Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$715,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,620 Sq. Ft.
  • 2 Car Garage
  • Updated 9 hours ago
See This Home
Save This Home
See This Home
Save This Home
Welcome to 39 Lookout Hill, a beautifully maintained 3 bedroom Colonial in the highly sought-after Lexington Green community, for those seeking a low-maintenance lifestyle and an effortless daily commute. Boasting 0ver 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, leave the yard work behind, and start enjoying coastal Connecticut living!

Full Property Details for 39 Lookout Hill Rd

General

  • Price: $715,000
  • HOA FEE: $160/month
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24179486
  • Updated: 6/18/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 9
  • Rooms/Areas: Laundry Room
  • Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Oven/Range, Microwave, Refrigerator, Disposal, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Full Bath, Walk-In Closet, Wall/Wall Carpet, 14 x 13, Upper
  • Bedroom 1: Bedroom - Wall/Wall Carpet, 12 x 10, Upper
  • Bedroom 2: Bedroom - Wall/Wall Carpet, 12 x 10, Upper

Other Rooms

  • Living Room: Living Room, 14 x 14, Main
  • Family Room: Family Room - Fireplace, 12 x 12, Main
  • Kitchen: Kitchen - Remodeled, Granite Counters, Island, 18 x 14, Main
  • Dining Room: Dining Room, 12 x 12, Main
  • Office: Office - Wall/Wall Carpet, 25 x 10, Lower
  • Game room: Yes
  • Game Room: Rec/Play Room - Wall/Wall Carpet, 18 x 12, Lower
  • Rec Room: Wall/Wall Carpet, 18 x 12, Lower

Exterior

  • Exterior Features: Underground Utilities, Porch, Deck, Gutters, Lighting
  • Color: Yellow

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: New Haven
  • Subdivision: Lexington Gardens
  • Driving Directions: GPS

School Information

  • Elementary School: Mathewson
  • Middle School: Harborside
  • High School: Jonathan Law

Community

  • Association: Yes
  • Home Owners Assn.: 1
  • Assoc. Fees Include: Trash Pickup, Property Management, Road Maintenance

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Hot Air, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Natural Gas, 40 Gallon Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Partially Finished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,620
  • Above Ground: 1,875 Sq. Ft.
  • Below Ground: 745 Sq. Ft.
  • Year Built: 1994

Lot Features

  • Lot Size (Acres): 0.17
  • Zoning: R30
  • Lot Description: In Subdivision, Lightly Wooded, Level Lot

Green Features

  • Energy Features: Generator, Storm Doors, Thermopane Windows

Financial Considerations

  • Association Fee: $160
  • Assoc Fee Freq.: Monthly
  • Assessment Amount: $298,250
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1216010
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Meet the listing agents

Meet the listing agents
— 39 Lookout Hill Rd —

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 39 Lookout Hill Rd

School District:Milford School District
NameGradesDistance
Mathewson School
466 West River St., Milford, CT 06460
K-21.1 mi
Meadowside School
80 Seeman's Ln., Milford, CT 06460
3-52 mi
Harborside Middle School
175 High Street, Milford, CT 06460
6-81.7 mi
Jonathan Law High School
20 Lansdale Avenue, Milford, CT 06460
9-122.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 39 Lookout Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/18/2026
Listed
$715,000
191.84%
MLS
4/05/1999
Sold
$245,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 39 Lookout Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,813
1%
$298,250
—
2023
$8,691
7%
$298,250
—
2023
$8,103
2%
$298,250
—
2022
$7,948
16%
$298,250
21%
2021
$6,827
—
$246,920
—
2020
$6,835
-4%
$246,920
—
2019
$7,087
3%
$246,920
—
2018
$6,850
—
$246,920
—
2017
$6,862
2%
$246,920
3%
2016
$6,699
—
$240,620
—
2015
$6,708
6%
$240,620
—
2011
$6,323
—
$240,620
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 39 Lookout Hill Rd

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Similar Properties near 39 Lookout Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

275 Wheelers Farms Rd, Milford, CT 06461 - Photo 1
$724,900

275 Wheelers Farms Rd  Milford, CT 06461

  • Single Family
  • Active
  • Updated 12 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,084
    Sq. Ft.
Listed by William Raveis Real Estate
325 W Rutland Rd, Milford, CT 06461 - Photo 1
$729,900

325 W Rutland Rd  Milford, CT 06461

  • Single Family
  • Active
  • Updated 10 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,162
    Sq. Ft.
Listed by ASJ Realty Partners
1425 James Farm Rd, Stratford, CT 06614 - Photo 1
$749,900

1425 James Farm Rd  Stratford, CT 06614

  • Single Family
  • Active
  • Updated 10 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,710
    Sq. Ft.
Listed by D. Thomas Homes
57 Wilbar Ave, Milford, CT 06460 - Photo 1
$749,900

57 Wilbar Ave  Milford, CT 06460

  • Single Family
  • Active
  • Updated 5 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,882
    Sq. Ft.
Listed by William Raveis Real Estate

Just Listed near 39 Lookout Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

632 Wheelers Farm Rd, Orange, CT 06477 - Photo 1 Just Listed
$639,900
Open House

632 Wheelers Farm Rd  Orange, CT 06477

  • Single Family
  • Active
  • Updated 2 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,330
    Sq. Ft.
Listed by Allen Grealish (203) 623-8484
476 Derby-Milford Rd, Orange, CT 06477 - Photo 1 Just Listed
$749,000
Open House

476 Derby-Milford Rd  Orange, CT 06477

  • Single Family
  • Active
  • Updated 1 day ago
  • 6
    Beds
  • 4
    Total Baths
  • 2,384
    Sq. Ft.
Listed by Re/Max Prestige Properties
65 South Lakeside Dr, Orange, CT 06477 - Photo 1 Just Listed
$460,000

65 South Lakeside Dr  #65  Orange, CT 06477

  • Townhouse
  • Active
  • Updated 3 days ago
  • 2
    Beds
  • 4
    Total Baths
  • 1,330
    Sq. Ft.
Listed by Huntsman,Meade & Partners Comp
206 Ocean Ave, Stratford, CT 06615 - Photo 1 Just Listed
$649,900
Open House

206 Ocean Ave  Stratford, CT 06615

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,196
    Sq. Ft.
Listed by Paula Testani (203) 452-3700 x332

Price Reduced near 39 Lookout Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

148 Kennedy Dr, Orange, CT 06477 - Photo 1 Price Reduced
-$55,000 (-15.71%)
$295,000

148 Kennedy Dr  Orange, CT 06477

  • Land Residential
  • Active
  • Updated 14 hours ago
  • 1.3
    Acres
Listed by Blue Lighthouse Realty, Inc
580 Housatonic Ave, Stratford, CT 06615 - Photo 1 Price Reduced
-$120,001 (-10.71%)
$999,999

580 Housatonic Ave  Stratford, CT 06615

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,006
    Sq. Ft.
Listed by Berkshire Hathaway NE Prop.
50 Vine St, Stratford, CT 06614 - Photo 1 Price Reduced
-$20,000 (-3.51%)
$549,000

50 Vine St  Stratford, CT 06614

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,857
    Sq. Ft.
Listed by Ellison Homes Real Estate
315 Navajo Lane, Stratford, CT 06614 - Photo 1 Price Reduced
-$30,000 (-5.46%)
$519,000

315 Navajo Lane  #A  Stratford, CT 06614

  • Condo
  • Active
  • Updated 1 day ago
  • 2
    Beds
  • 3
    Total Baths
  • 1,434
    Sq. Ft.
Listed by eXp Realty

Recent Sales near 39 Lookout Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

82 Oak Ridge Ln, Milford, CT 06461 - Photo 1 Sold
$640,000

82 Oak Ridge Ln  Milford, CT 06461

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,248
    Sq. Ft.
Listed by Keller Williams Realty Prtnrs.
Sold by William Raveis Real Estate
143 Juniper Dr, Milford, CT 06461 - Photo 1 Sold
$787,500

143 Juniper Dr  Milford, CT 06461

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 2,966
    Sq. Ft.
Listed by Ellison Homes Real Estate
Sold by Keller Williams Realty Prtnrs.
42 Milford Hunt Ln, Milford, CT 06461 - Photo 1 Sold
$760,000

42 Milford Hunt Ln  Milford, CT 06461

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,665
    Sq. Ft.
Listed by Holli Shanbrom
Sold by Yi Gong
55 Spice Bush Ln, Milford, CT 06461 - Photo 1 Sold
$819,000

55 Spice Bush Ln  #55  Milford, CT 06461

  • Single Family
  • Closed
  • Updated 7 days ago
  • 2
    Beds
  • 3
    Total Baths
  • 2,820
    Sq. Ft.
Listed by Compass Connecticut, LLC
Sold by Compass Connecticut, LLC

39 Lookout Hill Road, Milford, CT 06461 (MLS# 24179486) is a Single Family property with 3 bedrooms, 3 full bathrooms and 1 partial bathroom. 39 Lookout Hill Road is currently listed for $715,000 and was received on June 18, 2026. This property is listed by Laureen Kennedy from our Cheshire Office.Want to learn more about 39 Lookout Hill Road? Do you have questions about finding other Single Family real estate for sale in Milford? You can browse all Milford real estate or contact a Coldwell Banker agent to request more information.

Tour this property