299 West Main Street
Milford, Connecticut 06460
Reduced from $575,000
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 1,476
- Acres
- 0.15
- Year Built
- 1910
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
83
63 under contract
Median List Price
$649,000
83 active listings
Median Closed Price
$570,000
460 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 29, 2026per 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
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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 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.