Skip to main content

299 West Main Street

Milford, Connecticut 06460

ACTIVE - NEW$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
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

Call Matt
1 FireplaceVirtual Tour

About This Home

Location, Location, Location! Walk to vibrant downtown Milford, the Milford Green, restaurants, shops, and the Metro-North train station (0.7 miles) with direct service to New York City from this meticulously renovated 3-bedroom, 2.5-bath Colonial. The inviting main level features beautiful hardwood floors throughout the spacious living room with a cozy fireplace and the formal dining room, creating the perfect setting for everyday living and entertaining. The beautifully designed eat-in kitchen offers quartz countertops, stainless steel appliances, abundant cabinetry, and flows seamlessly to a convenient main-level half bath. Upstairs, you'll find three generously sized bedrooms and two full baths, including a spacious primary suite with a beautifully tiled private bath and a walk-in closet featuring a custom organization system. A second oversized bedroom also offers a walk-in closet with custom organizers, while the third bedroom includes its own large walk-in closet, providing exceptional storage throughout. The full basement includes a washer/dryer combination system, ample storage space, and updated propane-fueled mechanicals. Outside, unwind on the expansive front porch, the perfect spot to enjoy your morning coffee or relax at the end of the day. Additional highlights include a roof that is less than two years old, thoughtful updates throughout, and an unbeatable location close to Milford's shoreline, downtown amenities, restaurants, shopping, and commuter routes.

Key Facts

City/Town
Milford
Neighborhood
N/A
Property / Style
Single Family · Colonial,Bungalow
Year Built
1910
Days on Market
0 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

75 active listings

Median $ / Sq Ft

$363

75 active listings

Sale-to-List Ratio

100.0%

432 sales

How this home compares

List Price

$575,000

vs $699,900 median

17.8% below median

Price / Sq Ft

$390

vs $363 median

7.4% above median

Days on Market

0 days

vs 37 days median

37 days fresher than median

Based on 75 active and 432 closed sales (trailing 12 mo) of single family in Milford. Source: SmartMLS · As of July 30, 2026.

Location

299 West Main Street, Milford, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,714

per month

  • Principal & Interest$2,932
  • Property Taxes$590
  • Insurance$192
  • 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 spacesDrivewayPavedSharedPaved
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
0
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 7/30/2026. 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 7/30/2026 at 6:55 PM UTC.