OFF MARKET

Off Market Dec 2018 for $300K

—

Est. refi paymentEst. refi $1,917/mo

•

1 ba

•

1,136

sq ft

2865 Whippoorwill Rd, Madison, VA 22727

About this home

36 acre farm-FT. Valley with beautiful mountain views, swift flowing spring, majestic trees, 4-stall barn, fencing, garage w/ studio above, potting shed etc. Finish the canvas with your dream home on sought after Whippoorwill Rd! (As-Is Farmhouse is a tear down. "Have Low quote to demolish"). Absolute serenity. Moments to hiking in White Oak Canyon & Old Rag, & the towns of Sperryville and Madison.

Single-familyProperty Type

1900Year Built

35.77 acresLot Size

$264Price/Sq.Ft.

1 spaceParking

Listed by Denise Chandler • Country Places Realty, LLC

•540-675-1200 (broker)

Bought with Martin Woodard • Cheri Woodard Realty

•540-987-8500 (broker)

•cw@cheriwoodard.com (broker)

Redfin checked: a minute ago

•Source:BRIGHT MLS #1002335152

Redfin Estimate

Unfortunately, we don't have enough data to generate an accurate Estimate at this time.

Market trends in 22727, VA

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

98.0%

0.6% MoM

Median sale price

$394K

$69K MoM

Avg. days on market

41d

5 days MoM

Recently sold homes

4 MoM

New listings for sale

NEW 11 HRS AGO
$377,700
4 beds2 baths2,028 sq ft
247 Little Church Ln, Madison, VA 22727
(540) 459-4002
COMING SOON
$1,625,000
3 beds3 baths3,802 sq ft
3638 Oak Park Rd, Madison, VA 22727
(434) 960-1366
NEW 35 HRS AGO
$424,900
4 beds2 baths1,812 sq ft
359 Malvern Dr, Madison, VA 22727
(540) 825-1800
$499,900
3 beds2 baths1,288 sq ft
2242 Shelby Rd, Madison, VA 22727
(703) 378-8810
$400,000
3 beds2 baths1,248 sq ft
898 Seville Rd, Rochelle, VA 22727
(540) 347-5277
$299,999
3 beds2 baths930 sq ft
193 Gate, Madison, VA 22727
(540) 812-3233
See all

Provided by Redfin

Sale history for 2865 Whippoorwill Rd

Date

Event

Price

BRIGHT MLS #1002601342

Dec 14, 2018

Sold

$300,000

$264/sq ft

Nov 27, 2018

Pending

—

Oct 20, 2018

Relisted

—

Oct 9, 2018

Contingent

—

Sep 6, 2018

Listed

$319,000

$281/sq ft

+18

36 acre Farm-Ft. Valley with beautiful mountain views, swift flowing stream, majestic trees, 4-stall barn, fencing, garage w/ studio above, potting shed etc. Finish the canvas with your dream home on sought after Whippoorwill Rd! (As-Is Farmhouse is a tear down. "Have Low quote to demolish"). Absolute serenity. Moments to hiking in White Oak Canyon & Old Rag, & the towns of Sperryville and Madison.

BRIGHT MLS #1002335152

Dec 14, 2018

Sold

$300,000

$264/sq ft

Nov 27, 2018

Pending

—

Oct 20, 2018

Relisted

—

Oct 9, 2018

Contingent

—

Aug 29, 2018

Listed

$319,000

$281/sq ft

BRIGHT MLS #1002390128

Sep 5, 2018

Listing Removed

—

Sep 4, 2018

Listed

$319,000

$281/sq ft

MRIS #MA10337231

Sep 5, 2018

Delisted

—

Sep 4, 2018

Listed

Year

Property tax

Land + Additions

Assessment*

2025

$5,082 (+319.5%)

$343,800 + $523,300

$867,100

2024

$1,211

$275,600 + $33,400

$309,000

2023

$1,211

$275,600 + $33,400

$309,000

2022

$1,211

$275,600 + $33,400

$309,000

2021

$1,211 (+4.2%)

$275,600 + $33,400

$309,000

2020

$1,162 (+1.4%)

$275,600 + $33,400

$309,000

2019

$1,146 (−10.0%)

$275,600 + $33,400

$309,000

2018

$1,273

$307,900 + $57,200

$365,100

2017

$1,273 (+63.8%)

$307,900 + $57,200

$365,100

2013

$777

$70,000 + $46,000

$116,000

Tax history for 2865 Whippoorwill Rd

Year

Property tax

Land + Additions

Assessment*

2025

$5,082 (+319.5%)

$343,800 + $523,300

$867,100

2024

$1,211

$275,600 + $33,400

$309,000

2023

$1,211

$275,600 + $33,400

$309,000

2022

$1,211

$275,600 + $33,400

$309,000

2021

$1,211 (+4.2%)

$275,600 + $33,400

$309,000

2020

$1,162 (+1.4%)

$275,600 + $33,400

$309,000

2019

$1,146 (−10.0%)

$275,600 + $33,400

$309,000

2018

$1,273

$307,900 + $57,200

$365,100

2017

$1,273 (+63.8%)

$307,900 + $57,200

$365,100

2013

$777

$70,000 + $46,000

$116,000

*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

1.5

Stories

Lot width

—

Lot depth

—

Lot size

35.77 Acres

Year renovated

—

Sq. Ft.

2,880

Year built

1900

Style

Other

County

Madison County

APN

16 10B

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 23, 2026.

Property details

Parking

Parking Information
# of Detached Garage Spaces: 1
Garage Features: Garage - Front Entry
# of Total Garage and Parking Spaces: 1
Has Garage
# of Garage Spaces: 1
Gravel Driveway
Driveway, Detached Garage

Interior

Bedroom Information
# of Bedrooms On 1st Upper Level: 2

Bathroom Information
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Full): 1

Interior Information
Appliances: Washer/Dryer Hookups Only, Dryer, Oven/Range - Electric, Refrigerator, Washer
Interior Features: Attic, Other, Entry Level Bedroom, Wood Floors
Living Area Sq.Ft. Source: Estimated
Wall & Ceiling Types: Dry Wall

Room Information
Living Room, Dining Room, Master Bedroom, Bedroom 2, Bedroom 3, Kitchen, Mud Room

Basement Information
Basement: No

Exterior

Property Information
Not Federal Flood Zone
Horse Amenities: Horses Allowed
Improvement Assessed Value: $57,200
Ownership Interest: Fee Simple
Property Condition: As-is Condition
Year Built Source: Estimated

Building Information
Construction Materials: Wood Siding, Frame
Foundation Details: Crawl Space, Block
Other Structures: Above Grade
Roof: Metal
Structure Type: Detached

Exterior Information
Satellite Dish

Lot Information
Lot Features: Backs to Trees, Partly Wooded, Stream/Creek, Private
Topography: Rolling, Sloped
Tidal Water: No

Land Information
Crops Included: No
Land Assessed Value: $307,900

Farm Information
Farm Features: Shed(s), Corral
Land Area Units: Acres
Horse
Remarks: 36 acre farm-FT. Valley with beautiful mountain views, swift flowing spring, majestic trees, 4-stall barn, fencing, garage w/ studio above, potting shed etc. Finish the canvas with your dream home on sought after Whippoorwill Rd! (As-Is. Farmhouse is a tear down. "Have Low Quote to demolish"). Absolute serenity. Moments to hiking in White Oak Canyon & Old Rag, & the towns of Sperryville and Madison.
Farm Land Preservation: No

Above Grade Information
Finished Sq.Ft.: 1,136
Finished Sq.Ft. Source: Estimated

Financial

Tax Information
Agricultural Tax Due: No
County Tax: $1,273
Tax Assessed Value: $365,100
Tax Year: 2017
Tax Annual Amount: $1,273

Assessments Information
Year Assessed: 2013

Utilities

Utilities Information
Wood Burn Stove
Heating Fuel: Wood
Hot Water: Electric
Sewer Septic: Holding Tank
Water Source: Spring

Location

School Information
School District Name: MADISON COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent

Location Information
Outside City Limits
Directions: Sperryville: US-522 S towards Culpeper. 0.6 miles turn right to VA-231 S (FT Valley Rd). Go 9.9 miles. Make sharp left to SR 643 (Church Hill Rd) by Little Country Store. At end turn R to State Rte 603 (Whippoorwill Rd). Go 0.9 mi. On right.
Location Type: Spring
Mean Low Water Feet: 0
Road Surface Type: Gravel

Waterfrontage Information
Distance To Body Of Water: Less than 1 Block
Water Access
Water Oriented
Water Body Type: Spring
Water Body Name: SPRING

Public facts

Beds: 2
Baths: 1.5
Sq. Ft.: 2,880
Stories: 2.0
Lot Size: 35.77 acres
Style: Other
Year Built: 1900
Year Renovated: —
County: Madison County
APN: 16 10B

Home facts updated by county records on Jul 23, 2026

Around this home

Schools

Waverly Yowell Elementary School

Public 3-5 • Assigned • 8.7mi

4/10

William H. Wetsel Middle School

Public 6-8 • Assigned • 10.2mi

4/10

Madison County High School

Public 9-12 • Assigned • 10.2mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

4/10 Fire Factor

3% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 104° expected this year, 17 days in 30 years

2/10 Wind Factor

2% chance of strong winds in next 30 years

1/10 Air Factor

0 unhealthy days expected this year, 0 days in 30 years

Provided by First Street

Historical weather

Madison, VA • 22727

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

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

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New listings for sale in 22727

NEW 11 HRS AGO

$377,700

4 beds2 baths2,028 sq ft

247 Little Church Ln, Madison, VA 22727

(540) 459-4002

COMING SOON

$1,625,000

3 beds3 baths3,802 sq ft

3638 Oak Park Rd, Madison, VA 22727

(434) 960-1366

NEW 35 HRS AGO

$424,900

4 beds2 baths1,812 sq ft

359 Malvern Dr, Madison, VA 22727

(540) 825-1800

$499,900

3 beds2 baths1,288 sq ft

2242 Shelby Rd, Madison, VA 22727

(703) 378-8810

$400,000

3 beds2 baths1,248 sq ft

898 Seville Rd, Rochelle, VA 22727

(540) 347-5277

$299,999

3 beds2 baths930 sq ft

193 Gate, Madison, VA 22727

(540) 812-3233

Home values near 2865 Whippoorwill Rd

Data from public records.

Address	Redfin Estimate
2604 Whippoorwill Road, Madison, VA 4 Beds \| 4.5 Baths \| 5600 Sq. Ft.	$3,600,822
3493 Whippoorwill Road, Madison, VA 3 Beds \| 2.5 Baths \| 2520 Sq. Ft.	$561,884

Address	Redfin Estimate
2623 Whippoorwill Road, Madison, VA 4 Beds \| 2 Baths \| 1584 Sq. Ft.	$2,010,280
2311 Whippoorwill Road, Madison, VA 2 Beds \| 2.5 Baths \| 1370 Sq. Ft.	$727,790

Address	Redfin Estimate
3018 Whippoorwill Road, Etlan, VA 3 Beds \| 3 Baths \| 4182 Sq. Ft.	$1,130,591
2684 Whippoorwill Road, Madison, VA 2 Beds \| 3 Baths \| 2682 Sq. Ft.	$986,423

Property information provided by BRIGHT MLS when last listed in 2018. This data may not match . Learn more.

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About this home

Redfin Estimate

Market trends in 22727, VA

Sale history for 2865 Whippoorwill Rd

Tax history for 2865 Whippoorwill Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 22727

Home values near 2865 Whippoorwill Rd

More real estate resources