OFF MARKET

Listed by Curtis Trousdale • Preferred Properties. Bought with Coldwell Banker Watson Realty/ Ludlow.

Off market jun 2018 for $780K

$2,425,852

Est. refi paymentEst. refi $5,115/mo

•

7,902

sq ft

1037 Bailey Rd, Shrewsbury, VT 05738

About this home

Highfields Farm has been extensively renovated and expanded over the years, not only to preserve its historic character, but to meet and exceed the expectations of the modern family. This 7,902 square foot home features six bedrooms and seven baths, showcasing its ability to host family and friends, further emphasized by the oversized gourmet kitchen, generous rooms and spacious three story guest wing. The stone patio, featuring an outdoor stone fireplace, is a tremendous place for cocktails with guests while soaking in the stunning long range mountain views. Situated on 101+/- acres, there is plenty of space for activities over the diverse landscape of pastures & woodlands. In addition, the home site includes a pond, charming landscaping and excellent lawn space for kids or pets to run & play. Enjoy X-country skiing out your door & the close proximity to Okemo & Killington Mountain ski resorts providing group year-round fun in the snow or under the sun.

Single-familyProperty Type

1840Year Built

101.58 acresLot Size

$307Est. Price/Sq.Ft.

2 car garageParking

Listed by Curtis Trousdale • Preferred Properties

Bought with Catherine Fisher • Coldwell Banker Watson Realty/ Ludlow

Redfin checked: a few seconds ago

•Source:PrimeMLS #4632801

Redfin Estimate

$2,425,852

$1.6M since sold in June 2018$463K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 131.6% higher than the average sale price ($1.05M) of 6 comparable homes.

SOLD MAR 25, 2026
$1,550,000
A
7 beds5.5 baths6,415 sq ft
444 Tin Shanty Rd, Shrewsbury, VT 05738
SOLD AUG 21, 2026
$575,000
B
4 beds2.5 baths2,520 sq ft
5100 Route 100, Plymouth, VT 05056
SOLD MAY 29, 2026
$1,200,000
C
6 beds3 baths3,584 sq ft
96 Tabor Rd, Shrewsbury, VT 05738
SOLD JUN 29, 2026
$650,000
D
4 beds4 baths3,653 sq ft
1595 Healdville Rd, Mt Holly, VT 05758
SOLD AUG 21, 2026
$1,200,000
E
8 beds5 baths3,814 sq ft
7030 U.S. Route 4, Bridgewater, VT 05034
SOLD NOV 7, 2025
$1,110,000
F
5 beds3.5 baths2,649 sq ft
331 Route 100 N, Plymouth, VT 05056

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$4,378/mo

Redfin rental estimate

List your home for rent

Market trends in 05738, VT

Last updated September 2026

Sale-to-list price

90.6%

5.6% MoM

Median sale price

$630K

$570K MoM

Avg. days on market

76d

57 days MoM

Recently sold homes

0 MoM

New listings for sale

VIDEO TOUR
$795,000
3 beds3 baths3,841 sq ft
415 Crown Point Rd, Shrewsbury, VT 05738
See all

Provided by Redfin

Sale history for 1037 Bailey Rd

Year

Property tax

Land + Additions

Assessment*

2025

$19,359 (+1.7%)

$432,100 + $833,700

$1,265,800

2024

$19,039 (+10.6%)

$432,100 + $833,700

$1,265,800

2023

$17,208 (+6.3%)

$432,100 + $833,700

$1,265,800

2022

$16,185 (−7.9%)

$830,000

2021

$17,579 (+12.0%)

$830,000

2020

$15,697 (−2.1%)

$830,000

2019

$16,028 (−2.9%)

$830,000

2018

$16,499 (−20.6%)

$830,000

2017

$20,784 (−9.1%)

$236,100 + $833,700

$1,069,800

2016

$22,862 (−2.5%)

$243,200 + $973,300

$1,216,500

2015

$23,437

$243,200 + $973,300

$1,216,500

Tax history for 1037 Bailey Rd

Year

Property tax

Land + Additions

Assessment*

2025

$19,359 (+1.7%)

$432,100 + $833,700

$1,265,800

2024

$19,039 (+10.6%)

$432,100 + $833,700

$1,265,800

2023

$17,208 (+6.3%)

$432,100 + $833,700

$1,265,800

2022

$16,185 (−7.9%)

$830,000

2021

$17,579 (+12.0%)

$830,000

2020

$15,697 (−2.1%)

$830,000

2019

$16,028 (−2.9%)

$830,000

2018

$16,499 (−20.6%)

$830,000

2017

$20,784 (−9.1%)

$236,100 + $833,700

$1,069,800

2016

$22,862 (−2.5%)

$243,200 + $973,300

$1,216,500

2015

$23,437

$243,200 + $973,300

$1,216,500

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

7.5

Stories

Lot width

—

Lot depth

—

Lot size

206.38 Acres

Year renovated

—

Sq. Ft.

7,902

Year built

1840

Style

Single Family Residential

County

Rutland County

APN

59418710591

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 23, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 2
Location: Attached
Auto Open, Heated
Driveway, Garage

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 4
# of Baths (3/4): 2
# of Baths (1/2): 1

Basement Information
Basement: Yes
Basement Access: Interior
Bulkhead, Climate Controlled, Concrete, Crawl Space, Partial, Stairs - Interior, Unfinished

Other Interior Features
# of Rooms: 12
Flooring: Ceramic Tile, Hardwood, Softwood
Water Heater: Domestic, Off Boiler, Oil, Owned
Attic, Cathedral Ceiling, Cedar Closet, Ceiling Fan, Dining Area, Fireplace - Wood, Fireplaces - 3+, Hearth, In-Law Suite, Kitchen Island, Kitchen/Dining, Laundry Hook-ups, Master Bedroom With Bath, Vaulted Ceiling, Walk-in Closet, Laundry - 1st Floor

Equipment & Appliance Information
Dishwasher, Disposal, Dryer, Exhaust Hood, Freezer, Microwave, Range - Gas, Refrigerator, Washer
Carbon Monoxide Detector, Satellite Dish, Security System, Smoke Detector, Smoke Detectr-Hard Wired

Room 1 Information
Kitchen
Kitchen
Dimensions: 23 x 20
Level: 1

Room 2 Information
Dining Room
Dimensions: 24'1 x 12'5
Level: 1

Room 3 Information
Living Room
Dimensions: 24'10 x 21'4
Level: 1

Room 4 Information
Family Room
Dimensions: 20 x 18
Level: 1

Room 5 Information
Office/Study
Dimensions: 12'7 x 8'7
Level: 1

Room 6 Information
Utility Room
Utility Room
Dimensions: 16 x 7'5
Level: 1

Room 7 Information
Master Bedroom
Dimensions: 19'10 x 17'9
Level: 2

Room 8 Information
Bedroom
Dimensions: 24'2 x 12'5
Level: 2

Room 9 Information
Bedroom
Dimensions: 12'8 x 11'9
Level: 2

Room 10 Information
Bedroom
Dimensions: 10'1 x 7'11
Level: 2

Room 11 Information
Bedroom
Dimensions: 13'5 x 11'7
Level: 1

Room 12 Information
Bedroom
Dimensions: 13'5 x 11'7
Level: 1

Room 13 Information
Den
Level: 1

Room 14 Information
Sunroom
Dimensions: 25'2 x 9'6
Level: 1

Room 15 Information
Master Bedroom Suite
Dimensions: 14'6 x 11
Level: 2

Room 16 Information
Full Bath
Level: 1

Room 17 Information
Full Bath
Level: 2

Room 18 Information
Full Bath
Level: 2

Room 19 Information
Full Bath
Level: 3

Room 20 Information
3/4 Bath
Level: 1

Room 21 Information
3/4 Bath
Level: 3

Room 22 Information
1/2 Bath
Level: 1

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 7902
Approximate Sq. Ft. Total: 11459
Balcony, Fence - Dog, Guest House, Patio, Porch - Covered, Window Screens
Construction: Wood Frame
Foundation: Block, Concrete, Stone
Roof: Slate
Exterior: Clapboard, Wood

Driveway
Brick/Pavers

Lot, Zoning, & Easement Information
Agricultural, Country Setting, Field/Pasture, Mountain View, Pond, View, Wooded

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 1840

Financial

Assessment Information
Assessment Amount: 1069800

Tax Information
Tax Year: 2017
Gross Amount Tax: 20784.08
SPAN Number: 59418710591

Other Tax Information
Page Deed: 635

Utilities

Heating & Cooling Information
Cooling: Attic Fan, Multi Zone
Heat: Baseboard, Hot Water, Multi Zone, Radiant, Radiator
Heat Fuel: Oil

Sewer Information
Private, Septic

Electric Information
Electric Company: Green Mountain Power
200 Amp, Circuit Breaker(s), Generator

Water Information
Private, Purifier/Soft

Other Utilities Information
Fuel Company: Irving
Phone Company: VTel

Location

School Information
School District: Rutland South
Elementary School: Shrewsbury Mountain School
Elementary School: Shrewsbury Mountain School
Middle/Jr School: Mill River Union High School

Neighborhood Information
Near Snowmobile Trails

Road Information
Road Frontage: Yes
Road Frontage Length: 1180
Gravel, Public

Other Location Information
Directions: RT. 103 in Mt. Holly take Hortonville Road, this turns into Shrewsbury Rd which turns into Mt. Holly Road. Turn right on to Eastham Rd, then left on Bailey Rd, house on left, no sign. Northwest entrance of Bailey Rd is closed in winter.

Public facts

Beds: 6
Baths: 7.5
Sq. Ft.: 7,902
Stories: 2.0
Lot Size: 206.38 acres
Style: Single Family Residential
Year Built: 1840
Year Renovated: —
County: Rutland County
APN: 59418710591

Home facts updated by county records on Oct 23, 2026

Other

Water Body Information
Pond
Flood Zone: Unknown

Documents & Disclosures
Documents Available: Deed, Plot Plan, Property Disclosure, Survey

Around this home

Schools

Shrewsbury Mountain School

Public PreK-6 • Assigned • 2.3mi

4/10

Mill River Unified School District #40

Public 7-12 • Assigned • 9.2mi

4/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Historical weather

Shrewsbury, VT • 05738

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.3 hours in June and 3.4 hours in December, placing it below the U.S. average for solar exposure.

8.3 hrs

3.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.31M – $2.79M

Sell confidently with a local market expert in Shrewsbury. 3 minutes to get started.

Nearby similar homes

$2,195,000

5 beds4 baths7,374 sq ft

1702 N Puckerbrush Rd, Reading, VT 05062

Over 141 acres • Chef's kitchen • Walk-in pantry

VIDEO TOUR

$1,970,000

5 beds5.5 baths4,965 sq ft

93 Godfrey Rd, Ludlow, VT 05149

Expansive lawns • Perennial gardens • Picturesque ponds

$519,000

3 beds1.5 baths1,097 sq ft

4726 Route 100, Plymouth, VT 05056

Propane rinnai heat • Electric baseboards • Hot tub

FOR SALE BY OWNER

$875,000

4 beds3.5 baths2,983 sq ft

790 Chapman Rd, Ludlow, VT 05149

Wood burning stove • Open concept living • Deck access

$300,000

3 beds2 baths2,220 sq ft

547 N Main St, Wallingford, VT 05773

First-floor bedroom • First-floor laundry • Large backyard

VIDEO TOUR

$695,000

3 beds2.5 baths3,110 sq ft

19 Lawridge Hts, Ludlow, VT 05149

Renovated farmhouse • Oversized great room • Expansive windows

New listings for sale in 05738

VIDEO TOUR

$795,000

3 beds3 baths3,841 sq ft

415 Crown Point Rd, Shrewsbury, VT 05738

Log home • Stone fireplace • Gourmet kitchen

Home values near 1037 Bailey Rd

Data from public records.

Address	Redfin Estimate
1204 Bailey Road, Shrewsbury, VT 6 Beds \| 5 Baths \| 4719 Sq. Ft.	$1,502,333
1204 Bailey Road, Shrewsbury, VT 5 Beds \| 4 Baths \| 4700 Sq. Ft.	$1,441,064

Address	Redfin Estimate
856 Bailey Road, Shrewsbury, VT 3 Beds \| 2 Baths \| 1632 Sq. Ft.	$481,704
3661 Eastham Road, Shrewsbury, VT 4 Beds \| 4.5 Baths \| 4500 Sq. Ft.	$1,134,825

Address	Redfin Estimate
780 Bailey Road, Shrewsbury, VT 5 Beds \| 3.5 Baths \| 4091 Sq. Ft.	$1,384,050
474 Tabor Road, Shrewsbury, VT 4 Beds \| 2 Baths \| 1548 Sq. Ft.	$287,081

Property information provided by PrimeMLS when last listed in 2017. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Rutland County	Agents near me	South Burlington, VT homes for sale	Rutland County Housing Market
Houses for sale near me	Burlington, VT homes for sale	Brattleboro, VT homes for sale
Land for sale near me	Stowe, VT homes for sale	Waterbury, VT homes for sale
Open Houses near me	Woodstock, VT homes for sale	Rutland County Property Records
Condos for sale near me	Montpelier, VT homes for sale	VT New Listings

Castleton homes for sale
Rutland homes for sale
Brandon homes for sale

Saratoga County homes for sale
Windham County homes for sale
Cheshire County homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 05738, VT

Sale history for 1037 Bailey Rd

Tax history for 1037 Bailey Rd

Public record

Property details

Around this home

Schools

Lifestyle

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05738

Home values near 1037 Bailey Rd

More real estate resources