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285 Hill Road, Middletown, NY, 10940

5beds
5baths
20,730sqft
$2,250,000
$109price/sqft
$19,395/moest. monthly cost
$775,800/yrincome needed

About This Home

For your consideration is 285 Hill Road, a premier equine boarding, training and showing facility formerly known as Hilltop Equestrian Center and Seven Meadows Farm. Designed for function and beauty, it's a welcoming destination for both clients and guests. Numerous shows and clinics have been successfully hosted here over the years. The property includes a professional indoor arena complex, 2 outdoor rings, second barn, 21 paddocks, 4 shedrows, 3 run-ins, a 4 bay equipment garage, and a 6,460 sf home to name a few of the many features this property offers. The spectacular indoor arena complex was built with both operational flow and refinement in mind. 8 massive Palladian windows give plenty of natural light and style to the 75x130 ring, new overhead lighting for evening lessons, sprinkler system, mirrored long side, pedestrian walkway allows foot traffic to flow, raised and heated viewing lounge to give spectators a comfy space to see the action. The attached barn has 2 brick aisleways, 13 matted stalls with swing out corner feeders, heated tack room and office, hot and cold wash stall, and a large hay loft. There are 2 outdoor sand rings with sprinkler systems, one with a hedgerow ingate - one of many classic touches around the property. The second barn, Morton built, has 15 matted stalls with swing out corner feeders, brick paver entrance and aisleway, a large heated office and plenty of adjacent turnout. There is water throughout the property. The 4 bay equipment garage is centrally located. From the top of the knoll, the stately 5 bedroom, 4 bathroom 6,460 sq federal style home overlooks it all. The home is quite spacious, and the layout suits both everyday living and entertaining with walls of windows showcasing farm views and beyond, skylights, 5 fireplaces, an expansive kitchen, and a primary suite with 2 fireplaces and a sitting room. Do you need separate space for farm managers, trainers, extended family or guests? Take advantage of a private area with a separate entrance, second kitchen with family room, full bath and large bedroom. The backyard is fenced for your pets, and has a gazebo and firepit area for even more fun! This Orange County centrally located farm is set in a lovely, upscale neighborhood close to Stewart State Forest trails, HITS, many area rated and schooling shows, Minnewaska, Mohonk, and some great local trail spots. A short drive to downtown Goshen gives you plenty of restaurants to choose from. Close to Stewart Airport and NYAIC, 60 miles to NYC and 5 miles to NJ Transit station. Goshen School District Please see attached features list for more details. This is a rare and exceptional offering for the serious equestrian entrepreneur!

Getting Around

0
WalkingCar-Dependent
0
TransitVery Limited Transit
19
BikeSomewhat Bikeable

Schools

6/10
5/10
6/10

Construction

Condition

  • Year built: 1984

Type & Style

  • Home type: SingleFamily
  • Architectural style: Colonial
  • Property subType: Single Family Residence,Residential

Interior

Appliances

  • Appliances included: Dishwasher,Dryer,Electric Oven,Electric Range,Refrigerator,Washer
  • Laundry features: Washer/Dryer Hookup,In Kitchen

Basement

  • Has basement: Yes
  • Basement: Partial

Bathroom1

  • Level: First

Bathroom2

  • Level: First

Bathroom3

  • Level: Second

Bathroom4

  • Level: Second

Bedroom1

  • Level: First

Bedroom2

  • Level: First

Bedroom5

  • Level: Second

Bedrooms & Bathrooms

  • Bedrooms: 5
  • Bathrooms: 5
  • Full bathrooms: 4
  • 1/2 bathrooms: 1

Dining Room

  • Level: First

Family Room

  • Level: First

Features

  • First Floor Bedroom,First Floor Full Bath,Ceiling Fan(s),Entrance Foyer,Formal Dining,Granite Counters,In-Law Floorplan,Primary Bathroom,Recessed Lighting
  • Number of fireplaces: 5
  • Fireplace: Yes
  • Attic: Unfinished

Heating & Cooling

  • Heating features: Baseboard
  • Cooling features: Wall/Window Unit(s)

Interior Area

  • Total structure area: 14,270
  • Total interior livable area: 20,730 sqft

Kitchen

  • Level: First

Kitchen

  • Level: First

Living Room

  • Level: First

Master Bathroom

  • Level: Second

Master Bedroom

  • Level: Second

Master Bedroom

  • Level: Second

Property

Details

  • Parcel number: 3352000600000001057.0000000
  • Special condition: None

Features

  • Patio & porch: Deck,Patio
  • Horses can be raised: Yes

Lot

  • Lot size: 28.90 Acres

Parking

  • Total spaces: 3
  • Parking features: Driveway,Garage
  • Has garage: Yes
  • Attached garage spaces: 3
  • Covered spaces: 3
  • Has uncovered spaces: Yes

Climate Risk is Financial Risk

Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.

Biggest Threats for This Home

  • Cold Wave
    Cold WaveModerate
  • Inland Flooding
    Inland FloodingModerate
  • Lightning
    LightningModerate
  • Strong Wind
    Strong WindModerate
  • Winter Weather
    Winter WeatherModerate

How This Home’s Risks Compare

Cold Wave
Inland Flooding
Lightning
Strong Wind
Winter Weather

FEMA Declared Disasters in Orange County and New York

Fire
Flood
Severe Storm

Understanding the Costs

Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.

Estimated Costs Today

MonthlyAnnual
Mortgage $11,377$136,524
Home Insurance *$806$9,672
Property Taxes $3,787$45,444
Electricity $3,425$41,109
Total$19,395$232,740
*Does not include cost of any FAIR Plan premiums

Income You'd Need if You Spent...

35% on housing$664,971/yr
40% on housing$581,850/yr
45% on housing$517,200/yr

New York FAIR Plan Programs

New York Property Insurance Underwriting Association

Covered
WildfireWildfire
HailHail
WindWind
Visit Website →
Current Policies
Residential: 20,669Commercial: 1,556
Total Premiums$32.27M
Total Exposure$7.63B

How Costs Could Change Over Time

Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.

Insurance Growth Rate5-year average: -1.9%
-1.9%
0%30.0%
Electricity Growth Rate10-year average: 7.1%
7.1%
0%15.0%
Property Taxes Growth Rate2-year average: -2.6%
-2.6%
0%15.0%
Income Spent on Housing
30%
30%45%

Comparing Against the Market

Price Per Sq Ft

$109This listing

vs Other Active Listings

Avg $/sqft

ZIP 10940$209
Orange County$275

vs Homes Sold Last Month

Median $/sqft

ZIP 10940$233
Orange County$263

Current Market Trends

Median Price Per Square Foot

The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.

Historicals for This Listing

Zestimate History ($/sqft)

No zestimate history available

Price History

DateEventPrice
2026-03-11Listed for sale$2,695,000
2026-01-01Listing removed$2,999,999
2025-06-20Listed for sale$2,999,999

For Sale by Agent

AgentHoward Hanna Rand Realty, Michelle England
BrokerageHoward Hanna Rand Realty

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