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

8 homes

Sort:

Recommended

3D WALKTHROUGH

595 Moriches Rd, Nissequogue, NY 11780
595 Moriches Rd, Nissequogue, NY 11780
595 Moriches Rd, Nissequogue, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
When you enter the driveway on Cordwood Path, you will know you have found your home. Tucked away among mature trees, this stately yet welcoming home offers an exceptional blend of elegance, comfort, and privacy. From the moment you arrive via the interlocking brick walkway, you’re greeted by low-maintenance, manicured landscaping that reflects true pride of ownership—and a home that’s been both thoughtfully designed and beautifully maintained. Inside, upscale ceiling details and solid wood oak flooring with sun-kissed wood tones create an immediate sense of warmth and refinement. The tile entryway is as functional as it is impressive, setting the tone for a home that bala

$1,999,999

3 beds3 baths3,600 sq ft

595 Moriches Rd, Nissequogue, NY 11780

2.6 acre lot • 6 garage spots • Car-dependent

Listing by Signature Premier Properties

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
A Rare Country Retreat on 3.5 Level Acres in Head of the Harbor Welcome to a truly special property that captures the charm and serenity of a classic country estate—gracious, private, and full of old-world appeal. Set on an incredibly rare and completely level 3.5-acre parcel, this beautiful setting offers a sense of space and tranquility that’s hard to find. Located just minutes from Long Island Sound beaches, local restaurants, charming village shops, and Stony Brook University, it’s a peaceful retreat that keeps you close to everything. This updated classic Colonial blends timeless style with modern comforts. Inside, you’ll find rich wood floors, custom millwork,

$1,249,000

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

118 Harbor Rd, Saint James, NY 11780
118 Harbor Rd, Saint James, NY 11780
118 Harbor Rd, Saint James, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Welcome to 118 Harbor Road, Head of The Harbor, NY – A Charming Retreat in the Heart of Nature Nestled on 2 acres of serene, rustic property that backs onto acres of pristine wooded land, This lovely home offers the perfect blend of privacy, tranquility, and charm. Country Kitchen: The generous-sized kitchen features a breakfast island with a granite countertop, a built-in wall grill, and a large picturesque window that frames a lovely view of the yard. Living Room & Den: The spacious living room includes a two-sided wood-burning fireplace, which is shared with the kitchen. A cozy den, directly off the dining room, features its own wood-burning fireplace and a large built-in win

$1,199,000

4 beds3 baths2,583 sq ft

118 Harbor Rd, Saint James, NY 11780

2 acre lot • 2 garage spots • Pool

Listing by Howard Hanna Coach

3D WALKTHROUGH

33 Bacon Rd, Saint James, NY 11780
33 Bacon Rd, Saint James, NY 11780
33 Bacon Rd, Saint James, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Expansive 6 BR "Better than New"Georgian Colonial . Every Detail and Amenity possible ! Experience luxury living at its finest in this breathtaking and stately and unsurpassed in quality colonial, where timeless elegance and modern sophistication blend seamlessly. With its striking stone front exterior and inviting paver walkways, this extraordinary property is for the discerning buyer seeking a truly one of a kind home. Nestled on 3.50 lush, level, professionally manicured acres in the private Village of Head of the Harbor, this extraordinary estate offers unparalleled quality and craftsmanship in every detail. Step into the grand two-story entry foyer with exquisite marble floor

$2,599,000

6 beds5.5 baths4,850 sq ft

33 Bacon Rd, Saint James, NY 11780

3.5 acre lot • 3 garage spots • Pool

Listing by Daniel Gale Sothebys Intl Rlty

23 Bacon Rd, Head Of The Harbor, NY 11780
23 Bacon Rd, Head Of The Harbor, NY 11780
23 Bacon Rd, Head Of The Harbor, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Welcome to 23 Bacon Road - The Best Value in the coveted Head of the Harbor ! This Elegant & expansive Ranch-Style home is nestled on 2.38 beautifully landscaped acres in the heart of Head of the Harbor. Built in 1960 & designed by renowned builder Yablonski - This home offers over 5,300 square feet of exquisite living space, This one-of-a-kind gem features a first floor master bedroom, generous room sizes, a sun-drenched sun room and fully finished basement, perfect for entertaining or extended family. Each of the five oversized bedrooms offers comfort and privacy, with ample closet space throughout. The home seamlessly blends classic charm with with modern flavor and is surro

$1,399,999

5 beds5 baths5,393 sq ft

23 Bacon Rd, Head Of The Harbor, NY 11780

2.38 acre lot • 2 garage spots • Pool

Listing by Signature Premier Properties

Property at 91 Harbor Rd, Head Of The Harbor, NY 11780, 3 beds, 3.5 baths

$1,499,000

3 beds3.5 baths3,210 sq ft

91 Harbor Rd, Head Of The Harbor, NY 11780

Listing by Daniel Gale Sothebys Intl Rlty

Property at 15 Emmet Dr, Head Of The Harbor, NY 11790, 11 beds, 6 baths

$4,000,000

11 beds6 baths9,411 sq ft

15 Emmet Dr, Head Of The Harbor, NY 11790

Listing by Frontline Realty Group LLC

Property at 17 Barn Ln, Head Of The Harbor, NY 11780, 5 beds, 4.5 baths

$2,900,000

5 beds4.5 baths5,340 sq ft

17 Barn Ln, Head Of The Harbor, NY 11780

Listing by Daniel Gale Sothebys Intl Rlty

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

OPEN THU, 4:30PM TO 6:30PM

5 Aspen Cir, Saint James, NY 11780
5 Aspen Cir, Saint James, NY 11780
5 Aspen Cir, Saint James, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Welcome to this beautifully updated Post Modern Colonial nestled on a cul-de-sac in the heart of St. James. This home features an impressive 2-story entry foyer, a stunning center island eat-in kitchen renovated in 2019 with quartz countertops and stainless steel appliances, with an open concept family room including a natural gas fireplace and stacked stone facade. The formal living and dining room provide elegant entertaining spaces, while hardwood floors flow throughout the first floor & bedrooms. Upstairs, you will notice the open and airy landing providing access to the bedrooms. The spacious primary bedroom suite offers a luxurious ensuite bath renovated in 2019, walk-in closet,

$1,025,000

4 beds2.5 baths2,725 sq ft

5 Aspen Cir, Saint James, NY 11780

0.5 acre lot • 2 garage spots • Somewhat walkable

Listing by Howard Hanna Coach

1251 A North Country Rd, Stony Brook, NY 11790
1251 A North Country Rd, Stony Brook, NY 11790
1251 A North Country Rd, Stony Brook, NY 11790
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Tucked away in a small pocket neighborhood in Stony Brook Village, this spacious 4 bedroom 3.5 bath Colonial is conveniently located close to the charming village and Stony Brook University. Built in 1996 the home offers a unique, open 3 story floor plan, high ceilings, custom woodwork, hardwood floors and private location with salt water pool punctuating the beautifully landscaped backyard. Recently renovated custom Chef’s Kitchen includes upscale appliances, stone counters and opens to a bright Great Room with wood burning fireplace. Substantial primary suite with gas fireplace has two walk-in closets and sizable Spa Bath. Three gracious bedrooms and additional full bath complete 2n

$1,095,000

4 beds3.5 baths3,000 sq ft

1251 A North Country Rd, Stony Brook, NY 11790

0.69 acre lot • 2 garage spots • Pool

Listing by Daniel Gale Sothebys Intl Rlty

914 Fenway Rd, Saint James, NY 11780
914 Fenway Rd, Saint James, NY 11780
914 Fenway Rd, Saint James, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Beautiful 2Bedroom 2 Bath Condo (55) with wood floors, attached garage, and balcony views! Formal dining room, EIK, Lots of. closets! Enjoy tennis, Pickleball, Swimming Pool & a friendly clubhouse community.

$499,000

2 beds2 baths1,200 sq ft

914 Fenway Rd, Saint James, NY 11780

$366 HOA • Garage • Community pool

Listing by Douglas Elliman Real Estate

145 Fifty Acre Rd S, Smithtown, NY 11787
145 Fifty Acre Rd S, Smithtown, NY 11787
145 Fifty Acre Rd S, Smithtown, NY 11787
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Lovely Five bedroom, Three Full Bath Splanch home on a level . 23 acre. Architectural Roof +/- 10 Years, Large Eat In Kitchen, covered Front Porch, Fenced Rear yard, One Car Attached Garage, Rear Paver Patio, Blacktop Belgian Block lined Driveway. The Home has some Oak Floors, Partial Basement, 100 Amp electric, Public Water, Thermopane Windows, Vinyl / asbestos & brick siding. Oil Hot water Heat 275 Gallon Oil Tank In basement.

$699,000

5 beds3 baths2,872 sq ft

145 Fifty Acre Rd S, Smithtown, NY 11787

0.23 acre lot • 2 garage spots • Car-dependent

Listing by DeBarbieri Assoc Inc

4 Forsythe Meadow Ln, Stony Brook, NY 11790
4 Forsythe Meadow Ln, Stony Brook, NY 11790
4 Forsythe Meadow Ln, Stony Brook, NY 11790
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
Welcome to Forsythe Meadow in Stony Brook. This exquisite colonial is the perfect home for scenic beauty, tranquility, and community. The backdrop features open views of Forsythe Meadow County Park making entertaining a most desirable experience and privacy. It features an owned solar system, radiant heat throughout with hot air back up, sunken dining/living room, hot tub with beautiful yard views, outdoor shower, in ground swimming pool, central vac system, Three Village Schools, and a short hop to Stony Brook Village shopping, and the LIRR. This home is designed to sell quickly and offer you years of beautiful memories.

$1,200,000

4 beds2.5 baths3,559 sq ft

4 Forsythe Meadow Ln, Stony Brook, NY 11790

0.52 acre lot • 2 garage spots • Pool

Listing by Howard Hanna Coach

11 Grove Ave, Saint James, NY 11780
11 Grove Ave, Saint James, NY 11780
11 Grove Ave, Saint James, NY 11780
ABOUT THIS HOME
Head of the Harbor, NY Homes for Sale
This unique property offers not one, but two separate dwellings on a beautifully half acre landscaped lot. The main residence is a well-maintained side-by-side split featuring 3 bedrooms, 2 full baths, hardwood floors, a cozy fireplace, and generous living space ideal for everyday comfort and entertaining. The second dwelling is a delightful 1–2 bedroom cottage complete with basement and attic and its own private yard and driveway—perfect for extended family, guests, or rental income opportunities. Enjoy outdoor living on the spacious back deck surrounded by mature trees, or unwind in the peaceful front yard on a dead end street. Whether you're looking for a multigenerational se

$849,000

4 beds3 baths2,800 sq ft

11 Grove Ave, Saint James, NY 11780

0.5 acre lot • Somewhat walkable

Listing by Douglas Elliman Real Estate

Property at 263 North Country Rd, Smithtown, NY 11787, 3 beds, 3 baths

$649,000

3 beds3 baths1,561 sq ft

263 North Country Rd, Smithtown, NY 11787

Listing by Daniel Gale Sothebys Intl Rlty

Property at 205 Flair Ct E, Saint James, NY 11780, 3 beds, 2.5 baths

$619,990

3 beds2.5 baths1,600 sq ft

205 Flair Ct E, Saint James, NY 11780

Listing by Signature Premier Properties

Property at 122 Fifth St, Saint James, NY 11780, 4 beds, 2.5 baths

$749,000

4 beds2.5 baths2,000 sq ft

122 Fifth St, Saint James, NY 11780

Listing by DeBarbieri Assoc Inc

Property at 1152 N Country Rd, Stony Brook, NY 11790, 4 beds, 1.5 baths

$600,000

4 beds1.5 baths1,500 sq ft

1152 N Country Rd, Stony Brook, NY 11790

Listing by Keller Williams Points North

Property at 122 Cambon Ave, Saint James, NY 11780, 6 beds, 5 baths

$1,275,000

6 beds5 baths3,600 sq ft

122 Cambon Ave, Saint James, NY 11780

Listing by DeBarbieri Assoc Inc

Property at 120 Fifth St, Saint James, NY 11780, 4 beds, 3 baths

$1,349,000

4 beds3 baths3,250 sq ft

120 Fifth St, Saint James, NY 11780

Listing by DeBarbieri Assoc Inc

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

$1,499,000

5 beds3.5 baths4,960 sq ft

35 Monterrey Dr, Saint James, NY 11780

Listing by Compass Greater NY LLC

Property at 6 Cedarfield Ter, Setauket, NY 11780, 4 beds, 3.5 baths

$872,000

4 beds3.5 baths3,200 sq ft

6 Cedarfield Ter, Setauket, NY 11780

Listing by HomeSmart Premier Living Rlty

Property at 120 Cambon Ave, Saint James, NY 11780, 3 beds, 3.5 baths

$2,488,888

3 beds3.5 baths3,500 sq ft

120 Cambon Ave, Saint James, NY 11780

Listing by Compass Greater NY LLC

Property at 9 Aron St, Smithtown, NY 11787, 4 beds, 2.5 baths

$979,999

4 beds2.5 baths2,900 sq ft

9 Aron St, Smithtown, NY 11787

Listing by Blue Island Homes NY LLC

Property at 232 7th St, Saint James, NY 11780, 6 beds, 3 baths

$720,000

6 beds3 baths2,344 sq ft

232 7th St, Saint James, NY 11780

Listing by RE/MAX Best

Property at 4 Celestial Ct, Saint James, NY 11780, 6 beds, 5.5 baths

$2,199,000

6 beds5.5 baths4,820 sq ft

4 Celestial Ct, Saint James, NY 11780

Listing by Daniel Gale Sothebys Intl Rlty

Property at 302 Gotham Way, Saint James, NY 11780, 3 beds, 2.5 baths

$619,000

3 beds2.5 baths1,548 sq ft

302 Gotham Way, Saint James, NY 11780

Listing by Signature Premier Properties

Property at 342 Northern Blvd, Saint James, NY 11780, 3 beds, 2 baths

$749,000

3 beds2 baths1,748 sq ft

342 Northern Blvd, Saint James, NY 11780

Listing by Daniel Gale Sothebys Intl Rlty

Based on information submitted to the MLS GRID as of Mon Jul 14 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
$868,500

Head of the Harbor, NY real estate trends

$1.25M

Sale price

+8.5%
since last year

$354

Sale $/sq ft

Under list price

1.7%

Days on market

Down payment

—

Total homes sold

See more Head of the Harbor, NY market insights

More to explore in Head of the Harbor, NY

Featured
Bedroom

How to buy a house in Head of the Harbor, NY

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in New York

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Countries

United States

Canada

Updated January 2023: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, TITLE FORWARD, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York. For additional information on Rocket Mortgage or to receive lending services in the State of New York, please visit RocketMortgage.com.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.