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585 Ruddles Mill Cynthiana Road, Cynthiana, KY 41031
New Listing
$1,699,000
Property Type:
Residential
Bedrooms:
6
Baths:
3
Square Footage:
7,142
Lot Size (sq. ft.):
2,112,660
Status:
Active
Current Price:
$1,699,000
List Date:
6/27/2026
Last Modified:
6/27/2026
Description
Professional Pictures, Drone footage, Video Coming Soon. A Rare Legacy Estate Rich in History, Privacy, and Luxury Experience the perfect blend of timeless elegance, modern comfort, and historic significance in this extraordinary 6-bedroom, 3-bath residence offering over 7,000 square feet of living space. Ideally situated along the Harrison and Bourbon County line, this remarkable property provides unparalleled privacy, breathtaking rural surroundings, and a lifestyle that is truly one of a kind. Far from an ordinary farmhouse, this custom-built estate showcases exceptional craftsmanship and thoughtful design throughout. An abundance of natural light fills the home, especially on the main level, where expansive windows frame picturesque countryside views. The dramatic two-story great room serves as the centerpiece of the home, featuring soaring ceilings, an overlook balcony, and four glass doors that invite the outdoors in while providing seamless access to the wraparound porch. From this stunning vantage point, enjoy mesmerizing panoramic views of rolling farmland and Kentucky's scenic landscape. Adding to the home's unique character is a dedicated music room with exceptional acoustics, creating the perfect space for musicians, performances, gatherings, or simply enjoying the rich sound and ambiance of this remarkable setting with sound system throughout the home. Designed for both entertaining and everyday living, the chef-inspired kitchen is a true showpiece, featuring granite countertops, an expansive center island, a spacious butler's pantry, and convenient service access to the elegant formal dining room. The luxurious first-floor primary suite offers a private retreat complete with a clawfoot soaking tub, walk-in shower, private water closet with commode and bidet, oversized walk-in closet, and spa-inspired amenities designed for ultimate comfort and relaxation. The walk-out lower level provides exceptional flexibility and is perfectly suited for multi-generational living, guest accommodations, or a private in-law suite. Step outside and discover resort-style amenities designed to elevate everyday living, including a saltwater pool, hot tub, and expansive outdoor living spaces surrounded by peaceful countryside and unmatched privacy. Whether entertaining family and friends or enjoying a quiet evening under the stars, this outdoor oasis offers an extraordinary setting for creating lasting memories. Steeped in Kentucky history, the farm was originally commissioned to the prior family in recognition of their service during the French and Indian War, which concluded in 1763--nearly three decades before Kentucky achieved statehood. Historical elements remain thoughtfully preserved throughout the property, including a mantle crafted from the original one-room log cabin that once stood on the land and a historic grinding stone incorporated into the home's hearth. Today, this remarkable estate offers productive farmland, established crops, an orchard, and complete seclusion, creating a rare opportunity to own a significant piece of Kentucky history while enjoying the finest comforts of modern luxury. Rich in character, surrounded by natural beauty, and enhanced by exceptional amenities, this is far more than a home--it is a legacy estate destined to be treasured for generations.
Supplements: ********
More Information MLS# 26013758
Listing Information
Comp Sale YN: No
Property Sub Type: Single Family Residence
Address
Zip +4: 9141
Directions: At the 4-way intersection (Hwy-1940 x Hwy-1893) where Ruddles Mill Road Meets Millersburg / Ruddles Mill. You will travel 2.5 miles on Ruddles Mill Cynthiana Road (Hwy-1940) towards Cynthiana. The gat
Parcel Number: 131-0000-006-01-000
Tax District: Bourbon
County: Harrison
Street Number: 585
Street Name: Ruddles Mill Cynthiana
Street Suffix: Road
State: KY
Zip Code: 41031
Contract
Start Showing Date: 2026-06-27
Listing Agreement: Exclusive Right To Sell
Occupant Type: Occupied
Office Exclusive YN: No
List Price/SqFt: 237.89
Current Price: $1,699,000
Original List Price: 1699000
Status: Active
Listing Contract Date: 2026-06-14
List Price: $1,699,000
Currently Not Used
List Price/Acre: 35030.93
Tax & Legal
Elementary School: Harrison Co
Middle Or Junior School: Harrison Co
High School: Harrison Co
Tax Rate: 10.48
Association/Community
Association YN: No
Interior
Living Area: 7142
Living Area Source: Public Records
Bathrooms Half: 0
Above Grade Finished Area: 5340
Below Grade Finished Area: 1802
Above Grade Unfinished Area: 0
Below Grade Unfinished Area: 0
Non-Compliant Total SqFt: 0
Basement YN: Yes
Fireplace YN: Yes
Fireplaces Total: 2
Bedrooms Total: 6
Bathrooms Total: 3
Bathrooms Full: 3
Parking Information
Garage YN: Yes
Garage Spaces: 3
Carport YN: No
Building
Home Warranty YN: No
Accessibility Features YN: Yes
Year Built: 2002
Lot
Lot Size Source: Public Records
Lot Size Acres: 48.5
Lot Size Square Feet: 2112660
Pool Private YN: Yes
View YN: Yes
Waterfront YN: No
Water Body Access YN: No
Horse YN: Yes
Utilities
Cooling YN: Yes
Heating YN: Yes
Cable Available: 1
Electricity Connected: 1
Phone Available: 1
Propane: 1
Sewer Connected: 1
Water Connected: 1
Remarks
Public Remarks: Professional Pictures, Drone footage, Video Coming Soon. A Rare Legacy Estate Rich in History, Privacy, and Luxury Experience the perfect blend of timeless elegance, modern comfort, and historic significance in this extraordinary 6-bedroom, 3-bath residence offering over 7,000 square feet of living space. Ideally situated along the Harrison and Bourbon County line, this remarkable property provides unparalleled privacy, breathtaking rural surroundings, and a lifestyle that is truly one of a kind. Far from an ordinary farmhouse, this custom-built estate showcases exceptional craftsmanship and thoughtful design throughout. An abundance of natural light fills the home, especially on the main level, where expansive windows frame picturesque countryside views. The dramatic two-story great room serves as the centerpiece of the home, featuring soaring ceilings, an overlook balcony, and four glass doors that invite the outdoors in while providing seamless access to the wraparound porch. From this stunning vantage point, enjoy mesmerizing panoramic views of rolling farmland and Kentucky's scenic landscape. Adding to the home's unique character is a dedicated music room with exceptional acoustics, creating the perfect space for musicians, performances, gatherings, or simply enjoying the rich sound and ambiance of this remarkable setting with sound system throughout the home. Designed for both entertaining and everyday living, the chef-inspired kitchen is a true showpiece, featuring granite countertops, an expansive center island, a spacious butler's pantry, and convenient service access to the elegant formal dining room. The luxurious first-floor primary suite offers a private retreat complete with a clawfoot soaking tub, walk-in shower, private water closet with commode and bidet, oversized walk-in closet, and spa-inspired amenities designed for ultimate comfort and relaxation. The walk-out lower level provides exceptional flexibility and is perfectly suited for multi-generational living, guest accommodations, or a private in-law suite. Step outside and discover resort-style amenities designed to elevate everyday living, including a saltwater pool, hot tub, and expansive outdoor living spaces surrounded by peaceful countryside and unmatched privacy. Whether entertaining family and friends or enjoying a quiet evening under the stars, this outdoor oasis offers an extraordinary setting for creating lasting memories. Steeped in Kentucky history, the farm was originally commissioned to the prior family in recognition of their service during the French and Indian War, which concluded in 1763--nearly three decades before Kentucky achieved statehood. Historical elements remain thoughtfully preserved throughout the property, including a mantle crafted from the original one-room log cabin that once stood on the land and a historic grinding stone incorporated into the home's hearth. Today, this remarkable estate offers productive farmland, established crops, an orchard, and complete seclusion, creating a rare opportunity to own a significant piece of Kentucky history while enjoying the finest comforts of modern luxury. Rich in character, surrounded by natural beauty, and enhanced by exceptional amenities, this is far more than a home--it is a legacy estate destined to be treasured for generations.
Accessibility Features
Accessible Bedroom: 1
Accessible Central Living Area: 1
Accessible Closets: 1
Accessible Common Area: 1
Accessible Doors: 1
Accessible Full Bath: 1
Accessible Hallway(s): 1
Accessible Kitchen: 1
Amenity Fee Details
Amenity Fee YN: No
Appliances
Dishwasher: 1
Dryer: 1
Microwave: 1
Oven: 1
Range: 1
Refrigerator: 1
Self Cleaning Oven: 1
Washer: 1
Architectural Style
Cape Cod: 1
Attic Features
Access Only: 1
Finished: 1
Floored: 1
Storage Only: 1
Basement
Concrete: 1
Exterior Entry: 1
Finished: 1
Full: 1
Interior Entry: 1
Sump Pump: 1
Walk-Out Access: 1
Walk-Up Access: 1
Construction Materials
Vinyl Siding: 1
Cooling
Ceiling Fan(s): 1
Electric: 1
Geothermal: 1
Exterior Features
Fire Pit: 1
Garden: 1
Hot Tub: 1
Storm Door(s): 1
Fencing
Wire: 1
Wood: 1
Fireplace Features
Family Room: 1
Gas Log: 1
Great Room: 1
Propane: 1
Flooring
Concrete: 1
Hardwood: 1
Tile: 1
Vinyl: 1
Foundation Details
Concrete Perimeter: 1
Heating
Geothermal: 1
Heat Pump: 1
Propane Tank Leased: 1
Horse Amenities
Pasture: 1
Interior Features
Breakfast Bar: 1
Ceiling Fan(s): 1
Eat-in Kitchen: 1
Entrance Foyer: 1
In-Law Floorplan: 1
Primary First Floor: 1
Soaking Tub: 1
Walk-In Closet(s): 1
Laundry Features
Electric Dryer Hookup: 1
Lower Level: 1
Main Level: 1
Washer Hookup: 1
Levels
Three Or More: 1
Lot Features
Few Trees: 1
Landscaped: 1
Secluded: 1
Other Structures
Other: 1
Parking Features
Attached Garage: 1
Driveway: 1
Garage Door Opener: 1
Garage Faces Side: 1
Patio And Porch Details
Covered Porch: 1
Enclosed Porch: 1
Front Porch: 1
Rear Porch: 1
Side Porch: 1
Wrap Around Porch: 1
Patio And Porch Features
Deck: 1
Patio: 1
Porch: 1
Other: 1
Possession
Close Of Escrow: 1
Private Pool Features
Above Ground: 1
Roof
Dimensional Style: 1
Shingle: 1
Sewer
Septic Tank: 1
Showing Considerations
Pet(s) on Premises: 1
Structure Type
House: 1
View
Farm: 1
Trees/Woods: 1
Water Heater
Electric: 1
Geothermal: 1
Water Source
Public: 1
Window Features
Insulated Windows: 1
Screens: 1
Showing Requirements
Call Listing Agent: 1
Showing Service: 1
Showing Information
Showing Instructions: SHOWING-TIME, Sentri-Lock, Call Realtor, No walking on the property without appointment, Gated, No driving on 48.5 acres- soybean crop, Occupied -Dogs if seller is present. Close gates before leaving the property.
Room Types
Bathroom 1: 1
Bathroom 1 Level: First
Bathroom 3: 1
Bathroom 3 Level: Lower
Bedroom 2: 1
Bedroom 2 Level: Second
Bedroom 3: 1
Bedroom 3 Level: Lower
Bedroom 4: 1
Bedroom 4 Level: Lower
Bedroom 5: 1
Bedroom 5 Level: Lower
Bonus Room: 1
Bonus Room Level: Second
Dining Room: 1
Dining Room Level: First
Family Room: 1
Family Room Level: First
Foyer: 1
Foyer Level: First
Great Room: 1
Great Room Level: First
Kitchen: 1
Kitchen Level: Lower
Office: 1
Office Level: Lower
Other: 1
Other Level: Lower
Primary Bedroom: 1
Primary Bedroom Level: First
Recreation Room: 1
Recreation Room Level: Second
Utility Room: 1
Utility Room Level: Lower
Status Change Information
Status Change Timestamp: 2026-06-27
Tax Legal
MLS Area Major: 016 - Harrison County
Subdivision Name: Rural
High School District: Bourbon County - 6
Property Features
Utilities: Cable Available; Electricity Connected; Phone Available; Propane; Sewer Connected; Water Connected; Cable Available; Electricity Connected; Phone Available; Propane; Sewer Connected; Water Connected
Accessibility Features: Accessible Bedroom; Accessible Central Living Area; Accessible Closets; Accessible Common Area; Accessible Doors; Accessible Full Bath; Accessible Hallway(s); Accessible Kitchen
Appliances: Dishwasher; Dryer; Microwave; Oven; Range; Refrigerator; Self Cleaning Oven; Washer
Architectural Style: Cape Cod
Attic Features: Access Only; Finished; Floored; Storage Only
Basement: Concrete; Exterior Entry; Finished; Full; Interior Entry; Sump Pump; Walk-Out Access; Walk-Up Access
Construction Materials: Vinyl Siding
Cooling: Ceiling Fan(s); Electric; Geothermal
Exterior Features: Fire Pit; Garden; Hot Tub; Storm Door(s)
Fencing: Wire; Wood
Fireplace Features: Family Room; Gas Log; Great Room; Propane
Flooring: Concrete; Hardwood; Tile; Vinyl
Foundation Details: Concrete Perimeter
Heating: Geothermal; Heat Pump; Propane Tank Leased
Horse Amenities: Pasture
Interior Features: Breakfast Bar; Ceiling Fan(s); Eat-in Kitchen; Entrance Foyer; In-Law Floorplan; Primary First Floor; Soaking Tub; Walk-In Closet(s)
Laundry Features: Electric Dryer Hookup; Lower Level; Main Level; Washer Hookup
Levels: Three Or More
Lot Features: Few Trees; Landscaped; Secluded
Other Structures: Other
Parking Features: Attached Garage; Driveway; Garage Door Opener; Garage Faces Side
Patio And Porch Details: Covered Porch; Enclosed Porch; Front Porch; Rear Porch; Side Porch; Wrap Around Porch
Patio And Porch Features: Deck; Patio; Porch; Other
Possession: Close Of Escrow
Private Pool Features: Above Ground
Roof: Dimensional Style; Shingle
Sewer: Septic Tank
Showing Considerations: Pet(s) on Premises
Structure Type: House
View: Farm; Trees/Woods
Water Heater: Electric; Geothermal
Water Source: Public
Window Features: Insulated Windows; Screens
Showing Requirements: Call Listing Agent; Showing Service
Room Types: Bathroom 1; Bathroom 3; Bedroom 2; Bedroom 3; Bedroom 4; Bedroom 5; Bonus Room; Dining Room; Family Room; Foyer; Great Room; Kitchen; Office; Other; Primary Bedroom; Recreation Room; Utility Room
Room Information
Foyer
Level: First
Remarks: As you approach the home, you'll be welcomed by beautifully landscaped grounds, mature manicured trees, and an expansive covered front porch that sets the tone for the elegance found throughout the estate. Step through the front entry into a grand, light-filled foyer featuring beautiful hardwood flooring, intricate dental molding, and an expansive hallway that creates an immediate sense of warmth, sophistication, and timeless charm.
Family Room
Level: First
Remarks: The warm and inviting family room features a charming fireplace and an abundance of natural light, creating a bright, comfortable space for family and guests to enjoy.
Dining Room
Level: First
Remarks: The elegant dining room is filled with an abundance of natural light from expansive windows and is beautifully appointed with hardwood flooring, detailed dental molding, and convenient access to the butler's pantry
Kitchen
Level: First
Remarks: The heart of the home, this light-filled gourmet kitchen boasts an abundance of cabinetry, a large granite-topped center island, eat-in bar seating, and an open, inviting design perfect for entertaining while enjoying views of the surrounding countryside.
Other
Level: First
Remarks: Butler's Pantry- designed with both elegance and functionality in mind, the expansive butler's pantry features custom built-in cabinetry and seamless access to both the gourmet kitchen and formal dining room, providing exceptional storage and effortless service for entertaining guests.
Other
Level: First
Remarks: The enclosed sunroom, located just off the kitchen, creates a seamless extension of the living space, offering abundant natural light and a tranquil setting to enjoy the beauty of the countryside throughout the seasons with the Wall of elegant windows and glass doors provide direct access to the backyard paradise, creating the perfect transition to outdoor living, entertaining, and relaxation while taking in the peaceful surroundings.
Great Room
Level: First
Remarks: Rich in character and architectural appeal, the stunning two-story great room showcases a dramatic vaulted ceiling accented by exposed wood beams and a soaring floor-to-ceiling fireplace that serves as the centerpiece of the home. Anchoring the fireplace is a historic hearth featuring an original grinding stone and a mantle crafted from the property's original 1700s-era log cabin, preserving a remarkable piece of the estate's heritage. Four expansive glass doors flood the space with natural light while providing seamless access to the wraparound porch, creating an effortless connection between indoor elegance and the breathtaking Kentucky countryside.
Primary Bedroom
Level: First
Remarks: Primary - Escape to the serene ensuite, where abundant natural light highlights the timeless beauty of the clawfoot soaking tub and luxurious walk-in shower. The suite also features a private water closet with commode and bidet, along with an expansive walk-in closet appointed with a custom California Closet® system, creating the perfect blend of comfort, sophistication, and practicality. Designed as a private sanctuary, the expansive primary bedroom features an abundance of windows that fill the space with natural light and showcase picturesque countryside views, enhancing the room's warmth and tranquility.
Bathroom 1
Level: First
Remarks: Primary - Escape to the serene ensuite, where abundant natural light highlights the timeless beauty of the clawfoot soaking tub and walk-in shower. The suite also features a private water closet with commode and bidet, along with an expansive walk-in closet appointed with a custom California Closet® system, creating the perfect blend of comfort, sophistication, and practicality.
Utility Room
Level: First
Remarks: The expansive first-floor utility room is thoughtfully designed for both convenience and functionality, featuring a washer and dryer, abundant storage space, room for additional appliances, a walk-in shower, private commode room, mud sink, and a dedicated dog spa washing station, perfect for managing everyday living with ease.
Bedroom 2
Level: Second
Remarks: Abundant natural light pours into this well-appointed bedroom, highlighting the rich hardwood flooring and creating a bright, airy space designed for comfort and tranquility.
Recreation Room
Level: Second
Remarks: A standout feature of the home, the expansive recreation room boasts soaring character with exposed wood beam ceilings, gleaming hardwood floors, and classic dormer windows that flood the space with natural light. Whether envisioned as a game room, media room, music lounge, or gathering space, this remarkable room offers exceptional flexibility and charm.
Bonus Room
Level: Second
Remarks: The expansive second-floor bonus room offers exceptional potential and flexibility, featuring four charming Cape Cod-style dormer windows that fill the space with abundant natural light while adding distinctive architectural character. Already equipped with drywall, electrical, lighting, and plumbing infrastructure, this unfinished area is ready for the next owner to customize and complete according to their vision. Whether transformed into additional bedrooms, a home theater, studio, fitness area, game room, or private guest quarters, the possibilities are endless. Buyers are encouraged to verify plumbing and all intended uses to their satisfaction.
Other
Level: Second
Remarks: Music Room The distinctive second-floor music room is rich in character, featuring exposed wood beams, beautiful hardwood flooring, and a balcony overlooking the dramatic two-story great room below. Renowned for its exceptional acoustics, this unique space provides the perfect setting for musicians, vocalists, performances, creative pursuits, or simply enjoying the remarkable ambiance and architectural beauty of the home.
Kitchen
Level: Lower
Remarks: The lower-level kitchen offers a functional and convenient space, making it ideal for an in-law suite, guest quarters, or multigenerational living. Thoughtfully designed for everyday use, the kitchen includes all existing appliances, which will remain with the home, providing a turnkey opportunity for extended family or guests.
Bedroom 3
Level: Lower
Remarks: This spacious bedroom offers a comfortable retreat, featuring natural light, generous closet space, and a warm, inviting atmosphere perfect for family or guests.
Bedroom 4
Level: Lower
Remarks: This spacious bedroom offers a comfortable retreat, featuring natural light, closet space, and a warm, inviting atmosphere perfect for family or guests.
Bedroom 5
Level: Lower
Remarks: This bedroom offers a comfortable retreat, featuring natural light, closet space, and a warm, inviting atmosphere perfect for family or guests.
Office
Level: Lower
Remarks: This 6th spacious bedroom offers a comfortable retreat or great office space, featuring natural light and a warm, inviting atmosphere perfect for family or guest
Utility Room
Level: Lower
Remarks: walk-out basement door, washer, dryer, 2- water heaters, geothermal,
Bathroom 3
Level: Lower
Remarks: This well-appointed full bathroom features a tub and shower combination, double-sink vanity, and a private water closet with commode, offering both comfort and functionality for family members and guests.
Other
Level: Lower
Remarks: Designed for exceptional indoor-outdoor living, the walk-out lower level opens directly to the side yard and an extraordinary backyard retreat. Resort-style amenities include a sparkling saltwater pool, soothing hot tub, meticulously maintained landscaping, and a picturesque wraparound porch, all surrounded by the beauty and privacy of the countryside. Whether hosting guests or unwinding after a long day, this outdoor sanctuary offers an unparalleled lifestyle experience.
Listing Office:
RE/MAX Elite Lexington
Last Updated: June - 27 - 2026
Information deemed reliable but not guaranteed.


Sellers Disclosure Of Property Condition ›