Rental Registration #: R-25-0020 Looking for a spacious rental in the village of Sag Harbor? Experience Sag Harbor Cove sunset views from this versatile village home and legal guest cottage filled with character and comfort. Situated on Main Street, just moments from the heart of Sag Harbor, this spacious home is convenient to shopping, restaurants and the Hampton Jitney. Inside the main house, a bright foyer opens to a classic double parlor living/dining room with bay windows, moldings, and original glass window panes-details that nod to the home's 1840 roots. This beautifully restored village gem combines classic charm with modern convenience. The spacious ground floor space is spectacularly decorated with all the modern comforts while maintaining its historical charm. Enjoy original fir floors, and large windows that flood the space with an amazing amount of natural light. There is a large living space, formal dining room, and large, fully equipped chefs' kitchen. French doors off the kitchen and dining area lead to a quaint covered patio insulated by potted evergreens. Two generously sized ground-floor bedrooms provide a perfect mix of elegance and serenity. The updated bathroom features modern fixtures while retaining a vintage feel, complete with a clawfoot tub/shower combo. Upstairs you'll find a modern 1-bedroom apartment that combines comfort and convenience. Enjoy an open-concept layout with large windows and French doors that bring in an abundance of natural light, creating a warm and welcoming atmosphere. There is spacious kitchen, dining area, and ample living room which leads to a private deck where you can grill, dine, and unwind and enjoy elevated living and panoramic views of Otter Pond. Architectural potted evergreen screening for enhanced privacy - grill, dine, and enjoy the warm light of golden hour. A bright and light bedroom and a full bathroom provides a peaceful haven for relaxation. A lovely, newly landscaped garden with brand new heated, saltwater pool offers a peaceful escape to enjoy your morning coffee or evening relaxation. Several seating areas and quiet nooks to find respite or soak in the sun. In the evening, enjoy quiet moments by the modern fire pit under the open sky and stars. A separate, legal one bedroom cottage with kitchenette and full bath sits at the rear of the property; a perfect place for guests or remote work. Off-street parking available. Don't miss the chance to call this piece of history your home! [[Rental Registration # R-25-0020]]
Sold for $2,200,000
$2,200,000
299 Main St, Sag Harbor, NY 11963
4beds
2,000sqft
MultiFamily
Built in 1840
-- sqft lot
$2,429,600 Zestimate®
$1,100/sqft
$5,192 Estimated rent
Home value
$2,429,600
$2.21M - $2.67M
$5,192/mo
Zestimate® history
Owner options
List your home for rent
$5,192/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$5,192/mo
Rent Zestimate®
Refinance and save
$15,237/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$15,237/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Newly landscaped gardenBright foyerSpacious ground floor spaceBay windowsOriginal glass window panesOriginal fir floorsFormal dining room
Zillow last checked:
Listing updated:
Source: Zillow Rentals
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Rooms
- Room types: Laundry Room
Cooling
- Central Air
Features
- View
- Has basement: Yes
Interior area
- Total interior livable area: 2,000 sqft
Property
Parking
- Parking features: None
- Details: Contact manager
Features
- Stories: 2
- Exterior features: Architecture Style: victorian, Broker Exclusive
- Pool features: Pool
- Has view: Yes
- View description: Water View
Lot
- Size: 8,712 Square Feet
Details
- Parcel number: 0903006000100005000
Construction
Type & style
- Home type: MultiFamily
- Property subtype: MultiFamily
Condition
- Year built: 1840
Community & HOA
Community
- Features: Pool
HOA
- Amenities included: Pool
Location
- Region: Sag Harbor
Financial & listing details
- Price per square foot: $1,100/sqft
- Tax assessed value: $1,022,300
- Date on market: 1/21/2026
- Lease term: Contact For Details
Price history
| Date | Event | Price |
|---|---|---|
| 5/16/2026 | Listing removed | $75,000$38/sqft |
Source: Zillow Rentals Report a problem | ||
| 1/21/2026 | Listed for rent | $75,000+36.4%$38/sqft |
Source: Zillow Rentals Report a problem | ||
| 9/2/2025 | Listing removed | $55,000$28/sqft |
Source: Zillow Rentals Report a problem | ||
| 4/25/2025 | Listed for rent | $55,000$28/sqft |
Source: Zillow Rentals Report a problem | ||
| 1/13/2025 | Sold | $2,200,000-13.7%$1,100/sqft |
Source: Public Record Report a problem | ||
| 7/19/2024 | Price change | $2,550,000-7.3%$1,275/sqft |
Source: Out East #377471 Report a problem | ||
| 4/18/2024 | Price change | $2,750,000-11.3%$1,375/sqft |
Source: Out East #377471 Report a problem | ||
| 3/7/2024 | Price change | $3,100,000-11.4%$1,550/sqft |
Source: Out East #377471 Report a problem | ||
| 12/8/2023 | Listed for sale | $3,500,000+251.8%$1,750/sqft |
Source: Out East #377471 Report a problem | ||
| 4/23/2004 | Sold | $995,000$498/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $1,022,300 |
| 2024 | -- | $1,022,300 |
| 2023 | -- | $1,022,300 |
| 2022 | -- | $1,022,300 |
| 2021 | -- | $1,022,300 |
| 2020 | -- | $1,022,300 |
| 2019 | -- | $1,022,300 +3.2% |
| 2018 | -- | $990,600 |
| 2017 | $5,908 | $990,600 |
| 2016 | -- | $990,600 |
| 2015 | -- | $990,600 |
| 2014 | -- | $990,600 |
| 2013 | -- | $990,600 |
| 2012 | -- | $990,600 |
| 2011 | -- | $990,600 +0.6% |
| 2007 | $4,973 -3.9% | $985,000 +25.4% |
| 2005 | $5,173 +6.1% | $785,366 +6462.2% |
| 2004 | $4,875 +8.4% | $11,968 |
| 2003 | $4,498 +10.4% | $11,968 |
| 2002 | $4,075 +7.5% | $11,968 |
| 2001 | $3,789 +8.7% | $11,968 |
| 2000 | $3,485 | $11,968 |
Find assessor info on the county website
Neighborhood: 11963
Nearby homes
- $3,934,7004 bd5 ba2k sqft295 Main St, Sag Harbor, NY 11963Off Market

- $654,700-- bd-- ba-- sqft303 Main St, Sag Harbor, NY 11963Off Market
- $2,200,0003 bd2 ba1.6k sqft291 Main St, Sag Harbor, NY 11963Sold

- $1,834,3002 bd1 ba1.4k sqft307 Main St, Sag Harbor, NY 11963Off Market
- $3,054,4004 bd4 ba2.7k sqft287 Main St, Sag Harbor, NY 11963Off Market
- $5,065,7004 bd6 ba3.4k sqft311 Main St, Sag Harbor, NY 11963Off Market
- $829,100-- bd-- ba1.2k sqft283 Main St, Sag Harbor, NY 11963Off Market
- $2,674,3003 bd2 ba1.6k sqft281 Main St, Sag Harbor, NY 11963Off Market
Nearby schools
GreatSchools rating
- 8/10Sag Harbor Elementary SchoolGrades: PK-5Distance: 0.6 mi
- 8/10Pierson Middle High SchoolGrades: 6-12Distance: 0.6 mi
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$2,429,600
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$2,429,600