3 Brookside Dr, Middlebury, CT 06762
OFF MARKET

$695,400

Trulia Estimate
as of Aug 29, 2026
  • 4 Beds
  • 2.5 Baths
  • 4,200 sqft
  • 4 Beds
  • 2.5 Baths
  • 4,200 sqft

3 Brookside Dr, Middlebury, CT 06762

Home Highlights

Property Type
Single-Family Home
Living Area
4,200 sqft
Price/Sqft
$166
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 3 Brookside Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Elegant 4-Bedroom Home in Brookside of Middlebury Move-In Ready
Discover refined comfort and timeless elegance in this beautifully maintained Cheshire model, located in the highly desirable Brookside of Middlebury community. This exceptional 4-bedroom, 2 full and 2 half bath home offers a spacious, open-concept layout designed for both everyday living and effortless entertaining.
The stylish kitchen features granite countertops, newer LG appliances, and flows seamlessly into the main living areas. A convenient first-floor primary suite includes a luxurious jacuzzi tub and two generous walk-in closets. Just beyond, glass French doors lead to a versatile bonus space perfect as a dressing room or home office complete with a built-in wardrobe system and workspace.
The dramatic two-story foyer opens to the upper level, where you'll find three additional bedrooms and a full bath, all overlooking the stunning two-story living room with a cozy woodburning fireplace.
A finished walk-out basement provides flexible living space ideal for a home office, gym, media room, or recreation area, along with over 600 sq ft of additional storage and a workbench.
Enjoy peaceful mornings or unwind in the evenings on the expansive deck overlooking a serene, protected preserve.

This is more than just a rental it's a place to truly feel at home.

1 year, 2 year
3 Brookside Dr, Middlebury, CT 06762 is a 4 bedroom, 3 bathroom, 4,200 sqft single-family home. It last sold for $550,000 on Oct 20, 2006 (12,691% above the $4,300 asking price). More recently, it was listed as a rental in May 2026 with an asking price of $4,300 per month. That rental listing was removed on May 31, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $695,400, with a rent estimate of $4,157/month.

Home Details for 3 Brookside Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood, Tile

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Rent to OwnAvailable: now

Exterior Features

Parking & Garage
Parking: Attached, On Site

Comparable Sales for 3 Brookside Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
39 Independence Cir, Middlebury, CT
0.39
Single-Family Home
$600,000
11/26/25
4
3
3,682 sqft
6 Pommel Lane #6, Middlebury, CT
0.22
Single-Family Home
$525,000
10/16/25
2
2.5
1,917 sqft
23 Somerset Dr, Middlebury, CT
0.52
Single-Family Home
$899,000
12/18/25
3
3
3,323 sqft
13 Caveson Court #13, Middlebury, CT
0.41
Single-Family Home
$530,000
03/24/26
2
2
2,011 sqft
1 Hampshire Court, Middlebury, CT
0.65
Single-Family Home
$800,000
12/16/25
4
3.5
3,711 sqft
11 Hunting Ridge Road, Middlebury, CT
0.69
Single-Family Home
$820,000
12/18/25
4
2.5
2,700 sqft
3 Hunting Ridge Road, Middlebury, CT
0.69
Single-Family Home
$620,000
03/30/26
3
2.5
1,722 sqft
2 Deer Run Road, Middlebury, CT
0.75
Single-Family Home
$709,900
02/27/26
3
2.5
2,190 sqft
927 Southford Rd, Middlebury, CT
0.61
Single-Family Home
$650,000
07/15/26
3
2
1,548 sqft
38 Avalon Drive, Middlebury, CT
0.90
Single-Family Home
$815,000
07/29/26
3
2.5
3,217 sqft

Nearby homes

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Around this home

What Locals Say about Middlebury

At least 21 Trulia users voted on each feature.

  • 94 % Say yards are well-kept

  • 93 % Say parking is easy

  • 86 % Say car is needed

  • 82 % Say there's holiday spirit

  • 78 % Say there's wildlife

  • 72 % Say it's quiet

  • 63 % Say it's dog friendly

  • 58 % Say people would walk alone at night

  • 52 % Say kids play outside

  • 48 % Say they plan to stay for at least 5 years

  • 47 % Say neighbors are friendly

  • 45 % Say it's walkable to restaurants

  • 36 % Say streets are well-lit

  • 35 % Say there are sidewalks

  • 34 % Say there are community events

  • 27 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Ginacea313@gmail.com
    "It’s a beautiful community with little to no crime. There is a crystal clear lake and a small amusement park. Additionally, there are plenty of hiking trails. Autumn is quite amazing here, with many vibrant colors. "
    3
    Flag
  • Ginacea313@gmail.com
    "Middlebury is a beautiful town. It is truly a New England gem. Lake Quassapaug is clean and the MRA is well kept. Summers are heavenly here. "
    1
    Flag
  • Plandusky
    "Region 15 public schools are some of the best in the state. Middlebury, Southbury public schools. Safe neighborhoods lived here 27 years and could have left the car unlocked the whole time"
    0
    Flag
  • Cadecres
    "I’ve lived here 11 years now and everyone is friendly and thoughtful. This town is a hidden gem, just far enough away from the bustle yet close enough not to be isolated."
    0
    Flag
  • darrenwittko
    "With excellent schools and beautiful parks, Middlebury is the perfect family community. Close to I-84, it's great for commuters too."
    0
    Flag
  • Donathom1114
    "This is an excellent community for families. Top notch schools with excellent family activities. Private community with walking trails and child and pet friendly streets. Wonderful neighbors and pride of home ownership,"
    0
    Flag
  • castaway45
    "I grew up here, moved here when I was 9. Many fond memories. Great place to walk and for recreation, and for kids to play, points were neighbors, community spirit, natural setting."
    0
    Flag
  • Rtfa50
    "Great neighborhood for a family with children. Close proximity to I-84 both east and westbound. Excellent area for biking, hiking and walking. Easy access to neighboring towns such as Woodbury, Southbury and easy commute for professionals working in both Waterbury or Danbury. "
    0
    Flag
  • Hallie
    "I have lived here for 10 years and would not live anywhere else. The schools are fantastic, the parks beautiful, and the town beach perfect. Everywhere you look are flowers, towering oaks, and wonderful jogging paths. This is quintessential New England."
    0
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
May 31, 2026
Source: Zillow Rentals
ListingRemoved
$4,300
May 13, 2026
Source: Zillow Rentals
Listed For Rent
$4,300
Apr 24, 2026
Source: Zillow Rentals
ListingRemoved
$4,300
Apr 15, 2026
Source: Zillow Rentals
Listed For Rent
$4,300
Oct 20, 2006
Source: N/A
Sold
$550,000

Frequently asked questions about 3 Brookside Dr

  • What is 3 Brookside Dr estimated to be worth?
    Trulia's estimated value for 3 Brookside Dr in Middlebury, CT is $695,400.
  • What is the price history for 3 Brookside Dr?
    3 Brookside Dr in Middlebury, CT last sold for $550,000 in October 2006.
  • Is Middlebury a buyer's or seller's market?
    Middlebury is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Middlebury?
    Residents describe Middlebury, CT as well-kept, easy to park in, and quiet. Most residents say you need a car. See recently sold homes in Middlebury, CT.
  • Does 3 Brookside Dr have air conditioning?
    Yes, 3 Brookside Dr in Middlebury, CT has air conditioning.
  • Does 3 Brookside Dr have parking?
    Yes, 3 Brookside Dr in Middlebury, CT has on-site parking.

Homes for rent near 3 Brookside Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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