Madison County, FL Homes

/60
$125,000
- 2 Beds
- 2 Baths
- 1,369 Sq Ft
863 NW Whippoorwill Dr, Greenville, FL 32331

SELLER MOTIVATED! Peaceful Country Retreat on Whippoorwill Way – This well-kept 2009 2 bedroom / 2 bathroom single-wide (16' x 76') offers a comfortable and serene setting along a quiet country lane between Monticello and Greenville in Madison County, Florida. The home features a large master ensuite, huge walk-in closet, and convenient washer/dryer hookup inside. The property includes well,

Lynette Sirmon

All Realty Services

(448) 217-3393

863 NW Whippoorwill Dr, Greenville, FL 32331
/38
$85,000 Sold Apr 17, 2025

969 NE Persimmon Dr, Pinetta, FL 32350
- 1 Bed
- 2 Baths
- 896 Sq Ft
- Built 1989
Last Sold Summary
- 13% Below List Price
- $95/SF
- 43 Days On Market
Last Listing Agent Dee Leslie OaksFeather Realty

969 NE Persimmon Dr, Pinetta, FL 32350

/17
Not Listed For Sale
Lot 87 SW Oregon Trail, Greenville, FL 32331

Lot 87 SW Oregon Trail, Greenville, FL 32331

/58
$335,000 Pending
- 3 Beds
- 2 Baths
- 1,920 Sq Ft
529 NE Evergreen Ave, Pinetta, FL 32350

North Florida country Living with room to roam – 11.83 acres with pond Enjoy peace, privacy, and the beauty of nature in this brick, 3-bedroom, 2-bath home on 11.83 acres in the heart of North Florida's countryside. With 1,920 sqft of comfortable living space, this property offers the perfect balance of rural charm and modern convenience. The sunroom provides a serene view of the pond—perfect for

Scarlett Holt

The American Dream

(448) 428-5981

529 NE Evergreen Ave, Pinetta, FL 32350
/42
$45,000 Sold Feb 18, 2025

Vacant SE Midway Church Rd, Lee, FL 32059
- Land
- 5.01 Acres
- $8,982 per Acre
Last Sold Summary
- 1 Day On Market
Last Listing Agent Jerrod Trainer Jerrod A Trainer & Associates

Vacant SE Midway Church Rd, Lee, FL 32059

/36
Not Listed For Sale
Vacant NE River Country Trail, Madison County, FL 32059

Vacant NE River Country Trail, Madison County, FL 32059

/70
$588,500
- 5 Beds
- 6 Baths
- 3,814 Sq Ft
588 NW Pickle Ln, Madison, FL 32340

This spacious 5-bedroom, 6-bath brick home—priced below appraisal— sits on 5 beautiful acres surrounded by peace and privacy. Offering two stories plus a heated and cooled basement, the home features a remodeled kitchen with stainless steel appliances, a full-size oven, and granite countertops. Flooring throughout includes hardwood, parquet, and slate. Enjoy multiple living spaces including a

Dennis L Coxwell Keller Williams Town & Country

588 NW Pickle Ln, Madison, FL 32340
/29
$61,500 Sold Feb 10, 2025

284 SW Paradise Way, Greenville, FL 32331
- Land
- 10.93 Acres
- $5,627 per Acre
Last Sold Summary
- 5% Below List Price
- 74 Days On Market
Current Estimated Value $60,923

Last Listing Agent Andrea White Sawgrass Realty, LLC

284 SW Paradise Way, Greenville, FL 32331

/4
Not Listed For Sale
Vacant SW Worthington Trail, Greenville, FL 32331

Vacant SW Worthington Trail, Greenville, FL 32331

/2
$270,000
- Land
- 40.02 Acres
- $6,747 per Acre
0 SE Pebble Ridge St Unit 23525783, Lee, FL 32059

This 40-acre property is part of Glenwood Forest. It includes 12 acres of pines that are over 20 years old, while the remaining 28 acres were planted less than a year ago. This land is a blank canvas, offering endless possibilities for your imagination. Manufactured homes are permitted. It is located on a county-maintained road and is surrounded by other large parcels of land.

TINA DONALDSON Tina Donaldson with AFG Tristate Realty

0 SE Pebble Ridge St Unit 23525783, Lee, FL 32059
/44
$285,000 Sold Sep 05, 2025

405 NW Whispering Pines Loop, Madison, FL 32340
- 3 Beds
- 2 Baths
- 1,849 Sq Ft
- Built 1979
Last Sold Summary
- 11% Below List Price
- $154/SF
- 20 Days On Market
Current Estimated Value $305,453

Last Listing Agent Jessica Groover Southern Land & Homes

405 NW Whispering Pines Loop, Madison, FL 32340

/12
Not Listed For Sale
Vacant SE Baldwin Dr, Lee, FL 32059

Vacant SE Baldwin Dr, Lee, FL 32059

/18
$150,000
- Land
- 30.68 Acres
- $4,889 per Acre
0 Vacant Sw Jeanette Cir, Madison, FL 32340

30.68 Acres of Prime Vacant Land in Madison - Ideal for Investment or Development! Parcels 28-1N-09-5083-000-000 & 28-1N-09-5083-001-000This 30.68-acre parcel offers a fantastic opportunity for investors and developers in a highly sought-after location. Situated within the city limits of Madison, this property is surrounded by land owned by the City of Madison, offering both privacy and

Jessica Groover Southern Land & Homes

0 Vacant Sw Jeanette Cir, Madison, FL 32340
/2
$107,000 Sold Sep 02, 2025

746 NE Pentas St, Madison, FL 32340
- 2 Beds
- 1 Bath
- 720 Sq Ft
- Built 1979
Last Sold Summary
- 11% Below List Price
- $149/SF
- 29 Days On Market
Last Listing Agent Lou Thurmond THURMOND REALTY LLC

746 NE Pentas St, Madison, FL 32340

/17
Not Listed For Sale
Vacant NE Rocky Ford Rd, Madison County, FL 32340

Vacant NE Rocky Ford Rd, Madison County, FL 32340

/19
$562,800
- Land
- 268 Acres
- $2,100 per Acre
0 County Line Rd Unit 19604811, Lee, FL 32059

268 acres in the middle of over 600,000 acres of timberlands and private land owners. The watering holes and surrounding woods create an idyllic habitat for a wide variety of wildlife. Sit in your stand and look in awe as deer, turkeys, and more make their home in these woods. The roads have been recently mowed and repaired. Walk across the road on the southwest corner and you will be in

TINA DONALDSON Tina Donaldson with AFG Tristate Realty

0 County Line Rd Unit 19604811, Lee, FL 32059
/65
$335,000 Sold Oct 24, 2025

80 acres SW Delray Ave, Greenville, FL 32331
- Land
- 80 Acres
- $4,188 per Acre
Last Sold Summary
- 16% Below List Price
- 58 Days On Market
Last Listing Agent Andrea White Sawgrass Realty, LLC

80 acres SW Delray Ave, Greenville, FL 32331

/6
Est $349,167 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,006 Sq Ft
3473 NE Oak Hill Rd, Pinetta, FL 32350

3473 NE Oak Hill Rd, Pinetta, FL 32350

/16
$214,200
- Land
- 102 Acres
- $2,100 per Acre
0 SW Brown Rd, Lee, FL 32059

102 acres sectioned from a larger parcel in the middle of over 600,000 acres of timberlands and private land owners. Deer, turkey and hogs are in abundance in this area. This parcel of land is situated where Madison, Lafayette and Taylor county all meet. No HOA or deed restrictions. Electric is more than 5 miles away so bring those generators or solar panels to enjoy hunting at its best!

TINA DONALDSON Tina Donaldson with AFG Tristate Realty

0 SW Brown Rd, Lee, FL 32059
/18
$60,000 Sold Nov 14, 2025

Lot 5 SW Wakulla Way, Greenville, FL 32331
- Land
- 7.07 Acres
- $8,487 per Acre
Last Sold Summary
- 10% Below List Price
- 22 Days On Market
Last Listing Agent Benjamin Sadler OaksFeather Realty

Lot 5 SW Wakulla Way, Greenville, FL 32331

/35
Est $427,044 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,901 Sq Ft
4109 NE Cattail Dr, Lee, FL 32059

4109 NE Cattail Dr, Lee, FL 32059

/25
$300,000
- Land
- 12.77 Acres
- $23,493 per Acre
1420 S State Road 53, Madison, FL 32340

Madison Commercial 13 is ready for business. Located on SR 53 8/10 of a mile south of downtown Madison, Florida. The property boasts 512' of highway frontage on SR 53 and is conveniently located to both downtown Madison and Interstate 10. The site has an abandoned railroad spur that has the possibility of being connected to the Gulf Atlantic Railroad. This is a prime commercial site suited for

Greg Driskell Saunders Land

1420 S State Road 53, Madison, FL 32340
/2
$165,000 Sold Oct 31, 2025

2604 SE Donaldson Rd, Lee, FL 32059
- Land
- 20 Acres
- $8,250 per Acre
Last Sold Summary
- 11% Below List Price
- 89 Days On Market
Last Listing Agent Ronald Carver UNITED COUNTRY SMITH & ASSOCIATES - NEWBERRY

2604 SE Donaldson Rd, Lee, FL 32059

/36
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,782 Sq Ft
539 NW Dennet Pond Way, Greenville, FL 32331

539 NW Dennet Pond Way, Greenville, FL 32331

/54
$699,000
- Land
- 45.05 Acres
- $15,516 per Acre
3859 SE Cr 255, Lee, FL 32059

This property consists of 45.05 acres of pasture land featuring large pecan trees. The entire area is fully fenced and cross-fenced. It includes a 961-square-foot home with an in-ground pool, as well as two RV hook-ups. Additionally, there is a horse barn with a tack room, a large workshop located at the back of the property, and an all-purpose building measuring 100 by 20 feet in the front

TINA DONALDSON Tina Donaldson with AFG Tristate Realty

3859 SE Cr 255, Lee, FL 32059
/42
$346,500 Sold Jul 23, 2025

181 NE Biltmore Rd, Madison, FL 32340
- 4 Beds
- 3 Baths
- 2,028 Sq Ft
- Built 1991
Last Sold Summary
- 5% Below List Price
- $171/SF
- 7 Days On Market
Current Estimated Value $354,051

Last Listing Agent Jessica Groover Southern Land & Homes

181 NE Biltmore Rd, Madison, FL 32340

/27
Not Listed For Sale
- 2 Beds
- 2 Baths
- 2,304 Sq Ft
5143 SW Us 221, Greenville, FL 32331

5143 SW Us 221, Greenville, FL 32331

/63
$700,000
- 4 Beds
- 2 Baths
- 2,316 Sq Ft
397 SE Schooner Way, Lee, FL 32059

Take a look at this private, like-new home on 40 acres of long leaf pines in Madison County. The home is totally powered by solar panels, offering sustainable and self-sufficient energy. Enjoy contemporary fixtures, a fully equipped kitchen, ample storage, and all the amenities required for comfortable living. The master suite exudes comfort and relaxation, offering an enormous soaker tub and

Katy Yanossy POOLE REALTY INC.

397 SE Schooner Way, Lee, FL 32059
/33
$130,000 Sold May 31, 2025

Vacant SW Cr 360 Rd, Madison, FL 32340
- Land
- 26.29 Acres
- $4,945 per Acre
Last Sold Summary
- 8 Days On Market
Last Listing Agent Ahmed Ismail Sand Seekers Realty LLC

Vacant SW Cr 360 Rd, Madison, FL 32340

/42
Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,995 Sq Ft
216 SE Ravenswood Way, Madison, FL 32340

216 SE Ravenswood Way, Madison, FL 32340

/53
$123,200
- Land
- 56 Acres
- $2,200 per Acre
0 County Line Rd Unit 18882882, Lee, FL 32059

56 acres located in Madison county, FL in the city of Lee. It is a total of 631 acres and it is being offered in several different sized parcels. This land has abundant wildlife; Deer, Turkey and Hogs. It is connected to over 600,000 acres of timberlands and private land owners. There are no deed restrictions or HOA. You may have a camper or have a metal building. The land is combination of

TINA DONALDSON Tina Donaldson with AFG Tristate Realty

0 County Line Rd Unit 18882882, Lee, FL 32059
/77
$1,600,000 Sold Mar 07, 2025

698 SE Olustee Dr, Lee, FL 32059
- 3 Beds
- 2.5 Baths
- 2,663 Sq Ft
- Built 2003
Last Sold Summary
- $601/SF
- 1,225 Days On Market
Current Estimated Value $483,859

Last Listing Agent TINA DONALDSON AFG TRI STATE REALTY, INC

698 SE Olustee Dr, Lee, FL 32059

/33
Not Listed For Sale
00 NE Hillside Terrace, Lee, FL 32059

00 NE Hillside Terrace, Lee, FL 32059

/7
$165,000
- Land
- 75 Acres
- $2,200 per Acre
0 County Line Rd Unit 19597151, Lee, FL 32059

75 acres with exceptional wildlife! In the middle of over 600,000 acres. No HOA and no deed restrictions. Buy this land and create your own hunting camp to your specifications. Madison county is known for its big bucks, it is on the list of top 10 counties for buck registrations. Come snag that prize buck today!

TINA DONALDSON Tina Donaldson with AFG Tristate Realty

0 County Line Rd Unit 19597151, Lee, FL 32059
/27
$275,000 Sold Jul 18, 2025

287 NE Jay St, Madison, FL 32340
- 3 Beds
- 2 Baths
- 2,074 Sq Ft
- Built 1979
Last Sold Summary
- 15% Below List Price
- $133/SF
- 246 Days On Market
Current Estimated Value $292,256

Last Listing Agent Lynette Sirmon All Realty Services

287 NE Jay St, Madison, FL 32340

/29
Est $171,423 Not Listed For Sale
- 2 Beds
- 1 Bath
- 589 Sq Ft
9010 Alton Wentworth Rd, Greenville, FL 32331

9010 Alton Wentworth Rd, Greenville, FL 32331

/69
$3,285,000
- 4 Beds
- 5 Baths
- 5,395 Sq Ft
1706 NW Radford Denson Rd, Greenville, FL 32331

Cypress Hill – 198+/- Acres of Premier Recreational and Luxury Living in Madison County, Florida Welcome to Cypress Hill, a meticulously crafted 198-acre estate designed for both high-end living and exceptional recreation. From the moment you pass through the gate, it’s clear this isn’t just land—it’s a lifestyle. Every detail, from the curated topography to the architectural choices, reflects

Ben Jones Southern Land & Homes

1706 NW Radford Denson Rd, Greenville, FL 32331
/26
$13,000 Sold Nov 12, 2025

*Lot 57* Vacant NE Blackjack Loop Unit 1, Lee, FL 32059
- Land
- 1.03 Acres
- $12,621 per Acre
Last Sold Summary
- 6% Below List Price
- 287 Days On Market
Last Listing Agent Jerrod Trainer Jerrod A Trainer & Associates

*Lot 57* Vacant NE Blackjack Loop Unit 1, Lee, FL 32059

/4
Not Listed For Sale
00 SE Thomas Way, Lee, FL 32059

00 SE Thomas Way, Lee, FL 32059

/11
$87,400
- Land
- 38 Acres
- $2,300 per Acre
0 SW Prine Rd, Lee, FL 32059

Great hunting tract consisting of 38 acres, and an abundance of deer, turkey and hogs roam this property daily. Madison county is known for its big bucks, it is on the list of top 10 counties for typical and non-typical buck scores. Set up your own hunting camp and enjoy the outdoors! 6 miles from electric so bring your generators and camper

TINA DONALDSON Tina Donaldson with AFG Tristate Realty

0 SW Prine Rd, Lee, FL 32059

Showing Results 41 - 80, Page 2 of 18

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