9 Calloway Dr, Milford, CT 06461
Property image
Property image
OFF MARKET

$914,000

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 3,472 sqft (on 0.52 acres)

9 Calloway Dr, Milford, CT 06461

Est. Refi. Payment $6,601/mo*
Refinance Your Home
Currently Off Market - Sold Apr 26, 2022 for $800,000

Home Value

Trulia Estimate
$914K
Since last month
Decreased$9K (-1%)
Since last year
Increased$21K (+2.3%)
Since last sale
Increased$112K (+14%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +94% in the last 10 years
MonthEstimated value
2026
September 2026$912K
August 2026$922K
July 2026$921K
June 2026$938K
May 2026$926K
April 2026$919K
March 2026$906K
February 2026$895K
January 2026$879K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
41 calloway Drive, Milford, CT
0.07
Single-Family Home
$705,000
09/22/25
4
2.5
2,397
763 Woodruff Road, Milford, CT
0.26
Single-Family Home
$635,000
07/09/26
4
2.5
3,650
531 Woodruff Road, Milford, CT
0.44
Single-Family Home
$760,000
08/28/26
4
2.5
3,438
99 Cheryl Ann Drive, Milford, CT
0.42
Single-Family Home
$835,000
07/27/26
4
2.5
2,212
109 Green Meadow Road, Milford, CT
0.69
Single-Family Home
$750,000
06/22/26
3
3.5
3,000
324 Ridge Road, Orange, CT
0.45
Single-Family Home
$680,000
08/03/26
3
3
2,278
90 Terrell Drive, Milford, CT
0.07
Single-Family Home
$411,000
10/02/25
3
1.5
1,813
35 Flax Mill Terrace, Milford, CT
0.30
Single-Family Home
$740,000
09/18/25
4
3.5
2,586
558 Treat Lane, Orange, CT
0.30
Single-Family Home
$525,000
01/06/26
3
2.5
1,864
523 Treat Lane, Orange, CT
0.37
Single-Family Home
$620,000
11/14/25
4
2
1,738

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
74 Terrell Drive, Milford, CT 06461
0.06
$912,100
5
3
3,676
Off Market
90 Terrell Drive, Milford, CT 06461
0.07
$573,400
3
1.5
1,813
Off Market
41 calloway Drive, Milford, CT 06461
0.07
$731,100
4
2.5
2,397
Off Market
115 Kozlowski Road, Milford, CT 06461
0.19
$911,700
4
2.5
2,536
Off Market
645 Woodruff Road, Milford, CT 06460
0.20
$747,900
5
3.5
3,228
Off Market
763 Woodruff Road, Milford, CT 06461
0.26
$635,000
4
2.5
3,650
Recently Sold
35 Flax Mill Terrace, Milford, CT 06461
0.30
$788,300
4
3.5
2,586
Off Market
558 Treat Lane, Orange, CT 06477
0.30
$525,000
3
2.5
1,864
Recently Sold
528 Treat Lane, Orange, CT 06477
0.31
$683,700
3
2
2,296
Off Market
25 Talmadge Dr., Milford, CT 06461
0.35
$808,500
5
3.5
3,324
Off Market
80 Christine Terrace, Milford, CT 06461
0.41
$905,200
5
3
3,026
Off Market
523 Treat Lane, Orange, CT 06477
0.37
$683,800
4
2
1,738
Off Market

Local Information

  • Map ViewExplore the area around 9 Calloway Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2001
0.52 acre lot
3,472 sqft
$263/sqft
Garage

About this House

Welcome home to this immaculately cared for one owner colonial, nothing to do but move in! Set on a quiet private street with a wooded area bordering the rear of the property. The main level is light and bright throughout, offers a large open kitchen with center island open to the large family room with gas fireplace, large dining room right off kitchen with detailed chair rail moldings, dedicated home office with built in shelving, a living room offers additional hang out space, and gleaming hardwood floors throughout the main level, a half bathroom and tiled laundry room finish off the main level. The 2nd level offers a master suite with hardwood floor with his and her closets, recently redone master bathroom with double vanity (2021), 2 additional large bedrooms, a full main bathroom, and oversized bonus room or 4th bedroom with 2 walk in closets complete the upper level. The finished lower level has an in law style setup with kitchen and full bathroom, additionally there is plenty of space left for storage or to finish. This home also has a backyard paradise with trex deck leading to a private finished patio with an in ground pool with newer liner and pump. A whole house on demand generator, in ground sprinkler system, central vac system, whole house fan, central dehumidifier, and brand new gas furnace installed in Feb 2022 complete this turn key colonial.
9 Calloway Dr, Milford, CT 06461 is a 4 bedroom, 4 bathroom, 3,472 sqft single-family home built in 2001. It last sold for $800,000 on Apr 26, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $914,000, with a rent estimate of $5,212/month.

Home Details for 9 Calloway Dr

Interior Features

Interior Details
BasementAtticNumber of Rooms: 9
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2001
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.52 acres

Price and Tax history

DateEventPrice
Apr 26, 2022
Source: Smart MLS #170471884
Sold
$800,000
Mar 13, 2022
Source: Smart MLS #170471884
Contingent
$799,900
Mar 10, 2022
Source: Smart MLS #170471884
Listed For Sale
$799,900
Oct 25, 2001
Source: N/A
Sold
$400,000

Market trends in Milford

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$536K
$10.67KMoM
Sale-to-List Price
100.6%
0.6%MoM
Price per sq ft
$325
$1MoM
Available listings
159
18MoM

Around this home

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 streets are well-lit

  • 69 % Say there are sidewalks

  • 65 % Say kids play outside

  • 64 % Say there's wildlife

  • 64 % Say it's quiet

  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Alyx Prinz
    "Very dog friendly neighborhood. Everyone has pups and understands with grace when dogs bark. All are welcome here "
    0
    Flag
  • 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

LGBTQ Local Legal Protections

Frequently asked questions about 9 Calloway Dr

  • What is 9 Calloway Dr estimated to be worth?
    Trulia's estimated value for 9 Calloway Dr in Milford, CT is $914,000.
  • What is the price history for 9 Calloway Dr?
    9 Calloway Dr in Milford, CT last sold for $800,000 in April 2022.
  • Is Milford a buyer's or seller's market?
    Milford is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Milford?
    The median sale price in Milford is $536K. That is down $10.67K from the prior month.
  • Does 9 Calloway Dr have air conditioning?
    Yes, 9 Calloway Dr in Milford, CT has air conditioning.
  • Does 9 Calloway Dr have a pool?
    Yes, 9 Calloway Dr in Milford, CT has a pool.

Explore by feature - Pet Friendly

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