Middlebury, VT homes for sale & real estate

19 homes

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NEW 11 HRS AGO

45 Ossie Rd, Middlebury, VT 05753
45 Ossie Rd, Middlebury, VT 05753
45 Ossie Rd, Middlebury, VT 05753
ABOUT THIS HOME
Middlebury, VT Homes for Sale
Lovely ranch home on over half an acre in East Middlebury. This three bedroom two bath home has everything you need on one level. Large Primary bedroom with attached bath, sunny kitchen that looks out to the back yard. A very large mud room off the two car garage - with a murphy bed for summer overflow sleeping! Dining area with built ins. A large living room with fireplace and built in book shelves. A sweet sunroom for extra living space. There are two more bedrooms on the main level, a 3/4 bath and an amazing greenhouse with heat and water. Newer windows take another worry away! Heat pumps make this cool in the summer and warm in the shoulder months. Speaking of cool. .. there is an amazi

$389,000

3 beds2 baths2,185 sq ft

45 Ossie Rd, Middlebury, VT 05753

0.55 acre lot • 2 garage spots • Pool

53 High St, Middlebury, VT 05753
53 High St, Middlebury, VT 05753
53 High St, Middlebury, VT 05753
ABOUT THIS HOME
Middlebury, VT Homes for Sale
Great views and lots of opportunity await! What was once a barn in the early 1900's is now 2 apartments. This property could be converted back to a singe family or remain as is for multi-generational living. It could also be used as a rental or think big and start over and build your dream home. Inside you will find 2 one bedroom apartments and stairs to the top floor which needs renovation. Wonderful views and sunsets from all 3 floors looking West over Middlebury proper and the Adirondacks, for spectacular sunsets! A short distance to groceries and the Co-op and Chipman Hill Park is a few hundred feet away! Lots of beautiful trees were planted above the house by the current owners includ

$350,000

3 beds3 baths1,740 sq ft

53 High St, Middlebury, VT 05753

0.29 acre lot • Somewhat walkable

3D WALKTHROUGH

427 E Main St, Middlebury, VT 05753
427 E Main St, Middlebury, VT 05753
427 E Main St, Middlebury, VT 05753
ABOUT THIS HOME
Middlebury, VT Homes for Sale
Situated in the heart of East Middlebury, this farmhouse built in 1800 offers nearly 3,000 square feet of living space and features five bedrooms on a spacious 0.53-acre corner lot. The sizeable kitchen, with woodstove and attached breakfast nook, provides ample space for entertaining or simply whipping up meals. Adjacent to the kitchen, a newly remodeled utility room and bath with a tiled walk-in steam shower add both functionality and modern convenience. The first floor also includes a formal dining room, a substantial living area, and a family room with a wood burning fireplace, perfect for hosting those milestone events. The traditional large front door leads to an expansive wrap-around

$559,500

5 beds2 baths2,963 sq ft

427 E Main St, Middlebury, VT 05753

0.53 acre lot • 2 garage spots • Car-dependent

3D WALKTHROUGH

24 Oak Dr, Middlebury, VT 05753
24 Oak Dr, Middlebury, VT 05753
24 Oak Dr, Middlebury, VT 05753
ABOUT THIS HOME
Middlebury, VT Homes for Sale
Move in ready saltbox on a corner lot in the wonderful Woodlands neighborhood. This well maintained three bedroom home sits on 1.24 private acres with a mix of open yard and woods. The main level has hardwood floors, an oversized living room/dining room, a den, an updated kitchen, 3/4 bath and an amazing four season sunroom. The kitchen - recently renovated - has plenty of cabinet space and updated appliances. The attached two car garage opens into a mudroom with laundry. Upstairs there are three bedrooms, and an updated bath. Both baths were renovated in 2018. The basement is finished with ample storage and different spaces for home office, gym, media room, etc. .. There are heat pump/spli

$689,000

3 beds2 baths2,796 sq ft

24 Oak Dr, Middlebury, VT 05753

1.24 acre lot • 2 garage spots • Car-dependent

3D WALKTHROUGH

44-48 Merchants Row, Middlebury, VT 05753
44-48 Merchants Row, Middlebury, VT 05753
44-48 Merchants Row, Middlebury, VT 05753
ABOUT THIS HOME
Middlebury, VT Homes for Sale
A versatile residential and commercial property right in downtown Middlebury with great views of both the town green and river for someone who wants convenient downtown living and working, while earning income from additional apartments and small businesses! The owners did major renovations on the entire building including all new wiring, plumbing, new natural gas heating system, new roof, and flooring. The main level of the building works great as a commercial/office space, and includes a full kitchen, 2-3 offices, 3/4 bath and large gathering room. The second and third floors have been turned into a lovely 2-4 bedroom residential apartment. Hardwood floors fill the living and kitchen area

$1,350,000

4 beds4 baths4,716 sq ft

44-48 Merchants Row, Middlebury, VT 05753

3,484 sq ft lot • Very walkable

Property at 719 Washington Street Ext, Middlebury, VT 05753, 4 beds, 3 baths

$679,000

4 beds3 baths2,930 sq ft

719 Washington Street Ext, Middlebury, VT 05753

Property at 394 Cider Mill Rd, Cornwall, VT 05753, 3 beds, 2 baths

$799,000

3 beds2 baths1,944 sq ft

394 Cider Mill Rd, Cornwall, VT 05753

Property at 1515 Cider Mill Rd, Cornwall, VT 05753, 5 beds, 6 baths

$5,995,000

5 beds6 baths10,943 sq ft

1515 Cider Mill Rd, Cornwall, VT 05753

Property at 915 Lower Foote St, Middlebury, VT 05753, 3 beds, 1.5 baths

$449,900

3 beds1.5 baths1,584 sq ft

915 Lower Foote St, Middlebury, VT 05753

Property at 1 East Rd, Middlebury, VT 05753, 3 beds, 2 baths

$614,000

3 beds2 baths1,976 sq ft

1 East Rd, Middlebury, VT 05753

Property at 91 Old Pasture Ln, Middlebury, VT 05753, 6 beds, 5 baths

$1,355,000

6 beds5 baths4,503 sq ft

91 Old Pasture Ln, Middlebury, VT 05753

Property at 1465 West St, Cornwall, VT 05753, 4 beds, 3.5 baths

$599,900

4 beds3.5 baths3,750 sq ft

1465 West St, Cornwall, VT 05753

Property at 436 A Middle Rd, Middlebury, VT 05753, 3 beds, 1 bath

$375,000

3 beds1 bath2,442 sq ft

436 A Middle Rd, Middlebury, VT 05753

Property at 60-62 Main St, Middlebury, VT 05753, 1 bed, 3 baths

$599,000

1 bed3 baths4,506 sq ft

60-62 Main St, Middlebury, VT 05753

Property at 103 Court St, Middlebury, VT 05753, 5 beds, 3.5 baths

$798,000

5 beds3.5 baths4,810 sq ft

103 Court St, Middlebury, VT 05753

Property at 4 Wilmar St #7, Middlebury, VT 05740

$150,000

— beds— baths— sq ft

4 Wilmar St #7, Middlebury, VT 05740

Property at 2 Wilmar St #8, Middlebury, VT 05740

$150,000

— beds— baths— sq ft

2 Wilmar St #8, Middlebury, VT 05740

Property at TBD Bardon Dr, Cornwall, VT 05753

$175,000

— beds— baths— sq ft

TBD Bardon Dr, Cornwall, VT 05753

Property at TBD West St, Cornwall, VT 05753

$499,999

— beds— baths— sq ft

TBD West St, Cornwall, VT 05753

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Nearby homes that match your criteria

NEW 19 HRS AGO3D WALKTHROUGH

808 Peddlers Bridge Rd, Ripton, VT 05766
808 Peddlers Bridge Rd, Ripton, VT 05766
808 Peddlers Bridge Rd, Ripton, VT 05766
ABOUT THIS HOME
Middlebury, VT Homes for Sale
Mountain views great you as you drive up to this well maintained home. Located on 14 acres, with plenty of open land for gardens and play, with woods to explore and trails for walking, skiing or snowshoeing! Recent upgrades include a standing seam roof, all new siding, a stand by generator and mini splits for air conditioning. The house has a great floor plan, with the kitchen open to the living room and dining areas, with exposed beams and a double sided fireplace to delineate the spaces. The eat in kitchen has an island for extra counter space/storage/seating with a butcher block top, granite countertops and stainless steel appliances. A wood stove faces the kitchen for cozy winter days!

$795,000

3 beds2 baths2,922 sq ft

808 Peddlers Bridge Rd, Ripton, VT 05766

14 acre lot • Garage • Car-dependent

2459 US Route 7, Leicester, VT 05733
2459 US Route 7, Leicester, VT 05733
2459 US Route 7, Leicester, VT 05733
ABOUT THIS HOME
Middlebury, VT Homes for Sale
Welcome to 2459 US Route 7 in Leicester, VT—an updated and well-cared-for home on a half-acre lot with a spacious detached two-car garage and extended workshop space. Just minutes from beautiful Lake Dunmore, Middlebury, and Brandon, this property offers a convenient location and a comfortable layout. Inside, you'll find two bedrooms plus a bonus room, with brand new vinyl flooring in all three. The entire interior has been freshly painted, and the kitchen is filled with natural light thanks to overhead skylights. The primary bedroom features a spacious walk-in closet and ensuite bath, while the bonus room offers flexible space for a home office, guest area, or hobby room. Central air

$300,000

2 beds2 baths1,796 sq ft

2459 US Route 7, Leicester, VT 05733

0.5 acre lot • 2 garage spots • Car-dependent

1511 W Hill Rd, Lincoln, VT 05443
1511 W Hill Rd, Lincoln, VT 05443
1511 W Hill Rd, Lincoln, VT 05443
ABOUT THIS HOME
Middlebury, VT Homes for Sale
Perched on 11.18 peaceful acres, this 3-bedroom home offers a seamless blend of natural beauty, comfort, and flexible living space - perfect for every season! Stunning views of Mt. Abraham, Mt. Grant, Bread Loaf Mountain, and the Long Trail are just some of the many highlights. Whether you’re savoring golden sunrises, alpenglow sunsets, or stargazing beside the fire pit, this property invites you to slow down and enjoy life’s quieter moments. A large great room with a floor-to-ceiling stone fireplace and wood stove welcomes you as you step inside. The main floor offers one-level living and includes a primary bedroom suite with its own balcony - perfect for enjoying morning coffe

$799,000

3 beds2.5 baths3,137 sq ft

1511 W Hill Rd, Lincoln, VT 05443

11.18 acre lot • 3 garage spots • Car-dependent

1 Moosalamoo Club Rd, Salisbury, VT 05769
1 Moosalamoo Club Rd, Salisbury, VT 05769
1 Moosalamoo Club Rd, Salisbury, VT 05769
ABOUT THIS HOME
Middlebury, VT Homes for Sale
A charming retreat combines rustic charm with modern amenities, providing the perfect setting for relaxation and outdoor adventures. Situated within the Moosalamoo Club on Lake Dunmore, this cottage offers a unique opportunity to experience the beauty of Vermont's natural landscape. Lake Dunmore, one of Vermont's most sought-after destinations, and the surrounding area offers residents and guests a variety of activities such as fishing, swimming, boating, skating, cross-country skiing, hiking and showshoeing. A single level, spacious and open living area, nicely renovated to more comfortably enjoy your stay at the lake. The cottage's outdoor space is a true highlight, offering a flat yard w

$425,000

2 beds1 bath738 sq ft

1 Moosalamoo Club Rd, Salisbury, VT 05769

1.67 acre lot • $250 HOA • Car-dependent

396 W Shore Rd, Salisbury, VT 05769
396 W Shore Rd, Salisbury, VT 05769
396 W Shore Rd, Salisbury, VT 05769
ABOUT THIS HOME
Middlebury, VT Homes for Sale
Your Perfect Summer Getaway on Lake Dunmore. This charming seasonal cottage at Sunset Hill offers stunning views of Lake Dunmore & the Moosalamoo Range—an ideal setting for your summer escape. Fully furnished & move-in ready, the 444 sq. ft. camp features 2 bedrooms, a remodeled kitchen with newer appliances, & an open living/dining area with vaulted ceilings. It’s equipped with a propane stove to keep you comfortable well into the cooler fall months. A screened porch offers the perfect space to relax & enjoy your lake views. As part of the Sunset Hill Association, the property includes shared maintenance services—such as lawn care & seasonal w

$195,000

2 beds1 bath444 sq ft

396 W Shore Rd, Salisbury, VT 05769

$183 HOA • Car-dependent

404 W Shore Rd #5, Salisbury, VT 05769
404 W Shore Rd #5, Salisbury, VT 05769
404 W Shore Rd #5, Salisbury, VT 05769
ABOUT THIS HOME
Middlebury, VT Homes for Sale
SWEET LAKE DUNMORE COTTAGE! Just in time for summer on Dunmore, one of Vermont's most beautiful lakes. Cute and affordable two-bedroom seasonal cottage is part of the Sunset Hill Condo Association which includes the use of a private lakefront that showcases the striking views of Mt Moosalamoo and Dunmore. Boat dockage is negotiable. Cottage has been renovated from the studs out with replacement windows, new walls, ceiling fan, updated electrical, vaulted knotty pine ceilings, and loft bedroom. Furnishings are included so just bring your bathing suit and a toothbrush! HOA includes water, electricity, trash pickup, and mowing plus common ownership of 33 acres. Cottage can be rented out anytim

$229,000

2 beds1 bath579 sq ft

404 W Shore Rd #5, Salisbury, VT 05769

33 acre lot • $125 HOA • Car-dependent

Property at 1495 Smead Rd, Salisbury, VT 05769, 3 beds, 1 bath

$280,000

3 beds1 bath2,236 sq ft

1495 Smead Rd, Salisbury, VT 05769

Property at 55 Story Dr, Salisbury, VT 05769, 2 beds, 1 bath

$335,000

2 beds1 bath648 sq ft

55 Story Dr, Salisbury, VT 05769

Property at 909 East St, New Haven, VT 05472, 2 beds, 3.5 baths

$649,000

2 beds3.5 baths2,892 sq ft

909 East St, New Haven, VT 05472

Property at 1083 Lake Dunmore Rd, Salisbury, VT 05769, 4 beds, 3 baths

$469,000

4 beds3 baths— sq ft

1083 Lake Dunmore Rd, Salisbury, VT 05769

Property at 54 Forest Ridge Dr, Bristol, VT 05443, 4 beds, 3 baths

$595,000

4 beds3 baths3,864 sq ft

54 Forest Ridge Dr, Bristol, VT 05443

Property at 1233 Route 125, Ripton, VT 05766, 11 beds, 10.5 baths

$1,200,000

11 beds10.5 baths5,258 sq ft

1233 Route 125, Ripton, VT 05766

Property at 200B Burgess Rd, Shoreham, VT 05770, 3 beds, 2.5 baths

$2,485,000

3 beds2.5 baths2,800 sq ft

200B Burgess Rd, Shoreham, VT 05770

Property at 65 Jones Rd, Salisbury, VT 05769, 3 beds, 4 baths

$899,000

3 beds4 baths4,380 sq ft

65 Jones Rd, Salisbury, VT 05769

Property at 640 Orchard Dr, Bridport, VT 05734, 3 beds, 1.5 baths

$1,499,000

3 beds1.5 baths2,401 sq ft

640 Orchard Dr, Bridport, VT 05734

Property at 1041 Smead Rd Lot 1, Salisbury, VT 05769

$90,000

— beds— baths— sq ft

1041 Smead Rd Lot 1, Salisbury, VT 05769

Property at 0 VT Route 125, Bridport, VT 05734

$699,000

— beds— baths— sq ft

0 VT Route 125, Bridport, VT 05734

Property at 0 Upper Plains Rd, Salisbury, VT 05769

$299,000

— beds— baths— sq ft

0 Upper Plains Rd, Salisbury, VT 05769

Property at 0 N Pond Rd, Salisbury, VT 05769

$359,000

— beds— baths— sq ft

0 N Pond Rd, Salisbury, VT 05769

Property at 00 Harvey Rd #2, Bristol, VT 05443

$130,000

— beds— baths— sq ft

00 Harvey Rd #2, Bristol, VT 05443

Average home prices near Middlebury, VT

Cities

Zip Codes
Minor Civil Divisions

05753 homes for sale
$606,950

Middlebury, VT real estate trends

$453K

Sale price

$323

Sale $/sq ft

Over list price

0.2%

Days on market

Down payment

—

Total homes sold

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Copyright 2025 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Sat Jun 14 2025 on the search page

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