14 Whippoorwill Dr, Milford, CT 06460
Property image
Property image
OFF MARKET

14 Whippoorwill Dr
Milford, CT 06460

  • 3 Beds
  • 1 Bath
  • 2,400 sqft (on 0.45 acres)

$465,100

Trulia Estimate
as of Jul 15, 2026
Est. Refi. Payment $3,253/mo*
Refinance Your Home

$465,100

Trulia Estimate
as of Jul 15, 2026
Est. Refi. Payment $3,253/mo*
Refinance Your Home
3 Beds
1 Bath
2,400 sqft
(on 0.45 acres)

Local Information

  • Map ViewExplore the area around 14 Whippoorwill Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This house is located in a purely residential area, on .44 acres with a great backyard for entertaining and fun with an oversized deck. Three bedroom, one bathroom and spacious living room round up the living area. The1200 SF basement is unfinished and dry, perfect for additional living space or workshop / utility area. The furnace and water heater are newer and being serviced on a regular basis. The roof is 5 years old. Sewer is in the street and can easily be connected to the house. The House is in move in condition but needs some TLC.
14 Whippoorwill Dr, Milford, CT 06460 is a 3 bedroom, 1 bathroom, 2,400 sqft single-family home built in 1965. It last sold for $238,000 on Jan 30, 2020. It is currently off market. The Trulia Estimate is $465,100, with a rent estimate of $2,968/month.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 14 Whippoorwill Dr

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: Forced Air, Electric, OilHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Appliances & Utilities
Cable ReadyDryerRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodPatioPorch
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1965
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.45 acres

Price History for 14 Whippoorwill Dr

DatePriceEventSource
01/30/2020$238,000Sold
Smart MLS #170253464
11/20/2019$235,000Listed For SaleAgent Provided

Market trends in Milford

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$519K
$54.83KMoM
Sale-to-List Price
100.5%
Price per sq ft
$325
$16MoM
Available listings
190
13MoM
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Property Tax and Assessment

Year2025
Tax$7,002
Assessment$236,960
Home facts updated by county records

Comparable Sales for 14 Whippoorwill Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
583 Anderson Ave, Milford, CT
0.29
Single-Family Home
$250,000
05/04/26
3
1
1,360
467 Ansantawae Rd, Milford, CT
0.12
Single-Family Home
$700,000
06/17/26
3
2
2,000
35 Whippoorwill Drive, Milford, CT
0.06
Single-Family Home
$490,000
12/18/25
3
2.5
3,160
39 Kenwood Rd, Milford, CT
0.25
Single-Family Home
$246,666
02/04/26
3
1
1,000
44 Columbia Drive, Milford, CT
0.21
Single-Family Home
$435,000
11/21/25
3
1
1,248
21 Lyda Drive, Milford, CT
0.10
Single-Family Home
$600,000
04/22/26
3
2.5
1,858
333 Anderson Avenue, Milford, CT
0.29
Single-Family Home
$410,000
08/25/25
3
1
1,008
404 Ansantawae Road, Milford, CT
0.18
Single-Family Home
$610,000
07/08/26
3
2.5
1,712
22 Lyda Dr, Milford, CT
0.11
Single-Family Home
$640,000
08/05/25
3
2
1,338
17 Chelsea Circle, Milford, CT
0.17
Single-Family Home
$535,000
09/10/25
3
2
1,132

Nearby homes

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Assigned Schools

These are the assigned schools for 14 Whippoorwill Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Milford

At least 405 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 85 % Say car is needed

  • 84 % Say parking is easy

  • 79 % Say there's holiday spirit

  • 79 % Say yards are well-kept

  • 77 % Say people would walk alone at night

  • 69 % Say there are sidewalks

  • 68 % Say streets are well-lit

  • 64 % Say there's wildlife

  • 64 % Say it's quiet

  • 64 % Say kids play outside

  • 63 % Say it's walkable to restaurants

  • 61 % Say they plan to stay for at least 5 years

  • 57 % Say neighbors are friendly

  • 49 % Say it's walkable to grocery stores

  • 44 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Irene.a.burgdorf
    "Memorial Day and Labor Day picnics, Friday night meet ups"
    0
    Flag
  • Poochewluvr
    "The grammar school and high school are a 3 and 5 minute walk from my house. We have our own hospital in town, train station and shopping mall. We also have the longest coastline and beaches in Connecticut."
    1
    Flag
  • Keith A.bolden Sr
    "Every holiday they do something always working to make everyone feel better , excellent neighbors and police etc"
    0
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  • Angelsofmine S
    "I moved here about 20 years ago and love it. It’s a nice family area but also has a lot of stuff to do. "
    0
    Flag
  • Marnie Weber
    "Great schools! Friendly neighbors. Beautiful walks. Lots of kids. Plenty to do at the beach and surrounding areas."
    0
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  • Scorpionrkg
    "A little on a heavy traffic side on certain areas of Milford, by the pilot exit 40, 38, 39, 36, also the areas by 35"
    0
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  • Scorpionrkg
    "A little bit close to the highway, but not too bad very expensive to get rent but if you have a good paying job is great"
    1
    Flag
  • Nataliia Valuieva
    "Safe and comfortable. It’s all about comfort and good people. I highly recommend. Schools are good, "
    0
    Flag
  • Christina
    "Lots of cars during summer times. Less parking and a lot of people speeding too. "
    0
    Flag
  • Weil.josh
    "I’ve enjoy living here in Milford in the Walnut Beach area and this is a friendly town a hidden gem on the LI Sound!"
    0
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  • Alyx Prinz
    "Very dog friendly neighborhood. Everyone has pups and understands with grace when dogs bark. All are welcome here "
    0
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  • Irene.a.burgdorf
    "We live on the Housatonic River and watch bald eagles from our deck, amazing! Great events downtown with great sense of community ."
    0
    Flag
  • Lilly K
    "The only major target in area but Malala isn’t great otherwise. Lots of major food shopping options and a Costco too. Track and regular commuter rail options from town center "
    0
    Flag
  • Lilly K
    "Easy access to commuter rail, apartment and single family living, lots of grocery stores and a mall with the only target for a few towns! "
    0
    Flag
  • Pen Vas
    "Great access to major highways and train, excellent public transport system. Local roads are well kept and are an alternative to highways."
    0
    Flag
  • Janette
    "Community involvement. Always something happening to enjoy. All ages. Friendly environment. Shoreline enjoyment. "
    3
    Flag
  • Scorpionrkg
    "A lot a nice fancy restaurant so all nice fancy places to Hear music convenient to highways and other places"
    1
    Flag
  • Scorpionrkg
    "It’s OK there’s a lot of traffic a lot of pot smoking people are good people lotta old people lotta good old properties people live, lived here for years"
    1
    Flag
  • Scorpionrkg
    "More leashed does may more pet park or dog groups or dog lanes to walk there dogs and I’m not sure what else to add to this"
    2
    Flag
  • Trulia User
    "LBA & Walnut Beach events, restaurants, beaches and a sense of timeless tradition and community. Special area to live in. Glad to be part of it. "
    0
    Flag
  • Cheryl W.
    "Milford is an eclectic mix of people all interested in the same thing ~ we want to live our lives in peace and harmony!"
    14
    Flag
  • Dennis.manzi52
    "good schools , good sports programs.very nice library. Milford is very friendly,caring and alot to do in the center. Community support in the arts. "
    2
    Flag
  • Rebecca C.
    "There are families in the area and it is a great place for kids to grow up. Everyone waves at everyone on the street. You will get to know your neighbors as they are very sweet."
    0
    Flag
  • Michngus
    "Yes I do think it’s very important for parents to know what’s going on though out the city and the schools are great "
    1
    Flag
  • Mendilloa15
    "Most neighbors have fences in the backyard for their dogs to run! All of our neighbors are respectful and use a leash to walk their dogs. "
    0
    Flag
  • Janette
    "Easy in off 95 and Merritt parkway. Very safe Trains station close to the town green. Gas stations close to roadways "
    2
    Flag
  • Janette
    "Super friendly. Clean. Environment conscious. Community involvement opportunities always. Most importantly, I feel my children and I are safe. "
    1
    Flag
  • Ran1500519
    "Dog owners would like the scenery and how close they are to everything. Milford has a lot to offer. "
    0
    Flag
  • Trulia User
    "Well run city that feels like a town in most areas. Good communities, good schools, great commerce and restaurants. "
    0
    Flag
  • Adwana
    "Quiet but convenient to major highways and shopping. Neighbors are kind. Walkable to downtown and beach, no thru traffic."
    4
    Flag
  • Helenefoust
    "Walnut beach district has many opportunities for families to enjoy the beach area. Farmers market has a nice community feel. "
    2
    Flag
  • Ran1500519
    "Too many fast moving cars down the streets loud vehicles. Mean neighbors . They would like the scenery "
    5
    Flag
  • Asia S.
    "I like the neighborhood because it’s nice and quiet my kids love it too and the schools are nice here"
    0
    Flag
  • Cwalker
    "They have music in the summer, Milford oyster fest. Great 4th of July and New Years fireworks. Milford does a holiday tree lighting every year. The city has beautiful beaches, with sand castle sculpture contested, pumpkins on the pier, paddle board lessons, biking and walking trails and so much more. We recently got into pickle ball because MILFORD just put in 8 courts at Eisenhower park. You’ll never run out of things to do in this town. "
    0
    Flag
  • Megankirkpatrick
    "It’s in walking distance to the quaint Walnut Beach section of town. You can grab a lobster roll or an ice cream and walk along the boardwalk that leads to Silver Sands beach."
    0
    Flag
  • Dellamonicaj
    "Very close to schools, Long Island Sound, shopping and mass transit. Very quiet neighborhoods with plenty of kids living in the area. "
    0
    Flag
  • JS
    "Very busy street. Too close to US1. Street noise is extremely loud so it’s difficult to get down time."
    0
    Flag
  • Stephan A.
    "The trails all over the more you walk the more you discover of this wonder hide away it's just a beautiful place to live iovebut here."
    0
    Flag
  • Stephan A.
    "Trails are awesome. With sidewalks to use to easily walk your companion for their exercise. The Bridge around Milford Library has an awesome view of the docks."
    0
    Flag
  • Murphy
    "It’s ok, dogs aren’t technically allowed on the beach and sidewalks are hit or miss. Inconsiderate neighbors speed through the neighborhood. "
    1
    Flag

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Homes for sale near 14 Whippoorwill Dr

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Off Market Homes Near 14 Whippoorwill Dr

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