44 Wyncum Valley Rd, Fairfield, CT 06824
Property image
Property image
OFF MARKET

$2,138,500

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 5,480 sqft (on 1.08 acres)

44 Wyncum Valley Rd, Fairfield, CT 06824

Est. Refi. Payment $14,793/mo*
Refinance Your Home
Currently Off Market - Sold Aug 6, 2021 for $1,425,000

Home Value

Trulia Estimate
$2.14M
Since last month
Decreased$17K (-0.8%)
Since last year
Increased$240K (+12.7%)
Since last sale
Increased$704K (+49.4%)
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 +93% in the last 10 years
MonthEstimated value
2026
September 2026$2.13M
August 2026$2.15M
July 2026$2.17M
June 2026$2.2M
May 2026$2.12M
April 2026$2.08M
March 2026$2.08M
February 2026$1.97M
January 2026$1.96M
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
757 Galloping Hill Road, Fairfield, CT
0.46
Single-Family Home
$2,025,000
06/11/26
4
2.5
3,728
145 Galloping Hill Road, Fairfield, CT
0.12
Single-Family Home
$3,300,000
06/02/26
5
5.5
8,925
45 Pheasant Lane, Fairfield, CT
0.32
Single-Family Home
$1,275,000
09/23/26
4
2.5
3,084
947 Galloping Hill Road, Fairfield, CT
0.65
Single-Family Home
$1,305,000
01/23/26
4
3.5
4,024
845 Mountain Laurel Road, Fairfield, CT
0.34
Single-Family Home
$1,180,000
02/12/26
4
2.5
2,068
545 Surrey Lane, Fairfield, CT
0.71
Single-Family Home
$1,290,000
10/30/25
4
2.5
3,360
1185 Stillson Road, Fairfield, CT
0.59
Single-Family Home
$1,360,000
08/17/26
3
2.5
2,788
475 Springer Road, Fairfield, CT
0.51
Single-Family Home
$2,050,000
08/24/26
5
4.5
6,427
1207 Stillson Road, Fairfield, CT
0.64
Single-Family Home
$1,545,000
02/20/26
5
4.5
4,073
2580 North Benson Road, Fairfield, CT
0.34
Single-Family Home
$1,725,000
09/24/26
5
3.5
3,254

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
120 Mountain Laurel Road, Fairfield, CT 06824
0.11
$1,287,300
4
3
2,800
Off Market
145 Galloping Hill Road, Fairfield, CT 06824
0.12
$3,300,000
5
5.5
8,925
Recently Sold
47 Trillium Circle, Fairfield, CT 06824
0.16
$1,288,100
4
3.5
3,266
Off Market
142 Trillium Road, Fairfield, CT 06824
0.18
$1,378,800
4
2.5
3,050
Off Market
147 Trillium Road, Fairfield, CT 06824
0.19
$1,837,000
4
3
4,176
Off Market
35 Stroll Rock Common, Fairfield, CT 06430
0.21
$1,623,100
4
3.5
4,300
Off Market
105 Stroll Rock Common, Fairfield, CT 06430
0.22
$1,965,700
4
3.5
4,750
Off Market
528 Brookside Drive, Fairfield, CT 06430
0.22
$844,000
3
2
1,308
Off Market
125 Stroll Rock Common, Fairfield, CT 06430
0.23
$1,872,300
4
3.5
4,300
Off Market
82 Springer Road, Fairfield, CT 06430
0.23
$1,716,800
4
3.5
3,636
Off Market
LOT 3 Galloping Hill Road, Fairfield, CT 06430
0.22
$1,630,900
4
3.5
3,800
Off Market
100 Stroll Rock Common, Fairfield, CT 06430
0.25
$1,393,200
4
3.5
3,648
Off Market

Local Information

  • Map ViewExplore the area around 44 Wyncum Valley Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1996
1.08 acre lot
5,480 sqft
$390/sqft
Garage

About this House

Rare opportunity to live in one of the most coveted neighborhoods in Lower Greenfield Hill with only 2 other homes on the block. Welcome to this beautifully maintained, immaculate and updated traditional colonial with an open floor plan, generous sized rooms, abundant natural sunlight w/ a comfortable easy flow for everyday living. The front entry leads to an elegant two-story foyer w/ stairway, spacious formal dining room and formal living room w/ pocket french doors. The heart of the home is the custom kitchen w/ plenty of counter space and cabinets, expansive center island, top of the line appliances, granite countertops, pantry & separate eating area. The flow continues through to the family rm featuring a floor-to-ceiling brick fireplace, custom built-in shelving & french doors leading to the rear yard. Finishing off the 1st floor is the spacious home office, laundry room & entrance to the 3-car garage.  Upstairs the master suite is its own retreat featuring a sizable walk-in closet, luxurious bath w/ oversized shower, jacuzzi tub & double sink. Three add'l large bedrooms, one is ensuite & two share a jack-and-jill bath. The fully finished lower level adds add'l 1,117 sq.ft. of living space, gym & plenty of storage area. The grounds are professionally landscaped w/ room for a pool & just MINUTES to Merritt Parkway, I-95, shopping, beach & 2 train stations. List of updates & Floor plans available. Enjoy the added privacy, acreage and prestige of a well sited residence.
44 Wyncum Valley Rd, Fairfield, CT 06824 is a 4 bedroom, 4 bathroom, 5,480 sqft single-family home built in 1996. It last sold for $1,425,000 on Aug 6, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,138,500, with a rent estimate of $9,708/month.

Home Details for 44 Wyncum Valley Rd

Interior Features

Interior Details
BasementNumber of Rooms: 9Types of Rooms: Laundry Room
Heating & Cooling
Heating: Forced Air, Electric, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Shingle Not Wood, WoodPatioPorch
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.08 acres

Building

Community rooms
Fitness Center

Price and Tax history

DateEventPrice
Aug 6, 2021
Source: Smart MLS #170407181
Sold
$1,425,000
Aug 19, 2020
Source: Agent Provided
ListingRemoved
$1,149,000
Aug 14, 2020
Source: Agent Provided
PendingToActive
$1,149,000
Aug 11, 2020
Source: Agent Provided
Pending
$1,149,000
May 28, 2020
Source: Agent Provided
Listed For Sale
$1,149,000

Market trends in Fairfield

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$986K
$28.33KMoM
Sale-to-List Price
103.8%
0.2%MoM
Price per sq ft
$473
$1MoM
Available listings
129
33MoM

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

LGBTQ Local Legal Protections

Frequently asked questions about 44 Wyncum Valley Rd

  • What is 44 Wyncum Valley Rd estimated to be worth?
    Trulia's estimated value for 44 Wyncum Valley Rd in Fairfield, CT is $2,138,500.
  • What is the price history for 44 Wyncum Valley Rd?
    44 Wyncum Valley Rd in Fairfield, CT last sold for $1,425,000 in August 2021.
  • 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 $986K. That is up $28.33K from the prior month.
  • Does 44 Wyncum Valley Rd have air conditioning?
    Yes, 44 Wyncum Valley Rd in Fairfield, CT has air conditioning.
  • Does 44 Wyncum Valley Rd have laundry facilities?
    Yes, 44 Wyncum Valley Rd in Fairfield, CT has laundry facilities.

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Off Market Homes Near 44 Wyncum Valley Rd

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