Harboring The Good Life

Dana Point

I think most stories are best started at the beginning, and Dana Point may have one of the best beginnings in all of Orange County, or at least, one of the oldest.


The tale picks up in Boston in 1834 in which the town’s namesake – Richard Henry Dana – boards a ship bound for California. In his epic tale, “Two Years Before the Mast” (truly, a must-read for anyone who lives here), he details his journey and his eventual arrival in California - at that point, an almost mystical destination in the national psyche.


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Dana Point Real Estate Statistics

Average Price $1.6M
Lowest Price $1.6K
Highest Price $21M
Total Listings 231
Avg. Days On Market 148
Avg. Price/SQFT $494

Property Types (active listings)


True to form, he is enchanted with California’s coastal landscapes (sound familiar, coastal property hunter?) and spends some time anchored in the place now known as Dana Point. Dana considered the area “the most beautiful along the California coastline.”

If California ever becomes a prosperous country, this bay will be the centre of its prosperity.” - Richard Henry Dana

Here are some excerpts from his journal:

“San Juan is the only romantic spot on the coast. The country here for several miles is high table-land, running boldly to the shore, and breaking off in a steep cliff, at the foot of which the waters of the Pacific are constantly dashing... we strolled about, picking up shells, and following the sea where it tumbled in, roaring and spouting, among the crevices of the great rocks. What a sight, thought I, must this be in a southeaster! … there was a grandeur in everything around, which gave a solemnity to the scene, a silence and solitariness which affected every part! Not a human being but ourselves for miles, and no sound heard but the pulsations of the great Pacific! and the great steep hill rising like a wall, and cutting us off from all the world, but the '"'world of waters'"'!""

“I separated myself from the rest, and sat down on a rock, just where the sea ran in and formed a fine spouting horn. Compared with the plain, dull sand-beach of the rest of the coast, this grandeur was as refreshing as a great rock in a weary land. It was almost the first time that I had been positively alone-- free from the sense that human beings were at my elbow, if not talking with me-- since I had left home. My better nature returned strong upon me. Everything was in accordance with my state of feeling, and I experienced a glow of pleasure at finding that what of poetry and romance I ever had in me had not been entirely deadened by the laborious life, with its paltry, vulgar associations, which I had been leading. Nearly an hour did I sit, almost lost in the luxury of this entire new scene of the play in which I had been so long acting, when I was aroused by the distant shouts of my companions, and saw that they were collecting together, as the agent had made his appearance, on his way back to our boat.”

The place where Dana sat and marveled is more or less still there today – take a visit to the Headlands and sit one evening when the surf is breaking at sunset and you can feel that same grandeur.

Development in Dana Point didn’t begin in earnest until almost 100 years later, though, when the Dana Point Syndicate was formed in 1925 by real estate developer Sidney H. Woodruff, Harry Chandler & General M. H. Sherman for the purpose of purchasing approximately 1,400 acres of land which include what is now the Headlands, the Strand, and Lantern Village. Woodruff had planned on building out a Mediterranean-like town that followed the contours of the coastal hills with modern day amenities like sewers, storm drains, and tree-lined paved streets. Every street in the Lantern District was named for the lanterns which dotted the roads -- Ruby Lantern, Crystal Lantern, Blue Lantern, Green Lantern, and on. The lanterns at the end of each street had a light atop their posts that was the same color as the name of the street - thus a traveler roaming in the foggy evening would always know what street she was on.

Thirty-five Woodruff homes were built and most still exist today, but his coastal town vision was cut short after the arrival of the Great Depression in 1929. What he did leave behind was a legacy of coastal California architecture, both built & dreamed.

“Here are beautiful Palisades, golden beaches, a charming Stillwater bay, splendid soil, an incomparable climate and splendid Water Supply” -- S. H. Woodruff promotion, 1927

Incorporated in 1989, the City of Dana Point now encompasses Monarch Beach to the north, Capistrano Beach to the south, Lantern Village and the Dana Hills & Del Obispo areas to the east. Homes range from tidy coastal bungalows to the multi-million dollar estate homes in the Strand, Monarch Bay, & Ritz Cove.

For those that are fortunate enough to own investment real estate, and are interested in multifamily real estate, Dana Point has a nice range of multifamily properties ranging from duplexes up to 20+ unit complexes.

If you are interested in exploring Dana Point’s myriad neighborhoods to find a home for yourself, or starting and/or building a portfolio of investment properties, give Jesse a call today at (949) 292-9786.


Dana Point Listings

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Dana Point Living

  • Dana Point is a coastal town located just south of Laguna Beach and north of San Clemente.
  • Dana Point is home to the Dana Point Harbor, epic surfing spots, gorgeous beaches, beachside concert events, parks - so much!
  • DP is known for its rich history as a working coastal town that is now part of California's iconic history.

Headlands Dana Point Sunset

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