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44 Greenfield Road

Milford, Connecticut 06460

COMING SOON - NEW$875,000
Beds
4
Baths
3
SqFt
2,812
Acres
0.16
Year Built
2012
Matt Caiola

Matt Caiola

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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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,018

per 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

Similar Properties

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

Listed By

Stacy Pfannkuch

(203) 209-4989

Century 21 AllPoints Realty

(203) 378-0210

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.