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VALLEY CENTRAL SCHOOLS | 3 BEDS + DEDICATED HOME OFFICE | 3 PRIVATE WOODED ACRES! Tucked away on three secluded acres, this turnkey Colonial Farmhouse pairs quintessential Hudson Valley charm with MAJOR UPGRADES UNDER 5 YEARS OLD: NEW CENTRAL A/C, NEW HIGH-EFFICIENCY BOILER, NEW EXPANSIVE ENTERTAINER’S DECK, OUTDOOR JACUZZI, AND INDOOR INFRARED SAUNA. Inside, warm wide-plank wood floors and a classic brick fireplace anchor the main living space, flowing into a formal dining room and a custom country kitchen with exposed timber beams, stainless gas appliances, built-in wine cooler, and breakfast bar. Work remotely without sacrificing sleeping space in the DEDICATED MAIN-FLOOR HOME OFFICE, complemented by a first-floor laundry room and powder room. Upstairs features three generous bedrooms with solid knotty pine doors, including a primary suite with crown molding, separate walk-in shower, and a deep whirlpool soaking tub framing peaceful tree views. Step out to a resort-style backyard complete with an IN-GROUND SWIMMING POOL, stamped concrete patio, new dining deck, hot tub, attached 2-car garage, and a full basement with sauna. While designed as an idyllic primary sanctuary, the property offers proven carrying-cost relief, generating OVER $50,000/YEAR IN AIRBNB INCOME ON UNDER 75 BOOKED NIGHTS. Minutes to Winding Hills Park, historic Montgomery Village dining, and major commuter routes.

Highlights

  • Residential
  • Single Family Residence
  • Built in 1992
  • 3.0 Acre Lot
  • 2 Car Garage
  • 123 days on Market

  • Bedrooms
    3
  • Bathrooms
    2 full · 1 half
  • Year Built
    1992
  • Architectural Style
    Farmhouse, Colonial
  • Construction Materials
    Wood Siding, Frame
  • Garage Spaces
    2.0
  • Parking Features
    Driveway, Garage
  • Living Area
    2030.0
  • Interior Features
    Recessed Lighting, Beamed Ceilings, Natural Woodwork, Sauna
  • Appliances
    Dishwasher, Microwave, Refrigerator, Gas Range, Stainless Steel Appliance(s), Wine Refrigerator, ENERGY STAR Qualified Appliances
  • Flooring
    Hardwood, Ceramic Tile
  • Patio And Porch
    Patio, Deck, Porch
  • Pool Features
    In Ground, Private
  • Cooling
    Central Air
  • Heating
    Baseboard, Propane
  • Basement
    Full

  • Acres
    3.0
  • Lot Features
    Wooded, Private
  • View
    Trees/Woods
  • Utilities
    Cable Connected, Electricity Connected, Phone Connected
  • Water
    Private, Well

  • County
    Orange
  • City
    Montgomery
  • Zip Code
    12549
  • High School
    Valley Central High School
  • Middle School
    Valley Central Middle School
  • Elementary School
    Montgomery Elementary School

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Frequently Asked Questions

How do I schedule a tour of 165 Benedict Rd?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 165 Benedict Rd.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 165 Benedict Rd?

Click Ask a Question to talk with our team. You already know it is a 3 bed, 2 bath, listed for $674,999. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Montgomery, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 165 Benedict Rd?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 165 Benedict Rd at around $4,749. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 165 Benedict Rd?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Orange County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 165 Benedict Rd?

In most cases, yes. Whether 165 Benedict Rd is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Montgomery's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 165 Benedict Rd?

We can handle that for you. Our preferred local agent specializes in residentials in Montgomery and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $674,999 with 2,030 sqft of space—that comes out to approximately $333 per square foot.

How long has this property been on the market?

165 Benedict Rd was listed on July 08, 2026, which means it's been on the market for 123 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1992, making it approximately 34 years old.

What is the lot size of this property?

165 Benedict Rd sits on a 3.0-acre lot, which is 130,680 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Montgomery Elementary School
  • Middle: Valley Central Middle School
  • High: Valley Central High School

Want to see how these schools compare? Check out our Orange County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for 165 Benedict Rd?

The most recent public record shows annual property taxes for 165 Benedict Rd were approximately $10,890. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 165 Benedict Rd still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, OneKey MLS. All rights reserved.

Last Updated: November 08, 2026 at 08:27PM | Source: OneKey MLS | MLS#: 1015155