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MLS ID KEY966893Last updated Aug 26, 2026

Single Family

14 Hillside Avenue

Pending · Smithtown · Suffolk County, NY 11780

Bedrooms
4 Beds
Bathrooms
3 Baths
Year built
1968
Est. monthly taxes
$1,451.34
Property gallery0 / 30
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About this home

Huge Price Reduction — Opportunity of a Lifetime! Set on 1.25 beautifully maintained, level acres within the highly desirable community of St. James, this exceptional property offers the perfect balance of space, privacy, and versatility — with a rare equestrian component that elevates it beyond the ordinary! The impeccably maintained Center Hall Colonial features 4 bedrooms and 2.5 baths with a gracious, flowing floor plan designed for both comfortable everyday living and effortless entertaining. Rich wood floors run throughout the home, complemented by tasteful neutral decor and abundant natural light. The custom updated eat-in kitchen is thoughtfully appointed with stainless steel appliances, granite countertops, and a charming dinette area overlooking the expansive property — creating a seamless indoor-outdoor connection. Formal living and dining rooms provide an elegant gathering space, while the warm and inviting den has a wood burning fireplace and offers a cozy retreat. The primary bedroom features a private ensuite bath, and three additional generously sized bedrooms complete the second level. Updated windows and bathrooms, central air conditioning, a full finished basement with outside entry, and a two-car garage enhance everyday convenience. Additional improvements include low-maintenance vinyl siding, and a generator transfer switch for added peace of mind. Pride of ownership is evident throughout. For those seeking additional flexibility, the property is thoughtfully equipped for equestrian use. A center aisle working barn includes four 12x10 matted breeding stalls, 50-amp electric service, water, heat and ventilation fans, loft exhaust system, and phone lines. Outdoor amenities feature a riding ring with lighting, sprinkler system for dust control, paddock and grazing areas, wash rack, and full secondary fencing. The grounds provide a private and versatile environment suitable for training, conditioning, or leisure riding — all within the comfort of your own property. Located within the Smithtown School District, this unique property is just minutes from shopping, restaurants, parks, transportation, Stony Brook University, Stony Brook Hospital, and the beaches of the Long Island Sound. Offering a rare combination of space, flexibility, and convenience, this exceptional St. James property presents an outstanding opportunity to create something truly special. Whether enjoyed as-is or tailored to suit your vision, this remarkable offering is ready for its next chapter. Must see to appreciate.

Listing snapshot

Days on site
59 days
Listed on MLS
Mar 5, 2026
Full baths
2
Half baths
1
Annual property tax (MLS)
$17,416.13
Tax year
2026
Listing brokerage
Daniel Gale Sothebys Intl Rlty
MLS ID
KEY966893
Last updated
Aug 26, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1968
Garage
Yes
Garage spaces
2
Parking
Driveway, Garage
Water source
Public
Sewer
Cesspool
Utilities
Cable Available, Electricity Connected, Phone Connected, Trash Collection Public

Interior features

Basement
Full, Unfinished, Walk-Out Access
Heating
Hot Water, Oil
Cooling
Central Air
Interior
First Floor Full Bath, Chefs Kitchen, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, Pantry, Primary Bathroom, Recessed Lighting, Storage, Walk-In Closet(s), Washer/Dryer Hookup
Appliances
Dishwasher, Dryer, Electric Oven, Electric Range, ENERGY STAR Qualified Appliances, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Oil Water Heater
Flooring
Carpet, Hardwood, Laminate
Fireplace
Yes
Fireplaces
1

Exterior features

Architectural style
Colonial
Construction materials
Brick, Frame, Vinyl Siding
Exterior
Mailbox
Private pool
No

Schools (MLS)

Elementary school
Mills Pond Elementary School
Elementary school district
Smithtown
Middle school
Great Hollow Middle School
Middle school district
Smithtown
High school
Smithtown High School-East
High school district
Smithtown

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

  1. First seen on this site
  2. Listing updated from MLS
  3. MLS status changed

Location

Smithtown · Suffolk County, NY 11780Show interactive map
14 Hillside Avenue

Smithtown · Suffolk County, NY 11780

Google Maps directions

Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
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Estimated monthly principal & interest—

Monthly property taxNot provided

Monthly association / maintenance feesNot provided

Estimated monthly total of entered costs—

Excludes insurance, mortgage insurance, special assessments and lender fees. MLS taxes may reflect abatements or exemptions and can change.

Listing data is supplied by the MLS and may change without notice.