Recently Viewed Properties
See This Home
Save This Listing
Close

$1,225,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 4,682 Sq. Ft.
  • 3 Car Garage
See This Home
Save This Home
See This Home
Save This Home
This magnificent Woodbury colonial, adjacent to 42 acres of open space, offers an unparalleled blend of elegance and tranquility. Surrounded by hiking trails, park like grounds and a serene brook. A light filled interior with soaring nine foot ceilings, graceful arches and an open flowing floor plan. The wraparound mahogany deck invites you to relax and take in the peace and quiet. The back patio, crafted with premium ipe decking, features tiered rock walls and a circular fire pit-perfect for entertaining or quiet evenings under the stars. Designed with quality and comfort in mind this home boasts I-beam construction, two wells, enhanced insulation, and durable HardiePlank siding, ideal for those who value sustainable, low maintenance living. Turn off the outside noise and rest assure this sanctuary will welcome you home with open arms.

Full Property Details for 68 Whittlesey Rd

General

  • Sold For: $1,225,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24130861
  • Added to Site: 107 day(s) ago

Interior

  • Number of Rooms: 11
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Cook Top, Wall Oven, Subzero, Dishwasher, Wine Chiller

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4
  • Full Bath: Hardwood Floor, Main

Bedrooms

  • Total Bedrooms: 4
  • Primary Suite: Walk-In Closet, Hardwood Floor, 18 x 16, Upper
  • Bedroom 1: Bedroom - Hardwood Floor, 13 x 12, Upper
  • Bedroom 2: Bedroom - Hardwood Floor, 13 x 12, Upper
  • Bedroom 3: Bedroom - Hardwood Floor, 14 x 13, Upper

Other Rooms

  • Living Room: Living Room - 9 ft+ Ceilings, French Doors, Hardwood Floor, 14 x 18, Main
  • Great Room: Great Room - Wet Bar, Hardwood Floor, 22 x 30, Upper
  • Family Room: Family Room - 9 ft+ Ceilings, Built-Ins, Ceiling Fan, Fireplace, Hardwood Floor, 22 x 16, Main
  • Kitchen: Kitchen - 9 ft+ Ceilings, Tile Floor, 18 x 21, Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, Hardwood Floor, 14 x 15, Main
  • Game room: Yes
  • Game Room: Rec/Play Room, Lower
  • Rec Room: Lower
  • Laundry: Upper Level
  • Other Room 1: Other - 9 ft+ Ceilings, Hardwood Floor, Main

Exterior

  • Exterior Features: Wrap Around Deck, Covered Deck, Stone Wall, French Doors, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Parking: Attached Garage

Location

  • County: Litchfield
  • Neighborhood: Good Hill
  • Driving Directions: Route 317 to Whittlesey

School Information

  • Elementary School: Per Board of Ed
  • High School: Nonnewaug

Community

  • Community Name: Good Hill

Heating & Cooling

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

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Hardie Board
  • Basement Desc.: Full
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 4,682
  • Above Ground: 4,682 Sq. Ft.
  • Year Built: 2006

Lot Features

  • Lot Size (Acres): 3
  • Zoning: OS100
  • Lot Description: Lightly Wooded, On Cul-De-Sac, Rolling

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Brook

Green Features

  • Energy Features: Thermopane Windows

Financial Considerations

  • Assessment Amount: $581,140
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 934919

Listed by William Pitt Sotheby's Int'l, Michael Caporizzo and William Pitt Sotheby's Int'l, Erin Caporizzo
Sold by William Pitt Sotheby's Int'l, Lori Belter

Listing agents

— 68 Whittlesey Rd —

  • Michael Caporizzo

    William Pitt Sotheby's Int'l

  • Erin Caporizzo

    William Pitt Sotheby's Int'l

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 68 Whittlesey Rd

School District:Regional School District 14
NameGradesDistance
Mitchell Elementary School
14 School Street, Woodbury, CT 06798
PK-52.1 mi
Bethlehem Elementary School
92 East Street, Bethlehem, CT 06751
PK-56.1 mi
Woodbury Middle School
67 Washington Avenue, Woodbury, CT 06798
6-81.9 mi
Nonnewaug High School
5 Minortown Road, Woodbury, CT 06798
9-123 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 68 Whittlesey Rd

Date
Details
Price
Change
Source
11/16/2025
Sold
$1,225,000
4.26%
MLS
10/03/2025
Listed
$1,175,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by William Pitt Sotheby's Int'l, Michael Caporizzo and William Pitt Sotheby's Int'l, Erin Caporizzo
Sold by William Pitt Sotheby's Int'l, Lori Belter

Similar Properties near 68 Whittlesey Rd

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

24 Hickory Ln, Roxbury, CT 06783 - Photo 1
$1,155,000

24 Hickory Ln  Roxbury, CT 06783

  • Single Family
  • Active
  • 4
    Beds
  • 3
    Total Baths
  • 3,340
    Sq. Ft.
Listed by Sidney Nazario (347) 387-5633
373 Transylvania Rd, Woodbury, CT 06798 - Photo 1
$1,275,000

373 Transylvania Rd  Woodbury, CT 06798

  • Single Family
  • Active
  • 3
    Beds
  • 5
    Total Baths
  • 4,059
    Sq. Ft.
Listed by William Raveis Real Estate
27 Middle Quarter Rd, Woodbury, CT 06798 - Photo 1
$1,100,000

27 Middle Quarter Rd  Woodbury, CT 06798

  • Single Family
  • Active
  • 3
    Beds
  • 3
    Total Baths
  • 2,042
    Sq. Ft.
Listed by Drakeley Real Estate, Inc.
55 Country Woods Ln, Southbury, CT 06488 - Photo 1 Just Listed
$1,150,000

55 Country Woods Ln  Southbury, CT 06488

  • Single Family
  • Active
  • Updated 2 days ago
  • 5
    Beds
  • 5
    Total Baths
  • 5,236
    Sq. Ft.
Listed by William Raveis Real Estate

Just Listed near 68 Whittlesey Rd

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

9 Gettysburg Rd, Southbury, CT 06488 - Photo 1 Just Listed
$630,000
Open House

9 Gettysburg Rd  #9  Southbury, CT 06488

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,094
    Sq. Ft.
Listed by Berkshire Hathaway NE Prop.
55 Country Woods Ln, Southbury, CT 06488 - Photo 1 Just Listed
$1,150,000

55 Country Woods Ln  Southbury, CT 06488

  • Single Family
  • Active
  • Updated 2 days ago
  • 5
    Beds
  • 5
    Total Baths
  • 5,236
    Sq. Ft.
Listed by William Raveis Real Estate
761 Heritage Vlg, Southbury, CT 06488 - Photo 1 Just Listed
$339,900
Open House

761 Heritage Vlg  #D  Southbury, CT 06488

  • Condo
  • Active
  • Updated 2 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,063
    Sq. Ft.
Listed by BHGRE Gaetano Marra Homes
61 Sandy Hill Rd, Middlebury, CT 06762 - Photo 1 Just Listed
$529,900

61 Sandy Hill Rd  Middlebury, CT 06762

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,811
    Sq. Ft.
Listed by William Raveis Real Estate

Price Reduced near 68 Whittlesey Rd

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

1008 Heritage Vlg, Southbury, CT 06488 - Photo 1 Price Reduced
-$3,900 (-1%)
$385,000
Open House

1008 Heritage Vlg  #B  Southbury, CT 06488

  • Townhouse
  • Active
  • Updated 5 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,432
    Sq. Ft.
Listed by Dave Jones Realty, LLC
740 Heritage Vlg, Southbury, CT 06488 - Photo 1 Price Reduced
-$6,000 (-1.45%)
$409,000
Open House

740 Heritage Vlg  #B  Southbury, CT 06488

  • Condo
  • Active
  • Updated 2 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,432
    Sq. Ft.
Listed by William Raveis Real Estate
825 Heritage Vlg, Southbury, CT 06488 - Photo 1 Price Reduced
-$10,000 (-3.45%)
$279,900

825 Heritage Vlg  #B  Southbury, CT 06488

  • Townhouse
  • Active
  • Updated 19 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,365
    Sq. Ft.
Listed by Keller Williams Realty
1449 Old Waterbury Rd, Southbury, CT 06488 - Photo 1 Price Reduced
-$10,000 (-7.15%)
$129,900

1449 Old Waterbury Rd  #307  Southbury, CT 06488

  • Commercial
  • Active
Listed by Davis Owen Real Estate

Recent Sales near 68 Whittlesey Rd

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

30 Hickory Ln, Roxbury, CT 06783 - Photo 1 Sold
$1,400,000

30 Hickory Ln  Roxbury, CT 06783

  • Single Family
  • Closed
  • 4
    Beds
  • 6
    Total Baths
  • 4,721
    Sq. Ft.
Listed by W. Raveis Lifestyles Realty
Sold by Re/Max Rise
53 Transylvania Rd, Roxbury, CT 06783 - Photo 1 Sold
$1,200,000

53 Transylvania Rd  Roxbury, CT 06783

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 3,920
    Sq. Ft.
Listed by W. Raveis Lifestyles Realty
Sold by Town & Country Realty and Design, LLC
158 Painter Hill Rd, Roxbury, CT 06783 - Photo 1 Sold
$1,195,000

158 Painter Hill Rd  Roxbury, CT 06783

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,793
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
Sold by William Pitt Sotheby's Int'l
88 Hemlock Rd, Roxbury, CT 06783 - Photo 1 Sold
$1,400,000

88 Hemlock Rd  Roxbury, CT 06783

  • Single Family
  • Closed
  • 2
    Beds
  • 3
    Total Baths
  • 3,389
    Sq. Ft.
Listed by Klemm Real Estate Inc
Sold by Klemm Real Estate Inc

68 Whittlesey Road, Woodbury, CT 06798 (MLS# 24130861) is a Single Family property that was sold at $1,225,000 on November 16, 2025. Want to learn more about 68 Whittlesey Road? Do you have questions about finding other Single Family real estate for sale in Woodbury? You can browse all Woodbury real estate or contact a Coldwell Banker agent to request more information.