4,185

Headland, AL Homes

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  • /80

    $549,900

    • 3 Beds
    • 2.5 Baths
    • 2,549 Sq Ft

    200 Weeping Willow Trail, Headland, AL 36345

    This beautiful 2,549 SF home offers 3 bedrooms, 2.5 baths and an impressive combination of indoor and outdoor living on 1.78 acres. A welcoming covered front porch opens to a bright interior with wood flooring, a separate dining room and a spacious living area featuring vaulted ceilings and an open, split bedroom layout. The kitchen overlooks the living space and offers abundant cabinetry,

    Agent Photo

    Headland Home Team

    Berkshire Hathaway HomeServices Showcase Properties

    200 Weeping Willow Trail, Headland, AL 36345
  • /33

    $1,100 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,225 Sq Ft
    • House for Rent

    202 A B Cotton Dr, Headland, AL 36345

    Property Id: 2864315 Fully remodeled home with all new fixtures, and appliances. Freshly painted interior. Fully fenced yard for outside pet. Located close to middle school and recreation park. Easy access to Hwy 431 to Dothan or Abbeville. Quiet and quaint subdivision away from the hustle and bustle.

    202 A B Cotton Dr, Headland, AL 36345
  • /35

    $267,000

    Sold May 26, 2026

    106 Cabrio Way, Headland, AL 36345

    • 3 Beds
    • 2 Baths
    • 1,662 Sq Ft
    • Built 2020

    Last Sold Summary

    • 5% Below List Price
    • $161/SF
    • 85 Days On Market

    Current Estimated Value $268,688

    Last Listing Agent Mimi Jones Keller Williams Southeast Alabama

    106 Cabrio Way, Headland, AL 36345
    • /50

      Est $287,045

      Not Listed For Sale

      222 Weeping Willow Trail, Headland, AL 36345

      • 3 Beds
      • 2 Baths
      • 1,625 Sq Ft
      • Built 2010
      222 Weeping Willow Trail, Headland, AL 36345

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Lane Blanford Wiregrass Home Team

  • /50

    $244,500

    $8K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,727 Sq Ft

    108 Melissa Ln, Headland, AL 36345

    Welcome home to this charming three-bedroom, two-bath retreat in Headland, where comfort, functionality, and outdoor beauty come together seamlessly. From the moment you arrive, you're greeted by a welcoming covered front porch, perfect for morning coffee or relaxing evenings. Step inside to a spacious living room featuring a vaulted ceiling, cozy wood-burning fireplace, and custom built-in

    Agent Photo

    Headland Home Team

    Berkshire Hathaway HomeServices Showcase Properties

    108 Melissa Ln, Headland, AL 36345
  • /12

    $1,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • House for Rent

    8 Carlock St, Headland, AL 36345

    Brand new construction in Headland. 2 bedroom, 2 bath, Ref, Gas Stove, Gas Heat, Central Air and small pets considered. For more information please contact Real Estate Services of Dothan

    Kendra Pope Real Estate Services Of Dothan

    8 Carlock St, Headland, AL 36345
  • /52

    $385,000

    Sold Apr 23, 2026

    264 Weeping Willow Trail, Headland, AL 36345

    • 4 Beds
    • 3 Baths
    • 2,672 Sq Ft
    • Built 2022

    Last Sold Summary

    • $144/SF
    • 321 Days On Market

    Last Listing Agent Headland Home Team Berkshire Hathaway HomeServices Showcase Properties

    264 Weeping Willow Trail, Headland, AL 36345
    • /44

      Est $347,065

      Not Listed For Sale

      201 Azalea Ln, Headland, AL 36345

      • 4 Beds
      • 2 Baths
      • 2,134 Sq Ft
      • Built 2010
      201 Azalea Ln, Headland, AL 36345

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Danita Murdoch Berkshire Hathaway HomeServices Showcase Properties

  • /17

    $28,900

    • Land
    • 15,681 Sq Ft
    • $80,278 per Acre

    Lot 3 Block A Eagles View, Headland, AL 36345

    Builder Ready Lots in the Willow Walk Subdivision. Enjoy all the amenities of Willow Walk. Walking trails, party pavilion and stocked ponds. Located in the Headland School District and a minute from the Headland Country Club and Golf Course off of County Rd 49.

    Agent Photo

    Headland Home Team

    Berkshire Hathaway HomeServices Showcase Properties

    Lot 3 Block A Eagles View, Headland, AL 36345
  • /2

    $1,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,419 Sq Ft
    • Oates 1

    202 Oates St, Headland, AL 36345

    2 bedroom 2 full bath

    202 Oates St, Headland, AL 36345
  • /29

    $355,000

    Sold Aug 19, 2026

    108 Stonegate Rd, Headland, AL 36345

    • 4 Beds
    • 2.5 Baths
    • 2,380 Sq Ft
    • Built 1996

    Last Sold Summary

    • 1% Below List Price
    • $149/SF
    • 43 Days On Market

    Current Estimated Value $352,584

    Last Listing Agent Rosemary Howell Executive Brokers Group

    108 Stonegate Rd, Headland, AL 36345
    • /28

      Est $184,871

      Not Listed For Sale

      403 S Main St, Headland, AL 36345

      • 3 Beds
      • 2 Baths
      • 1,596 Sq Ft
      • Built 1935
      403 S Main St, Headland, AL 36345

      Last Sold Summary

      • 188 Days On Market

      Last Listing Agent Clear To Close Group JW Grant Realty

  • /2

    $58,000

    • Land
    • 3 Acres
    • $19,333 per Acre

    0 County Road 576, Headland, AL 36345

    3.05 Acres for sale. 1800 Min SF Barndominium or Single family home. No mobile homes.

    Agent Photo

    Dwayne Bowman

    Weichert Realtors JBR Legacy Group

    0 County Road 576, Headland, AL 36345
  • /6

    $1,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    10 Whitten St, Headland, AL 36345

    3/2 Duplex in Headland. For more information please contact Real Estate Services of Dothan. Unit A is Available

    Kendra Pope Real Estate Services Of Dothan

    10 Whitten St, Headland, AL 36345
  • /53

    $605,000

    Sold Dec 12, 2025

    390 County Road 11, Headland, AL 36345

    • 4 Beds
    • 3.5 Baths
    • 3,089 Sq Ft
    • Built 2024

    Last Sold Summary

    • $196/SF
    • 156 Days On Market

    Last Listing Agent Lisa Mitchell-Mock JW Grant Realty

    390 County Road 11, Headland, AL 36345
    • /16

      Est $103,517

      Not Listed For Sale

      178 County Road 250, Headland, AL 36345

      • 3 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1969
      178 County Road 250, Headland, AL 36345

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Darcy Peoples At Home Realty Services, LLC

  • /17

    $28,900

    • Land
    • 27,007 Sq Ft
    • $46,613 per Acre

    Lot 15 Block A Eagles View, Headland, AL 36345

    Builder Ready Lots in the Willow Walk Subdivision. Enjoy all the amenities of Willow Walk. Walking trails, party pavilion and stocked ponds. Located in the Headland School District and a minute from the Headland Country Club and Golf Course off of County Rd 49.

    Agent Photo

    Headland Home Team

    Berkshire Hathaway HomeServices Showcase Properties

    Lot 15 Block A Eagles View, Headland, AL 36345
  • /12

    $1,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • House for Rent

    10 Carlock St, Headland, AL 36345

    Brand new construction. 2/2, CH/A, Ref, Gas Stove, Gas Heat, Central Air, Please contact Real Estate Services of Dothan.

    Kendra Pope Real Estate Services Of Dothan

    10 Carlock St, Headland, AL 36345
  • /24

    $121,900

    Sold Apr 07, 2026

    445 Bartlett Loop, Headland, AL 36345

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 2013

    Last Sold Summary

    • $68/SF
    • 179 Days On Market

    Last Listing Agent Darcy Peoples At Home Realty Services, LLC

    445 Bartlett Loop, Headland, AL 36345
    • /35

      Est $352,204

      Not Listed For Sale

      4297 E County Road 22, Headland, AL 36345

      • 3 Beds
      • 2 Baths
      • 2,010 Sq Ft
      • Built 1991
      4297 E County Road 22, Headland, AL 36345

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Tesi Conte-Rodriguez Berkshire Hathaway HomeServices Showcase Properties

  • /17

    $28,900

    • Land
    • 18,295 Sq Ft
    • $68,810 per Acre

    Lot 21 1st Add Weeping Willow Trail, Headland, AL 36345

    Builder Ready Lots in the Willow Walk Subdivision. Enjoy all the amenities of Willow Walk. Walking trails, party pavilion and stocked ponds. Located in the Headland School District and a minute from the Headland Country Club and Golf Course off of County Rd 49.

    Agent Photo

    Headland Home Team

    Berkshire Hathaway HomeServices Showcase Properties

    Lot 21 1st Add Weeping Willow Trail, Headland, AL 36345
  • /55

    $419,900

    Sold Jul 29, 2026

    125 Tanglewood Dr, Headland, AL 36345

    • 4 Beds
    • 3 Baths
    • 2,725 Sq Ft
    • Built 2019

    Last Sold Summary

    • 2% Below List Price
    • $154/SF
    • 83 Days On Market

    Current Estimated Value $503,330

    Last Listing Agent Cristi Dean Keller Williams Southeast Alabama

    125 Tanglewood Dr, Headland, AL 36345
    • /48

      Est $380,115

      Not Listed For Sale

      335 County Road 15, Headland, AL 36345

      • 3 Beds
      • 2.5 Baths
      • 2,914 Sq Ft
      • Built 1978
      335 County Road 15, Headland, AL 36345

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Carol Finley Tom West Company, Inc.

  • /2

    $58,000

    • Land
    • 3 Acres
    • $19,333 per Acre

    Lot 2 County Road 576, Headland, AL 36345

    3.00 Acres for sale. 1800 Min SF Barndominium or Single family home. No mobile homes.

    Agent Photo

    Dwayne Bowman

    Weichert Realtors JBR Legacy Group

    Lot 2 County Road 576, Headland, AL 36345
  • /2

    $45,000

    Sold Apr 02, 2026

    Lot 1 County Road 576, Headland, AL 36345

    • Land
    • 3.05 Acres
    • $14,754 per Acre

    Last Sold Summary

    • 346 Days On Market

    Last Listing Agent Dwayne Bowman Weichert Realtors JBR Legacy Group

    Lot 1 County Road 576, Headland, AL 36345
    • /43

      Est $288,354

      Not Listed For Sale

      4106 County Road 49, Headland, AL 36345

      • 3 Beds
      • 2 Baths
      • 1,570 Sq Ft
      • Built 2007
      4106 County Road 49, Headland, AL 36345

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Misti Caddell Keller Williams Southeast Alabama

  • /17

    $28,900

    • Land
    • 17,859 Sq Ft
    • $70,488 per Acre

    Lot 8 Block D Weeping Willow Trail, Headland, AL 36345

    Builder Ready Lots in the Willow Walk Subdivision. Enjoy all the amenities of Willow Walk. Walking trails, party pavilion and stocked ponds. Located in the Headland School District and a minute from the Headland Country Club and Golf Course off of County Rd 49.

    Agent Photo

    Headland Home Team

    Berkshire Hathaway HomeServices Showcase Properties

    Lot 8 Block D Weeping Willow Trail, Headland, AL 36345
  • /3

    $55,000

    Sold Apr 22, 2026

    Lot 5 Gilley Mill Rd, Headland, AL 36345

    • Land
    • 7.69 Acres
    • $7,152 per Acre

    Last Sold Summary

    • 358 Days On Market

    Last Listing Agent Andy Johns Lan Darty Real Estate & Development

    Lot 5 Gilley Mill Rd, Headland, AL 36345
    • /47

      Est $361,192

      Not Listed For Sale

      274 County Road 263, Headland, AL 36345

      • 3 Beds
      • 2 Baths
      • 2,475 Sq Ft
      • Built 2003
      274 County Road 263, Headland, AL 36345

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent John Baker BAKER REALTY, INC.

  • /17

    $28,900

    • Land
    • 14,810 Sq Ft
    • $85,000 per Acre

    Lot 7 Block E Weeping Willow Trail, Headland, AL 36345

    Builder Ready Lots in the Willow Walk Subdivision. Enjoy all the amenities of Willow Walk. Walking trails, party pavilion and stocked ponds. Located in the Headland School District and a minute from the Headland Country Club and Golf Course off of County Rd 49.

    Agent Photo

    Headland Home Team

    Berkshire Hathaway HomeServices Showcase Properties

    Lot 7 Block E Weeping Willow Trail, Headland, AL 36345
  • /33

    $350,000

    Sold Jan 16, 2026

    1532 County Road 20, Headland, AL 36345

    • 4 Beds
    • 2 Baths
    • 1,978 Sq Ft
    • Built 2022

    Last Sold Summary

    • $177/SF
    • 22 Days On Market

    Last Listing Agent Carol Peak Keller Williams Southeast Alabama

    1532 County Road 20, Headland, AL 36345
    • /44

      Est $327,003

      Not Listed For Sale

      1256 County Road 11, Headland, AL 36345

      • 3 Beds
      • 2.5 Baths
      • 3,200 Sq Ft
      • Built 1972
      1256 County Road 11, Headland, AL 36345

      Last Sold Summary

      • 79 Days On Market

      Last Listing Agent Kelly Woodham Forrest & Fields, Inc.

  • /17

    $28,900

    • Land
    • 14,810 Sq Ft
    • $85,000 per Acre

    Lot 6 Block D Weeping Willow Trail, Headland, AL 36345

    Builder Ready Lots in the Willow Walk Subdivision. Enjoy all the amenities of Willow Walk. Walking trails, party pavilion and stocked ponds. Located in the Headland School District and a minute from the Headland Country Club and Golf Course off of County Rd 49.

    Agent Photo

    Headland Home Team

    Berkshire Hathaway HomeServices Showcase Properties

    Lot 6 Block D Weeping Willow Trail, Headland, AL 36345
  • /11

    $80,000

    Sold Apr 30, 2026

    13 & 15 Broad St, Headland, AL 36345

    • Land
    • 1.16 Acres
    • $68,966 per Acre

    Last Sold Summary

    • 156 Days On Market

    Last Listing Agent Elisha Hollis Keller Williams Southeast Alabama

    13 & 15 Broad St, Headland, AL 36345
    • /42

      Est $315,753

      Not Listed For Sale

      118 Willow Oaks Dr, Headland, AL 36345

      • 3 Beds
      • 2 Baths
      • 1,812 Sq Ft
      • Built 1999
      118 Willow Oaks Dr, Headland, AL 36345

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Kelli Cundith Coldwell Banker/Alfred Saliba

  • /17

    $28,900

    • Land
    • 16,552 Sq Ft
    • $76,053 per Acre

    Lot 17 Block A Eagles View, Headland, AL 36345

    Builder Ready Lots in the Willow Walk Subdivision. Enjoy all the amenities of Willow Walk. Walking trails, party pavilion and stocked ponds. Located in the Headland School District and a minute from the Headland Country Club and Golf Course off of County Rd 49.

    Agent Photo

    Headland Home Team

    Berkshire Hathaway HomeServices Showcase Properties

    Lot 17 Block A Eagles View, Headland, AL 36345
  • /24

    $242,400

    Sold Jan 29, 2026

    113 Aubrey Ave, Headland, AL 36345

    • 3 Beds
    • 2 Baths
    • 1,618 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $150/SF
    • 26 Days On Market

    D.R. Horton Sagebrush

    113 Aubrey Ave, Headland, AL 36345
    • /60

      Est $195,547

      Not Listed For Sale

      115 Armstrong St, Headland, AL 36345

      • 3 Beds
      • 1.5 Baths
      • 1,462 Sq Ft
      • Built 1974
      115 Armstrong St, Headland, AL 36345

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Elisha Hollis JW Grant Realty

  • /45

    $360,000

    $35K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,030 Sq Ft

    107 Forrest St, Headland, AL 36345

    Step into a little piece of Headland history, thoughtfully renovated 1948 built home to preserve its timeless character while incorporating modern updates throughout. This distinctive 5-bedroom, 3-bath home sits on approximately 0.40 acres and includes a pool house apartment and a private in-ground pool added in 2023, creating a truly versatile property. Exterior improvements have been carefully

    Agent Photo

    Bridgett Hooks

    Wiregrass Home Team Enterprise

    107 Forrest St, Headland, AL 36345
  • /11

    $100,000

    Sold Jan 05, 2026

    409 Peachtree St, Headland, AL 36345

    • 3 Beds
    • 1.5 Baths
    • 1,559 Sq Ft
    • Built 1960

    Last Sold Summary

    • $64/SF
    • 11 Days On Market

    Current Estimated Value $198,335

    Last Listing Agent David Ridley EXP Realty LLC

    409 Peachtree St, Headland, AL 36345

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$291,329
Median Single Family Sale Price
$307,500
Median 2 Bedroom Sale Price
$160,000
Average Price Per Sq Ft
$155
Number of Homes for Sale
4,185
Last 12 months Home Sales
157
Months of Supply
4.70
Median List Price
$314,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
9%
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