Greenport West, NY Homes for Sale

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  /14

  $999,000

  $101K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft

  136 Bayview Ave, Southold, NY 11971

  The Summer has never been sweeter in this coastal cottage right on the water. Peaceful breezes blow while you sit on the covered deck and watch the paddle boarders go by. Located on a dead-end street on Hashamomuck Pond, this home offers a private dock, 2 bedrooms, warm oak floors, spacious living room, and waterfront views galore. Enjoy boating, kayaking, paddleboarding, fishing, and swimming

  

  Joseph Nina

  Douglas Elliman Real Estate

  136 Bayview Ave, Southold, NY 11971
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  /35

  $4,800,000

  • 5 Beds
  • 3.5 Baths
  • 3,325 Sq Ft

  90 Peconic Ave, Shelter Island, NY 11964

  Held by a single family for nearly a century, 90 Peconic Avenue carries the kind of history that can't be manufactured - a deep sense of place, of summers lived well, of a waterfront that has remained unchanged while the world around it evolved. Custom built by Reich Eklund in 1985 and thoughtfully maintained, this classic Shelter Island shingled beach house sits on a level acre along one of the

  

  Elizabeth Melichar

  Serhant East End LLC

  90 Peconic Ave, Shelter Island, NY 11964
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  /10

  $605,000

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

  2555 Youngs Ave Unit 11A, Southold, NY 11971

  Welcome to this corner residence at Founders Village, where easy, low-maintenance living meets the North Fork lifestyle.This 1,200-square-foot home offers 2 bedrooms, 2 full baths and a full basement, giving you valuable storage and extra space that can be hard to find when downsizing to condominium living.The corner location provides added green space on multiple sides, along

  

  Timothy O'Keefe

  Signature Premier Properties

  2555 Youngs Ave Unit 11A, Southold, NY 11971
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  /30

  $5,500,000

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

  11 Sunnyside Ave, Shelter Island Heights, NY 11965

  An architecturally significant modern retreat set on two private acres within coveted Shelter Island Heights owners association. Floor-to-ceiling glass dissolves the boundary between indoors and out, framing the surrounding natural environment from nearly every room. Conceived by developer Angelo Varischetti in collaboration with the award-winning team at WE+ Architecture & Design, the home is a

  

  Benjamin Dixon

  Douglas Elliman Real Estate

  11 Sunnyside Ave, Shelter Island Heights, NY 11965
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  /6

  $485,000

  $60K PRICE DROP

  • Land
  • 29,185 Sq Ft
  • $723,881 per Acre

  620 Kerwin Blvd, Greenport West, NY 11944

  Wonderful opportunity to build a Residential Home in the highly-desirable and sought-after Town of Greenport! Greenport offers a vast array of Art Galleries, Museums, Fishing Charters, Boutique Shops, Breweries and Cideries, Waterfront Dining and other Entertainment Venues. This generously sized .67 Acre Level Parcel is just waiting for you to create that special home you've always been dreaming

  

  Richard Connelly

  Douglas Elliman Real Estate

  620 Kerwin Blvd, Greenport West, NY 11944
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  /50

  $1,350,000

  • 2 Beds
  • 2 Baths
  • 1,464 Sq Ft

  11 Jaspa Rd, Shelter Island, NY 11964

  Welcome to your private Shelter Island retreat, where comfort, character, privacy, and exceptional outdoor living come together. This inviting 2-bedroom, 2-bath home offers thoughtfully designed spaces, beautiful hardwood flooring throughout, and an impressive collection of amenities for year-round living or the perfect island escape. The well-appointed kitchen features a refrigerator,

  

  Karen Neglia

  RustyCap O Inc

  11 Jaspa Rd, Shelter Island, NY 11964
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  /39

  $1,149,900

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  380 Homestead Way, Greenport, NY 11944

  Welcome to this beautifully appointed single-family residence ideally situated just minutes from the charming village of Greenport. Blending modern amenities with classic coastal charm, this property offers not only an exceptional retreat in one of Long Island’s most sought-after locations—but also a compelling opportunity as a fully functional or potential income-producing short-term rental.

  Jules Zaphire Locqube New York, Inc.

  380 Homestead Way, Greenport, NY 11944
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  /43

  $1,250,000

  • 3 Beds
  • 2.5 Baths
  • 2,083 Sq Ft

  515 The Greenway, East Marion, NY 11939

  Classic Georgian Colonial set on approximately 0.47 acres, enhanced by mature spruce trees that offer natural privacy. The first floor features a welcoming living room with brick fireplace, formal dining room, family room, eat-in kitchen, conveniently located powder room, and access to the one-car garage. Upstairs are three bedrooms, including a spacious primary suite with private bath and large

  Michael Graziose Redfin Real Estate

  515 The Greenway, East Marion, NY 11939
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  /38

  $1,585,000

  Open Sun 1:30PM - 3PM $200K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,392 Sq Ft

  90 Caiola Ct, Greenport, NY 11944

  Welcome to 90 Caiola Court, nestled within the highly sought-after waterfront community of Rock Cove Estates in the charming hamlet of Greenport. Built in 2007 and impeccably maintained, this Post Modern residence makes an immediate impression with its mature specimen landscaping, manicured grounds, and timeless curb appeal. Step inside to a grand, light-filled foyer featuring soaring ceilings,

  William Walters Daniel Gale Sothebys Intl Rlty

  90 Caiola Ct, Greenport, NY 11944
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  /11

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  2555 Youngs Ave Unit 3C, Southold, NY 11971

  Unit 3C offers a rare opportunity to create something truly your own. This 2-bedroom, 2-bath condo is ready for a new vision and offers the perfect blank canvas for buyers who would rather customize than compromise. There is tremendous potential to thoughtfully update the home to your style, selecting the finishes, fixtures, colors, and details you actually want along the way. The unfinished

  Thomas McCarthy Thomas J McCarthy Real Estate

  2555 Youngs Ave Unit 3C, Southold, NY 11971
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  /8

  $629,000

  • Land
  • 16,117 Sq Ft
  • $1,700,000 per Acre

  2560 Hyatt Rd, Southold, NY 11971

  Ideally Located Vacant Land. A Rare Opportunity to Create Your Own North Fork Retreat or Year-Round Home on Desirable Hyatt Road, a Quiet Setting Just Off Soundview Avenue in Southold. This Ideally Located Vacant Parcel is Just a Short Distance from Memorable McCabe’s Town Beach. The Lot is Reported to Include Coveted Deeded Rights to a Private Long Island Sound Beach. Enjoy the Tranquility of a

  Paul Loeb Douglas Elliman Real Estate

  2560 Hyatt Rd, Southold, NY 11971
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  /23

  $1,100,000

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

  435 Sound Rd, Greenport, NY 11944

  What stands out about this home is how established and inviting it already feels. Mature trees and thoughtful landscaping surround the property, creating a beautiful setting from the moment you arrive. The covered front porch is a perfect place to sit and take in the changing colors of spring and summer, including the striking blue blossoms of the mature Vitex that become a highlight of the

  Jerry Cibulski Century 21 Albertson Realty

  435 Sound Rd, Greenport, NY 11944
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  /40

  $2,650,000

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

  56765 Route 48, Greenport, NY 11944

  Beautiful, expansive soundfront retreat offering rare, direct waterfront access with no bluff and sweeping 180-degree panoramic views. Set on .75 acres, this exceptional 3-bedroom, 2-bath home features a waterside gunite pool perfectly positioned to capture breathtaking sunsets over the Sound. The interior showcases modern finishes and an open-concept layout designed for effortless indoor-outdoor

  Kris Pilles East End Luxury Ltd

  56765 Route 48, Greenport, NY 11944
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  /23

  $999,999

  $200K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,266 Sq Ft

  16 Bowditch Rd, Shelter Island, NY 11964

  Charming cottage-style home offering 3 bedrooms and 2 full baths in a highly desirable central location. Just moments from beautiful beaches, local restaurants, and boutique shops, this inviting property blends classic charm with modern updates. Renovated in 2019 with additional recent improvements, the home features comfortable living spaces filled with warmth and character. Outside, enjoy a

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  16 Bowditch Rd, Shelter Island, NY 11964
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  /25

  $1,550,000

  $345K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,857 Sq Ft

  1900 Gillette Dr, East Marion, NY 11939

  Modern Design Meets Coastal LivingWelcome to your brand-new custom build in East Marion-crafted with an eye for detail and built for everyday luxury. This 4-bedroom, 3.5-bath home, complete with a spacious primary en-suite, balances timeless design with modern conveniences in a coveted beach community. Step inside to soaring ceilings, red oak select flooring, and Allwood custom cabinetry

  Sheri Winter Parker Corcoran

  1900 Gillette Dr, East Marion, NY 11939
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  /13

  $925,000

  • 2 Beds
  • 1 Bath
  • 925 Sq Ft

  738 Conklin Rd, Greenport, NY 11944

  The first thing I noticed about this house was actually the side entrance. There’s this casual mudroom entry with pieces of driftwood collected from the beach tucked around the railings, and it immediately gives the house that relaxed coastal cottage feeling.Inside, the morning light is probably one of my favorite things. The corner dining nook has windows on both sides, so the sunlight just

  Jerry Cibulski Century 21 Albertson Realty

  738 Conklin Rd, Greenport, NY 11944
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  /29

  $2,199,000

  • 5 Beds
  • 4 Baths
  • 2,642 Sq Ft

  64A N Midway Rd, Shelter Island, NY 11964

  A rare turnkey Shelter Island retreat with two distinct homes tucked away on nearly an acre in the heart of Shelter Island, 64A North Midway Road presents a truly unique opportunity to own two homes on one private property. Surrounded by mature trees, expansive lawns, and a picturesque pond next door, this exceptional estate blends privacy, flexibility, and timeless charm. This rare property

  Christine Beckwith Douglas Elliman Real Estate

  64A N Midway Rd, Shelter Island, NY 11964
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  /4

  $1,600,000

  • Land
  • 2 Acres
  • $800,000 per Acre

  55975 Route 25, Southold, NY 11971

  2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Commercial Mix. Four Buildings Possible As Of Right. Excellent Route 25 Exposure & Great Location In Center Of The Hamlet! Commercial Listing MLS# 3530579

  Colin McCarthy Thomas J McCarthy Real Estate

  55975 Route 25, Southold, NY 11971
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  /50

  $1,529,000

  $90K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,564 Sq Ft

  2655 Rocky Point Rd, East Marion, NY 11939

  Experience the beauty of coastal living with this young Colonial built in 2006 and set on 1.2 verdant level acres of privacy and seclusion. The expansive front yard, complemented by a grand circular driveway, creates a lasting first impression. The welcoming covered front porch is perfect for sipping your morning coffee while the equally expansive rear yard is ideal for star gazing on warm summer

  Connie Liappas Compass Greater NY LLC

  2655 Rocky Point Rd, East Marion, NY 11939
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  /3

  $824,000

  • Land
  • 26,571 Sq Ft
  • $1,350,820 per Acre

  705 Wildberry Ln, Southold, NY 11971

  A rare opportunity to create a custom North Fork residence in desirable Wildberry Fields. This .61-acre level, wooded parcel is situated on a private 9-lot country road and backed by picturesque vineyards, offering beautiful vineyard views and a peaceful, private setting.Protective covenants help preserve the character and value of the community, requiring residences of more than 3,000

  Kim Pirreca BERKSHIRE HATHAWAY

  705 Wildberry Ln, Southold, NY 11971
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  /25

  $2,799,000

  New Construction $200K PRICE DROP

  • 8 Beds
  • 7 Baths
  • 5,600 Sq Ft

  1350 Hortons Ln, Southold, NY 11971

  2-Acre Private Oasis with Custom "To Be Built" Luxury Home - Excellent Location Near Town, Beaches & Vineyards! Discover the perfect blend of privacy, luxury and convenience with this exceptional vacant lot, tucked away in a serene, secluded setting --- Yet just minutes from downtown, pristine beaches, and world-class vineyards, shopping and dining. Plans are in-place for a "To Be Built" custom

  Thomas McCarthy Thomas J McCarthy Real Estate

  1350 Hortons Ln, Southold, NY 11971
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  /3

  $1,550,000

  New Construction $150K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 2,215 Sq Ft

  500 Summer Ln, Southold, NY 11971

  The classic North Fork lifestyle you have been waiting for has finally arrived. Nestled in a quiet Southold neighborhood, 500 Summer Lane offers the rare opportunity to create a retreat just moments from the beaches, vineyards, and beloved local destinations that define the North Fork. Here, tranquility meets convenience—you’re never far from the shoreline or the vibrant heartbeat of the

  Catherine Flood Compass Greater NY LLC

  500 Summer Ln, Southold, NY 11971
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  /16

  $1,595,000

  • Land
  • 27,007 Sq Ft
  • $2,572,581 per Acre

  9 Bay Shore Dr, Shelter Island, NY 11964

  Rare opportunity to own .62 Acres of waterfront buildable land along West Neck creek, offering a beautiful setting with water views and direct access to the shoreline. Nestled within the peaceful Silver Beach community, this private and tranquil property is surrounded by nature and offers an exceptional opportunity to create a waterfront retreat. Across the water, protected preserved land ensures

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  9 Bay Shore Dr, Shelter Island, NY 11964
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  /49

  $1,297,000

  • 4 Beds
  • 2 Baths
  • 1,784 Sq Ft

  407 Wiggins St, Greenport, NY 11944

  Prime location legal 2-family featuring 2 separate 2-bedroom units. An exceptional opportunity for an end user seeking supplemental rental income or for an investor pursuing a desirable multi-unit asset. Set amid the charm of sought-after Greenport Village, this versatile property features a porch, deck, patio, and 1-car garage, along with additional outdoor amenities including a cabana and hot

  Douglas Cabral Century 21 Excelsior Realty

  407 Wiggins St, Greenport, NY 11944
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  /26

  $799,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  650 Greenfields Ln, Southold, NY 11971

  Welcome to 650 Greenfields Lane, an inviting ranch-style home on just shy an acre of property, nestled in the heart of Southold, NY. This charming residence offers three bedrooms, and two full bathrooms, which includes a primary en suite that overlooks the back yard. The home's cozy living room features a traditional fireplace, perfect for creating a warm and welcoming atmosphere. The eat-in

  Barbara Poliwoda Douglas Elliman Real Estate

  650 Greenfields Ln, Southold, NY 11971
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  /10

  $775,000

  $50K PRICE DROP

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

  429 Kaplan Ave, Greenport, NY 11944

  Charming Greenport Village GetawayEnjoy the best of the North Fork from this inviting 3-bedroom, 2-bath home, perfectly located near all that Greenport Village has to offer. Stroll to Mitchell Park, waterfront dining, restaurants, shops, and the Shelter Island Ferry, or spend the day exploring nearby vineyards and Greenport Harbor Brewing Company.A wonderful opportunity to enjoy

  Mary Terry MCKENNASHEA LLC

  429 Kaplan Ave, Greenport, NY 11944
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  /21

  $2,100,000

  • 5 Beds
  • 4.5 Baths
  • 3,500 Sq Ft

  151 Bay Ave, Greenport, NY 11944

  This beautiful Queen Ann Victorian home includes a priceless location in the heart of Greenport Village. Built in 1897, many of the fine architectural detail in this home is still present today. There are 5 bedrooms in which three of them are ensuites. The property is loaded with gorgeous specimen plantings. There is a large barn behind the pergola covered courtyard. This home makes a perfect Bed

  Barbara Poliwoda Douglas Elliman Real Estate

  151 Bay Ave, Greenport, NY 11944
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  /37

  $574,999

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  2600 Boisseau Ave, Southold, NY 11971

  Welcome to 2600 Boisseau Avenue, the best deal in all of Southold. This well-maintained 3-bedroom, 1-bath ranch situated on a spacious .39-acre property in the heart of the North Fork will not disappoint. Offering comfortable single-level living with plenty of potential, this home is a wonderful opportunity to enjoy everything the Southold lifestyle has to offer. Inside, you'll find a functional

  Zachary Scher Signature Premier Properties

  2600 Boisseau Ave, Southold, NY 11971
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  /23

  $999,750

  $600K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft

  336 2nd St, Greenport, NY 11944

  BRING ALL OFFERSGREENPORT, NY — RELAUNCHED UNDER $1 MILLIONLimited supply. Strong demand. Location, location, location.Real estate values have always been influenced by location, supply and demand—and Greenport continues to attract buyers looking for the unique lifestyle of the North Fork.Now is the time to take another look at 336 2nd Street, newly offered at

  Ron Moschetta Keller Williams Realty Greater

  336 2nd St, Greenport, NY 11944
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  /33

  $1,249,000

  • 3 Beds
  • 3.5 Baths
  • 1,700 Sq Ft

  Unlisted Address

  Stylish Heritage Farmhouse:Dating to approximately 1910, this beautifully reimagined Queen Anne–inspired country home preserves a tangible connection to East Marion’s past. Set along the historic route once known as Kings Highway and Sunset Trail—today’s Main Road—and near Marion Lake, the residence was built when the hamlet still reflected its longstanding agricultural and maritime heritage

  Nicholas Planamento William Raveis New York LLC

  Unlisted Address
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  /32

  $1,495,000

  • 4 Beds
  • 2 Baths
  • 2,074 Sq Ft

  6 Oxford Ave, Shelter Island, NY 11964

  Rare opportunity to own a charming early-1900s Victorian farmhouse in the historic Heights. Set on a quiet road, this inviting home features an extra-large yard perfect for entertaining and a welcoming wraparound porch ideal for relaxing summer evenings. Inside, the home boasts a spacious living room with a wood-burning fireplace, a gracious parlor, formal dining room, and a first-floor bedroom

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  6 Oxford Ave, Shelter Island, NY 11964
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  /5

  $799,000

  • Land
  • 2.29 Acres
  • $348,908 per Acre

  1350 Hortons Ln, Southold, NY 11971

  Discover The Perfect Canvas For Your Dream Estate On This Expansive 2+ Acre Lot Offering The Ideal Balance Of Privacy And Convenience. Nestled In A Serene Setting, Yet Just Moments Away From The Vibrant Town Life; You’ll Be Close To Fine Dining, Shopping, And Everything The North Fork Has To Offer. This Unique Parcel Comes With Suffolk County Health Department Approval For An 8-Bedroom

  Thomas McCarthy Thomas J McCarthy Real Estate

  1350 Hortons Ln, Southold, NY 11971
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  /23

  $1,200,000

  • 2 Beds
  • 1.5 Baths
  • 886 Sq Ft

  1405 Village Ln, Orient, NY 11957

  A beautifully preserved 19th-century Victorian home set in the heart of Orient Village. The large screened three-season porch opens onto a picturesque rear garden, perfect for entertaining. A detached garage, recently renovated with heat, A/C, and EV charging — currently an art studio, but fully functional as a garage with intact new garage doors. The first-floor features custom cabinetry, a

  Janet Markarian Daniel Gale Sothebys Intl Rlty

  1405 Village Ln, Orient, NY 11957
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  /50

  $1,849,000

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  1025 9th St, Greenport, NY 11944

  Greenport Gem — Timeless Elegance & Coastal LivingTucked privately behind tall hedges on a beautifully landscaped, gated corner property, this stately 1930s American Square offers an exceptional blend of historic character, refined comfort, and the coveted Greenport lifestyle.Meticulously restored in 2012 and gently lived in since, the home retains its original woodwork, doors,

  Paul Loeb Douglas Elliman Real Estate

  1025 9th St, Greenport, NY 11944
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  /33

  $1,277,000

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  1025 Seawood Dr, Southold, NY 11971

  Welcome to 1025 Seawood Drive, where space, comfort, and the North Fork lifestyle come together beautifully!Experience the relaxed sophistication of North Fork living in this beautifully, maintained, move-in-ready 4 bedroom, 3.5 bath Colonial in the heart of Southold. Filled with natural light and designed for modern living this home features 9' ceilings, hardwood floors and an easy-flowing

  Clorinda Tagios Douglas Elliman Real Estate

  1025 Seawood Dr, Southold, NY 11971
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  /30

  $1,300,000

  • 3 Beds
  • 3 Baths
  • 1,815 Sq Ft

  10940 Main Rd, East Marion, NY 11939

  This ranch style home offers a blend of comfort, convenience, and opportunity. With three spacious bedrooms and three beautifully finished bathrooms, the home provides generous space for relaxation, work, or entertaining. The well-appointed kitchen features a stainless-steel appliance package, Quartz countertops, and a Thor range and hood, combining style with functionality. The homes’ living

  Kristy Naddell Douglas Elliman Real Estate

  10940 Main Rd, East Marion, NY 11939
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  /28

  $929,000

  $20K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 580 Sq Ft

  1100 (aka 702 Linnet 7th St, Greenport, NY 11944

  Charming Cedar Shake Cottage on a Desirable Corner Lot. Enjoy it Now, and/or Expand Extensively in the Future with Proper Permits. The Spacious Deck, Brick Patio, Mature Landscaping, and Lush Shrubbery Create a Private and Secluded Backyard Retreat. Just 3–4 blocks to Beautiful Bay Beaches and 6 Blocks to Greenport Village, Marina, Shops, Restaurants, and NYC Transportation. Start Living the Good

  Paul Loeb Douglas Elliman Real Estate

  1100 (aka 702 Linnet 7th St, Greenport, NY 11944
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  /3

  $699,000

  • Land
  • 32,670 Sq Ft
  • $932,000 per Acre

  49295 Route 25, Southold, NY 11971

  High-Visibility Commercial Land in Southold. Rare opportunity to acquire a highly visible vacant parcel along main road in Southold Town. Zoned "General Business", the property offers a wide range of potential uses and flexibility for an owner-user, investor, or contractor. Permitted uses include retail and wholesale businesses, convenience store, contractor-related uses, storage, and residential

  Melissa Principi Douglas Elliman Real Estate

  49295 Route 25, Southold, NY 11971
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  /33

  $2,695,000

  • 5 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  605 Cedar Dr, Southold, NY 11971

  This charming cedar shingle Cape has been expanded and completely renovated, resulting in a home that exudes a timeless sense of place across three full floors of living space. With five bedrooms and four bathrooms, the home expands comfortably for guests yet feels equally intimate for smaller gatherings, striking a perfect balance for those looking to host but also enjoy a refined and

  Bridget Elkin Compass Greater NY LLC

  605 Cedar Dr, Southold, NY 11971
• 

  

  /20

  $1,999,999

  • 6 Beds
  • 5.5 Baths
  • 6,098 Sq Ft

  4 Bayview Ave, Bay Shore, NY 11706

  Welcome to 4 Bayview Avenue, a remarkable residence nestled in the historic heart of Shelter Island Heights. This expansive property, designed with the art of entertaining in mind, offers a generous six bedrooms and five and a half bathrooms, providing an abundance of space for comfortable living. Upon entering, you'll be welcomed by an array of inviting sitting areas spread throughout the main

  Christine Beckwith Douglas Elliman Real Estate

  4 Bayview Ave, Bay Shore, NY 11706

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