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At 783 Whittemore Road, beautifully detailed living spaces are paired with something rarely found in a residential property: an expansive garage with room for far more than everyday parking. Extensively rebuilt in 2010, this Middlebury home offers five bedrooms, three full baths, and remarkable flexibility across its living and utility spaces. Beneath the main living level, the multi-vehicle garage offers substantial room for automobile collections, restoration projects, recreational equipment, and a personal workshop. It's a defining feature for a property where practicality and distinctive design share equal billing. Upstairs, vaulted ceilings, exposed beams, skylights, and blue and green zinc paneling lend architectural character throughout. The kitchen features solid wood cabinetry, a professional gas range, French-door wall oven, convection oven, dual Sub-Zero refrigerators, a separate freezer, and two dishwashers, opening to the dining and family rooms. Radiant-heated hardwood floors distinguish the family room. The primary suite includes a sitting area, two walk-in closets, and a bath with heated floors, soaking tub, oversized shower, and heated towel bars. Additional rooms provide flexibility for living or working, complemented by built-in storage and dedicated laundry. A distinctive combination of craftsmanship, comfortable living, and exceptional space for the things that matter beyond the front door.

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24213699 MLS

At 783 Whittemore Road, beautifully detailed living spaces are paired with something rarely found in a residential property: an expansive garage with room for far more than everyday parking. Extensively rebuilt in 2010, this Middlebury home offers five bedrooms, three full baths, and remarkable flexibility across its living and utility spaces. Beneath the main living level, the multi-vehicle garage offers substantial room for automobile collections, restoration projects, recreational equipment, and a personal workshop. It's a defining feature for a property where practicality and distinctive design share equal billing. Upstairs, vaulted ceilings, exposed beams, skylights, and blue and green zinc paneling lend architectural character throughout. The kitchen features solid wood cabinetry, a professional gas range, French-door wall oven, convection oven, dual Sub-Zero refrigerators, a separate freezer, and two dishwashers, opening to the dining and family rooms. Radiant-heated hardwood floors distinguish the family room. The primary suite includes a sitting area, two walk-in closets, and a bath with heated floors, soaking tub, oversized shower, and heated towel bars. Additional rooms provide flexibility for living or working, complemented by built-in storage and dedicated laundry. A distinctive combination of craftsmanship, comfortable living, and exceptional space for the things that matter beyond the front door.

783 Whittemore Rd, Middlebury

$479,900

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 ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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

Custom finishes throughout, down to the smart toilet, in this move-in ready 1941 Cape with original character. The kitchen has custom cabinetry, black stone counters, bamboo floors and a sunlit bay window, and original hardwood floors run through the living and dining rooms. Both full baths have black-stone finishes; the primary bath has a double vanity, warm wood, perimeter floor lighting and a waterfall/body-jet shower. Custom built-ins add storage upstairs. The finished lower level offers a second living area, office/gym space, laundry and storage. Out back, the deck opens to a large, tree-lined 0.34-acre yard. Multi-zone ductless heat and AC, with an oil boiler as backup heat. Roof approx. 10 years old. Detached garage. One-year home warranty included, extendable to three. Region 15 schools and convenient I-84 access.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24209861 MLS

Custom finishes throughout, down to the smart toilet, in this move-in ready 1941 Cape with original character. The kitchen has custom cabinetry, black stone counters, bamboo floors and a sunlit bay window, and original hardwood floors run through the living and dining rooms. Both full baths have black-stone finishes; the primary bath has a double vanity, warm wood, perimeter floor lighting and a waterfall/body-jet shower. Custom built-ins add storage upstairs. The finished lower level offers a second living area, office/gym space, laundry and storage. Out back, the deck opens to a large, tree-lined 0.34-acre yard. Multi-zone ductless heat and AC, with an oil boiler as backup heat. Roof approx. 10 years old. Detached garage. One-year home warranty included, extendable to three. Region 15 schools and convenient I-84 access.

314 Porter Ave, Middlebury

$650,000

Pride of ownership and tasteful updates shine throughout this lovingly maintained, one-owner Colonial in the desirable Curtis Farms subdivision. Set on a corner lot in an established dead-end neighborhood, this 4-bedroom, 2.5-bath home offers a welcoming setting close to schools, parks, and major highways. The main level features formal living and dining rooms and an updated eat-in kitchen with new granite counters, a tile backsplash, and new stainless steel appliances. The kitchen opens to a comfortable family room with a fireplace, while sliding doors lead to the deck for easy outdoor dining and entertaining. A half bath completes the first floor. Upstairs, the primary suite offers two walk-in closets and a full bath with a corner tub. Three additional bedrooms and second-floor laundry provide space and everyday convenience. Central air and a 2-car garage add to the home's appeal, while the unfinished walk-out basement offers generous storage and potential for future finished space. Enjoy the deck, patio, and private backyard, along with a location in the Region 15 school district near schools, parks, the library, shopping, and restaurants. A move-in-ready home offering comfort, thoughtful updates, and convenient commuter access in sought-after Curtis Farms.

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24191383 MLS

Pride of ownership and tasteful updates shine throughout this lovingly maintained, one-owner Colonial in the desirable Curtis Farms subdivision. Set on a corner lot in an established dead-end neighborhood, this 4-bedroom, 2.5-bath home offers a welcoming setting close to schools, parks, and major highways. The main level features formal living and dining rooms and an updated eat-in kitchen with new granite counters, a tile backsplash, and new stainless steel appliances. The kitchen opens to a comfortable family room with a fireplace, while sliding doors lead to the deck for easy outdoor dining and entertaining. A half bath completes the first floor. Upstairs, the primary suite offers two walk-in closets and a full bath with a corner tub. Three additional bedrooms and second-floor laundry provide space and everyday convenience. Central air and a 2-car garage add to the home's appeal, while the unfinished walk-out basement offers generous storage and potential for future finished space. Enjoy the deck, patio, and private backyard, along with a location in the Region 15 school district near schools, parks, the library, shopping, and restaurants. A move-in-ready home offering comfort, thoughtful updates, and convenient commuter access in sought-after Curtis Farms.

10 Curtis Rd, 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, newer oil tank, furnace burner replaced, 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 ⋅ ACTIVE Status ⋅ 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, newer oil tank, furnace burner replaced, 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

$239,900

SHOVEL READY! LAST AVAILABLE HOMESITE IN THIS UPSCALE SUBDIVISION OF FINER HOMES. PUBLIC WATER & SEWER LATERALS ALREADY EXTENDED TO PROPERTY. CLOSE TO EVERYTHING, BUT EXTREMELY PRIVATE. MINIMUM SQ FOOTAGE 2800SF.

ACTIVE Status ⋅ 24152556 MLS

SHOVEL READY! LAST AVAILABLE HOMESITE IN THIS UPSCALE SUBDIVISION OF FINER HOMES. PUBLIC WATER & SEWER LATERALS ALREADY EXTENDED TO PROPERTY. CLOSE TO EVERYTHING, BUT EXTREMELY PRIVATE. MINIMUM SQ FOOTAGE 2800SF.

75 Gleneagle Rd, Middlebury

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