Port Jefferson, NY Homes

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  /42

  $1,699,999

  $100K PRICE DROP Pending

  • 5 Beds
  • 4.5 Baths
  • 6,184 Sq Ft

  83 Cliff Rd, Port Jefferson, NY 11777

  Set on 1.5 acres overlooking a pristine golf course, 83 Cliff Road in Port Jefferson delivers the ultimate private resort lifestyle. This exceptional 5-bedroom, 5-bath residence is surrounded by breathtaking grounds featuring a pool, sports court, and dedicated pickleball area-designed for both elevated entertaining and everyday escape. Whether you're hosting unforgettable gatherings or enjoying

  Bonnie Liotine Coldwell Banker M&D Good Life

  83 Cliff Rd, Port Jefferson, NY 11777
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  $2,920 Per Month

  • 2 Beds
  • 1 Bath
  • 790 Sq Ft
  • Apartment for Rent

  7-2B Dark Hollow Rd Unit 7-2B, Port Jefferson, NY 11777

  Ask about our Outstanding Move-In Specials! Located Upon A Hilltop W/A Waterfall Entrance This Serene Location Is In Perfect Reach To The Port Jefferson Harbor Village. Spacious Apartments With Dining Area & Large Terraces.Conv to Suny Stonybrook, Local Hospitals, Lirr, Shopping! Prices/policies subject to change without notice

  Michelle Holmes Fairfield Properties

  7-2B Dark Hollow Rd Unit 7-2B, Port Jefferson, NY 11777
• 

  $816,000

  Sold May 13, 2026

  146 Crystal Brook Hollow Rd, Port Jefferson, NY 11777

  • 4 Beds
  • 3 Baths
  • 2,358 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Above List Price
  • $346/SF
  • 15 Days On Market

  Current Estimated Value $821,996

  Last Listing Agent Jolie Powell Jolie Powell Realty Inc

  146 Crystal Brook Hollow Rd, Port Jefferson, NY 11777
• 

  Est $825,658

  Not Listed For Sale

  453 W Broadway, Port Jefferson, NY 11777

  • 5 Beds
  • 2.5 Baths
  • 2,800 Sq Ft
  • Built 1901

  453 W Broadway, Port Jefferson, NY 11777

  Last Sold Summary

  • 124 Days On Market

  Last Listing Agent Holly Gottlieb Goldilocks Real Estate
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  $999,000

  $100K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,900 Sq Ft

  87 Soundview Dr, Port Jefferson, NY 11777

  PRICE REDUCED!!! SELLERS ARE MOTIVATED! Move-in ready, this Harbor Hills post modern home offers a blend of sophisticated updates and timeless charm. The home has been fully renovated to meet the expectations of modern living. Boasting 4 bedrooms and 3 full baths, the bright, open-concept main floor is filled with natural light throughout, across its contemporary design. The sleek, updated

  Lisa Minuto Compass Greater NY LLC

  87 Soundview Dr, Port Jefferson, NY 11777
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  /2

  $2,920 Per Month

  • 2 Beds
  • 1 Bath
  • 790 Sq Ft
  • Apartment for Rent

  6-2A Dark Hollow Rd Unit 6-2A, Port Jefferson, NY 11777

  Ask about our Outstanding Move-In Specials! Located Upon A Hilltop W/A Waterfall Entrance This Serene Location Is In Perfect Reach To The Port Jefferson Harbor Village. Spacious Apartments With Dining Area & Large Terraces.Conv to Suny Stonybrook, Local Hospitals, Lirr, Shopping! Prices/policies subject to change without notice

  Michelle Holmes Fairfield Properties

  6-2A Dark Hollow Rd Unit 6-2A, Port Jefferson, NY 11777
• 

  $2,260,000

  Sold Apr 17, 2026

  0 Saints Orchard Rd, Port Jefferson, NY 11777

  • 10 Beds
  • 3.5 Baths
  • 4,000 Sq Ft
  • Built 1910

  Last Sold Summary

  • 22% Below List Price
  • $565/SF
  • 106 Days On Market

  Last Listing Agent Kristen Toffales Serhant East End LLC

  0 Saints Orchard Rd, Port Jefferson, NY 11777
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  Est $816,834

  Not Listed For Sale

  12 Bridle Path Ln, Port Jefferson, NY 11777

  • 3 Beds
  • 2 Baths
  • 2,127 Sq Ft
  • Built 1972

  12 Bridle Path Ln, Port Jefferson, NY 11777

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Devang Patel Douglas Elliman Real Estate
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  $699,999

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,060 Sq Ft

  199 N Country Rd, Port Jefferson, NY 11777

  Charming Cape in the Heart of Port Jefferson VillageFilled with timeless charm and character, this beautifully maintained Cape offers the perfect blend of classic style and comfortable living. The spacious eat in kitchen offers abundant cabinetry and storage, along with a charming Dutch door providing easy access to the outside. Formal dining room opens to the den with gas fireplace and

  Donna McKeown Signature Premier Properties

  199 N Country Rd, Port Jefferson, NY 11777
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  /3

  $3,320 Per Month

  • 2 Beds
  • 2 Baths
  • 1,169 Sq Ft
  • Apartment for Rent

  44 Pinnacle Dr Unit 44, Port Jefferson, NY 11777

  *Ask About Our Rent Specials*. Restrictions Apply* Private Entry 1 & 2 Bedroom Duplex Or Ranch-Style Apartment Townhomes.Kitchens Featuring Whirlpool Appliances. Designer Bathrooms With Ceramic Tile Flooring. Sliding Glass Door To Private Terrace Or Patio. Intrusion Alarms On All Doors & Windows. Professionally Landscaped Grounds.Pet Friendly!. Prices/polices subject to change without notice.,

  Michelle Holmes Fairfield Properties

  44 Pinnacle Dr Unit 44, Port Jefferson, NY 11777
• 

  $1,150,000

  Sold Feb 04, 2026

  4 Old Homestead Rd, Port Jefferson, NY 11777

  • 3 Beds
  • 3.5 Baths
  • 3,300 Sq Ft
  • Built 1988

  Last Sold Summary

  • 11% Below List Price
  • $348/SF
  • 219 Days On Market

  Current Estimated Value $1,160,252

  Last Listing Agent Yaffa Stegemann Douglas Elliman Real Estate

  4 Old Homestead Rd, Port Jefferson, NY 11777
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  Est $845,756

  Not Listed For Sale

  8 Hill Dr, Port Jefferson, NY 11777

  • 3 Beds
  • 3 Baths
  • 2,234 Sq Ft
  • Built 1970

  8 Hill Dr, Port Jefferson, NY 11777

  Last Sold Summary

  • 96 Days On Market

  Last Listing Agent Richard LeDoux BH&G R E Realty Connect
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  /30

  $660,000

  Open Sun 12PM - 2PM $20K PRICE DROP

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

  149 Windward Ct S, Port Jefferson, NY 11777

  Welcome to the largest unit in the highly desirable Highlands community! This beautifully updated corner unit offers exceptional space, privacy, and an impressive list of upgrades throughout.The bright and inviting interior features gleaming hardwood floors on the first level, a stunning renovated kitchen, and a spacious primary suite complete with a dedicated vanity area and an elegant

  Patricia Massimo Coldwell Banker American Homes

  149 Windward Ct S, Port Jefferson, NY 11777
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  $850,000

  Sold Jun 01, 2026

  86 Soundview Dr, Port Jefferson, NY 11777

  • 3 Beds
  • 3 Baths
  • 1,854 Sq Ft
  • Built 1959

  Last Sold Summary

  • 6% Above List Price
  • $458/SF
  • 13 Days On Market

  Current Estimated Value $818,314

  Last Listing Agent Alexia Poulos Douglas Elliman Real Estate

  86 Soundview Dr, Port Jefferson, NY 11777
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  Est $751,148

  Not Listed For Sale

  88 Crystal Brook Hollow Rd, Port Jefferson, NY 11777

  • 3 Beds
  • 2 Baths
  • 2,184 Sq Ft
  • Built 1983

  88 Crystal Brook Hollow Rd, Port Jefferson, NY 11777

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Anthony Vitta Real Broker NY LLC
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  $425,000

  • Land
  • 1 Acre
  • $425,000 per Acre

  105 Laurel Ln, Port Jefferson, NY 11777

  One Acre of Land Ready to Build Your Port Jefferson Dream Home!! On a Private Cul de Sac. Famed Port Jefferson Schools, Private Beaches, Country Club and Beautiful Historic Walking Village!

  Lisa Perry Jolie Powell Realty Inc

  105 Laurel Ln, Port Jefferson, NY 11777
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  $660,000

  Sold Jul 31, 2026

  515 High St Unit 18, Port Jefferson, NY 11777

  • 3 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • Built 1984

  Last Sold Summary

  • 6% Below List Price
  • $287/SF
  • 60 Days On Market

  Last Listing Agent Alexia Poulos Douglas Elliman Real Estate

  515 High St Unit 18, Port Jefferson, NY 11777
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  Est $590,937

  Not Listed For Sale

  33 Sea Court Ln, Port Jefferson, NY 11777

  • 2 Beds
  • 2.5 Baths
  • 1,600 Sq Ft
  • Built 1991

  33 Sea Court Ln, Port Jefferson, NY 11777

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Jolie Powell Jolie Powell Realty Inc
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  /15

  $499,995

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,173 Sq Ft

  15 Leeward Ln, Port Jefferson, NY 11777

  This Sun filled unit is a standout! Open concept living space & kitchen renovation on the main level, second level boasts primary bedroom with vaulted ceiling as well as 2nd bedroom and new luxurious, stunning, spa like bathroom. Ground level offers additional space for laundry, storage/gym/home office. All nestled in private location with lovely front & rear decks. Community amenities include

  Peter Velez Deal House Realty Inc.

  15 Leeward Ln, Port Jefferson, NY 11777
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  $2,250,000

  Sold Dec 22, 2025

  1 Uva Way, Port Jefferson, NY 11777

  • 6 Beds
  • 9 Baths
  • 9,000 Sq Ft
  • Built 2004

  Last Sold Summary

  • 18% Below List Price
  • $250/SF
  • 152 Days On Market

  Current Estimated Value $2,285,667

  Last Listing Agent Blondie Lee Ramos Howard Hanna Coach

  1 Uva Way, Port Jefferson, NY 11777
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  Est $743,694

  Not Listed For Sale

  26 Sea Court Ln, Port Jefferson, NY 11777

  • 3 Beds
  • 2.5 Baths
  • 1,876 Sq Ft
  • Built 1991

  26 Sea Court Ln, Port Jefferson, NY 11777

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Julie Poidomani BH&G R E Realty Connect
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  $649,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,727 Sq Ft

  213 Windward Ct N, Port Jefferson, NY 11777

  Welcome to the market this beautifully renovated 3-bedroom, 2.5-bath end-unit condo in the desirable Highlands community. Completely updated top to bottom in 2021, this move-in-ready home offers modern finishes, thoughtful upgrades, and exceptional privacy. The stunning redesigned kitchen features custom cabinetry, Quartz countertops, and GE Profile appliances, creating the perfect space for both

  Ryan Verbarg Peconic Realty Group LLC

  213 Windward Ct N, Port Jefferson, NY 11777
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  $950,000

  Sold Jun 15, 2026

  107A Scraggy Hill Rd, Port Jefferson, NY 11777

  • 4 Beds
  • 3.5 Baths
  • 2,646 Sq Ft
  • Built 1995

  Last Sold Summary

  • $359/SF
  • 27 Days On Market

  Last Listing Agent Maria Palmar Maria S Palmar

  107A Scraggy Hill Rd, Port Jefferson, NY 11777
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  Est $593,143

  Not Listed For Sale

  20 Sea Court Ln, Port Jefferson, NY 11777

  • 2 Beds
  • 2.5 Baths
  • 1,572 Sq Ft
  • Built 1991

  20 Sea Court Ln, Port Jefferson, NY 11777

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Jill Kaplan Signature Premier Properties
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  /31

  $435,000

  $10K PRICE INCREASE Pending

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft

  88 Leeward Ct, Port Jefferson, NY 11777

  Welcome to this beautifully appointed second-floor end-unit condominium in the sought-after Highlands at Port Jefferson.This bright and inviting home offers the privacy and abundant natural light that only an end unit can provide. Beautiful custom moldings add timeless elegance throughout the living spaces, creating a warm and sophisticated atmosphere.The spacious primary suite

  Maria Palmar Maria S Palmar

  88 Leeward Ct, Port Jefferson, NY 11777
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  $749,990

  Sold Oct 23, 2025

  24 Midland Ave, Port Jefferson, NY 11777

  • 4 Beds
  • 2.5 Baths
  • 2,408 Sq Ft
  • Built 2004

  Last Sold Summary

  • 5% Below List Price
  • $311/SF
  • 60 Days On Market

  Current Estimated Value $801,681

  Last Listing Agent John Sanders Shea & Sanders Real Estate Inc

  24 Midland Ave, Port Jefferson, NY 11777
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  Est $559,803

  Not Listed For Sale

  5 Sea Court Ln, Port Jefferson, NY 11777

  • 2 Beds
  • 2.5 Baths
  • 1,572 Sq Ft
  • Built 1991

  5 Sea Court Ln, Port Jefferson, NY 11777

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent John Hermanowski Signature Premier Properties
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  $1,200,000

  Open Sun 1PM - 2:30PM

  • 5 Beds
  • 3.5 Baths
  • 3,012 Sq Ft

  30 Fairway Dr, Port Jefferson, NY 11777

  Golf players, Tennis lovers, Boaters & Beach goers! This sprawling 5 bedroom, 3.5 bath ranch that backs up to the lush, green Port Jefferson golf course is not just a house, it's a Lifestyle! A sunfilled open floor plan with vaulted ceilings & skylights leads to the family room with Fireplace and kitchen with breakfast bar. The sunken Living Room brings drama to the party, and the 2 Primary

  Julie Malsky RE/MAX Signature Real Estate

  30 Fairway Dr, Port Jefferson, NY 11777
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  $660,000

  Sold Oct 03, 2025

  508 W Broadway, Port Jefferson, NY 11777

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1929

  Last Sold Summary

  • 8% Below List Price
  • $367/SF
  • 111 Days On Market

  Current Estimated Value $746,377

  Last Listing Agent Jolie Powell Jolie Powell Realty Inc

  508 W Broadway, Port Jefferson, NY 11777
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  Est $667,986

  Not Listed For Sale

  10 Woodside Ave, Port Jefferson, NY 11777

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1965

  10 Woodside Ave, Port Jefferson, NY 11777

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Kerri Passamenti BH&G R E Realty Connect
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  /33

  $690,000

  Pending

  • 7 Beds
  • 4 Baths
  • 4,000 Sq Ft

  127 Barnum Ave, Port Jefferson, NY 11777

  Circa1890's rectory and original Barnum House now for sale!Possible 2 family home with proper permits. Needs TLC but some new mechanicals. Almost 4000 s/f of living space. 7/8 bedrooms, 4 fbths, 200 amp service, original white oak beams , coal chute in bsmt, spacious living areas, endless possibilities, walk to all in village. Perfect for those seeking a piece of history. Brookhaven Town

  Jolie Powell Jolie Powell Realty Inc

  127 Barnum Ave, Port Jefferson, NY 11777
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  $875,000

  Sold Jun 09, 2026

  117 Liberty Ave, Port Jefferson, NY 11777

  • 3 Beds
  • 1 Bath
  • 2,000 Sq Ft
  • Built 1902

  Last Sold Summary

  • 5% Below List Price
  • $438/SF
  • 28 Days On Market

  Current Estimated Value $857,632

  Last Listing Agent Alexia Poulos Douglas Elliman Real Estate

  117 Liberty Ave, Port Jefferson, NY 11777
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  Est $901,540

  Not Listed For Sale

  18 Midland Ave, Port Jefferson, NY 11777

  • 6 Beds
  • 4.5 Baths
  • 3,182 Sq Ft
  • Built 1996

  18 Midland Ave, Port Jefferson, NY 11777

  Last Sold Summary

  • 204 Days On Market

  Last Listing Agent David Friedman Howard Hanna Coach
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  /34

  $1,000,000

  $199K PRICE DROP Pending

  • 4 Beds
  • 4 Baths
  • 3,039 Sq Ft

  21 Druid Hill Rd, Port Jefferson, NY 11777

  MAJOR PRICE IMPROVEMENT! Welcome to this beautifully secluded residence in the prestigious Incorporated Village of Belle Terre, where privacy, comfort, and timeless North Shore living come together. Nestled on a serene, tree-lined property, this spacious four-bedroom home offers a rare opportunity to enjoy one of Long Island’s most sought-after waterfront communities.Designed for both

  Erick Grier Keller Williams Points North

  21 Druid Hill Rd, Port Jefferson, NY 11777
• 

  $900,000

  Sold Nov 03, 2025

  22 Druid Hill Rd, Port Jefferson, NY 11777

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 1961

  Last Sold Summary

  • 25% Below List Price
  • $346/SF
  • 155 Days On Market

  Current Estimated Value $1,016,376

  Last Listing Agent Donna Wissman Douglas Elliman Real Estate

  22 Druid Hill Rd, Port Jefferson, NY 11777
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  Est $886,416

  Not Listed For Sale

  34 Midland Ave, Port Jefferson, NY 11777

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft
  • Built 2016

  34 Midland Ave, Port Jefferson, NY 11777

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent John Sanders Shea & Sanders Real Estate Inc
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  /21

  $849,900

  • 4 Beds
  • 3.5 Baths
  • 3,200 Sq Ft

  5 Princess Tree Ct, Port Jefferson, NY 11777

  This Luxury Townhouse has it all, Huge vaulted ceiling Foyer with an Open floor plan that leads you through spacious rooms and tremendous closets. Many Updates... New Gas Heating Unit and Central Air Conditioning, Some new Anderson Windows, New Refrigerator, New Trex Patio, Young Roof and rain gutters, Recessed Lighting. A wood Burning Fireplace in the Livingroom that will comfort the whole

  Anthony Rubino Leading Edge R E Services

  5 Princess Tree Ct, Port Jefferson, NY 11777
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  $589,500

  Sold Mar 26, 2026

  122 Liberty Ave, Port Jefferson, NY 11777

  • 2 Beds
  • 1 Bath
  • 824 Sq Ft
  • Built 1940

  Last Sold Summary

  • $715/SF
  • 60 Days On Market

  Current Estimated Value $596,556

  Last Listing Agent Julie Malsky RE/MAX Signature Real Estate

  122 Liberty Ave, Port Jefferson, NY 11777
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  Est $842,372

  Not Listed For Sale

  1 Willis Ave, Port Jefferson, NY 11777

  • 5 Beds
  • 3 Baths
  • 2,422 Sq Ft
  • Built 1950

  1 Willis Ave, Port Jefferson, NY 11777

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Julie Vitrano OverSouth LLC
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  /35

  $815,000

  Open Sat 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 2,500 Sq Ft

  111 Red Oak Ct, Port Jefferson, NY 11777

  Discover the charm of Port Jefferson Village in this beautifully designed one story prestigious ranch style home with finished basement. Elegant architectural details, 3 year old roof, gourmet Kitchen, updated Baths, mature landscaping are part of the features found in this turn key residence. Designed for everyday living and entertaining, the private back yard with in-ground pool, patio and

  Patricia Nicklaus Howard Hanna Coach

  111 Red Oak Ct, Port Jefferson, NY 11777

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