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Southold Homes for Sale

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    Showing 181 - 190 of 311 results| view:  results per page« first|...|17|18|19|20|...|last »
    • Sprawling Nassau Point estate with open floor plan, 4 ensuite bedrooms and beautiful pool area. Enjoy summer days by the pool or beach directly across the street. 1st floor features an open floor plan with living, dining and large chef’s kitchen. Also on the 1st floor, a large great room for gathering or watching movies. The hotel-like primary bedroom features peek-a-boo water views and a large primary ensuite bath. Plenty of room to stretch out and relax while retreating to the North Fork summer! Private mooring is available for guests’ use. 36
      Southold, NY 11935
      $48,000
      4 Bedrooms 5 Full Baths Sq. Ft. 5500.00:#
      Single Family For Sale ML# 3532390
      Sprawling Nassau Point estate with open floor plan, 4 ensuite bedrooms and beautiful pool area. Enjoy summer days by the pool or beach directly across the street. 1st floor features an open floor plan with living, dining and large chef’s kitchen. Also on the 1st floor, a large great room for gathering or watching movies. The hotel-like primary bedroom features peek-a-boo water views and a large primary ensuite bath. Plenty of room to stretch out and relax while retreating to the North Fork summer! Private mooring is available for guests’ use.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Welcome to this spectacular waterfront home overlooking the Long Island Sound. This spacious 5000 sqft retreat features an open floor plan with four large bedrooms, 4.5 baths, and a versatile bonus room. Revel in breathtaking sunsets from nearly every room or the expansive back deck and patio. Amenities include a home gym, outdoor shower, multiple fireplaces, and beach access. Just a mile from Greenport Village’s charming shops and restaurants, this property offers the perfect blend of luxury and convenience for your ideal coastal getaway. 56
      Southold, NY 11944
      $45,000
      4 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 5000.00:#
      Single Family For Sale ML# 3565265
      Welcome to this spectacular waterfront home overlooking the Long Island Sound. This spacious 5000 sqft retreat features an open floor plan with four large bedrooms, 4.5 baths, and a versatile bonus room. Revel in breathtaking sunsets from nearly every room or the expansive back deck and patio. Amenities include a home gym, outdoor shower, multiple fireplaces, and beach access. Just a mile from Greenport Village’s charming shops and restaurants, this property offers the perfect blend of luxury and convenience for your ideal coastal getaway.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Immaculate shingle-style home perched above the Long Island Sound. Enjoy endless water views and breathtaking sunsets from the heated pool and private beach. Open floor plan with EIK and fireplace, bedrooms across three floors, including first and second-floor primary suites with private waterside balconies. The large finished basement features a media/game room. The private office is ideal for remote work and has a third private waterside balcony-prime indoor/outdoor summer living just a mile from Greenport Village’s shops and restaurants. Personal property manager to address any tenant needs. Hamptons luxury with North Fork vibes. Available October, November and December 2024. Two-week minimum. 34
      Southold, NY 11944
      $40,000
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 3700.00:#
      Single Family For Sale ML# 3580603
      Immaculate shingle-style home perched above the Long Island Sound. Enjoy endless water views and breathtaking sunsets from the heated pool and private beach. Open floor plan with EIK and fireplace, bedrooms across three floors, including first and second-floor primary suites with private waterside balconies. The large finished basement features a media/game room. The private office is ideal for remote work and has a third private waterside balcony-prime indoor/outdoor summer living just a mile from Greenport Village’s shops and restaurants. Personal property manager to address any tenant needs. Hamptons luxury with North Fork vibes. Available October, November and December 2024. Two-week minimum.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Cutchogue North Fork: Spend August-LD 2025 in this beautifully appointed & very private Long Island Sound front home at 2430 Dignans Road, Cutchogue: come find out why the owners call it North Cliff. Spectacular decks & pool set high on the cliffs overlooking the LI Sound - private easy steps to beach. On the other side forever views of Oregon Road farmland. Published in international Fashion Magazines. Chique but casual Summer home. Inside Outside living. Endless beaches to take in and at night follow the lights from Horton’s Lighthouse over the crescent coastline. Primary Suite with gorgeous long water views from large private sundeck. RP# 0579 50
      Southold, NY 11935
      $40,000
      4 Bedrooms 3 Full Baths 1 Half Bath
      Single Family For Sale ML# 3518964
      Cutchogue North Fork: Spend August-LD 2025 in this beautifully appointed & very private Long Island Sound front home at 2430 Dignans Road, Cutchogue: come find out why the owners call it North Cliff. Spectacular decks & pool set high on the cliffs overlooking the LI Sound - private easy steps to beach. On the other side forever views of Oregon Road farmland. Published in international Fashion Magazines. Chique but casual Summer home. Inside Outside living. Endless beaches to take in and at night follow the lights from Horton’s Lighthouse over the crescent coastline. Primary Suite with gorgeous long water views from large private sundeck. RP# 0579
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • CHIC RETREAT! A glamorous getaway! You won’t know if you are tucked away in Tuscany or the South of France! This recently renovated modernist home is nestled amongst your own private vineyard with incredible farm vistas, imparting a spa retreat vibe. A large pool reaching out towards the horizon. Cozy up by the firepit or have lunch alfresco under the vineyard pergola and enjoy incredible privacy! 3 bedrooms, 2.5 baths, Minutes to the best of everything the North Fork has to offer - local farm stands, beaches, renowned restaurants, (check out Duryea’s) Village Lane, Orient State Park and Greenport Village! This Could Be You! Permit #1128 50
      Southold, NY 11957
      $35,000
      3 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 2110.00:#
      Single Family For Sale ML# 3560540
      CHIC RETREAT! A glamorous getaway! You won’t know if you are tucked away in Tuscany or the South of France! This recently renovated modernist home is nestled amongst your own private vineyard with incredible farm vistas, imparting a spa retreat vibe. A large pool reaching out towards the horizon. Cozy up by the firepit or have lunch alfresco under the vineyard pergola and enjoy incredible privacy! 3 bedrooms, 2.5 baths, Minutes to the best of everything the North Fork has to offer - local farm stands, beaches, renowned restaurants, (check out Duryea’s) Village Lane, Orient State Park and Greenport Village! This Could Be You! Permit #1128
      Presented By: Corcoran  631-765-1300
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • The Old King Farmhouse, located on Indian Neck Lane in Peconic, is an architecturally significant property brimming with history and character. Nestled among the scenic North Fork wineries, farms, and Bay & Sound beaches, the expansive 1.05-acre compound includes an Italianate main house adorned with original Victorian and Arts & Craft details. Inside, you’ll find original plaster walls and crown moldings, intricate parquet floors, and fine woodwork cabinets, shelving, and staircases. Additional interior features include a contemporary kitchen and four working fireplaces, including a wood-burning stove. Outside boasts a 14’ x 36’ saltwater heated pool, a fenced vegetable plot with raised cedar beds, and English-inspired flower gardens framed by mature trees and manicured private hedges. The property is perfect for endless al fresco entertaining, with hundreds of flowering bulbs planted throughout, providing a serene setting. Emphasis has been placed on preserving original details and restoring historic features while providing opportunities to build upon the unique legacy of this rare offering. 72
      Southold, NY 11958
      $35,000
      4 Bedrooms 2 Full Baths 1 Half Bath
      Single Family For Sale ML# 3560573
      The Old King Farmhouse, located on Indian Neck Lane in Peconic, is an architecturally significant property brimming with history and character. Nestled among the scenic North Fork wineries, farms, and Bay & Sound beaches, the expansive 1.05-acre compound includes an Italianate main house adorned with original Victorian and Arts & Craft details. Inside, you’ll find original plaster walls and crown moldings, intricate parquet floors, and fine woodwork cabinets, shelving, and staircases. Additional interior features include a contemporary kitchen and four working fireplaces, including a wood-burning stove. Outside boasts a 14’ x 36’ saltwater heated pool, a fenced vegetable plot with raised cedar beds, and English-inspired flower gardens framed by mature trees and manicured private hedges. The property is perfect for endless al fresco entertaining, with hundreds of flowering bulbs planted throughout, providing a serene setting. Emphasis has been placed on preserving original details and restoring historic features while providing opportunities to build upon the unique legacy of this rare offering.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • This updated and well maintained home and pool is poised on a sprawling three private acres and a true getaway! Boasting four large bedrooms, 3 full recently renovated bathrooms. Backyard oasis with playset and lush lawn. Located less than two miles to Southold’s favorite Cedar Beach and Goose Creek Beach, just over one mile to Croteaux Vineyards- plenty of other wineries, organic farms and restaurants nearby! The space features a first floor living room area with high ceilings and access to an outside wrap around deck which overlooks pool area. Modern Chef’s Kitchen, Dining Area, Bedroom 1, Master Bedroom with a CAL king bed and Bath and access to the Garage. Downstairs has a fun Bar Room with direct access to the Pool, Bedroom 2 has a king bed, Bathroom down the hall, the Laundry Room with Washer/Dryer and another Living Room area with a piano, TV and games. Upstairs, Bedroom 3 has a full over full bunk bed with trundle, daybed and crib if needed. Bedroom 4 has a king bed. You will make wonderful summer memories in this home! Rental Permit #0362 2
      Southold, NY 11971
      $33,000
      4 Bedrooms 3 Full Baths
      Single Family For Sale ML# 3528449
      This updated and well maintained home and pool is poised on a sprawling three private acres and a true getaway! Boasting four large bedrooms, 3 full recently renovated bathrooms. Backyard oasis with playset and lush lawn. Located less than two miles to Southold’s favorite Cedar Beach and Goose Creek Beach, just over one mile to Croteaux Vineyards- plenty of other wineries, organic farms and restaurants nearby! The space features a first floor living room area with high ceilings and access to an outside wrap around deck which overlooks pool area. Modern Chef’s Kitchen, Dining Area, Bedroom 1, Master Bedroom with a CAL king bed and Bath and access to the Garage. Downstairs has a fun Bar Room with direct access to the Pool, Bedroom 2 has a king bed, Bathroom down the hall, the Laundry Room with Washer/Dryer and another Living Room area with a piano, TV and games. Upstairs, Bedroom 3 has a full over full bunk bed with trundle, daybed and crib if needed. Bedroom 4 has a king bed. You will make wonderful summer memories in this home! Rental Permit #0362
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • 2025 Rates: July $32, 500, July-August $67, 500 and August-Labor Day $35, 000. Brand New Modern Farmhouse Completed in 2021 and located in the heart Hog’s Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef’s Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold’s vibrant business district! 31
      Southold, NY 11971
      $32,500
      4 Bedrooms 3 Full Baths 1 Half Bath
      Single Family For Sale ML# 3582922
      2025 Rates: July $32, 500, July-August $67, 500 and August-Labor Day $35, 000. Brand New Modern Farmhouse Completed in 2021 and located in the heart Hog’s Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef’s Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold’s vibrant business district!
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Southold, North Fork: Delightful cottage just up from Founder’s Landing Park, the beach, and the Wharf House. A super convenient ’in town’ location allows instant access to an easy lifestyle. Charming, well-cared-for home features an open floor plan with a large, comfortable living room/dining room, eat-in kitchen with gas range, laundry room, and full bath on primary, plus an additional bath on the second floor with two large bedrooms (queen bed in one, twins and futon in other). Private terrace with firepit, outdoor dining, and bbq area. Onsite parking. Moments to the beach, boating, public transportation, and such popular places as the North Fork Table, North Fork Roasting Co, Einstein Square, and Greenport Village in addition to the numerous wineries and events the North Fork is known for. Flexible rates all year long - whether a winter rental, Summer 2025 or the shoulder season... owner may consider a year-round rental - inquire. Rental Permit# 1216. 27
      Southold, NY 11971
      $30,000
      2 Bedrooms 2 Full Baths
      Single Family For Sale ML# 3588931
      Southold, North Fork: Delightful cottage just up from Founder’s Landing Park, the beach, and the Wharf House. A super convenient ’in town’ location allows instant access to an easy lifestyle. Charming, well-cared-for home features an open floor plan with a large, comfortable living room/dining room, eat-in kitchen with gas range, laundry room, and full bath on primary, plus an additional bath on the second floor with two large bedrooms (queen bed in one, twins and futon in other). Private terrace with firepit, outdoor dining, and bbq area. Onsite parking. Moments to the beach, boating, public transportation, and such popular places as the North Fork Table, North Fork Roasting Co, Einstein Square, and Greenport Village in addition to the numerous wineries and events the North Fork is known for. Flexible rates all year long - whether a winter rental, Summer 2025 or the shoulder season... owner may consider a year-round rental - inquire. Rental Permit# 1216.
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Bucolic, airy, and steps from Orient’s Village lane and beaches. Perfect location. Revel in 2605 Orchard Street, Orient’s grandeur and comfort, set against 15 acres of open meadows with stunning 180 degree tranquil views. This light and bright large home has everything you need to have an idyllic stay in the country. Once inside you can relax into a well appointed beautifully decorated and spacious layout with four bedrooms, all ensuite, eat-in kitchen, a formal dining room, front living room with fireplace and back parlor overlooking garden and pool area, and a large den with fireplace next to kitchen. Outside features a large fenced yard with bluestone area and gardens, specimen trees, a large Patio for gathering and al fresco dining, with an independently fenced in-ground heated pool offers fun and relaxation with views extending over 15 acres of expansive meadows beyond. Rental Permit# 1124 62
      Southold, NY 11957
      $30,000
      4 Bedrooms 5 Full Baths Sq. Ft. 4000.00:#
      Single Family For Sale ML# 3554090
      Bucolic, airy, and steps from Orient’s Village lane and beaches. Perfect location. Revel in 2605 Orchard Street, Orient’s grandeur and comfort, set against 15 acres of open meadows with stunning 180 degree tranquil views. This light and bright large home has everything you need to have an idyllic stay in the country. Once inside you can relax into a well appointed beautifully decorated and spacious layout with four bedrooms, all ensuite, eat-in kitchen, a formal dining room, front living room with fireplace and back parlor overlooking garden and pool area, and a large den with fireplace next to kitchen. Outside features a large fenced yard with bluestone area and gardens, specimen trees, a large Patio for gathering and al fresco dining, with an independently fenced in-ground heated pool offers fun and relaxation with views extending over 15 acres of expansive meadows beyond. Rental Permit# 1124
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
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    12985 Main Road, P.O. Box 63, Mattituck, NY 11952

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