Alyssa M Boley

Winchester KY

Coldwell Banker McMahan

100 Closed Sales

$23.5M Total Value

$102K - $900K Price Range

$234.7K Average Price

Prior 5 years

About Alyssa M

Alyssa Boley has been helping people in Winchester and Central/Eastern Kentucky buy and sell homes since 2008. She loves that her job allows her to help others and meet new clients. Over the years, many of her clients have become lifelong friends. Alyssa’s clients expect and deserve her full attention and she prides herself on taking care of all the details. This allows her clients to enjoy the experience and hopefully have fun along the way. When she is working with buyers, her number one priority is finding them their “perfect” home. And when it comes time to sell, she works very hard to get her clients the best possible price for their home. Communication is very important in any real estate transaction. Alyssa always tries to answer her phone, and if she is with another client, she returns calls immediately. If you are looking to buy or sell, give her a call and you will be the next one holding the “SOLD” sign when they get to closing. Alyssa looks forward to speaking with you on your next real estate journey.

Home Types: House, Lot/Land, Manufactured, Commercial, Other

Years of Experience: 18

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	10
Total Value	$3,521,000
Average Sale Price	$352,100
Price Range	$65K - $900K

Buyer Deals
Total Deals	8
Total Value	$2,637,000
Average Sale Price	$329,625
Price Range	$177K - $550K

1 Year View by Quarter

Seller Deals
Total Deals	23
Total Value	$6,364,000
Average Sale Price	$276,696
Price Range	$65K - $900K

Buyer Deals
Total Deals	14
Total Value	$4,359,000
Average Sale Price	$311,357
Price Range	$177K - $550K

2 Year View by Quarter

Seller Deals
Total Deals	54
Total Value	$12,244,500
Average Sale Price	$226,750
Price Range	$10K - $900K

Buyer Deals
Total Deals	46
Total Value	$11,223,400
Average Sale Price	$243,987
Price Range	$25K - $550K

5 Year View

Neighborhoods Alyssa M is Experienced In

Alyssa M's Active Listings

$149,900
- 3 Beds
- 1 Bath
- 1,362 Sq Ft
11 Taylor Ave

Winchester, KY
Back on Market! Buyers financing fell through. This 3 BR home located in the heart of Winchester and just minutes from the vibrant downtown area, offers the perfect blend of convenience, character, and opportunity. Great opportunity for investors or homeowners. Outside you will love the spacious yard and can relax on the back deck with your morning coffee. Enjoy being within close proximity to

Alyssa M Boley Coldwell Banker McMahan

$1,695,000
- 3 Beds
- 2.5 Baths
- 4,518 Sq Ft
3166 Colby Rd

Winchester, KY
Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points in Clark

Alyssa M Boley Coldwell Banker McMahan

$259,000
- Land
- 44 Acres
- $5,880 per Acre
0 Lower Cane Creek Edwards Rd

Unit 26009299

Stanton, KY
Nestled in the heart of Eastern Kentucky, this breathtaking 44.05-acre property offers a rare opportunity to own your own private retreat near the iconic Red River Gorge. Located just outside of Stanton, this expansive tract is a nature lover's dream, featuring rolling hills, mature timber, and stunning panoramic views that stretch for miles. Whether you're envisioning your forever home, a

Alyssa M Boley Coldwell Banker McMahan

$199,900
- 5 Beds
- 2 Baths
- 2,444 Sq Ft
148 W Lexington Ave

Winchester, KY
Located in the heart of Winchester, this spacious and versatile two-story home offers incredible potential for both homeowners and savvy investors alike. With a total of 5 BR- this property provides ample space to accommodate a variety of living arrangements, from a large single-family home to a high -demand rental opportunity. The home features a welcoming covered front porch, perfect for

Alyssa M Boley Coldwell Banker McMahan

$289,000
- 5 Beds
- 2 Baths
- 1,838 Sq Ft
426 E Broadway St

Winchester, KY
Welcome home to this beautifully reimagined property in Winchester! Originally built in 1945, this 1.5-story home has been completely transformed from the ground up, offering the perfect blend of classic charm and modern peace of mind. With approximately 1,838 square feet, this home has been fully gutted to the studs and thoughtfully rebuilt—featuring all-new electrical, plumbing, HVAC system,

Alyssa M Boley Coldwell Banker McMahan

$249,500
- 4 Beds
- 2.5 Baths
- 1,930 Sq Ft
112 Augusta Dr

Mount Sterling, KY
Opportunity in Mt. Sterling- Located just minutes from the interstate, this two story home offers space, convenience, and incredible potential. Home features a front porch, and attached garage, the home includes a spacious layout with a large bonus bedroom over the garage. Step outside and enjoy the back deck, ideal for relaxing or entertaining while overlooking the backyard. with solid bones and

Alyssa M Boley Coldwell Banker McMahan

$132,000
- 2 Beds
- 1 Bath
- 818 Sq Ft
178 Sleepy Hollow Rd

Wellington, KY
Nestled in a peaceful, wooded setting near the Cave Run Lake area, this charming two-bedroom, one-bath cabin is ideally located approximately 10 minutes from Longbow Marina and less than 30 minutes from the Red River Gorge area. Surrounded by mature trees and natural beauty, it offers the perfect blend of privacy and convenience. The main floor features an open-concept layout with an updated

Alyssa M Boley Coldwell Banker McMahan

Recently Sold

$900,000

Sold Apr 10, 2026
00 Lower Cane Creek Rd

Stanton, KY
- 44% Below List
- 484 Days On Market
Alyssa M Boley Coldwell Banker McMahan

$200,000

Sold Apr 3, 2026
- 3 Beds
- 1.5 Baths
- 1,500 Sq Ft
95 Len Dr

Clay City, KY
- 1% Above List
- $133/SF
- 18 Days On Market
- Current Est. Value $196K
Alyssa M Boley Coldwell Banker McMahan

$550,000

Sold Dec 29, 2025
- 4 Beds
- 5.5 Baths
- 3,856 Sq Ft
232 Tahoe Way

Richmond, KY
- 19% Below List
- $143/SF
- 158 Days On Market
- Current Est. Value $556K
Alyssa M Boley Coldwell Banker McMahan

$238,000

Sold Dec 2, 2025
- 2 Beds
- 1.5 Baths
- 1,230 Sq Ft
645 Right Fork Fixer Rd

Unit 144

Zoe, KY
- 16% Below List
- $193/SF
- 31 Days On Market
Alyssa M Boley Coldwell Banker McMahan

$175,000

Sold Nov 21, 2025
- 3 Beds
- 1 Bath
- 1,300 Sq Ft
67 1st St

Clay City, KY
- 15% Below List
- $135/SF
- 3 Days On Market
- Current Est. Value $179K
Alyssa M Boley Coldwell Banker McMahan

$550,000

Sold Sep 4, 2025
- 5 Beds
- 3 Baths
- 3,489 Sq Ft
594 Earlymeade Dr

Winchester, KY
- 4% Below List
- $158/SF
- 43 Days On Market
- Current Est. Value $556K
Alyssa M Boley Coldwell Banker McMahan

$225,000

Sold Aug 21, 2025
- 3 Beds
- 1 Bath
- 1,080 Sq Ft
26 Stefanie Ct

Winchester, KY
- $208/SF
- 12 Days On Market
- Current Est. Value $228K
Alyssa M Boley Coldwell Banker McMahan

$287,000

Sold Aug 20, 2025
- 3 Beds
- 2 Baths
- 1,402 Sq Ft
220 Mcdowell Dr

Winchester, KY
- 12% Below List
- $205/SF
- 36 Days On Market
- Current Est. Value $298K
Alyssa M Boley Coldwell Banker McMahan

$65,000

Sold Jul 25, 2025
- 3 Beds
- 1 Bath
- 3,220 Sq Ft
4089 Woodward Rd

Germantown, KY
- 28% Below List
- $20/SF
- 61 Days On Market
Alyssa M Boley Coldwell Banker McMahan

Awards and Designations

NAR - National Association of Realtors
Certified Relocation Professional

Agent License: Kentucky 214156

Alyssa M Boley

(859) 681-7814

Homes for Sale by City

Alyssa M Boley

About Alyssa M

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

2 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Alyssa M is Experienced In

Alyssa M's Listings and Deals

Alyssa M's Active Listings

Recently Sold

Awards and Designations