Southold NY Real Estate & Homes for Sale

Southold-Reydon Shores-Inviting 3/4 acre landscaped property with specimen plantings is the backdrop for this spacious well-maintained ranch in the sought after waterfront community of Reydon Shores. Easy access to the Association Bay Beach and protected Marina. Plenty of room for family and guests to gather in the large living room with a wood burning fireplace and doors to the outside rear deck. Formal dining room, eat-in kitchen open to living room, and an additional sitting room. Two generous ensuite primary bedrooms. Additional guest bedroom and hall bathroom. Hardwood floors. The heated inground swimming pool catches the sun throughout the day and is surrounded by a paver patio. YOU can have a lot of fun here! A move-in ready North Fork home just waiting for you to enjoy.

Southold-Reydon Shores-Inviting 3/4 acre landscaped property with specimen plantings is the backdrop for this spacious well-maintained ranch in the sought after waterfront community of Reydon Shores. Easy access to the Association Bay Beach and protected Marina. Plenty of room for family and guests to gather in the large living room with a wood burning fireplace and doors to the outside rear deck. Formal dining room, eat-in kitchen open to living room, and an additional sitting room. Two generous ensuite primary bedrooms. Additional guest bedroom and hall bathroom. Hardwood floors. The heated inground swimming pool catches the sun throughout the day and is surrounded by a paver patio. YOU can have a lot of fun here! A move-in ready North Fork home just waiting for you to enjoy.

Introducing 3715 Main Bayview Road in Southold, NY. This modern home offers 3 bedrooms, 2.5 bathrooms, and a spacious lot spanning 39582 square feet. Inside, the open concept living creates a welcoming ambiance for entertainment. The Chefs kitchen has modern appliances with ample counter space and storage. The main floor Master ensuite is its own private sanctuary. Outside, enjoy the tranquil back yard and direct creek front access for kayaking or paddle boarding to near by Goose Creek Beach. Schedule a showing today and experience the allure of 3715 Main Bayview Road for yourself.

Introducing 3715 Main Bayview Road in Southold, NY. This modern home offers 3 bedrooms, 2.5 bathrooms, and a spacious lot spanning 39582 square feet. Inside, the open concept living creates a welcoming ambiance for entertainment. The Chefs kitchen has modern appliances with ample counter space and storage. The main floor Master ensuite is its own private sanctuary. Outside, enjoy the tranquil back yard and direct creek front access for kayaking or paddle boarding to near by Goose Creek Beach. Schedule a showing today and experience the allure of 3715 Main Bayview Road for yourself.

**Luxurious Coastal Retreat in Southold's Prestigious Deer Run** Nestled on a private, nearly 2-acre lot within the exclusive Deer Run community, this remarkable 5-bedroom, 9-bathroom cedar shake home epitomizes coastal luxury and refined living. Spanning an impressive 6,000 square feet and surrounded by 37 acres of preserved land, this home is a haven of grandeur and comfort. Its thoughtful design features transom windows, coffered ceilings, paneled walls, and crown moldings. An open floor plan includes a gourmet kitchen with Carrera marble island, top-of-the-line appliances, and white cabinets with glass accents. The living room is anchored by a fieldstone fireplace with a driftwood mantle. French doors lead to a radiant-heated screened porch, with it's own wbfp, ideal for seamless indoor-outdoor entertaining. The main floor master suite offers expansive walk-in closets and a marble bathroom. Upstairs, find four en-suite bedrooms, a bunk room, and a den. The lower level boasts a theater and a glass-enclosed gym. This property efficiently combines high-performance blow-in insulation with a dual water system, utilizing well water for a comprehensive 16-zone irrigation and municipal water for safe, in-home use.Outdoors, enjoy a 20x40 heated salt water gunite pool with a waterfall jacuzzi, surrounded by a 1500' bluestone patio, an outdoor fire pit, and pergola. This property also features a lush lawn, basketball/pickleball court, and proximity to Peconic Bay, beaches, and local wineries. Experience unparalleled luxury in this exquisite Southold home.

**Luxurious Coastal Retreat in Southold's Prestigious Deer Run** Nestled on a private, nearly 2-acre lot within the exclusive Deer Run community, this remarkable 5-bedroom, 9-bathroom cedar shake home epitomizes coastal luxury and refined living. Spanning an impressive 6,000 square feet and surrounded by 37 acres of preserved land, this home is a haven of grandeur and comfort. Its thoughtful design features transom windows, coffered ceilings, paneled walls, and crown moldings. An open floor plan includes a gourmet kitchen with Carrera marble island, top-of-the-line appliances, and white cabinets with glass accents. The living room is anchored by a fieldstone fireplace with a driftwood mantle. French doors lead to a radiant-heated screened porch, with it's own wbfp, ideal for seamless indoor-outdoor entertaining. The main floor master suite offers expansive walk-in closets and a marble bathroom. Upstairs, find four en-suite bedrooms, a bunk room, and a den. The lower level boasts a theater and a glass-enclosed gym. This property efficiently combines high-performance blow-in insulation with a dual water system, utilizing well water for a comprehensive 16-zone irrigation and municipal water for safe, in-home use.Outdoors, enjoy a 20x40 heated salt water gunite pool with a waterfall jacuzzi, surrounded by a 1500' bluestone patio, an outdoor fire pit, and pergola. This property also features a lush lawn, basketball/pickleball court, and proximity to Peconic Bay, beaches, and local wineries. Experience unparalleled luxury in this exquisite Southold home.

Your Going to Flip Over This Location! Nestled In The Goose Bay Estate With Beautiful Views of Goose Bay. This Adorable Cottage Is Just Waiting for You To Make It Your Own Dream Come True. Imagine Spending Time on The Front Deck Overlooking the Bay as The Sun Sets. Don't Miss Out On This Once in A Lifetime Opportunity!

Your Going to Flip Over This Location! Nestled In The Goose Bay Estate With Beautiful Views of Goose Bay. This Adorable Cottage Is Just Waiting for You To Make It Your Own Dream Come True. Imagine Spending Time on The Front Deck Overlooking the Bay as The Sun Sets. Don't Miss Out On This Once in A Lifetime Opportunity!

This charming ranch-style home offers a picturesque setting at the end of Ruch Lane, boasting water views of Hashamomuck Pond. Situated on a generous half-acre lot, the property presents an ideal canvas for single-story living or potential renovation and expansion opportunities. Approved Southold Town building permit in place for a stunning five-bedroom, 4.5-bath residence complete with a pool and detached garage. Plans are available for review at showings. Scaled-back expansion utilizing the oversized two-car garage and full basement offers another avenue for customization, providing flexibility to tailor the property to suit specific needs and preferences. Just minutes from Southold Hamlet and Greenport village and a quarter mile deeded sound beach access.

This charming ranch-style home offers a picturesque setting at the end of Ruch Lane, boasting water views of Hashamomuck Pond. Situated on a generous half-acre lot, the property presents an ideal canvas for single-story living or potential renovation and expansion opportunities. Approved Southold Town building permit in place for a stunning five-bedroom, 4.5-bath residence complete with a pool and detached garage. Plans are available for review at showings. Scaled-back expansion utilizing the oversized two-car garage and full basement offers another avenue for customization, providing flexibility to tailor the property to suit specific needs and preferences. Just minutes from Southold Hamlet and Greenport village and a quarter mile deeded sound beach access.

Southold--Reydon Shores--Beautiful, charming, farmhouse invites you in. 3-bedroom, 2.5 bath home in sought after community of Reydon Shores with easy access to the Association Bay beach and Marina. First floor large primary en-suite bedroom, chef's kitchen with top shelf stainless appliances including a Thermador cooktop and double oven. Radiant heat in Primary Bath and Kitchen. Closets beyond belief and hardwood floors throughout. Light, bright, and spacious with good flow. The kitchen opens to a great room and dining area Additional living space with a cozy wood burning fireplace. Upstairs-- two oversized guest bedrooms with hall bath and loft area. Immaculately updated and maintained, move-in ready. Doors open to the outdoor space including a large patio, trex deck, 2-car detached garage, and barn offering endless opportunities--workshop, studio, garden work area--let your imagination lead you. Level, landscaped shy half acre property. A perfect North Fork home waiting for you.

Southold--Reydon Shores--Beautiful, charming, farmhouse invites you in. 3-bedroom, 2.5 bath home in sought after community of Reydon Shores with easy access to the Association Bay beach and Marina. First floor large primary en-suite bedroom, chef's kitchen with top shelf stainless appliances including a Thermador cooktop and double oven. Radiant heat in Primary Bath and Kitchen. Closets beyond belief and hardwood floors throughout. Light, bright, and spacious with good flow. The kitchen opens to a great room and dining area Additional living space with a cozy wood burning fireplace. Upstairs-- two oversized guest bedrooms with hall bath and loft area. Immaculately updated and maintained, move-in ready. Doors open to the outdoor space including a large patio, trex deck, 2-car detached garage, and barn offering endless opportunities--workshop, studio, garden work area--let your imagination lead you. Level, landscaped shy half acre property. A perfect North Fork home waiting for you.

Exquisite waterfront home with wrap around porches and breathtaking views. Perfectly situated on the protected water way of Arshomomaque, where you can enjoy fishing, crabbing, clamming, boating, or just relax and listen to the birds. The first floor has a dining room, living room with a stone fireplace, den, laundry room, water side all-season room and a beautifully renovated eat in kitchen. The second floor has a master ensuite, 3 nice size bedrooms and an office. Their is plenty of room for storage in the detached garage or in the full size clean basement. Centrally located between Southold and Greenport villages, this home is also with-in the Southold Park District offering Founders and South Harbor Beach access.

Exquisite waterfront home with wrap around porches and breathtaking views. Perfectly situated on the protected water way of Arshomomaque, where you can enjoy fishing, crabbing, clamming, boating, or just relax and listen to the birds. The first floor has a dining room, living room with a stone fireplace, den, laundry room, water side all-season room and a beautifully renovated eat in kitchen. The second floor has a master ensuite, 3 nice size bedrooms and an office. Their is plenty of room for storage in the detached garage or in the full size clean basement. Centrally located between Southold and Greenport villages, this home is also with-in the Southold Park District offering Founders and South Harbor Beach access.

Come and explore the charm of cul de sac living on the serene North Fork! This expansive colonial home offers approximately 3200 square feet of living space nestled on nearly an acre of land. Step inside to discover a wealth of features designed to enhance your lifestyle. Recently updated bathrooms are adorned with radiant heated floors, providing a touch of luxury and comfort. With ample bedrooms, there's plenty of room for everyone to spread out and unwind. Additionally, an extra living space awaits, perfect for a home office or artist studio, allowing you to pursue your passions right from the comfort of home. The proximity to the Long Island Sound means you're just moments away from enjoying the beach life. Alternatively, if you prefer to stay closer to home, the in-ground pool offers a refreshing oasis right in your backyard, providing the best of both worlds. Don't miss out on the opportunity to make this exceptional property your own. Schedule a tour today and experience the beauty and tranquility of North Fork living for yourself!

Come and explore the charm of cul de sac living on the serene North Fork! This expansive colonial home offers approximately 3200 square feet of living space nestled on nearly an acre of land. Step inside to discover a wealth of features designed to enhance your lifestyle. Recently updated bathrooms are adorned with radiant heated floors, providing a touch of luxury and comfort. With ample bedrooms, there's plenty of room for everyone to spread out and unwind. Additionally, an extra living space awaits, perfect for a home office or artist studio, allowing you to pursue your passions right from the comfort of home. The proximity to the Long Island Sound means you're just moments away from enjoying the beach life. Alternatively, if you prefer to stay closer to home, the in-ground pool offers a refreshing oasis right in your backyard, providing the best of both worlds. Don't miss out on the opportunity to make this exceptional property your own. Schedule a tour today and experience the beauty and tranquility of North Fork living for yourself!

Absolutely flawless! Recently renovated throughout, this house showcases exquisite hardwood flooring, a stone fireplace, vaulted ceilings, newly appointed stone bathrooms, and a chef's kitchen with island open to the outdoor area. Outdoor entertaining is a dream with an oversized bluestone patio featuring a summer kitchen equipped with a gas grill, a cozy fire pit, and a deluxe hot tub nestled within a charming wooden platform. The meticulously landscaped gardens with an array of specimen trees, lush plants, and an abundance of vibrant flowers complete this offering. Conveniently located with convenient access to Southold Village, local vineyards, and farm stands this home offers

Absolutely flawless! Recently renovated throughout, this house showcases exquisite hardwood flooring, a stone fireplace, vaulted ceilings, newly appointed stone bathrooms, and a chef's kitchen with island open to the outdoor area. Outdoor entertaining is a dream with an oversized bluestone patio featuring a summer kitchen equipped with a gas grill, a cozy fire pit, and a deluxe hot tub nestled within a charming wooden platform. The meticulously landscaped gardens with an array of specimen trees, lush plants, and an abundance of vibrant flowers complete this offering. Conveniently located with convenient access to Southold Village, local vineyards, and farm stands this home offers

Meticulously restored and maintained 19th C Italianate style residence, beautifully set on elevated 1.25-acre lot. Built around 1850 by Silas Horton and occupied by his descendants until the 1960's. original wrap around porch, 17.5' floor to ceiling windows, ornate Cupula, marble fireplace mantles, original wide floorboards, in-tact period moldings, trims, banisters, and doors. Large, updated kitchen and baths, wood burning fireplace, large walk-up attic. Rarely does a house of this vintage and quality become available.

Meticulously restored and maintained 19th C Italianate style residence, beautifully set on elevated 1.25-acre lot. Built around 1850 by Silas Horton and occupied by his descendants until the 1960's. original wrap around porch, 17.5' floor to ceiling windows, ornate Cupula, marble fireplace mantles, original wide floorboards, in-tact period moldings, trims, banisters, and doors. Large, updated kitchen and baths, wood burning fireplace, large walk-up attic. Rarely does a house of this vintage and quality become available.

This property is a treasure trove of possibilities, boasting 2.7 acres of land, a spacious 3280 square foot home, and a substantial 2600 square foot barn. The main residence features an accessory apartment with a functioning bed and breakfast license. The barn presents further income potential, with five stalls or the space can be converted into an accessory living area. This property can also be an extraordinary family compound, featuring ample living spaces perfect for creating cherished memories. A heated saltwater pool, complete with electric cover, beckons relaxation and fun-filled moments, while solar panels underscore the commitment to sustainable living. Outdoor amenities abound, including an outdoor shower, a cozy fire pit for gathering under the stars, and vast expanses of land to explore and enjoy.Garden enthusiasts will be delighted by the fully irrigated vegetable gardens and flourishing orchard, adding to the property's allure and self-sufficiency. Offering far more than the ordinary, this property is available at an unbeatable price, presenting a rare opportunity in today's market.

This property is a treasure trove of possibilities, boasting 2.7 acres of land, a spacious 3280 square foot home, and a substantial 2600 square foot barn. The main residence features an accessory apartment with a functioning bed and breakfast license. The barn presents further income potential, with five stalls or the space can be converted into an accessory living area. This property can also be an extraordinary family compound, featuring ample living spaces perfect for creating cherished memories. A heated saltwater pool, complete with electric cover, beckons relaxation and fun-filled moments, while solar panels underscore the commitment to sustainable living. Outdoor amenities abound, including an outdoor shower, a cozy fire pit for gathering under the stars, and vast expanses of land to explore and enjoy.Garden enthusiasts will be delighted by the fully irrigated vegetable gardens and flourishing orchard, adding to the property's allure and self-sufficiency. Offering far more than the ordinary, this property is available at an unbeatable price, presenting a rare opportunity in today's market.

BEACH MEET BARN "Two Worlds Collide" in this breathtaking modern barn, nestled on 1.9 pastoral acres just a stone's throw from Duney, ocean-like Kenneys Beach, Sunsets and renowned Seaside Restaurant. This stunning residence features approximately 4700 sq ft of living space, a 4-car garage, separate service entrance, butler's station, a substantial light-filled kitchen, pantry room, and a great room with soaring ceilings, remote-controlled double-sided fireplace, Smart lighting controls at 8 locations for interior and exterior lighting, Sonos AV system - 8 speakers - 4 interior 4 exterior. The first floor includes a powder room, laundry room and a primary bedroom ensuite wing, complete with a naturally lit sitting area/office that opens directly onto a porch clad in "Blue Ice" and a 20'x40' "Black Onyx" pool with "Blue Ice" coping. The upper level offers a sizable loft that overlooks the great room, plus three additional bedrooms: one ensuite and two with separate wash areas leading to a shared bathing and privy room. There's also a powder room and a secondary laundry area. Completing this extraordinary home is an approximately 1000 sq ft artist studio/craft or game room. This stunning Estate is a must-have for the selective purchaser seeking "THE BEST of BOTH WORLDS"!

BEACH MEET BARN "Two Worlds Collide" in this breathtaking modern barn, nestled on 1.9 pastoral acres just a stone's throw from Duney, ocean-like Kenneys Beach, Sunsets and renowned Seaside Restaurant. This stunning residence features approximately 4700 sq ft of living space, a 4-car garage, separate service entrance, butler's station, a substantial light-filled kitchen, pantry room, and a great room with soaring ceilings, remote-controlled double-sided fireplace, Smart lighting controls at 8 locations for interior and exterior lighting, Sonos AV system - 8 speakers - 4 interior 4 exterior. The first floor includes a powder room, laundry room and a primary bedroom ensuite wing, complete with a naturally lit sitting area/office that opens directly onto a porch clad in "Blue Ice" and a 20'x40' "Black Onyx" pool with "Blue Ice" coping. The upper level offers a sizable loft that overlooks the great room, plus three additional bedrooms: one ensuite and two with separate wash areas leading to a shared bathing and privy room. There's also a powder room and a secondary laundry area. Completing this extraordinary home is an approximately 1000 sq ft artist studio/craft or game room. This stunning Estate is a must-have for the selective purchaser seeking "THE BEST of BOTH WORLDS"!

Welcome to your dream beach home nestled in a serene beach community on the North Fork! This newly constructed residence offers the perfect blend of modern comfort and coastal charm, presenting an ideal sanctuary for those seeking the quintessential beach lifestyle. Upon entering, you'll be greeted by an inviting open floor plan, seamlessly connecting the living, dining, and kitchen areas, creating a spacious and airy ambiance perfect for both relaxing and entertaining. The main floor boasts a convenient mudroom/laundry area, providing easy access for one-level living convenience. With four bedrooms, with three of the bedrooms featuring its own attached bathroom, including one on the main floor, this home offers unparalleled comfort and privacy for all occupants. Whether hosting guests or enjoying personal retreats, everyone will appreciate the luxury and convenience of ensuite facilities. Step outside onto the covered porch, where summer dining awaits amidst the gentle sea breezes and tranquil views of the preserved land beyond the backyard. The fenced backyard, featuring a sparkling pool for refreshing dips on hot days and outdoor seating surrounding a cozy fire pit, ideal for gathering under the stars on summerl evenings. The sandy beach community adds to the allure, offering a park area complete with picnic tables, panoramic views of the water, and access to a sandy beach where summer breezes beckon for leisurely strolls along the shoreline. This property presents a rare opportunity to experience the best of North Fork beach living. Whether you're seeking a seasonal retreat or year-round residence, this home promises a lifestyle of comfort, convenience, and coastal charm. Don't miss your chance to make memories and create your own slice of paradise in this idyllic seaside haven.