Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$995,000

  • For Sale
  • Under Contract
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 3,134 Sq. Ft.
  • 2 Car Garage
See This Home
Save This Home
See This Home
Save This Home
This sensational open-concept home is designed for both comfort and style, featuring a gourmet kitchen equipped with high-end appliances, perfect for culinary enthusiasts. The living room boasts a soaring vaulted ceiling, creating an inviting space ideal for entertaining guests. Upstairs, discover three spacious bedrooms, highlighted by an enormous primary suite that includes a private deck-a serene retreat for unwinding. The finished lower level offers a versatile fourth bedroom, suitable for a home office or gym, catering to your lifestyle needs. Outside, the large, private backyard provides an excellent setting for relaxation or hosting gatherings, making this home a perfect blend of elegance and functionality. Enjoy modern living in a space designed for both leisure and entertaining.

Full Property Details for 66 Wynn Wood Dr

General

  • Price: $995,000
  • Taxes: (July 2025-June 2026)
  • Status: Under Contract
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24170000
  • Updated: 5/24/2026
  • Added to Site: 71 day(s) ago

Interior

  • Number of Rooms: 7
  • Interior Features: Security System
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Cooktop, Wall Oven, Refrigerator, Freezer, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom, Upper
  • Bedroom 1: Bedroom, Lower
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom, Upper

Other Rooms

  • Living Room: Living Room - Vaulted Ceiling, Hardwood Floor, Main
  • Family Room: Family Room - Vaulted Ceiling, Half Bath, Hardwood Floor, Main
  • Kitchen: Kitchen - Breakfast Bar, Granite Counters, Hardwood Floor, Main
  • Dining Room: Dining Room - Fireplace, Hardwood Floor, Main
  • Laundry: Upper Level

Exterior

  • Exterior Features: Deck
  • Color: Cream

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking: Under House Garage

Location

  • County: Fairfield
  • Neighborhood: Stratfield
  • Driving Directions: Stratfield Road to Churchill to Wynn Wood

School Information

  • Elementary School: North Stratfield
  • Middle School: Fairfield Woods
  • High School: Fairfield Warde

Community

  • Community Name: Stratfield

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Domestic

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard, Wood
  • Basement Desc.: Full, Partially Finished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,134
  • Above Ground: 3,134 Sq. Ft.
  • Year Built: 1965

Lot Features

  • Lot Size (Acres): 0.64
  • Zoning: A
  • Lot Description: Level Lot

Water Features

  • Water Front Desc.: Beach Rights

Financial Considerations

  • Assessment Amount: $510,090
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 117052

Listed by Higgins Group Real Estate, Lisa Bender

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 66 Wynn Wood Dr —

  • Lisa Bender

    Higgins Group Real Estate

Agent Contact: (203) 521-1181 Office Contact: (203) 254-9000

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 66 Wynn Wood Dr

School District:Fairfield School District
NameGradesDistance
North Stratfield School
190 Putting Green Road, Fairfield, CT 06825
K-50.5 mi
Fairfield Woods Middle School
1115 Fairfield Woods Rd., Fairfield, CT 06824
6-81.4 mi
Fairfield Warde High School
755 Melville Avenue, Fairfield, CT 06825
9-121.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 66 Wynn Wood Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/01/2026
Listed
$995,000
139.76%
MLS
10/10/1996
Sold
$415,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 66 Wynn Wood Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$14,481
2%
$510,090
—
2023
$14,232
1%
$510,090
—
2023
$14,033
1%
$510,090
—
2022
$13,895
1%
$510,090
—
2021
$13,762
-2%
$510,090
-3%
2020
$14,072
—
$525,280
—
2019
$14,072
2%
$525,280
—
2018
$13,846
2%
$525,280
—
2017
$13,563
1%
$525,280
—
2016
$13,368
6%
$525,280
3%
2015
$12,614
2%
$508,830
—
2014
$12,415
2%
$508,830
—
2011
$12,176
—
$508,830
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 66 Wynn Wood Dr

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Higgins Group Real Estate, Lisa Bender

Similar Properties near 66 Wynn Wood Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

153 Woody Ln, Fairfield, CT 06825 - Photo 1
$1,025,000

153 Woody Ln  Fairfield, CT 06825

  • Single Family
  • Active
  • Updated 8 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,300
    Sq. Ft.
Listed by William Raveis Real Estate
43 Green Knolls Ln, Fairfield, CT 06824 - Photo 1
$939,000

43 Green Knolls Ln  Fairfield, CT 06824

  • Single Family
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,361
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
93 Tersana Dr, Easton, CT 06612 - Photo 1
$975,000
Open House

93 Tersana Dr  Easton, CT 06612

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 3,772
    Sq. Ft.
Listed by Keller Williams Realty
223 Sterling Rd, Trumbull, CT 06611 - Photo 1
$999,000

223 Sterling Rd  Trumbull, CT 06611

  • Single Family
  • Active
  • 5
    Beds
  • 4
    Total Baths
  • 4,177
    Sq. Ft.
Listed by Keller Williams Realty

Just Listed near 66 Wynn Wood Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

25 Myron Ave, Bridgeport, CT 06606 - Photo 1 Just Listed
$400,000

25 Myron Ave  Bridgeport, CT 06606

  • Single Family
  • Active
  • Updated 5 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,188
    Sq. Ft.
Listed by The Lewis Team at Coldwell Banker Realty (203) 610-9670
2612 North Ave, Bridgeport, CT 06604 - Photo 1 Just Listed
$319,000

2612 North Ave  #E9  Bridgeport, CT 06604

  • Condo
  • Active
  • Updated 5 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 900
    Sq. Ft.
Listed by The Lage Team at Coldwell Banker Realty (203) 521-7757
189 Wells St, Bridgeport, CT 06606 - Photo 1 Just Listed
$759,500

189 Wells St  Bridgeport, CT 06606

  • Multi-Family
  • Active
  • Updated 2 days ago
  • 6
    Total Beds
Listed by Laura Hardacre (203) 257-1477
283 Salem St, Bridgeport, CT 06606 - Photo 1 Just Listed
$695,000

283 Salem St  Bridgeport, CT 06606

  • Multi-Family
  • Active
  • Updated 3 days ago
  • 5
    Total Beds
Listed by Mark Tavares Realty, LLC

Price Reduced near 66 Wynn Wood Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

2325 E Main St, Bridgeport, CT 06610 - Photo 1 Price Reduced
-$50,000 (-12.53%)
$349,000

2325 E Main St  Bridgeport, CT 06610

  • Commercial
  • Active
Listed by RE/MAX Right Choice
106 Brittin Ave, Bridgeport, CT 06605 - Photo 1 Price Reduced
-$5,100 (-1.21%)
$414,900

106 Brittin Ave  Bridgeport, CT 06605

  • Duplex
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,232
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
150 Beachview Ave, Bridgeport, CT 06605 - Photo 1 Price Reduced
-$19,100 (-5.04%)
$359,900

150 Beachview Ave  #290  Bridgeport, CT 06605

  • Apartment
  • Active
  • Updated 6 hours ago
  • 2
    Beds
  • 1
    Total Bath
  • 1,036
    Sq. Ft.
Listed by Keller Williams Realty
606 Wilmot Ave, Bridgeport, CT 06607 - Photo 1 Price Reduced
-$15,000 (-23.08%)
$50,000

606 Wilmot Ave  #4  Bridgeport, CT 06607

  • Apartment
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 700
    Sq. Ft.
Listed by Bond Realty Group

Recent Sales near 66 Wynn Wood Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

168 Bennett St, Fairfield, CT 06825 - Photo 1 Sold
$976,000

168 Bennett St  Fairfield, CT 06825

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,175
    Sq. Ft.
Listed by Fowler Sakey Team at Coldwell Banker Realty
Sold by William Raveis Real Estate
178 Crest Terrace, Fairfield, CT 06825 - Photo 1 Sold
$1,135,000

178 Crest Terrace  Fairfield, CT 06825

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,524
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by William Pitt Sotheby's Int'l
65 Bailey Rd, Fairfield, CT 06825 - Photo 1 Sold
$893,000

65 Bailey Rd  Fairfield, CT 06825

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 2,888
    Sq. Ft.
Listed by Higgins Group Real Estate
Sold by Compass Connecticut, LLC
89 Random Rd, Fairfield, CT 06825 - Photo 1 Sold
$1,020,000

89 Random Rd  Fairfield, CT 06825

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 1,865
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by William Raveis Real Estate

66 Wynn Wood Drive, Fairfield, CT 06825 (MLS# 24170000) is a Single Family property with 4 bedrooms and 4 full bathrooms. 66 Wynn Wood Drive is currently listed for $995,000 and was received on April 27, 2026. Want to learn more about 66 Wynn Wood Drive? Do you have questions about finding other Single Family real estate for sale in Fairfield? You can browse all Fairfield real estate or contact a Coldwell Banker agent to request more information.

Tour this property