HEAD OF THE HARBOR, NY HOMES FOR SALE


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Head of the Harbor

Head of the Harbor is a picturesque incorporated village situated north of St. James in the Township of Smithtown. It is bordered on the north by Stony Brook Harbor. Head of the Harbor is made up of mostly residential homes and agricultural areas. There is a public beach access at Cordwood Park. This was an area cordwood was shipped from when cordwood farming was prevalent in this area of The North Shore of Long Island. One of its noteworthy residents was the famous architect Stanford White.

Head of the Harbor

Total Listings: 31
Average Price: $1,333,839
Highest Price: $4,250,000
Lowest Price: $335,000

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Head of the Harbor Homes For Sale

31 Properties Found. Page 1 of 1
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"perfection Personified" Diamond Completely Upd...

NEW Photo of Listing #2947705

$839,000

7 Watercrest Ct, Head Of Harbor

  • 5 Beds
  • 3 Baths
  • 2 Acres
  • 2,800 sqft

School District: Smithtown

"perfection Personified" Diamond Completely Updt Sprawling 5br 3bath Ranch W/ Gorgeous "designer Decor" & Spacious Open Floor Plan, Set On 2 Wooded Acres Offering Complete Privacy! Meticulously Maintained Home W/ Gleaming Wood Flrs, Beautiful Custom Millwor...

Property Lovers Delight! Large Colonial On Spra...

Photo of Listing #2946154

$829,000

14 Bacon Rd, Head Of Harbor

  • 4 Beds
  • 4 Baths
  • 2 Acres

School District: Smithtown

Property Lovers Delight! Large Colonial On Sprawling Flat And Fully Fenced Two Acre Property Within Beautiful Head Of The Harbor Village! New Ig Salt Water Heated Pool, Central Air, Hardwood Floors (1st Floor), Over Sized Den W/fireplace, Large Eat-in-kitc...

Tranquility At Its Finest! This Beautiful Open ...

Photo of Listing #2946163

$1,250,000

3 Cordwood Path, Head Of Harbor

  • 3 Beds
  • 2 Baths
  • 2.61 Acres

School District: Smithtown

Tranquility At Its Finest! This Beautiful Open Floor Plan Home Offers, Not Only Views Of Your Very Own Private Pond, But Also A State Of The Art European Kitchen, High Quality Appointments Throughout. A Private Master Bedroom Ensuite With Custom Dressing Ro...

Pristine Colonial In A Great Location & Private...

Photo of Listing #2943179

$1,099,000

4 Wetherill Lane, Head Of Harbor

  • 4 Beds
  • 4 Baths
  • 2 Acres
  • 3,700 sqft

School District: Smithtown

Pristine Colonial In A Great Location & Private Road. Updated Gourmet Kitchen, Formal Dr, Living Room, Family Room W/wood Burning Fp, Office, Master Br Suite, 3 Br, 3 1/2 Bths. Full Fin. Basement With All The Amenitites And Great Living Space. Access To The...

Build Your Dream Home--majestic Post Modern Col...

Photo of Listing #2941172

$1,898,000

8 Timothy Ln, Head Of Harbor

  • 4 Beds
  • 4 Baths
  • 3.25 Acres
  • 3,400 sqft

School District: Smithtown

Build Your Dream Home--majestic Post Modern Colonial To Be Built At End Of Quiet Cul-de-sac With Cedar Shake Exterior, Guest Suite On Main Floor, High Ceilings, Gas Heat & 3-car Garage . Customize This Luxurious Home To Your Taste & Color Palette. Located...

Magnificent Custom Built 5/6 Br Colonial On Cul...

Photo of Listing #2940505

$1,690,000

21 Woodlot Rd, Head Of Harbor

  • 5 Beds
  • 4 Baths
  • 2.01 Acres

School District: Smithtown

Magnificent Custom Built 5/6 Br Colonial On Culdesac W/seasonal Harbor Waterviews. 1st & 2nd Flr Mstr Suites. Custom Gourmet Kit W/brkfst Counter, Huge Center Island, Rad. Heat, Walk In Pantry. Banquet Dr. Chefs/entertainers Delight. Flr W/coffered Ceils, O...

Beautiful 3.69 Acre Bldg Lot. 3 Village Schools...

Photo of Listing #2940340

$335,000

1253 N Country Rd, Head Of Harbor

  • 3.69 Acres

School District: Three Village

Beautiful 3.69 Acre Bldg Lot. 3 Village Schools. Sold W/plans & Approvals For A 4,600 Sqft Home W/3 Car Garage. Driveway Access Is Cleared. Walk To Stony Brook Village & Docks. Near Avalon Preserve. Lots Of Level Land. Very Secluded Estate Setting. Plans In...

Sprawling Cedar And Stone Colonial On Private 2...

Photo of Listing #2939062

$1,200,000

5 Meadow Gate East, Head Of Harbor

  • 5 Beds
  • 6 Baths
  • 2.14 Acres
  • 5,400 sqft

School District: Smithtown

Sprawling Cedar And Stone Colonial On Private 2+acres. This Residence Offers An Open Floor Plan With All The Amenities. Spacious Rooms, Gourmet Kitchen, (subzero, Viking, Custom Cabinets, Granite) 5/6 Bedrooms, 5.5 Baths, Office/guest Suite Or First Floor M...

Large, Diamond Condition Colonial Set On Cul-de...

Photo of Listing #2933835

$1,199,000

12 Saneck Dr, Head Of Harbor

  • 5 Beds
  • 4 Baths
  • 2.59 Acres
  • 5,200 sqft

School District: Three Village

Large, Diamond Condition Colonial Set On Cul-de-sac Adjacent To Nature Conservancy. All Principal Rooms Are Oversized And Feature 10' Ceilings. Exquisite Kitchen & Bathrooms, Bridal Staircase, 3 F/p's, Master Suite W/sitting Rm, Custom Closets, Cv, Igs, 30...

Spacious Center Hall Colonial. Fabulous Open Fl...

REDUCED 4% Photo of Listing #2933022

$749,000

22 Three Sisters Rd, Head Of Harbor

  • 4 Beds
  • 3 Baths
  • 2.08 Acres

School District: Smithtown

Spacious Center Hall Colonial. Fabulous Open Floor Plan W/lots Of Updates Including Cac, Roof, Granite Kitchen With Brand New Dishwasher And Brand New State Of The Art Heating System.warm&welcoming With 2 Fp's,gleaming Wd/flrs Yet Open With Vaulted Ceiling...

"price Reduction" Spacious Center Hall Colonial...

REDUCED 6% Photo of Listing #2931922

$749,000

35 Farm Rd, Head Of Harbor

  • 4 Beds
  • 4 Baths
  • 2.27 Acres
  • 3,116 sqft

School District: Smithtown

"price Reduction" Spacious Center Hall Colonial On Over 2 Private Wooded Acres In The Heart Of Head Of The Harbor. Home Boasts 4/5 Bedrooms, 3 1/2 Baths, And An Over-sized 2 1/2 Car Garage. Home Needs Updating But Has Unlimited Potential For Future Owner/in...

Move Right Into This Magnificent 6 Br, 4.5 Bath...

REDUCED 3% Photo of Listing #2927799

$1,190,000

12 Harbor Rd, Head Of Harbor

  • 6 Beds
  • 5 Baths
  • 2.68 Acres

School District: Smithtown

Move Right Into This Magnificent 6 Br, 4.5 Bath Colonial On 2.68 Serene Acres In Lovely Head Of The Harbor. This Exquisite Home Boasts Spacious Principle Rms; Updated Kitchen W/wolf Appliances, Quartz & Granite Counters; Den W/fireplace; Updated Baths; Mast...

Sprawling Ranch Situated On Private 2 Acre Lot....

REDUCED 7% Photo of Listing #2927572

$999,000 Under Contract

104 Harbor Rd, Head Of Harbor

  • 4 Beds
  • 3 Baths
  • 2 Acres

School District: Smithtown

Sprawling Ranch Situated On Private 2 Acre Lot. This Home Features Great Room With Vaulted Ceilings And Fireplace, Large Master Suite With Updated Bath And Steam Shower, Guest Suite With Ose, Newer Kitchen With Thermador Oven, 6 Burner Cooktop, Custom Hicko...

To Be Built! Timeless & Luxurious, This Home Wi...

Photo of Listing #2925559

$2,995,000

5 Woodlot Road, Head Of Harbor

  • 4 Beds
  • 5 Baths
  • 2 Acres
  • 6,000 sqft

School District: Smithtown

To Be Built! Timeless & Luxurious, This Home Will Sit On 2 Acres Overlooking Magnificent Stony Brook Harbor. Will Offer 6000 Sf Of Spectacular Living Space Including 4 Master Br W/ En-suites,gourmet Kitchen W/breakfast Rm,flr,fdr, And A Light-filled Lower ...

Stunning Custom Built Hamptons Style Post Moder...

Photo of Listing #2925301

$1,550,000 Under Contract

37 Farm Rd, Head Of Harbor

  • 4 Beds
  • 4 Baths
  • 2.01 Acres
  • 5,700 sqft

School District: Smithtown

Stunning Custom Built Hamptons Style Post Modern, Grand Entrance Foyer, Custom Gourmet Eik W Ss Viking Appl, Coffee Station. Large Family Room W 10' Ceils, Fp, Spectacular Master Suite W/bluestone Balcony. 4 Gas Fp. Dual Staircases, 3+ Car Att. Garage, Fa...

Stunning Gated Brick Masterpiece Set On 2 Acres...

REDUCED 8% Photo of Listing #2924193

$1,650,000

1 Wicks Lane, Head Of Harbor

  • 5 Beds
  • 4 Baths
  • 2 Acres
  • 4,500 sqft

School District: Smithtown

Stunning Gated Brick Masterpiece Set On 2 Acres On A Pristine Cul-de-sac. This Gorgeous One Level Residence Integrates Classic Amenities W/custom Millwork. Grand & Spacious And Perfect For Family Gatherings/elegant Entertaining. Gourmet Kit, Bar Room, Den &...

Custom Built Ranch On 3+ Acres, Set Back From ...

Photo of Listing #2946987

$615,000

579 Moriches Rd, Head Of Harbor

  • 4 Beds
  • 3 Baths
  • 3.04 Acres
  • 2,000 sqft

School District: Smithtown

Custom Built Ranch On 3+ Acres, Set Back From Road On Private Serene Setting In Village Of Head Of Harbor. Unusual Floor Plan Allows Creativity. Featuring Master Bedroom With Sunroom (vaulted Ceiling), Private Deck. Sun-lit Liv. Rm.-fireplace With Built...

Sprawling Country Ranch With Spacious Open Flow...

REDUCED 5% Photo of Listing #2922272

$699,000

45 Fifty Acre Rd, Head Of Harbor

  • 3 Beds
  • 3 Baths
  • 2 Acres

School District: Smithtown

Sprawling Country Ranch With Spacious Open Flowing Floor Plan! Gleaming Hardwood Floors, Updated Granite Eat-in-kitchen, Great Room With Vaulted Ceilings & Slider To Huge Timber Tech Deck, Neutral Paint Colors, Woodburning Fireplace In Formal Living Room, H...

Over Four Acres Of Fields And Gardens Surround ...

Photo of Listing #2921575

$1,239,000

481 N Country Rd, Head Of Harbor

  • 9 Beds
  • 6 Baths
  • 4.23 Acres
  • 6,200 sqft

School District: Smithtown

Over Four Acres Of Fields And Gardens Surround This Grand Historic Home Conveniently Located Within Commuting Distance To Nyc Near The Lirr, Quaint Village Shops And Restaurants Of St. James, And An Easy Drive To The Wineries Of The North Fork Of Li. You W...

Timeless Elegance In A Private Setting. Beautif...

Photo of Listing #2919769

$1,269,000

46 Farm Road, Head Of Harbor

  • 4 Beds
  • 4 Baths
  • 2.05 Acres
  • 3,700 sqft

School District: Smithtown

Timeless Elegance In A Private Setting. Beautifully Renovated Farm Ranch With Quality Craftmanship Throughout And Master Bedroom Suite On Main Level. This Residence Has A Warm & Inviting Flow As You Walk Through The Entry To The Family Rm W/wood Fireplace, ...

Unusual Country Hampton Contemporary In Head Of...

Photo of Listing #2918220

$1,288,000

8 Emmet Dr, Head Of Harbor

  • 3 Beds
  • 3 Baths
  • 2.03 Acres
  • 4,000 sqft

School District: Three Village

Unusual Country Hampton Contemporary In Head Of Harbor Overlooking Sb Duck Pond. Ideal Location, Exciting Custom Home, Three Village Schools. Veranda And Front Porch, Cul-de-sac. Currier And Ives View. Easy To Show. Park-like Setting, Adjacent To Avalon Par...

Peaceful, Easy Lifestyle Awaits In This Sprawli...

REDUCED 5% Photo of Listing #2918264

$949,000

19 Carman Ln, Head Of Harbor

  • 4 Beds
  • 4 Baths
  • 2.36 Acres

School District: Smithtown

Peaceful, Easy Lifestyle Awaits In This Sprawling 4 Bdrm Ranch Built On Part Of The Original Stanford White Estate Known As Box Hill. Eik W/breakfast Nook, Walk-in Pantry, Ss Appl, And More. Den W/fpl And Peg Wood Flrs, Lr W/3 Sets Of French Doors, Fdr, Mas...

Totally Refinished & Exciting Home Blends Clean...

Photo of Listing #2915004

$1,299,000

9 Watercrest Ct, Head Of Harbor

  • 6 Beds
  • 8 Baths
  • 2 Acres

School District: Smithtown

Totally Refinished & Exciting Home Blends Clean & Open Lines Of Modern Architecture W/time Honored Finishes Of Molding, Wood Floors. Features Include Spacious Rooms, Updated Bths & Kit, New Floors, New Roof, Igp, Bowling Alley & Plenty Of Room For All Famil...

Beautiful Custom Colonial Overlooking The Stony...

Photo of Listing #2903890

$1,199,000 Under Contract

4 Saddle Road, Head Of Harbor

  • 5 Beds
  • 4 Baths
  • 2.34 Acres
  • 4,400 sqft

School District: Three Village

Beautiful Custom Colonial Overlooking The Stony Brook Duck Pond In A Very Peaceful & Serene Setting. 5 Bedroom, 3.5 Bath Residence Encompasses The Finest Quality & Craftmanship. 4400 Sf Of Gracious Living And Entertaining Space With A Beautiful & Open Floor...

This Expansive & Charming Ranch Home Is Placed ...

REDUCED 5% Photo of Listing #2888201

$1,049,000 Under Contract

29 Farm Rd, Head Of Harbor

  • 4 Beds
  • 5 Baths
  • 2.4 Acres

School District: Smithtown

This Expansive & Charming Ranch Home Is Placed Perfectly On A Stunning & Serene Setting. The House Has Been Updated & Features High Vaulted Ceilings, Large Windows & Multiple Sliding Glass Doors & French Doors Leading To The Wrap Around Deck Or Brick Patios...

Beautifully Updated & Meticulously Maintained H...

REDUCED 8% Photo of Listing #2882324

$1,199,000

11 E Meadow Gate, Head Of Harbor

  • 5 Beds
  • 5 Baths
  • 2.01 Acres

School District: Smithtown

Beautifully Updated & Meticulously Maintained Home W/ Traditional Interior & Designer Touches Throughout! Spacious Flowing Rms, Freshly Painted Interior, Vaulted Ceilings, Custom Granite Eik W/ New Gas Stove & New Sub Zero Fridge, Updt Andersens, New Wood ...

Priced To Sell! Exquisite Country Home Which E...

REDUCED 16% Photo of Listing #2881907

$799,000 Under Contract

1 Rhododendron Rd, Head Of Harbor

  • 4 Beds
  • 3 Baths
  • 2.7 Acres

School District: Three Village

Priced To Sell! Exquisite Country Home Which Exudes Charm & Graciousness Loc On 2.9 Acres W/ Separate Legal Cottage On Sep Parcel/ Close To Hospital & Sb University! Updated Home Includes: Gas Heat,plumbing,electric, Cac, Custom Eik W/viking Stove&marbl C,...

Grand Stately & Gorgeous Brick Colonial Loc On ...

Photo of Listing #2874693

$1,599,000 Under Contract

3 Wicks Ln, Head Of Harbor

  • 6 Beds
  • 5 Baths
  • 2 Acres

School District: Smithtown

Grand Stately & Gorgeous Brick Colonial Loc On 2 Level Usable Acres W/ Every Amenity! Spacious Upd Cherry/granite Eik, Gleaming Hw Floors, 10' Ceils, Mbr Suite On 1st Floor+2nd Mbr.2nd Fl, 4 Lg Brs On 2nd/,screened Cov Florida Rm, Gas Heat, Level 2 Acres -g...

Life Can Be One Long Vacation In This Perfect H...

REDUCED 19% Photo of Listing #2863470

$4,250,000

1 Piper Ln, Head Of Harbor

  • 5 Beds
  • 6 Baths
  • 3.91 Acres
  • 5,300 sqft

School District: Smithtown

Life Can Be One Long Vacation In This Perfect Hamptons Alternative With Over 500 Feet Of Waterfront Elevated 60 Feet Overlooking Stony Brook Harbor To Connecticut Shoreline. Peace & Tranquility Describes This Totally Renovated Home On 3.91 Parcel Offering U...

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