One of the most frequent questions in today’s housing market is “should I buy or should I rent?” Such a question is subject to the condition of the housing market you’re shopping in, unemployment, foreclosure environment, mortgage rates and so much more. But, believe it or not, even in this recession-strung economy, some people are still able to afford multi-million dollar homes, which spawned the question of whether the same rent vs. buy conundrum applied to someone who is able to spend five figures each month for a roof over their head.

We decided to find some of the country’s most expensive rentals on the market and do an apples-to-apples comparison based asking price of what a five figure mortgage payment will get you (factoring in 20 percent down payment for a 30-year fixed mortgage) vs. what it can buy on the rental market.

Aspen, CO

Aspen is king when it comes to luxe mountain getaways. Known as a ski-resort city, the tourist destination has attracted celebrities and affluent socialites for decades helping to transform the Aspen real estate market into a mix of high-end luxury homes and condos. In fact, the median list and sale price in Aspen according to Zillow Real Estate Market Reports both clock in at about $2 million.

With real estate prices remaining in the top-tier, it came as no surprise to find one of the U.S.’s most expensive rentals among Aspen homes for rent, recently listed for $75,000/month (pictured below). The 7,800-sq ft estate sits on a one acre lot just 1.5 miles east of the city. Features include 5 bedrooms, 5 full and 2 half bathrooms, reclaimed oak floors, media room, billiards table, and a large patio with a built-in barbecue. The mountain living masterpiece is also available for short term lease at a still steep rate of $3,000-$7,000/month.

For Rent: (Undisclosed Address), Aspen, CO 81611

For just under $73,000/month, the same renter could become the buyer of a contemporary Aspen estate in Snowmass Village. Located on 40 private acres “just minutes from Aspen and the lifts on Snowmass Mountain,” is a gorgeous 13,000-sq ft home (pictured below) with 7 bedrooms, 7 full and 2 half bathrooms, exercise room, two media/family rooms, game room, office with a deck and wet bar, and a covered patio with a fireplace, pizza oven, grill, fire pit and hot tub. Currently listed for $17,950,000, a 20 percent down payment is about $3.59 million placing a 30-year fixed mortgage payment at $72,794/month.

For Sale: 412 Pioneer Springs Rand Rd, Snowmass Village, CO 81615


Malibu, CA

While snow lovers head to Aspen for all-star slopes, Malibu is a coast-side city where people flock to enjoy the other end of the weather spectrum: sun, surfing, and sand. A few things that Malibu does hold in common with the ski-resort town is an ultra-high median home value—$1,515,100 according to the Zillow Home Value Index—and its reputation as a celebrity real estate hot spot. Take David and Victoria Beckham for example: the budding couple and now 4-kid clan recently swooped up a Malibu home for rent for $158,000/month for the summer. If six figures is a bit of a stretch, then perhaps a $45,000/month Malibu rental (pictured below) could fit the bill and still allow for some surprise run-ins with the British stars. After all, the listing description states the property is available through October.

The luxury 3-bedroom, 3.5-bathroom Malibu rental is situated at the end of a gated drive and “offers complete indoor/outdoor living so you can truly enjoy the beach.” Highlights include walls of glass that open to a beach front patio with BBQ, master suite with fireplace and ocean-view office, and a roof top deck with a brand new spa.

For Rent: 31725 Sea Level Dr, Malibu, CA 90265

For someone looking to become a more permanent neighbor to the stars, a 10-acre, computer-controlled compound could be your answer for just about the same monthly price. Designed by Douglas Busch, this 4,000-sq ft home (pictured below) claims to have 360 degree views of the ocean and be the “most amazing sustainable residence in Malibu.” Green features include steel troweled concrete exterior walls, imported drought tolerant landscaping, solar heated resort size pool.  Currently listed on the Malibu real estate market for $9,945,000, a 20 percent down payment is about $1,989,000 placing a 30-year fixed mortgage payment at $43,083/month.

For Sale: 5757 Trancas Canyon Rd, Malibu, CA 90265


Austin, TX

When it comes to the Lone Star State, everything is big. For starters it’s the largest state in the country, then of course there’s big boots, 10-gallon hats, trucks, guns and…real estate. One of the highest priced rentals in Texas is that of a European influenced estate situated on a 3.2-acre lot with over 12,000-sq ft of living space and a hefty $20,000/month for-rent price tag (pictured below). This Austin rental is uniquely detailed with hand forged iron work, gothic windows, and imported flooring and lighting. Luxury amenities include an 800 bottle wine room, two-story study, fitness room, double edge pool, cave grotto, and panoramic views of Lake Austin. The property also includes a 1,700-sq ft guest house.

For Rent: 3900 Pearce Rd, Austin, TX 78730

What’s bigger than a view of the lake? How about a home on the lake. In addition to a waterfront property on Lake Travis, $20,000/month for a mortgage payment can simultaneously buy a piece of Austin real estate history. Currently listed for $3,950,000, this 4-acre property (pictured below) was originally designed by O’Neil Ford and later updated by Dick Clark and David Dalgleish. The home includes 4 bedrooms, 4.5 bathrooms, indoor pool, and an open floorplan that makes it great for entertaining. With a 20 percent down payment of $790,000, a 30-year fixed mortgage payment would be $21,725/mo.

For Sale: 3500 Ranch Road 620 N, Austin, TX 78734


New York

It has been said before: New York real estate is unlike any other U.S. housing market with some of the highest values per square feet in the country. Likewise, the areas that are the priciest in the city, (e.g. Upper East Side, SoHo, Greenwich Village, West Village), are more often than not a townhouse, penthouse, condo or apartment but rarely a free standing house.  Though not the highest-priced New York home for rent, this 5-floor Manhattan townhouse is looking for a tenant that can hand over $48,650/month (pictured below). With 4,865-sq ft of living space plus a finished garage and private outdoor space, the glamorous home totals over 6,000-sq ft in size. Additional features include a new elevator, intercom system, two terraces, 7 fireplaces, and marble foyer.

For Rent: (Undisclosed Address), New York, NY 10128

If you’re in the market for a mansion in the Big Apple, Manhattan will leave you disappointed. Heading to the Hamptons is your best best. You’ll still face sky-high prices but a yard, close proximity to the beach and significant acreage between neighbors are added amenities. For the price of renting the $50K townhouse above, a buyer could spend only $174 more a month to take a $9.5 million Southampton home off the market. The mid-century estate (pictured below) is situated on the “world famous Lake Agawam” on 1.7-acres of prime Southampton real estate. The cottage-like home has 5 bedrooms, 5 bathrooms, two livings rooms, two fireplaces, brick terraces, outdoor swimming pool and almost 245-ft of private lake frontage. A 20 percent down payment on the Southampton retreat is $1.9 million making for a 30-year fixed mortgage payment of $48,824/mo.

For Sale: 259 S Main St, Southampton, NY 11968


Miami Beach, FL

For the five-figure renter heading to Miami Beach, a modern, 3-story waterfront “palace” (pictured below) could be a dream come true. Built in 2009, the 6,500-sq ft home boasts 100-ft of private waterfront with a dock, heated infinity edge pool, 6 bedrooms all with en-suite baths, an elevator, rooftop wrap-around deck, 2-story living rooms, multiple balconies and terraces, and marble floors throughout. The only thing that isn’t a dream about this Miami Beach rental is the price – $60,000/month.

For Rent: 420 W San Marino Dr, Miami Beach, FL 33139

According to Zillow real estate market reports, the median home value in Miami Beach has risen 9.3 percent since June 2010. Could this mean it’s a good time to buy instead of rent Miami Beach real estate? As it turns out, $60,000 per month can buy another waterfront home. Located on the Intracoastal waterway, this 1.5-acre Mediterranean estate (pictured below) includes an 8-bedroom, 8.5 bathroom main house, guest house, 209 ft of water frontage, billiards room, gym, pool, tennis court and garden room. Currently listed for $12.5 million, a 20 percent down payment is about $2.5 million placing a 30-year fixed mortgage payment at $60,095/month.

For Sale: 4549 Pine Tree Dr, Miami Beach, FL 33140




About the Author

Lauren Riefflin manages news around Zillow Mobile communications and works closely with Zillow's real estate economists in preparing Zillow's real estate market reports. She also focuses on celebrity real estate news as both a Zillow Blog author and manager of celebrity content relationships.

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