109 Hillside Avenue
Milford, Connecticut 06460
- Beds
- 5
- Baths
- 3 | 1
- SqFt
- 2,932
- Acres
- 0.11
- Year Built
- 2000
- Neighborhood
- Woodmont
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
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.
Key Facts
- City/Town
- Milford
- Neighborhood
- Woodmont
- Property / Style
- Single Family · Contemporary
- Year Built
- 2000
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 3 full · 1 half
- Living Area
- 2,932 sq ft
- Lot Size
- 0.11 acres
- Garage / Parking
- 2 garage · 4 total
- Property Taxes
- $21,560 / Annually
Market Snapshot
The Milford Market
Single Family · trailing 12 months
Active Listings
85
85 under contract
Median List Price
$685,000
85 active listings
Median Closed Price
$557,000
446 sales
Median Days on Market
27
85 active listings
Median $ / Sq Ft
$363
85 active listings
Sale-to-List Ratio
100.0%
446 sales
How this home compares
List Price
$1.98M
vs $685,000 median
2.9× the median
Price / Sq Ft
$674
vs $363 median
85.7% above median
Days on Market
0 days
vs 27 days median
27 days fresher than median
Based on 85 active and 446 closed sales (trailing 12 mo) of single family in Milford. Source: SmartMLS · As of August 25, 2026.
Location
109 Hillside Avenue, Milford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 20, 2026per month
- Principal & Interest$10,143
- Property Taxes$1,797
- Insurance$658
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Milford
- Neighborhood
- Woodmont
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Contemporary
- Year Built
- 2000
- New Construction
- No/Resale
- Living Area
- 2,932 sq ft
Schools
- Elementary
- J. F. Kennedy
- High
- Joseph A. Foran
Interior
- Heating
- Hot AirZoned
- Heat Fuel
- Natural Gas
- Cooling
- Central AirZoned
- Laundry
- Upper Level
- Laundry Location
- Second Floor - Full Laundry Room
- Appliances
- Gas CooktopWall OvenRefrigeratorDishwasherWasherDryer
- Basement
- None
- Interior Features
- Auto Garage Door OpenerOpen Floor PlanSecurity System
- Additional Rooms
- FoyerLaundry Room
Exterior & Lot
- Lot Size
- 0.11 acres
- Zoning
- R5
- Garage / Parking
- 2 garage spaces4 total parking spacesUnder House GarageOff Street ParkingDrivewayPrivate
- Waterfront
- Direct waterfront
- Waterfront Details
- L. I. Sound FrontageWater CommunityViewAccess
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- Yes
- Construction
- Cedar
- Color
- Grey
- Roof
- Asphalt Shingle
- Foundation
- MasonryPiling
- Exterior Features
- BalconySidewalkGarden AreaLightingPatio
- Lot Description
- Level LotWater View
Listing & Financials
- Property Taxes
- $21,560 / Annually
- Days on Market
- 0
- MLS #
- 24201489
- MLS Status
- Coming Soon
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 8/25/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 8/25/2026 at 5:10 PM UTC.