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5 Highland Court

Milford, Connecticut 06461

PENDING$1,350,000
Beds
5
Baths
4
SqFt
3,900
Acres
0.33
Year Built
2023
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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Pool3-Car Garage1 Fireplace

About This Home

Welcome to Highland Estates! Enjoy this exceptional 4,000 sqft modern residence in the beautiful private community of Highland Estates in Milford, Connecticut. Nestled on a private street, this nearly new home delivers the perfect blend of sophisticated living, smart technology, and outdoor luxury. Built in 2023, the home is designed for effortless modern living. It is a true smart house with smart lights throughout, including permanent Govee lighting, under-cabinet lighting, and high-efficiency systems that keep energy costs low. Enjoy high-efficiency appliances, gas appliances, and a showpiece 48-inch stove in a kitchen featuring elegant quartz countertops. The finished walk-out basement opens directly to the backyard and includes a wet bar plus a full bathroom and potential 6th bedroom-ideal for entertaining. Step outside to your private resort-style backyard featuring a heated 16x32-foot in-ground pool complete with waterfall features. Additional highlights include: Spray-foam insulated attic for superior efficiency, three-car fully finished garage with an 800 sqft bonus room above, ready to finish for extra living space, office, or gym. This is rare newer construction home on a private street in one of Milford's most sought-after communities. Move-in ready and packed with premium finishes and smart features, this home is ready for its second set of owners, and has your name written all over it.

Key Facts

City/Town
Milford
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
2023
Days on Market
4 days
Beds
5
Baths
4 full
Living Area
3,900 sq ft
Lot Size
0.33 acres
Garage / Parking
3 garage · 6 total
Property Taxes
$14,529 / Annually
HOA Fee
$200 / Monthly

Market Snapshot

The Milford Market

Single Family · trailing 12 months

Median Days on Market

43

72 active listings

Median $ / Sq Ft

$382

72 active listings

Sale-to-List Ratio

100.0%

434 sales

How this home compares

List Price

$1.35M

vs $694,450 median

94.4% above median

Price / Sq Ft

$346

vs $382 median

9.4% below median

Days on Market

4 days

vs 43 days median

39 days fresher than median

Based on 72 active and 434 closed sales (trailing 12 mo) of single family in Milford. Source: SmartMLS · As of July 28, 2026.

Location

5 Highland Court, Milford, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$8,744

per month

  • Principal & Interest$6,883
  • Property Taxes$1,211
  • Insurance$450
  • HOA$200

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
Subdivision
Highland Estates

Residence

Property Type
Single Family
Style
Colonial
Year Built
2023
New Construction
No/Resale
Living Area
3,900 sq ft
Below Grade
1,000 sq ft

Schools

Elementary
Per Board of Ed
High
Jonathan Law

Interior

Heating
Hot Air
Heat Fuel
Natural Gas
Cooling
Central Air
Fireplaces
1
Laundry
Upper Level
Appliances
Gas CooktopOven/RangeMicrowaveRange HoodDishwasherDisposalWasherDryer
Basement
FullFully FinishedLiveable SpaceFull With Walk-Out
Interior Features
Auto Garage Door OpenerOpen Floor Plan
Additional Rooms
Bonus Room

Exterior & Lot

Lot Size
0.33 acres
Zoning
R18
Garage / Parking
3 garage spaces6 total parking spacesAttached GaragePavedOff Street ParkingDrivewayPrivatePaved
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Pool
HeatedSafety FenceVinylIn Ground Pool
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
BalconyHot TubPatio
Lot Description
Fence - FullIn SubdivisionLevel LotOn Cul-De-SacProfessionally Landscaped

HOA / Association

Fee
$200 / Monthly

Listing & Financials

Property Taxes
$14,529 / Annually
Days on Market
4
MLS #
24194143
MLS Status
Under Contract

Similar Properties

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

Listed By

Courtney McManus

(203) 306-8069

The Agency

(203) 290-0333

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

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 5:20 AM UTC.