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109 Hillside Avenue

Milford, Connecticut 06460

COMING SOON - NEW$1,975,000
Beds
5
Baths
3 | 1
SqFt
2,932
Acres
0.11
Year Built
2000
Matt Caiola

Matt Caiola

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Waterfront2-Car Garage

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$12,598

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Carrie Sakey

(203) 521-1119

Coldwell Banker Realty

(203) 254-7100

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.