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Explore Similar Condos Within 2 Miles of Head of the Harbor, NY

  • /21

    $575,000

    • 2 Beds
    • 1.5 Baths

    122 Knolls Dr Unit 122, Stony Brook, NY 11790

    Fabulous ALL NEW home with spacious open plan and private patio in prime location! Chef's kitchen with quartz counters and designer white cabinetry plus stainless steel appliances. Primary suite with all new bath & Sunroom/guest room with New 1/2 bath. A picture perfect home in an upscale +55 community with pool, clubhouse and many social activities. Private patio with perennial flowers. New

    Agent Photo

    Joy Bryant

    Coldwell Banker American Homes

    (631) 544-7187

    122 Knolls Dr Unit 122, Stony Brook, NY 11790
  • /24

    $649,000 Open Sun 1PM - 3PM

    • 2 Beds
    • 2.5 Baths
    • 1,479 Sq Ft

    46 Chelsea Dr, Smithtown, NY 11787

    Live the resort lifestyle at Windcrest! The first floor features a living room, dining room, kitchen with marble countertops and access to the backyard. The upstairs has two spacious bedrooms, both with large walk in closets, private full bath. This condo resides in a private, gated community, with access to a pool, club house and tennis courts, off of route 347. Please call 631-943-9355 for

    Elias Stavrinadis Exit Family Realty

    46 Chelsea Dr, Smithtown, NY 11787
  • /32

    $619,900

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft

    5 Symphony Dr, Lake Grove, NY 11755

    Welcome to The Encore – Lake Grove’s Premier 55+ Gated Community. Step into luxury living in this diamond condition upper-level 2-bedroom, 2-bath residence, complete with convenient elevator access. Designed with soaring ceilings and bathed in natural light, this home offers an airy, open feel and has been thoughtfully updated throughout. The spacious layout includes a bright and inviting living

    John Sinkevich Daniel Gale Sothebys Intl Rlty

    5 Symphony Dr, Lake Grove, NY 11755
  • /47

    $775,000

    • 3 Beds
    • 2.5 Baths
    • 1,934 Sq Ft

    93 Paddington Cir, Smithtown, NY 11787

    Don't Miss This Beauty in the Windcrest Gated Community where residents enjoy a Country Club lifestyle with clubhouse, gym, tennis, pickeleball courts, basketball, and a heated salt water pool and lush exterior grounds. This is an End-unit Dover model which is the largest in the community! With 3-bedrooms / 2.5 baths, STONE Steps and Entry to Spacious Entry foyer, open concept Large Livingroom w/

    Lisa Sherman Realty Connect USA L I Inc

    93 Paddington Cir, Smithtown, NY 11787
  • /44

    $644,500

    • 2 Beds
    • 2.5 Baths
    • 1,413 Sq Ft

    203 Symphony Dr, Lake Grove, NY 11755

    Come see this much sought-after 2 bedroom, 2.5 bath, lower unit in a cul-de-sac in fabulous Encore Lake Grove!! This super-clean ground floor unit with eat-in kitchen leading to walk-out patio, primary bedroom with en-suite bath on main level, oak hardwood floors, attached garage with driveway, provides a clean slate for the new owner. Encore is a luxury 55+ active lifestyle community that has it

    Robert Scarito RE/MAX Integrity Leaders

    203 Symphony Dr, Lake Grove, NY 11755
  • /23

    $605,000

    • 2 Beds
    • 2 Baths
    • 1,088 Sq Ft

    128 Knolls Dr, Stony Brook, NY 11790

    The Knolls 55 active Community! This Lite & Brite Spacious 1 level Beech Model has been Professionally Renovated & Ready for you to move in! Sun Pours thru the 3 Solar Tubes to your Skillfully Designed Brand New Kitchen by ALB Interiors. White Custom Cabinetry w/ Crown Moldings/ Soft Close/ High Quality Quartz Countertops/ LG S/S ThinQ Appliances. The Range AirFrys! Refrigerator Makes Craft Ice

    Derek Greene Greene Realty Group

    128 Knolls Dr, Stony Brook, NY 11790
  • /49

    $609,998 Open Sun 12:30PM - 2PM

    • 2 Beds
    • 2 Baths
    • 1,697 Sq Ft

    23 Sonata Ct, Lake Grove, NY 11755

    Encore Lake Grove is a luxury 55+ active lifestyle condominium community. This unit is a very unique, custom upper unit "Bach" in a cul-de-sac. Enter on the lower level and take the stairs or your private elevator up to the unit. Not only does this Bach have a loft with built-ins suitable for office/crafts/additional guest space, it also has an additional room on the main level which would

    Robert Scarito RE/MAX Integrity Leaders

    23 Sonata Ct, Lake Grove, NY 11755
  • /22

    $448,000

    • 1 Bed
    • 1.5 Baths
    • 750 Sq Ft

    1504 Gotham Ct S, Saint James, NY 11780

    Charming Ground Floor Unit in Sought-After 55+ Fairfield at St. James CommunityWelcome to this lovely ground-floor unit offering soaring high ceilings and abundant natural light throughout. Located in the highly desirable Fairfield at St. James, this 55+ community provides a peaceful and vibrant lifestyle.Updated kitchen with solar tube for enhanced natural lighting, 2 beautifully updated

    Lisa Corwin Howard Hanna Coach

    1504 Gotham Ct S, Saint James, NY 11780
  • /29

    $785,000

    • 3 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    16 Scarborough Dr, Smithtown, NY 11787

    Welcome to the Beautiful Windcrest gated community. Enjoy a luxury lifestyle. Swim in a heated saltwater pool, play tennis or pickleball on lit courts, or go for a stroll on the picturesque grounds. Move right into this gorgeous home decorated and updated to perfection! PRIMARY BEDROOM WITH FULL RENOVATED BATHROOM ON THE MAIN FLOOR. Also, separate guest bath totally redone on the main floor.

    Audrey Buron Signature Premier Properties

    16 Scarborough Dr, Smithtown, NY 11787
  • /20

    $399,000

    • 2 Beds
    • 1.5 Baths
    • 916 Sq Ft

    106 Strathmore Gate Dr, Stony Brook, NY 11790

    Welcome to 106 Strathmore Gate, located within a 55+ private community. This well-maintained home features a spacious, freshly painted living room with cathedral ceilings and new carpeting. The eat-in kitchen opens to a versatile den or office with access to the courtyard. With two bedrooms, one full bath, and one-half bath, this home offers comfort and convenience. Additional highlights include

    Patricia Mayo Signature Premier Properties

    106 Strathmore Gate Dr, Stony Brook, NY 11790
  • /18

    $788,888

    • 3 Beds
    • 2.5 Baths

    22 Stone Gate Ct, Smithtown, NY 11787

    Welcome to The Regency! This beautifully maintained end-unit townhouse is located in the heart of Smithtown. Featuring 3 spacious bedrooms and 2.5 baths, this home offers an open, sunlit layout with a seamless flow from living to dining areas. The primary suite includes a walk-in closet and private bath. Enjoy your own private deck, one-car garage, and a full-house backup gas generator for

    Filomena Tortorella Signature Premier Properties

    22 Stone Gate Ct, Smithtown, NY 11787
  • /35

    $499,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    914 Fenway Rd, Saint James, NY 11780

    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. 55 and older community

    Laura Riportella Douglas Elliman Real Estate

    914 Fenway Rd, Saint James, NY 11780
  • /14

    $499,000

    • 2 Beds
    • 1.5 Baths
    • 1,134 Sq Ft

    605 Cabot Ct E Unit C605, Saint James, NY 11780

    This Residence Checks All the Boxes!! Updated and Meticulously Maintained, this One-Level Unit is Equipped with All the Essentials for Stress-Free Condominium Living. Featuring 2 Bedrooms, 1.5 Bathrooms, Attached Garage, Spacious Open Concept Living & Dining Area, Updated Eat-In Kitchen, Private Rear Patio and In-Unit Washer/Dryer, this Home is Completely Move-In Ready. Nestled within the

    Kevin Hill The Agency Northshore NY

    605 Cabot Ct E Unit C605, Saint James, NY 11780
  • /25

    $529,000 Open Sun 12PM - 2PM

    • 2 Beds
    • 2 Baths
    • 1,129 Sq Ft

    76 Knolls Dr, Stony Brook, NY 11790

    Welcome to the largest model in this highly sought after 55+ senior community! This lovely end unit 2 Bedroom, 2 bath offers privacy, natural light and an unbeatable location being in close proximity to the clubhouse. Inside you will find a spacious open floor plan with generous living and dining areas. The primary suite features a walk-in closet and an en-suite bathroom. As an end unit, enjoy

    Gina Amen American Real Estate Assoc Inc

    76 Knolls Dr, Stony Brook, NY 11790
  • /9

    $380,000

    • 2 Beds
    • 1 Bath

    94 Strathmore Gate Dr, Stony Brook, NY 11790

    This 2 bedroom, 1 bath home is nestled in a 55+ pet friendly community. This home boosts a living room with vaulted ceilings, an eat in kitchen with granite counter tops and stainless steel appliances, washer/dryer and a tiled sunroom. Close to everything- shopping, restaurants. The community offers a pool, fitness center, bocce court and shuffle board.

    Josephine Meringolo Coldwell Banker American Homes

    94 Strathmore Gate Dr, Stony Brook, NY 11790
  • /17

    $453,999

    • 2 Beds
    • 2 Baths
    • 1,292 Sq Ft

    419 Elton Ct E, Saint James, NY 11780

    This spacious unit is 1292 square feet of living space, one-floor unit offers the perfect blend of comfort and convenience. The eat-in kitchen, complete with true hardwood floors, ceiling height cabinetry and plenty of natural light flows seamlessly into the formal dining and living room, which features sliders that open to a private terrace with serene greenery views to begin the day or end the

    Danielle Curti Realty Connect USA L I Inc

    419 Elton Ct E, Saint James, NY 11780
  • /23

    $429,000

    • 1 Bed
    • 1 Bath
    • 752 Sq Ft

    1104 Drew Dr, Saint James, NY 11780

    Welcome Home To The Desirable 55+ Fairfield Community in St. James!!! This Light and Bright 1 Bedroom 1 Bathroom Unit Features New 3 Year Young Andersen Windows and 3 Year Young Central Air Conditioning, Eat In Kitchen With Granite Countertops And Oak Cabinetry, Oversized Living Room With 3 Year Young Andersen Sliding Doors That Open Up To a Brick Patio For your Outdoor Enjoyment, Oversized

    Gina Walter Century 21 Cor Ace Realty Inc

    1104 Drew Dr, Saint James, NY 11780
  • /47

    $799,999

    • 2 Beds
    • 2.5 Baths
    • 1,835 Sq Ft

    3 Concerto Dr, Lake Grove, NY 11755

    Encore Lake Grove is a luxury 55+ active lifestyle condominium, and this is a beautiful Contempo model with - one of very few built in this community! This unit has been updated and has a definite "WOW" factor as soon as you step foot inside! It has soaring ceilings with beautiful angles. The Contempo is the only model with an extra room on the main level, that can be used as a library, den,

    Robert Scarito RE/MAX Integrity Leaders

    3 Concerto Dr, Lake Grove, NY 11755
  • /2

    $399,000 Coming Soon

    • 2 Beds
    • 1.5 Baths
    • 1,023 Sq Ft

    170 Strathmore Gate Dr, Stony Brook, NY 11790

    This 2-bedroom, 1.5-bathroom home is located in a 55+ pet-friendly community. It features a new roof, a new skylight, an updated kitchen with an open-concept floor plan and high ceilings, new stainless steel appliances, a nearly new central air conditioning system, a washer and dryer, and a hot water boiler.The Strathmore Gate community offers excellent amenities, including a heated

    Xiaofang Shen Signature Premier Properties

    170 Strathmore Gate Dr, Stony Brook, NY 11790

Why Live in Head of the Harbor

Head of the Harbor in Saint James is a three-square-mile, entirely residential neighborhood characterized by its rural and pastoral feel. The area is home to approximately 1,500 residents and features winding country roads, mature oak trees, and properties averaging 3,600 square feet on at least two acres. Housing consists solely of single-family homes, predominantly with five-plus bedrooms. The community borders Stony Brook Harbor and includes pockets of agricultural land, such as Harmony Vineyards and Bird’s Foot Farm. Local schools are highly rated, with Mills Pond Elementary School, The Stony Brook School, and Smithtown High School East all receiving high marks for their academic programs and extracurricular activities. Residents enjoy access to Long Beach and Avalon Nature Preserve, which offer natural beauty and recreational opportunities. The Deepwells Farm Historical Society hosts an annual haunted Halloween event, adding to the local charm. Dining options include The Trattoria for Italian cuisine and Del Fuego for Tex-Mex, while grocery shopping requires a short drive to nearby St. James. The neighborhood is safer than the national average, and while commuting to Manhattan is possible via the LIRR, it can take between 1 hour 20 minutes to over three hours depending on traffic.

Home Trends in Head of the Harbor, NY

Housing Trends

Median Sale Price
$550,000
Median Single Family Sale Price
$550,000
Average Price Per Sq Ft
$190
Number of Homes for Sale
1
Last 12 months Home Sales
44
Months of Supply
0.30
Median List Price
$665,000
Median Change From 1st List Price
17%
Median Home Sale Price YoY Change
5%
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