Westchester
Horse Properties.

Michael Winter · Sotheby’s International Realty · Licensed in New York and Connecticut

+1 (914) 525-3378

Browse Listings

Land

Usable acreage, slope, water and how much turnout you really get.

See the towns

Barns

Stalls, ventilation, wiring, footing and what it costs to run.

Talk it through

Trails

Whether a parcel connects to the riding network, and on what terms.

The associations

A horse property is bought on different terms than a house.

Michael Winter

Why a separate site

The questions are about land, water, zoning, trail access and what the barn will cost to run, and they get answered long before anyone talks about the kitchen.

I sell across Northern Westchester and Fairfield County, and I built this site for the part of that market that needs its own vocabulary. If you are looking at the rest of the region, my main site covers it.

The region

Horse country, town by town

All towns

Bedford

Westchester County

Bedford is where most conversations about Westchester horse property start. Riding here is organized around a marked trail network that crosses private land by easement, maintained by an association rather than the town, which is why the land pattern has held the way it has.

North Salem

Westchester County

North Salem is the most consistently equestrian town in the county. Properties tend toward working acreage rather than manicured grounds, and the trail system runs across the state line into Ridgefield.

Pound Ridge

Westchester County

Wooded, quiet, and bordered by the county's largest park. Pound Ridge suits buyers who want privacy and terrain more than open pasture, and the reservation next door puts a large trail system within hacking distance of parts of town.

Katonah and Lewisboro

Westchester County

Katonah gives you a real village and a train station; Lewisboro, next door, gives you the land. Buyers who want a barn without giving up walkable errands tend to end up looking at both.

Armonk

Westchester County

The shortest drive to the city of the northern Westchester horse towns, and the one that reads least rural. Land here is more likely to come as a few acres than as a farm, which suits people who keep one or two horses at home and board the rest.

Chappaqua

Westchester County

Chappaqua is a village-and-schools town first. Horse property exists on its edges rather than at its center, and buyers here are usually weighing commute and community against how much land they actually need.

Before you buy

Six things that decide whether a property works

None of this is exotic. It is the list I walk with every buyer, and it is the reason a property that photographs beautifully sometimes does not survive a second visit.

01
The land, before the house
Usable acreage is not total acreage. Slope, wetlands, ledge and treeline decide how much turnout you actually get, and a survey tells you more about a horse property than a floor plan does.
02
Trail access is not automatic
In this region the riding networks cross private land by easement and are maintained by member associations. Whether a given parcel connects, and on what terms, is a question to ask before you make an offer.
03
What the town allows
Permitted animal counts, setbacks for barns and manure storage, indoor arena coverage and commercial boarding all sit in local zoning and vary town to town. Confirm with the town, in writing, for the specific parcel.
04
Water, footing and power
Well yield has to carry the house and the barn. Ask about frost-free hydrants, arena footing and base, drainage, generator capacity, and how the driveway handles a hay delivery in February.
05
The barn's real condition
Age of wiring, ventilation, stall size and matting, water and heat lines, and whether the run-in and fencing are sound. A barn inspection is a different scope from a house inspection and worth commissioning separately.
06
How you will actually use it
Keeping two at home is a different property from running a training operation. Being clear about that early narrows the search faster than any filter.

Who to call once you are here

Vets, farriers, feed, tack, boarding and the trail associations that keep the riding networks open. A reference list, not a set of recommendations.

Open the directory

Equine Veterinarians
4 listings
Farriers
1 listing
Feed, Hay and Bedding
3 listings
Tack and Apparel
3 listings
Boarding, Training and Lessons
8 listings
Trails, Hunts and Land Trusts
10 listings

About Michael

Apparel first.
Real estate after.

Sales, marketing and brand development at Ralph Lauren, then president of Nautica, and work with Tom Ford. That work was about reading what a brand actually stands for and presenting it honestly, which turns out to be most of what selling a house well requires.

I live and work in Northern Westchester and I am licensed in both New York and Connecticut, so a search that starts in Bedford and ends in New Canaan does not have to change hands.

More about me @westchesternyhomes ↗

Testimonials

What Michael's clients say.

“I found Michael to be extremely knowledgeable and had excellent negotiation skills. His honesty was very important to me as well as his reponsiveness in answering all questions in a timely manner. I would recommend him to anyone.

Buyer

“Michael was tremendous in helping us find our new home. As first time home buyers the process and experience is eye opening and Michael’s thoughtful approach informing and guiding us through the process made it such a great experience.

First-time buyer

“My wife and I found Michael to be extremely knowledgeable and an excellent local resource. He was very patient with us and I would highly recommend him as a excellent local resource the northern Westchester and Fairfield counties region.

Buyer, Northern Westchester & Fairfield County