Newly built and beautifully enhanced with approx. $300K in upgrades since purchase, 1665 Glenn Road offers a turnkey North Fork retreat with thoughtful upgrades, elevated finishes, and exceptional indoor-outdoor living. Set on a .52-acre lot in Southold, this 4-bedroom, 4.5-bath home spans approximately 3,248 square feet and features a desirable layout with a first-floor ensuite primary bedroom and three second-floor ensuite guest rooms. The interior is designed for both comfort and entertaining, with a two-sided gas fireplace, quartz kitchen countertops, Bosch and XO appliances, dimmer lighting throughout, electric shades in key living areas, ceiling fans in all bedrooms, and a first-floor laundry room. Home includes 7 built-in TVs, a 98-inch Sony screen and home theater with blackout shades, creating an impressive entertainment space. Since purchasing, the owner has elevated the property, including full front and rear landscaping, new lawns, extensive plantings, 73 trees, a new front walkway and steps, a rear sprinkler system, outdoor accent lighting, and a limestone patio surrounding the pool. The exterior is anchored by an 18x36 gated heated saltwater pool with a 500-gallon inground propane tank for the pool heater, a rear porch, dog run, retaining wall, and roof deck with water views. Additional features include a Sonos music system inside and out, alarm system, 2-car attached garage with shelving, additional refrigerator, and electric car hookup. Ideally located in Southold, this move-in-ready home combines new construction ease with substantial post-purchase improvements already completed.
For sale
Price cut: $100K (6/24)
$2,250,000
1665 Glenn Rd, Southold, NY 11971
4beds
3,248sqft
Single Family Residence
Built in 2024
0.52 Acres Lot
$2,299,700 Zestimate®
$693/sqft
$-- HOA
What's special
Two-sided gas fireplaceRear porchOutdoor accent lightingAdditional refrigeratorElectric car hookupDimmer lighting throughoutDesirable layout
- 52 days |
- 789 |
- 50 |
Zillow last checked:
Listed by:
Douglas Elliman Real Estate 631-354-8100,
Kristy B. Naddell - Associate Real Estate Broker 631-905-8584
Source: Out East,MLS#: 395185
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Rooms
- Room types: Family Room, Laundry, Office
Cooling
- Central Air
Features
- Basement: Yes
- Has fireplace: Yes
Interior area
- Total structure area: 3,248
- Total interior livable area: 3,248 sqft
Video & virtual tour
Property
Parking
- Parking features: None
Features
- Stories: 2
- Has private pool: Yes
- Pool features: Heated
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
Lot
- Size: 0.52 Acres
Details
- Parcel number: 1000078000100025000
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Condition
- New construction: No
- Year built: 2024
Community & HOA
Location
- Region: Southold
Financial & listing details
- Price per square foot: $693/sqft
- Tax assessed value: $2,200,000
- Date on market: 5/6/2026
- Lease term: Contact For Details
Estimated market value
$2,299,700
$2.18M - $2.41M
$7,303/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/24/2026 | Price change | $2,250,000-4.3%$693/sqft |
Source: | ||
| 5/6/2026 | Price change | $2,350,000-1.9%$724/sqft |
Source: | ||
| 12/2/2025 | Price change | $2,395,000-9.6%$737/sqft |
Source: | ||
| 6/23/2025 | Listed for sale | $2,650,000+17.1%$816/sqft |
Source: | ||
| 1/16/2025 | Sold | $2,262,500$697/sqft |
Source: Public Record Report a problem | ||
| 10/30/2024 | Sold | $2,262,500-1.4%$697/sqft |
Source: | ||
| 10/4/2024 | Pending sale | $2,295,000$707/sqft |
Source: | ||
| 8/28/2024 | Listed for sale | $2,295,000+337.1%$707/sqft |
Source: | ||
| 4/25/2024 | Sold | $525,000$162/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $12,100 +1412.5% |
| 2024 | -- | $800 |
| 2023 | -- | $800 |
| 2022 | -- | $800 |
| 2021 | -- | $800 |
| 2020 | -- | $800 |
| 2019 | -- | $800 |
| 2018 | -- | $800 |
| 2017 | $1,077 | $800 |
| 2016 | -- | $800 |
| 2015 | -- | $800 |
| 2014 | -- | $800 |
| 2013 | -- | $800 |
| 2012 | -- | $800 |
| 2011 | -- | $800 |
| 2010 | -- | $800 |
| 2009 | -- | $800 |
| 2008 | -- | $800 |
| 2007 | $816 +18.9% | $800 |
| 2005 | $687 +4.6% | $800 |
| 2004 | $657 +3.9% | $800 |
| 2003 | $632 +4.5% | $800 |
| 2002 | $605 | $800 |
| 2001 | -- | $800 |
| 2000 | $522 | $800 |
Find assessor info on the county website
Monthly payment
Estimated monthly payment$1,822
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 11971
Nearby schools
GreatSchools rating
- 6/10Southold Elementary SchoolGrades: K-6Distance: 0.8 mi
- 5/10Southold Junior Senior High SchoolGrades: 7-12Distance: 0.8 mi
A local agent can set up tours, give advice and negotiate with sellers.
- New York
- Suffolk County
- Southold
- 11971
- 1665 Glenn Rd






