999 Happy Valley Road

Closed 8/31/21
Closed 8/31/21
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Last Sold Price
$445,000
3 beds2,459 sqft$181/sqft
999 Happy Valley Rd, Middlebury, VT 05753

Description

You've driven by it so many times. Haven't you wondered about what sits behind the privacy hedges? It's been 30 years since this house was last for sale and now is your chance to make a lasting imprint on this stately home. It all starts with good bones, you can turn the rest into exactly what you want. Move in and work on it as you go, or plan the renovation of your dreams! There is original trim, pocket doors, hardware and plenty of natural light filtering in through the large windows. Open all...You've driven by it so many times. Haven't you wondered about what sits behind the privacy hedges? It's been 30 years since this house was last for sale and now is your chance to make a lasting imprint on this stately home. It all starts with good bones, you can turn the rest into exactly what you want. Move in and work on it as you go, or plan the renovation of your dreams! There is original trim, pocket doors, hardware and plenty of natural light filtering in through the large windows. Open all the doors and you have a very open feeling home with a dining room, living room and front parlor. Upstairs are the bedrooms and a 1/2 bath and then the attic is prime for a bit of expansion space if you need more! There are views of Chipman Hill and the eastern slope of the Green Mountains towards Bristol. Take a quick drive and you're in Middlebury or a short walk to the entrance to the Trail Around Middlebury at the end of Ellen Drive - just down the road. A detached garage with extra storage, dog fence/dog house and a concrete pad for parking or basketball round out the outside. Town water and town sewer and a new boiler!
LISTING CLOSED: 08/31/2021 12:00 AM

  1. Listed by Amey Ryan • IPJ Real Estate

Sold By Greentree Real Estate

Property Details for 999 Happy Valley Road

Status
Closed
MLS #
4860683
Days on Market
18
Taxes
$7,633 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
Single Family
MLS Type
Residential / Single Family
Year Built
1900
Lot Size
1.21 AC / 52,707 SF
County
Addison County
Parking
Unpaved
Zoning
HDR

Recent comparable sales

Median sold price

$520,000

Avg days on market

24

Sale-to-list ratio

104.0%

Middlebury, VT

9 comparable properties found

$520,000 | 21 Short Shannon Street, Middlebury, VT 05753
1/30
1

$520,000

Sold 06/30/25

3
Bedrooms
2,152
Square Feet
0.23
Acres

21 Short Shannon Street, Middlebury, VT 05753

$345,500 | 800 Highway 7, Middlebury, VT 05753
1/47
2

$345,500

Sold 08/29/25

3
Bedrooms
2,300
Square Feet
1.7
Acres

800 Highway 7, Middlebury, VT 05753

$605,000 | 220 Painter Hills Road, Middlebury, VT 05753
1/50
3

$605,000

Sold 10/16/25

3
Bedrooms
2,480
Square Feet
1.5
Acres

220 Painter Hills Road, Middlebury, VT 05753

$520,000 | 47 Barnes Brk Road, Middlebury, VT 05753
1/10
4

$520,000

Sold 06/22/26

3
Bedrooms
2,019
Square Feet
Unavailable
Acres

47 Barnes Brk Road, Middlebury, VT 05753

$520,000 | 29 Barnes Brk Road, Unit 9 6, Middlebury, VT 05753
1/10
5

$520,000

Sold 06/16/26

3
Bedrooms
2,019
Square Feet
Unavailable
Acres

29 Barnes Brk Road, Unit 9 6, Middlebury, VT 05753

$520,000 | 30 Meadowlark Lane, Unit 7 6, Middlebury, VT 05753
1/6
6

$520,000

Sold 05/14/26

3
Bedrooms
2,019
Square Feet
Unavailable
Acres

30 Meadowlark Lane, Unit 7 6, Middlebury, VT 05753

$525,000 | 33 Stonecrop Road, Middlebury, VT 05753
1/10
7

$525,000

Sold 09/04/25

3
Bedrooms
2,019
Square Feet
Unavailable
Acres

33 Stonecrop Road, Middlebury, VT 05753

$490,000 | 104 Seymour Street, Middlebury, VT 05753
1/30
8

$490,000

Sold 03/05/25

3
Bedrooms
1,398
Square Feet
0.63
Acres

104 Seymour Street, Middlebury, VT 05753

$430,000 | 200 Butternut Ridge Drive, Middlebury, VT 05753
1/30
9

$430,000

Sold 02/12/26

3
Bedrooms
2,174
Square Feet
0.4
Acres

200 Butternut Ridge Drive, Middlebury, VT 05753

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Location

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Building Information for 999 Happy Valley Road

Stories2Year Built1900Building Size-Lot Size1.21 AC / 52,707 SF

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$2,898 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,262

Property Taxes

$636

HOA Dues

$0

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Property Information for 999 Happy Valley Road

Summary
Location and General Information
  • Area Description: Near Paths, Village
  • City: Middlebury
  • County: VT-Addison
  • Directions: From Middlebury turn east onto Washington Street (near the Middlebury Inn). At the 2nd Stop sign bear left onto Washington St Ext. Turn left onto Happy Valley Rd. Property is first driveway on the right.
  • Latitude: 44.028127143931407
  • Longitude: -73.147652186508182
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip: 05753
Taxes and HOA Information
  • SPAN Number: 387-120-12442
  • Tax - Gross Amount: $7,633.45
  • Tax Year: 2020
  • Taxes TBD: No
School Information
  • School - High: Middlebury Senior UHSD #3
  • School - District: Addison Central
  • School - Elementary: Mary Hogan School
  • School - Middle/Jr: Middlebury Union Middle #3
Parking
  • Garage: Yes
  • Garage Capacity: 1.00
  • Driveway: Gravel
Property
Lot Information
  • Footprint: 35 x 46
  • Lot - Sqft: 52708.0
  • Lot Size Acres: 1.21
  • Road Frontage Length: 630.0
  • Square Feet Apx Finished Above Grade: 2459.0
  • Square Feet Apx Finished AG Source: Public Records
  • Square Feet Apx Finished Below Grade: 0.0
  • Square Feet Apx Total: 4352.0
  • Square Feet Apx Total Finished: 2459.0
  • Square Feet Apx Unfinished Above Grade: 900.0
  • Square Feet Apx Unfinished AG Source: Estimated
  • Square Feet Apx Unfinished Below Grade: 993.0
  • Square Feet Apx Unfinished BG Source: Public Records
Property and Assessments
  • Assessment Amount: $314,200
  • Assessment Year: 2019
  • Property Class: Residential
  • Property Type: Single Family
  • Easements: No
  • Flood Zone: No
  • Foundation: Marble, Stone
  • PreConstruction: No
  • Resort: No
  • Surveyed: Unknown
  • Year Built: 1900
Utilities
  • Electric Company: Green Mountain Power
  • Cable Company: Comcast
  • Fuel Company: MacIntyre Services
  • Electric: Circuit Breaker(s)
  • Sewer: Public
  • Utilities: Phone, Cable, Internet - Cable
Interior and Exterior Features
Exterior Features
  • Color: Wht/Brick
  • Features - Accessibility: 1st Floor Full Bathroom, 1st Floor Hrd Surfce Flr
  • Features - Exterior: Barn, Fence - Dog, Natural Shade, Outbuilding, Porch - Covered, Shed, Storage
  • Roads: Gravel, Paved, Public
  • Roof: Shingle - Asphalt, Slate, Standing Seam
Interior Features
  • Appliances: Dishwasher, Refrigerator, Stove - Electric
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Bulkhead, Crawl Space, Full, Stairs - Exterior, Stairs - Interior, Unfinished, Interior Access, Exterior Access, Stairs - Basement
  • Baths - Total: 2
  • Baths - Full: 1
  • Half Baths: 1
  • One Quarter Baths: 0
  • Three Quarter Bath: 0
  • Rooms - Total: 10
  • Rooms: Level 1: Level 1: Bath - Full, Level 1: Dining Room, Level 1: Family Room, Level 1: Kitchen, Level 1: Living Room
  • Rooms: Level 2: Level 2: Bedroom, Level 2: Bath - 1/2, Level 2: Office/Study
  • Bedrooms - Total: 3
  • Equipment: Smoke Detector, Stove-Pellet
  • Features - Interior: Attic, Laundry Hook-ups, Lead/Stain Glass, Natural Light, Natural Woodwork, Laundry - Basement
  • Flooring: Hardwood, Softwood, Tile, Vinyl
  • Heat Fuel: Oil, Pellet
  • Heating: Radiator, Steam, Stove - Pellet
  • Cooling: None
  • Total Stories: 2
Room Information
Room 1
  • Room Dimensions: 14 X 12
  • Room Level: 1
  • Room Type: Kitchen
Room 2
  • Room Dimensions: 14 X 16
  • Room Level: 1
  • Room Type: Dining Room
Room 3
  • Room Dimensions: 15 X 18
  • Room Level: 1
  • Room Type: Family Room
Room 4
  • Room Dimensions: 14 X 16
  • Room Level: 1
  • Room Type: Living Room
Room 5
  • Room Dimensions: 13 X 14
  • Room Level: 2
  • Room Type: Bedroom
Room 6
  • Room Dimensions: 14 X 13
  • Room Level: 2
  • Room Type: Bedroom
Room 7
  • Room Dimensions: 15 X 13
  • Room Level: 2
  • Room Type: Bedroom
Room 8
  • Room Dimensions: 9 X 9
  • Room Level: 2
  • Room Type: Office/Study
Room 12
  • Room Level: 1
  • Room Type: Bath - Full
Room 13
  • Room Level: 2
  • Room Type: Bath - 1/2

Property History for 999 Happy Valley Road

DateEvent & SourcePriceAppreciation
Aug 31, 2021

Sold (Public Record)

Public Record #1471929002

$445,000—
Aug 31, 2021

Sold

New England Real Estate Network #4860683

$445,000—
Aug 31, 2021

Pending

New England Real Estate Network #4860683

—
DateEvent & SourcePrice
08/31/2021

Sold (Public Record)

Public Record #1471929002

$445,000
08/31/2021

Sold

New England Real Estate Network #4860683

$445,000
08/31/2021

Pending

New England Real Estate Network #4860683

—

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 999 Happy Valley Road

Taxable ValueLand$77,100Additions$237,100Total$314,200
Tax Record2024$8,474 ($706 / month)
Home Facts
Beds4Baths1.5Total Finished SqFt2,459 SqFtAbove Grade Finished SqFt2,459 SqFtLot Size52,708 SqFtStyleSingle Family ResidenceYear Built1900CountyADDISONAPN(120) 005147.000

Schools near 999 Happy Valley Road

This home is within Addison Central Unified School District.
Rating
School
Type
Grades
Distance
Mary Hogan School
Public - PK to 5
Middlebury Union Middle School
Public - 6 to 8
Middlebury Senior Uhsd #3
Public - 9 to 12
Bridge School
Private - PK to 6
Rating
School
Distance
Mary Hogan School
PublicPK to 5

Middlebury Union Middle School
Public6 to 8

Middlebury Senior Uhsd #3
Public9 to 12

Bridge School
PrivatePK to 6

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 999 Happy Valley Road, Middlebury, VT 05753
$445,000
3
2,459
52,707
959 Happy Valley Road, Middlebury, VT 05753
–
3
2
1,200
43,560
953 Happy Valley Road, Middlebury, VT 05753
$127,000
3
1,200
43,560
21 Painter Hills Road, Middlebury, VT 05753
$257,500
4
2,550
32,670
79 Halpin Road, Middlebury, VT 05753
–
3
3
2,512
42,253
24 Grey Ledge Road, Middlebury, VT 05753
–
4
1
1,224
16,553

Explore Nearby Homes

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Listing Courtesy of IPJ Real Estate

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 08/19/2026 09:14 PM