2866 Chesterfield Drive, Santa Cruz, California 95062, Santa Cruz, 95062 - 2 bed, 2 bath
2866 Chesterfield Drive
Santa Cruz, California 95062
Property Price
SUMMARY
Analysis of 2866 Chesterfield Drive, Santa Cruz, California 95062 reveals a property with a current list price of $1,900,000, which is 4% above the estimated $1,820,774 Fair Market Value. Buyers should carefully evaluate the pricing and consider negotiation opportunities. The property maintains a Excellent Condition Rating (95/100), indicating excellent structural integrity and modern finishes throughout. This turnkey property requires minimal updates and is ready for immediate occupancy. Located in a high-demand neighborhood within the Santa Cruz Unified School District, this asset is categorized as a low-risk, high-reward acquisition suitable for both Buy-and-Hold Investors and Owner-Occupants willing to undertake light renovation work.
Estimated Market Value
Comparable Sales Map
Comparables within 1 miles sold in recently
| Address | Sold Price | Beds | Baths | Sq Ft | $/Sqft | Distance |
|---|---|---|---|---|---|---|
★ 2866 Chesterfield Drive Subject | $1,900,000* List Price | 2 | 2 | 1,280 | $1,422 | - |
A 656 24th Avenue Active | $1,499,000 List Price | 2 | 3 | 1,307 | $1,147 | 0.6 mi |
* Subject property listed price vs sold prices of comps.
Condition Analysis
OVERALL CONDITION SCORE
Property is new construction or fully renovated.
Although originally built in 1933, the property has undergone an extensive recent renovation within the last 5 years. The interior features a fully modernized open-concept kitchen with quartz countertops and new stainless steel appliances, updated bathrooms with contemporary fixtures, new flooring, and recessed lighting throughout. The property shows no signs of deferred maintenance and meets current high-quality design standards.
PROSSTRENGTHS & OPPORTUNITIES
- High Available Lot Utilization
The property has a large lot size, which is more than 4 times of its living area. lot size in square feet = 7013, living area = 1280.
- Prime Coastal Location
Situated just one row back from the surf in the heart of Pleasure Point, this property offers exceptional ocean views and immediate access to world-class surfing and coastal lifestyle amenities.
- Rare Oversized Lot
The 7,000+ sq ft parcel is significantly larger than typical lots in the area and features unique dual-street access from both Chesterfield Drive and Palisades Avenue, offering immense potential for expansion or an ADU.
CONSRISKS & DEFICIENCIES
- MLS Listing Discrepancy
Bedroom count discrepancy between mls listing and other public or private record. mls listing bedroom count = 2, other record bedroom count = 3.
- Limited Interior Square Footage
At 1,280 square feet, the living space is relatively modest for the price point, which may be a constraint for buyers seeking a larger primary residence.
- Vintage Infrastructure
Originally built in 1933, the property may require more intensive maintenance or future upgrades to its foundational systems compared to newer builds in the neighborhood.
About 2866 Chesterfield Drive
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.
Property Details
Public Facts
- Property Type
- Single Family Residence
- Year Built
- 1933
- Lot Size
- 7,013 Sq. Ft.
Interior
- Total Bedrooms
- 2
- Total Bathrooms
- 2 (2 Full, 0 Half)
Exterior & Parking
No exterior & parking available.
Utilities & Misc
- HOA Fee
- $0 / Month
Neighborhood Insights
Santa Cruz Unified Schools
Branciforte Middle School
Grades 6-8 • 2.6 mi
Mission Hill Middle School
Grades 6-8 • 3.6 mi
Harbor High School
Grades 9-12 • 2.4 mi
Sensitive Facilities
No sensitive facilities data found.
Neighborhood Comparison
| Feature | Subject | Average Home | Neighborhood Ranking (50 Listings) |
|---|---|---|---|
| Beds | 2.0 | 3.0 | 29% |
| Baths | 2.0 | 2.0 | 50% |
| Square foot | 1,280 | 1,499 | 33% |
| Lot Size | 7,013 | 5,336 | 73% |
| Price | $1.90M | $1.47M | 69% |
| Price per sq ft | $1.5K | $1.0K | 71% |
| Built year | 1933 | 1960 | 19% |
| HOA | $0 | $0 | 50% |
| Days on market | 119 | 155 | 25% |
Pricing History
Listed for Sale
Feb 26, 2026
$1,900,000
$1,998,000
-5% Price Drop
Initial Listing
Price Change
Dec 19, 2025
$1,998,000
$1,999,000
+0% Price Increase
Initial Listing
Price Change
Nov 8, 2025
$1,999,000
Initial Listing
Sold
Aug 13, 2008
$40,000
Public Record