Smithtown, NY Homes

/42
$1,645,000

$150K PRICE DROP
- 7 Beds
- 5.5 Baths
- 6,087 Sq Ft
60 Winston Dr, Smithtown, NY 11787

FSBO. At $270 per square foot, this impressive contemporary is the best value in the Smithtown Pines! Set on a beautifully landscaped level 1.06-acre property in the desirable Hamlet of Smithtown Pines, this expansive 6,087 square foot under roof, 17-room contemporary offers an exceptional blend of space, elegance and resort-style living. Featuring 7 bedrooms, 5.5 bathrooms, and a dedicated

Derek Greene Greene Realty Group

60 Winston Dr, Smithtown, NY 11787
$700,000

Sold Oct 10, 2025

46 W Pond Ct, Smithtown, NY 11787
- 2 Beds
- 2 Baths
- 1,440 Sq Ft
- Built 1988
Last Sold Summary
- 12% Above List Price
- $486/SF
- 31 Days On Market
Current Estimated Value $719,114

Last Listing Agent Lynn Sabatelle Daniel Gale Sothebys Intl Rlty

46 W Pond Ct, Smithtown, NY 11787

Est $790,913

Not Listed For Sale

24 Grassy Pond Dr, Smithtown, NY 11787
- 3 Beds
- 2 Baths
- 1,448 Sq Ft
- Built 1964
24 Grassy Pond Dr, Smithtown, NY 11787

Last Sold Summary
- 15 Days On Market

/38
$949,000
- 3 Beds
- 2.5 Baths
- 1,823 Sq Ft
34 Aberdeen Rd, Smithtown, NY 11787

Location, Location and Location ! One of the Most Wanted Addresses in Smithtown with Hauppauge Schools plus Forest Brook Elementary. Nice Center Hall Ranch with Wood Floors Everywhere, Granite Eat in Kitchen with SS Appliances, Lots of Natural Light from Skylights, Arch Roof, Cold Central Air, Hi-Hats, Family Room with Wood Burning Fireplace, Formal Dining Room with Picture Molding, Primary

Robert Scarito Douglas Elliman Real Estate

34 Aberdeen Rd, Smithtown, NY 11787
$591,650

Sold Aug 01, 2025

64 Brooksite Dr, Smithtown, NY 11787
- 3 Beds
- 3 Baths
- 1,536 Sq Ft
- Built 1960
Last Sold Summary
- 17% Below List Price
- $385/SF
- 364 Days On Market
Current Estimated Value $805,475

Last Listing Agent Christopher Rose REALHome Services & Solutions

64 Brooksite Dr, Smithtown, NY 11787

Est $1,086,010

Not Listed For Sale

6 Fairoaks Ln, Smithtown, NY 11787
- 5 Beds
- 3.5 Baths
- 3,074 Sq Ft
- Built 1988
6 Fairoaks Ln, Smithtown, NY 11787

Last Sold Summary
- 329 Days On Market

/24
$599,990

Pending
- 3 Beds
- 2 Baths
- 1,000 Sq Ft
458 New York 111, Smithtown, NY 11787

This beautifully maintained expanded Cape offers 3 spacious bedrooms and 2 full baths, primary bedroom on the main floor for added convenience. The den/loft overlooking the living room is ideal for a home office, reading nook, or living space. The full, part finished basement provides plenty of room for recreation, storage, or future customization. A standout feature is the 2-car garage w/one bay

Theresa Murino Wolf Signature Premier Properties

458 New York 111, Smithtown, NY 11787
$835,000

Sold Sep 22, 2025

31 Sterling Ln, Smithtown, NY 11787
- 4 Beds
- 2 Baths
- 2,026 Sq Ft
- Built 1960
Last Sold Summary
- 11% Above List Price
- $412/SF
- 13 Days On Market
Current Estimated Value $852,828

Last Listing Agent Andrew Norotsky Howard Hanna Coach

31 Sterling Ln, Smithtown, NY 11787

Est $823,409

Not Listed For Sale

32 Ledgewood Dr, Smithtown, NY 11787
- 4 Beds
- 3 Baths
- Built 1955
32 Ledgewood Dr, Smithtown, NY 11787

Last Sold Summary
- 12 Days On Market

/48
$2,599,000
- 6 Beds
- 8 Baths
- 3,946 Sq Ft
2 Riverview Terrace, Smithtown, NY 11787

Paradise on the Nissequogue River with 65 feet of waterfront, ideal for canoeing, kayaking, and serene relaxation. This impressive 5,500+ sq ft contemporary with traditional accents offers 15 rooms and two fully separate living quarters, each with its own basement—perfect for extended or multi-generational living. Both residences feature updated granite eat-in kitchens with wood cabinetry and

Jamie Marcantonio Signature Premier Properties

2 Riverview Terrace, Smithtown, NY 11787
$682,000

Sold Oct 14, 2025

8 W Pond Ct, Smithtown, NY 11787
- 2 Beds
- 2.5 Baths
- 1,500 Sq Ft
- Built 1987
Last Sold Summary
- 14% Above List Price
- $455/SF
- 21 Days On Market
Current Estimated Value $640,127

Last Listing Agent gordon lewis RE/MAX Integrity Leaders

8 W Pond Ct, Smithtown, NY 11787

Est $813,007

Not Listed For Sale

10 Belford Ln, Smithtown, NY 11787
- 4 Beds
- 2 Baths
- Built 1962
10 Belford Ln, Smithtown, NY 11787

Last Sold Summary
- 7 Days On Market

/45
$1,249,000

$100K PRICE DROP Pending
- 5 Beds
- 4.5 Baths
- 3,937 Sq Ft
144 Landing Meadow Rd, Smithtown, NY 11787

Original owner, clean and well maintained 4000 square foot colonial on 1.2 acres in Point of Woods Section. Featuring 5 beds/4 baths including an ensuite bedroom with full bath on the first floor (see floor plan). Double height entry foyer with large open living spaces. Huge kitchen, dining and family room with wood burning fireplace. Full basement with outside entrance. Two car garage with long

Shahzad Qureshi Pinnacle R E Consulting Inc

144 Landing Meadow Rd, Smithtown, NY 11787
$775,000

Sold Dec 19, 2025

21 Dehan St, Smithtown, NY 11787
- 3 Beds
- 2 Baths
- 1,017 Sq Ft
- Built 1965
Last Sold Summary
- 11% Above List Price
- $762/SF
- 16 Days On Market
Current Estimated Value $776,379

Last Listing Agent Janet Pushee Coldwell Banker American Homes

21 Dehan St, Smithtown, NY 11787

Est $738,506

Not Listed For Sale

27 Morewood Dr, Smithtown, NY 11787
- 3 Beds
- 2 Baths
- 1,235 Sq Ft
- Built 1960
27 Morewood Dr, Smithtown, NY 11787

Last Sold Summary
- 10 Days On Market

/26
$699,999

Pending
- 2 Beds
- 2.5 Baths
- 1,576 Sq Ft
157 Hidden Ponds Cir, Smithtown, NY 11787

Welcome to this beautifully maintained 2-bedroom, 2.5-bath condominium located in a desirable gated community in Smithtown, offering serene pond views and an exceptional lifestyleThis inviting home features an eat-in kitchen and a stunning living room with vaulted ceilings, a cozy gas fireplace, and three skylights that fill the space with natural light. The spacious king-size primary bedroom

John Matthew Douglas Elliman Real Estate

157 Hidden Ponds Cir, Smithtown, NY 11787
$835,000

Sold Jan 16, 2026

8 Scarborough Dr, Smithtown, NY 11787
- 3 Beds
- 3.5 Baths
- 1,940 Sq Ft
- Built 2001
Last Sold Summary
- 1% Above List Price
- $430/SF
- 22 Days On Market
Current Estimated Value $831,478

Last Listing Agent Joseph Femia Signature Premier Properties

8 Scarborough Dr, Smithtown, NY 11787

Est $817,761

Not Listed For Sale

4 Norwalk Ln, Smithtown, NY 11787
- 3 Beds
- 1.5 Baths
- Built 1960
4 Norwalk Ln, Smithtown, NY 11787

Last Sold Summary
- 13 Days On Market

/42
$1,200,000

Pending
- 5 Beds
- 4.5 Baths
- 3,634 Sq Ft
99 Shirley Ct, Smithtown, NY 11787

Nestled in the highly desirable Smithtown Pines, this one-of-a-kind home offers a unique layout that's perfect for multigenerational living or for those seeking a spacious, versatile design. With five bedrooms and 4.5 baths, including two primary ensuites, this home offers exceptional accommodations - it's like getting two houses in one! The main home features a large living room that leads to an

Christine Daddio Howard Hanna Coach

99 Shirley Ct, Smithtown, NY 11787
$827,000

Sold Jan 22, 2026

311 Devon Ln, Smithtown, NY 11787
- 3 Beds
- 2 Baths
- 1,632 Sq Ft
- Built 1959
Last Sold Summary
- 12% Above List Price
- $507/SF
- 12 Days On Market
Current Estimated Value $813,391

Last Listing Agent Team Rivera Keller Williams Points North

311 Devon Ln, Smithtown, NY 11787

Est $867,020

Not Listed For Sale

11 Woodrow Ln, Smithtown, NY 11787
- 4 Beds
- 3 Baths
- 2,114 Sq Ft
- Built 1960
11 Woodrow Ln, Smithtown, NY 11787

Last Sold Summary
- 23 Days On Market

/32
$799,999

$30K PRICE DROP
- 3 Beds
- 2 Baths
- 1,328 Sq Ft
49 Sandy Hollow Dr, Smithtown, NY 11787

Welcome to this fully renovated raised ranch located in the highly desirable Commack School District, offering the perfect combination of modern design and everyday functionality. This 3 bedroom, 2 full bathroom home features a bright open concept layout with hardwood floors throughout and a stunning kitchen complete with quartz countertops, stainless steel appliance, a center island, gas

Mathias Coni Oversouth LLC

49 Sandy Hollow Dr, Smithtown, NY 11787
$650,000

Sold Nov 21, 2025

239 Pond View Ln, Smithtown, NY 11787
- 3 Beds
- 2.5 Baths
- 1,800 Sq Ft
- Built 1988
Last Sold Summary
- 10% Below List Price
- $361/SF
- 61 Days On Market
Current Estimated Value $688,153

Last Listing Agent Anna Niola Douglas Elliman Real Estate

239 Pond View Ln, Smithtown, NY 11787

Est $852,614

Not Listed For Sale

12 Dana Ln, Smithtown, NY 11787
- 4 Beds
- 1.5 Baths
- 1,800 Sq Ft
- Built 1965
12 Dana Ln, Smithtown, NY 11787

Last Sold Summary
- 21 Days On Market

/42
$1,200,000

$200K PRICE INCREASE Pending
- 4 Beds
- 2.5 Baths
- 2,500 Sq Ft
27 Winslow Ln, Smithtown, NY 11787

Welcome to 27 Winslow Lane... a Stunning Brookfield colonial with fresh updates and thoughtfully designed touches..........This home features a large entry foyer w/ an abundance of natural light, a generously sized formal living room, a formal dining room that opens into an updated EIK w/ gorgeous white cabinetry, Marble stone countertops and SS appliances, an inviting family room w/ built in

Deborah Lettieri Signature Premier Properties

27 Winslow Ln, Smithtown, NY 11787
$760,000

Sold Feb 04, 2026

58 Rhoda Ave, Smithtown, NY 11787
- 3 Beds
- 2.5 Baths
- 2,462 Sq Ft
- Built 1969
Last Sold Summary
- 5% Below List Price
- $309/SF
- 91 Days On Market
Current Estimated Value $800,229

Last Listing Agent Robert Scarito Douglas Elliman Real Estate

58 Rhoda Ave, Smithtown, NY 11787

Est $777,860

Not Listed For Sale

10 Morewood Dr, Smithtown, NY 11787
- 4 Beds
- 3 Baths
- 2,615 Sq Ft
- Built 1957
10 Morewood Dr, Smithtown, NY 11787

Last Sold Summary
- 20 Days On Market

/28
$800,000

Open Sat 12PM - 2PM
- 4 Beds
- 2 Baths
- 1,600 Sq Ft
31 Apple Ln, ComMacK, NY 11725

This stunning Craftsman-style home has been impeccably remodeled from top to bottom. Simply move right in and unpack—every detail has been thoughtfully updated and improved. Roof, windows, Hardiplank siding, stoop and driveway all done last year. Brand new hot water heater. The first floor features a spectacular modern kitchen, completely renovated in 2021. Designed with entertaining in mind, it

Melissa D'Angelo Compass Greater NY LLC

31 Apple Ln, ComMacK, NY 11725
$500,000

Sold Nov 13, 2025

41 W Pond Ct, Smithtown, NY 11787
- 2 Beds
- 1.5 Baths
- 1,129 Sq Ft
- Built 1987
Last Sold Summary
- 20% Below List Price
- $443/SF
- 41 Days On Market
Current Estimated Value $570,844

Last Listing Agent Shirley Chen Prime Realty

41 W Pond Ct, Smithtown, NY 11787

Est $774,188

Not Listed For Sale

12 Parnell Dr, Smithtown, NY 11787
- 3 Beds
- 2 Baths
- 1,834 Sq Ft
- Built 1963
12 Parnell Dr, Smithtown, NY 11787

Last Sold Summary
- 9 Days On Market

/40
$1,200,000

Open Sat 11AM - 1PM
- 6 Beds
- 2.5 Baths
- 3,217 Sq Ft
21 Fairoaks Ln, Smithtown, NY 11787

Welcome to this beautifully upgraded and meticulously maintained home in the prestigious Smithtown Pines, offering an impressive blend of comfort and style.The main living area showcases stunning molding work throughout with coffered ceilings and gas fireplace.. cherrywood hardwood flooring in the master bedroom and a hallway bathroom complete with a luxurious jet soaking tub. One of the

Joseph Donofrio Douglas Elliman Real Estate

21 Fairoaks Ln, Smithtown, NY 11787
$900,000

Sold Nov 03, 2025

3 Everit Place, Smithtown, NY 11787
- 3 Beds
- 2.5 Baths
- 1,300 Sq Ft
- Built 1961
Last Sold Summary
- $692/SF
- 7 Days On Market
Current Estimated Value $885,136

Last Listing Agent Bryan Karp Coldwell Banker American Homes

3 Everit Place, Smithtown, NY 11787

Est $757,741

Not Listed For Sale

16 Parnell Dr, Smithtown, NY 11787
- 3 Beds
- 2 Baths
- 1,051 Sq Ft
- Built 1963
16 Parnell Dr, Smithtown, NY 11787

Last Sold Summary
- 50 Days On Market

/29
$1,250,000

New Construction Pending
- 5 Beds
- 3.5 Baths
- 3,134 Sq Ft
2 Sycamore Place, Smithtown, NY 11787

THE DORCHESTER (3134 SF): 5bdrm-3.5ba Classic Center Hall Colonial. Features include spanning Master Suite, 2-story foyer and great rooms, office/guest quarters/ensuite on the 1st floor, front or side entry 2-car garages. The full basement with outside entrance offers an addt'l ~1,700 SF of space. Sycamore Estates is an 18-home new development consisting of 3 privately sidewalked cul-de-sacs

Paul Musso Realty Connect USA L I Inc

2 Sycamore Place, Smithtown, NY 11787
$875,000

Sold Jul 30, 2025

8 Clover Dr, Smithtown, NY 11787
- 4 Beds
- 2 Baths
- 2,600 Sq Ft
- Built 1961
Last Sold Summary
- $337/SF
- 12 Days On Market
Current Estimated Value $923,015

Last Listing Agent Christine Daddio Howard Hanna Coach

8 Clover Dr, Smithtown, NY 11787

Est $816,691

Not Listed For Sale

30 Rogers Ln, Smithtown, NY 11787
- 4 Beds
- 2 Baths
- Built 1962
30 Rogers Ln, Smithtown, NY 11787

Last Sold Summary
- 44 Days On Market

/43
$849,990

Pending
- 4 Beds
- 2.5 Baths
- 1,788 Sq Ft
12 Westbrook Ln, Smithtown, NY 11787

GOING....GOING.... GONE......!!Don't blink or you will miss this one. Completely renovated in 2017. Hardwood floors throughout. 4 good sized bedrooms with 2 full baths on 2nd floor. Finished basement and attached 1 car garage. 1/4 acre midblock location on fully fenced yard. This is the one you have been waiting for. Taxes under $10K with basic star!!!!

Matthew Wynn Signature Premier Properties

12 Westbrook Ln, Smithtown, NY 11787
$759,000

Sold Mar 19, 2026

16 E Hill Dr, Smithtown, NY 11787
- 3 Beds
- 2 Baths
- 1,093 Sq Ft
- Built 1959
Last Sold Summary
- 1% Above List Price
- $694/SF
- 37 Days On Market
Current Estimated Value $750,548

Last Listing Agent Elizabeth Kee Core Long Island LLC

16 E Hill Dr, Smithtown, NY 11787

Est $838,114

Not Listed For Sale

5 Greenwich Rd, Smithtown, NY 11787
- 3 Beds
- 4 Baths
- 1,704 Sq Ft
- Built 1961
5 Greenwich Rd, Smithtown, NY 11787

Last Sold Summary
- 5 Days On Market

/46
$999,000

Pending
- 4 Beds
- 3.5 Baths
- 2,365 Sq Ft
1 Regal Ct, Saint James, NY 11780

Welcome Home to this meticulous Colonial featuring hardwood floors throughout and exceptional updates inside and out. Set on a beautifully landscaped, fully fenced property, this home offers the perfect blend of comfort, space, and entertaining amenities. Highlights include vinyl siding just 3 years young, oil tank 5 years young, separate hot water heater, CAC with heat pump, alarm system, IGS,

Lisa Corwin Howard Hanna Coach

1 Regal Ct, Saint James, NY 11780

Showing Results 161 - 200, Page 5 of 18

New York Suffolk County Smithtown

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