UNDER CONTRACT

Contingent

$337,000

Est. $2,118/mo —

•

2,162

sq ft

4081 Gamble Rd, Monticello, FL 32344

About this home

Escape to your own private 5-acre retreat! A long, secluded driveway leads to this charming cottage-style 4-bedroom, 2-bath home surrounded by the natural beauty of North Florida. Enjoy the peace and privacy you've been dreaming of with no HOA and no flood insurance required. The thoughtfully designed floor plan features a spacious primary suite and two additional bedrooms on the main level, while upstairs offers a fourth bedroom and an oversized flex room—perfect as a 5th bedroom, home office, playroom, or home gym. The primary suite includes a walk-in closet, double vanity, garden tub, and separate shower. A brand-new roof, two-car carport, and storage shed add to the home's appeal, while the peaceful setting feels worlds away from it all. Yet you're less than 2 miles from I-10 and only 15 minutes from the shops, restaurants, and historic charm of downtown Monticello. If you've been searching for privacy, space, and the freedom to enjoy country living without sacrificing convenience, this is the one.

Single-familyProperty Type

2005Year Built

5 acresLot Size

$156Price/Sq.Ft.

2 spacesParking

Listed by Alisa McMahon • Bluewater Realty Group

Listing updated: Jul 26, 2026 at 09:02pm

Redfin checked: 5 minutes ago

•Source:CATRS #402551

Payment calculator

$2,118 per month

Principal and interest$1,749

Property taxes

$240

HOA dues

Home insurance

$129

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (8)

OPEN SAT, 12PM TO 2PM
$274,900
4 beds4 baths2,224 sq ft
2654 Chateau Ln Unit 1 and 2, Tallahassee, FL 32311
OPEN SAT, 1PM TO 3PM3D WALKTHROUGH
$275,000
4 beds1.5 baths1,722 sq ft
9519 Rose Rd, Tallahassee, FL 32311
OPEN SUN, 11AM TO 1PM
$499,999
4 beds2 baths2,853 sq ft
7420 Hickock Ct, Tallahassee, FL 32311
OPEN SUN, 12PM TO 2PM
$375,000
3 beds2 baths1,753 sq ft
1406 Avondale Way, Tallahassee, FL 32317
OPEN SUN, 2PM TO 4PM
$679,000
4 beds2.5 baths2,345 sq ft
2596 Arendell Way, Tallahassee, FL
OPEN SUN, 2PM TO 4PM
$375,000
4 beds2 baths1,904 sq ft
9870 Brookhollow Ln, Tallahassee, FL 32317
OPEN SUN, 2PM TO 4PM
$425,000
3 beds2 baths1,734 sq ft
3027 Adiron Way, Tallahassee, FL 32317
OPEN SUN, 2PM TO 4PM
$229,900
3 beds2 baths1,620 sq ft
16985 W Chucks Pl, Tallahassee, FL 32309

Around this home

Schools

K - 12
Preschool & daycare

Jefferson K-12 School

Public PreK-12 • Assigned • 8.6mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Market insights

4081 Gamble Rd · $337,000

DAYS ON MARKET

The average home goes pending in 94 days.

SALE-TO-LIST

Most homes are selling 2% below list price.

LIST PRICE

Median sale price in this area is $274,271. (19% lower than this home)

PRICE DROP

17% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Interior features
High ceilings
Primary bedroom downstairs
Split-bedroom layout
Walk-in closet(s)

Bedrooms
Bedroom 2 (12x10)
Bedroom 3 (13x10)
Bedroom 4 (22x12)
Additional bedroom/other room (24x12)

Bathrooms
2 full bathrooms

Kitchen
Dishwasher
Oven
Range
Refrigerator

Laundry & utility
Utility room

Flooring
Carpet
Engineered hardwood
Laminate
Tile

Heating & cooling
Central heating (electric)
Central air
Ceiling fans

Sale and tax history for 4081 Gamble Rd

Sale History
Tax History

Date

Event

Price

CATRS #402551

Jul 30, 2026

Contingent

—

Jul 26, 2026

Price Changed

$337,000

$156/sq ft

Jul 16, 2026

Listed

$347,500

$161/sq ft

CATRS #390451

Oct 27, 2025

Sold

$315,000

$146/sq ft

Sep 24, 2025

Contingent

—

Aug 29, 2025

Listed

$329,500

$152/sq ft

+36

Nestled on a serene 5-acre retreat, this charming storybook cottage feels like a hidden gem, yet it’s just 15 minutes from downtown Monticello’s quaint shops and restaurants. Tucked back from the road for ultimate privacy, this well-maintained home is surrounded by natural beauty, including native plants, wild azaleas, and lush greenery. Step onto the inviting front porch and into a warm, welcoming interior featuring three bedrooms and two baths downstairs. Upstairs, you’ll find two spacious rooms—one perfect as a bonus space and the other as an additional bedroom. Enjoy peaceful mornings and golden sunsets on the front and back decks, where nature is your closest neighbor. A two-car carport and storage shed offer plenty of room for tools and outdoor gear. This magical retreat is the perfect blend of privacy, charm, and convenience. Come experience the fairytale lifestyle just minutes from town! * * Property is being sold AS-IS and Seller will provide new roof at Closing with an Acceptable Offer. * *

CATRS #388336

Aug 29, 2025

Listing Removed

—

Jul 7, 2025

Listed

$349,500

$162/sq ft

CATRS #383824

Jul 7, 2025

Listing Removed

—

May 22, 2025

Price Changed

$374,999

$173/sq ft

Apr 17, 2025

Relisted

—

Apr 16, 2025

Contingent

—

Mar 30, 2025

Listed

$399,000

$185/sq ft

Public record

Beds

Baths

Stories

Lot width

217 ft.

Lot depth

—

Lot size

5 Acres

Year renovated

2005

Finished Sq. Ft.

1,456

Unfinished Sq. Ft.

—

Total Sq. Ft.

1,456

Year built

2005

Style

Single Family Residential

County

Jefferson County

APN

22-1N-3E-0000-007V-0000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 30, 2026.

Climate risks

1/10 Flood Factor

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

3/10 Fire Factor

0.46% chance of being in a wildfire in next 30 years

8/10 Heat Factor

7 days above 107° expected this year, 20 days in 30 years

9/10 Wind Factor

99% chance of strong winds in next 30 years

4/10 Air Factor

7 unhealthy days expected this year, 7 days in 30 years

Provided by First Street

Historical weather

Monticello, FL • 32344

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

90/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10 hrs

6.6 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 4081 Gamble Rd

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $290,000 and $525,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $290K to $525K.

SOLD APR 1, 2026
$465,000 Last sold price
3 beds2 baths2,268 sq ft
308 Cherry Tree Rd, Monticello, FL 32344
$49/sq ft
larger lot
5 years older
SOLD JUL 2, 2026
$335,000 Last sold price
3 beds2 baths1,450 sq ft
9851 Brookhollow Ln, Tallahassee, FL 32317
$75/sq ft
smaller lot
9 years older
SOLD AUG 11, 2026
$525,000 Last sold price
4 beds2 baths1,718 sq ft
333 Post Oak Cir, Monticello, FL 32344
$150/sq ft
smaller lot
15 years newer
SOLD JUN 26, 2026
$337,500 Last sold price
3 beds2 baths1,502 sq ft
406 Robin Road Rd, Monticello, FL 32344
$69/sq ft
29 years older
basement
SOLD APR 7, 2026
$425,000 Last sold price
3 beds2 baths1,960 sq ft
11862 Grazing Buck Ln, Tallahassee, FL 32317
$61/sq ft
smaller lot
10 years older
SOLD FEB 6, 2026
$290,000 Last sold price
3 beds2 baths1,444 sq ft
11096 Tung Grv, Tallahassee, FL 32317
$45/sq ft
smaller lot
16 years older

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3D WALKTHROUGH

$899,000

3 beds2.5 baths2,436 sq ft

9901 Gamble Rd, Monticello, FL 32344

OPEN SUN, 2PM TO 4PM

$375,000

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9870 Brookhollow Ln, Tallahassee, FL 32317

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FOR SALE BY OWNER

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4204 Stoney Pointe Dr, Tallahassee, FL 32309

New listings for sale in 32344

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Details provided by CATRS and may not match the public record. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

Open houses

Nearby open houses (8)

Around this home

Schools

Lifestyle

Market insights

Property details

Sale and tax history for 4081 Gamble Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 4081 Gamble Rd

This home may not be allowing tours right now

Nearby similar homes

New listings for sale in 32344

More real estate resources