44 Greenfield Road
Milford, Connecticut 06460
- Beds
- 4
- Baths
- 3
- SqFt
- 2,812
- Acres
- 0.16
- Year Built
- 2012
- Neighborhood
- Fort Trumbull Beach
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Coastal New England Elegance Meets Effortless Modern Living. This exceptional home captures the quintessential charm of a Martha's Vineyard retreat, beautifully interpreted for todays living. Cedar shake siding, timeless architectural appeal, & a warm, inviting interior create an atmosphere that is both refined & relaxed. A generous front porch sets the tone, offering the perfect place to enjoy a morning coffee or unwind at the end of the day, while the back patio extends the living outdoors & creates inviting spaces for dining, entertaining, and relaxing. Inside, the gorgeous hardwood floors flow throughout an open & thoughtfully designed floor plan, while the 14-year-old mechanical systems & roof provide comfort & peace of mind. At the heart of the home is an impressive open-concept kitchen and great room, designed for everything from quiet evenings to effortless entertaining. A first-floor office or guest room offers exceptional flexibility. You are sure to love the drop-zone/mudroom area with an abundant amount of storage perfectly organized, a place for the pups, & a full bath this space is all you hoped for! Head up the back stairs to a versatile bonus room/flex space that provides endless possibilities for a guest retreat, playroom, or recreation space. The upstairs boasts 3 generously appointed bedrooms including a serene primary suite with its own spacious full bath & walk in closet. Along with the large hall bath, is the added convenience of a upper-level laundry.
Key Facts
- City/Town
- Milford
- Neighborhood
- Fort Trumbull Beach
- Property / Style
- Single Family · Colonial
- Year Built
- 2012
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 3 full
- Living Area
- 2,812 sq ft
- Lot Size
- 0.16 acres
- Garage / Parking
- 1 garage
- Property Taxes
- $13,099 / Annually
Market Snapshot
The Milford Market
Single Family · trailing 12 months
Active Listings
83
76 under contract
Median List Price
$674,999
83 active listings
Median Closed Price
$565,000
455 sales
Median Days on Market
32
83 active listings
Median $ / Sq Ft
$347
83 active listings
Sale-to-List Ratio
100.0%
455 sales
How this home compares
List Price
$875,000
vs $674,999 median
29.6% above median
Price / Sq Ft
$311
vs $347 median
10.4% below median
Days on Market
0 days
vs 32 days median
32 days fresher than median
Based on 83 active and 455 closed sales (trailing 12 mo) of single family in Milford. Source: SmartMLS · As of September 21, 2026.
Location
44 Greenfield Road, Milford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 17, 2026per month
- Principal & Interest$4,634
- Property Taxes$1,092
- Insurance$292
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Milford
- Neighborhood
- Fort Trumbull Beach
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 2012
- New Construction
- No/Resale
- Living Area
- 2,812 sq ft
Schools
- Elementary
- Meadowside
- High
- Jonathan Law
Interior
- Heating
- Hot AirHydro AirZoned
- Heat Fuel
- Natural Gas
- Cooling
- Central AirSplit System
- Fireplaces
- 1
- Laundry
- Upper Level
- Appliances
- Gas CooktopWall OvenRange HoodRefrigeratorDishwasherDisposalWasherElectric DryerWine Chiller
- Basement
- FullFully Finished
- In-Law Apartment
- Possible
- Interior Features
- Audio System
- Additional Rooms
- Bonus RoomMud Room
Exterior & Lot
- Lot Size
- 0.16 acres
- Zoning
- R7.5
- Garage / Parking
- 1 garage spaceAttached Garage
- Waterfront Details
- Walk to WaterWater Community
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- ShakeCedar
- Color
- brown
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- PorchGuttersLightingPatio
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $13,099 / Annually
- Days on Market
- 0
- MLS #
- 24207322
- 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 9/21/2026. 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 9/21/2026 at 3:05 PM UTC.