$1,500,000
●
House -
Off Market
661 Middle Road
Islip, NY 11705
7 Beds
3 Baths,
2
Half Baths
5,600 Ft²
$10,047
Est. Monthly
5.04%
Cap Rate
About This Property
Towering Pines – A Rare South Bayport Estate
Step beyond the wrought-iron gates and into Towering Pines, a remarkable 1860 Queen Anne Victorian where timeless architecture meets a storybook setting. Perfectly situated in South Bayport, this distinguished residence unfolds across lush, professionally landscaped grounds reminiscent of a private arboretum, where mature specimen trees, vibrant gardens, and curated pathways create an atmosphere of serenity and grace.The property's exterior is a sanctuary of outdoor living-featuring a tranquil koi pond with waterfall, an in ground pool surrounded by flowering gardens, a pergola-covered fire pit area, a child's play space, a covered hot tub, and a dedicated dog run. A circular driveway with a central fountain, porte-cochere, and motor court lead to a detached three-car garage crowned by an inviting bonus loft, ideal for studio use, or private retreat. The home's wraparound porch-one of its most defining features-welcomes you to a residence where craftsmanship and character reign supreme. Through double doors, the grand oak-paneled foyer sets the tone for what's within: hand-carved woodwork, coffered ceilings, crystal sconces, and built-in seating that speaks to the home's heritage and grace. Flanked by a formal living room and dining room, each with its own fireplace, this level showcases extraordinary architectural detail. The living room's curved windows open fully to the porch, while the dining room's raised panel walls and French doors connect seamlessly to the solarium and garden beyond. The handsome study, with its built-in granite-topped desk and intricate millwork, offers the perfect space for working from home in style. The kitchen is a blend of form and function, offering custom cabinetry, granite surfaces, and chef-caliber appliances, flowing effortlessly into an impressive lounge with wine bar and window seating, plus dining area, creating a seamless space for entertaining and everyday living. A cathedral-ceilinged great room with skylights invites gatherings both grand and intimate. Two powder rooms, a laundry room, and a heated enclosed porch complete the first level. Ascend the grand staircase-or the charming butler's stairs-to discover the second floor, where framed original blueprints line the walls beneath stained glass windows said to be authentic Tiffany. The primary suite features a marble-clad bathroom with soaking tub and walk-in shower, as well as a bespoke dressing room with custom closets. A junior suite, currently enjoyed as a library, includes built-in shelving, a fireplace, and access to a private balcony and full bath with original soaking tub. Two additional bedrooms each offer their own distinctive whimsical personality and comfort. The third level continues the home's story with three additional bedrooms-one presently used as a sitting room, another as an office-and a full bath with charming tub. Every inch of Whispering Pines reflects enduring craftsmanship: curved glass windows, custom millwork, porches and balconies that invite quiet moments, and modern amenities including central air, gas heat, and an interior/exterior sound system.
Towering Pines is more than a home-it's a living piece of South Bayport's history, gracefully blending old-world artistry with modern comfort. A rare opportunity to own one of the area's most enchanting and storied estates.
Step beyond the wrought-iron gates and into Towering Pines, a remarkable 1860 Queen Anne Victorian where timeless architecture meets a storybook setting. Perfectly situated in South Bayport, this distinguished residence unfolds across lush, professionally landscaped grounds reminiscent of a private arboretum, where mature specimen trees, vibrant gardens, and curated pathways create an atmosphere of serenity and grace.The property's exterior is a sanctuary of outdoor living-featuring a tranquil koi pond with waterfall, an in ground pool surrounded by flowering gardens, a pergola-covered fire pit area, a child's play space, a covered hot tub, and a dedicated dog run. A circular driveway with a central fountain, porte-cochere, and motor court lead to a detached three-car garage crowned by an inviting bonus loft, ideal for studio use, or private retreat. The home's wraparound porch-one of its most defining features-welcomes you to a residence where craftsmanship and character reign supreme. Through double doors, the grand oak-paneled foyer sets the tone for what's within: hand-carved woodwork, coffered ceilings, crystal sconces, and built-in seating that speaks to the home's heritage and grace. Flanked by a formal living room and dining room, each with its own fireplace, this level showcases extraordinary architectural detail. The living room's curved windows open fully to the porch, while the dining room's raised panel walls and French doors connect seamlessly to the solarium and garden beyond. The handsome study, with its built-in granite-topped desk and intricate millwork, offers the perfect space for working from home in style. The kitchen is a blend of form and function, offering custom cabinetry, granite surfaces, and chef-caliber appliances, flowing effortlessly into an impressive lounge with wine bar and window seating, plus dining area, creating a seamless space for entertaining and everyday living. A cathedral-ceilinged great room with skylights invites gatherings both grand and intimate. Two powder rooms, a laundry room, and a heated enclosed porch complete the first level. Ascend the grand staircase-or the charming butler's stairs-to discover the second floor, where framed original blueprints line the walls beneath stained glass windows said to be authentic Tiffany. The primary suite features a marble-clad bathroom with soaking tub and walk-in shower, as well as a bespoke dressing room with custom closets. A junior suite, currently enjoyed as a library, includes built-in shelving, a fireplace, and access to a private balcony and full bath with original soaking tub. Two additional bedrooms each offer their own distinctive whimsical personality and comfort. The third level continues the home's story with three additional bedrooms-one presently used as a sitting room, another as an office-and a full bath with charming tub. Every inch of Whispering Pines reflects enduring craftsmanship: curved glass windows, custom millwork, porches and balconies that invite quiet moments, and modern amenities including central air, gas heat, and an interior/exterior sound system.
Towering Pines is more than a home-it's a living piece of South Bayport's history, gracefully blending old-world artistry with modern comfort. A rare opportunity to own one of the area's most enchanting and storied estates.
Unit Size
5,600 Ft²
Days on Market
42 days
Land Size
1.70 acres
Price per sqft
$286
Property Type
House
Property Taxes
$2,195
HOA Dues
-
Year Built
-
Payment Calculator
Home Price
Down Payment
%
Loan Term
Interest %
Your Estimated Monthly Payment
Principal + Interest:
Property Tax:
HOA:
Home Insurance:
Mortgage Insurance:
Cap Rate Calculator
Purchase Price
Monthly Property Taxes
Monthly Rental Income
Maintenance & HOA
Income Per Year
Expenses Per Year
Operating Profit Per Year
Cap Rate
100% Occupancy
N/A (extreme outlier) What does this mean?
Based on our analysis, the cap rate of this property is 1.25%. A negative cap rate indicates that the property might not be feasible as an income-producing asset. The median cap rate for a near zip code 11238 is 4.23%.
How much can I actually make?
Actual monthly rental income may vary between $4,760 and $7,140 depending on unit-specific characteristics. You can change the amount using the slider to further explore.
How is cap rate calculated?
Cap Rate = Net Operating Income (NOI) / Property Asset Value.
When calculating the cap rate, we assume 100% occupancy. Leverage (mortgage) is not considered.
Cap Rate provided by RealtyHop and RentHop, learn more about cap rate here.
Last updated: 12 months ago (OneKey MLS #KEY919264)
Price History
| Date / Event | Date | Event | Price |
|---|---|---|---|
| Nov 17, 2025 | Sold | ||
| Sold | |||
| Oct 21, 2025 | In contract | - | |
| In contract | |||
| Oct 1, 2025 | No longer available | - | |
| No longer available | |||
| Oct 1, 2025 | Listed by Douglas Elliman Real Estate | $1,599,000 | |
| Listed by Douglas Elliman Real Estate | |||
| Jul 20, 2025 | Price Decreased |
$1,675,000
↓ $50K
(2.9%) | |
| Price Decreased | |||
Show More
Property Highlights
Garage
Parking Available
Air Conditioning
Fireplace
Building Info
Data used for valuation calculations is provided by RealtyHop, and other third party sources
Your Privacy Choices
Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017