Middlebury, CT homes for sale & real estate

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COMING SOON

126 Colonial Ave, Middlebury, CT 06762
126 Colonial Ave, Middlebury, CT 06762
126 Colonial Ave, Middlebury, CT 06762
ABOUT THIS HOME
Middlebury, CT Homes for Sale
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. (Some photos are from a previous listing so that the exterior shows the landscape. )

$639,000

3 beds1.5 baths2,531 sq ft

126 Colonial Ave, Middlebury, CT 06762

2.4 acre lot • 2 garage spots • Car-dependent

OPEN SAT, 12PM TO 2PM

7 Arrowwood Ct #7, Middlebury, CT 06762
7 Arrowwood Ct #7, Middlebury, CT 06762
7 Arrowwood Ct #7, Middlebury, CT 06762
ABOUT THIS HOME
Middlebury, CT Homes for Sale
Discover luxury living in this beautifully upgraded end-unit condo located in the sought-after Ridgewood of Middlebury community. With 2,643 sq. ft. , this spacious home offers 3 bedrooms, 3 full baths, and 1 half bath, providing ample space and comfort. Step inside to a traditional open floor plan featuring a gourmet kitchen with an over sized island, granite countertops, a gas stove, and high-end finishes throughout. Both family room with gas fireplace and loft area are equipped with built in stereo speakers with surround sound. The inviting living and dining areas flow seamlessly, perfect for entertaining. The spacious primary suite boasts a large walk in closet, generous master bath wit

$650,000

3 beds2.5 baths2,643 sq ft

7 Arrowwood Ct #7, Middlebury, CT 06762

$515 HOA • 2 garage spots • Pool

COMING SOON

138 Skyline Dr, Middlebury, CT 06762
138 Skyline Dr, Middlebury, CT 06762
138 Skyline Dr, Middlebury, CT 06762
ABOUT THIS HOME
Middlebury, CT Homes for Sale
Welcome to 138 Skyline Dr, Middlebury, CT a beautifully maintained ranch-style home with a finished basement and in-law suite! This home offers the perfect blend of comfort, convenience, and versatility. Step inside the main level to find three spacious bedrooms, plus a bedroom and bathroom downstairs, a bright living area, and a well-appointed kitchen. The finished lower level provides a fantastic in-law suite, perfect for extended family or guests. Outside, the large backyard offers endless possibilities whether you're looking to entertain, garden, or simply relax. A two-car garage and a long driveway provide ample parking. Situated in a peaceful neighborhood yet conveniently close to sch

$695,000

3 beds2.5 baths2,212 sq ft

138 Skyline Dr, Middlebury, CT 06762

3.86 acre lot • 2 garage spots • Car-dependent

29 Winding Trl #29, Middlebury, CT 06762
29 Winding Trl #29, Middlebury, CT 06762
29 Winding Trl #29, Middlebury, CT 06762
ABOUT THIS HOME
Middlebury, CT Homes for Sale
Beautiful Portman Condo in Sought-After Ridgewood Community. Discover this stunning 3-bedroom, 2.5-bath condo built by Toll Brothers, nestled on a private cul-de-sac street in unique location. Boasting over 2,100 sqft of thoughtfully designed living space, this home includes a 3-foot bump-out for added size. Entering the home, the first floor features an open floor plan w/ hardwood floors, white cabinetry, stainless steel appliances, perfect for modern living, an upgraded skylight in kitchen floods the space with natural light. Off the kitchen is a private deck with wooded views & a large living room w/ a gas fireplace. Upstairs the spacious primary suite offers a walk-in closet and a

$565,000

3 beds2.5 baths2,130 sq ft

29 Winding Trl #29, Middlebury, CT 06762

$515 HOA • 2 garage spots • Pool

34 Breakneck Hill Rd, Middlebury, CT 06762
34 Breakneck Hill Rd, Middlebury, CT 06762
34 Breakneck Hill Rd, Middlebury, CT 06762
ABOUT THIS HOME
Middlebury, CT Homes for Sale
Come view this beautiful bright and spacious Colonial located on an interior lot in Middlebury, CT! Home features 5 bedrooms with 3 full bathrooms. Features include a spacious Great room with over 800 sq feet of space, which is perfect to host any special occasion. The heart of this home, the eat-in kitchen which connects to Great room and Dining room, comes with wine cooler, granite countertops and stainless-steel appliances. Home features good sized Formal Dining room with crown molding perfect for holiday gatherings. Also, on the main level comes a formal living when you walk in from the main entrance. Main floor also features good sized bedroom with good closet space. Upstairs features

$799,900

5 beds3 baths4,551 sq ft

34 Breakneck Hill Rd, Middlebury, CT 06762

1.56 acre lot • 3 garage spots • Car-dependent

Property at 835 Whittemore Rd, Middlebury, CT 06762, 4 beds, 3.5 baths

$499,900

4 beds3.5 baths3,016 sq ft

835 Whittemore Rd, Middlebury, CT 06762

Property at 460 Lake Shore Dr, Middlebury, CT 06762, 3 beds, 2 baths

$434,900

3 beds2 baths1,288 sq ft

460 Lake Shore Dr, Middlebury, CT 06762

Property at 180 Ridgewood Dr #219, Middlebury, CT 06762, 3 beds, 2.5 baths

$590,000

3 beds2.5 baths1,882 sq ft

180 Ridgewood Dr #219, Middlebury, CT 06762

Property at 28 Maple Dr, Middlebury, CT 06762, 3 beds, 3.5 baths

$525,000

3 beds3.5 baths1,596 sq ft

28 Maple Dr, Middlebury, CT 06762

Property at 405 Chestnut Cir #77, Middlebury, CT 06762, 2 beds, 3 baths

$649,500

2 beds3 baths2,292 sq ft

405 Chestnut Cir #77, Middlebury, CT 06762

Property at 106 Judd Hill Rd, Middlebury, CT 06762, 4 beds, 3.5 baths

$1,249,900

4 beds3.5 baths4,696 sq ft

106 Judd Hill Rd, Middlebury, CT 06762

Property at 39 Ridgewood Dr #39, Middlebury, CT 06762, 3 beds, 2.5 baths

$560,000

3 beds2.5 baths2,122 sq ft

39 Ridgewood Dr #39, Middlebury, CT 06762

Property at White Birch Ln, Middlebury, CT 06762, 4 beds, 3.5 baths

$1,299,895

4 beds3.5 baths4,100 sq ft

White Birch Ln, Middlebury, CT 06762

$867,750

4 beds3.5 baths3,175 sq ft

9 White Birch Ln, Middlebury, CT 06762

Property at 10 White Birch Ln, Middlebury, CT 06762, 3 beds, 2.5 baths

$796,750

3 beds2.5 baths2,700 sq ft

10 White Birch Ln, Middlebury, CT 06762

Property at Lot 5 White Birch Ln, Middlebury, CT 06762, 4 beds, 3.5 baths

$787,500

4 beds3.5 baths2,750 sq ft

Lot 5 White Birch Ln, Middlebury, CT 06762

Property at 9 White Birch Dr, Middlebury, CT 06762, 4 beds, 3 baths

$879,750

4 beds3 baths2,750 sq ft

9 White Birch Dr, Middlebury, CT 06762

Property at N Benson Rd #36, Middlebury, CT 06762, 3 beds, 2.5 baths

$499,900

3 beds2.5 baths1,950 sq ft

N Benson Rd #36, Middlebury, CT 06762

Property at 11 Hunting Ridge Rd, Middlebury, CT 06762, 4 beds, 2.5 baths

$799,900

4 beds2.5 baths2,700 sq ft

11 Hunting Ridge Rd, Middlebury, CT 06762

Property at 66 Artillery Rd, Middlebury, CT 06762, 4 beds, 3.5 baths

$649,000

4 beds3.5 baths2,691 sq ft

66 Artillery Rd, Middlebury, CT 06762

Property at 6 Brookside Dr #6, Middlebury, CT 06762, 3 beds, 2.5 baths

$719,000

3 beds2.5 baths3,745 sq ft

6 Brookside Dr #6, Middlebury, CT 06762

Property at 17 Deer Run Rd, Middlebury, CT 06762, 4 beds, 2.5 baths

$779,900

4 beds2.5 baths2,466 sq ft

17 Deer Run Rd, Middlebury, CT 06762

Property at 2 Deer Run Rd, Middlebury, CT 06762, 3 beds, 2.5 baths

$729,900

3 beds2.5 baths2,190 sq ft

2 Deer Run Rd, Middlebury, CT 06762

Property at 28 Hunting Ridge Rd, Middlebury, CT 06762, 4 beds, 2.5 baths

$779,900

4 beds2.5 baths2,466 sq ft

28 Hunting Ridge Rd, Middlebury, CT 06762

Property at 22 Somerset Dr, Middlebury, CT 06762, 3 beds, 2.5 baths

$899,000

3 beds2.5 baths2,878 sq ft

22 Somerset Dr, Middlebury, CT 06762

Property at 593 Park RD EXT, Middlebury, CT 06762, 4 beds, 3.5 baths

$995,000

4 beds3.5 baths4,496 sq ft

593 Park RD EXT, Middlebury, CT 06762

Property at 294 Christian Rd, Middlebury, CT 06762, 3 beds, 2.5 baths

$899,000

3 beds2.5 baths2,878 sq ft

294 Christian Rd, Middlebury, CT 06762

Property at 19 Deer Run Rd, Middlebury, CT 06762

$250,000

— beds— baths— sq ft

19 Deer Run Rd, Middlebury, CT 06762

Property at Lake Shore Dr, Middlebury, CT 06762

$69,000

— beds— baths— sq ft

Lake Shore Dr, Middlebury, CT 06762

Property at 288 Watertown Rd Lot 5, Middlebury, CT 06762

$200,000

— beds— baths2,376 sq ft

288 Watertown Rd Lot 5, Middlebury, CT 06762

Property at 288 Watertown Rd Lot 2, Middlebury, CT 06762

$269,900

— beds— baths2,376 sq ft

288 Watertown Rd Lot 2, Middlebury, CT 06762

Property at 75 GLENEAGLE Rd, Middlebury, CT 06762

$199,009

— beds— baths— sq ft

75 GLENEAGLE Rd, Middlebury, CT 06762

Property at 14 Deer Run Rd, Middlebury, CT 06762

$199,900

— beds— baths— sq ft

14 Deer Run Rd, Middlebury, CT 06762

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Average home prices near Middlebury, CT

Cities

Zip Codes
Minor Civil Divisions

Middlebury, CT real estate trends

$555K

Sale price

+19.4%
since last year

$165

Sale $/sq ft

-20.3%
since last year

Under list price

0.3%

Days on market

102

Down payment

—

Total homes sold

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