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299 West Main Street

Milford, Connecticut 06460

ACTIVE$515,000

Reduced from $575,000

Beds
3
Baths
2 | 1
SqFt
1,476
Acres
0.15
Year Built
1910
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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About This Home

Location, Location, Location! Timeless charm meets modern updates in this beautifully renovated 3-bedroom, 2.5-bath Colonial, just 0.7 miles from vibrant downtown Milford, the Green, restaurants, shops, and Metro-North with direct service to NYC. From the moment you enter, you'll appreciate the beautiful hardwood floors, detailed woodwork, and craftsmanship rarely found in today's construction. The spacious living room with fireplace and formal dining room offer warmth and character while blending seamlessly with today's updates. The beautifully designed kitchen features quartz countertops, stainless steel appliances, abundant cabinetry, and a convenient half bath nearby. Upstairs are three generously sized bedrooms and two full baths, including a spacious primary suite with a beautifully tiled private bath and custom-organized walk-in closet. Both additional bedrooms offer impressive walk-in closets, providing exceptional storage. The full basement includes a washer/dryer combination, ample storage, and updated propane-fueled mechanicals. Outside, the expansive front porch adds to the home's classic appeal and is the perfect place to relax. With a roof less than two years old, thoughtful renovations throughout, and beautiful original character preserved, this home truly offers the best of old-world charm and modern-day living, all in an exceptional Milford location.

Key Facts

City/Town
Milford
Neighborhood
N/A
Property / Style
Single Family · Colonial,Bungalow
Year Built
1910
Days on Market
94 days
Beds
3
Baths
2 full · 1 half
Living Area
1,476 sq ft
Lot Size
0.15 acres
Garage / Parking
2 total
Property Taxes
$7,074 / Annually

Market Snapshot

The Milford Market

Single Family · trailing 12 months

Median Days on Market

37

83 active listings

Median $ / Sq Ft

$336

83 active listings

Sale-to-List Ratio

100.0%

460 sales

How this home compares

List Price

$515,000

vs $649,000 median

20.6% below median

Price / Sq Ft

$349

vs $336 median

In line with median

Days on Market

94 days

vs 37 days median

57 days longer than median

Based on 83 active and 460 closed sales (trailing 12 mo) of single family in Milford. Source: SmartMLS · As of November 1, 2026.

Location

299 West Main Street, Milford, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,570

per month

  • Principal & Interest$2,808
  • Property Taxes$590
  • Insurance$172
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Milford
Neighborhood
N/A
County
New Haven

Residence

Property Type
Single Family
Style
Colonial,Bungalow
Year Built
1910
New Construction
No/Resale
Living Area
1,476 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Air
Heat Fuel
Propane
Cooling
Central Air
Fireplaces
1
Laundry
Lower Level
Laundry Location
Washer/Dryer combo unit in basement
Appliances
Gas RangeRange HoodRefrigeratorDishwasherWasherDryer
Basement
FullUnfinishedFull With Hatchway

Exterior & Lot

Lot Size
0.15 acres
Zoning
R12.
Garage / Parking
2 total parking spacesPavedDrivewaySharedPaved
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Clapboard
Color
Blue
Roof
Asphalt Shingle
Foundation
Stone
Exterior Features
Porch
Lot Description
Level Lot

Listing & Financials

Property Taxes
$7,074 / Annually
Days on Market
94
MLS #
24195357
MLS Status
Active
Financing
FHA,VA,CHFA

Similar Properties

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

Listed By

Tara Stirk

(203) 650-3180

William Raveis Real Estate

(203) 876-7507

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 11/1/2026. 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 11/1/2026 at 5:15 PM UTC.