Skip to content
27 Grosso Court, Montgomery, photo 1
View all 24 photos
27 Grosso Court, photo 2
27 Grosso Court, photo 3
27 Grosso Court, photo 4
27 Grosso Court, photo 5
27 Grosso Court, photo 6
27 Grosso Court, photo 7
27 Grosso Court, photo 8
27 Grosso Court, photo 9
27 Grosso Court, photo 10
27 Grosso Court, photo 11
27 Grosso Court, photo 12
27 Grosso Court, photo 13
27 Grosso Court, photo 14
27 Grosso Court, photo 15
27 Grosso Court, photo 16
27 Grosso Court, photo 17
27 Grosso Court, photo 18
27 Grosso Court, photo 19
27 Grosso Court, photo 20
27 Grosso Court, photo 21
27 Grosso Court, photo 22
27 Grosso Court, photo 23
27 Grosso Court, photo 24

27 Grosso Court

Montgomery, NY 12549 · Orange County

Beds
4
Baths
3
Sqft
3,300
Status
Active
On site
82 days

Know your budget before you tour. Get pre-qualified

About this home

Private 6.5-acre Victorian retreat with heated salt water pool! Tucked away on a quiet cul-de-sac, this impressive home features a dramatic two-story foyer, soaring ceilings, creates a grand first impression and leads to spacious living areas throughout the home and a flexible floor plan with exceptional potential on each floor including the walk out basement. Enjoy scenic views, generous indoor and outdoor living, and a prime location just minutes from shopping, dining, and Woodbury Common Premium Outlets. The main level features a generously sized formal dining room, ideal for entertaining, holiday gatherings, and everyday living. A private den or home office provides the perfect space for remote work, studying, or a quiet retreat. One of the home’s standout features is the expansive bonus room, larger than the primary suite and complete with its own private entrance. This versatile space offers endless possibilities, whether used for multigenerational living, guest accommodations, a second home office, a media or game room, fitness studio, or creative workspace. The spacious eat-in kitchen provides ample room for casual dining and opens directly to a deck overlooking the above ground pool and the breathtaking natural surroundings. Enjoy peaceful mornings, outdoor dining, and unforgettable sunsets while taking in the beauty and privacy of approximately 6.5 acres. The expansive property also offers room for future enhancements or expansion. A conveniently located first-floor laundry room with a utility sink adds everyday practicality and convenience. The spacious primary suite serves as a private retreat, showcasing a distinctive octagonal tray ceiling, an en-suite bathroom, and an oversized walk-in closet with abundant storage. The walk-out basement expands the home’s possibilities by providing direct access to the outdoor patio, creating a seamless connection between indoor and outdoor living while offering additional space for recreation, entertaining, or future finishing. The shed presents an exciting opportunity to create a charming pool cabana, hobby space or workshop. Additional highlights include above-ground oil heating and an attached two-car garage. Whether you’re searching for privacy, versatility, scenic surroundings, or room to grow, this exceptional Victorian estate offers a rare opportunity to create the lifestyle you’ve been dreaming of. Make an appointment for a private tour and experience this beauty for yourself!

Listed with RE/MAX Distinguished Hms.&Prop · Camelia A. Pena-Rivera · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 17, 2026, 9:07 PM ET. ©2026 One Key MLS.

Estimate Your Monthly Payment

Estimate your mortgage payment, including the principal and interest, taxes, insurance, HOA, and Private Mortgage Insurance.

$4,911.23Total / mo

Estimated Monthly Payment

Principal & interest
$3,566.23 (72.6%)
Taxes
$1,145.00 (23.3%)
Insurance
$200.00 (4.1%)

Representative rates

Representative rates only, indicative for comparison. Edit the interest rate for your own quote; your lender’s numbers vary with credit, points, and insurance.

Never miss a property

Be the first to know when a Orange County home hits the market.

Save this search

Market Insights

The market around Montgomery, NY

Current Listings

New in the last 30 days

14

Sep 2026

Average Price

Active listings

$941,903

Sep 2026

Average Days on Market

Active listings

219 days

Sep 2026

Computed from 68 active OneKey MLS listings in Montgomery, NY.

Similar homes in Orange County

See all 909
110-112 S Jacqueline Street, New Windsor, NY
Photo 1 of 6
Coming SoonNew

$619,900

5 Bed • 2 Bath

110-112 S Jacqueline Street

New Windsor, NY 12553

Listed with RE/MAX Benchmark Realty Group

7 Abbey Road, Warwick, NY
Photo 1 of 3
Coming SoonNew

$629,900

3 Bed • 2 Bath • 1,440 Sq. Ft.

7 Abbey Road

Warwick, NY 10990

Listed with Howard Hanna Rand Realty

104 Ayers Court, Montgomery, NY
Photo 1 of 43
Coming SoonNew

$529,000

3 Bed • 3 Bath • 2,504 Sq. Ft.

104 Ayers Court

Montgomery, NY 12549

Listed with KW Hudson Valley United