SOUTHOLD, NY
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Southold

Southold, which was established 1640, has long been a delightful community and continues to evolve with its unspoiled beaches, sprawling vineyards and wineries, agricultural production and farm stands, historic buildings, museums and unlimited recreational opportunities. Its bucolic qualities, culture and history have made Southold a special place to be, and continues to thrive with its unique shopping opportunities and casual and fine dining fare.

Southold

Total Listings: 118
Average Price: $785,045
Highest Price: $2,995,000
Lowest Price: $160,000

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Southold Homes For Sale

118 Properties Found. Page 1 of 3
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Simply Exquisite Pristine Nantucket Style Water...

$2,995,000

19965 Soundview Ave, Southold

  • 3 Beds
  • 4 Baths
  • 0.72 Acres
  • 3,064 sqft

School District: Southold

Simply Exquisite Pristine Nantucket Style Waterfront Compound Adorns Bluffs Sitting High Above Li Sound. The Chic Main House With Gourmet Kitchen And Double Sided Fireplace And Separate Pool House Are Built Around The Common Outdoor Recreational Areas, Guni...

Spacious & Grand Waterfront Center Hall Colonia...

$2,399,999

105 Waterview Dr, Southold

  • 4 Beds
  • 3 Baths
  • 6.5 Acres
  • 5,000 sqft

School District: Southold

Spacious & Grand Waterfront Center Hall Colonial On 6.5 Acres With Dock Over-looking Goose Creek. Impeccably Designed With Attention To Every Detail. Featuring Custom Woodwork Throughout. Gourmet Kitchen With Custom Cabinets, Central Vacuum On All Floors, D...

28 Acres On North Bayview. Development Rights E...

REDUCED 15% Photo of Listing #2965814

$2,299,000

8360 N Bayview Rd, Southold

  • 28 Acres

School District: Southold

28 Acres On North Bayview. Development Rights Entact. Possible Sub-division With Approval. All Or Part Of Development Rights May Be Sold To A Variety Of Local Municipalities. Development Potential : Possible Use As An Estate, Horse Farm. Agricultural Friend...

Welcome To Paradise. Rare Southold Bayfront Sit...

$2,199,000

3525 Paradise Point Rd, Southold

  • 4 Beds
  • 3 Baths
  • 2.38 Acres

School District: Southold

Welcome To Paradise. Rare Southold Bayfront Situated On 2.3 Acres With 97 Feet Of Private Beach And Community Boating Rights. Take In Magnificent Water Views From The Custom Built 4 Bd., 3 Ba. Residence With 3 Levels Of Luxurious Living Featuring A Double-h...

Idyllic Waterfront Location With 3 Bedroom 3.5 ...

NEW Photo of Listing #3030495

$2,199,000

1700 Hyatt Rd, Southold

  • 5 Beds
  • 6 Baths
  • 1.06 Acres
  • 6,365 sqft

School District: Southold

Idyllic Waterfront Location With 3 Bedroom 3.5 Bath Main House And Legal 1539 Sf. 2 Bedroom 2 Bath Guest Apartment On Beautiful Long Island Sound. Unbelievable Views From Private 100' Sandy Beach Outside Your Back Door, Mere Steps Away. Direct Access To The...

Taxes Reduced!!! Spectacular North Fork Setting...

REDUCED 9%

$1,999,000

2704 Long Creek Dr, Southold

  • 4 Beds
  • 3 Baths
  • 7.8 Acres
  • 3,500 sqft

School District: Southold

Taxes Reduced!!! Spectacular North Fork Setting Of Over 18 Waterfront Acres! 3,000 Linear Feet Of Waterfront With Incredible Views. Lodge Style Home Designed For Entertaining Offers Pool And Tennis Plus Abandoned 'boat House' - An Ideal Compound - Privat...

18+ Waterfront Acres Developed W/house, Pool & ...

REDUCED 9% Photo of Listing #2869850

$1,999,000

2707 Long Creek Dr, Southold

  • 18.11 Acres

School District: Southold

18+ Waterfront Acres Developed W/house, Pool & Tennis Plus Old Boat House.. Wooded And Natural Setting - Ideal For Deveopment Potential Or Use As Estate, Etc. Taxes Grieved And Reduced! For 2018/19

Featured In Coastal Living Magazine, This Conte...

$1,800,000

1455 Cedar Point Dr, Southold

  • 3 Beds
  • 2 Baths
  • 0.47 Acres

School District: Southold

Featured In Coastal Living Magazine, This Contemporary Beach Cottage Overlooks The Peconic Bay, A Nature Preserve, And A Deep Water Inlet. 3 Bedrooms, 2 Baths, Open Concept, Including Living, Dining, Kitchen And An Entertainment Nook, Wood Burning Fireplace...

Move In Ready, Immaculate Soundfront Residence ...

$1,750,000

20575 Aka Soundview Ave, Southold

  • 4 Beds
  • 3 Baths
  • 0.75 Acres
  • 2,200 sqft

School District: Southold

Move In Ready, Immaculate Soundfront Residence W/private Beach And Fully Bulkheaded. Room For Pool. Spectacular Sunsets All Year Long... Large Living Room / Dinning Room W/waterside Terrace, Eik, Bath, Laundry And Master Suite W/bath Plus Bedroom On Prima...

Sound Front Property Located In The Coveted Tre...

REDUCED 6%

$1,699,000

18575 Soundview Ave, Southold

  • 3 Beds
  • 3 Baths
  • 1 Acres
  • 2,219 sqft

School District: Southold

Sound Front Property Located In The Coveted Tree-lined Mount Beulah Section With Over 150 Feet Of Beachfront, Views Of Li Sound & Sunsets W/steps To Private Beach. Lots Of Living Space Abounds Throughout Entire Home. 3 Bedrooms, 2.5 Bath, 2 Car Garage, Full...

Sensational Panoramic Water Views, Offering 142...

$1,499,000 Under Contract

2895 Wells Ave, Southold

  • 5 Beds
  • 3 Baths
  • 0.58 Acres

School District: Southold

Sensational Panoramic Water Views, Offering 142.5" On Jockey Creek, With Sandy Bay Beach And Direct Passage Out To Peconic Bay. Distinguished Within Its Class, This 5 Bed, 3 Bath Traditional Home, Possesses Endless & Rare Opportunity. A 35 X15 Boat House An...

Enjoy Sunsets And Forever Vineyard Views From T...

$1,495,000

1375 Ackerly Pond Ln, Southold

  • 4 Beds
  • 3 Baths
  • 10 Acres

School District: Southold

Enjoy Sunsets And Forever Vineyard Views From This Lovely 4 Bedroom 3 Bath Farmhouse Sitting On Over 10 Acres On A Lovely Street In Southold. This Farm Has It All, 8 Stalls In 2 Barns, Fully Irrigated 100' X 200' Arena, Irrigated Paddocks, 2 Tack Rooms, And...

Relaxation And Gracious Living Await At This Pe...

$1,375,000

1230 Kimberly Ln, Southold

  • 5 Beds
  • 3 Baths
  • 1.06 Acres
  • 4,477 sqft

School District: Southold

Relaxation And Gracious Living Await At This Perfectly Sited Home Set On 1.08 Acres. Enjoy Tranquil Bay Views And Breezes From Your Covered Front Porch. With Plenty Of Room For A Pool And A Large Deck For Entertaining, This Spacious Home Accommodates All. P...

Drive Down A Long Tree Lined Drive To This Cust...

$1,295,000

535 Lighthouse Rd, Southold

  • 4 Beds
  • 3 Baths
  • 5.38 Acres
  • 2,850 sqft

School District: Southold

Drive Down A Long Tree Lined Drive To This Custom Built 4 Br, 2.5 Bath Post Modern. Sited On 5+ Private Acres. Perfect For Horses, Vineyard Or Hops, The Choice Is Yours. Large Great Room With Stone F/p Opens Into A Gourmet Kitchen, Dbl Ovens, Granite Tops, ...

Location, Style, Privacy, Beach, Boating...this...

REDUCED 7%

$1,295,000

3735 Paradise Point Rd, Southold

  • 4 Beds
  • 4 Baths
  • 2.46 Acres
  • 2,500 sqft

School District: Southold

Location, Style, Privacy, Beach, Boating...this Property Has It All! Open Floor Plan With Plenty Of Natural Light To Highlight The Hardwood Floors And High Ceilings. Sprawling Entertaining Spaces Flow Outside To The Wood Deck Where You'll Enjoy Pond And...

5.7 Acres, Front 1 Plus Acres Are Zoned Hamlet ...

REDUCED 8%

$1,199,000

56995 Route 25, Southold

  • 5 Beds
  • 2 Baths
  • 5 Acres
  • 2,500 sqft

School District: Southold

5.7 Acres, Front 1 Plus Acres Are Zoned Hamlet Business And Back 4 Acres Are Zoned Agricultural. Perfect For A Gentleperson's Farmstead, B&b, Or Convert To Business Use (check Permitted Uses.) Also Subdivision Possibilities.. Two Large Barns And A Victoria...

Renovated Ranch With Spectacular Water Views, F...

$1,199,000

630 N Sea Dr, Southold

  • 3 Beds
  • 2 Baths
  • 0.9 Acres

School District: Southold

Renovated Ranch With Spectacular Water Views, Featuring Beautiful Granite Counter Tops, New Ss Appliances, 3 Bedroom, Master Suite With Bathroom And 2 Additional Bedrooms, Full Bath. Wrap Around Deck With Beautiful Sunsets.

A Rare Opportunity To Purchase A Home In Harbor...

$995,000

90 Windjammer Dr, Southold

  • 4 Beds
  • 3 Baths
  • 0.44 Acres
  • 3,000 sqft

School District: Southold

A Rare Opportunity To Purchase A Home In Harbor Lights, Boasting 4 Bedrooms Including 2 Waterview Master Suites, 1 On Each Floor. Large Eat In Kitchen, Open Floor Plan, In-ground Pool, On Shy 1/2 Acre. Enjoy Sandy Peconic Bay Beach, Park And Your Very Own ...

Great Location Set On A Country Rd! Can Drive U...

Photo of Listing #3014950

$995,000

1080 Ackerly Pond Rd, Southold

 

Great Location Set On A Country Rd! Can Drive Up To "building Envelope'. Build Your Dream House On 1.5 Acres. Surround Yourself With 22.4 Acres Of Privacy, Yet Has Great Visibility If Needed. Best Of Both Worlds. Development Rights Sold. Perfect Agricultura...

Waterfront End Unit! Expansive Creek And Bay Vi...

$949,000

Southold

  • 3 Beds
  • 4 Baths
  • 0.25 Acres

School District: Southold

Waterfront End Unit! Expansive Creek And Bay Views. The Cove Is A Gem, Hidden On The Southold Peninsula Most Desirable Unit In Complex This Spacious Home Has Recent Updates In Kitchen And 3 1/2 Baths. Bedrooms Have Custom Closets. Wood Flrs Throughout....

Waterfront End Unit. Superior Location Within ...

$949,000

755 Meadow Ct, Southold

  • 3 Beds
  • 4 Baths
  • 0.25 Acres

School District: Southold

Waterfront End Unit. Superior Location Within Complex Elegant, Spacious Unit, Loaded W/extras. Updated Bath(s) & Kitchen. Custom Ca Closets, He Heating And Cooling. Hardwood Flrs Throughout. Exercise Room W/steam Sauna, Tons Of Storage, New Electric De...

8.3 Acres With Development Rights Intact. Owner...

REDUCED 5% Photo of Listing #2525655

$899,000

57207 Route 25, Southold

  • 8.3 Acres

School District: Southold

8.3 Acres With Development Rights Intact. Owner Wishes To Sell W/ Adjacent Hamlet Business Zoned 3br House On Addt'l .56 Acres. Separate Parcels. Possible Subdivision Or Gentleman's Farm...many Usage Options...imagine The North Fork Possibilities This Purc...

Possibilities Abound - Hamlet Business Zoned Ho...

REDUCED 5%

$899,000

57555 Route 25, Southold

  • 3 Beds
  • 2 Baths
  • 0.56 Acres
  • 1,400 sqft

School District: Southold

Possibilities Abound - Hamlet Business Zoned House To Live In Or Rent Owner Wishes To Sell W/ Adjacent 8.3 Acre R-80 Vacant Land- Development Rights Intact. Retail, Rental, Gentleman's Farm Or Possible Sub-division. Zoning Allows For Many Opportunities.

Take Advantage Of A Wonderful Opportunity To De...

$899,000

1350 Hortons Ln, Southold

  • 4 Beds
  • 3 Baths
  • 2.07 Acres
  • 2,660 sqft

School District: Southold

Take Advantage Of A Wonderful Opportunity To Design Your Own Custom Built Escape On 2.24 Acrs On The North Fork. Modular Built Flexibility Gives You All The Design Influence You Desire With A Fraction Of The Time Investment Of Traditional Construction. Mu...

Southold North Fork Sunset Knolls Designer Home...

REDUCED 4%

$899,000

275 Aka330 Majors Path, Southold

  • 4 Beds
  • 3 Baths
  • 0.81 Acres
  • 2,000 sqft

School District: Southold

Southold North Fork Sunset Knolls Designer Home On Shy 1ac W/shared Ownership Of 1.4 Private Sound Front Acres W/242' Of Beach! Recent Construction Home Features Wrap Around Porch, Room For Pool And Peekaboo Waterviews. Den W/fp, Mbr Suite, 3 Additional Be...

Enjoy Exceptional Pride Of Ownership And Panora...

REDUCED 10%

$895,000

5805 Main Bayview Rd, Southold

  • 4 Beds
  • 3 Baths
  • 4.41 Acres
  • 3,000 sqft

School District: Southold

Enjoy Exceptional Pride Of Ownership And Panoramic Waterviews Across Your Own Four Acres Of Scenic Shorefront Property In This Well-built Traditional Home Featuring Large Rooms And Top-quality Construction. Membership Rights In Goose Neck Estates Associatio...

Be Prepared For Panoramic Water Views. The Geog...

$889,000 Under Contract

2155 Long Creek Dr, Southold

  • 4 Beds
  • 3 Baths
  • 0.95 Acres
  • 3,200 sqft

School District: Southold

Be Prepared For Panoramic Water Views. The Geography Of This Property Affords A View Of The Water From Every Room With Water Frontage On The North And West Property Lines. High And Dry. Main Floor Master And Large Open Floor Plan Make This A Modern Retrea...

Stunning Chalet-style Home, Impeccably Built An...

NEW

$879,000

14395 Main Bayview Rd, Southold

  • 3 Beds
  • 2 Baths
  • 2.18 Acres
  • 2,000 sqft

School District: Southold

Stunning Chalet-style Home, Impeccably Built And Maintained. Covered Porches Perfect For Outdoor Entertaining. Open Floor Plan, Kitchen/dining + Living With Soaring Stone Fireplace At Center Stage. 3 Bedrooms, 2 Baths Perfectly Situated On Over 2 Acres Of L...

Come Taste The Farm Country Lifestyle, A True N...

REDUCED 4%

$849,000

9785 Main Bayview Rd, Southold

  • 3 Beds
  • 3 Baths
  • 2.59 Acres

School District: Southold

Come Taste The Farm Country Lifestyle, A True North Fork Way Of Living. Salt Air Amidst The Surrounding Farms, This Home Is A True Rural Retreat. Modern Farmhouse, Covered Front Porch, Open Kitchen Den Combo With Formal Living & Dining Space. Setback 2.6...

2.6 Acres Of Secluded Land Setback From The Roa...

REDUCED 4% Photo of Listing #2988367

$849,000

Southold

  • 2.59 Acres

School District: Southold

2.6 Acres Of Secluded Land Setback From The Road. Your Own Private Sanctuary Just Outside Of Town And Moments From Some Of North Fork's Best Beaches. An Equestrian Or Winemakers Dream, Custom Craftsman Barn And Fenced In Backyard With Deck.

Priced Below Market Value! Classic Dutch Coloni...

$816,000

215 Garden Ct, Southold

  • 4 Beds
  • 3 Baths
  • 0.6 Acres
  • 2,800 sqft

School District: Southold

Priced Below Market Value! Classic Dutch Colonial Located On .6 Acre Landscaped Grounds With Inground Sprinker System. Oversized 2 Car Garage, 4 Bdrm, 3 Full Bath, Jacuzzi, Family Rm,fireplace,formal Dining, Huge Finished Basement. 20x40 Heated Pool, Priva...

Someone Is Going To Get A Great Deal! Beautiful...

REDUCED 4%

$799,000

435 Willow Pond Ln, Southold

  • 5 Beds
  • 4 Baths
  • 0.92 Acres
  • 2,700 sqft

School District: Southold

Someone Is Going To Get A Great Deal! Beautifully Constructed, With Interesting Architectural Details, A Chic And Sophisticated Home In The Heart Of Southold, Park-like Setting With Pool Permit In Place. A Well-equipped Chef's Kitchen, 1st And 2nd Floor En...

Standing Tall In Coveted Calves Neck A Custom B...

$799,000

800 Mid Farm Rd, Southold

  • 4 Beds
  • 4 Baths
  • 0.61 Acres
  • 3,000 sqft

School District: Southold

Standing Tall In Coveted Calves Neck A Custom Built Traditional Home On A Corner Property W/ Beautiful Trees & Mature Landscaping. Enjoy Your Morning Coffee In The Glow Of The Warm Light That Floods The Kitchen W/ Distant Views Of Jockey Creek. A Spacious H...

Water Front Living On The North Fork Of Long Is...

REDUCED 8%

$790,000

58235 Route 48, Southold

  • 3 Beds
  • 2 Baths
  • 0.12 Acres
  • 1,500 sqft

School District: Southold

Water Front Living On The North Fork Of Long Islands Wine Country Awaits You. Spacious 3 Bedroom, 2 Bath With Breath Taking Direct Views Of The Long Island Sound And Your Very Own Private Beach! Balconies Facing The Sound From Both The Living Room And Bed...

Charming North Fork Country Homestead Nestled I...

$775,000 Under Contract

385 Grissom Ln, Southold

  • 4 Beds
  • 4 Baths
  • 1 Acres
  • 3,500 sqft

School District: Southold

Charming North Fork Country Homestead Nestled Into Very Private Acre. Features Large Open Eat-in Kitchen, Wood Floors Thru-out, High Ceilings, Lots Of Natural Light. 4 Bedrooms, 2.5 Baths, Wood Burning Fireplace, Detached Oversized 2.5 Car Garage.

This Shy 2.5 Acre Property Is A Peaceful Place ...

Photo of Listing #2930917

$750,000 Under Contract

9502 N Bayview Rd, Southold

  • 2.44 Acres

School District: Southold

This Shy 2.5 Acre Property Is A Peaceful Place Near Paradise Point. The Property Has A Quality Home Well Under Construction With A Traditional Open Floor Plan With Finished Features Throughout. There Is A Barn And Corral In Place For A Horse Owners Dream....

This Shy 2.5 Acre Property Is A Peaceful Place ...

$750,000 Under Contract

9502 N Bayview Rd, Southold

  • 3 Beds
  • 3 Baths
  • 2.44 Acres

School District: Southold

This Shy 2.5 Acre Property Is A Peaceful Place Near Paradise Point. The Property Has A Quality Home Well Under Construction With A Traditional Open Floor Plan With Finished Features Throughout. There Is A Barn And Corral In Place For A Horse Owners Dream. ...

Beautiful 1.27 Ac. Building Lot Overlooking Dev...

Photo of Listing #2995724

$750,000

4402-4&5 Old North Rd, Southold

  • 8.59 Acres

School District: Southold

Beautiful 1.27 Ac. Building Lot Overlooking Development Rights Sold Farmland Preserving Your Sunsets Forever. Flat And Level, This Homesite Is Ready To Be Built Upon And Sits Near To An Historic 1820's Farmhouse With All The Charm Of The North Fork. Include...

Price Overhaul. Nestled On Long Creek Drive Sou...

$749,999

1345 Long Creek Dr, Southold

  • 4 Beds
  • 2 Baths
  • 0.53 Acres
  • 1,509 sqft

School District: Southold

Price Overhaul. Nestled On Long Creek Drive Southold. Generously Proportioned Rooms. Sunken Livingroom With Fireplace. Waterside Deck Overlooking Creek. Full Basement, Two Car Garage. Bring Your Vision To Update This Solid Waterfront Home. Member Of Southol...

Immaculate Discerning Only The Very Best For Th...

$749,000

80 Wild Cherry Way, Southold

  • 4 Beds
  • 3 Baths
  • 0.62 Acres

School District: Southold

Immaculate Discerning Only The Very Best For This No Stone Unturned Home. Palatial Grounds, Room For A Fabulous Pool. Close To Greenport And Southold Town Shopping, Yet Protected And Serene Area.beautiful Atlantic Pine Trees Flanking Your West And On Each S...

Immaculate Four Bedroom Home In Southold Garden...

$749,000

1290 Hill Rd, Southold

  • 4 Beds
  • 3 Baths
  • 2,500 sqft

School District: Southold

Immaculate Four Bedroom Home In Southold Gardens On Calves Neck. Private And Secluded Backyard In Quiet Community. Open Floor Plan, Master Bedroom Suite On Ground Floor. Close Proximity To Southold Village Restaurants, Pharmacy, Hampton Jitney Stop, Sho...

Weekend Getaway With Water Views Of Long Island...

REDUCED 5%

$748,500

1895 Leeton Dr, Southold

  • 3 Beds
  • 2 Baths
  • 0.5 Acres

School District: Southold

Weekend Getaway With Water Views Of Long Island Sound, 3 Bdr 2 Full Bath Exp Cape,eik, Great Room,hdw Pine Wood Flooring Thru Out,sets Of Sliding Glass Doors To Wraparound Deck, 2nd Floor Deck, 2 Skylights,out Door Shower, Enjoy The Beautifull Sunsets And M...

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