585 Ruddles Mill Cynthiana Road, Cynthiana, KY 41031 (MLS# 26013758)

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

Overview

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. F ... (Read more) 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.

Listing Details MLS# 26013758

Listing Information

Comp Sale YN: No
Property Sub Type: Single Family Residence

Status Change Information

Status Change Timestamp: 2026-06-27

Address

County: Harrison
Street Number: 585
Street Name: Ruddles Mill Cynthiana
Street Suffix: Road
State: KY
Zip Code: 41031
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

Contract

Original List Price: 1699000
Start Showing Date: 2026-06-27
Listing Contract Date: 2026-06-14
Listing Agreement: Exclusive Right To Sell
Occupant Type: Occupied
Office Exclusive YN: No
List Price/SqFt: 237.89

Tax Legal

MLS Area Major: 016 - Harrison County
Subdivision Name: Rural
High School District: Bourbon County - 6

Interior

Bedrooms Total: 6
Bathrooms Total: 3
Bathrooms Full: 3
Above Grade Finished Area: 5340
Below Grade Finished Area: 1802
Living Area: 7142
Living Area Source: Public Records
Basement YN: Yes
Fireplace YN: Yes
Fireplaces Total: 2
Bathrooms Half: 0
Above Grade Unfinished Area: 0
Below Grade Unfinished Area: 0
Non-Compliant Total SqFt: 0

More Information

Parking Information

Garage YN: Yes
Garage Spaces: 3
Carport YN: No

Building

Year Built: 2002
Home Warranty YN: No
Accessibility Features YN: Yes

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: Yes
Electricity Connected: Yes
Phone Available: Yes
Propane: Yes
Sewer Connected: Yes
Water Connected: Yes

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.

Amenity Fee Details

Amenity Fee YN: No

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 Level: First
Bathroom 3 Level: Lower
Bedroom 2 Level: Second
Bedroom 3 Level: Lower
Bedroom 4 Level: Lower
Bedroom 5 Level: Lower
Bonus Room Level: Second
Dining Room Level: First
Family Room Level: First
Foyer Level: First
Great Room Level: First
Kitchen Level: Lower
Office Level: Lower
Other Level: Lower
Primary Bedroom Level: First
Recreation Room Level: Second
Utility Room Level: Lower
Bathroom 1: Yes
Bathroom 3: Yes
Bedroom 2: Yes
Bedroom 3: Yes
Bedroom 4: Yes
Bedroom 5: Yes
Bonus Room: Yes
Dining Room: Yes
Family Room: Yes
Foyer: Yes
Great Room: Yes
Kitchen: Yes
Office: Yes
Other: Yes
Primary Bedroom: Yes
Recreation Room: Yes
Utility Room: Yes

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

Accessibility Features

Accessible Bedroom: Yes
Accessible Central Living Area: Yes
Accessible Closets: Yes
Accessible Common Area: Yes
Accessible Doors: Yes
Accessible Full Bath: Yes
Accessible Hallway(s): Yes
Accessible Kitchen: Yes

Appliances

Dishwasher: Yes
Dryer: Yes
Microwave: Yes
Oven: Yes
Range: Yes
Refrigerator: Yes
Self Cleaning Oven: Yes
Washer: Yes

Architectural Style

Cape Cod: Yes

Attic Features

Access Only: Yes
Finished: Yes
Floored: Yes
Storage Only: Yes

Basement

Concrete: Yes
Exterior Entry: Yes
Finished: Yes
Full: Yes
Interior Entry: Yes
Sump Pump: Yes
Walk-Out Access: Yes
Walk-Up Access: Yes

Construction Materials

Vinyl Siding: Yes

Cooling

Ceiling Fan(s): Yes
Electric: Yes
Geothermal: Yes

Exterior Features

Fire Pit: Yes
Garden: Yes
Hot Tub: Yes
Storm Door(s): Yes

Fencing

Wire: Yes
Wood: Yes

Fireplace Features

Family Room: Yes
Gas Log: Yes
Great Room: Yes
Propane: Yes

Flooring

Concrete: Yes
Hardwood: Yes
Tile: Yes
Vinyl: Yes

Foundation Details

Concrete Perimeter: Yes

Heating

Geothermal: Yes
Heat Pump: Yes
Propane Tank Leased: Yes

Horse Amenities

Pasture: Yes

Interior Features

Breakfast Bar: Yes
Ceiling Fan(s): Yes
Eat-in Kitchen: Yes
Entrance Foyer: Yes
In-Law Floorplan: Yes
Primary First Floor: Yes
Soaking Tub: Yes
Walk-In Closet(s): Yes

Laundry Features

Electric Dryer Hookup: Yes
Lower Level: Yes
Main Level: Yes
Washer Hookup: Yes

Levels

Three Or More: Yes

Lot Features

Few Trees: Yes
Landscaped: Yes
Secluded: Yes

Other Structures

Other: Yes

Parking Features

Attached Garage: Yes
Driveway: Yes
Garage Door Opener: Yes
Garage Faces Side: Yes

Patio And Porch Details

Covered Porch: Yes
Enclosed Porch: Yes
Front Porch: Yes
Rear Porch: Yes
Side Porch: Yes
Wrap Around Porch: Yes

Patio And Porch Features

Deck: Yes
Patio: Yes
Porch: Yes
Other: Yes

Possession

Close Of Escrow: Yes

Private Pool Features

Above Ground: Yes

Roof

Dimensional Style: Yes
Shingle: Yes

Sewer

Septic Tank: Yes

Showing Considerations

Pet(s) on Premises: Yes

Structure Type

House: Yes

View

Farm: Yes
Trees/Woods: Yes

Water Heater

Electric: Yes
Geothermal: Yes

Water Source

Public: Yes

Window Features

Insulated Windows: Yes
Screens: Yes

Showing Requirements

Call Listing Agent: Yes
Showing Service: Yes

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

Room Name	Level	Remarks
Foyer	First	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	First	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	First	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	First	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	First	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	First	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	First	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	First	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 ClosetÂ® 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	First	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 ClosetÂ® system, creating the perfect blend of comfort, sophistication, and practicality.
Utility Room	First	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	Second	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	Second	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	Second	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	Second	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	Lower	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	Lower	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	Lower	This spacious bedroom offers a comfortable retreat, featuring natural light, closet space, and a warm, inviting atmosphere perfect for family or guests.
Bedroom 5	Lower	This bedroom offers a comfortable retreat, featuring natural light, closet space, and a warm, inviting atmosphere perfect for family or guests.
Office	Lower	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	Lower	walk-out basement door, washer, dryer, 2- water heaters, geothermal,
Bathroom 3	Lower	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	Lower	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.

Documents

Sellers Disclosure Of Property Condition ›

Home Improvements ›

Listing Office: RE/MAX Elite Lexington

Last Updated: June - 27 - 2026

Information deemed reliable but not guaranteed.