$774,900
5 bd · 3.5 ba · 3,560 sqft
4344 Steamboat Road, Lexington, KY 40514
Courtesy of Christies International Real Estate Bluegrass
Listing data updated August 5, 2026
About the Neighborhood
Living in Southwest Lexington
Southwest Lexington is the city's steadiest family quadrant — subdivisions like Willow Oak, Dogwood Trace, Ashbrooke, and Wyndham Hills, built from the '80s through the 2020s, with top-rated schools and the Nicholasville Road retail corridor close by. Nothing about it is flashy; everything about it works.
This side of town filled in as Lexington's classic suburban growth story — subdivision by subdivision through the '80s, '90s, and 2000s, in the New Traditional style that defines the area: brick fronts, cul-de-sacs, community parks and walking paths threaded through. It has stayed one of the city's most reliably in-demand family markets ever since.
On the market now
Homes for Sale in Southwest Lexington
$595,000
4 bd · 3.5 ba · 3,279 sqft
1336 Glenview Drive, Lexington, KY 40514
Courtesy of ERA Select Real Estate
$549,900
4 bd · 3.5 ba · 3,382 sqft
2441 Doubletree Court, Lexington, KY 40514
Courtesy of RE/MAX Creative Realty
$469,900
4 bd · 2.5 ba · 2,812 sqft
4016 Sweetspire Drive, Lexington, KY 40514
Courtesy of Bluegrass Properties Group
$444,900
4 bd · 2.5 ba · 2,290 sqft
805 Willow Oak Circle, Lexington, KY 40514
Courtesy of The Brokerage
$389,900
3 bd · 2 ba · 1,706 sqft
569 Goldon Trophy Trail, Lexington, KY 40514
Courtesy of The Brokerage
Neighborhood guide
Inside Southwest Lexington
- The rhythm here is family-suburban at its best: kids on the walking paths, Little League Saturdays at Waverly Park, cul-de-sacs where the neighbors actually know each other.
The subdivisions each have their own character — Willow Oak's established shade, Dogwood Trace's newer streets, Wyndham Hills' larger lots — but they share the same fundamentals: solid schools, low drama, and a location that makes every commute reasonable. - Homes in the area: about 5,230.
Era: median year built 1994.
Typical single-family size: around 2,140 square feet, above the national average.
Figures as-published by homes.com's Lexington local guide (extracted August 2026); housing stock, not asking prices. Live inventory and median are at the top of this page. - Nicholasville Road's big-box corridor covers the practical list, and The Summit at Fritz Farm covers the fun one — an outdoor district whose restaurant lineup runs from national names to some of Lexington's most popular local spots.
Shillito Park sits right in the middle of the retail zone, which sums this area up nicely: even the shopping trip comes with a park attached. - The quadrant sits between Harrodsburg Road, Clays Mill Road, and Nicholasville Road, with Man o' War Boulevard stitching them together — so commutes run short in every direction: fifteen-ish minutes downtown, quick access toward Jessamine County, and an easy run to anywhere on the south side.
Schools
Schools in Southwest Lexington
Assigned Schools
Four elementary schools serve the area. From there (per homes.com's guide, with Niche ratings high across the board): homes west of Clays Mill Road feed Beaumont Middle School and Paul Laurence Dunbar High School; homes east of Clays Mill feed Jessie M. Clark Middle School and Lafayette High School. Both patterns are among the strongest in the county — Dunbar and Lafayette are two of Lexington's most sought-after high schools.
Private options nearby include Lexington Christian Academy and The Lexington School, both highly rated.
Private options nearby include Lexington Christian Academy and The Lexington School, both highly rated.
Explore nearby
Neighborhoods Near Southwest Lexington
Questions
Southwest Lexington Home-Buying FAQ
Fayette County Public Schools, in two strong feeder patterns split at Clays Mill Road: Beaumont Middle and Dunbar High to the west, Clark Middle and Lafayette High to the east. We verify the exact assignment for any home you're considering, since the line runs through the area.
Mostly New Traditional single-family homes — brick fronts, two stories, cul-de-sac streets — built from the 1980s through the 2020s across subdivisions like Willow Oak, Dogwood Trace, Ashbrooke, and Wyndham Hills. The live listings above show today's mix.
The Nicholasville Road corridor's big-box retail, The Summit at Fritz Farm's restaurants and shops, and Shillito Park are all within a few minutes. Daily errands rarely leave the quadrant.
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