299 South Road
Ruby, NY 12475
2 Beds
3 Baths
2,868 sqft (on 24.27 acres)
2 Beds
3 Baths
2,868 sqft
(on 24.27 acres)
Home Highlights
Parking
Garage
Outdoor
Deck
Climate Control
Heating & Cooling
Price/Sqft
$418
Listed
Less than a day ago
Local Information
- Map ViewExplore the area around 299 South Road.
- Schools2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
Tucked away at the end of a long, private drive just 15 minutes from historic Kingston and 90 miles from New York City, this exceptional 24 acre compound offers a rare intersection of sleek contemporary architecture, tranquil natural beauty, and unmatched utilitarian luxury. Whether you are seeking a serene country sanctuary or a world-class estate to house a prized automotive collection, this property delivers on every level.
The heart of the property is a striking 2-bedroom, 2-bathroom contemporary home designed to pull the outdoors in. Clean lines, expansive windows, and open-concept living spaces frame views of your own private pond. The main level offers an effortless flow between the high-end kitchen and the airy living spaces--perfect for intimate weekends or stylish entertaining. A custom stone fireplace runs floor to ceiling. The first floor primary has ensuite bath with radiant floors and walks out to a deck overlooking the pond. A full, finished basement with murphy bed expands the footprint significantly, offering flexible space ideal for a media room, home gym, wine cellar, or a quiet wellness studio. Recent upgrades include new roof and gutters, furnace and hot water heater. Directly above the attached two car garage sits a bright, fully independent apartment. Featuring its own separate entrance, this auxiliary unit is perfect as a high-earning rental, a private writer's retreat, or a dedicated luxury suite for hosting weekend guests from the city.
The Automotive Pavilion & Guest Apartment For the enthusiast, the detached 5-bay garage is a crown jewel. Far beyond standard storage, this space features professional-grade infrastructure, including a hydraulic lift, soaring ceilings, and ample room for workshop customization or multi-car staging. Year round comfort with heat and a/c.
The Acreage & Location Outside, 24 pristine acres of mature woodlands offer total seclusion. Spend your mornings drinking coffee by the pond, exploring your private woods, or enjoying the local culture. The whole house generator brings peace of mind. Positioned just moments from Kingston's vibrant waterfront, boutique shops, and dining, you enjoy the absolute best of upstate privacy without ever feeling isolated.
A property of this caliber, infrastructure, and proximity to NYC is a generational find.
The heart of the property is a striking 2-bedroom, 2-bathroom contemporary home designed to pull the outdoors in. Clean lines, expansive windows, and open-concept living spaces frame views of your own private pond. The main level offers an effortless flow between the high-end kitchen and the airy living spaces--perfect for intimate weekends or stylish entertaining. A custom stone fireplace runs floor to ceiling. The first floor primary has ensuite bath with radiant floors and walks out to a deck overlooking the pond. A full, finished basement with murphy bed expands the footprint significantly, offering flexible space ideal for a media room, home gym, wine cellar, or a quiet wellness studio. Recent upgrades include new roof and gutters, furnace and hot water heater. Directly above the attached two car garage sits a bright, fully independent apartment. Featuring its own separate entrance, this auxiliary unit is perfect as a high-earning rental, a private writer's retreat, or a dedicated luxury suite for hosting weekend guests from the city.
The Automotive Pavilion & Guest Apartment For the enthusiast, the detached 5-bay garage is a crown jewel. Far beyond standard storage, this space features professional-grade infrastructure, including a hydraulic lift, soaring ceilings, and ample room for workshop customization or multi-car staging. Year round comfort with heat and a/c.
The Acreage & Location Outside, 24 pristine acres of mature woodlands offer total seclusion. Spend your mornings drinking coffee by the pond, exploring your private woods, or enjoying the local culture. The whole house generator brings peace of mind. Positioned just moments from Kingston's vibrant waterfront, boutique shops, and dining, you enjoy the absolute best of upstate privacy without ever feeling isolated.
A property of this caliber, infrastructure, and proximity to NYC is a generational find.
Last check for updates: about 12 hours ago
Listing by: Compass Greater New York, LLC, (845) 334-0227
Robert Airhart, (917) 304-3864
Source: HVCRMLS, MLS#20264191
Also Listed on HVCRMLS.
Home Details for 299 South Road
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MLS Status: Active |
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Interior Details Basement: Finished,Full |
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 4Number of Bathrooms (full): 2Number of Bathrooms (half): 2 |
Dimensions and Layout Living Area: 2868 Square Feet |
Appliances & Utilities Appliances: Washer/Dryer, Refrigerator, Range Hood, Gas Range, DishwasherDishwasherRefrigerator |
Heating & Cooling Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 1Fireplace: Great RoomHas a Fireplace |
Gas & Electric Electric: 200+ Amp Service |
Windows, Doors, Floors & Walls Flooring: Hardwood, Tile |
Levels, Entrance, & Accessibility Floors: Hardwood, Tile |
View Has a ViewView: Pond, Trees/Woods |
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Exterior Home Features Roof: AsphaltPatio / Porch: DeckOther Structures: Garage(s), WorkshopExterior: Dock, Gas Grill |
Parking & Garage Number of Garage Spaces: 9Number of Covered Spaces: 9Has a GarageNo Attached GarageParking Spaces: 9Parking: Garage |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 2268 Square FeetFinished Area (below surface): 600 Square Feet |
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Days on Market: <1 day on Trulia |
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Year Built Year Built: 1991 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Modern |
Building Not a New Construction |
Property Information Parcel Number: 5400039.0010005010.1000000 |
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Price List Price: $1,200,000Price Per Sqft: $418 |
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Direction & Address City: Ruby |
School Information High School District: Kingston Consolidated |
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Listing Agent Listing ID: 20264191 |
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Building Area Building Area: 2868 Square Feet |
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Lot Area: 24.27 Acres |
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BasementMls Number: 20264191Water ViewWater View: PondAbove Grade Unfinished Area: 2268 |
Market trends in Lake Katrine
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
7
Price History for 299 South Road
| Date | Price | Event | Source |
|---|---|---|---|
| 07/23/2026 | $1,200,000 | Listed For Sale | HVCRMLS #20264191 |
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New Listings near 299 South Road
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4.1 ACRESListing by: eXp Realty- 3.6 ACRESListing by: Berardi Realty, Active
3.26 ACRESListing by: Compass Greater New York, LLC, Active- OPEN SAT, 12-2PM2.6 ACRESListing by: Coldwell Banker Village Green, Active
5.4 ACRESListing by: The Kinderhook Group, Inc., Active- 0.5 ACRESListing by: Howard Hanna Rand Realty, Active
- OPEN SAT, 12-3PM25.18 ACRESListing by: Keller Williams Realty HV Nort, Active
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4.1 ACRESListing by: Keller Williams Realty- OPEN SAT, 11-2PM0.61 ACRESListing by: Halter Associates Realty, Active
- 29.2 ACRESListing by: Compass Greater New York, LLC, Active
- 1.18 ACRESListing by: Four Seasons Sotheby's Int., Active
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Comparable Sales for 299 South Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.22 | Single-Family Home | $770,000 | 02/05/26 | 3 | 2 | 2,100 | |
0.52 | Single-Family Home | $553,000 | 02/06/26 | 4 | 2.5 | 2,012 | |
0.66 | Single-Family Home | $450,000 | 09/16/25 | 4 | 3 | 2,850 | |
0.52 | Single-Family Home | $325,000 | 04/04/26 | 4 | 2.5 | 1,248 | |
0.57 | Single-Family Home | $410,000 | 06/12/26 | 3 | 1 | 1,840 | |
0.96 | Single-Family Home | $775,000 | 12/15/25 | 3 | 3 | 2,300 | |
0.50 | Single-Family Home | $307,616 | 12/05/25 | 3 | 1 | 1,300 | |
0.76 | Single-Family Home | $775,000 | 06/18/26 | 3 | 2 | 1,512 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
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SOLDFEB 5, 2026Compass Greater New York, LLC, Closed- OFF MARKETBerkshire Hathaway Homeservices Nutshell Realty, Closed
OFF MARKETHalter Associates Realty, Closed
OFF MARKETHoward Hanna Rand Realty, Closed
OFF MARKETBHHS HUDSON VALLEY PROP-WDST, Closed
SOLDDEC 5, 2025Amodio Real Estate & Prop, Closed
OFF MARKETKeller Williams Realty HV Nort, Closed
Assigned Schools
These are the assigned schools for 299 South Road.
- Kingston High School
- 9-12
- Public
- 1747 Students
4/10GreatSchools RatingParent Rating AverageMy son is a 2017 graduate. He graduated in top ten of the graduating class. He was captain of crew team. All honors and AP. Started the robotics club and got accepted to almost every ivy and top tier college he applied to. My point? If your kid has been taught the correct priorities and wants to succeed he or she will get a top notch education. If they don’t have support from their parents and taught the importance of education they will end up doing drugs sitting on Broadway wall. Get involved in your own child’s curriculum. Teachers can’t do it all even teachers as devoted as those at KHS.Parent Review8y ago - E R Crosby Elementary School
- K-4
- Public
- 311 Students
6/10GreatSchools RatingParent Rating AverageExceptional school. It is a true neighborhood school with high standards and a nurturing touch. So much thoughtfulness and experience. The dedication of the Principal, admin, staff, teachers, custodians is unmatched. We adore this precious gem. My child is highly sensitive and bright. So much care is given to helping him thrive.Parent Review1y ago - M Clifford Miller Middle School
- 5-8
- Public
- 826 Students
3/10GreatSchools RatingParent Rating AverageMy child is just finishing her second year at Miller and we have had a wonderful experience. Middle school is so hard for any kid due to major developmental milestones but the majority people who work there care deeply about teaching and caring for the students. A warm and kind Principal, teachers who are on the cutting edge of teaching philosophies, staff who go above and beyond even driving kids to and from extracurricular activities so they don’t miss out. Getting very involved as a positive parent partner is what works best. So grateful for the caring nursing staff, the incredible counselors, the arts and music educators and the many people who take on more than their responsibilities. So happy there.Parent Review1y ago 
Check out schools near 299 South Road.
What Locals Say about Lake Katrine
At least 22 Trulia users voted on each feature.
87 % Say car is needed
83 % Say parking is easy
78 % Say it's quiet
71 % Say there's holiday spirit
63 % Say people would walk alone at night
60 % Say yards are well-kept
59 % Say there's wildlife
58 % Say it's dog friendly
56 % Say kids play outside
54 % Say they plan to stay for at least 5 years
48 % Say neighbors are friendly
29 % Say streets are well-lit
25 % Say it's walkable to grocery stores
18 % Say it's walkable to restaurants
15 % Say there are sidewalks
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Robert Airhart, Compass Greater New York, LLC, (845) 334-0227
Agent Phone: (917) 304-3864
IDX information © 2026 by the Hudson Valley Catskill Region MLS. All Rights Reserved.
The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS.
Information is deemed reliable but is not guaranteed accurate by the MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information is deemed reliable but is not guaranteed accurate by the MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
299 South Road, Ruby, NY 12475 is a 2 bedroom, 4 bathroom, 2,868 sqft single-family home built in 1991. This property is currently available for sale and was listed by HVCRMLS on Jul 23, 2026. The MLS # for this home is MLS# 20264191.