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Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room. First floor primary bedroom suite with Waterworks bathroom, soaking tub, two walk-in closets, balcony & home Office. Intimate Dining Room with large picture window. Eat-in country Kitchen with beamed ceiling and large picture window. Family Room with fireplace & wet bar. Screened porch with bluestone floor & electric stove. Laundry Room. 3 guest bedrooms en suite on the 2nd floor. Recreation Room over the 3-car attached garage. Walk-out lower level includes a gym, wine cellar, full bath & second laundry. Gracious long driveway affording total privacy amidst park-like grounds with beautiful perennial gardens, swimming pool, fire pit, mature plantings & forever views. Hardwood floors & high ceilings throughout. Lutron lighting. Central AC. Backup generator. Outside Surveillance Cameras. Proof of funds or letter from financial institution stating buyer qualifications required prior to confirmed appointment.

Highlights

  • Residential
  • Single Family Residence
  • Built in 1989
  • 14.81 Acre Lot
  • Waterfront
  • 3 Car Garage
  • 117 days on Market

  • Bedrooms
    4
  • Bathrooms
    5 full · 2 half
  • Year Built
    1989
  • Architectural Style
    Other
  • Construction Materials
    Wood Siding, Frame, Cedar, Shingle Siding, Redwood Siding
  • Foundation
    Concrete Perimeter
  • Garage Spaces
    3.0
  • Parking Features
    Attached
  • Living Area
    6139.0
  • Interior Features
    Entrance Foyer
  • Appliances
    Dryer, Dishwasher, Microwave, Refrigerator, Washer, Gas Cooktop, Oven, Freezer
  • Pool Features
    Gunite, Heated, In Ground, Outdoor Pool
  • Cooling
    Central Air
  • Heating
    Forced Air, Oil
  • Basement
    Full, Walk-Out Access, Partially Finished

  • Acres
    14.81
  • Lot Features
    Sloped, Cleared, Waterfront
  • Water Front
    Yes
  • Water
    Well


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Frequently Asked Questions

How do I schedule a tour of 297 Painter Hill 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 297 Painter Hill 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 297 Painter Hill Rd?

Click Ask a Question to talk with our team. You already know it is a 4 bed, 5 bath, listed for $3,950,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Roxbury, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 297 Painter Hill 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 297 Painter Hill Rd at around $26,021. 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 297 Painter Hill 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 Litchfield 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 297 Painter Hill Rd?

In most cases, yes. Whether 297 Painter Hill Rd is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Roxbury'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 297 Painter Hill Rd?

We can handle that for you. Our preferred local agent specializes in residentials in Roxbury 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 $3,950,000 with 6,139 sqft of space—that comes out to approximately $643 per square foot.

How long has this property been on the market?

297 Painter Hill Rd was listed on July 20, 2026, which means it's been on the market for 117 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 1989, making it approximately 37 years old.

What is the lot size of this property?

297 Painter Hill Rd sits on a 14.81-acre lot, which is 645,124 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Per Board of Ed
  • High: Per Board of Ed

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

What are the property taxes for 297 Painter Hill Rd?

The most recent public record shows annual property taxes for 297 Painter Hill Rd were approximately $42,515. 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 297 Painter Hill 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. Copyright 2026, SmartMLS. All rights reserved.

Last Updated: November 14, 2026 at 01:07AM | Source: SmartMLS | MLS#: 24192621