by RH Advisors

See Home Value
$1,060,000
● House - Off Market

Undisclosed Address

Smithtown, NY 11788
bedrooms
4 Beds
bathrooms
2 Baths, 1 Half Bath
square feet
2,737 Ft²
$6,653
Est. Monthly

About This Property

This exceptional 4-bedroom, 2.5-bath colonial in prestigious Smithtown School District is designed for those who create, who think deeply, who gather around ideas as much as dinner tables. Over 3,000 square feet of meticulously updated living space unfolds across custom-designed rooms. It's a place where life flourishes and creative work thrives.

Although located in Hauppague, this colonial is just minutes from Smithtown village with its dining, boutiques, and cultural offerings. The prime location manages to offer both privacy and space. The home was thoughtfully expanded from its original colonial footprint (C/O's in place) creating more stature and possibility than the typical homes in the neighborhood. Even a secret passageway from the basement to the garage reminds you this home was designed with both intentionality and joy!

The award-winning gourmet kitchen is the heartbeat of this home. Chef-grade appliances, custom cabinetry, and granite counters that stretch wide and welcoming create a space designed for both the everyday and the extraordinary. Natural light pours across surfaces thoughtfully arranged for the cook who takes their craft seriously. Picture slow Sunday mornings with coffee brewing, the island becoming the natural gathering spot as ideas flow from one open counter to the next. This kitchen doesn't just hold meals - it holds your life, your conversations, your most creative moments.

But the real heart of this home is the library. A room increasingly rare, increasingly precious. Secluded. Quiet. Built-in shelving designed to hold not just books, but a life.  Both work and leisure have space here. Where a morning's research becomes an afternoon's breakthrough. And thoughts of tonight's book recommendation has the room to become an adventure!  This is the room that says: your creativity matters. Your ideas matter. This is the place where they flourish.

The formal dining room and living room expand generously designed for as many guests as you'd want to gather. Not just for meals, but for the conversations that matter. This is where ideas are debated over wine, where stories are shared late into evening, where the conversation itself is as nourishing as the food. High ceilings throughout create an immediate sense of arrival and grace. Stylish wainscoting and a stunning custom staircase announce themselves as evidence of a home designed with intention and care. A wood-burning fireplace in the den anchors this gathering space, warm and inviting.

Upstairs, the primary suite offers an oasis for new owners.  The ensuite, spa-like primary bath offers a retreat - complete with a soaking tub.  A room where the day ends and restoration begins.  Four well-proportioned bedrooms and an elevated secondary full bath, and generous closets ensure everyone has a place that feels distinctly their own.

Updated roof, Anderson windows, pavers, and all systems current mean everything is ready for you to simply enjoy.

This is more than a beautiful colonial. It's a home built for people whose creativity matters, whose ideas matter, whose gatherings around the dinner table are really gatherings around purpose and passion. It's where creative life flourishes. Where intellectual depth is honored. Where a few surprises are in store!  This is the home where your story - your real, authentic,  story - gets richer, deeper, and decidedly more extraordinary.
Unit Size
2,737 Ft²
Days on Market
103 days
Land Size
0.38 acres
Price per sqft
$365
Property Type
House
Property Taxes
$1,743
HOA Dues
-
Year Built
1968

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Last updated: 3 months ago (OneKey MLS #KEY997445)

Price History

Date / Event Date Event Price
Aug 24, 2026 Sold
Sold
Jun 4, 2026 In contract -
In contract
May 13, 2026 Listed by Compass Greater NY LLC $999,999
Listed by Compass Greater NY LLC

Property Highlights

Garage
Parking Available
Air Conditioning
Fireplace

Building Info

Overview

    General

  • Year Built: 1968
  • Effective Year Built: 1968
  • Bedroom Count: 5
  • Bathroom Count: 4
  • Full Bathrooms: 3
  • Partial Bathrooms: 4
  • Building Condition: 6
  • Building Quality: 7
  • Construction Type: 0
  • Building Style: 5
  • Exterior Walls Type: 5
  • Interior Walls Type: 0
  • Roof Shape Type: 0
  • Roof Cover Type: 0
  • Floor Count: 200
  • Floor Cover: 0
  • Basement Type: 6
  • Basement Area: 0
  • Garage Type: 1
  • Garage Square Area: 388
  • Parking Space Count: 1
  • Patio Type: 0
  • Porch Type: 6
  • Pool Type: 10

    Dimensions

  • Lot Size Square Feet: 16,553
  • Total Building Area: 2,737
  • Building Area: 2,737
  • Building Area Measurement: L

    Heating and Cooling

  • Fireplace Count: 1
  • Air Conditioning: 0
  • Heating: 10
  • Heated Square Feet: 2,737
  • Heating Fuel Type: 6

    Utilities

  • Sewer System: 4
  • Water Service: 2

Building

  • Building Type: 0
  • Property Class: R
  • Land Acres: 0000000380
  • Standard Land Use Code: 1001
  • County Land Use Code: 210
  • Legal Description 1: 160.-4-7 *4525 LOT 189 PLEASANT GREENS SEC 4

Neighborhood

  • School District Name: Smithtown Central School District
  • School Tax School District: SMITHTOWN
  • Census Tract: 135306

Geography

  • District: 0800-1
  • Section: 160.00
  • Parcel: 0800-160.00-04.00-007.000
  • Block: 4
  • Lot: 7.000
  • Municipality: SMITHTOWN
  • Latitude: 40.8287
  • Longitude: -73.1795

    Address

  • Full Address: 299 Bow Dr
  • Address - House Number: 299
  • Address - Street Name: Bow
  • Address - Suffix Type: Dr
  • State: NY
  • City Name: Hauppauge
  • Carrier Code: C061
  • 4-Digit Zip Code: 1721
  • Zip Code: 11788

Valuation

    Tax

  • Tax Year: 2023
  • Tax Amount: $1,919,488
  • Tax Rate Code Area: 473401

    Appraisal Valuation

  • Standard Deviation: 0.2692
  • Valuation Date: Feb 14, 2024
  • Confidence Score: 61
  • Final Value: 812,393
  • High Value: 1,031,100
  • Low Value: 593,687

    Market Valuation

  • Market Total Value: $8,770
  • Market Land Value: $431
  • Market Improvement Value: $8,339

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $7,630
  • Assessed Land Value: $375
  • Assessed Improvements Value: $7,255
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Hauppauge


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Frequently Asked Questions

When was property at 299 Bow Drive built and last sold?
The property at 299 Bow Drive was built in 1968 and last sold on Jan 1, 1970 for $0.
How much is this home worth?
The estimated value of the home located at 299 Bow Drive is $1,018,873.
What are some comparable homes to 299 Bow Drive?
There are currently no comparable homes to 299 Bow Drive.

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