Jessamine County’s housing heartbeat is Nicholasville, where the median sale price sits at $285,000—up 4.7% from last spring—while active listings remain under 110 homes most weekends. Entry-level inventory clusters between $200–250k in the Maple Grove and Garden Springs subdivisions north of US-27; move-up buyers target Brookside Estates and Keene Crossing, where 2,400-sq-ft brick homes trade closer to $325–375k. New construction is concentrated along South Main Street corridor: Ramsey Builders and Higdon Homes each have 40-lot phases releasing this summer, priced from $309k to $424k with standard 3-car garages and quarter-acre lots.

Investors keep an eye on the Wheeler Avenue pocket west of downtown; 1950s bungalows bought for $175k last year now rent for $1,550/month after $25k in cosmetic updates, a 9.4% gross yield. Days-on-market for the entire city averaged 18 days in April, but well-priced homes under $275k frequently receive offers within 48 hours. Multiple-offer etiquette has normalized: expect 2–4 competing contracts, escalation clauses up to 3% over list, and appraisal-gap coverage of $5–10k.

• First-Time Buyers ($200–250k): Maple Grove, Garden Springs, Shadybrook. 1,200–1,400 sq ft, 3-bed ranches built 1980–1995; HOA $0–75. Quick access to East Jessamine schools and Walmart on Laurel Road.
• Move-Up Families ($275–350k): Brookside Estates, Clemens Heights, Falling Spring. 1,800–2,200 sq ft, 4-bed two-story with basement. Walkable to Rosenwald-Dunbar Elementary (rated 9/10) and Ruth Chris Park.
• Equestrian & Acreage ($450–650k): Brannon Road, Long Branch, Clear Creek. 5–15 acres, barns allowed, zoned A-1 Agricultural. Ten minutes to Keeneland and Blue Grass Stockyards.
• New Construction ($309–424k): Keene Pointe, South Main Village, Legacy at Nicholasville. Builder incentives up to $7k toward closing when you finance with preferred lenders like NMHL.

Kentucky Housing Corporation’s Regular DAP provides a silent second mortgage of up to $10,000 at 3.75% that can be paired with FHA, VA, USDA, or conventional loans. Income limits inside Jessamine County are $95,900 for a 1–2-person household and $111,300 for 3+; purchase price cap is $481,176. If you need more, the new Homeowner Assistance for Tomorrow (HAT) forgives 20% of the assistance amount each year, turning the loan into a grant after five years of occupancy.

On the local side, Jessamine County Affordable Housing Trust Fund will match up to $5,000 for first-time buyers who complete a HUD-certified class at Jessamine County Extension Office on Wednesday evenings. Veterans using NMHL’s KY Hero stack can layer $5k county grant + $10k KHC + VA 100% financing, often walking away from closing with a $2,000+ surplus after earnest-money refund.

Jessamine County’s 2024 property-tax rate is 0.846% of assessed value (which equals roughly 81% of sale price). On a $285k purchase, expect an annual tax bill of $2,405 paid in two installments (November and June). City tax adds another 0.178%, or $507 on the same home. Because Kentucky uses the Homeowner Exemption, you can knock off $40,500 of assessed value if the house is owner-occupied, saving roughly $340 per year.

Homeowners insurance runs $1,050–1,300 annually for standard frame homes; premiums inch higher south of US-27 where ISO fire rating slips to 5/10. Closing costs average 2.1% of price—$5,985 on a $285k home—covering lender fees, appraisal, title, recording, and state deed tax of $0.50 per $500. Budget an extra $600 if your subdivision requires a private well inspection or septic dye test.

If you run a landscaping crew, Etsy store, or medical-coding side hustle, Nicholasville lenders typically demand two years of tax returns. NMHL’s Entrepreneur Program instead accepts 12 months of personal or business bank statements, counts expense factors of 15–50% by industry, and caps DTI at 50% with a 660 FICO. Average approved loan size last quarter: $312k with 12.3% down—far below the 20% banks require for stated-income products.

We can also gross-up self-employed income by 25% if your business pays federal taxes at the corporate level, effectively boosting qualifying income without raising your tax bracket. Common Nicholasville niches: horse-trainer income (documented via Keeneland 1099s), craft-brew consultants (expense ratio 30%), and OnlyFans creators (platform statements accepted). Our underwriters work from an office on South Main, so you can walk in with statements on Monday and have a conditional approval by Thursday.

Jessamine County Schools operate four elementary, two middle, and one high school inside Nicholasville city limits. Elementary ratings on Niche.com range A–A−, and East Jessamine Middle scores 8/10—key metrics for families who plan to resell within 7–10 years. Homes zoned for Rosenwald-Dunbar Elementary command roughly $18 per sq ft more than those feeding into Nicholasville Elementary, and the premium has widened 4% annually since 2020.

For private options, Providence Christian Academy (K–12) sits adjacent to Brookside subdivision, and tuition of $7,900 is attractive compared to Lexington private schools at $14k+. Proximity to Asbury University in Wilmore also supports a steady rental pool—three-bedroom homes within a 10-minute drive of campus average $1,625/month lease rates with 96% occupancy in fall semesters.