Smithtown, NY Homes

/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
$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 $785,268

Last Listing Agent Janet Pushee Coldwell Banker American Homes

21 Dehan St, Smithtown, NY 11787

Est $1,004,198

Not Listed For Sale

41 Grassy Pond Dr, Smithtown, NY 11787
- 3 Beds
- 3 Baths
- 3,153 Sq Ft
- Built 1965
41 Grassy Pond Dr, Smithtown, NY 11787

Last Sold Summary
- 12 Days On Market
Last Listing Agent Elisabeth Marino HomeSmart Premier Living Rlty

/36
$990,000
- 4 Beds
- 2.5 Baths
- 2,411 Sq Ft
19 Eckernkamp Dr, Smithtown, NY 11787

Set on a beautifully landscaped 0.80-acre corner property, this custom Farm Ranch offers space, comfort, and exceptional versatility. A welcoming entry foyer opens to a recently renovated eat-in kitchen featuring a striking double-sided fireplace. The bright and airy den is surrounded by walls of windows, while the formal dining room provides easy access to the deck through sliding glass doors.

Michelle Wright Signature Premier Properties

19 Eckernkamp Dr, 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 $841,545

Last Listing Agent Joseph Femia Signature Premier Properties

8 Scarborough Dr, Smithtown, NY 11787

Est $962,784

Not Listed For Sale

33 Grassy Pond Dr, Smithtown, NY 11787
- 5 Beds
- 3.5 Baths
- Built 1976
33 Grassy Pond Dr, Smithtown, NY 11787

Last Sold Summary
- 21 Days On Market
Last Listing Agent Elia Rubinstein Realty Connect USA L I Inc

/32
$749,999

$80K 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
$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 $827,689

Last Listing Agent Team Rivera Keller Williams Points North

311 Devon Ln, Smithtown, NY 11787

Est $964,364

Not Listed For Sale

25 Grassy Pond Dr, Smithtown, NY 11787
- 4 Beds
- 2.5 Baths
- 2,048 Sq Ft
- Built 1968
25 Grassy Pond Dr, Smithtown, NY 11787

Last Sold Summary
- 17 Days On Market
Last Listing Agent Debbie Herman American Way Real Estate Inc

/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
$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 $690,242

Last Listing Agent Anna Niola Douglas Elliman Real Estate

239 Pond View Ln, Smithtown, NY 11787

Est $975,557

Not Listed For Sale

51 Woodland Ln, Smithtown, NY 11787
- 5 Beds
- 2.5 Baths
- 2,222 Sq Ft
- Built 1970
51 Woodland Ln, Smithtown, NY 11787

Last Sold Summary
- 8 Days On Market
Last Listing Agent Christine Daddio Howard Hanna Coach

/28
$800,000

Pending
- 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
$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 $808,045

Last Listing Agent Robert Scarito Douglas Elliman Real Estate

58 Rhoda Ave, Smithtown, NY 11787

Est $1,073,193

Not Listed For Sale

47 Woodland Ln, Smithtown, NY 11787
- 4 Beds
- 3 Baths
- 2,222 Sq Ft
- Built 1972
47 Woodland Ln, Smithtown, NY 11787

Last Sold Summary
- 23 Days On Market
Last Listing Agent Mohamed Elbaroudy Redfin Real Estate

/23
$905,000
- 4 Beds
- 2.5 Baths
22 S Lot Rd, Smithtown, NY 11787

Pristine and sophisticated, this beautifully customized 4-bedroom, 2.5-bath ranch offers a spectacular open-concept design perfect for today's lifestyle. Originally built in the 1960s, the home has been thoughtfully updated over the years to reflect timeless elegance and exceptional craftsmanship. The stunning center island kitchen features a dramatic 7-foot black granite island, Sub-Zero

Linda Sauerbrey Daniel Gale Sothebys Intl Rlty

22 S Lot Rd, Smithtown, NY 11787
$1,270,000

Sold Aug 10, 2026

99 Shirley Ct, Smithtown, NY 11787
- 5 Beds
- 4.5 Baths
- 3,634 Sq Ft
- Built 1966
Last Sold Summary
- 6% Above List Price
- $349/SF
- 27 Days On Market
Current Estimated Value $1,197,646

Last Listing Agent Christine Daddio Howard Hanna Coach

99 Shirley Ct, Smithtown, NY 11787

Est $1,349,553

Not Listed For Sale

45 Woodland Ln, Smithtown, NY 11787
- 5 Beds
- 4.5 Baths
- 3,448 Sq Ft
- Built 1971
45 Woodland Ln, Smithtown, NY 11787

Last Sold Summary
- 14 Days On Market
Last Listing Agent Christine Daddio Howard Hanna Coach

/40
$1,200,000

Pending
- 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
$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 $568,720

Last Listing Agent Shirley Chen Prime Realty

41 W Pond Ct, Smithtown, NY 11787

Est $800,238

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
Last Listing Agent Christine Daddio Howard Hanna Coach

/50
$775,000
- 3 Beds
- 1.5 Baths
- 1,632 Sq Ft
20 Brook Ln, Smithtown, NY 11787

WHERE TIMELESS CHARM MEETS EXCEPTIONAL OPPORTUNITY.Discover the warmth, character, and enduring appeal of this beautifully maintained Colonial, ideally situated in one of Smithtown’s most desirable neighborhoods. Rich hardwood floors, an inviting fireplace, and flowing floor plan create an atmosphere that feels instantly like home. Offering three spacious bedrooms and one-and-a-half baths,

Jann Oberg Signature Premier Properties

20 Brook 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 $869,374

Last Listing Agent Bryan Karp Coldwell Banker American Homes

3 Everit Place, Smithtown, NY 11787

Est $1,128,307

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
Last Listing Agent Jonathan Minerick HomeCoin.com

/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
$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 $754,311

Last Listing Agent Elizabeth Kee Core Long Island LLC

16 E Hill Dr, Smithtown, NY 11787

Est $834,630

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
Last Listing Agent Allyson Bruetsch Long Island Home Prop LLC

/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
$660,000

Sold Sep 08, 2025

60 Tanglewood Dr, Smithtown, NY 11787
- 3 Beds
- 1 Bath
- Built 1957
Last Sold Summary
- 10% Above List Price
- 27 Days On Market
Current Estimated Value $694,619

Last Listing Agent Gail Carillo Coldwell Banker American Homes

60 Tanglewood Dr, Smithtown, NY 11787

Est $803,074

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
Last Listing Agent Ronni Tranes Coldwell Banker American Homes

/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
$925,000

Sold Jun 16, 2026

7 Quincy Ln, Smithtown, NY 11787
- 4 Beds
- 3 Baths
- 2,183 Sq Ft
- Built 1973
Last Sold Summary
- 9% Above List Price
- $424/SF
- 13 Days On Market
Current Estimated Value $891,770

Last Listing Agent Deborah Lettieri Signature Premier Properties

7 Quincy Ln, Smithtown, NY 11787

Est $754,782

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
Last Listing Agent Geralda Desir Goldcrest Realty Group LLC

/2
$979,000
- 4 Beds
- 2.5 Baths
- 2,138 Sq Ft
30 Glacier Dr, Smithtown, NY 11787

Under Construction – Your Opportunity to Own a Beautifully Renovated Home in Smithtown! Welcome to this stunning 4-bedroom, 2.5-bath splanch, currently under a full renovation with today's modern buyer in mind. Upon completion, this home will feature a spacious and modern layout with high-quality finishes throughout. With the main floor having a Beautiful modern kitchen and a formal dining room.

Alvaro Dumancela Douglas Elliman Real Estate

30 Glacier Dr, Smithtown, NY 11787
$650,000

Sold Feb 27, 2026

32 Scarborough Dr, Smithtown, NY 11787
- 2 Beds
- 2.5 Baths
- 1,358 Sq Ft
- Built 2001
Last Sold Summary
- 9% Above List Price
- $479/SF
- 15 Days On Market
Current Estimated Value $660,442

Last Listing Agent Cynthia Zwirba Douglas Elliman Real Estate

32 Scarborough Dr, Smithtown, NY 11787

Est $838,126

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
Last Listing Agent Kevin Collins Signature Premier Properties

/29
$749,990
- 3 Beds
- 2 Baths
- 1,194 Sq Ft
271 Terry Rd, Smithtown, NY 11787

Nestled on over half an acre of beautifully manicured property, 271 Terry Road in Smithtown offers charm, flexibility, and exceptional indoor-outdoor living. This well-maintained home features a thoughtfully designed layout with a finished basement that includes a private outside entrance, a full designer bathroom, office space, additional living area, laundry area, wet bar, walk-in closet, extra

Luis Dominguez Island Advantage Realty LLC

271 Terry Rd, Smithtown, NY 11787
$740,000

Sold Jun 01, 2026

12 Stone Gate Ct, Smithtown, NY 11787
- 3 Beds
- 3 Baths
- 1,805 Sq Ft
- Built 1993
Last Sold Summary
- 1% Above List Price
- $410/SF
- 19 Days On Market
Current Estimated Value $746,448

Last Listing Agent Lina Lopes Douglas Elliman Real Estate

12 Stone Gate Ct, Smithtown, NY 11787

Est $864,765

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
Last Listing Agent Michael Scarito RE/MAX Integrity Leaders

/18
$500,000

Pending
- 3 Beds
- 1 Bath
- 1,014 Sq Ft
20 Croft Ln, Smithtown, NY 11787

This 3-bedroom, 1-bath ranch is located in the Smithtown Pines. This charming home has a living room, an eat-in kitchen, a den with a laundry closet, an office, three bedrooms, and a bathroom. Full unfinished basement. Other features are: 100 amp electrical service, one-car garage, central air, and flat.74 acres. This home is being sold in as-is condition with all contents of the home included.

Christine Daddio Howard Hanna Coach

20 Croft Ln, Smithtown, NY 11787

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