Head of the Harbor, NY homes for sale & real estate

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1 Meadow Gate East, Head Of The Harbor, NY 11780
1 Meadow Gate East, Head Of The Harbor, NY 11780
1 Meadow Gate East, Head Of The Harbor, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Welcome to 1 Meadow Gate East. .. .A Stunning Estate with endless possibilities, set on 2 beautiful acres in the desirable Incorporated Village of Head of the Harbor! As you step through the elegant front doors, you’re welcomed by a bright and inviting atmosphere, w/ natural light pouring in and peaceful views of the natatorium w/ Resort style Indoor Premium PebbleTec Pool, offering a perfect mix of comfort and flexibility. The spacious 5-bedroom, 5-and-a-half-bathroom layout includes a Gorgeous Chefs kitchen with high-end Stainless steel Appliances Appliances, a Crawford ceiling, and a stone fireplace, seamlessly flowing into the oversized Family Room. All bathrooms have been thought

$2,680,000

5 beds5.5 baths10,000 sq ft

1 Meadow Gate East, Head Of The Harbor, NY 11780

2 acre lot • $23 HOA • 3 garage spots

Listing by Signature Premier Properties

17 Barn Ln, Head Of The Harbor, NY 11780
17 Barn Ln, Head Of The Harbor, NY 11780
17 Barn Ln, Head Of The Harbor, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
A Stunning home, nestled on 2 acres, offering incredible attention to detail. The open floor plan offers in excess of 5000 ft. with five bedrooms and 4 1/2 baths. Upon arrival, you are greeted by a gracious two-story entryway leading to a dramatic great room with gas fireplace and double-height coffered ceiling. The formal living room and dining room have 9 foot ceilings and an abundance of natural light. Oversized chef's kitchen provides a breakfast nook, serving area, coffee bar, and pantry. A guest suite, office and laundry round out the main level. Both staircase lead to the second level where you will find a well appointed primary suite. The space includes fireplace, walk-in closets an

$2,900,000

5 beds4.5 baths5,340 sq ft

17 Barn Ln, Head Of The Harbor, NY 11780

2 acre lot • 3 garage spots • Car-dependent

Listing by Daniel Gale Sothebys Intl Rlty

3D WALKTHROUGH

537 Moriches Rd, Head Of The Harbor, NY 11780
537 Moriches Rd, Head Of The Harbor, NY 11780
537 Moriches Rd, Head Of The Harbor, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Welcome to this updated classic country colonial where modern amenities blend seamlessly with timeless charm. This thoughtfully renovated home features gas heat, central air, updated Andersen windows, updated baths, gleaming wood floors, and custom millwork. The kitchen shines with stainless steel appliances, gas cooking, and white cabinetry, while spacious formal rooms, a wood burning fireplace, and a sunroom add warmth and elegance. The recently renovated large primary bedroom suite includes a beautiful ensuite bath. Set on 3.5 lush acres, the property offers a detached 1 car garage with additional potential room for guest quarters, a 2-stall stable, a sparkling inground pool with an upda

$1,349,000

5 beds2.5 baths2,541 sq ft

537 Moriches Rd, Head Of The Harbor, NY 11780

3.5 acre lot • Garage • Pool

Listing by Daniel Gale Sothebys Intl Rlty

15 Emmet Dr, Head Of The Harbor, NY 11790
15 Emmet Dr, Head Of The Harbor, NY 11790
15 Emmet Dr, Head Of The Harbor, NY 11790
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Experience the most exclusive property on the North Shore at The Mallows, a historic waterfront masterpiece in the prestigious Head of the Harbor Village. Designed by renowned architect Charles Platt for the esteemed Astor family, this iconic estate spans over four acres of impeccably manicured grounds with more than 300 feet of private beachfront. With breathtaking west-facing sunset views over Stony Brook Harbor, extending to the Long Island Sound and Connecticut, this rare offering epitomizes luxury and exclusivity. Seamlessly blending historic charm with modern elegance, this estate offers resort-style outdoor living with a heated saltwater pool, hot tub, private tennis court, and a pic

$5,499,000

11 beds6 baths9,411 sq ft

15 Emmet Dr, Head Of The Harbor, NY 11790

4.1 acre lot • Garage • Pool

Listing by Frontline Realty Group LLC

NEW CONSTRUCTION

550 Moriches Rd, Head Of The Harbor, NY 11780
550 Moriches Rd, Head Of The Harbor, NY 11780
550 Moriches Rd, Head Of The Harbor, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Rare opportunity to own Custom 6000 sq ft New Construction in a most private and sought after original Estate Area of the famed White Family. Stately circular driveway welcomes you to this beautifully designed 5 en Suite Bedroom Home. Flanking the open 2 story entry foyer you will enjoy the privacy of the Library with dramatic French double door entry and Formal living room, The coffered ceiling which extends through to the soaring great room highlighting the natural gas fireplace and open to custom designer kitchen with Merillat Masterpiece custom cabinetry, quartz countertops and center island, Sub-Zero 48'' Stainless refrigerator, Wolf 48'' dual fuel range, Wolf microwave drawer, Bosch s

$3,590,000

5 beds5.5 baths6,000 sq ft

550 Moriches Rd, Head Of The Harbor, NY 11780

2.33 acre lot • Car-dependent

Listing by Daniel Gale Sothebys Intl Rlty

Property at 20 Carman Ln, Head Of The Harbor, NY 11780, 5 beds, 5.5 baths

$2,799,000

5 beds5.5 baths8,000 sq ft

20 Carman Ln, Head Of The Harbor, NY 11780

Listing by Compass Greater NY LLC

Property at Lot 1 Timothy Ln, Head Of The Harbor, NY 11780

$750,000

— beds— baths— sq ft

Lot 1 Timothy Ln, Head Of The Harbor, NY 11780

Listing by Douglas Elliman Real Estate

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NEW 1 HR AGO

613 Moriches Rd, Nissequogue, NY 11780
613 Moriches Rd, Nissequogue, NY 11780
613 Moriches Rd, Nissequogue, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Discover The Warmth And Beauty Of This Five Bedroom, Four Bathroom Georgian Colonial Located In The Highly Desirable Incorporated Village Of Nissequogue. Nestled On Three Acres Of Breathtaking And Picturesque Property, This Home Offers Unparalleled Privacy And Natural Beauty. Highlights Include A Sun-Filled Foyer Entry, Spacious Eat-In Kitchen With Granite Countertops, A Warm And Cozy Inviting Den, Elegant Living Room With Wood Burning Fireplace, Formal Dining Room And Entertaining Bonus Room With Fireplace. The Primary Suite Is Comfortably Luxurious With A Stunning Newly Updated Primary Bathroom With Marble, Stand-Alone Tub, High Ceilings And Vanity As Well As A Walk-In Closet. Additional

$1,600,000

5 beds4 baths3,900 sq ft

613 Moriches Rd, Nissequogue, NY 11780

3 acre lot • 2 garage spots • Car-dependent

Listing by Compass Greater NY LLC

NEW 3 HRS AGO

1204 Gotham Dr #1204, Saint James, NY 11780
1204 Gotham Dr #1204, Saint James, NY 11780
1204 Gotham Dr #1204, Saint James, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Lovely ground floor home in extremely desirable Fairfield adult community. This lovely condo is filled with light with a large living room with patio doors leading to private brick patio with an awning. The kitchen has lots of cabinets and a spacious dining area. The primary bedroom is large with lots of closets and an ensuite bathroom. The dining room has been converted into a temporary bedoom with a half bathroom and a closet. . The wall can easily be removed by buyer if desired. Located on a lovely block with plenty parking. Community offers lots of amenities including swimming pools, gym , tennis walking trails and an active club house. Updates include electrical box, Central air,

$424,990

1 bed1.5 baths750 sq ft

1204 Gotham Dr #1204, Saint James, NY 11780

$260 HOA • Community pool • Car-dependent

Listing by Signature Premier Properties

184 Jefferson Ave, Saint James, NY 11780
184 Jefferson Ave, Saint James, NY 11780
184 Jefferson Ave, Saint James, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
100+ year old colonial with great charm and potential. This home sits on a flat half acre with an oversized 2 car detached garage with a workshop in the back. Windows and roof have been updated within 10 years. House has been converted to gas. Solar panels will be paid in full at closing. This home is the perfect canvas to make into your dream home. Off the kitchen, which is equipped with radiant heat floors, is space that could be used as a family room or formal dining room. This space has a cozy wood burning stove. Come see this 3 bedroom 1.5 bath home that exudes character and a welcoming feel in the Smithtown School District.

$699,000

3 beds1.5 baths1,150 sq ft

184 Jefferson Ave, Saint James, NY 11780

0.5 acre lot • 2 garage spots • Somewhat walkable

Listing by Signature Premier Properties

501 Lennox Dr #501, Saint James, NY 11780
501 Lennox Dr #501, Saint James, NY 11780
501 Lennox Dr #501, Saint James, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Welcome to a rare find in Kensington Gardens! Discover the largest model in the community, the Somerset, offering spacious and comfortable living in the highly sought-after Kensington Gardens. This 2-bedroom, 2-bathroom co-op features an updated primary bath, a modern kitchen, and the convenience of in-unit laundry. With a 1-car garage and a partial basement, there’s plenty of storage and space to meet your needs. Kensington Gardens offers a vibrant community lifestyle with outstanding amenities, including a clubhouse with a kitchen, card & game room, exercise room, and a pool—perfect for socializing and staying active. Taxes are included in the maintenance fees.

$533,447

2 beds2 baths1,306 sq ft

501 Lennox Dr #501, Saint James, NY 11780

$1,065 HOA • Garage • Community pool

Listing by Signature Premier Properties

420 Moriches Rd, Saint James, NY 11780
420 Moriches Rd, Saint James, NY 11780
420 Moriches Rd, Saint James, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Why rent when you can own? Don't miss out on this opportunity to own this 4 bedroom cape in desirable Saint James in Smithtown school district on 1/3 acre! This home features hardwood floors, natural gas heat and cooking with central air conditioning. There is plenty of storage and room to expand into the partially finished basement and 2 car detached garage. Bring your vision and make this house your home!

$524,990

4 beds2 baths1,551 sq ft

420 Moriches Rd, Saint James, NY 11780

0.3 acre lot • 2 garage spots • Very walkable

Listing by Compass Greater NY LLC

3D WALKTHROUGH

293 1st Ave, Saint James, NY 11780
293 1st Ave, Saint James, NY 11780
293 1st Ave, Saint James, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
This 3-bedroom Village Charmer offers many updates and a unique lifestyle opportunity! This sun filled ranch is located in the heart of St. James; where you will enjoy great shops, dining and recreational activities. A short walk to nearby LIRR or elementary school. The current owner has accomplished many updates leaving you more time to relax and enjoy your new home! From the expansive paved driveway with lovely front gardens and low maintenance vinyl siding and updated windows to the freshly painted interior with gleaming refinished oak flooring and all new baseboards. The great room with vaulted ceilings and recessed lighting is a great first impression, the kitchen is light and bright

$549,000

3 beds1 bath900 sq ft

293 1st Ave, Saint James, NY 11780

5,227 sq ft lot • Very walkable

Listing by Howard Hanna Coach

Property at Drive Pondview, Saint James, NY 11780, 4 beds, 3.5 baths

$1,345,000

4 beds3.5 baths3,500 sq ft

Drive Pondview, Saint James, NY 11780

Listing by Daniel Gale Sothebys Intl Rlty

Property at 1234 N Country Rd, Stony Brook, NY 11790, 3 beds, 2.5 baths

$1,500,000

3 beds2.5 baths2,063 sq ft

1234 N Country Rd, Stony Brook, NY 11790

Listing by Daniel Gale Sothebys Intl Rlty

Property at 246 Woodlawn Ave, Saint James, NY 11780, 3 beds, 2 baths

$599,990

3 beds2 baths— sq ft

246 Woodlawn Ave, Saint James, NY 11780

Listing by RE/MAX Signature Real Estate

Property at 9 Swan Pl, Nissequogue, NY 11780, 7 beds, 6.5 baths

$2,899,996

7 beds6.5 baths8,380 sq ft

9 Swan Pl, Nissequogue, NY 11780

Listing by BERKSHIRE HATHAWAY

Property at 7 Short Path, Nissequogue, NY 11780, 4 beds, 3.5 baths

$1,099,000

4 beds3.5 baths2,500 sq ft

7 Short Path, Nissequogue, NY 11780

Listing by Daniel Gale Sothebys Intl Rlty

Property at 122 Fifth St, Saint James, NY 11780, 3 beds, 2.5 baths

$849,000

3 beds2.5 baths2,000 sq ft

122 Fifth St, Saint James, NY 11780

Listing by DeBarbieri Assoc Inc

Property at 4 Celestial Ct, Saint James, NY 11780, 6 beds, 4.5 baths

$2,200,000

6 beds4.5 baths— sq ft

4 Celestial Ct, Saint James, NY 11780

Listing by Frontline Realty Group LLC

Property at 35 Monterrey Dr, Saint James, NY 11780, 5 beds, 3.5 baths

$1,389,000

5 beds3.5 baths4,960 sq ft

35 Monterrey Dr, Saint James, NY 11780

Listing by Signature Premier Properties

Property at 292 Northern Blvd, Saint James, NY 11780, 4 beds, 3 baths

$840,000

4 beds3 baths2,645 sq ft

292 Northern Blvd, Saint James, NY 11780

Listing by Realty Connect USA L I Inc

Property at 50 7th St, Saint James, NY 11780, 4 beds, 1 bath

$552,900

4 beds1 bath1,600 sq ft

50 7th St, Saint James, NY 11780

Listing by New Door Properties LLC

Property at 10 Aspen Cir, Saint James, NY 11780, 4 beds, 2.5 baths

$899,000

4 beds2.5 baths— sq ft

10 Aspen Cir, Saint James, NY 11780

Listing by SRG Residential LLC

$679,000

3 beds3 baths— sq ft

21 Grove Ave, Saint James, NY 11780

Listing by Signature Premier Properties

Property at 10 Old Mill Rd, Saint James, NY 11780

$448,000

— beds— baths— sq ft

10 Old Mill Rd, Saint James, NY 11780

Listing by VYLLA Home

Property at 553 North Country Rd, Saint James, NY 11780

$429,000

— beds— baths— sq ft

553 North Country Rd, Saint James, NY 11780

Listing by DeBarbieri Assoc Inc

Based on information submitted to the MLS GRID as of Mon Mar 03 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Average home prices near Head of the Harbor, NY

Cities

Neighborhoods
Zip Codes

Long Island homes for sale
$849,944

Head of the Harbor, NY real estate trends

$975K

Sale price

+25.4%
since last year

$270

Sale $/sq ft

-13.5%
since last year

Under list price

1.7%

Days on market

Down payment

—

Total homes sold

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