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$1,998,000

  • For Sale
  • Active
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,280 Sq. Ft.

Next open house:

Open House: 11:00 AM - 1:00 PM

Sunday 1/18 11:00 AM - 1:00 PM

2866 Chesterfield Dr,Santa Cruz, CA 95062

2866 Chesterfield DrSanta CruzCA95062

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Ocean Views from this charming 2 bed / 2 bath home on a rare oversized 7,000 + sq ft lot in the heart of Pleasure Point. Sitting just one row back from the surf, enjoy checking the surf every morning while sipping coffee from your primary suites large upstairs deck. Recently updated with a modern coastal palette, this home features an open-concept kitchen with quartz countertops, new appliances, bright interiors, and effortless indoor-outdoor flow for entertaining. The expansive fully-fenced yard offers endless possibilities like gardens, gatherings, or perhaps room to expand? With a detached storage garage and yard with drive-through access from both Chesterfield Drive and Palisades Avenue, this is one of the largest and most versatile parcels in Pleasure Point. Life at the Point truly doesnt get better than this.

Full Property Details for 2866 Chesterfield Dr

General

  • Price: $1,998,000
  • Status: Active
  • Type: Single Family
  • Source: RE_Infolink
  • MLS ID: ML82027112
  • Updated: 12/20/2025
  • Added to Site: 70 day(s) ago

Interior

  • Fireplace(s): Other
  • Flooring: Laminate, Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Family Room: Separate Family Room

Additional Information

  • Extras: Not Applicable

Parking

  • Parking Features: Drive-Through, Gate / Door Opener, Off-Street Parking, Uncovered Parking

Location

  • Area: Live Oak
  • County: Santa Cruz
  • Cross Streets: E Cliff

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Central Air (Gas/Forced Air)

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Public Utilities

Structural Information

  • Construction: Detached
  • Foundation: Concrete Perimeter
  • Roof: Composition
  • Square Feet: 1,280
  • Year Built: 1933

Lot Features

  • Property View: Neighborhood, Ocean
  • Lot Size (Acres): 0.161
  • Minimum Lot Size: 7013
  • Lot Size (Sq. Ft.): 7,013
  • Zoning: R-1-5-PP
  • Lot Description: Private / Secluded

Listed by Revest Homes, Inc., Ace Woods and eXp Realty of California Inc, Chelsie Wiget

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Listing agents

— 2866 Chesterfield Dr —

  • Ace Woods

    Revest Homes, Inc.

  • Chelsie Wiget

    eXp Realty of California Inc

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 2866 Chesterfield Dr

School Districts:Live Oak Elementary School District, Santa Cruz City High School District
NameGradesDistance
Mission Hill Middle School
425 King Street, Santa Cruz, CA 95060
7-83.6 mi
Harbor High School
300 La Fonda Avenue, Santa Cruz, CA 95062
9-122.3 mi
Soquel High School
401 Soquel San Jose Road, Soquel, CA 95073
9-122.7 mi
Santa Cruz High School
415 Walnut Avenue, Santa Cruz, CA 95060
9-123.3 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 2866 Chesterfield Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/18/2025
Price Reduced
$1,998,000
-0.05%
MLS
11/08/2025
Listed
$1,999,000
—
MLS
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 2866 Chesterfield Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$25,806
832%
$2,136,901
1788%
2023
$2,769
4%
$113,170
2%
2022
$2,671
8%
$110,952
2%
2021
$2,479
2%
$108,776
1%
2020
$2,434
2%
$107,661
2%
2019
$2,385
3%
$105,549
2%
2018
$2,325
3%
$103,480
2%
2017
$2,268
1%
$101,453
2%
2016
$2,235
7%
$99,463
2%
2015
$2,092
2%
$97,969
2%
2014
$2,045
—
$96,049
—
2013
$2,044
—
$95,614
—
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.

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*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

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Listed by Revest Homes, Inc., Ace Woods and eXp Realty of California Inc, Chelsie Wiget

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2866 Chesterfield Dr, Santa Cruz, CA 95062 (MLS# ML82027112) is a Single Family property with 2 bedrooms and 2 full bathrooms. 2866 Chesterfield Dr is currently listed for $1,998,000 and was received on November 08, 2025. Want to learn more about 2866 Chesterfield Dr? Do you have questions about finding other Single Family real estate for sale in Live Oak? You can browse all Live Oak real estate or contact a Coldwell Banker agent to request more information.

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