Perched on one of Rolling Hills Ranch's premier view lots, this one-of-a-kind residence captures sweeping ocean views, breathtaking sunsets, and the cool coastal breezes that define Southern California living. Fully updated and elegantly curated, every detail has been thoughtfully selected to create a home that is both sophisticated and inviting. A grand entry with soaring ceilings and abundant natural light sets the tone, while expansive living spaces flow effortlessly throughout. The beautifully renovated kitchen features designer finishes, a large center island, and seamless connection to the family room and outdoor living areas, creating the perfect setting for everyday living and entertaining. The luxurious primary suite has been transformed into a true retreat, highlighted by a stunning spa-inspired bathroom with premium materials and timeless design. Throughout the home, you'll find refined finishes, quality craftsmanship, and a cohesive aesthetic rarely found in today's market. Step outside to your private backyard sanctuary overlooking rolling hills and distant ocean views. Whether enjoying morning coffee, sunset gatherings, or the refreshing afternoon breeze, the setting is simply unforgettable. Located within a highly sought-after community offering top-rated schools, resort-style amenities, parks, trails, shopping, and dining, this turnkey home delivers an exceptional combination of luxury, comfort, and lifestyle. Rarely does a home offer this level of design, updating, views, and setting. A truly exceptional opportunity.
Single-familyProperty Type
2004Year Built
7,017 sq ftLot Size
$499Price/Sq.Ft.
$199/moHOA Dues
2 garage spacesParking
Listed by Adam King•DRE #02218555• NewTown Real Estate
•619-818-2814 (agent)
•adam@newtowngroupre.com (agent)
Bought with Daniela F.P Flores Pedroza•DRE #02213042• ShoppingSDHouses
Est. $7,609 per month, based on comparable rentals
Sale and tax history for 2421 Crooked Trail Rd
Sale History
Tax History
Date
Event
Price
SDMLS #260014629
Sep 18, 2026
Sold
$1,940,000
$499/sq ft
Aug 13, 2026
Pending
—
Jun 17, 2026
Listed
$1,976,000
$508/sq ft
Jun 16, 2026
Coming Soon
$1,976,000
$508/sq ft
CRMLS #PTP2105077
Aug 30, 2021
Sold
$1,210,000
$311/sq ft
Jul 29, 2021
Pending
—
Jul 28, 2021
Price Changed
$1,225,000
$315/sq ft
Jul 22, 2021
Listed
$1,150,000
$296/sq ft
Jul 20, 2021
Coming Soon
$1,150,000
$296/sq ft
Welcome Home to this stunning former Model Home in Rolling Hills Ranch. This home is fabulous and has been lovingly maintained by the owners. 5 bedrooms ( full bed and bath downstairs) 4 baths, office downstairs could be a 6th bedroom. This home features high ceilings, beautiful travertine and wood flooring throughout the home, a gourmet cooks kitchen with center island, Viking 6 burner gas cooktop with hood, Kitchen Aid dishwasher. microwave & wall oven. Separate Coffee/Wine Bar with Kitchen Aid wine refrigerator. Two fireplaces, one in the family room and a dual sided fireplace in the living room/ office. This is a great entertaining home with lots of room to spread out. There are no neighbors behind you which adds to the privacy and serenity of this home that has views to Point Loma and Downtown San Diego. Master Bedroom has a cozy balcony where you san sip your wine and watch the amazing sunsets! The master suite is amazing with a large vanity area, spa tub and large walk-in closet. This home also features PAID SOLAR, a huge media room upstairs that is great for those movies nights. Enjoy the ocean breezes from the beautiful backyard complete with built-in BBQ area with a brand new Kitchen Aid Stainless BBQ. Walking distance to Thurgood Marshall Elementary, parks and community pools! THIS HOME HAS NO MELLO ROOS and low HOA fees. This is a must see home, it will not last long!
SDMLS #1
Sep 5, 2008
Price Changed
$649,900
$167/sq ft
CRMLS #88036568
Sep 5, 2008
Sold
$640,000
$165/sq ft
May 19, 2008
Listed
$649,900
$167/sq ft
SDMLS #78087694
Apr 23, 2008
Listing Removed
—
Nov 2, 2007
Listed
$799,000
$206/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$15,084 (+3.7%)
$654,870 + $654,870
$1,309,740
2024
$14,552 (+1.6%)
$642,030 + $642,030
$1,284,060
2023
$14,316 (+2.9%)
$629,442 + $629,442
$1,258,884
2022
$13,916 (+60.8%)
$617,100 + $617,100
$1,234,200
2021
$8,655 (+2.4%)
$605,000 + $605,000
$1,210,000
2020
$8,454 (+2.7%)
$297,412 + $463,967
$761,379
2019
$8,228 (+1.4%)
$294,363 + $459,210
$753,573
2018
$8,111 (+1.0%)
$288,592 + $450,206
$738,798
2017
$8,035 (+3.0%)
$277,387 + $432,725
$710,112
2016
$7,804 (+1.3%)
$277,387 + $432,725
$710,112
2015
$7,703 (+5.4%)
$271,949 + $424,241
$696,190
2014
$7,309 (+15.6%)
$253,000 + $397,000
$650,000
2013
$6,323 (−0.3%)
$253,000 + $397,000
$650,000
2012
$6,345 (−13.1%)
$218,000 + $340,000
$558,000
2011
$7,299 (+0.9%)
$218,000 + $340,000
$558,000
2010
$7,231
$251,285 + $392,004
$643,289
2009
$7,237 (−43.7%)
$249,407 + $389,075
$638,482
2008
$12,848
$250,000 + $390,000
$640,000
Public record
Public record
Permits
Beds
6
Baths
4
Stories
—
Lot width
—
Lot depth
—
Lot size
7,017 Sq. Ft.
Year renovated
2004
Sq. Ft.
3,887
Year built
2004
Style
Single Family Residential
County
San Diego County
APN
5957242700
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Sep 25, 2026.
Nov 4, 2002 • Final
Residential new construction
Work on a single-family home and garage.
New construction
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Appliances: Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer, Built-In Range, Double Oven, Freezer, Gas Oven, Vented Exhaust Fan, Gas Range, Gas Cooktop, Range Hood, Water Purifier
Has Fireplace
# of Fireplaces: 2
Fireplace Features: Gas, Family Room, Living Room
Room Information
Laundry Features: Washer Hookup
Exterior
Exterior Features
Exterior Features: Barbecue
Fencing: Full, Gate, Wrought Iron, Wood
Pool Information
Pool Features: Community
Has Spa/Hot Tub
Spa Features: Above Ground, Heated
Building Information
Sq. Ft.: 3887.0
# of Stories Total: 2
Construction Materials: Stone, Stucco
Property Information
Property Type: Residential
Property Sub Type: Single Family Residence
Raw Mls Property Sub Type: Detached
Property Condition: Updated/Remodeled
Lot Information
Lot Size : 7,500-10,889 SF
Lot Size Units: Acres
Utilities
Utility Information
Water Source: Public
Utilities: Sewer Connected, Electricity Available, Natural Gas Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Connected, Underground Utilities, Water Connected
Location
HOA Information
Has Homeowners Association
Association Amenities: Playground, Sport Court, Pool
Association Fee: $199
Association Fee Frequency: Monthly
Derived Association Fee (Monthly): $199
Association Fee Includes: Maintenance Grounds
Schools Information
Elementary School District: Chula Vista Elementary District
Middle Or Junior School District: Sweetwater Union High School Dis
High School District: Sweetwater Union High School Dis
Location Information
Subdivision Name: Rolling Hills (RHH)
Public facts
Beds: 6
Baths: 4.0
Sq. Ft.: 3,887
Stories: —
Lot Size: 7,017 square feet
Style: Single Family Residential
Year Built: 2004
Year Renovated: 2004
County: San Diego County
APN: 5957242700
Home facts updated by county records on Sep 25, 2026
Other
Listing Information
List AOR: San Diego Association of REALTOR
Around this home
Schools
Marshall (Thurgood) Elementary School
Public K-6 • Assigned • 0.2mi
9/10
Eastlake Middle School
Public 7-8 • Assigned • 1.2mi
6/10
Eastlake High School
Public 9-12 • Assigned • 1.5mi
10/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
5/10 Fire Factor
4% chance of being in a wildfire in next 30 years
4/10 Heat Factor
7 days above 94° expected this year, 19 days in 30 years
1/10 Wind Factor
Minimal risk of severe winds over next 30 years
3/10 Air Factor
3 unhealthy days expected this year, 3 days in 30 years
Provided by First Street
Historical weather
Chula Vista, CA • 91914
Average low and high temperatures (°F)
68
47
70
50
72
52
70
52
71
56
76
59
80
62
82
63
81
64
78
57
71
51
70
49
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
87/ 100
Very good sunlight
Sunscore
This home receives average direct sun exposure in Chula Vista. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.4 hrs
6.3 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$1.80M – $2.18M
Reach more buyers when you sell with Redfin. Plus, you'll save $18,934 in fees.