Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$469,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1,478 Sq. Ft.
  • 2 Car Garage
  • Updated 8 hours ago
See This Home
Save This Home
See This Home
Save This Home
Welcome to 68 Pleasant Drive, where a potential in-law suite with its own private entrance offers flexibility for extended family or guests. Hardwood floors, a spacious floor plan, and a convenient Cheshire location create a wonderful place to call home. Sidewalks line the road, adding to the appeal of this walkable setting close to shopping and local restaurants. The large backyard offers plenty of room for outdoor entertaining, gardening, or simply relaxing in privacy. Enjoy space, versatility, and everyday convenience in an established neighborhood. Showings begin tomorrow! NOTE: the square footage reflected in the MLS is based on town assessor records. SELLER BELIEVES it may not accurately represent the home's actual living space. The property offers additional living area beyond what is recorded. Buyers and their agents are encouraged to independently verify total square footage.

Full Property Details for 68 Pleasant Dr

General

  • Price: $469,000
  • Taxes: (July 2026-June 2027)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24214579
  • Updated: Today (10/16/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 10
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Refrigerator

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

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

Other Rooms

  • Living Room: Living Room, Main
  • Kitchen: Kitchen, Main
  • Dining Room: Dining Room, Main
  • Game room: Yes
  • Game Room: Rec/Play Room, Lower
  • Rec Room: Lower

Parking

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

Location

  • County: New Haven
  • Driving Directions: GPS friendly

School Information

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

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Baseboard, Oil
  • Heating Fuel: Oil
  • Water Heater: Other

Utilities

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

Structural Information

  • Architectural Style: Split Level
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Partial
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 1,478
  • Above Ground: 1,478 Sq. Ft.
  • Year Built: 1964

Lot Features

  • Lot Size (Acres): 0.56
  • Zoning: R-20
  • Lot Description: In Subdivision, Treed, Level Lot

Green Features

  • Energy Features: Storm Doors

Financial Considerations

  • Assessment Amount: $251,580
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Property ID: 1081552

Listed by New England Prestige Realty, Abby Breau

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

— 68 Pleasant Dr —

  • Abby Breau

    New England Prestige Realty

Agent Contact: (203) 631-3499 Office Contact: (860) 652-8495

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 Pleasant Dr

School District:Cheshire School District
NameGradesDistance
Highland School, Cheshire, CT
490 Highland Avenue, Cheshire, CT 06410
1-60.4 mi
Dodd Middle School
100 Park Place, Cheshire, CT 06410
7-80.6 mi
Cheshire High School
525 South Main Street, Cheshire, CT 06410
9-121.9 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 68 Pleasant Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/16/2026
Listed
$469,000
174.43%
MLS
3/28/1996
Sold
$170,900
—
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 68 Pleasant Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,482
8%
$251,580
—
2023
$6,908
-8%
$251,580
18%
2023
$7,495
2%
$213,590
—
2022
$7,330
2%
$213,590
—
2021
$7,202
2%
$213,590
—
2020
$7,095
—
$213,590
—
2019
$7,095
12%
$213,590
10%
2018
$6,324
2%
$193,880
—
2017
$6,193
2%
$193,880
—
2016
$6,047
2%
$193,880
—
2015
$5,950
1%
$193,880
—
2014
$5,865
-7%
$193,880
-15%
2011
$6,302
—
$228,350
—
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 68 Pleasant 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 New England Prestige Realty, Abby Breau

Similar Properties near 68 Pleasant Dr

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

16 Deepwood Dr, Cheshire, CT 06410 - Photo 1 Price Reduced
-$10,000 (-2.11%)
$465,000

16 Deepwood Dr  Cheshire, CT 06410

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,566
    Sq. Ft.
Listed by Compass Connecticut, LLC
50 Foxwood Ct, Cheshire, CT 06410 - Photo 1 Just Listed
$465,000

50 Foxwood Ct  Cheshire, CT 06410

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 2,120
    Sq. Ft.
Listed by Cindy Forlenzo (203) 910-4844
6 Plank Rd, Prospect, CT 06712 - Photo 1
$489,900
Open House

6 Plank Rd  Prospect, CT 06712

  • Single Family
  • Active
  • 4
    Beds
  • 3
    Total Baths
  • 1,938
    Sq. Ft.
Listed by Dave Jones Realty, LLC
8 Plank Rd, Prospect, CT 06712 - Photo 1
$489,900

8 Plank Rd  Prospect, CT 06712

  • Single Family
  • Active
  • Updated 8 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,296
    Sq. Ft.
Listed by Better Living Realty, LLC

Just Listed near 68 Pleasant Dr

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

27 Scott Rd, Prospect, CT 06712 - Photo 1 Just Listed
$494,999
Open House

27 Scott Rd  Prospect, CT 06712

  • Single Family
  • Active
  • Updated 8 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,736
    Sq. Ft.
Listed by The Washington Agency
200 Cook Rd, Prospect, CT 06712 - Photo 1 Just Listed
$415,000
Open House

200 Cook Rd  Prospect, CT 06712

  • Single Family
  • Active
  • Updated 8 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,932
    Sq. Ft.
Listed by Regency Real Estate, LLC
44 Cheshire Rd, Prospect, CT 06712 - Photo 1 Just Listed
$159,900

44 Cheshire Rd  Prospect, CT 06712

  • Land Residential
  • Active
  • Updated 1 day ago
  • 4.5
    Acres
Listed by Pavlik Real Estate LLC
20 Byron Rd, Meriden, CT 06451 - Photo 1 Just Listed
$360,000
Open House

20 Byron Rd  Meriden, CT 06451

  • Single Family
  • Active
  • Updated 3 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,000
    Sq. Ft.
Listed by Dawn D'Auria (203) 671-2525

Price Reduced near 68 Pleasant Dr

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

10 Lombard Dr, Prospect, CT 06712 - Photo 1 Price Reduced
-$30,000 (-4.78%)
$598,000

10 Lombard Dr  Prospect, CT 06712

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 4
    Total Baths
  • 2,580
    Sq. Ft.
Listed by William Raveis Real Estate
32 Elliott St, Meriden, CT 06451 - Photo 1 Price Reduced
-$15,000 (-4.23%)
$340,000
Open House

32 Elliott St  Meriden, CT 06451

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,008
    Sq. Ft.
Listed by Dezirae Maldonado (203) 906-4453
517 Swain Ave, Meriden, CT 06450 - Photo 1 Price Reduced
-$10,000 (-2.33%)
$419,900

517 Swain Ave  Meriden, CT 06450

  • Single Family
  • Active
  • Updated 20 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 2,682
    Sq. Ft.
Listed by Brendan Grady (860) 729-8800
34 Fawn Dr, Meriden, CT 06451 - Photo 1 Price Reduced
-$30,000 (-6.38%)
$439,900

34 Fawn Dr  Meriden, CT 06451

  • Single Family
  • Active
  • Updated 4 days ago
  • 5
    Beds
  • 2
    Total Baths
  • 2,150
    Sq. Ft.
Listed by BHGRE Gaetano Marra Homes

Recent Sales near 68 Pleasant Dr

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

129 Pleasant Dr, Cheshire, CT 06410 - Photo 1 Sold
$406,000

129 Pleasant Dr  Cheshire, CT 06410

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,663
    Sq. Ft.
Listed by Berkshire Hathaway NE Prop.
Sold by Great Estates, CT
139 Contour Dr, Cheshire, CT 06410 - Photo 1 Sold
$520,000

139 Contour Dr  Cheshire, CT 06410

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 1,808
    Sq. Ft.
Listed by Re/Max Rise
Sold by Re/Max Rise
424 Cedar Ln, Cheshire, CT 06410 - Photo 1 Sold
$485,000

424 Cedar Ln  Cheshire, CT 06410

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,266
    Sq. Ft.
Listed by Kevin Kennedy and Laureen Kennedy
Sold by Century 21 AllPoints Realty
354 Academy Rd, Cheshire, CT 06410 - Photo 1 Sold
$410,000

354 Academy Rd  Cheshire, CT 06410

  • Single Family
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,678
    Sq. Ft.
Listed by Kayla Magnoli and Courtney Cusano
Sold by The Heritage Group, LLC

68 Pleasant Drive, Cheshire, CT 06410 (MLS# 24214579) is a Single Family property with 4 bedrooms and 3 full bathrooms. 68 Pleasant Drive is currently listed for $469,000 and was received on October 16, 2026. Want to learn more about 68 Pleasant Drive? Do you have questions about finding other Single Family real estate for sale in Cheshire? You can browse all Cheshire real estate or contact a Coldwell Banker agent to request more information.

Tour this property