs, the spacious primary suite provides a private retreat complete a whirlpool tub, separate shower, and generous closet space. Three additional spacious bedrooms, a beautifully appointed full bath, and convenient second-floor laundry complete the upper level. The exceptional finished lower level offers premium additional living space featuring a custom movie room, spacious recreation/family room, and abundant storage. Close to shopping, dining, parks, and commuter routes.

1 Independence Cir Unit 1, Middlebury
10 Pelham Way Unit 10, Middlebury
$625,000
3 Beds ⋅ 3 Baths ⋅ 24171754 MLS ⋅ Steeplechase Of Middlebury BLDG.
Gorgeous freestanding Steeplechase unit, beautifully renovated over the past several years. A new kitchen and baths, refinished hardwood floors, and updated light fixtures are just a few of the many improvements. The outdoor space is exceptional, featuring a charming open front porch and a covered bluestone patio in the back. The main level offers a living room with a cathedral ceiling, a family room off the kitchen with a fireplace and sliders to the back patio, a bright and cheerful eat-in kitchen, and a formal dining room. Upstairs, the home includes three bedrooms, two full baths, and refinished hardwood floors throughout.

10 Pelham Way Unit 10, Middlebury
16 Winding Trail, Unit 16, Middlebury
$625,000
3 Beds ⋅ 3 Baths ⋅ 24157092 MLS ⋅ Ridgewood At Middlebury BLDG.
Set at the end of a quiet cul-de-sac in ONE OF RIDGEWOODS COVETED LOCATIONS, this home overlooks an expansive manicured lawn bordered by evergreens and woodland for exceptional privacy and year round natural beauty. Sunlight fills every room, enhancing the warm, cohesive feel of HARDWOOD FLOORS THROUGHOUT BOTH LEVELS - a rare feature in this community. The bright, sparkling kitchen features white cabinetry, undermount lighting, stainless appliances, & spacious center island/breakfast bar perfect for "cooking with company". Genuine MARBLE IN THE KITCHEN AND BATHS adds the patina of refined, timeless elegance. A charming breakfast nook overlooks the sundeck, inviting you to dine al fresco basking in sunshine & nature. An open dining area flows easily into the large living room with gas fireplace which provides warmth & ambiance as do the $5,600 Modern Smart Shades. A flexible office/playroom/den completes the main floor. Upstairs, a loft offers flex space leading to the primary suite with walk-in closet, double vanity, tile shower & jacuzzi tub. Two additional bedrooms, a full bath, and laundry complete this level. The walkout lower level has great sunlight with glass doors opening to the patio and is plumbed for potential in-law, workshop or family room. Ridgewood amenities include an 8,300 sq ft clubhouse, fitness center, yoga space, movie theatre, indoor basketball, tennis, & heated pool - A resort oasis! Don't miss this rare opportunity to own this truly special home.

16 Winding Trail, Unit 16, Middlebury
90 Fenn Rd, Middlebury
$620,000
4 Beds ⋅ 4 Baths ⋅ 24167501 MLS
The home you have been waiting for is waiting for you at 90 Fenn Road, Middlebury. Need room for inlaws? teens? an office? You can have it right here, tucked on 1.67 acres in a desirable Middlebury location. As you enter the spacious tiled foyer and look around, a formal sunken living room greets you on one side and a formal dining room on the other. You will notice the oak flooring in both rooms. You can then make your wy to the oversized kitchen with separate dining area, featuring updated quartz counters and newer appliances. The kitchen is open to the family room and on cool nights you can enjoy the fireplace from both rooms. Upstairs the four bedrooms and two full baths create comfortable living quarters. In addition, an unfinished 21'x22 over the office is a fabulous opportunity for the new owner to add more space to this already spacious home. There is more than enough storage area provided by the walk up attic and the full basement that offers an overhead garage door for easy access. The current owner had converted the former 600 sq. ft garage as a dentist office after acquiring a certificate of zoning compliance.

90 Fenn Rd, Middlebury
193 Ridgewood Dr Unit 193, Middlebury
$620,000
3 Beds ⋅ 3 Baths ⋅ 24163290 MLS ⋅ Ridgewood At Middlebury BLDG.
This beautifully upgraded condominium at Ridgewood at Middlebury offers the perfect blend of style, comfort, and low-maintenance living. Built in 2022 and showing like new, the home features sun-filled spaces, engineered wood floors throughout, and a thoughtfully designed open layout. The main level welcomes you with a seamless flow ideal for everyday living and entertaining. At the center of the home is the extensively upgraded kitchen, featuring white cabinetry, stainless steel appliances, and a striking 8-foot center island with a waterfall countertop. The current owners enhanced both form and function with a custom pantry, built-in bar area with wine chiller, double ovens, rollout shelving in all lower cabinets and pantry, and under- and over-cabinet lighting. The kitchen opens to a sunny breakfast nook with direct access to the sundeck, creating easy indoor-outdoor living. Just beyond, the open dining area connects to a spacious living room with a gas fireplace. A flexible main-level office, den, or playroom adds valuable versatility. Upstairs, a central loft leads to the primary suite, complete with a walk-in closet featuring custom closet systems, a double vanity, and a tile shower. Two additional bedrooms, a full bath, and convenient second-floor laundry complete the upper level. The lower level offers generous space for future finishing-ideal for a gym, workshop, or additional living area-along with ample storage.

193 Ridgewood Dr Unit 193, Middlebury
3 Hunting Ridge Rd, Middlebury
$620,000
3 Beds ⋅ 3 Baths ⋅ 24155317 MLS
Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 3 Hunting Ridge Road (aka Lot 1) is now complete and ready for occupancy! It is one level living at its finest! Features includes hardwood floors throughout, gas fireplace with stone surround, gourmet kitchen with large center island, convenient office in addition to 3 bedrooms. The primary bedroom boasts walk-in closet with custom shelving and private full bath. Come by and see the incredible views from this newly completed home!! There are several other lots and plans to choose from or will build to suit! City water and sewer !!

3 Hunting Ridge Rd, Middlebury
408 Breakneck Hill Rd, Middlebury
$615,000
2 Beds ⋅ 3 Baths ⋅ 24164434 MLS
Charm abounds in this remodeled classic cape with 2 car garage, central air, and massive 1st floor master suite! Remodeled eat-in-kitchen with granite countertops, stainless steel appliances, tile backsplash and breakfast bar. Living room with fireplace and hardwood floors. Dining room with hardwood floors. Luxurious master suite with built-ins, walk-in california closet, and large remodeled master bath with quartz countertops, double sinks, soaking tub, heated floor and tile surround shower. main level laundry room. Character driven powder room. Upstairs 2nd bedroom with hardwood floors. Full bath with subway tile surround shower and tile floor. Additional room with hardwood floors. Newer composite deck overlooks a country backyard. This home has charm and modern amenities. It will not last! Town Card has 2 Bedrooms and 1.1 baths. Home has 2.1 baths and additional rooms.

408 Breakneck Hill Rd, Middlebury
178 Ridgewood Dr Unit 178, Middlebury
$607,000
3 Beds ⋅ 3 Baths ⋅ 24177424 MLS ⋅ Ridgewood At Middlebury BLDG.
Pristine is the word for this beautiful, move-in-ready townhome built in 2022, offering modern finishes, extensive tasteful upgrades, and exceptional living space throughout. Living at Ridgewood combines low-maintenance luxury with outstanding community amenities. The main level features an open-concept layout with stylish finishes and updates, including wainscoting throughout the first floor; new dining room, foyer, and kitchen lighting; ceiling fans in the living room, basement, and upstairs bedrooms; and a new kitchen refrigerator. All closets have been customized by Closets By Design for optimal organization and functionality. The primary and second full bathrooms feature quartz double-sink vanity tops, and the primary bathroom includes a custom shower door. A standout feature is the newly completed basement renovation, finished just six months ago, which adds more than 600 square feet of living space. Designed with basement-specific materials, the renovation includes metal studs, moisture-resistant materials, luxury engineered flooring with vapor protection, double-panel doors that match the main level, and a beautifully finished kitchenette with quartz countertops, a full-size refrigerator, and a stainless steel sink. The basement also features a fresh-air system that automatically recirculates the air and is fully heated. Additional upgrades include a professionally finished garage floor using durable polyurea coatings, a superior alternative to epoxy.

178 Ridgewood Dr Unit 178, Middlebury
North Benson Rd Unit 48, Middlebury
$603,780
3 Beds ⋅ 3 Baths ⋅ 24129196 MLS ⋅ Aberdeen Estates At Benson Woods BLDG.
Last remaining unit! 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. Model unit coming July 2025. A Planned Unit Development (PUD). Developed by Newport Realty Group. Agent related.

North Benson Rd Unit 48, Middlebury
321 Artillery Rd, Middlebury
$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
72 Carriage Dr, 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
39 Independence Cir Unit 39, 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
428 Breakneck Hill Rd, 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
85 Blueberry Knls, Middlebury
$585,000
3 Beds ⋅ 2 Baths ⋅ 24199241 MLS
Welcome to a truly special property! This beautifully updated 7-room ranch is tucked away at the end of a private cul-de-sac and set on stunning, parklike grounds that offer exceptional privacy and tranquility. Meticulously maintained and thoughtfully updated, this home features newer mechanicals throughout for added comfort and peace of mind-see the attached upgrade list for details. The inviting layout offers plenty of space for everyday living and entertaining, while the partly finished basement provides even more room for recreation, hobbies, a home office, or whatever your lifestyle demands. From the peaceful setting to the extensive updates and impeccable condition, this is a property that truly stands out. Private, picturesque, beautifully maintained, and located in a wonderful area-this exceptional ranch is a must-see!

85 Blueberry Knls, Middlebury
126 Colonial Ave, 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
36 Highridge Road Unit 36, 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
North Benson Rd Unit 52, Middlebury
$579,303
3 Beds ⋅ 3 Baths ⋅ 24100213 MLS ⋅ Aberdeen Estates At Benson Woods BLDG.
5 Units Remaining! 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. Model unit coming July 2025. Phase 2 occupancy starting early 2026. A Planned Unit Development (PUD). Developed by Newport Realty Group. Agent related.

North Benson Rd Unit 52, Middlebury
2 Arrowwood Ct Unit 2, 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
1 Dogwood Ct Unit 1, 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
292 Park Rd Extension, 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
65 N Benson Rd Unit 65, Middlebury
$573,572
3 Beds ⋅ 3 Baths ⋅ 24177098 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 55 is an End Unit. Phase 1 occupancy starting Summer 2025. Model unit coming soon! A Planned Unit Development (PUD) - Built by Lovley Development, Inc. / Developed by Newport Realty Group. Agent related.

65 N Benson Rd Unit 65, Middlebury
72 Ridgewood Dr Unit 72, 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
1 Arrowwood Ct Unit 1, 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
23 Caveson Court, Unit 23, Middlebury
$565,000
3 Beds ⋅ 3 Baths ⋅ 24135107 MLS ⋅ Steeplechase Of Middlebury BLDG.
Come discover this beautifully maintained 3-bedroom, 2.5-bathroom detached condo, ideally situated on a quiet cul-de-sac in the highly sought-after Steeplechase complex in Middlebury! This rare standalone unit offers the privacy of a single-family home with the convenience of condo living-no shared walls and minimal exterior maintenance. Inside, you'll find a spacious and open floor plan with abundant natural light, a modern kitchen, and a comfortable living area perfect for entertaining. Living room features beautiful fireplace with a gorgeous mantle. The primary bedroom features an en-suite bathroom and walk-in closet with additional space perfect for home office. Enjoy outdoor living with a private patio or backyard area, ideal for relaxing evenings or weekend gatherings. Located close to parks, schools, shopping, and major commuting routes, this home combines comfort, privacy, and convenience. Additional 500+ sq feet of living space in basement with wet bar and beautiful gas fireplace. New HVAC system was just installed last month! Not Age Restricted! This gorgeous home is a must see!

23 Caveson Court, Unit 23, Middlebury

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