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MLS ID KEY1054616Last updated Oct 25, 2026

Single Family

221 Highland Avenue

Active · Marlboro · Ulster County, NY 12542

Bedrooms
4 Beds
Bathrooms
3 Baths
Year built
1968
Est. monthly taxes
$1,422.04
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About this home

Sophisticated, spacious, and beautifully reimagined, this exceptional 4-bedroom, 3-bath home offers approximately 3,500 square feet of beautifully finished living space in one of Marlboro’s most appealing settings. Just one mile from Benmarl Winery, the home captures the best of Hudson Valley living—space, style, and an effortless connection to the landscape. The main level is the heart of the home, with an expansive, loft-like sense of openness that allows the kitchen, dining, and living spaces to flow naturally together. A striking kitchen features deep navy cabinetry, quartz countertops, stainless steel appliances, a generous center island, and an eye-catching textured backsplash. The adjacent dining and living areas are anchored by a beautiful wood-burning stone fireplace with a substantial wood mantel, while a dramatic custom built-in library in rich blue adds both character and architectural presence. Large windows and glass doors bring in abundant natural light and create an easy connection to the outdoor spaces. Hardwood floors, thoughtful lighting, and a cohesive palette of warm natural materials and sophisticated finishes give the entire main level a polished, intentional feel. The beautifully finished lower level expands the possibilities, offering additional living and entertaining space along with bedrooms, a full bath, and flexible areas for guests, work, recreation, or everyday living. With its own generous scale and natural light, it feels like a true extension of the home rather than an afterthought. Outside, the property becomes its own private Hudson Valley retreat, with expansive lawns, mature landscaping, stone walls, multiple terraces and seating areas, and a large deck designed for relaxing and entertaining. A two-car garage adds convenience and storage. Beautifully renovated, unusually spacious, and exceptionally well located, this is a home that delivers both the sophistication of a thoughtful modern renovation and the relaxed character of the Hudson Valley. Swingset does not convey.

Listing snapshot

Days on site
35 days
Listed on MLS
Sep 30, 2026
Full baths
3
Half baths
0
Annual property tax (MLS)
$17,064.47
Tax year
2025
Area source (MLS)
Other
Listing brokerage
Compass Greater NY, LLC
MLS ID
KEY1054616
Last updated
Oct 25, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1968
Garage
Yes
Garage spaces
2
Total parking
6
Parking
Driveway, Garage, Garage Door Opener
Water source
Well
Sewer
Public Sewer
Utilities
Cable Available, Cable Connected, Electricity Available, Electricity Connected

Interior features

Heating
Forced Air
Cooling
Central Air
Interior
First Floor Bedroom, First Floor Full Bath, Breakfast Bar, Built-in Features, Ceiling Fan(s), Chandelier, Chefs Kitchen, Double Vanity, Eat-in Kitchen, Formal Dining, High Ceilings, Kitchen Island, Marble Counters, Natural Woodwork, Open Floorplan, Open Kitchen, Primary Bathroom, Master Downstairs, Recessed Lighting, Washer/Dryer Hookup
Appliances
Dishwasher, Disposal, Dryer, Gas Oven, Gas Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer
Fireplace
Yes

Exterior features

Architectural style
Exp Ranch, Hi Ranch, Raised Ranch, Ranch, Split Ranch
Construction materials
Stone, Vinyl Siding
Private pool
No

Schools (MLS)

Elementary school
Marlboro Elementary School
Elementary school district
Marlboro
Middle school
Marlboro Middle School
Middle school district
Marlboro
High school
Marlboro Central High School
High school district
Marlboro

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

Recent activity

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

Location

Marlboro · Ulster County, NY 12542Show interactive map
221 Highland Avenue

Marlboro · Ulster County, NY 12542

Google Maps directions

Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
MLS amounts are prefilled when available and can be edited. Confirm what fees include. Unknown fee frequencies cannot be converted automatically.Property expenses: MLS values where available; missing values stay blank.

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.