Jessamine County, KY Homes

• 

  

  

  /17

  $481,931

  Sold May 13, 2026

  112 Roland Ct, Nicholasville, KY 40356

  • 4 Beds
  • 3 Baths
  • 2,518 Sq Ft
  • Built 2026

  Last Sold Summary

  • $191/SF
  • 9 Days On Market

  Last Listing Agent James Monroe Buy With Confidence Real Estate

  112 Roland Ct, Nicholasville, KY 40356
• 

  

  

  /22

  Est $303,282

  Not Listed For Sale

  132 Mariwood Dr, Nicholasville, KY 40356

  • 3 Beds
  • 3 Baths
  • 1,814 Sq Ft
  • Built 1997

  132 Mariwood Dr, Nicholasville, KY 40356

  Last Sold Summary

  • 4 Days On Market
• 

  

  /2

  $300,000

  Pending

  • Land
  • 40,075 Sq Ft
  • $326,087 per Acre

  5170 Harrodsburg Rd Unit Lot 39, Nicholasville, KY 40356

  # Cassity Farm - Jessamine County's Newest Luxury Community Discover your dream homesite in Cassity Farm, a prestigious new development nestled less than one mile from the Lexington city limits. This is more than just a lot — it's an invitation to join a thoughtfully planned community where timeless design meets modern convenience. Spanning over 11 acres of planned open space, Cassity Farm

  Jennifer Mooney The Brokerage

  5170 Harrodsburg Rd Unit Lot 39, Nicholasville, KY 40356
• 

  

  

  /46

  $620,000

  Sold Dec 30, 2025

  300 Tashamingo Dr, Nicholasville, KY 40356

  • 4 Beds
  • 3.5 Baths
  • 2,912 Sq Ft
  • Built 1971

  Last Sold Summary

  • 11% Below List Price
  • $213/SF
  • 52 Days On Market

  Current Estimated Value $642,583

  Last Listing Agent Jessica Pike Deborah Ball Realty

  300 Tashamingo Dr, Nicholasville, KY 40356
• 

  

  

  /38

  Est $309,051

  Not Listed For Sale

  308 W Ridge Dr Unit 2A, Nicholasville, KY 40356

  • 3 Beds
  • 2 Baths
  • 1,587 Sq Ft
  • Built 1997

  308 W Ridge Dr Unit 2A, Nicholasville, KY 40356

  Last Sold Summary

  • 2 Days On Market
• 

  

  /31

  $215,000

  • 2 Beds
  • 1.5 Baths
  • 1,294 Sq Ft

  120 Cherrybrook Dr Unit C, Nicholasville, KY 40356

  Beautiful 2BR/2BA townhome in the gated 7-Acre Lake of the Orchard community in Nicholasville. Enjoy low-maintenance living with exceptional amenities including a heated pool, tennis court, walking track, fishing lake, and clubhouse. A wonderful opportunity to enjoy comfort, convenience, and an active lifestyle in a scenic community.

  Catherine Wilson Kentucky Land and Home

  120 Cherrybrook Dr Unit C, Nicholasville, KY 40356
• 

  

  /30

  $319,000

  Sold Jun 18, 2026

  629 Williams Rd, Nicholasville, KY 40356

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft
  • Built 2004

  Last Sold Summary

  • $206/SF

  Current Estimated Value $310,327

  Last Listing Agent Whitney Pannell Team Pannell Real Estate

  629 Williams Rd, Nicholasville, KY 40356
• 

  

  /24

  Est $279,736

  Not Listed For Sale

  305 W Ridge Dr, Nicholasville, KY 40356

  • 3 Beds
  • 2 Baths
  • 1,324 Sq Ft
  • Built 1996

  305 W Ridge Dr, Nicholasville, KY 40356

  Last Sold Summary

  • 20 Days On Market
• 

  /2

  $480,405

  New Construction Pending

  • 5 Beds
  • 3 Baths
  • 2,715 Sq Ft

  267 Gravel Springs Path, Nicholasville, KY 40356

  The Jackson II is a spacious four-bedroom home with a downstairs office/study, which can also be configured as a guest suite. The two-story foyer has a railed overlook above and encompasses a stairway with a feature window over the landing. The family room and breakfast overlook the rear yard, and the centrally located kitchen is open to all main living areas of the home, for good traffic flow

  Jennifer Sisson Christies International Real Estate Bluegrass

  267 Gravel Springs Path, Nicholasville, KY 40356
• 

  /2

  $454,000

  Sold Jul 09, 2025

  114 Cherrywood Dr, Nicholasville, KY 40356

  • 3 Beds
  • 2 Baths
  • 2,008 Sq Ft

  Last Sold Summary

  • 5% Below List Price
  • $226/SF

  Current Estimated Value $467,943

  Last Listing Agent Morgan Withrow The Brokerage

  114 Cherrywood Dr, Nicholasville, KY 40356
• 

  

  /25

  Est $299,884

  Not Listed For Sale

  113 S Town Branch Dr, Nicholasville, KY 40356

  • 3 Beds
  • 2 Baths
  • 1,638 Sq Ft
  • Built 1997

  113 S Town Branch Dr, Nicholasville, KY 40356

  Last Sold Summary

  • 18 Days On Market
• 

  

  /33

  $1,320,000

  • Land
  • 114.25 Acres
  • $11,554 per Acre

  2-A Harrodsburg Rd, Wilmore, KY 40390

  Spanning approximately 114.25+/- acres in the heart of Jessamine County, this exceptional farm offers the perfect blend of beauty, functionality, and convenience. Ideally situated along Harrodsburg Road, the property features multiple fenced pastures, making it well-suited for cattle, horses, or a variety of agricultural uses. The gently rolling landscape is enhanced by picturesque, tree-lined

  Maggie Taylor RE/MAX Creative Realty

  2-A Harrodsburg Rd, Wilmore, KY 40390
• 

  

  /11

  $450,000

  Sold Nov 18, 2025

  264 Grinder Ct Unit 270, Nicholasville, KY 40356

  • 8 Beds
  • 4 Baths
  • 3,700 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $122/SF
  • 8 Days On Market

  Current Estimated Value $461,190

  Last Listing Agent Christina Dudek Coldwell Banker McMahan

  264 Grinder Ct Unit 270, Nicholasville, KY 40356
• 

  

  /18

  Est $277,114

  Not Listed For Sale

  456 Southbrook Dr, Nicholasville, KY 40356

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Built 1994

  456 Southbrook Dr, Nicholasville, KY 40356

  Last Sold Summary

  • 1 Day On Market
• 

  /2

  $250,000

  Pending

  • Land
  • 26,136 Sq Ft
  • $416,667 per Acre

  5170 Harrodsburg Rd Unit Lot 26, Nicholasville, KY 40356

  # Cassity Farm - Jessamine County's Newest Luxury Community Discover your dream homesite in Cassity Farm, a prestigious new development nestled less than one mile from the Lexington city limits. This is more than just a lot -- it's an invitation to join a thoughtfully planned community where timeless design meets modern convenience. Spanning over 11 acres of planned open space, Cassity Farm

  Jennifer Mooney The Brokerage

  5170 Harrodsburg Rd Unit Lot 26, Nicholasville, KY 40356
• 

  /2

  $316,023

  Sold Mar 05, 2026

  208 Pavilion Trail, Nicholasville, KY 40356

  • 3 Beds
  • 2.5 Baths
  • 1,997 Sq Ft
  • Built 2025

  Last Sold Summary

  • $158/SF

  Last Listing Agent Rob Bolton Christies International Real Estate Bluegrass

  208 Pavilion Trail, Nicholasville, KY 40356
• 

  

  /25

  Est $310,563

  Not Listed For Sale

  408 Southbrook Dr, Nicholasville, KY 40356

  • 4 Beds
  • 2.5 Baths
  • 2,012 Sq Ft
  • Built 1994

  408 Southbrook Dr, Nicholasville, KY 40356

  Last Sold Summary

  • 42 Days On Market
• 

  $382,850

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,519 Sq Ft

  Sycamore Bend Plan at Fairview Woods - Trend Collection, Nicholasville, KY 40356

  Ball Homes Builder

  125 Mcafee Dr Unit 40230723, Nicholasville, KY 40356
• 

  

  /31

  $530,000

  Sold Feb 06, 2026

  140 Rowanberry Dr, Nicholasville, KY 40356

  • 4 Beds
  • 2.5 Baths
  • 3,424 Sq Ft
  • Built 2019

  Last Sold Summary

  • 1% Below List Price
  • $155/SF
  • 64 Days On Market

  Current Estimated Value $534,274

  Last Listing Agent Michael Mallory The Brokerage

  140 Rowanberry Dr, Nicholasville, KY 40356
• 

  

  /45

  Est $316,228

  Not Listed For Sale

  404 Southbrook Dr Unit 2, Nicholasville, KY 40356

  • 4 Beds
  • 2.5 Baths
  • 2,145 Sq Ft
  • Built 1994

  404 Southbrook Dr Unit 2, Nicholasville, KY 40356

  Last Sold Summary

  • 2 Days On Market
• 

  /2

  $493,850

  New Construction Pending

  • 4 Beds
  • 3.5 Baths
  • 2,942 Sq Ft

  116 Hawks Bill Ct, Nicholasville, KY 40356

  The Bridgeport offers a luxurious first floor primary bedroom suite, open living areas, and three bedrooms and two baths plus loft on the second floor. Main floor living areas include a flex room open to the entry, and a large two story family room opening to the kitchen and breakfast area. The kitchen features an island design, a large walk-in pantry, and easy access to the mudroom with optional

  Dicksie Ward Christies International Real Estate Bluegrass

  116 Hawks Bill Ct, Nicholasville, KY 40356
• 

  /2

  $330,235

  Sold Sep 26, 2025

  420 San Antonio Way, Nicholasville, KY 40356

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 2024

  Last Sold Summary

  • 8% Below List Price
  • $204/SF
  • 164 Days On Market

  Current Estimated Value $341,219

  Last Listing Agent Maggie Taylor RE/MAX Creative Realty

  420 San Antonio Way, Nicholasville, KY 40356
• 

  

  /29

  Est $277,814

  Not Listed For Sale

  441 Southbrook Dr Unit 2A, Nicholasville, KY 40356

  • 3 Beds
  • 2 Baths
  • 1,236 Sq Ft
  • Built 1995

  441 Southbrook Dr Unit 2A, Nicholasville, KY 40356

  Last Sold Summary

  • 1 Day On Market
• 

  $342,850

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,519 Sq Ft

  Sycamore Bend Plan at The Arbours - Trend Collection at The Arbours, Nicholasville, KY 40356

  Ball Homes Builder

  200 Ivy Green Place Unit 38066421, Nicholasville, KY 40356
• 

  

  /11

  $424,900

  Sold May 29, 2026

  241 Skaggs Blvd, Nicholasville, KY 40356

  • 4 Beds
  • 2 Baths
  • 1,953 Sq Ft
  • Built 2026

  Last Sold Summary

  • $218/SF
  • 26 Days On Market

  Current Estimated Value $418,126

  Last Listing Agent Maggie Taylor RE/MAX Creative Realty

  241 Skaggs Blvd, Nicholasville, KY 40356
• 

  

  /19

  Est $295,967

  Not Listed For Sale

  324 Weslyn Way, Nicholasville, KY 40356

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1995

  324 Weslyn Way, Nicholasville, KY 40356

  Last Sold Summary

  • 2 Days On Market
• 

  

  /51

  $310,000

  • 3 Beds
  • 2.5 Baths
  • 1,578 Sq Ft

  109 Dallas Dr, Nicholasville, KY 40356

  Welcome to 109 Dallas Drive in Nicholasville! Conveniently Located in the Orchard neighborhood, this beautifully maintained 3-bedroom, 2.5-bath home offers 1,578 square feet of thoughtfully designed living space. Built just 4 years ago, the home features modern finishes throughout and an inviting open-concept floor plan perfect for everyday living and entertaining. The spacious kitchen is the

  Ami Pelat SimpliHOM

  109 Dallas Dr, Nicholasville, KY 40356
• 

  

  /13

  $90,000

  Sold Jul 30, 2025

  610 N Main St, Nicholasville, KY 40356

  • Land
  • 34,412 Sq Ft
  • $113,924 per Acre

  Last Sold Summary

  • 30% Below List Price
  • 25 Days On Market

  Current Estimated Value $104,895

  Last Listing Agent Terra Jeffries RE/MAX Elite Realty

  610 N Main St, Nicholasville, KY 40356
• 

  

  /27

  Est $276,500

  Not Listed For Sale

  345 Weslyn Way Unit 2A, Nicholasville, KY 40356

  • 3 Beds
  • 2 Baths
  • 1,360 Sq Ft
  • Built 1996

  345 Weslyn Way Unit 2A, Nicholasville, KY 40356

  Last Sold Summary

  • 2 Days On Market
• 

  /2

  $505,489

  New Construction $42K PRICE INCREASE Pending

  • 4 Beds
  • 2.5 Baths
  • 2,498 Sq Ft

  236 Gravel Springs Path, Nicholasville, KY 40356

  The Greenfield offers a great first floor layout with a large family room opening to a spacious island kitchen and breakfast area. The kitchen features an island design with countertop dining and a corner pantry. The first floor includes a coat closet and powder room, conveniently located off the entry hall, as well as a study at the rear of the home. Upstairs are the primary suite and three

  Matt Gerwin Christies International Real Estate Bluegrass

  236 Gravel Springs Path, Nicholasville, KY 40356
• 

  

  /21

  $308,000

  Sold Mar 06, 2026

  429 Southbrook Dr, Nicholasville, KY 40356

  • 3 Beds
  • 2.5 Baths
  • 1,852 Sq Ft
  • Built 1995

  Last Sold Summary

  • 2% Below List Price
  • $166/SF

  Current Estimated Value $306,136

  Last Listing Agent Michael Mallory The Brokerage

  429 Southbrook Dr, Nicholasville, KY 40356
• 

  

  /29

  Est $296,383

  Not Listed For Sale

  333 Weslyn Way, Nicholasville, KY 40356

  • 3 Beds
  • 2.5 Baths
  • 1,465 Sq Ft
  • Built 1995

  333 Weslyn Way, Nicholasville, KY 40356

  Last Sold Summary

  • 0 Days On Market
• 

  /2

  $327,750

  New Construction Pending

  • 3 Beds
  • 2 Baths
  • 1,780 Sq Ft

  315 Wisteria Ln, Nicholasville, KY 40356

  The Gaines Mill, part of the Trend Collection by Ball Homes, is an open layout ranch plan with three bedrooms. This split bedroom design places two bedrooms and the hall bath off the entry, and the primary bedroom suite at the rear of the home. The central kitchen offers both a breakfast area and countertop dining at the island and opens to the family room. The primary bedroom suite includes a

  Jason Landon Christies International Real Estate Bluegrass

  315 Wisteria Ln, Nicholasville, KY 40356
• 

  

  /22

  $328,000

  Sold Apr 24, 2026

  108 Winners Cir, Nicholasville, KY 40356

  • 3 Beds
  • 2 Baths
  • 1,641 Sq Ft
  • Built 2019

  Last Sold Summary

  • 6% Below List Price
  • $200/SF
  • 79 Days On Market

  Current Estimated Value $338,955

  Last Listing Agent Jordan Price National Real Estate

  108 Winners Cir, Nicholasville, KY 40356
• 

  

  /33

  Est $325,783

  Not Listed For Sale

  117 Weslyn Way, Nicholasville, KY 40356

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft
  • Built 1996

  117 Weslyn Way, Nicholasville, KY 40356

  Last Sold Summary

  • 21 Days On Market
• 

  

  /57

  $899,900

  $75K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 3,967 Sq Ft

  104 Barkley Estates, Nicholasville, KY 40356

  Seller is MOTIVATED! This home gives new meaning to "custom-built." Every square inch was curated and thoughtfully selected for this home. It's classy and modern, yet still warm and inviting. It's open, and bright with sliding doors across the back, making it the most stunning setting to entertain and host. The primary suite is huge, yet functional, giving endless possibilites to create a true

  Destiny Darby Keller Williams Commonwealth

  104 Barkley Estates, Nicholasville, KY 40356
• 

  Sold Dec 18, 2025

  117 Blackthorn Dr Unit 36449234, Nicholasville, KY 40356

  • 4 Beds
  • 2.5 Baths
  • 2,459 Sq Ft

  Last Sold Summary

  • 174 Days On Market

  Current Estimated Value $543,919

  117 Blackthorn Dr Unit 36449234, Nicholasville, KY 40356
• 

  

  /43

  Est $340,833

  Not Listed For Sale

  300 Southbrook Dr, Nicholasville, KY 40356

  • 4 Beds
  • 3 Baths
  • 2,620 Sq Ft
  • Built 1994

  300 Southbrook Dr, Nicholasville, KY 40356

  Last Sold Summary

  • 29 Days On Market
• 

  

  /134

  $2,900,000

  • 3 Beds
  • 4.5 Baths
  • 6,360 Sq Ft

  1368 Keene South Elkhorn Rd, Nicholasville, KY 40356

  Welcome to 1368 Keene South Elkhorn Road, a rare opportunity to own a truly turn key 20 acre horse farm! Conveniently located near Versailles and Lexington, it has been home to multiple stakes winners and Arkansas and Kentucky Derby contenders! Located at the end of a quiet country lane, you'll appreciate the curb appeal of the home from the second you drive up. Step on to the wrap around porch

  Mina Mattone Bluegrass Sotheby's International Realty

  1368 Keene South Elkhorn Rd, Nicholasville, KY 40356
• 

  

  /38

  $435,000

  Sold Mar 27, 2026

  217 Patmore Ln, Nicholasville, KY 40356

  • 4 Beds
  • 3 Baths
  • 2,353 Sq Ft
  • Built 2017

  Last Sold Summary

  • 5% Below List Price
  • $185/SF
  • 88 Days On Market

  Current Estimated Value $438,206

  Last Listing Agent Maggie Wells Real Broker, LLC

  217 Patmore Ln, Nicholasville, KY 40356

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