Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$2,395,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 3,384 Sq. Ft.
  • 2 Car Garage
  • Updated 2 hours ago

Next open house:

Open House: 1:00 PM - 3:00 PM

Saturday 5/9 1:00 PM - 3:00 PM

27 Point O Woods Road South,Darien, CT 06820

27 Point O Woods Road SouthDarienCT06820

Get directions
See This Home
Save This Home
See This Home
Save This Home
Tucked away on a quiet cul-de-sac in the sought after Ox-Ridge school district, this beautifully updated 4 Bedroom, 2.5 Bath Colonial offers an exceptional blend of timeless elegance and modern sophistication. Thoughtfully designed for both refined living and effortless entertaining, the home features a stunning renovated kitchen and spa inspired baths, all finished with quality craftsmanship and attention to detail. The large deck is perfectly designed for effortless seasonal entertaining, offering an ideal setting for everything from summer gatherings to cozy fall evenings outdoors. Sunlight pours through expansive windows, illuminating the home's spacious, well-proportioned interiors and creating a warm, inviting ambiance throughout. The finished walk-out lower level adds a versatile extension of flexible living space-perfect as a playroom, media lounge, or home gym. Ideally located just moments from town, shops, and everyday conveniences, this home combines the serenity of a private setting with the ease of in-town living. Complete with a two-car garage, this is a rare opportunity to enjoy comfort, style, and convenience in one exceptional offering.

Full Property Details for 27 Point O Woods Rd S

General

  • Price: $2,395,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24171930
  • Updated: 5/7/2026
  • Added to Site: 3 day(s) ago

Interior

  • Number of Rooms: 8
  • Rooms/Areas: Foyer, Laundry Room
  • Interior Features: Auto Garage Door Opener
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Oven/Range, Microwave, Refrigerator, Icemaker, Dishwasher, Washer, Electric Dryer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Suite: Full Bath, Hardwood Floor, Upper
  • Bedroom 1: Bedroom - Hardwood Floor, Upper
  • Bedroom 2: Bedroom - Hardwood Floor, Upper
  • Bedroom 3: Bedroom - Full Bath, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, Main
  • Family Room: Family Room - Fireplace, Sliders, Hardwood Floor, Main
  • Kitchen: Kitchen - Remodeled, Hardwood Floor, Main
  • Dining Room: Dining Room - Hardwood Floor, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Sliders, Lower
  • Rec Room: Sliders, Lower
  • Laundry: Main Level

Exterior

  • Exterior Features: Underground Utilities, Deck, Gutters
  • Color: White

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Driving Directions: Point O Woods Road to Point O Woods South

School Information

  • Elementary School: Ox Ridge
  • Middle School: Middlesex
  • High School: Darien

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, 65 Gallon Tank

Utilities

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

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding, Brick
  • Basement Desc.: Full, Partially Finished, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,384
  • Above Ground: 2,784 Sq. Ft.
  • Below Ground: 600 Sq. Ft.
  • Year Built: 1983

Lot Features

  • Lot Size (Acres): 0.52
  • Zoning: R12
  • Lot Description: On Cul-De-Sac, Professionally Landscaped

Water Features

  • Water Front Desc.: Beach Rights

Financial Considerations

  • Assessment Amount: $1,137,990
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 104073

Listed by Houlihan Lawrence, Caroline Hanley

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

— 27 Point O Woods Rd S —

  • Caroline Hanley

    Houlihan Lawrence

Agent Contact: (917) 699-9713 Office Contact: (203) 655-8238

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 27 Point O Woods Rd S

School District:Darien School District
NameGradesDistance
Ox Ridge Elementary School
395 Mansfield Avenue, Darien, CT 06820
K-51.7 mi
Middlesex Middle School
204 Hollow Tree Ridge Road, Darien, CT 06820
6-82.3 mi
Darien High School
80 High School Lane, Darien, CT 06820
9-121.7 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 27 Point O Woods Rd S Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/04/2026
Listed
$2,395,000
78.07%
MLS
6/01/2007
Sold
$1,345,000
—
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 27 Point O Woods Rd S

Year
Property Taxes
Change
Tax Assessment
Change
2025
$17,616
5%
$1,137,990
—
2023
$16,717
9%
$1,137,990
31%
2023
$15,345
2%
$871,360
—
2022
$15,014
2%
$871,360
—
2021
$14,674
3%
$871,360
—
2020
$14,229
-1%
$871,360
—
2019
$14,351
3%
$871,360
—
2018
$13,963
—
$868,350
—
2017
$14,033
2%
$868,350
—
2016
$13,694
3%
$868,350
—
2015
$13,329
2%
$868,350
—
2014
$13,034
9%
$868,350
-4%
2012
$11,943
—
$906,850
—
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 27 Point O Woods Rd S

$
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 Houlihan Lawrence, Caroline Hanley

Similar Properties near 27 Point O Woods Rd S

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

20 Roton Ave, Norwalk, CT 06853 - Photo 1 Just Listed
$2,450,000
Open House

20 Roton Ave  Norwalk, CT 06853

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 5
    Total Baths
  • 4,006
    Sq. Ft.
Listed by William Raveis Real Estate
27 Crest Rd, Norwalk, CT 06853 - Photo 1 Just Listed
$2,450,000
Open House

27 Crest Rd  Norwalk, CT 06853

  • Single Family
  • Active
  • Updated 5 hours ago
  • 5
    Beds
  • 4
    Total Baths
  • 3,750
    Sq. Ft.
Listed by Compass Connecticut, LLC
19 Chester Rd, Darien, CT 06820 - Photo 1 Just Listed
$2,225,000
Open House

19 Chester Rd  Darien, CT 06820

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,264
    Sq. Ft.
Listed by Houlihan Lawrence
39 Wedgemere Rd, Stamford, CT 06905 - Photo 1
$2,395,000

39 Wedgemere Rd  Stamford, CT 06905

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 6,920
    Sq. Ft.
Listed by Houlihan Lawrence

Just Listed near 27 Point O Woods Rd S

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

128 1/2 Ponus Ave, Norwalk, CT 06850 - Photo 1 Just Listed
$375,000

128 1/2 Ponus Ave  Norwalk, CT 06850

  • Land Residential
  • Active
  • Updated 4 days ago
  • 0.8
    Acres
Listed by Kelly Higgins Team (203) 650-3483
20 Brushwood Rd, Stamford, CT 06903 - Photo 1 Just Listed
$1,850,000

20 Brushwood Rd  Stamford, CT 06903

  • Single Family
  • Active
  • Updated 4 days ago
  • 6
    Beds
  • 4
    Total Baths
  • 4,716
    Sq. Ft.
Listed by Barbara Zaccagnini (203) 618-0172 and Coldwell Banker Realty
1458 Bedford St, Stamford, CT 06905 - Photo 1 Just Listed
$12,000

1458 Bedford St  Stamford, CT 06905

  • Commercial Lease
  • Active
Listed by The Rosato Team (203) 622-4000
71 Strawberry Hill Ave, Stamford, CT 06902 - Photo 1 Just Listed
$259,900

71 Strawberry Hill Ave  #221  Stamford, CT 06902

  • Condo
  • Active
  • Updated 1 day ago
  • 2
    Beds
  • 1
    Total Bath
  • 875
    Sq. Ft.
Listed by Timothy Piedmont (203) 273-9880

Price Reduced near 27 Point O Woods Rd S

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

125 Oaklawn Ave, Stamford, CT 06905 - Photo 1 Price Reduced
-$51,000 (-6.8%)
$699,000

125 Oaklawn Ave  Stamford, CT 06905

  • Single Family
  • Active
  • Updated 7 minutes ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,164
    Sq. Ft.
Listed by Compass Connecticut, LLC
51 Schuyler Ave, Stamford, CT 06902 - Photo 1 Price Reduced
-$15,000 (-4.62%)
$310,000
Open House

51 Schuyler Ave  #APT 5C  Stamford, CT 06902

  • Apartment
  • Active
  • Updated 2 days ago
  • 1
    Bed
  • 1
    Total Bath
  • 788
    Sq. Ft.
Listed by Keller Williams Prestige Prop.
19 Burwood Ave, Stamford, CT 06902 - Photo 1 Price Reduced
-$40,000 (-4.21%)
$910,000

19 Burwood Ave  Stamford, CT 06902

  • Single Family
  • Active
  • Updated 1 hour ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,608
    Sq. Ft.
Listed by Via Real Estate LLC
23 Ryan St, Stamford, CT 06907 - Photo 1 Price Reduced
-$950 (-29.23%)
$2,300

23 Ryan St  Stamford, CT 06907

  • Commercial Lease
  • Active
Listed by Serhant Connecticut, LLC

Recent Sales near 27 Point O Woods Rd S

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

13 Wakeman Rd, Darien, CT 06820 - Photo 1 Sold
$2,105,000

13 Wakeman Rd  Darien, CT 06820

  • Single Family
  • Closed
  • Updated 2 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,959
    Sq. Ft.
Listed by Compass Connecticut, LLC and Houlihan Lawrence
Sold by Brown Harris Stevens
12 Dellwood Rd, Darien, CT 06820 - Photo 1 Sold
$2,300,000

12 Dellwood Rd  Darien, CT 06820

  • Single Family
  • Closed
  • 5
    Beds
  • 6
    Total Baths
  • 4,672
    Sq. Ft.
Listed by Lori Printz
Sold by Houlihan Lawrence
209 Rowayton Ave, Norwalk, CT 06853 - Photo 1 Sold
$2,640,000

209 Rowayton Ave  Norwalk, CT 06853

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,068
    Sq. Ft.
Listed by Brown Harris Stevens
Sold by Compass Connecticut, LLC
181 Highland Ave, Norwalk, CT 06853 - Photo 1 Sold
$2,540,000

181 Highland Ave  Norwalk, CT 06853

  • Single Family
  • Closed
  • 5
    Beds
  • 3
    Total Baths
  • 4,250
    Sq. Ft.
Listed by Mary Petro Noonan
Sold by Houlihan Lawrence

27 Point O Woods Road South, Darien, CT 06820 (MLS# 24171930) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 27 Point O Woods Road South is currently listed for $2,395,000 and was received on May 04, 2026. Want to learn more about 27 Point O Woods Road South? Do you have questions about finding other Single Family real estate for sale in Darien? You can browse all Darien real estate or contact a Coldwell Banker agent to request more information.

Tour this property