Old Pine Grove Houses for Sale

/40
$355,000
- 3 Beds
- 3 Baths
- 2,166 Sq Ft
115 Woodford Dr, Winchester, KY 40391

Discover a perfect blend of comfort and elegance as you step inside this charming home. Sitting on a generous 1/4 acre lot, this property offers a peaceful retreat with space to relax and entertain both inside and out. The heart of the home is the airy and open kitchen, featuring an oversized island that is perfect for gathering and sharing a meal. A dedicated keeping room provides a cozy

Brenda Sipes

WEICHERT REALTORS - ABG Properties

(859) 251-8500

115 Woodford Dr, Winchester, KY 40391
Explore Old Pine Grove
/117
$3,175,000
- 8 Beds
- 7.5 Baths
- 12,702 Sq Ft
4664 Lexington Rd, Winchester, KY 40391

Visitors to the farm are greeted by a substantial stone entry before traveling a gently winding path to the circular drive. There rests the grand residence, offering an ideal setting for entertaining family & friends. Ten minutes from Hamburg, the farm is located on the convenient Lexington/Winchester Road. Lovely views abound and the property retains remarkable privacy. The 13,500 square foot

Zach Davis Kirkpatrick & Company

4664 Lexington Rd, Winchester, KY 40391
/34
$312,750
- 3 Beds
- 2 Baths
- 1,792 Sq Ft
123 Strawberry Ln, Winchester, KY 40391

Priced below recent appraisal this almost new 3 bed 2 bath open layout ranch. 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. Granite kitchen counter tops with stainless steel 50/50 under-mount sink

Joseph Smallwood Christies International Real Estate Bluegrass

123 Strawberry Ln, Winchester, KY 40391
/24
$340,000
- 4 Beds
- 2.5 Baths
- 2,008 Sq Ft
118 Strawberry Ln, Winchester, KY 40391

Welcome Home!Kick back and relax on either the covered front porch or the spacious back patio of this charming 4-bedroom, 2.5-bath home. Perfectly positioned in a prime, central location. Just a short drive to Lexington, and only minutes from shopping, dining, schools, the hospital, and easy access to I-64 and the bypass, this home offers the perfect blend of comfort and

Susan Baldwin Rector Hayden Realtors

118 Strawberry Ln, Winchester, KY 40391
/30
$289,000 Open Sat 2PM - 4PM
- 3 Beds
- 2.5 Baths
- 1,606 Sq Ft
223 Bartram Ct, Winchester, KY 40391

Incredible value in the highly desirable Oakmont subdivision! This completely remodeled 3 bedroom, 2.5 bath home is truly move-in ready with all new paint, flooring, and granite countertops in every bathroom and kitchen. The stylish kitchen shines with an abundance of cabinetry, updated appliances and tile backsplash, flowing into the dining area that overlooks the deck and oversized

Jennifer Parsons RE/MAX Elite Lexington

223 Bartram Ct, Winchester, KY 40391

Kentucky Clark County Winchester Old Pine Grove

Why Live in Old Pine Grove

Old Pine Grove in Winchester is a semi-rural neighborhood situated between Lexington and Winchester, accessible via Interstate 64 and U.S. Route 60. The area features a mix of farmland and small subdivisions, with homes typically built post-1980, including ranch-style and new traditional designs with brick siding. The neighborhood's east end offers suburban amenities such as chain and local restaurants, a large flea market, and a movie theater. For outdoor activities, residents can visit nearby city parks like Legacy Grove Park, Wiseman Park, and College Park, or enjoy a round at Cassell Creek Golf Course. The local schools include the highly rated Strode Station Elementary School, with students continuing their education at Baker Intermediate, Campbell Junior High, and George Rogers Clark High School. Employment opportunities are available in Winchester's industrial park, Clark Regional Medical Center, and Bluegrass Community & Technical College's satellite campus. The neighborhood's crime rate is on par with the national average. Residents can also enjoy local dining options, including Woody's Sports Bar & Grill and Sherri's Café, and participate in the city's annual Beer Cheese Festival or explore the Beer Cheese Trail.

Learn more about living in Old Pine Grove

Home Trends in Old Pine Grove, KY

On average, homes in Old Pine Grove, Winchester sell after 44 days on the market compared to the national average of 52 days. The median sale price for homes in Old Pine Grove, Winchester over the last 12 months is $278,500, down 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$278,500

Median Single Family Sale Price

$278,500

Average Price Per Sq Ft

$163

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

2.20

Median List Price

$289,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

-1%

How to Buy a Home How to Finance a Home How to Sell a Home

In Old Pine Grove, there are currently 5 houses for sale, offering a variety of options for prospective buyers. With houses ranging from $289,000 to $3,175,000, there's something for every budget. As of September, 2025 the median home price in Old Pine Grove, Winchester is $289,000, while the average sale price is $304,367, providing insight into local market trends. On average, houses spend 44 days on the market before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options available to suit every lifestyle. Browse properties and houses for sale in Old Pine Grove, Winchester and find the perfect place to call home.

Old Pine Grove Types of Homes for Sale

Old Pine Grove Homes for Sale

More About Living in Old Pine Grove

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage