Are yards well-kept in Monticello, FL?

As of early 2026, 100% of users say yards are well-kept

Is parking easy in Monticello, FL?

As of early 2026, 91% of users say parking is easy

Is a car needed in Monticello, FL?

As of early 2026, 85% of users say car is needed

Do kids play outside in Monticello, FL?

As of early 2026, 73% of users say kids play outside

Is Monticello, FL quiet?

As of early 2026, 73% of users say it's quiet

Would people walk alone at night in Monticello, FL?

As of early 2026, 71% of users say people would walk alone at night

Does Monticello, FL show holiday spirit?

As of early 2026, 67% of users say there's holiday spirit

Is there wildlife in Monticello, FL?

As of early 2026, 65% of users say there's wildlife

Is Monticello, FL dog-friendly?

As of early 2026, 60% of users say it's dog friendly

Do residents of Monticello, FL plan to stay at least 5 years?

As of early 2026, 59% of users say they plan to stay for at least 5 years

Are the streets well-lit in Monticello, FL?

As of early 2026, 57% of users say streets are well-lit

Is Monticello, FL walkable to grocery stores?

As of early 2026, 56% of users say it's walkable to grocery stores

Are neighbors friendly in Monticello, FL?

As of early 2026, 51% of users say neighbors are friendly

Is Monticello, FL walkable to restaurants?

As of early 2026, 50% of users say it's walkable to restaurants

Does Monticello, FL have sidewalks?

As of early 2026, 39% of users say there are sidewalks

Are there community events in Monticello, FL?

As of early 2026, 31% of users say there are community events

UNDER CONTRACT

5 ACRES

4081 Gamble Rd
Monticello, FL 32344

4 Beds
2 Baths
2,162 sqft (on 5 acres)

$337,000

Est. Mortgage $2,205/mo*

Get Pre-Qualified

$337,000

Est. Mortgage $2,205/mo*

Get Pre-Qualified

4 Beds

2 Baths

2,162 sqft

(on 5 acres)

We estimate this home will sell faster than 100% nearby.

Home Highlights

Parking

2 Carport Spaces

Outdoor

Deck

Climate Control

Heating & Cooling

HOA

None

Price/Sqft

$156

Listed

18 days ago

Local Information

Map ViewExplore the area around 4081 Gamble Rd.
Schools1 Preschool School2 Elementary Schools3 Middle Schools3 High Schools
Shop & Eat

-- mins to

Commute Destination

About this House

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.

We estimate this home will sell faster than 100% nearby.

Home Details for 4081 Gamble Rd

Interior Features
Interior Details Number of Rooms: 9Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Family Room, Kitchen, Living Room, Other
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout Living Area: 2162 Square Feet
Appliances & Utilities Appliances: Dishwasher, Oven, Range, RefrigeratorDishwasherRefrigerator
Heating & Cooling Heating: Central,ElectricHas CoolingAir Conditioning: Central Air,Ceiling Fan(s),ElectricHas HeatingHeating Fuel: Central
Fireplace & Spa No Fireplace
Windows, Doors, Floors & Walls Flooring: Carpet, Engineered Hardwood, Laminate, Tile
Levels, Entrance, & Accessibility Floors: Carpet, Engineered Hardwood, Laminate, Tile
View No ViewView: None

Exterior Features
Exterior Home Features Patio / Porch: DeckFoundation: CrawlspaceNo Private Pool
Parking & Garage Number of Carport Spaces: 2Number of Covered Spaces: 2Has a CarportNo Attached GarageParking Spaces: 2Parking: Carport,Two Spaces,Gated
Frontage Responsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer Sewer: Septic Tank

Days on Market
Cumulative Days on Market: 11Days on Market: 18

Property Information
Year Built Year Built: 2005
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Two Story,Traditional
Building Construction Materials: Block, Modular/Prefab, Concrete, Vinyl SidingNot Attached PropertyDoes Not Include Home Warranty

Price & Status
Price List Price: $337,000Price Per Sqft: $156
Status Change & Dates Off Market Date: Sun Jul 26 2026

Active Status
MLS Status: Active Under Contract

Location
Direction & Address City: MonticelloCommunity: None
School Information Elementary School: Jefferson County K-12 SchoolJr High / Middle School: Jefferson County K-12 SchoolHigh School: Jefferson County K-12 School

Agent Information
Listing Agent Listing ID: 402551

Building
Building Area Building Area: 2162 Square Feet

HOA
HOA Fee Includes: NoneHOA Fee Frequency (second): AnnuallyHOA Fee: No HOA Fee

Lot Information
Lot Area: 5 Acres

Offer
Listing Terms: Cash, Conventional, FHA, VA Loan

Miscellaneous
Mls Number: 402551Living Area Range Units: Square FeetProjected Close Date: Fri Sep 25 2026Zillow Contingency Status: Under ContractAbove Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Units: Square Feet

Additional Information
Days On Market Replication: 11

Last check for updates: about 12 hours ago

Listing courtesy of Alisa McMahon, (850) 510-3961

Bluewater Realty Group

Source: TBR, MLS#402551

Also Listed on TBR.

Market trends in Monticello

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

5MoM

Price History for 4081 Gamble Rd

Date	Price	Event	Source
07/27/2026	$337,000	Contingent	TBR #402551

07/25/2026	$337,000	PriceChange	TBR #402551
Price Change $10,500 (-3%)
07/16/2026	$347,500	Listed For Sale	TBR #402551

10/27/2025	$315,000	Sold	TBR #390451
Recording Date 10/27/2025 County Transfer Tax N/A Total Transfer Tax N/A
09/24/2025	$329,500	Contingent	TBR #390451

08/29/2025	$329,500	PriceChange	TBR #390451
Price Change $20,000 (-6%)
07/07/2025	$349,500	PriceChange	TBR #388336
Price Change $25,499 (-7%)
05/22/2025	$374,999	PriceChange	TBR #383824
Price Change $24,001 (-6%)
04/18/2025	$399,000	PendingToActive	TBR #383824

04/17/2025	$399,000	Contingent	TBR #383824

04/02/2025	$399,000	Listed For Sale	TBR #383824

Similar Homes You May Like

Skip to last item

$355,000
3 bd
2.5 ba
1,838 sqft
5385 Paddington Dr,
Tallahassee, FL 32309
Superior Realty Group LLC
0.28 ACRES
$399,000
4 bd
2 ba
1,794 sqft
3489 Cedarwood Trl,
Tallahassee, FL 32312
Hill Spooner & Elliott Inc
4.05 ACRES
$395,000
3 bd
2 ba
1,891 sqft
1637 N Jefferson Hwy,
Monticello, FL 32344
All Realty Services
1.45 ACRES
$415,000
3 bd
2.5 ba
1,944 sqft
6281 Longwood Ct,
Tallahassee, FL 32311
The Naumann Group Real Estate
0.32 ACRES
$334,000
3 bd
2 ba
1,545 sqft
6447 Joe Cotton Trl,
Tallahassee, FL 32309
Coldwell Banker Hartung
0.38 ACRES
$420,500
3 bd
2 ba
1,856 sqft
747 Eagle View Dr,
Tallahassee, FL 32311
Keller Williams Town & Country
$384,500
4 bd
2.5 ba
2,080 sqft
227 Waynard Way,
Tallahassee, FL 32317
Kelly & Kelly Properties, Inc
$399,000
4 bd
2 ba
1,762 sqft
1349 Old Village Rd,
Tallahassee, FL 32312
Big Fish Real Estate Services
1 ACRE
$349,000
3 bd
2 ba
1,774 sqft
8156 Waukeenah Hwy,
Monticello, FL 32344
Kelly & Kelly Properties, Inc
0.26 ACRES
$339,900
3 bd
2 ba
1,621 sqft
8381 Hunters Ridge Trl,
Tallahassee, FL 32312
Coldwell Banker Hartung
$195,000
2 bd
1.5 ba
1,092 sqft
2611 Panther Creek Rd,
Tallahassee, FL 32308
Keller Williams Town & Country
0.25 ACRES
$198,500
3 bd
1 ba
1,250 sqft
815 Peggy Dr,
Tallahassee, FL 32305
Re/Max Professionals Realty
0.7 ACRES
$499,900
4 bd
3 ba
2,766 sqft
406 Piedmont Dr,
Tallahassee, FL 32312
1st Choice Real Estate Service
$347,000
3 bd
2 ba
1,467 sqft
1080 Winter Ln,
Tallahassee, FL 32311
EXP Realty, LLC
$419,000
4 bd
2 ba
1,843 sqft
1328 Old Village Rd,
Tallahassee, FL 32312
Hill Spooner & Elliott Inc
NEW - 1 DAY AGO
0.32 ACRES
$439,000
3 bd
2 ba
1,737 sqft
3405 Treaty Oak Trl,
Tallahassee, FL 32312
Big Fish Real Estate Services
0.53 ACRES
$425,000
3 bd
2 ba
2,142 sqft
2671 Bantry Bay Dr,
Tallahassee, FL 32309
Coldwell Banker Hartung
$349,999
4 bd
2 ba
1,786 sqft
8412 Wellesly Pl,
Tallahassee, FL 32312
The Naumann Group Real Estate
$310,000
3 bd
2.5 ba
1,569 sqft
4348 Benchmark Trce,
Tallahassee, FL 32317
Xcellence
$355,000
3 bd
2 ba
1,505 sqft
1039 Winter Ln,
Tallahassee, FL 32311
Keller Williams Town & Country
5.06 ACRES
$499,000
5 bd
2 ba
2,268 sqft
398 Tecumseh Rd,
Monticello, FL 32344
Kelly & Kelly Properties, Inc
$189,000
2 bd
2.5 ba
1,262 sqft
1242 Chee Ln #D,
Tallahassee, FL 32304
The Naumann Group Real Estate
$415,000
3 bd
2 ba
1,632 sqft
4269 Summertree Dr,
Tallahassee, FL 32311
The Naumann Group Real Estate
0.51 ACRES
$425,000
3 bd
3 ba
2,203 sqft
5418 Lawton Ct,
Tallahassee, FL 32317
Keller Williams Town & Country
$275,000
3 bd
3 ba
2,139 sqft
2170 Dellwood Dr #C,
Tallahassee, FL 32303
Xcellence
OPEN SAT, 12-3PM
0.35 ACRES
$489,000
4 bd
2.5 ba
2,300 sqft
2210 WALL STREET,
Tallahassee, FL 32309
LISTED SIMPLY
0.6 ACRES
$435,000
4 bd
2.5 ba
1,925 sqft
2609 Raymond Diehl Rd,
Tallahassee, FL 32309
Xcellence
$315,000
3 bd
2 ba
1,462 sqft
2281 Wabash Trl,
Tallahassee, FL 32303
The Naumann Group Real Estate
$499,900
6 bd
6 ba
3,040 sqft
1405 Deerhaven Ln #1,
Tallahassee, FL 32303
The Naumann Group Real Estate
0.35 ACRES
$335,000
3 bd
2 ba
1,581 sqft
1436 Oldfield Dr,
Tallahassee, FL 32308
Kent Strauss Mgt & Real Estate
0.48 ACRES
$324,900
3 bd
2 ba
1,815 sqft
3257 Lord Murphy Trl,
Tallahassee, FL 32309
The Naumann Group Real Estate
NEW - 1 DAY AGO
0.49 ACRES
$389,000
3 bd
2 ba
1,740 sqft
4034 Delvin Dr,
Tallahassee, FL 32309
Coldwell Banker Hartung
0.39 ACRES
$315,000
3 bd
2 ba
1,220 sqft
230 Glenbrook Dr,
Tallahassee, FL 32317
FlatFee.com
$194,900
4 bd
2 ba
1,167 sqft
322 Meadowbrook Ln,
Tallahassee, FL 32304
Lohman Realty LLC
1.83 ACRES
$245,000
3 bd
2 ba
1,680 sqft
8018 Goodwin Dr,
Tallahassee, FL 32311
All Realty Services
0.56 ACRES
$499,900
4 bd
2.5 ba
2,275 sqft
4716 Tory Sound Ln,
Tallahassee, FL 32309
Twin Action Realty Inc.
$485,000
5 bd
3 ba
2,830 sqft
1003 Maple Dr,
Tallahassee, FL 32301
Keller Williams Town & Country
$224,900
3 bd
2.5 ba
1,705 sqft
1575 Paul Russell Rd #501,
Tallahassee, FL 32301
The Naumann Group Real Estate
$185,000
2 bd
1.5 ba
1,441 sqft
3036 Blair Stone Ct,
Tallahassee, FL 32301
Realty One Group Next Gen
$310,000
2 bd
2 ba
1,254 sqft
1358 Pawnee Pointe Ct,
Tallahassee, FL 32312
Keller Williams Town & Country
See more homes for sale in
Monticello
Take a look

Skip to first item

New Listings near 4081 Gamble Rd

Skip to last item

4.89 ACRES
$429,000
3 bd
2 ba
2,000 sqft
285 Mallard Ln,
Monticello, FL 32344
Red Bird Realty
1.56 ACRES
$275,000
3 bd
1 ba
1,948 sqft
11343 Eva Ln,
Tallahassee, FL 32317
Keller Williams Town & Country
FOR SALE BY OWNER
1.25 ACRES
$200,000
4 bd
2 ba
1,605 sqft
12506 Forest Acres Trl,
Tallahassee, FL 32317
2.53 ACRES
$229,900
3 bd
2 ba
1,620 sqft
16985 Chucks Pl W,
Tallahassee, FL 32309
Coldwell Banker Hartung
FOR SALE BY OWNER
11 ACRES
$445,000
3 bd
2 ba
1,720 sqft
153 Watermill Rd,
MONTICELLO, FL 32344
5.5 ACRES
$259,900
3 bd
2 ba
1,456 sqft
1164 Oaklands Plantation Rd,
Monticello, FL 32344
Norris Bishop Realty, LLC
5 ACRES
$254,999
3 bd
2 ba
1,664 sqft
196 Private Rd,
Monticello, FL 32344
OaksFeather Realty
56.37 ACRES
$495,000
2 bd
1 ba
1,200 sqft
640 Nautilus Dr,
Monticello, FL 32344
Kelly & Kelly Properties, Inc
NEW CONSTRUCTION
$425,000
3 bd
2.5 ba
2,169 sqft
933 Cap Tram Rd,
Tallahassee, FL 32317
Hamilton Realty Advisors LLC
33.26 ACRES
$425,000
E Cavallo Trl,
Monticello, FL 32344
Kelly & Kelly Properties, Inc
5.03 ACRES
$199,000
Tbd W Washington,
Monticello, FL 32344
Kelly & Kelly Properties, Inc
See more homes for sale in
Monticello
Take a look

Skip to first item

Property Tax and Assessment

Year	2025
Tax	$2,879
Assessment	$189,440

Home facts updated by county records

Comparable Sales for 4081 Gamble Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
185 Omega Dr, Monticello, FL	0.87	Single-Family Home	$590,000	04/17/26	3	3	3,062
40 W Cavallo Trl, Monticello, FL	1.33	Single-Family Home	$425,000	04/14/26	5	2	2,324
64 Sanctuary Dr, Monticello, FL	1.05	Single-Family Home	$555,000	07/15/26	4	2	1,945
57 Sanctuary Dr, Monticello, FL	0.98	Single-Family Home	$569,000	11/21/25	3	2	1,976
1291 Hayfield Spur Rd, Monticello, FL	1.33	Single-Family Home	$425,000	08/08/25	2	2	1,452
965 Robert Thompson Rd, Monticello, FL	1.66	Single-Family Home	$515,000	05/29/26	4	2	1,838

Nearby homes

Get a sense of prices in the area by checking nearby homes.

Skip to last item

OFF MARKET
245 Whippoorwill Rd #0,
Monticello, FL 32344
Coldwell Banker Hartung
OFF MARKET
Springfield Rd,
Monticello, FL 32344
The Naumann Group Real Estate
OFF MARKET
Est. $453,400
3 bd
2 ba
1,957 sqft
251 N Post Oak Cir,
Lloyd, FL 32344
Capital City Real Estate Group
OFF MARKET
Est. $398,900
3 bd
2 ba
1,564 sqft
299 N Post Oak Dr,
Monticello, FL 32344
Capital City Real Estate Group
SOLD
JUN 30, 2026
$273,000
3 bd
2 ba
1,512 sqft
217 Whitehouse Rd,
Monticello, FL 32344
Kelly & Kelly Properties, Inc
OFF MARKET
Est. $522,100
4 bd
3 ba
2,072 sqft
198 N Post Oak Cir,
Lloyd, FL 32344
Capital City Real Estate Group
OFF MARKET
Est. $408,600
4 bd
2 ba
1,790 sqft
333 N Post Oak Cir,
Lloyd, FL 32344
Capital City Real Estate Group
OFF MARKET
Est. $434,800
3 bd
2 ba
1,616 sqft
231 N White Oak Dr,
Monticello, FL 32344
Ketcham Realty Group, Inc.
OFF MARKET
Est. $411,600
4 bd
2 ba
1,802 sqft
286 N White Oak Dr,
Lloyd, FL 32344
Capital City Real Estate Group
OFF MARKET
Est. $416,500
3 bd
2 ba
1,564 sqft
203 N White Oak Dr,
Lloyd, FL 32344
Capital City Real Estate Group
OFF MARKET
Est. $383,900
3 bd
2 ba
1,564 sqft
314 N White Oak Dr,
Lloyd, FL 32344
Capital City Real Estate Group
OFF MARKET
Est. $460,800
4 bd
2 ba
1,753 sqft
202 Whiteoak Dr N,
Monticello, FL 32344
Coldwell Banker Hartung

Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 4081 Gamble Rd.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Monticello

At least 17 Trulia users voted on each feature.

100 % Say yards are well-kept
91 % Say parking is easy
85 % Say car is needed
73 % Say kids play outside
73 % Say it's quiet
71 % Say people would walk alone at night
67 % Say there's holiday spirit
65 % Say there's wildlife
60 % Say it's dog friendly
59 % Say they plan to stay for at least 5 years
57 % Say streets are well-lit
56 % Say it's walkable to grocery stores
51 % Say neighbors are friendly
50 % Say it's walkable to restaurants
39 % Say there are sidewalks
31 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Trulia User
Resident
1y ago
"All animals are welcome.everyone has dogs, cats, horses,cows and sheep’s. Very lovely neighborhood and neighbors."
0
Flag
Chris S.
Resident
6y ago
"Very good community. That cares about their county. It’s a good commuters town for several counties. "
0
Flag
Hatorgus48
Resident
6y ago
"No traffic lights in the county. City of Monticello is very walkable. A number of very good and eclectic restaurants in town. "
0
Flag
Bridget A.
Resident
7y ago
"I’ve worked in this town since the end of 2003. We finally were able to relocate here about 9 months ago. It’s a lovely little town with lots going for it. Lovely little shops, restaurant, farmers market, art gallery and an opera house."
1
Flag
Manypalms
Resident
7y ago
"My area is beautiful , away from hustle and bustle! Lots are large with room for outdoor activities! Neighbors are nice too! "
0
Flag
estates2us
13y ago
"This area does not have much in the way of nigiht life. It is a good area to retire in. You have to drive into Thomasville to find stores and restaurants in abundance. It is average in looks for an older neighborhood. There is not much to do here."
0
Flag

LGBTQ Local Legal Protections

Alisa McMahon, Bluewater Realty Group

Agent Phone: (850) 510-3961

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

4081 Gamble Rd, Monticello, FL 32344 is a 4 bedroom, 2 bathroom, 2,162 sqft single-family home built in 2005. This property is currently available for sale and was listed by TBR on Jul 16, 2026. The MLS # for this home is MLS# 402551.

4081 Gamble Rd Monticello, FL 32344

$337,000

$337,000

Home Highlights

Local Information

About this House

Home Details for 4081 Gamble Rd

Interior Features

Exterior Features

Days on Market

Property Information

Price & Status

Active Status

Location

Agent Information

Building

HOA

Lot Information

Offer

Miscellaneous

Additional Information

Market trends in Monticello

Price History for 4081 Gamble Rd

Similar Homes You May Like

New Listings near 4081 Gamble Rd

Property Tax and Assessment

Comparable Sales for 4081 Gamble Rd

Nearby homes

Additional Cost

Assigned Schools

What Locals Say about Monticello

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

4081 Gamble Rd
Monticello, FL 32344