39 Lookout Hill Road
Milford, Connecticut 06461
Reduced from $715,000
- Beds
- 3
- Baths
- 3 | 1
- SqFt
- 2,620
- Acres
- 0.17
- Year Built
- 1994
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
BRAND NEW CENTRAL AIR IS BEING INSTALLED! TARGETING 7/31 FOR COMPLETION. Welcome to 39 Lookout Hill, a beautifully maintained 3 bedroom Colonial in the highly sought-after Lexington Greens community, for those seeking a low-maintenance lifestyle and an effortless daily commute. Boasting over 2600 square feet of thoughtfully utilized living space, this move-in-ready home features a dramatic two-story foyer. The updated eat-in kitchen-complete with granite countertops, stainless steel appliances, and a center island-makes meal prep and clean-up a breeze, opening directly to a spacious family room with sliders to a private deck. Overlooking a peaceful, wooded setting, this outdoor retreat offers a serene escape with absolutely zero yard maintenance required. Upstairs, the primary suite serves as a relaxing oasis with a walk-in closet and an updated bath and a walk-in shower, accompanied by two additional bedrooms and a full bath. Brand new carpeting on stairs and entire upstairs level. The fully finished lower level adds incredible flexibility with a rec room, full bath, potential fourth bedroom, office space or in-law setup. Whole house generator provides peace of mind no matter what the weather. Best of all, this home takes the stress out of travel, sitting just minutes from the train station, major highways, shopping, dining, and Milford's beautiful shoreline. Move right in, enjoy your smaller, private yard and start enjoying coastal Connecticut living!
Key Facts
- City/Town
- Milford
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1994
- Days on Market
- 40 days
- Beds
- 3
- Baths
- 3 full · 1 half
- Living Area
- 2,620 sq ft
- Lot Size
- 0.17 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $8,813 / Annually
- HOA Fee
- $160 / Monthly
Market Snapshot
The Milford Market
Single Family · trailing 12 months
Active Listings
72
94 under contract
Median List Price
$694,450
72 active listings
Median Closed Price
$550,500
434 sales
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
$675,000
vs $694,450 median
In line with median
Price / Sq Ft
$258
vs $382 median
32.5% below median
Days on Market
40 days
vs 43 days median
3 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
39 Lookout Hill Road, Milford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$3,442
- Property Taxes$734
- Insurance$225
- HOA$160
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
- Lexington Gardens
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1994
- New Construction
- No/Resale
- Living Area
- 2,620 sq ft
- Below Grade
- 745 sq ft
Schools
- Elementary
- Mathewson
- High
- Jonathan Law
Interior
- Heating
- Hot Air
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry Location
- First Floor
- Appliances
- Oven/RangeMicrowaveRefrigeratorDisposalWasherDryer
- Basement
- FullPartially Finished
- In-Law Apartment
- PossibleLower Level
- Interior Features
- Auto Garage Door OpenerCable - Pre-wiredOpen Floor Plan
- Additional Rooms
- Laundry Room
Exterior & Lot
- Lot Size
- 0.17 acres
- Zoning
- R30
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Color
- Yellow
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Underground UtilitiesPorchDeckGuttersLighting
- Lot Description
- In SubdivisionLightly WoodedLevel Lot
HOA / Association
- Fee
- $160 / Monthly
Listing & Financials
- Property Taxes
- $8,813 / Annually
- Days on Market
- 40
- MLS #
- 24179486
- MLS Status
- Under Contract - Continue to Show
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Co-Listed By
Kevin Kennedy
Coldwell Banker Realty
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 6:01 AM UTC.