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Discover a private Bluegrass retreat on 11.4 acres in Hillgate, where contemporary architecture meets rolling green views and the quiet sounds of the countryside. Designed by noted architect Herb Greene and known as the O'Neill House, this distinctive residence combines expansive windows, a dramatic three-story dining atrium, and open living spaces that connect beautifully with the surrounding landscape. Tucked off Old Richmond Road with convenient interstate access, the property offers a secluded setting approximately 20 minutes from downtown Lexington. Thoughtful renovations enhance the home while preserving its distinctive architectural character. The kitchen offers new cabinetry, appliances, and a wine refrigerator, while refinished floors add warmth throughout the interior. Updates also include new living room windows and a sliding glass door by Renewal by Andersen, a renovated third-floor bathroom, and a new washer and dryer. Multiple fireplaces and versatile living spaces create comfortable settings for entertaining, relaxing, or working from home. The primary suite features an oversized en-suite and a generous sized closet. Newly finished guest space above the garage offers flexibility for visitors, a studio, or a home office. A large finished basement with marble flooring provides additional room to gather and unwind, while a steam shower and sauna bring a spa-like experience home. Outside, balconies, terraces, creeks, a bocce court, and multiple outdoor living areas invite everything from quiet morning coffee to evenings entertaining beneath the stars. Additional improvements include rooftop solar panels, a new main electrical panel, a water heater installed in 2025, radon mitigation, and new front, office, and side entry doors. The expanded garage includes added storage, cabinets, and a workbench, complemented by an outdoor shed. Replaced garage entry pavers, a replacement retaining wall, and patio lighting complete the updates. This distinctive Hillgate property brings together architectural character, thoughtful improvements, and space to enjoy Kentucky country living close to the city.

5 Beds ⋅ 6 Baths ⋅ 26028790 MLS

Discover a private Bluegrass retreat on 11.4 acres in Hillgate, where contemporary architecture meets rolling green views and the quiet sounds of the countryside. Designed by noted architect Herb Greene and known as the O'Neill House, this distinctive residence combines expansive windows, a dramatic three-story dining atrium, and open living spaces that connect beautifully with the surrounding landscape. Tucked off Old Richmond Road with convenient interstate access, the property offers a secluded setting approximately 20 minutes from downtown Lexington. Thoughtful renovations enhance the home while preserving its distinctive architectural character. The kitchen offers new cabinetry, appliances, and a wine refrigerator, while refinished floors add warmth throughout the interior. Updates also include new living room windows and a sliding glass door by Renewal by Andersen, a renovated third-floor bathroom, and a new washer and dryer. Multiple fireplaces and versatile living spaces create comfortable settings for entertaining, relaxing, or working from home. The primary suite features an oversized en-suite and a generous sized closet. Newly finished guest space above the garage offers flexibility for visitors, a studio, or a home office. A large finished basement with marble flooring provides additional room to gather and unwind, while a steam shower and sauna bring a spa-like experience home. Outside, balconies, terraces, creeks, a bocce court, and multiple outdoor living areas invite everything from quiet morning coffee to evenings entertaining beneath the stars. Additional improvements include rooftop solar panels, a new main electrical panel, a water heater installed in 2025, radon mitigation, and new front, office, and side entry doors. The expanded garage includes added storage, cabinets, and a workbench, complemented by an outdoor shed. Replaced garage entry pavers, a replacement retaining wall, and patio lighting complete the updates. This distinctive Hillgate property brings together architectural character, thoughtful improvements, and space to enjoy Kentucky country living close to the city.

2000 Hillgate Dr, Lexington

$2,323,000

If you're looking for legacy, luxury, and grand proportions, Highland Hall has it all--without the need for renovations. Located on a gated 5-acre estate near Lexington's Richmond Road corridor, Highland Hall was built by the son and namesake of Kentucky's very first Governor, Isaac Shelby. The estate has been meticulously restored to retain its historic features while creating a fully modernized, turn-key experience. This 6,800+/- sqft Greek Revival masterpiece was originally built in 1855 and now features a brand-new 2026 roof, all-new plumbing, updated 2-tank septic, and 400-amp electrical. Climate control is handled by a 3-unit geothermal HVAC system (8 GeoWells) and an additional heat pump for the first-floor primary suite. Enjoy all-new Anderson Pro Series windows, fresh premium paint, a Lutron system, original hand-milled heart pine floors, and custom walnut trim. The grand interiors flow to a private, fenced rear yard with a 2024 hot tub, outdoor shower, and a pond. This home has mastered the concept of intimate spaces specifically curated for daily living alongside grand spaces for lavish entertaining. Professionally redesigned since its history as a Decorators Showcase Home. Prequalified credentials required. **Furnishings priced upon request. Excludes any artwork collection**

5 Beds ⋅ 4 Baths ⋅ 26008568 MLS

If you're looking for legacy, luxury, and grand proportions, Highland Hall has it all--without the need for renovations. Located on a gated 5-acre estate near Lexington's Richmond Road corridor, Highland Hall was built by the son and namesake of Kentucky's very first Governor, Isaac Shelby. The estate has been meticulously restored to retain its historic features while creating a fully modernized, turn-key experience. This 6,800+/- sqft Greek Revival masterpiece was originally built in 1855 and now features a brand-new 2026 roof, all-new plumbing, updated 2-tank septic, and 400-amp electrical. Climate control is handled by a 3-unit geothermal HVAC system (8 GeoWells) and an additional heat pump for the first-floor primary suite. Enjoy all-new Anderson Pro Series windows, fresh premium paint, a Lutron system, original hand-milled heart pine floors, and custom walnut trim. The grand interiors flow to a private, fenced rear yard with a 2024 hot tub, outdoor shower, and a pond. This home has mastered the concept of intimate spaces specifically curated for daily living alongside grand spaces for lavish entertaining. Professionally redesigned since its history as a Decorators Showcase Home. Prequalified credentials required. **Furnishings priced upon request. Excludes any artwork collection**

6208 Old Richmond Rd, Lexington

$2,795,000

A rare masterpiece of country elegance and modern luxury, this spectacular 10-acre estate offers unparalleled privacy just moments from the city. Designed for both grand-scale entertaining and serene daily living, the property features a resort-style custom pool, a tranquil zen garden with a koi pond, a custom playhouse, and a pristine pond complete with a newly installed fountain and a dedicated well pump to maintain perfect water levels. The expansive outdoor oasis is further elevated by updated custom pergolas, a brand-new fire pit, and a convenient outdoor shower. Inside, impeccable craftsmanship defines the 5-bedroom, 5-full, and 2-half-bath residence. The gourmet chef's kitchen is a culinary dream, boasting top-of-the-line appliances, endless workspace, and a massive walk-in pantry. The luxurious primary suite serves as a private sanctuary with panoramic nature views, custom closets, and a spa-like bath with a deep soaking tub. A collector's dream, the massive 8-door garage accommodates up to 15 vehicles and features a private home office above. Mechanically flawless, the estate includes freshly painted perimeter fencing and a reconnected full-property irrigation system with a new pond pump. The previous owner performed many high-end upgrades, including 3 geothermal HVAC units with UV light filters, a water pressure booster pump, enhanced foundation drainage, and full-house blown-in foam insulation for maximum energy efficiency.

5 Beds ⋅ 7 Baths ⋅ 26013465 MLS

A rare masterpiece of country elegance and modern luxury, this spectacular 10-acre estate offers unparalleled privacy just moments from the city. Designed for both grand-scale entertaining and serene daily living, the property features a resort-style custom pool, a tranquil zen garden with a koi pond, a custom playhouse, and a pristine pond complete with a newly installed fountain and a dedicated well pump to maintain perfect water levels. The expansive outdoor oasis is further elevated by updated custom pergolas, a brand-new fire pit, and a convenient outdoor shower. Inside, impeccable craftsmanship defines the 5-bedroom, 5-full, and 2-half-bath residence. The gourmet chef's kitchen is a culinary dream, boasting top-of-the-line appliances, endless workspace, and a massive walk-in pantry. The luxurious primary suite serves as a private sanctuary with panoramic nature views, custom closets, and a spa-like bath with a deep soaking tub. A collector's dream, the massive 8-door garage accommodates up to 15 vehicles and features a private home office above. Mechanically flawless, the estate includes freshly painted perimeter fencing and a reconnected full-property irrigation system with a new pond pump. The previous owner performed many high-end upgrades, including 3 geothermal HVAC units with UV light filters, a water pressure booster pump, enhanced foundation drainage, and full-house blown-in foam insulation for maximum energy efficiency.

601 Delong Rd, Lexington

$2,200,000

Experience unparalleled luxury in this exquisite English Manor, a Schaefer Homes masterpiece in the prestigious, gated Hartland Estates. The grand two-story entry, featuring a curved staircase and stone-with-wood-inlay flooring, sets a stately tone that continues throughout. While the home retains its magnificent original woodwork—including mahogany and knotty pine cabinetry, beams, and trusses—it has been thoughtfully elevated with a completely reimagined gourmet kitchen and a stunningly updated primary retreat. The lavish first-floor primary suite now boasts a modern, spa-like bath and vaulted sitting room with fireplace. The expansive floor plan includes six fireplaces, a walk-out basement with a pub-style bar, home theatre, and gym, all situated on a lush .67-acre lot. Modern efficiencies like geothermal HVAC and a 4-car garage complete this one-of-a-kind estate.

5 Beds ⋅ 7 Baths ⋅ 26007066 MLS

Experience unparalleled luxury in this exquisite English Manor, a Schaefer Homes masterpiece in the prestigious, gated Hartland Estates. The grand two-story entry, featuring a curved staircase and stone-with-wood-inlay flooring, sets a stately tone that continues throughout. While the home retains its magnificent original woodwork—including mahogany and knotty pine cabinetry, beams, and trusses—it has been thoughtfully elevated with a completely reimagined gourmet kitchen and a stunningly updated primary retreat. The lavish first-floor primary suite now boasts a modern, spa-like bath and vaulted sitting room with fireplace. The expansive floor plan includes six fireplaces, a walk-out basement with a pub-style bar, home theatre, and gym, all situated on a lush .67-acre lot. Modern efficiencies like geothermal HVAC and a 4-car garage complete this one-of-a-kind estate.

4848 Chelmsbury Ln, Lexington

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