Is a car needed in Middlebury, VT?

As of early 2026, 89% of users say car is needed

Would people walk alone at night in Middlebury, VT?

As of early 2026, 76% of users say people would walk alone at night

Are yards well-kept in Middlebury, VT?

As of early 2026, 72% of users say yards are well-kept

Is Middlebury, VT dog-friendly?

As of early 2026, 71% of users say it's dog friendly

Is there wildlife in Middlebury, VT?

As of early 2026, 64% of users say there's wildlife

Is parking easy in Middlebury, VT?

As of early 2026, 61% of users say parking is easy

Is Middlebury, VT walkable to restaurants?

As of early 2026, 60% of users say it's walkable to restaurants

Does Middlebury, VT show holiday spirit?

As of early 2026, 59% of users say there's holiday spirit

Are neighbors friendly in Middlebury, VT?

As of early 2026, 54% of users say neighbors are friendly

Is Middlebury, VT quiet?

As of early 2026, 52% of users say it's quiet

Is Middlebury, VT walkable to grocery stores?

As of early 2026, 50% of users say it's walkable to grocery stores

Do residents of Middlebury, VT plan to stay at least 5 years?

As of early 2026, 50% of users say they plan to stay for at least 5 years

Does Middlebury, VT have sidewalks?

As of early 2026, 48% of users say there are sidewalks

Are there community events in Middlebury, VT?

As of early 2026, 45% of users say there are community events

Do kids play outside in Middlebury, VT?

As of early 2026, 39% of users say kids play outside

Are the streets well-lit in Middlebury, VT?

As of early 2026, 27% of users say streets are well-lit

ACCEPTING BACKUPS

1.82 ACRES

Listed by Beth Stanway, IPJ Real Estate, (802) 989-9928

464 East Main Street
Middlebury, VT 05753

4 Beds
3.5 Baths
2,922 sqft (on 1.82 acres)

$699,000

4 Beds

3.5 Baths

2,922 sqft

(on 1.82 acres)

Local Information

Map ViewExplore the area around 464 East Main Street.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Last check for updates: 1 day ago

Listing courtesy of Beth Stanway

IPJ Real Estate, Cell: 802-989-9928

Source: PrimeMLS, MLS#5095929

Also Listed on PrimeMLS.

Description

Nestled along the scenic banks of the Middlebury River, this beautifully updated vintage home offers a rare combination of historic character, modern comfort, and versatile living space. The main residence features three bedrooms plus a dedicated office, providing flexibility for remote work, guests, or hobbies. Enjoy peaceful mornings and relaxing evenings in the screened porch overlooking the property's lush gardens and natural surroundings. Thoughtful updates throughout preserve the home's timeless charm while enhancing everyday convenience. Upstairs there is a claw foot tub overlooking the beautiful yard, soak and listen to the river! A spacious barn adds exceptional storage, workshop, or hobby space, while the separate one-bedroom apartment presents opportunities for rental income, multigenerational living, or private guest accommodations. Surrounded by established gardens and the soothing sounds of the river, this special property offers a quintessential Vermont lifestyle with room to live, work, and entertain. As an added bonus, this property owns the land across the street ensuring a permanent buffer! Whether you're seeking a full-time residence, country retreat, or property with income potential, this riverside gem is a unique opportunity not to be missed.

Home Highlights

Parking

Garage

Outdoor

Porch

A/C

Heating only

HOA

None

Price/Sqft

$239

Listed

21 days ago

Home Details for 464 East Main Street

Active Status
MLS Status: Active Under Contract

Interior Features
Interior Details Basement: Bulkhead,Unfinished,Interior EntryNumber of Rooms: 8
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 1Number of Bathrooms (three quarters): 2Number of Bathrooms (half): 1
Dimensions and Layout Living Area: 2922 Square Feet
Appliances & Utilities Utilities: Cable, Gas On-SiteAppliances: Dishwasher, Dryer, Microwave, Gas Range, Refrigerator, WasherDishwasherDryerLaundry: 2nd Floor LaundryMicrowaveRefrigeratorWasher
Heating & Cooling Heating: Natural Gas,Hot Air,Wood StoveNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Natural Gas
Gas & Electric Electric: Circuit Breakers
Windows, Doors, Floors & Walls Flooring: Softwood
Levels, Entrance, & Accessibility Stories: 2Levels: TwoFloors: Softwood
View No View
Security Security: Smoke Detector(s)

Exterior Features
Exterior Home Features Roof: Asphalt Shingle SlatePatio / Porch: Porch, Screened PorchOther Structures: Barn(s)Exterior: Garden, Natural ShadeFoundation: StoneGarden
Parking & Garage Number of Garage Spaces: 1Number of Covered Spaces: 1Has a GarageParking Spaces: 1Parking: Gravel
Frontage WaterfrontWaterfront: River, River FrontResponsible for Road Maintenance: Public Maintained RoadOn Waterfront
Water & Sewer Sewer: Septic TankWater Body: Middlebury River
Farm & Range Frontage Length: Road frontage: 150
Finished Area Finished Area (above surface): 2922 Square Feet

Days on Market
Days on Market: 21

Property Information
Year Built Year Built: 1840
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Historic Vintage
Building Construction Materials: Clapboard ExteriorNot a New Construction

Price & Status
Price List Price: $699,000Price Per Sqft: $239

Location
Direction & Address City: Middlebury
School Information Elementary School: Mary Hogan SchoolElementary School District: Addison CentralJr High / Middle School: Middlebury Union Middle #3Jr High / Middle School District: Addison CentralHigh School: Middlebury Senior UHSD #3High School District: Addison Central

Agent Information
Listing Agent Listing ID: 5095929

Building
Building Area Building Area: 4424 Square Feet

Lot Information
Lot Area: 1.82 Acres

Miscellaneous
BasementMls Number: 5095929Zillow Contingency Status: Accepting Back-up OffersAttribution Contact: Cell: 802-989-9928Above Grade Unfinished Area: 2922Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 952Below Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

Market trends in Middlebury

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Price History for 464 East Main Street

Date	Price	Event	Source
06/21/2026	$699,000	Listed For Sale	PrimeMLS #5095929

02/25/2000	$160,000	Sold	N/A
Recording Date 02/25/2000 Contract Date 02/25/2000 County Transfer Tax N/A Total Transfer Tax $1,250

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Property Tax and Assessment

Year	2024
Tax
Assessment	$244,200

Home facts updated by county records

Comparable Sales for 464 East Main Street

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
427 E Main Street, Middlebury, VT	0.33	Single-Family Home	$432,000	12/23/25	5	2	2,963
44 Lower Plains Road, Middlebury, VT	0.57	Single-Family Home	$372,500	03/20/26	6	3	2,415
418 East Main Street, Middlebury, VT	0.40	Single-Family Home	$516,000	08/22/25	3	2	1,780
37 School House Hill Road, Middlebury, VT	0.64	Single-Family Home	$460,000	08/12/25	4	2	1,500
42 Lower Plains Road, Middlebury, VT	0.54	Single-Family Home	$320,000	02/25/26	4	2.5	1,875
82 Ossie Road, Middlebury, VT	0.73	Single-Family Home	$280,000	03/18/26	3	1.5	1,330
86 Ossie Road, Middlebury, VT	0.71	Single-Family Home	$410,000	02/11/26	3	2	1,673
45 Ossie Road, Middlebury, VT	0.97	Single-Family Home	$413,000	08/08/25	3	2	2,185
46 Ossie Road, Middlebury, VT	0.94	Single-Family Home	$408,000	03/26/26	3	2.5	1,694

Nearby homes

Get a sense of prices in the area by checking nearby homes.

Skip to last item

FOR SALE
0.6 ACRES
$699,000
4 bd
2 ba
2,684 sqft
466 East Main Street,
Middlebury, VT 05753
PrimeMLS, Active
FOR SALE
0.26 ACRES
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4 bd
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442 East Main Street,
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OFF MARKET
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3 bd
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436 East Main Street,
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OFF MARKET
Est. $369,000
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25 Lower Plains Road,
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Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 464 East Main Street.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Middlebury

At least 17 Trulia users voted on each feature.

89 % Say car is needed
76 % Say people would walk alone at night
72 % Say yards are well-kept
71 % Say it's dog friendly
64 % Say there's wildlife
61 % Say parking is easy
60 % Say it's walkable to restaurants
59 % Say there's holiday spirit
54 % Say neighbors are friendly
52 % Say it's quiet
50 % Say it's walkable to grocery stores
50 % Say they plan to stay for at least 5 years
48 % Say there are sidewalks
45 % Say there are community events
39 % Say kids play outside
27 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.

Jaimelshelfon
Resident
2y ago
"Great school district College town but not a party school Historically charm meets modern style and interests Easy and convenient public transportation for after school activities "
1
Flag
Drobinson
Resident
7y ago
"I’ve lived in this neighborhood for almost 30 years. Neighbors are friendly, but also respect privacy. Wooded area, but close to town center. "
2
Flag

LGBTQ Local Legal Protections

Beth Stanway, IPJ Real Estate, Cell: 802-989-9928

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 2026-07-12 09:10:27 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.

464 East Main Street, Middlebury, VT 05753 is a 4 bedroom, 4 bathroom, 2,922 sqft single-family home built in 1840. This property is currently available for sale and was listed by PrimeMLS on Jun 21, 2026. The MLS # for this home is MLS# 5095929.

464 East Main Street
Middlebury, VT 05753

$699,000

$699,000

Local Information