299 South Road, Ruby, NY 12475
Property image
Property image
FOR SALE
24.27 ACRES

$1,100,000

Original price: $1,200,000
  • 2 Beds
  • 3 Baths
  • 2,868 sqft (on 24.27 acres)

299 South Road, Ruby, NY 12475

Est. Mortgage $7,406/mo*
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Home Highlights

Single-Family Home
Built in 1991
24.27 acre lot
$384/sqft
Garage

Local Information

  • Map ViewExplore the area around 299 South Road.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Expansive windowsClean linesPrivate pondDeck overlooking the pondOpen-concept living spacesSleek contemporary architecture
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.
Last check for updates: about 13 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

Interior Features

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

Exterior Features

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

Days on Market

Days on Market: 94

Property Information

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

Price & Status

Price
List Price: $1,100,000Price Per Sqft: $384

Active Status

MLS Status: Active

Location

Direction & Address
City: Ruby
School Information
High School District: Kingston Consolidated

Agent Information

Listing Agent
Listing ID: 20264191

Building

Building Area
Building Area: 2868 Square Feet

Lot Information

Lot Area: 24.27 Acres

Miscellaneous

BasementMls Number: 20264191Water ViewWater View: PondAbove Grade Unfinished Area: 2268

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Lake Katrine

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 71% say there's holiday spirit
  • 48% say neighbors are friendly
  • 15% say there are sidewalks
Trulia Trick or TreatStart Ghost Hunt
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.
  • Johnbman033
    "Back roads with lots of construction. Reallly out of the way and hard to get to. Best part is there are no tolls so I guess that’s a plus. "
    0
    Flag
  • Jolie D.
    "This is a warm and friendly area to live. The crime rate is low and I feel safe. It’s also very close to shopping and medical offices."
    0
    Flag
  • Cdale15375
    "Everyone looks out for each other Nice neighborhood Great family neighborhood Peaceful Close to schools"
    1
    Flag
  • Sarah A.
    "this is a small suburban neighborhood located just off of the business section of Kingston. It is quaint and just a couple minutes drive from any business or store that one needs to get to."
    2
    Flag
  • Diane M.
    "The neighborhood has about 200 homes. It is very safe. Many people walk, bike run or walk their dogs. It is very close to shopping and major roads but feels tucked away. "
    0
    Flag
  • Cynthia
    "Great Friendly Area, Perfect for families, retirees, couples, anyone... neighbors are great, convenient location to everything, no crimes ever, everyone watches out for everyone. very caring and nuturing neighborhood. kids still play flashlight tag at night. very safe neighborhood. you will love it here."
    0
    Flag

Market trends in Lake Katrine

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
8
1MoM
Sourced by Trulia Market Trends

Home Value

Trulia Estimate
$1.03M
Since last month
Increased$8K (+0.7%)
Since last year
Decreased$124K (-10.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value decreased by -11% in the last 10 years
MonthEstimated value
2026
October 2026$1.03M
September 2026$1.02M
August 2026$1.12M
July 2026$1.16M

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
246 South Road, Ruby, NY
0.22
Single-Family Home
$770,000
02/05/26
3
2
2,100
15 Ruby Meadows Road, Lake Katrine, NY
0.52
Single-Family Home
$553,000
02/06/26
4
2.5
2,012
14 Parkside Drive, Lake Katrine, NY
0.52
Single-Family Home
$325,000
04/04/26
4
2.5
1,248
125 Main Street, Lake Katrine, NY
0.57
Single-Family Home
$410,000
06/12/26
3
1
1,840
205 Ruby Road, Kingston, NY
0.96
Single-Family Home
$775,000
12/15/25
3
3
2,300
1254 Main Street, Ruby, NY
0.50
Single-Family Home
$307,616
12/05/25
3
1
1,300
382 Hallihans Hill Road, Kingston, NY
0.76
Single-Family Home
$775,000
06/18/26
3
2
1,512

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
299 South Rd, Kingston, NY 12401
0.00
-
2
3
2,268
Off Market
283 South Rd, Ulster, NY 12401
0.07
-
Studio
-
980
Off Market
283 South Rd, Ulster, NY 12401
0.07
-
Studio
-
1,152
Off Market
Off South Rd, Ulster, NY 12449
0.08
-
-
-
-
Off Market
278 South Rd, Ruby, NY 12475
0.09
-
Studio
-
-
Off Market
235 South Rd, Kingston, NY 12475
0.13
$566,800
3
2
2,280
Off Market
270 South Rd, Kingston, NY 12401
0.14
$609,900
4
2.5
2,205
Off Market
290 South Rd, Kingston, NY 12401
0.15
-
-
-
-
Off Market
619 E Side Hl, Kingston, NY 12401
0.15
$388,800
3
2
1,282
Off Market
319 E Side Hl #PVT, Kingston, NY 12401
0.15
$617,800
3
1
1,344
Off Market
South Rd, Kingston, NY 12401
0.16
-
-
-
-
Off Market
260 South Rd, Kingston, NY 12401
0.16
$650,000
1
3
1,000
Recently Sold
260 South Rd, Ruby, NY 12475
0.16
$746,600
3
3.5
3,309
Off Market
321 E Side Hl #PVT, Kingston, NY 12401
0.17
$114,600
Studio
-
480
Off Market
225 South Rd, Kingston, NY 12475
0.17
$349,700
3
1
1,450
Off Market
323 E Side Hl #PVT, Kingston, NY 12401
0.17
$350,400
3
1
1,436
Off Market
329 E Side Hl #PVT, Kingston, NY 12401
0.17
$542,100
3
2
1,832
Off Market
270 South Rd, Ruby, NY 12475
0.18
-
-
-
-
Off Market
225 SOUTH RD, MILTON , NY 12547
0.18
$333,600
3
1
1,664
Off Market
266 South Road, Ruby, NY 12475
0.18
-
-
-
-
Off Market

Price and Tax history

DateEventPrice
Sep 21, 2026
Source: HVCRMLS #20264191
PriceChange
$1,100,000
Price decreased by 8%
Jul 23, 2026
Source: HVCRMLS #20264191
Listed For Sale
$1,200,000

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.

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Frequently asked questions about 299 South Road

  • What is the estimated monthly payment for 299 South Road?
    Based on a $1,100,000 list price with 20% down at today's rates, the estimated monthly payment for 299 South Road in Ruby, NY is approximately $7,561 (about $5,992 principal & interest, $1,494 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Ruby?
    Residents describe Ruby, NY as easy to park in, quiet, and well-kept. Most residents say you need a car. See homes for sale in Ruby, NY.
  • What are the closest schools to 299 South Road?
    The closest schools to 299 South Road in Ruby, NY are E R Crosby Elementary School (rated 6/10), Kingston High School (rated 4/10), M Clifford Miller Middle School (Elementary, rated 3/10).
  • What is 299 South Road estimated to be worth?
    Trulia's estimated value for 299 South Road in Ruby, NY is $1,031,600.
  • Does 299 South Road have air conditioning?
    Yes, 299 South Road in Ruby, NY has air conditioning.
  • Does 299 South Road have laundry facilities?
    Yes, 299 South Road in Ruby, NY has laundry facilities.
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.