This home's estimate is 28.9% lower than the average sale price ($483K) of 6 comparable homes.
Search- Overview
- Sale & tax history
- Property details
- Neighborhood
- Climate



































769 Whippoorwill Rd, Monticello, FL 32344
About this home
Solitude awaits you on this nearly 5 acre property. This property features a quaint 1 bedroom, 1 bath cottage with a gorgeous, recently remodeled kitchen, complete with over-sized windows giving you wonderful views of your pasture, woods and a stocked fish pond. Also included is a 2 bedroom, 1 1/2 bath home; chicken coop, modified horse stable or work/storage space, shed, plenty of land for planting and even a water supply complete with added hand crank assembly to provide well water even if electricity is temporarily disrupted. Indeed, this property offers all you will need to live off the land if you ever desire to do so! Located close to I-10, you can be in Tallahassee after just 1 exit. New roof on 1 bedroom cottage with acceptable offer! Don't hesitate, come see this lovely property and make it your own.
Redfin Estimate
Earn from this home
Get cash now or lower your monthly rate
List your home for rent
Market trends in 32344, FL
Last updated September 2026
Buyer's Market
Seller's Market
Buyer's market
See all
Provided by Redfin
Sale history for 769 Whippoorwill Rd
$108/sq ft
$108/sq ft
$79/sq ft
$86/sq ft
$5/sq ft
Tax history for 769 Whippoorwill Rd
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Property details
Parking
- Parking
- Features: Driveway
Interior
- Bathroom Information
- # of Full Bathrooms: 2
- # of Half Bathrooms: 1
- Room Information
- Room Types: Guest Quarters, Utility Room, Workshop
- Room 1 Information
- Other
- Dimensions: 15x10
- Room 2 Information
- Living Room
- Dimensions: 18x16
- Room 3 Information
- Family Room
- Dimensions: 18x15
- Room 4 Information
- Bedroom 3
- Dimensions: 13x12
- Equipment
- Appliances: Dryer, Refrigerator, Stove, Washer
- Interior Features
- Flooring: Tile
- Other Features: High Ceilings, Window Treatments, Primary Downstairs, Walk-In Closet(s), Workshop
Exterior
- Building Information
- Stories: 1
- Construction Details: Wood Siding
- Exterior Features
- Exterior Features: Fully Fenced, Storage
- Patio And Porch Features: Covered, Deck, Porch
- Other Structures: Guest House
- Fencing: Fenced
- Land Information
- Horse Amenities: Horses Allowed
- Lot Information
- Lot Size Acres: 4.72
- Lot Size Dimensions: 464x380x222x249x456
- Road Responsibility: Public Maintained Road
- Road Surface Type: Paved
- Waterfront Features: Pond
- Property Information
- Has View
Financial
- Lease Information
- Sale Or Lease Indicator: For Sale
Utilities
- Utility Information
- Sewer: Septic Tank
- Heating & Cooling
- Has Cooling
- Cooling: Central Air, Ceiling Fan(s), Electric
- Has Heating
- Heating: Central, Electric, Wood Stove
Public facts
- Beds: 1
- Baths: 1.0
- Sq. Ft.: 768
- Stories: 1.0
- Lot Size: 4.72 acres
- Style: Single Family Residential
- Year Built: 1975
- Year Renovated: 1980
- County: Jefferson County
- APN: 22-1N-3E-0000-0077-0000
Around this home
Schools
Public PreK-12 • Assigned • 8.5mi
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
Minimal risk of a flood reaching the building in the next 30 years
1% chance of being in a wildfire in next 30 years
7 days above 107° expected this year, 20 days in 30 years
99% chance of strong winds in next 30 years
7 unhealthy days expected this year, 7 days in 30 years
Sun exposure
In this area, properties receive around 9.8 hours in June and 5.9 hours in December, placing it above the U.S. average for solar exposure.
Sell confidently with a local market expert in Monticello. 3 minutes to get started.
Nearby similar homes
New listings for sale in 32344
Home values near 769 Whippoorwill Rd
| Address | Redfin Estimate |
|---|---|
2 Beds | 2 Baths | 1680 Sq. Ft. | $138,271 |
3 Beds | 2 Baths | 1976 Sq. Ft. | $321,178 |
| Address | Redfin Estimate |
|---|---|
3 Beds | 2 Baths | 1728 Sq. Ft. | $158,679 |
2 Beds | 1 Baths | 768 Sq. Ft. | $149,867 |
| Address | Redfin Estimate |
|---|---|
3 Beds | 2 Baths | 1880 Sq. Ft. | $191,076 |
4 Beds | 2 Baths | 2310 Sq. Ft. | $226,455 |
More real estate resources
- Zip Codes
- Cities
- Popular Searches
| 32344 homes for sale |
| Bradfordville homes for sale | |||
| Tallahassee homes for sale | |||
| Thomasville homes for sale |
Find us
Subsidiaries
Affiliated Business
Copyright: © 2026 Redfin. All rights reserved.
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.
































United States
Canada