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Welcome to this inviting Middlebury home, beautifully situated on 1.6 private acres directly along the Greenway and across from picturesque Fenn's Pond. Offering a wonderful combination of privacy, natural beauty, and convenient living, this property is ideal for those who enjoy walking, outdoor activities, and entertaining. A long private driveway leads to the home, providing plenty of parking for family and guests. The fenced backyard features a dedicated play area, creating a wonderful outdoor space for children, pets, or simply enjoying the peaceful surroundings. Inside, the home is filled with natural light, and well-proportioned living spaces. The upper level features a spacious primary bedroom with a private full bath, along with two additional generously sized bedrooms, all with hardwood flooring. A second full bath includes both a tub and separate shower stall. The formal dining room is perfect for hosting and features hardwood flooring and a fireplace, while the oversized Great Room makes an impressive everyday gathering space with its cathedral ceiling and abundance of windows overlooking the private, natural setting. The home's open and light-filled perfect for entertaining. The eat-in kitchen features warm wood cabinetry, granite countertops, tile backsplash, and stainless-steel appliances. Lower level provides additional space, laundry room, garage, and unfinished space for storage. Recent updates include Newer Roof, Septic, Windows, and hot water heater.

3 Beds ⋅ 2 Baths ⋅ 24211870 MLS

Welcome to this inviting Middlebury home, beautifully situated on 1.6 private acres directly along the Greenway and across from picturesque Fenn's Pond. Offering a wonderful combination of privacy, natural beauty, and convenient living, this property is ideal for those who enjoy walking, outdoor activities, and entertaining. A long private driveway leads to the home, providing plenty of parking for family and guests. The fenced backyard features a dedicated play area, creating a wonderful outdoor space for children, pets, or simply enjoying the peaceful surroundings. Inside, the home is filled with natural light, and well-proportioned living spaces. The upper level features a spacious primary bedroom with a private full bath, along with two additional generously sized bedrooms, all with hardwood flooring. A second full bath includes both a tub and separate shower stall. The formal dining room is perfect for hosting and features hardwood flooring and a fireplace, while the oversized Great Room makes an impressive everyday gathering space with its cathedral ceiling and abundance of windows overlooking the private, natural setting. The home's open and light-filled perfect for entertaining. The eat-in kitchen features warm wood cabinetry, granite countertops, tile backsplash, and stainless-steel appliances. Lower level provides additional space, laundry room, garage, and unfinished space for storage. Recent updates include Newer Roof, Septic, Windows, and hot water heater.

961 Middlebury Rd, Middlebury

$485,000

Step inside and the first thing you notice is the light: sun pouring through the kitchen's bay window onto warm new bamboo floors, which give way to the original hardwood, refinished, in the living and dining rooms. This 1941 Cape has been renovated top to bottom with high-end materials and a designer's eye, while keeping the original character that makes an older home feel like home. The kitchen and both bathrooms share a thread of rich black stone, and the primary bath is a retreat vanity, warm wood and soft, glowing floor lighting. Custom details show up wherever you look, custom kitchen cabinetry, lots of built-in storage, extra space tucked into the attic. Downstairs, the finished lower level gives you room to spread out - a second living room, a compact gym, and office fit comfortably. The mechanical room adds more storage alongside a dedicated laundry area. The big-ticket items are handled. A brand-new multi-zone AC+Heat system keeps every room comfortable, and a second independent heating systems (oil) means you are never left in the cold. The roof is just ten years old, and the garage has been refinished and waterproofed. Appliances and systems are covered by a one-year warranty, extendable up to three years. Final renovation details are still being finalized. Turnkey finished property at closing.

3 Beds ⋅ 2 Baths ⋅ 24209861 MLS

Step inside and the first thing you notice is the light: sun pouring through the kitchen's bay window onto warm new bamboo floors, which give way to the original hardwood, refinished, in the living and dining rooms. This 1941 Cape has been renovated top to bottom with high-end materials and a designer's eye, while keeping the original character that makes an older home feel like home. The kitchen and both bathrooms share a thread of rich black stone, and the primary bath is a retreat vanity, warm wood and soft, glowing floor lighting. Custom details show up wherever you look, custom kitchen cabinetry, lots of built-in storage, extra space tucked into the attic. Downstairs, the finished lower level gives you room to spread out - a second living room, a compact gym, and office fit comfortably. The mechanical room adds more storage alongside a dedicated laundry area. The big-ticket items are handled. A brand-new multi-zone AC+Heat system keeps every room comfortable, and a second independent heating systems (oil) means you are never left in the cold. The roof is just ten years old, and the garage has been refinished and waterproofed. Appliances and systems are covered by a one-year warranty, extendable up to three years. Final renovation details are still being finalized. Turnkey finished property at closing.

314 Porter Ave, Middlebury

$550,000

For the antique lover, the one with vision and a desire to bring this fabulous home back to its original glory, this is the place for you. Set on over 2 acres within walking distance to Lake Quassapaug, this is a fabulous property. It offers a main house with approximately 1900 s.f.. You'll love the wide board floors, plaster walls and so many details that reflect a fabulous past. In addition to the main house, there is a detached, oversized 2 car garage with a workshop and a finished artist's loft. Enjoy the opportunity for gardens, more fruit trees and a lovely enclosed screened porch. So many original features. This is a spot for the artist, antique lover, the ones who appreciate history and have a desire to own a piece of history. The house is not air conditioned, but the area over the garage has a split system for heat and air conditioning.

4 Beds ⋅ 3 Baths ⋅ 24209000 MLS

For the antique lover, the one with vision and a desire to bring this fabulous home back to its original glory, this is the place for you. Set on over 2 acres within walking distance to Lake Quassapaug, this is a fabulous property. It offers a main house with approximately 1900 s.f.. You'll love the wide board floors, plaster walls and so many details that reflect a fabulous past. In addition to the main house, there is a detached, oversized 2 car garage with a workshop and a finished artist's loft. Enjoy the opportunity for gardens, more fruit trees and a lovely enclosed screened porch. So many original features. This is a spot for the artist, antique lover, the ones who appreciate history and have a desire to own a piece of history. The house is not air conditioned, but the area over the garage has a split system for heat and air conditioning.

802 Charcoal Ave, Middlebury

$650,000

Luxury Toll Brothers built townhome in sought after Ridgewood at Middlebury! This exquisite Denton Elite end unit was customized in 2018 and offers 3 bedrooms, 2.5 baths and over 2,643 sqft of beautifully designed living space. The main level welcomes you with a spacious foyer, double storage closet, private study with garden doors and powder room. The custom kitchen features upgraded cabinetry, granite counters, stainless steel appliances, gas cooktop, hood, subway tile backsplash, oversized island and breakfast nook/ eat in kitchen. This opens to a composite deck, perfect for morning coffee or entertaining with a peaceful backyard. The living room features hardwood floors, gas fireplace and mantle, while the dining area showcases an octagonal tray ceiling and chandelier. Soaring 9 ft ceilings & upgraded lighting complete the main level. Upstairs you'll find 3 oversized bedrooms, full hall bath, laundry and a versatile loft ideal for a den, office or potential 4th bedroom. The primary suite features cathedral ceilings, massive walk in closet & luxurious bath with glass enclosed tiled shower, built in seat, double vanity & granite counters. Large basement offers potential for nearly 1,000 additional sqft. Two car garage. Upgraded location for private back and side yard, great for entertaining. Enjoy resort style amenities including heated pool, clubhouse, fitness center, tennis and indoor basketball. Enjoy the middlebury greenway! Approximately 1.3 hours to NYC! TURN KEY!

3 Beds ⋅ 3 Baths ⋅ 24209236 MLS ⋅ Ridgewood At Middlebury BLDG.

Luxury Toll Brothers built townhome in sought after Ridgewood at Middlebury! This exquisite Denton Elite end unit was customized in 2018 and offers 3 bedrooms, 2.5 baths and over 2,643 sqft of beautifully designed living space. The main level welcomes you with a spacious foyer, double storage closet, private study with garden doors and powder room. The custom kitchen features upgraded cabinetry, granite counters, stainless steel appliances, gas cooktop, hood, subway tile backsplash, oversized island and breakfast nook/ eat in kitchen. This opens to a composite deck, perfect for morning coffee or entertaining with a peaceful backyard. The living room features hardwood floors, gas fireplace and mantle, while the dining area showcases an octagonal tray ceiling and chandelier. Soaring 9 ft ceilings & upgraded lighting complete the main level. Upstairs you'll find 3 oversized bedrooms, full hall bath, laundry and a versatile loft ideal for a den, office or potential 4th bedroom. The primary suite features cathedral ceilings, massive walk in closet & luxurious bath with glass enclosed tiled shower, built in seat, double vanity & granite counters. Large basement offers potential for nearly 1,000 additional sqft. Two car garage. Upgraded location for private back and side yard, great for entertaining. Enjoy resort style amenities including heated pool, clubhouse, fitness center, tennis and indoor basketball. Enjoy the middlebury greenway! Approximately 1.3 hours to NYC! TURN KEY!

85 Ridgewood Dr Unit 85, Middlebury

$699,900

Middlebury Multi-Family-RARE FIND! 4 units! Two buildings on one (.41 acre) parcel. Situated on "park like" grounds at end of cul-de-sac with IN GROUND SWIMMING POOL, and two car detached garage. Commuter friendly with easy access to Rt 8 & I-84, and only moments away to Post University and NVCC. 1st building consists of a side by side TRI-PLEX w/garage under and fireplaced L/R's. 2nd building consists of an adorable, detached single-family RANCH STYLE house-3 rooms/1 bedroom w/oversize fireplace living room & oil heat. Separate heat and utilities. Public water & sewer. Enjoy Middlebury's Greenway trails, hop brook lake for swimming, picnicking, hiking, biking and so much more-all within walking distance! The SUBURBAN town of MIDDLEBURY, is HIGHLY SOUGHT AFTER, rated on TOP, for it's schools and LOW, RENTAL VACANCY. Perfect opportunity for OWNER OCCUPANT to live in one unit and collect rent from other 3 units. INVESTORS...be proud to add this one to your portfolio while growing "SWEET EQUITY" . PLEASE REFER TO AGENT COMMENTS!

5 Beds ⋅ 4 Baths ⋅ 24207437 MLS

Middlebury Multi-Family-RARE FIND! 4 units! Two buildings on one (.41 acre) parcel. Situated on "park like" grounds at end of cul-de-sac with IN GROUND SWIMMING POOL, and two car detached garage. Commuter friendly with easy access to Rt 8 & I-84, and only moments away to Post University and NVCC. 1st building consists of a side by side TRI-PLEX w/garage under and fireplaced L/R's. 2nd building consists of an adorable, detached single-family RANCH STYLE house-3 rooms/1 bedroom w/oversize fireplace living room & oil heat. Separate heat and utilities. Public water & sewer. Enjoy Middlebury's Greenway trails, hop brook lake for swimming, picnicking, hiking, biking and so much more-all within walking distance! The SUBURBAN town of MIDDLEBURY, is HIGHLY SOUGHT AFTER, rated on TOP, for it's schools and LOW, RENTAL VACANCY. Perfect opportunity for OWNER OCCUPANT to live in one unit and collect rent from other 3 units. INVESTORS...be proud to add this one to your portfolio while growing "SWEET EQUITY" . PLEASE REFER TO AGENT COMMENTS!

10 Old Waterbury Rd, Middlebury

$749,000

Looking for a quiet, secluded location? No street noise, no close neighbors? Welcome to 182 Green Hill Road, where space, privacy, and an exceptional Curtis Farms setting come together. Set at the end of a long private driveway on nearly 3 acres, this spacious 4-bedroom, 2.5-bath Colonial offers over 3,000 square feet of living space with an incredible grand living-room with fireplace and vaulted ceiling, perfect for entertaining or relaxing with the family. The main level features hardwood flooring, generous formal living and dining areas, a private office, and a spacious eat-in kitchen with granite countertops and stainless appliances. The primary suite includes a private en-suite bath with Whirlpool tub, separate shower and double vanity. Three additional bedrooms provide plenty of room for family and guests. Enjoy the privacy of the expansive grounds from the large deck, along with a two-car garage, large unfinished basement space, generator hookup, and brand-new central air system. The rooftop solar system also offers a favorable locked-in lease rate with for transfer to the next owner. Located in one of Middlebury's most sought-after residential neighborhoods, this home offers the space and privacy of an acreage property while remaining convenient to local amenities, and surrounding communities plus the property is within the desirable Region 15 school district. MOTIVATED SELLER!

4 Beds ⋅ 3 Baths ⋅ 24206538 MLS

Looking for a quiet, secluded location? No street noise, no close neighbors? Welcome to 182 Green Hill Road, where space, privacy, and an exceptional Curtis Farms setting come together. Set at the end of a long private driveway on nearly 3 acres, this spacious 4-bedroom, 2.5-bath Colonial offers over 3,000 square feet of living space with an incredible grand living-room with fireplace and vaulted ceiling, perfect for entertaining or relaxing with the family. The main level features hardwood flooring, generous formal living and dining areas, a private office, and a spacious eat-in kitchen with granite countertops and stainless appliances. The primary suite includes a private en-suite bath with Whirlpool tub, separate shower and double vanity. Three additional bedrooms provide plenty of room for family and guests. Enjoy the privacy of the expansive grounds from the large deck, along with a two-car garage, large unfinished basement space, generator hookup, and brand-new central air system. The rooftop solar system also offers a favorable locked-in lease rate with for transfer to the next owner. Located in one of Middlebury's most sought-after residential neighborhoods, this home offers the space and privacy of an acreage property while remaining convenient to local amenities, and surrounding communities plus the property is within the desirable Region 15 school district. MOTIVATED SELLER!

182 Green Hill Rd, Middlebury

$280,000

REDUCED AND PRICED FOR IMMEDIATE SALE! Totally renovated and completely move-in ready! This charming Cape is located in the wonderful town of Middlebury and offers a fantastic alternative to condo living-without the monthly HOA fees. Step inside to a bright, fresh interior where all the work has already been done for you. The updated kitchen features stainless steel appliances, modern finishes, and plenty of natural light. Thoughtfully renovated throughout, this home offers the perfect blend of comfort, style, and low-maintenance living. Whether you're a first-time buyer, looking to downsize, or simply searching for a beautifully updated home in a desirable community, this Middlebury gem is ready for you to move right in and enjoy!

2 Beds ⋅ 1 Baths ⋅ 24205239 MLS

REDUCED AND PRICED FOR IMMEDIATE SALE! Totally renovated and completely move-in ready! This charming Cape is located in the wonderful town of Middlebury and offers a fantastic alternative to condo living-without the monthly HOA fees. Step inside to a bright, fresh interior where all the work has already been done for you. The updated kitchen features stainless steel appliances, modern finishes, and plenty of natural light. Thoughtfully renovated throughout, this home offers the perfect blend of comfort, style, and low-maintenance living. Whether you're a first-time buyer, looking to downsize, or simply searching for a beautifully updated home in a desirable community, this Middlebury gem is ready for you to move right in and enjoy!

327 Steinmann Ave, Middlebury

$350,000

This charming 3-bedroom, 2-full-bath home offers 1,466 square feet of comfortable living space on nearly half an acre, tucked away in a peaceful neighborhood in one of Connecticut's most sought-after communities. Step inside to a welcoming living room featuring hardwood flooring and a generous 6'x3' walk-in closet. The main-level primary bedroom offers the same warmth of hardwood flooring, along with an impressive 6'x5' walk-in closet. A full bathroom with a convenient shower stall is also included on the main level. The eat-in kitchen features hardwood flooring and recessed lighting and flows naturally into a spacious family room designed for relaxing and entertaining. Here, an impressive stone fireplace creates a warm focal point, while brand-new carpeting and two skylights add comfort and natural light. Just beyond the family room, enjoy two covered outdoor spaces-an expansive 19'x16' covered patio on one side and a 17'x7' covered patio on the other-providing plenty of room for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. The second level offers two additional bedrooms, each featuring hardwood flooring, along with another full bathroom enhanced by a skylight that brings in wonderful natural light. A full walk-out basement provides excellent additional space and flexibility, with a newer water heater already in place. This home offers charm, functionality, generous living spaces, and an opportunity to make it your own in beautiful Middlebury!

3 Beds ⋅ 2 Baths ⋅ 24203915 MLS

This charming 3-bedroom, 2-full-bath home offers 1,466 square feet of comfortable living space on nearly half an acre, tucked away in a peaceful neighborhood in one of Connecticut's most sought-after communities. Step inside to a welcoming living room featuring hardwood flooring and a generous 6'x3' walk-in closet. The main-level primary bedroom offers the same warmth of hardwood flooring, along with an impressive 6'x5' walk-in closet. A full bathroom with a convenient shower stall is also included on the main level. The eat-in kitchen features hardwood flooring and recessed lighting and flows naturally into a spacious family room designed for relaxing and entertaining. Here, an impressive stone fireplace creates a warm focal point, while brand-new carpeting and two skylights add comfort and natural light. Just beyond the family room, enjoy two covered outdoor spaces-an expansive 19'x16' covered patio on one side and a 17'x7' covered patio on the other-providing plenty of room for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. The second level offers two additional bedrooms, each featuring hardwood flooring, along with another full bathroom enhanced by a skylight that brings in wonderful natural light. A full walk-out basement provides excellent additional space and flexibility, with a newer water heater already in place. This home offers charm, functionality, generous living spaces, and an opportunity to make it your own in beautiful Middlebury!

138 Steinmann Ave, Middlebury

$574,900

Welcome to 58 Shadduck Road, a renovated Colonial in one of Middlebury's most desirable locations. This move-in-ready home seamlessly blends timeless charm with modern updates, featuring gleaming hardwood floors and a bright open-concept layout. The main level offers a spacious living room with sliders to a large patio, a dining room, a sun-filled kitchen with center island, and a versatile office or sitting area. The second-floor primary suite serves as a private retreat with a luxurious en-suite bath and walk-in closet. Two additional bedrooms and a full bath complete the upper level. Extensive improvements include a newer roof, windows, siding, driveway, electrical, plumbing, central air, propane heating, generator-ready setup, and updated mechanicals. The full basement provides abundant storage. A rare highlight is the detached 3-car garage, offering endless possibilities for car enthusiasts, hobbyists, or additional living space. With its generous footprint and utilities, it presents an excellent opportunity for a future in-law suite, guest quarters, home office, or workshop. A newer storage shed provides additional space. Situated on a picturesque, level lot bordered by mature trees and a charming brook, the property features a private patio perfect for entertaining. Conveniently located just minutes from Middlebury's town center, shopping, restaurants, major highways, and Routes 8 and I-84, this exceptional home combines privacy, flexibility, and convenience.

3 Beds ⋅ 3 Baths ⋅ 24203901 MLS

Welcome to 58 Shadduck Road, a renovated Colonial in one of Middlebury's most desirable locations. This move-in-ready home seamlessly blends timeless charm with modern updates, featuring gleaming hardwood floors and a bright open-concept layout. The main level offers a spacious living room with sliders to a large patio, a dining room, a sun-filled kitchen with center island, and a versatile office or sitting area. The second-floor primary suite serves as a private retreat with a luxurious en-suite bath and walk-in closet. Two additional bedrooms and a full bath complete the upper level. Extensive improvements include a newer roof, windows, siding, driveway, electrical, plumbing, central air, propane heating, generator-ready setup, and updated mechanicals. The full basement provides abundant storage. A rare highlight is the detached 3-car garage, offering endless possibilities for car enthusiasts, hobbyists, or additional living space. With its generous footprint and utilities, it presents an excellent opportunity for a future in-law suite, guest quarters, home office, or workshop. A newer storage shed provides additional space. Situated on a picturesque, level lot bordered by mature trees and a charming brook, the property features a private patio perfect for entertaining. Conveniently located just minutes from Middlebury's town center, shopping, restaurants, major highways, and Routes 8 and I-84, this exceptional home combines privacy, flexibility, and convenience.

58 Shadduck Rd, Middlebury

$409,900

Rare opportunity to own direct waterfront on beautiful Lake Quassapaug! Located in the desirable Tylers Cove community, this charming two-bedroom cottage sits just 50 feet from the water and features its own private dock and yard with direct lake frontage. The cottage is ready for a new owner to bring their ideas and updates-renovate the existing home, explore the possibilities of rebuilding, or simply enjoy it as a classic summer retreat. A special opportunity to experience lakefront living, boating, swimming, and relaxing by the water on one of the area's most beautiful lakes.

2 Beds ⋅ 1 Baths ⋅ 24203525 MLS

Rare opportunity to own direct waterfront on beautiful Lake Quassapaug! Located in the desirable Tylers Cove community, this charming two-bedroom cottage sits just 50 feet from the water and features its own private dock and yard with direct lake frontage. The cottage is ready for a new owner to bring their ideas and updates-renovate the existing home, explore the possibilities of rebuilding, or simply enjoy it as a classic summer retreat. A special opportunity to experience lakefront living, boating, swimming, and relaxing by the water on one of the area's most beautiful lakes.

89 Sandy Beach Road Unit 89, Middlebury

$650,000

Welcome to 285 Southford Rd, a beautiful spacious ranch which checks off all the boxes. Main level living with Open foyer leading into family room w/ gas fireplace, vaulted ceilings, dimmer controlled recessed lighting, and atrium door opening to stone patio. Formal dining room w/ 9 foot ceilings and plenty of natural sunlight. Eat in kitchen has a bow window and table nook area, an abundance of cabinets, granite countertops, built in oven and counter cooktop stove. Hardwood flooring flowing through to Primary bedroom suite complete with trey ceiling, walk in closet, full bath compliments the soaking tub and separate shower stall. 2 bedrooms, full bath and laundry area complete this great floor plan. An added bonus is the office, exercise room or study on the upper level. Full basement and walk in attic commands plenty of storage. Manicured level private lot with heated in the ground pool and hot tub and offering 2 car garage .

3 Beds ⋅ 2 Baths ⋅ 24201753 MLS

Welcome to 285 Southford Rd, a beautiful spacious ranch which checks off all the boxes. Main level living with Open foyer leading into family room w/ gas fireplace, vaulted ceilings, dimmer controlled recessed lighting, and atrium door opening to stone patio. Formal dining room w/ 9 foot ceilings and plenty of natural sunlight. Eat in kitchen has a bow window and table nook area, an abundance of cabinets, granite countertops, built in oven and counter cooktop stove. Hardwood flooring flowing through to Primary bedroom suite complete with trey ceiling, walk in closet, full bath compliments the soaking tub and separate shower stall. 2 bedrooms, full bath and laundry area complete this great floor plan. An added bonus is the office, exercise room or study on the upper level. Full basement and walk in attic commands plenty of storage. Manicured level private lot with heated in the ground pool and hot tub and offering 2 car garage .

285 Southford Rd, Middlebury

$645,000

Welcome to this fabulous one-owner custom-built Cape Cod offering 4 bedrooms, 3.5 baths, and exceptional living space throughout. Beautiful tile and hardwood floors, vaulted ceilings, and a spacious great room with a fireplace and pellet stove create a warm and inviting atmosphere. The first-floor primary suite features a private ensuite bath, while the second floor offers two additional bedrooms, a full bath, and a huge bonus room with endless possibilities for a home office, recreation room, or additional living space. The finished lower level includes an in-law setup with a walkout, providing excellent flexibility for extended family, guests, or additional living space. Enjoy beautiful views across to Long Meadow Pond from the covered rear deck off the great room, or relax and entertain on the expansive patio area. A three-car garage provides plenty of room for vehicles, storage, and hobbies. Additional features include a whole-house propane generator and newer roofs on both the house and shed, installed in 2023. Ideally located in a great setting, this meticulously maintained custom home offers comfort, space, versatility, and beautiful views-truly a special property you'll want to see!

4 Beds ⋅ 4 Baths ⋅ 24202816 MLS

Welcome to this fabulous one-owner custom-built Cape Cod offering 4 bedrooms, 3.5 baths, and exceptional living space throughout. Beautiful tile and hardwood floors, vaulted ceilings, and a spacious great room with a fireplace and pellet stove create a warm and inviting atmosphere. The first-floor primary suite features a private ensuite bath, while the second floor offers two additional bedrooms, a full bath, and a huge bonus room with endless possibilities for a home office, recreation room, or additional living space. The finished lower level includes an in-law setup with a walkout, providing excellent flexibility for extended family, guests, or additional living space. Enjoy beautiful views across to Long Meadow Pond from the covered rear deck off the great room, or relax and entertain on the expansive patio area. A three-car garage provides plenty of room for vehicles, storage, and hobbies. Additional features include a whole-house propane generator and newer roofs on both the house and shed, installed in 2023. Ideally located in a great setting, this meticulously maintained custom home offers comfort, space, versatility, and beautiful views-truly a special property you'll want to see!

46 Washington Dr, Middlebury

$575,000

Welcome to this beautifully updated three-bedroom Cape in the desirable Steeplechase community. Hardwood flooring flows throughout the home, complemented by custom plantation shutters and window treatments in most rooms. The flexible floor plan includes an additional room off the eat-in kitchen. Upstairs, you'll find three spacious bedrooms, two updated baths, and conveniently located laundry. The primary suite features two walk-in closets, while the additional bedrooms offer built-in closet systems. Enjoy the private deck and backyard, plus a full unfinished walkout basement with plenty of potential. Additional highlights include an automatic whole-house Generac generator, natural gas heat, central air, public water and sewer, and a total of 2.5 updated baths. Ideally located on a quiet cul-de-sac, this lovely home is ready for its next owner. Schedule your appointment today!

3 Beds ⋅ 3 Baths ⋅ 24191400 MLS ⋅ Steeplechase BLDG.

Welcome to this beautifully updated three-bedroom Cape in the desirable Steeplechase community. Hardwood flooring flows throughout the home, complemented by custom plantation shutters and window treatments in most rooms. The flexible floor plan includes an additional room off the eat-in kitchen. Upstairs, you'll find three spacious bedrooms, two updated baths, and conveniently located laundry. The primary suite features two walk-in closets, while the additional bedrooms offer built-in closet systems. Enjoy the private deck and backyard, plus a full unfinished walkout basement with plenty of potential. Additional highlights include an automatic whole-house Generac generator, natural gas heat, central air, public water and sewer, and a total of 2.5 updated baths. Ideally located on a quiet cul-de-sac, this lovely home is ready for its next owner. Schedule your appointment today!

16 Caveson Court, Unit 16, Middlebury

$575,000

Welcome to this beautifully updated three-bedroom Cape in the desirable Steeplechase community. Hardwood flooring flows throughout the home, complemented by custom plantation shutters and window treatments in most rooms. The flexible floor plan includes an additional room off the eat-in kitchen. Upstairs, you'll find three spacious bedrooms, two updated baths, and conveniently located laundry. The primary suite features two walk- in closets, while the additional bedrooms offer built-in closet systems. Enjoy the private deck and backyard, plus a full unfinished walkout basement with plenty of potential. Additional highlights include an automatic whole-house Generac generator, natural gas heat, central air, public water and sewer, and a total of 2.5 updated baths. Ideally located on a quiet cul-de-sac, this lovely home is ready for its next owner. Schedule your appointment today!

3 Beds ⋅ 3 Baths ⋅ 24202542 MLS

Welcome to this beautifully updated three-bedroom Cape in the desirable Steeplechase community. Hardwood flooring flows throughout the home, complemented by custom plantation shutters and window treatments in most rooms. The flexible floor plan includes an additional room off the eat-in kitchen. Upstairs, you'll find three spacious bedrooms, two updated baths, and conveniently located laundry. The primary suite features two walk- in closets, while the additional bedrooms offer built-in closet systems. Enjoy the private deck and backyard, plus a full unfinished walkout basement with plenty of potential. Additional highlights include an automatic whole-house Generac generator, natural gas heat, central air, public water and sewer, and a total of 2.5 updated baths. Ideally located on a quiet cul-de-sac, this lovely home is ready for its next owner. Schedule your appointment today!

16 Caveson Court, Unit 16, Middlebury

$219,900

BEST DEAL IN MIDDLEBURY! Motivated seller! Perfect Unit For active 55+ Individual close to the walking trails and a short drive to private recreation beach for swimming, kayaking or canoeing. Nestled in secluded area cul de sac this Middlebury, 55+ community is in Excellent Condition. All appliances included. Small complex. Bright and Well kept Second floor Unit. Living room dining room combo. New deck. central air. heat pump furnace. Clubhouse on property. Conveniently located close to town center.

1 Beds ⋅ 1 Baths ⋅ 24202228 MLS ⋅ Middlebury Commons BLDG.

BEST DEAL IN MIDDLEBURY! Motivated seller! Perfect Unit For active 55+ Individual close to the walking trails and a short drive to private recreation beach for swimming, kayaking or canoeing. Nestled in secluded area cul de sac this Middlebury, 55+ community is in Excellent Condition. All appliances included. Small complex. Bright and Well kept Second floor Unit. Living room dining room combo. New deck. central air. heat pump furnace. Clubhouse on property. Conveniently located close to town center.

35 Nutmeg Rd Unit B2, Middlebury

$439,900

Welcome Home to this nicely updated New England Cape style home with a comfortable and convenient layout. This move-in ready home offers 4 bedrooms and 2 full bathrooms. An inviting living room showcases a fireplace creating a warm and cozy gathering space for the whole family, adjoining dining area leads to The large kitchen includes ample workspace, lots of cabinets and tile flooring, with easy access to the large deck, and back yard-perfect for all your outdoor entertaining. Two bedrooms, and recently renovated full bath and hardwood floors complete the main level. As you walk upstairs you will find a Full remodeled bathroom, A bedroom and A large primary bedroom, with vaulted ceilings, slider to balcony overlooking your landscaped back yard, A large closet, hardwood floors and fresh paint finish out this fabulous space. Added bonuses include full walk out basement into one car garage, ample storage, large shed and parking for the whole family. Don't miss out on the chance to make this move-in ready home yours! It is close to Route 84 and Middlebury walking trail. Welcome to Middlebury and their award- winning region 15 school.

4 Beds ⋅ 2 Baths ⋅ 24200006 MLS

Welcome Home to this nicely updated New England Cape style home with a comfortable and convenient layout. This move-in ready home offers 4 bedrooms and 2 full bathrooms. An inviting living room showcases a fireplace creating a warm and cozy gathering space for the whole family, adjoining dining area leads to The large kitchen includes ample workspace, lots of cabinets and tile flooring, with easy access to the large deck, and back yard-perfect for all your outdoor entertaining. Two bedrooms, and recently renovated full bath and hardwood floors complete the main level. As you walk upstairs you will find a Full remodeled bathroom, A bedroom and A large primary bedroom, with vaulted ceilings, slider to balcony overlooking your landscaped back yard, A large closet, hardwood floors and fresh paint finish out this fabulous space. Added bonuses include full walk out basement into one car garage, ample storage, large shed and parking for the whole family. Don't miss out on the chance to make this move-in ready home yours! It is close to Route 84 and Middlebury walking trail. Welcome to Middlebury and their award- winning region 15 school.

106 Steinmann Ave, Middlebury

$749,900

Privacy, charm, and timeless craftsmanship define this exceptional Contemporary Craftsman on 1.5 acres in Middlebury's Historic District. Bordering the 9+ acre Crest Preserve, this 2,600+ sq. ft. home offers 4 bedrooms, 3.5 baths, a spacious living room, and a large family room with a flexible floor plan. Character abounds with original hand-carved staircases, hardwood floors, colonial shutters, reading nooks, and a finished attic, while thoughtful updates include a recently painted interior, updated baths, upgraded electrical, central air, gas fireplace insert, and a chef's kitchen with quartz countertops, double ovens, and stainless-steel appliances. Picture windows overlook the private backyard oasis featuring two Bluestone patios, a Belgian block patio, and a renovated Gunite saltwater pool with waterfall, newer mechanicals, and fencing. Exterior improvements include newer siding, roof, chimney, barn-style lighting, and professional landscaping. Surrounded by protected woodlands and the sounds of nearby church bells, this one-of-a-kind home offers the perfect blend of historic character, modern updates, and peaceful New England living.

4 Beds ⋅ 4 Baths ⋅ 24193938 MLS

Privacy, charm, and timeless craftsmanship define this exceptional Contemporary Craftsman on 1.5 acres in Middlebury's Historic District. Bordering the 9+ acre Crest Preserve, this 2,600+ sq. ft. home offers 4 bedrooms, 3.5 baths, a spacious living room, and a large family room with a flexible floor plan. Character abounds with original hand-carved staircases, hardwood floors, colonial shutters, reading nooks, and a finished attic, while thoughtful updates include a recently painted interior, updated baths, upgraded electrical, central air, gas fireplace insert, and a chef's kitchen with quartz countertops, double ovens, and stainless-steel appliances. Picture windows overlook the private backyard oasis featuring two Bluestone patios, a Belgian block patio, and a renovated Gunite saltwater pool with waterfall, newer mechanicals, and fencing. Exterior improvements include newer siding, roof, chimney, barn-style lighting, and professional landscaping. Surrounded by protected woodlands and the sounds of nearby church bells, this one-of-a-kind home offers the perfect blend of historic character, modern updates, and peaceful New England living.

77 Crest Rd, Middlebury

$499,900

Welcome home to this beautifully updated property located in one of Middlebury's quiet and sought after neighborhoods. This move in ready home features a stylish kitchen with granite countertops, a gas range, and smart appliances, including a refrigerator, washer and dryer. Gleaming hardwood floors in living room, hallway and bedrooms. Enjoy year-round comfort with central air conditioning and peace of mind with a generator hookup and included generator. Fresh paint throughout and a completely renovated lower level provide modern, versatile living space. Step outside to a low-maintenance Trex deck and almost a half acre yard, perfect for relaxing or entertaining. Conveniently located near schools, parks, walking trails, and major highways, with local vineyards, fine dining, and all that Middlebury has to offer just minutes away.

3 Beds ⋅ 2 Baths ⋅ 24195720 MLS

Welcome home to this beautifully updated property located in one of Middlebury's quiet and sought after neighborhoods. This move in ready home features a stylish kitchen with granite countertops, a gas range, and smart appliances, including a refrigerator, washer and dryer. Gleaming hardwood floors in living room, hallway and bedrooms. Enjoy year-round comfort with central air conditioning and peace of mind with a generator hookup and included generator. Fresh paint throughout and a completely renovated lower level provide modern, versatile living space. Step outside to a low-maintenance Trex deck and almost a half acre yard, perfect for relaxing or entertaining. Conveniently located near schools, parks, walking trails, and major highways, with local vineyards, fine dining, and all that Middlebury has to offer just minutes away.

112 Joy Rd, Middlebury

$474,500

Cottage Colonial close to town center, parks and more in beautiful Middlebury CT! This 1929 build charmer has stunning details both inside and out. Lovingly cared for, the pride of ownership of this property is evident upon arrival. Note the unique features including: Hardwood flooring throughout main and upper levels, sunken family room w/wood panel vaulted ceiling and slider to deck, wood burning fireplace in the Parlor/Living room. Kitchen boasts granite countertops, stainless appliances (newer Dishwasher & Range) and breakfast bar. Stunning Dining room with corner built ins reminiscent of bygone days offers a special gathering spot. Combo Laundry/Powder room and Office also on main level. Upstairs there are 2 good sized bedrooms with hall bath. Then a surprise 3rd level finished room w/electric heat. Ideal extra space to enjoy (play room, music room, reading room, you choose!). Step outside to enjoy the lovely wraparound deck with Pergola and Garage/Shed for lawn equipment, tools or even a possible gardening shed! Generator hook-up in place. City water and sewer too. Book your appt. and see this gem of a home for yourself soon!

2 Beds ⋅ 2 Baths ⋅ 24194436 MLS

Cottage Colonial close to town center, parks and more in beautiful Middlebury CT! This 1929 build charmer has stunning details both inside and out. Lovingly cared for, the pride of ownership of this property is evident upon arrival. Note the unique features including: Hardwood flooring throughout main and upper levels, sunken family room w/wood panel vaulted ceiling and slider to deck, wood burning fireplace in the Parlor/Living room. Kitchen boasts granite countertops, stainless appliances (newer Dishwasher & Range) and breakfast bar. Stunning Dining room with corner built ins reminiscent of bygone days offers a special gathering spot. Combo Laundry/Powder room and Office also on main level. Upstairs there are 2 good sized bedrooms with hall bath. Then a surprise 3rd level finished room w/electric heat. Ideal extra space to enjoy (play room, music room, reading room, you choose!). Step outside to enjoy the lovely wraparound deck with Pergola and Garage/Shed for lawn equipment, tools or even a possible gardening shed! Generator hook-up in place. City water and sewer too. Book your appt. and see this gem of a home for yourself soon!

47 Middlebury Ter, Middlebury

$324,900

Welcome to this Middlebury home offering the perfect blend of comfort, functionality, and a desirable location. The home's refreshed interior provides move-in-ready feel designed for everyday living. The property is an excellent opportunity for buyers looking for a home that is ready to enjoy. The home sits on a level lot and is situated directly next to a small brook.

2 Beds ⋅ 2 Baths ⋅ 24193924 MLS

Welcome to this Middlebury home offering the perfect blend of comfort, functionality, and a desirable location. The home's refreshed interior provides move-in-ready feel designed for everyday living. The property is an excellent opportunity for buyers looking for a home that is ready to enjoy. The home sits on a level lot and is situated directly next to a small brook.

125 Shadduck Rd, Middlebury

$339,900

Picture-perfect and completely updated, this classic New England Cape delivers far more than its footprint suggests. A paver walkway, lamppost, and lush hosta gardens frame a storybook exterior with black shutters and stone front steps - genuine curb appeal on one of Middlebury's most established streets. Inside, the open floor plan connects a sun-filled living area to a fully renovated kitchen featuring a quartz-topped center island with seating, two-tone cabinetry with brass hardware, stainless appliances, and a wall of windows overlooking the green backdrop beyond. Crown molding, designer lighting, and thoughtful finishes carry throughout - every detail has been done, so you simply move in. Two bedrooms and a full bath complete this efficient, light-filled layout. Steps from the Middlebury Greenway Trail with easy Route 64 and I-84 access, and served by the award-winning Region 15 school district. A turnkey Connecticut gem.

2 Beds ⋅ 1 Baths ⋅ 24113785 MLS

Picture-perfect and completely updated, this classic New England Cape delivers far more than its footprint suggests. A paver walkway, lamppost, and lush hosta gardens frame a storybook exterior with black shutters and stone front steps - genuine curb appeal on one of Middlebury's most established streets. Inside, the open floor plan connects a sun-filled living area to a fully renovated kitchen featuring a quartz-topped center island with seating, two-tone cabinetry with brass hardware, stainless appliances, and a wall of windows overlooking the green backdrop beyond. Crown molding, designer lighting, and thoughtful finishes carry throughout - every detail has been done, so you simply move in. Two bedrooms and a full bath complete this efficient, light-filled layout. Steps from the Middlebury Greenway Trail with easy Route 64 and I-84 access, and served by the award-winning Region 15 school district. A turnkey Connecticut gem.

12 Yale Ave, Middlebury

$449,900

Set on nearly half an acre in one of Middlebury's most desirable neighborhoods, this 3-bedroom, 2.5-bath Colonial blends timeless character with everyday comfort. Gleaming hardwood floors run throughout the home, anchoring an open, inviting layout built for both daily living and entertaining. The heart of the home is a spacious family room crowned by a dramatic cathedral ceiling and ceiling fan, a bright and airy retreat that flows naturally into the rest of the main level. The kitchen is ready to cook in and gather around, featuring granite countertops, a breakfast bar, and stainless appliances including a gas cooktop. Generous living and dining rooms round out the main floor, each finished in warm hardwood. Upstairs, the primary bedroom suite offers a private full bath and walk-in closet, with two additional well-sized bedrooms, one with its own walk-in closet. A cozy fireplace, central air, thermopane windows, and zoned heating add year-round comfort and efficiency. Outside, enjoy a level, open lot with plenty of room to play, garden, or relax. A full unfinished basement with garage access and a one-car under-house garage provide ample storage and expansion potential. A brand new basement system was installed on 7/14/26, adding to peace of mind.

3 Beds ⋅ 3 Baths ⋅ 24191937 MLS

Set on nearly half an acre in one of Middlebury's most desirable neighborhoods, this 3-bedroom, 2.5-bath Colonial blends timeless character with everyday comfort. Gleaming hardwood floors run throughout the home, anchoring an open, inviting layout built for both daily living and entertaining. The heart of the home is a spacious family room crowned by a dramatic cathedral ceiling and ceiling fan, a bright and airy retreat that flows naturally into the rest of the main level. The kitchen is ready to cook in and gather around, featuring granite countertops, a breakfast bar, and stainless appliances including a gas cooktop. Generous living and dining rooms round out the main floor, each finished in warm hardwood. Upstairs, the primary bedroom suite offers a private full bath and walk-in closet, with two additional well-sized bedrooms, one with its own walk-in closet. A cozy fireplace, central air, thermopane windows, and zoned heating add year-round comfort and efficiency. Outside, enjoy a level, open lot with plenty of room to play, garden, or relax. A full unfinished basement with garage access and a one-car under-house garage provide ample storage and expansion potential. A brand new basement system was installed on 7/14/26, adding to peace of mind.

42 White Ave, Middlebury

$670,000

Well-maintained, single-owner Center Hall Colonial located on a corner lot in an established neighborhood. This 4-bedroom, 2.5-bath home offers a functional floor plan, a 2-car garage and central air. The main level features a formal living room and dining room, an updated eat-in kitchen with new granite counters, tile backsplash, new stainless steel appliances, and a slider to the deck. The kitchen opens to the family room with a fireplace, creating a comfortable gathering space. A half bath completes the first floor. Upstairs you'll find 4 bedrooms, including a primary suite with two walk-in closets and a full bath with a corner tub. The second-floor laundry adds everyday convenience. The unfinished walk-out basement offers excellent storage and future expansion potential. Outside, enjoy the deck, patio, and private backyard. Conveniently located in the award-winning Region 15 school district and close to parks, schools, the library, shopping, restaurants, and major commuter routes. A move-in ready home in a sought-after neighborhood.

4 Beds ⋅ 3 Baths ⋅ 24191383 MLS

Well-maintained, single-owner Center Hall Colonial located on a corner lot in an established neighborhood. This 4-bedroom, 2.5-bath home offers a functional floor plan, a 2-car garage and central air. The main level features a formal living room and dining room, an updated eat-in kitchen with new granite counters, tile backsplash, new stainless steel appliances, and a slider to the deck. The kitchen opens to the family room with a fireplace, creating a comfortable gathering space. A half bath completes the first floor. Upstairs you'll find 4 bedrooms, including a primary suite with two walk-in closets and a full bath with a corner tub. The second-floor laundry adds everyday convenience. The unfinished walk-out basement offers excellent storage and future expansion potential. Outside, enjoy the deck, patio, and private backyard. Conveniently located in the award-winning Region 15 school district and close to parks, schools, the library, shopping, restaurants, and major commuter routes. A move-in ready home in a sought-after neighborhood.

10 Curtis Rd, Middlebury

$520,000

Experience the beauty of waterfront living in this charming 3-bedroom, 2-bath Cape Cod-style home nestled along Long Meadow Pond. Combining timeless character with thoughtful updates, this inviting home offers the perfect balance of comfort, convenience, and year-round recreation. Inside, you'll find warm and welcoming living spaces highlighted by a cozy fireplace-perfect for relaxing on cool New England evenings. The functional floor plan offers three comfortable bedrooms, two full bathrooms, and abundant natural light throughout. Recent improvements provide peace of mind and added value, including a new roof, new sewer connection, and a spacious new deck overlooking the water. Step outside to enjoy stunning pond views, entertain guests on the deck, or head down to your private dock for kayaking, fishing, paddleboarding, or simply taking in the tranquil surroundings. Whether you're looking for a full-time residence or a peaceful weekend escape, this waterfront gem offers a rare opportunity to enjoy the natural beauty of Long Meadow Pond while remaining just minutes from shopping, restaurants, parks, and major commuter routes.

3 Beds ⋅ 2 Baths ⋅ 24191194 MLS

Experience the beauty of waterfront living in this charming 3-bedroom, 2-bath Cape Cod-style home nestled along Long Meadow Pond. Combining timeless character with thoughtful updates, this inviting home offers the perfect balance of comfort, convenience, and year-round recreation. Inside, you'll find warm and welcoming living spaces highlighted by a cozy fireplace-perfect for relaxing on cool New England evenings. The functional floor plan offers three comfortable bedrooms, two full bathrooms, and abundant natural light throughout. Recent improvements provide peace of mind and added value, including a new roof, new sewer connection, and a spacious new deck overlooking the water. Step outside to enjoy stunning pond views, entertain guests on the deck, or head down to your private dock for kayaking, fishing, paddleboarding, or simply taking in the tranquil surroundings. Whether you're looking for a full-time residence or a peaceful weekend escape, this waterfront gem offers a rare opportunity to enjoy the natural beauty of Long Meadow Pond while remaining just minutes from shopping, restaurants, parks, and major commuter routes.

326 Lake Shore Dr, Middlebury

$529,900

Welcome to 10 Ridgewood Drive in Middlebury, located in the highly sought-after Ridgewood community, offering exceptional amenities including a clubhouse, swimming pool & tennis courts. This beautifully maintained townhouse is being offered for sale by its original owner and has been extensively remodeled throughout. The main level features an open-concept floor plan designed for today's lifestyle, with gleaming hardwood floors and a convenient first-floor half bath. The updated eat-in kitchen boasts granite countertops, stainless steel appliances and direct access to a private deck perfect for relaxing or entertaining. The second floor offers 3 generously sized bedrooms and 2 full baths. The spacious primary suite features a walk-in closet, double vanity, soaking tub, and separate shower. A conveniently located second-floor laundry area with washer and dryer adds to the home's functionality. Need even more living space? The finished third-floor loft provides endless possibilities as a home office, fitness area, or guest suite. Additional features includes a 1-car garage, full basement offering abundant storage, and an efficient three-zone heating and cooling system, allowing you to maximizing energy efficiency. Ideally situated near the community clubhouse and pool, and just minutes from shopping, restaurants, walking trails and major highways, this exceptional home offers the perfect combination of comfort, style, and convenience in one of Middlebury's premier communitie

3 Beds ⋅ 3 Baths ⋅ 24186753 MLS ⋅ Ridgewood At Middlebury BLDG.

Welcome to 10 Ridgewood Drive in Middlebury, located in the highly sought-after Ridgewood community, offering exceptional amenities including a clubhouse, swimming pool & tennis courts. This beautifully maintained townhouse is being offered for sale by its original owner and has been extensively remodeled throughout. The main level features an open-concept floor plan designed for today's lifestyle, with gleaming hardwood floors and a convenient first-floor half bath. The updated eat-in kitchen boasts granite countertops, stainless steel appliances and direct access to a private deck perfect for relaxing or entertaining. The second floor offers 3 generously sized bedrooms and 2 full baths. The spacious primary suite features a walk-in closet, double vanity, soaking tub, and separate shower. A conveniently located second-floor laundry area with washer and dryer adds to the home's functionality. Need even more living space? The finished third-floor loft provides endless possibilities as a home office, fitness area, or guest suite. Additional features includes a 1-car garage, full basement offering abundant storage, and an efficient three-zone heating and cooling system, allowing you to maximizing energy efficiency. Ideally situated near the community clubhouse and pool, and just minutes from shopping, restaurants, walking trails and major highways, this exceptional home offers the perfect combination of comfort, style, and convenience in one of Middlebury's premier communitie

10 Ridgewood Dr Unit 10, Middlebury

$649,900

MOTIVATED SELLERS! MAKE OFFER! Nestled on 1.22 acres of park-like grounds, a large custom designed home offering privacy & serenity and maintained by its original owners. Step inside and be greeted by a sunken, front-to-back living room anchored by a fireplace, setting the tone for the thoughtful design found throughout. Entertain in style in the formal dining room with elegant French doors or gather in the huge family room- another fireplace and generous proportions make it the heart of the home. The eat-in kitchen features a breakfast bar, perfect for casual mornings. Three bedrooms, 2.5 baths, and 3 fireplaces offer the comfort and warmth your family deserves. And, when you want to escape, a finished mancave with wet bar is all yours. Outside, a 54-foot deck provides the ultimate backdrop for outdoor entertaining, overlooking your own private retreat. Three oversized garages and newly paved driveway add convenience and curb appeal alike. Oh, and by the way, please do not forget to walk up a couple of steps behind the deck to a beautiful level lot adjacent to a tree lined area. Perfect for incorporating your very own fire pit or gazebo, for further relaxation and enjoyment. Recent updates including a new whole-house generator (1 yr), deck (3 yrs), electric hot water heater (3 yrs), paved driveway (2 yr), and a 15-year roof. Located in the New England town of Middlebury, known for its small-town character and top-rated schools. MOTIVATED SELLERS! MAKE OFFER!

3 Beds ⋅ 3 Baths ⋅ 24185515 MLS

MOTIVATED SELLERS! MAKE OFFER! Nestled on 1.22 acres of park-like grounds, a large custom designed home offering privacy & serenity and maintained by its original owners. Step inside and be greeted by a sunken, front-to-back living room anchored by a fireplace, setting the tone for the thoughtful design found throughout. Entertain in style in the formal dining room with elegant French doors or gather in the huge family room- another fireplace and generous proportions make it the heart of the home. The eat-in kitchen features a breakfast bar, perfect for casual mornings. Three bedrooms, 2.5 baths, and 3 fireplaces offer the comfort and warmth your family deserves. And, when you want to escape, a finished mancave with wet bar is all yours. Outside, a 54-foot deck provides the ultimate backdrop for outdoor entertaining, overlooking your own private retreat. Three oversized garages and newly paved driveway add convenience and curb appeal alike. Oh, and by the way, please do not forget to walk up a couple of steps behind the deck to a beautiful level lot adjacent to a tree lined area. Perfect for incorporating your very own fire pit or gazebo, for further relaxation and enjoyment. Recent updates including a new whole-house generator (1 yr), deck (3 yrs), electric hot water heater (3 yrs), paved driveway (2 yr), and a 15-year roof. Located in the New England town of Middlebury, known for its small-town character and top-rated schools. MOTIVATED SELLERS! MAKE OFFER!

70 Pine Hollow Dr, Middlebury

$590,000

This beautifully maintained Vintage Colonial blends historic charm with thoughtful updates. Built-in equity! Recent appraisal values this home at $715,000. Set on 1.25 meticulously landscaped acres, this 4-bedroom, 3-bath home offers warmth, space, and versatility with a huge finished attic space. The stunning grounds feature mature plantings, classic New England stone walls, and inviting patio spaces that create a private outdoor retreat ideal for relaxing or entertaining. Easily accessed from the kitchen, the outdoor living areas offer seamless flow for gatherings, dining, and enjoying the peaceful setting. Inside, the updated eat-in kitchen features a fireplace with pellet stove insert, while the formal living room offers a second fireplace and the bright sunroom provides flexible living space. A separate outbuilding/studio expands the possibilities-perfect for an artist, home office, workshop, guest space, or easily converted into a detached in-law setup. Extensive updates include newer windows, updated plumbing, replaced well pump and pressure tank, newer oil tank, furnace burner replacement, exterior painting, new appliances, renovated studio/office, and a full first-floor bath. The main level has been updated with sheetrock replacing original plaster walls and ceilings, while the upper level retains its original plaster craftsmanship and antique character. A rare opportunity to own historic beauty, modern function, and value-without historic district restrictions

4 Beds ⋅ 3 Baths ⋅ 24184437 MLS

This beautifully maintained Vintage Colonial blends historic charm with thoughtful updates. Built-in equity! Recent appraisal values this home at $715,000. Set on 1.25 meticulously landscaped acres, this 4-bedroom, 3-bath home offers warmth, space, and versatility with a huge finished attic space. The stunning grounds feature mature plantings, classic New England stone walls, and inviting patio spaces that create a private outdoor retreat ideal for relaxing or entertaining. Easily accessed from the kitchen, the outdoor living areas offer seamless flow for gatherings, dining, and enjoying the peaceful setting. Inside, the updated eat-in kitchen features a fireplace with pellet stove insert, while the formal living room offers a second fireplace and the bright sunroom provides flexible living space. A separate outbuilding/studio expands the possibilities-perfect for an artist, home office, workshop, guest space, or easily converted into a detached in-law setup. Extensive updates include newer windows, updated plumbing, replaced well pump and pressure tank, newer oil tank, furnace burner replacement, exterior painting, new appliances, renovated studio/office, and a full first-floor bath. The main level has been updated with sheetrock replacing original plaster walls and ceilings, while the upper level retains its original plaster craftsmanship and antique character. A rare opportunity to own historic beauty, modern function, and value-without historic district restrictions

700 Watertown Rd, Middlebury

$649,900

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.

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

$660,000

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.

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

$585,000

A piece of New England History on Fenn Pond. Circa 1803 "Todt Farm" is a truly distinctive center-hall Colonial set in an extraordinary Middlebury setting overlooking and adjacent to Fenn Pond. Surround by Middlebury Land Trust land, with preserved Brookdale Farm across the road, the property offers a rare sense of privacy, beauty and permanence. Inside, centuries-old character takes center stage with wide-board floors, seven fireplaces, rich horizontal paneling, built-ins, classic 12-over-12 windows and beautifully preserved front and rear staircases. The 11-room, 4-bedroom home pairs authentic architectural detail with the comforts of today, including a welcoming sunroom, stone patio, attached two-bay garage and 20kW Generac generator. Mature trees, gardens, stone walls and rolling lawns frame the home, while the pond setting creates an unmistakable sense of place. A rare opportunity to own an authentic piece of Connecticut history in one of Middlebury's most picturesque settings.

4 Beds ⋅ 4 Baths ⋅ 24164662 MLS

A piece of New England History on Fenn Pond. Circa 1803 "Todt Farm" is a truly distinctive center-hall Colonial set in an extraordinary Middlebury setting overlooking and adjacent to Fenn Pond. Surround by Middlebury Land Trust land, with preserved Brookdale Farm across the road, the property offers a rare sense of privacy, beauty and permanence. Inside, centuries-old character takes center stage with wide-board floors, seven fireplaces, rich horizontal paneling, built-ins, classic 12-over-12 windows and beautifully preserved front and rear staircases. The 11-room, 4-bedroom home pairs authentic architectural detail with the comforts of today, including a welcoming sunroom, stone patio, attached two-bay garage and 20kW Generac generator. Mature trees, gardens, stone walls and rolling lawns frame the home, while the pond setting creates an unmistakable sense of place. A rare opportunity to own an authentic piece of Connecticut history in one of Middlebury's most picturesque settings.

66 Artillery Rd, Middlebury