About 109 Hillside Avenue
The best water views in Milford! Designed by award-winning, Yale-trained architect Ray Oliver, this custom coastal home offers 5 bedrooms, sweeping water views from almost every room, abundant natural light and the beauty and tranquility of this special, private setting. Upon arrival, you are welcomed by mature, low-maintenance perennial gardens and the soothing sounds of the fountain. A dramatic wall of windows frames the Long Island Sound from the main living area, while French doors open to an expansive waterfront deck-perfect for dining, entertaining or watching the boats, changing tides, sunrises and sunsets. High ceilings, a beautiful stained-glass window and three marble baths add architectural character. The thoughtfully designed layout offers multiple gathering spaces and features abundant closets and storage, a walk-in pantry and beautifully updated chef's kitchen. A serene second floor book nook and primary bedroom suite with 6-foot Jacuzzi tub and stunning views, offer peaceful retreats. 2 additional bedrooms, a full bath and laundry complete the second floor. The third floor offers 2 more bedrooms with walk-in closets plus a full bath. Launch a kayak, watch the sailboats or enjoy coastal birdlife from a wonderfully private vantage point. 2-car garage plus 4 driveway spaces! Set on a quiet one-way street with sidewalks, a nearby playground and restaurants within walking distance, this exceptional waterfront home offers privacy and a special coastal lifestyle.
Features of 109 Hillside Avenue
| MLS® # | 24201489 |
|---|---|
| Price | $1,975,000 |
| Bedrooms | 5 |
| Bathrooms | 4.00 |
| Full Baths | 3 |
| Half Baths | 1 |
| Square Footage | 2,932 |
| Acres | 0.11 |
| Type | Single Family For Sale |
| Style | Contemporary |
| Status | Active |
Community Information
| Address | 109 Hillside Avenue |
|---|---|
| Area | Woodmont |
| City | Milford |
| County | New Haven |
| State | Connecticut |
| Zip Code | 06460 |
Amenities
| Parking Spaces | 4 |
|---|---|
| Parking | Under House Garage, Off Street Parking, Driveway |
| # of Garages | 2 |
| Is Waterfront | Yes |
| Waterfront | L. I. Sound Frontage, Water Community, View, Access |
| Has Pool | No |
Interior
| Interior Features | Auto Garage Door Opener, Open Floor Plan, Security System |
|---|---|
| Appliances | Gas Cooktop, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer |
| Heating | Hot Air, Zoned, Natural Gas |
| Cooling | Central Air, Zoned |
| Fireplace | No |
| Has Basement | No |
| Basement | None |
Exterior
| Exterior | Cedar |
|---|---|
| Exterior Features | Balcony, Sidewalk, Garden Area, Lighting, Patio |
| Lot Description | Level Lot, Water View |
| Roof | Asphalt Shingle |
| Foundation | Masonry, Piling |
School Information
| Elementary | J. F. Kennedy |
|---|---|
| Middle | East Shore |
| High | Joseph A. Foran |
Additional Information
| Date Listed | August 25th, 2026 |
|---|---|
| Days on Market | 13 |
| Zoning | R5 |
| RE / Bank Owned | No |
Listing Details
| Office | Coldwell Banker Realty |
|---|