3 CHESTER AVENUE
About This Property
From the moment you enter, natural light pours through every window, illuminating three levels of thoughtfully designed living space. Classic details - arched doorways, hardwood floors, custom built-ins, and rich millwork - blend seamlessly with modern updates, creating a home that feels both timeless and fresh.
The inviting floor plan offers room for every occasion. A serene primary suite with its own fireplace provides a private retreat, while the main-level office doubles as a guest room or den. Formal living room with fireplace and gorgeous dining room set the stage for elegant entertaining The family room invites casual gatherings with another fireflace and access to the screened porch. The updated kitchen is a true centerpiece, with fresh cabinetry, stylish countertops, and a backsplash that ties it all together.
Upstairs, a spiral staircase leads to a sunlit loft with a private balcony - perfect for a creative nook, playroom, or quiet reading space. Outside, the screened porch, fenced yard, and welcoming front porch create effortless indoor-outdoor living, ideal for relaxing or hosting friends.
The basement was recently waterproofed. Practical touches like a mudroom with laundry and off-street parking make everyday life easy.
Beyond the walls, Eastport beckons. Launch your kayak from Horn Point Park, wander streets lined with art and history, or cross the Spa Creek drawbridge to downtown Annapolis and the Naval Academy. From this location, the Chesapeake Bay is your playground - with cruising and fishing destinations like Baltimore's Inner Harbor, St. Michael's, Oxford, and Solomon's Island all within reach.
Annapolis offers the perfect balance of small-town charm and cosmopolitan sophistication, and this Eastport jewel places you right at the center of it all. With quick access to Rt. 50 and 97, Baltimore, BWI, Ft. Meade/NSA, and Washington, DC are just a drive away.
This is more than a home - it's a lifestyle. Welcome to Eastport.
Payment Calculator
Your Estimated Monthly Payment
Cap Rate Calculator
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.
Price History
| Date / Event | Date | Event | Price |
|---|---|---|---|
| Feb 12, 2026 | Sold | ||
| Sold | |||
| Jan 14, 2026 | In contract | - | |
| In contract | |||
| Jan 2, 2026 | Price Decreased |
$1,680,000
↓ $50K
(2.9%) | |
| Price Decreased | |||
| Nov 22, 2025 | Listed by Keller Williams Select Realtors of Annapolis | $1,730,000 | |
| Listed by Keller Williams Select Realtors of Annapolis | |||
| Aug 8, 2025 | Sold | ||
| Sold | |||
Property Highlights
Building Info
Comparables
Status
Price/ft²
Listed On
Sold On
Phone: 425-283-2930
Address: 335 Madison Avenue, New York, NY 10017