Vintage homes for sale & real estate in Middlebury, CT

12 homes

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ABOUT THIS HOME
Vintage Home for sale in Middlebury, CT:
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 appr

$485,000

3 beds2 baths1,740 sq ft

314 Porter Ave, Middlebury, CT 06762

Original hardwood • Black stone • Bay window

ABOUT THIS HOME
Vintage Home for sale in Middlebury, CT:
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 histo

$499,900

4 beds2.5 baths1,911 sq ft

802 Charcoal Ave, Middlebury, CT 06762

Original features • Over 2 acres • Workshop

ABOUT THIS HOME
Vintage Home for sale in Middlebury, CT:
Exceptional 1855 Greek Revival set in a prestigious Middlebury neighborhood, surrounded by the natural beauty of Flanders Preserve and Middlebury Land Trust land. This 5-bedroom, 31/2-bath architectural stunner is sited on 3.21 beautifully landscaped acres with mature trees, stone walls, perennial gardens and rolling open lawn, offering privacy and a feeling of escape and tranquility. The home includes wide-board floors, three fireplaces and a remarkable series of covered porches and "piazzas" capturing the romance of 19th-century country living. There is effortless flow from the gorgeous sunroom, with walls of windows, into the formal living room, dining room and large entertaini

$899,000

5 beds3.5 baths4,114 sq ft

552 Breakneck Hill Rd, Middlebury, CT 06762

Landscaped acres • Perennial gardens • Rolling open lawn

ABOUT THIS HOME
Vintage Home for sale in Middlebury, CT:
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

$350,000

3 beds2 baths1,466 sq ft

138 Steinmann Ave, Middlebury, CT 06762

Walk-in closet • Covered patio • Stone fireplace

ABOUT THIS HOME
Vintage Home for sale in Middlebury, CT:
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

$725,000

5 beds3 baths3,728 sq ft

783 Whittemore Rd, Middlebury, CT 06762

Solid wood cabinetry • Multi-vehicle garage • Personal workshop

Property at 77 Crest Rd, Middlebury, CT 06762, 4 beds, 3.5 baths

$749,900

4 beds3.5 baths2,674 sq ft

77 Crest Rd, Middlebury, CT 06762

Property at 700 Watertown Rd, Middlebury, CT 06762, 4 beds, 3 baths

$590,000

4 beds3 baths2,528 sq ft

700 Watertown Rd, Middlebury, CT 06762

Property at 10 Old Waterbury Rd, Middlebury, CT 06762, 5 beds, 4 baths

$699,900

5 beds4 baths2,345 sq ft

10 Old Waterbury Rd, Middlebury, CT 06762

Property at 327 Steinmann Ave, Middlebury, CT 06762, 2 beds, 1 bath

$280,000

2 beds1 bath676 sq ft

327 Steinmann Ave, Middlebury, CT 06762

Property at 326 Lake Shore Dr, Middlebury, CT 06762, 3 beds, 2 baths

$520,000

3 beds2 baths1,568 sq ft

326 Lake Shore Dr, Middlebury, CT 06762

Property at 47 Middlebury Ter, Middlebury, CT 06762, 2 beds, 1.5 baths

$474,500

2 beds1.5 baths1,953 sq ft

47 Middlebury Ter, Middlebury, CT 06762

Property at 775 South St, Middlebury, CT 06762, 8 beds, 7 baths

$2,850,000

8 beds7 baths9,619 sq ft

775 South St, Middlebury, CT 06762

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COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Middlebury, CT:
Immaculate ranch-style home with a fully remodeled kitchen completed in 2025, quartz countertops, and appliances updated in 2023! This beautifully maintained home features a welcoming living room and a versatile bonus great room for relaxing or entertaining. Finished basement space offers additional flexibility and potential for a second bedroom. Enjoy central air, radiant floor heat, and a cozy gas fireplace. A beautiful new Trex deck and outdoor gas fire pit provide an inviting setting for gatherings. A roof just five months old completes this lovely home! This home has previously operated comfortably as a 3 bedroom home, come in and see the flexibility for yourselves!! THIS ONE IS A MUS

$265,000

1 bed1 bath1,176 sq ft

59 Wayland Ave, Waterbury, CT 06708

Quartz countertops • Radiant floor heat • Remodeled kitchen

ABOUT THIS HOME
Vintage Home for sale in Middlebury, CT:
Welcome to 275 Davis Street, a well-cared-for 1945 two-story home in a convenient Oakville neighborhood. It has 5 rooms, 2 bedrooms and a full bath across 1,136 square feet. The interior mixes hardwood floors and wall-to-wall carpeting, and new Andersen windows throughout bring in plenty of natural light. The four-season sunroom is a favorite spot all year, whether for morning coffee, a home office or a quiet place to read. Outside, the newly painted exterior and a beautiful paver walkway give the home great curb appeal. Out back, an expansive deck is ready for grilling and entertaining, and the fenced side yard is perfect for pets. The large basement is ideal for a hobbyist, a workshop or

$309,900

2 beds1 bath1,136 sq ft

275 Davis St, Oakville, CT 06779

Fenced side yard • New andersen windows • Four-season sunroom

NEW 18 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Middlebury, CT:
Two-family opportunity in the Oakville section of Watertown! 35 Hubbell Avenue offers two apartments, each featuring two bedrooms and one full bathroom, for a total of four bedrooms and two full baths. The property offers flexibility for an owner-occupant seeking rental income or an investor adding to a portfolio. A covered front porch, rear patio and off-street driveway parking complement the property, while a full unfinished basement provides additional storage space. Explore the possibilities this two-family property has to offer. Agent/Owner.

$359,900

4 beds2 baths1,596 sq ft

35 Hubbell Ave, Watertown, CT 06779

Covered front porch • Rear patio • 7,405 sq ft lot

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Middlebury, CT:
Great Ranch well sited on level almost half acre yard, large living room with fireplace, kitchen and dining room overlooking back yard and deck, 2 bedrooms and 1 full bath, oversized back deck overlooking a small seasonal brook, private PHOTOS next week

$359,900

2 beds1 bath990 sq ft

555 Middle Road Tpke, Woodbury, CT 06798

Oversized back deck • 0.44 acre lot • Garage

OPEN SUN, 12PM TO 2PM

ABOUT THIS HOME
Vintage Home for sale in Middlebury, CT:
Discover the perfect blend of modern comfort, timeless charm, and peaceful living in this beautifully updated 3-bedroom, 1-bath ranch, ideally situated on a picturesque 3-acre property offering exceptional privacy, tranquility, and endless possibilities. Thoughtfully updated throughout, this truly move-in-ready home welcomes you with a warm and inviting living room featuring a cozy fireplace, perfect for relaxing evenings at home. The spacious, beautifully updated kitchen flows seamlessly into the dining area, creating an ideal setting for everyday living and entertaining. Three generously sized bedrooms and a tastefully updated full bathroom complete the main level, while the walk-out base

$424,900

3 beds1 bath1,224 sq ft

50 Hill Rd, Naugatuck, CT 06770

Walk-out basement • Updated kitchen • Cozy fireplace

ABOUT THIS HOME
Vintage Home for sale in Middlebury, CT:
Investment opportunity, 3 family fully occupied with long term tenants. Located within walking distance to downtown Naugatuck. First floor 2 apartments side by side one bedroom each, updated it kitchens, gas baseboard heat on both sides second floor with 3 bedrooms, newer kitchen, gas warm air heat. washer/dryer hook up on each apartment, new roof to be installed, 2 car garage paved parking. Owner related to agent.

$419,975

5 beds3 baths2,271 sq ft

21 Aetna St, Naugatuck, CT 06770

Paved parking • Updated kitchens • New roof

Property at 102 Brookside Ave, Naugatuck, CT 06770, 3 beds, 1 bath

$299,900

3 beds1 bath959 sq ft

102 Brookside Ave, Naugatuck, CT 06770

Property at 54 Quinn St, Naugatuck, CT 06770, 3 beds, 1.5 baths

$324,000

3 beds1.5 baths1,190 sq ft

54 Quinn St, Naugatuck, CT 06770

Property at 25 Bunker Hill Ave, Waterbury, CT 06708, 6 beds, 4 baths

$525,000

6 beds4 baths3,650 sq ft

25 Bunker Hill Ave, Waterbury, CT 06708

Property at 85 Aetna St #12, Naugatuck, CT 06770, 3 beds, 1 bath

$210,000

3 beds1 bath1,642 sq ft

85 Aetna St #12, Naugatuck, CT 06770

Property at 53 Elk Ave, Waterbury, CT 06708, 3 beds, 1.5 baths

$259,000

3 beds1.5 baths1,220 sq ft

53 Elk Ave, Waterbury, CT 06708

Property at 11 Media Ave, Waterbury, CT 06708, 3 beds, 1.5 baths

$299,900

3 beds1.5 baths1,290 sq ft

11 Media Ave, Waterbury, CT 06708

Property at 117 Arden Rd, Waterbury, CT 06708, 2 beds, 1 bath

$318,000

2 beds1 bath1,376 sq ft

117 Arden Rd, Waterbury, CT 06708

Property at 100 Irvington Ave, Waterbury, CT 06708, 3 beds, 2.5 baths

$395,000

3 beds2.5 baths2,847 sq ft

100 Irvington Ave, Waterbury, CT 06708

Property at 1217 Main St N, Woodbury, CT 06798, 3 beds, 1.5 baths

$699,900

3 beds1.5 baths1,960 sq ft

1217 Main St N, Woodbury, CT 06798

Property at 34 Corona Dr, Waterbury, CT 06708, 4 beds, 2 baths

$309,900

4 beds2 baths1,170 sq ft

34 Corona Dr, Waterbury, CT 06708

Property at 60 Venice Ave, Waterbury, CT 06708, 3 beds, 3 baths

$409,000

3 beds3 baths1,820 sq ft

60 Venice Ave, Waterbury, CT 06708

Property at 516 Chipman St, Waterbury, CT 06708, 3 beds, 1 bath

$349,000

3 beds1 bath1,428 sq ft

516 Chipman St, Waterbury, CT 06708

Property at 248 Hillside Ave, Naugatuck, CT 06770, 7 beds, 3 baths

$759,000

7 beds3 baths4,575 sq ft

248 Hillside Ave, Naugatuck, CT 06770

Property at 21 Pond St, Naugatuck, CT 06770, 4 beds, 2.5 baths

$335,000

4 beds2.5 baths2,285 sq ft

21 Pond St, Naugatuck, CT 06770

Vintage Homes for Sale in Middlebury

There are currently 12 vintage homes for sale in Middlebury at a median listing price of $583K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Middlebury stay on the market for 62 days. This map is refreshed with the newest listings in Middlebury every 15 minutes.

In the past month, 13 homes have been sold in Middlebury. In addition to houses in Middlebury, there were also 8 condos, 0 townhouses, and 1 multi-family unit for sale in Middlebury last month. Find your dream home in Middlebury using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Middlebury are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Middlebury. If you're looking to sell your home in the Middlebury area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Middlebury with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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