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Luxury Homes in Smithtown, NY

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23 of 65 Listings

Map

23 of 65 Listings

49Active

Luxury Homes in Smithtown, NY — Page 2

65 listings

Luxury Homes in Smithtown, NY

Hide Map

23 of 65 Listings

Map

Luxury Homes in Smithtown, NY

23 of 65 Listings

Your Smithtown agent

Joe Donofrio

Douglas Elliman Real Estate

Lic. #30DO1182050

Call Joe

49Active

Your Smithtown agent

Joe Donofrio

Douglas Elliman Real Estate

Lic. #30DO1182050

Call Joe

$2,448,000

7 bd · 7 ba · 7,946 sqft

9 Swan Place, Smithtown, NY

Tracy L. Boucher CBR · Signature Premier Properties

50Active

$2,399,000

6 bd · 5 ba · 4,375 sqft

15 The Chase, Smithtown, NY

William R. Galati · Signature Premier Properties

Price Reduced50Active

$1,599,000

4 bd · 4 ba · 4,831 sqft

29 Farm Road, Smithtown, NY

Deborah Lettieri · Signature Premier Properties

Your Smithtown agent

Joe Donofrio

Douglas Elliman Real Estate

Lic. #30DO1182050

Call Joe

14Active

$3,699,000

5 bd · 8 ba · 7,000 sqft

550 Moriches Road, Smithtown, NY

Karyn Flores GRI SFR · Compass Greater NY LLC

39Active

$1,449,000

4 bd · 3 ba · 2,912 sqft

71 Wichard Boulevard, Smithtown, NY

Michail Konstas · Signature Premier Properties

37Active

$1,500,000

3 bd · 3 ba · 3,140 sqft

1 Valleywood Court W, Smithtown, NY

Christine R. Stevens SRES · Howard Hanna Coach

Price Reduced48Active

$1,298,000

5 bd · 4 ba · 3,300 sqft

135 Oakside Drive, Smithtown, NY

Richard Parisi C2EX · Century 21 Parisi Realty

50Active

$1,099,988

5 bd · 4 ba · 3,800 sqft

23 Colonial Drive, Smithtown, NY

Jocelyn Minier · BH&G R E Realty Connect

Price Reduced26Active

$1,299,000

4 bd · 4 ba · 2,084 sqft

10 Williamsburg Drive, Smithtown, NY

Damian Ross SFR CBR · Daniel Gale Sothebys Intl Rlty

Price Reduced44Active

$1,249,000

4 bd · 3 ba · 3,051 sqft

588 E. Long Beach Road, Smithtown, NY

Bonnie Glenn · Daniel Gale Sothebys Intl Rlty

Price ReducedOpen house Sun, Nov 1 · 2:00 PM44Active

$1,450,000

5 bd · 5 ba · 4,300 sqft

29 Hamlet Woods Drive, Smithtown, NY

Yan Wong · Modern Realty and Management

33Active

$1,649,000

5 bd · 4 ba · 3,000 sqft

6 Hayloft Court, Smithtown, NY

Anthony M. Perrotta CBR SFR CRB · Signature Premier Properties

Price Reduced50Active

$2,275,000

5 bd · 4 ba · 4,578 sqft

5 Meadow Gate W, Smithtown, NY

Lisa Minuto · Compass Greater NY LLC

Price Reduced49Active

$2,145,000

4 bd · 6 ba · 6,276 sqft

55 Meadow Glen Road, Smithtown, NY

Anthony M. Perrotta CBR SFR CRB · Signature Premier Properties

Price Reduced35Active

$1,419,999

4 bd · 4 ba · 2,905 sqft

21 Wilderness Road, Smithtown, NY

Jennifer Keenan · Serhant East End LLC

46Active

$3,995,000

7 bd · 6 ba · 6,000 sqft

38 Landing Meadow Road, Smithtown, NY

Philip C. Laffey · LAFFEY REAL ESTATE

Price Reduced50Active

$1,695,000

5 bd · 6 ba · 5,000 sqft

14 Loft Road, Smithtown, NY

Richard Iorio Jr · Douglas Elliman Real Estate

49Active

$1,589,000

5 bd · 4 ba · 4,960 sqft

35 Monterrey Drive, Smithtown, NY

Kiki Liu · Signature Premier Properties

50Active

$1,279,000

4 bd · 3 ba · 2,390 sqft

8 Feather Lane, Smithtown, NY

Gregory A. Berkowitz · BERKSHIRE HATHAWAY

Price Reduced35Active

$1,250,000

6 bd · 4 ba · 4,061 sqft

10 Burham Drive, Smithtown, NY

Muharem L. Hasan · Weichert Realtors

Price Reduced19Active

$2,299,000

6 bd · 4 ba · 6,050 sqft

301 Old Mill Road, Smithtown, NY

Gregory J. Masaitis · Keller Williams Realty Elite

Price Reduced43Active

$3,750,000

3 bd · 2 ba · 1,000 sqft

357 Smithtown Boulevard, Smithtown, NY

Jaclyn Marra · Keller Williams Upstate NYProp

Price Reduced31Active

$1,599,000

4 bd · 4 ba · 3,000 sqft

597 Pulaski Road, Smithtown, NY

Rachel King · Serhant LLC

1 2 3

Listing data & MLS disclosures

OneKey MLS: The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is 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. Copyright © 2026 OneKey MLS. All Rights Reserved

Smithtown housing market

September 2026 · This period is still settling

Selling at 101.9% of asking price

Buyers here are paying above asking. MLS · 46 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 10, 2026

Median sale price: $745,000$609,000–$806,500 typical range
Sales: 11
Paid in cash: 72.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $819,500
Homes for sale: 60
Median days on market: 22 days

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 9, 2026

Median home size: 1,906 sq. ft.

Smithtown, NY community profile

Area: 15.7 sq. mi.

Source: HJN community data

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Your Smithtown agent

Joe Donofrio

Douglas Elliman Real Estate

Lic. #30DO1182050

Call Joe

Listing data & MLS disclosures

OneKey MLS: The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is 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. Copyright © 2026 OneKey MLS. All Rights Reserved

Smithtown, NY community profile

Area: 15.7 sq. mi.

Source: HJN community data

Smithtown housing market

September 2026 · This period is still settling

Selling at 101.9% of asking price

Buyers here are paying above asking. MLS · 46 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 10, 2026

Median sale price: $745,000$609,000–$806,500 typical range
Sales: 11
Paid in cash: 72.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $819,500
Homes for sale: 60
Median days on market: 22 days

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 9, 2026

Median home size: 1,906 sq. ft.