21 Middlebrook Drive, Fairfield, CT 06824
OFF MARKET

$976,600

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,616 sqft (on 0.26 acres)

21 Middlebrook Drive, Fairfield, CT 06824

Est. Refi. Payment $6,481/mo*
Refinance Your Home
Currently Off Market - Sold Jun 3, 2024 for $841,000

Home Value

Trulia Estimate
$977K
Since last month
Decreased$5K (-0.5%)
Since last year
Increased$76K (+8.4%)
Since last sale
Increased$137K (+16.3%)
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 +108% in the last 10 years
MonthEstimated value
2026
August 2026$978K
August 2026$977K
July 2026$983K
June 2026$990K
May 2026$983K
April 2026$975K
March 2026$980K
February 2026$951K
January 2026$933K
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
46 Middlebrook Drive, Fairfield, CT
0.04
Single-Family Home
$811,000
11/07/25
3
2
1,440
25 Millspaugh Drive, Fairfield, CT
0.12
Single-Family Home
$899,999
12/31/25
3
2
1,819
148 Millspaugh Drive, Fairfield, CT
0.19
Single-Family Home
$750,000
04/17/26
3
2
1,421
2465 Mill Plain Road, Fairfield, CT
0.25
Single-Family Home
$974,000
07/28/26
3
1.5
1,906
10 Millspaugh Drive, Fairfield, CT
0.15
Single-Family Home
$1,010,000
05/26/26
4
2
1,888
88 Middlebrook Drive, Fairfield, CT
0.07
Single-Family Home
$1,250,000
06/11/26
3
3
2,146
276 Carroll Road, Fairfield, CT
0.36
Single-Family Home
$760,000
11/07/25
3
1.5
1,244
14 Windsor Place, Fairfield, CT
0.68
Single-Family Home
$800,000
09/03/25
3
2
1,655
2032 North Benson Road, Fairfield, CT
0.49
Single-Family Home
$1,156,000
07/01/26
4
2
1,725
70 Allen Road, Fairfield, CT
0.62
Single-Family Home
$985,000
05/29/26
3
1.5
1,430

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
32 Middlebrook Drive, Fairfield, CT 06824
0.03
$1,978,200
6
5.5
5,109
Off Market
2225 Mill Plain Road, Fairfield, CT 06824
0.03
$847,100
3
2
1,698
Off Market
46 Middlebrook Drive, Fairfield, CT 06824
0.03
$811,000
3
2
1,440
Recently Sold
35 Crystal Lane, Fairfield, CT 06824
0.07
$985,000
3
3.5
3,191
Recently Sold
88 Middlebrook Drive, Fairfield, CT 06824
0.07
$1,250,000
3
3
2,146
Recently Sold
111 Middlebrook Drive, Fairfield, CT 06824
0.10
$1,105,700
3
1
1,134
Off Market
156 Ross Hill Road, Fairfield, CT 06824
0.12
$1,146,900
3
2.5
2,250
Off Market
114 Middlebrook Drive, Fairfield, CT 06824
0.10
$1,372,100
4
3
2,584
Off Market
130 Ross Hill Road, Fairfield, CT 06824
0.12
$997,600
3
2
2,186
Off Market
281 Orchard Hill Lane, Fairfield, CT 06430
0.12
$1,126,400
4
2.5
2,938
Off Market
33 Middlebrook Place, Fairfield, CT 06824
0.13
$2,025,000
4
5.5
5,256
Recently Sold

Local Information

  • Map ViewExplore the area around 21 Middlebrook Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1959
Lot Size
0.26 acres
Living Area
1,616 sqft
Price/Sqft
$604
Parking
1 Car Garage

About this House

Exciting, completely updated, immaculate with a touch of glam! This 3/4 bedroom split has all the bells and whistles. Quartz island and waterfall countertop, stainless appliances, wonderful Kitchen/Dining experience on first floor with access to one of TWO patios. Three bedrooms are all together on the Upper Level with Lucite handrail, hardwood flooring and updated full bathroom. The Family Room is found one level down with built ins, beverage fridge, and mirrored entertainment center. A second updated full bath is also found on the lower level along with a large mechanical room, laundry area and abundant storage in a spacious crawl space. The attached shed off the garage is another option to store sports equipment, bikes, and more. A potential in law- or fabulous office area is found off of the Family Room with access, through sliders, to a second patio overlooking a perfect play space with swing, climbing equipment and more. The professionally landscaped yard is fully fenced. Only 2.5 miles to the center of town, train and commuting on I-95, and 1.5 miles to the Merritt, Lake Mohegan with a water park and swimming beach. A luxury 18 hole golf course, tennis courts and hiking trails are also found nearby. Long Island Sound beaches are within 3 miles of this lovely home. Fairfield's town center is well known for its many exciting restaurants and nightlife. Completely turn key this home is a coastal Connecticut gem!
21 Middlebrook Drive, Fairfield, CT 06824 is a 3 bedroom, 2 bathroom, 1,616 sqft single-family home built in 1959. It last sold for $841,000 on Jun 3, 2024 (3% above the $820,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $976,600, with a rent estimate of $5,290/month.
Last check for updates: about 5 hours ago
Listed by Cindy Raney, (203) 257-8320
Coldwell Banker Realty, (203) 227-8424
Co-Listing Agent: Ginny Moffitt, (203) 610-3351
Coldwell Banker Realty, (203) 227-8424
Bought with: Helene Daly, (203) 913-4026, Compass Connecticut, LLC, (203) 489-6499
Source: Smart MLS, MLS#24007685

Home Details for 21 Middlebrook Drive

Interior Features

Interior Details
Basement: Crawl Space,Storage SpaceNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom, Family Room, Kitchen, Office
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1616 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Electric Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Wine Cooler, Water HeaterDishwasherDryerLaundry: Lower LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Hot Water,Zoned,OilHas CoolingAir Conditioning: DuctlessHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane Windows
Levels, Entrance, & Accessibility
Levels: Multi/Split

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: PatioFencing: Privacy, FullOther Structures: Shed(s)Exterior: Rain Gutters, LightingFoundation: BlockNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Attached,Paved,Driveway,Garage Door Opener,Private,Asphalt
Frontage
Waterfront: Water CommunityNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1616 Square Feet

Property Information

Year Built
Year Built: 1959
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Split Level
Building
Construction Materials: Shingle SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Not Included in Sale: trampolineParcel Number: 129106

Price & Status

Price
List Price: $820,000
Status Change & Dates
Off Market Date: Wed Apr 10 2024Possession Timing: Negot

Active Status

MLS Status: Closed

Location

Direction & Address
City: FairfieldCommunity: University
School Information
Elementary School: Osborn HillJr High / Middle School: Fairfield WoodsHigh School: Fairfield Ludlowe

Building

Building Area
Building Area: 1616 Square Feet

Community

Community Features: Golf, Lake, Library, Playground, Public Rec Facilities, Tennis Court(s)
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 0.26 acres

Energy

Energy Efficiency Features: Windows

Miscellaneous

BasementMls Number: 24007685Attic: Storage, Access Via HatchAbove Grade Unfinished Area: 1616

Additional Information

GolfLakeLibraryPlaygroundPublic Rec FacilitiesTennis Court(s)

Price and Tax history

DateEventPrice
Jun 3, 2024
Source: Smart MLS #24007685
Sold
$841,000
Apr 21, 2024
Source: Smart MLS #24007685
Pending
$820,000
Apr 3, 2024
Source: Smart MLS #24007685
PriceChange
$820,000
Price increased by 3%
Sep 23, 2022
Source: Smart MLS #170524888
Listed For Sale
$799,000
Mar 11, 2022
Source: Smart MLS #170449249
Sold
$765,000

Market trends in Fairfield

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$957K
$29.79KMoM
Sale-to-List Price
103.7%
0.4%MoM
Price per sq ft
$477
$5MoM
Available listings
162
16MoM

Around this home

What Locals Say about Fairfield

At least 343 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 87 % Say car is needed

  • 85 % Say parking is easy

  • 82 % Say yards are well-kept

  • 79 % Say there's holiday spirit

  • 76 % Say people would walk alone at night

  • 71 % Say kids play outside

  • 66 % Say they plan to stay for at least 5 years

  • 66 % Say it's quiet

  • 64 % Say there's wildlife

  • 61 % Say neighbors are friendly

  • 61 % Say there are sidewalks

  • 59 % Say streets are well-lit

  • 57 % Say it's walkable to restaurants

  • 50 % Say there are community events

  • 48 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • teddyabby
    "It’s safe and pretty and everyone looks out for one another. There is a bunch of cute parks and a nice walkable downtown."
    0
    Flag
  • Bnsdkbr225
    "Friendly and beautiful. Close to Lake Mohegan and parks. Lake rights to Lake Hill’s association . "
    0
    Flag
  • Kevin.cohen318
    "Great place to raise a family, incredibly safe and has all the amenities you could want on a year round basis."
    0
    Flag
  • Alexande.pappas
    "Yes walking miking kids walking to school we have public beaches lake’s plenty of restaurants churches"
    0
    Flag
  • Samuel Rivera
    "Great town for families with kids. Fairfield offers great schools, good supermarkets, tons of restaurants and entertainment "
    0
    Flag
  • Timothy Moss
    "Very family friendly. Great place to live for people of any age. I’ve lived here for 10 years now….."
    0
    Flag
  • Kevin.cohen318
    "5 minutes to either I-95, the Merritt Parkway or metro north, train to NYC is just over an hour each way. Great town that’s close to everything but not too close to anything."
    1
    Flag
  • Trulia User
    "My neighbor is safe and friendly and very clean as well. I've lived in this neighborhood over 18 years and absolutely love it. Thank you "
    3
    Flag
  • Trulia User
    "A very well maintained area . Homes streets ,business ,beaches schools ,library’s ( 3 ) . So much to offer !"
    0
    Flag
  • Sauerh
    "My neighborhood is family-oriented with distinct yet harmonious homes with well- kept yards. We are a short trip from Bridgeport, Norwalk, and Stamford with excellent connections via Metro North and I-95."
    5
    Flag
  • Isabellecj
    "Great neighborhood , good schools, close to town and railway station and beach . Very safe and quiet , properties well maintained and kids friendly . Love my neighborhood!"
    3
    Flag
  • Collin M.
    "Tons of events. Parties. Free concerts etc. there is so much fun things to do and see here. Beaches are amazing!"
    0
    Flag
  • Ab h
    "Walk to absolutely everything from hop on the train to yankee stadium or going to your dentist. Beautiful beaches and parks at your fingertips and children’s activities galore."
    0
    Flag
  • Juan G.
    "Quiet, clean and a good place to raise your kids. The school system it’s awesome and you know your kids are in good hands. "
    1
    Flag
  • Imeiers
    "We have neighbourhood block parties, the best trick or treating in town and a wonderful community spirit. Easily one of the best neighbourhoods in Fairfield. "
    5
    Flag
  • Troy P.
    "I work in Fairfield and it’s a wonderful town. The drive from New Haven is pretty easy with 2 route options either 95 or the merit parkway. "
    0
    Flag
  • Juan G.
    "Best in Connecticut, I have lived here for 6 years and my kids love it. If you want a place to raise your kids this it is the place "
    0
    Flag
  • Sar K.
    "Block parties, neighborhood watch, strong neighbor community, varying ages, active community, holiday celebrations: memorial parade, pancake breakfast, Christmas tree lighting, movies at the beach, music on the green, amazing local restaurants, 4th of July fireworks and much more"
    3
    Flag
  • DE
    "Very safe and relatively diverse. Great schools and decent restaurants. The beach is close by and some good golf courses."
    1
    Flag
  • Raquel.noi
    "Would love it, plenty of space for the dogs to run. Walking trails, beautiful neighborhoods to got for a walk. You will love it here!!"
    0
    Flag
  • Raquel
    "Great place, great community environment! It is such nice to go for walks and feel safe. We love that we found our home here!"
    0
    Flag
  • Raquel
    "Great family environment, lots of parks. Neighbors are friendly and welcoming. A lot of activities for kids. "
    0
    Flag
  • Lisalberts
    "It’s friendly and easy to walk or ride bikes around. The schools are wonderful. A real community feel."
    0
    Flag
  • Alek M.
    "Great town to raise a family, good schools and safe neighborhoods for your kids. Friendly people and clean area all around."
    1
    Flag
  • Fortress.management
    "Excellent schools, great town amenities makes it a great area to raise a family. Commuting to NYC is a little over an hour. Vibrant restaurant scene."
    0
    Flag
  • John S. W. J.
    "A great family oriented town. We love the parks the beaches and the community atmosphere. We couldn’t imagine living anywhere else"
    0
    Flag
  • Blythe A. B.
    "Driving to the train station is easy but parking passes are hard to come by unless you find street parking. waiting list is 18 months. "
    0
    Flag
  • Blythe A. B.
    "Everyone walks their dogs. sidewalks are well maintained. there are plenty of parks as well, both dog parks and free space parks. it is well kept by all dog owners, and it’s expected that you pick up after them!"
    0
    Flag
  • Bellaamore99
    "Close to parks, Wholefoods , Homedepo, shopping and metronorth train. Great neighbores . And feel very safe. "
    5
    Flag
  • Mjcejbart
    "Dog walking Mecca at lake Mohegan. All dogs welcome. Very dog friendly. Nice lake and trails to enjoy with or without a dog. "
    0
    Flag
  • Cheetah4455
    "Christmas walk around in Toilsome Hill. Meet the neighbors and everyone brings a different plate of food"
    1
    Flag
  • al .P
    "Lots of dogs on leaches . Not having your dog on a leach is not a good idea . You know your dog but the other does not know your dog "
    1
    Flag
  • Nour Y.
    "One dog can annoy a lot of families since homes are close to each other so multiple dogs barking is even worse"
    5
    Flag
  • Bassickrachel
    "I do see dogs frequently. People seem friendly, neighbors are quiet. I love airfield for the commute and small Town atmosphere."
    1
    Flag
  • Bassickrachel
    "Excellent I am 5 minutes from I-95 and Fairfield Metro Train Station. It is close to grocery stores and it is quite with friendly people."
    0
    Flag
  • Dennis
    "Many dogs that are very pleasant. Owners stop and chat while dogs play. Great way to meet your neighbors."
    0
    Flag
  • Larry
    "Moved here from Dallas and absolutely love it. I commute to downtown New Haven by car and it’s about 30-35 minutes."
    0
    Flag

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Frequently asked questions about 21 Middlebrook Drive

  • What is 21 Middlebrook Drive estimated to be worth?
    Trulia's estimated value for 21 Middlebrook Drive in Fairfield, CT is $976,600.
  • What is the price history for 21 Middlebrook Drive?
    21 Middlebrook Drive in Fairfield, CT last sold for $841,000 in June 2024.
  • Is Fairfield a buyer's or seller's market?
    Fairfield is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Fairfield?
    The median sale price in Fairfield is $957K. That is down $29.79K from the prior month.
  • Does 21 Middlebrook Drive have air conditioning?
    Yes, 21 Middlebrook Drive in Fairfield, CT has air conditioning.
  • Does 21 Middlebrook Drive have laundry facilities?
    Yes, 21 Middlebrook Drive in Fairfield, CT has in-unit laundry.

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