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Thinking of buying a second home in Miami? Discover the best condos for rental income and lifestyle flexibility—whether you're leaning toward Airbnb-friendly investments or seasonal vacation stays.

The Pros & Cons of Buying a Short-Term Rental Condo in Miami as a Second Home

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New blog 27.06.25

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Midtown Park by PROPER: All about the new Miami pre-construction condo between Midtown, Wynwood & the Design District



Midtown Park by PROPER: Design-Forward Miami Condo With Elevated Hospitality

Palm Bay Condo

Miami

Upper East Side

**America’s other Upper East Side that’s equally sophisticated, yet a lot more relaxed enclave of creativity showcasing MiMo and other dated architectural gems**

**Life in Miami’s Upper East Side**
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**Upper East Side provides the perfect middle ground between urban living and a very suburban, leisurely pace of life. With tree-lined boulevards, pedestrian- and bike-friendly streets, pretty parks, historic (MiMo) architecture, access to the waterfront and proximity to Wynwood and Design District, Upper East Side offers a great package that’s turned it into the residence of choice for our growing creative community.**

**Eastside is where you’d begin your day with a jog through the waterfront Morningside Park. Get to work along Biscayne Boulevard. Stop by for hearty meals at a shaded patio table or MiMo rooftop with a choice of New American to Latin American cuisines in the vicinity. Wind down for the evening with a quick bite at one of the many pizzerias and unique shopping along Biscayne Boulevard. Attend an opening night at a gallery or head for a rooftop sundowner at the Vagabond.**

**You could also take a weekend stroll exploring the various architectural gems (MiMo and others) lining Upper East Side’s streets, or pick organic treats from the Farmers’ Market, or head to Wynwood or Downtown to catch up with friends.**

**Upper East Side’s landscape comprises of large parks, gated communities, modest bungalows, MiMo-style homes and hotels as well as apartment complexes. This is where the bright and modern blends with the dated and earthy. Its most prominent residential sub-neighborhoods consist of Belle Meade, Bay Point and Morningside. There’s also the more traditional Palm Grove, Bayside and MiMo Historic District straddling Biscayne Boulevard.**

**Belle Meade is a prime sub-neighborhood that also borders most of the commercial setup along with its historic residences and waterfront homes. Here’s where you will find Mediterranean-style architecture.**

**Morningside is a historic community with tree-lined avenues and gated living. Most of the single-family homes here are either on the waterfront or a few blocks from the Bay.**

**Mediterranean-style architecture is prevalent here as well, with some of the remarkable homes opening their doors in March for the Historic Morningside Home Tour.**

**Bay Point is where you will find a blend of ultra-modern and traditional homes. This waterfront community boasts of celebrity and high-profile homeowners.**

**Find all your historic hotels, commercial buildings and top restaurants perched along Biscayne Boulevard between 50th and 79th Street.**

**Palm Grove is a small, historic residential sub-neighborhood with single-family homes to apartment buildings. This area, west of the boulevard, is rapidly gentrifying. The Bayside Historic District too is a family-friendly community with homes boasting of Mediterranean-style designs.**

**An up and coming neighborhood, Eastside is where people come to live and end up staying. Being a relatively affordable neighborhood, it has a lot of creative types, startups and young to old professionals setting up base here – whether business or residential.**

**Neighborhood Favorites**
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**Upper East Side offers shopping, dining and play options which are off-the-beaten path**

****Shop** – Move along Biscayne Boulevard and shopping goes beyond the regular boutique or designer dresses. You’ll find a whole gamut of interior designers, furniture designers, edgy boutique stores, art galleries, and unconventional merchants that have set up shop here.**

**For your daily needs, head to the Publix Super Market at Baypoint. For the health conscious, there’s also the Upper East Side Farmers’ Market that takes place every Saturday in the Legion Park, And, for everything else, you can head to the Design District or Shops at Midtown Miami close by.**

****Eat** – Upper East Side’s foodie heaven is peppered along Biscayne Boulevard, which is popular and accessible enough to attract people from around Miami. Ms. Cheezious, as the name suggests, is gourmet grilled cheese paradise (even for the gluten and dairy allergic). It’s most popular indulgences include the BBQ pulled pork melt, mackin melt, grilled blue & bacon, and you can even make your own grilled cheese.**

**LOBA is a popular pick for brunch that serves New American and Latin delights. This charming restaurant serves the best Patacon; other must-tries includes the Vincent Van Goat and Curious George banana bread. Moshi Moshi is the top sushi bar here. It’s known for its unbeatable sushi, pork ramen and super-late night service (till 5 a.m.). And, do not miss Andiamo’s if you’re a pizza lover.**

**The Ni.Do. Caffe serves top-notch authentic Italian, with its Burrata mozzarella being a must-try. Doggi’s Arepa Bar is for Venezuelan wonders with the tequenos here said to be the best in Miami. Barmeli 69 hits the spot for all your Greek food cravings, its relaxed vibe and happy hours have people coming back for more. The intimate Lo de Lea is for amazing Argentinian entrana and wines. The Dogma Grill is to satiate burger and hot dog cravings in a relaxed outdoor setting.**

**Breakfast is best served at Jimmy’s Eastside Diner – do order the corned beef hash and banana pancakes. The Blue Collar’s ragout, shrimp and grits, plus bread pudding make fabulous brunch options. Another great brunch pick is Balans, with its Greek platter and sabayon ice cream.**

**Soyka’s sweet potato fries, fiocchi alle pere, meatloaf and French onion soup are must-tries. Stop by the Vagabond Kitchen and Bar not only for its restored MiMo glory, but also for its New American cuisine, divine cocktail menu and happy hours. All you health conscious folks should head to Organic Bites or Gourmet Station for comfort food, sandwiches and smoothies done right.**

****Drink** – Tap 79 is the hottest gastropub in town with a great selection of craft beers and full menu of gourmet burgers. Special happy hours, drafts on tap, bottled beers, lagers, ales, IPAs, wines and creative pub grub make it a popular haunt. Those looking for premium wines should head to Winewood. The outdoor terrace, live music, happy hours, sangria, lobster ravioli and tapas menu here won’t disappoint.**

**The Vagabond deserves a second mention here for its delicious cocktails, poolside setting, happy hours, live music and DJ parties. Via Verdi’s happy hours, range of wine and Italian food pairings are the talk of the town. Barmeli 69 scores again in the drinks section with its wine on happy hours. Boteco may be famous for its Brazilian eats, but its extensive drinks menu, traditional Brazilian cocktails and happy hours have people coming back for more.**

****Play** – As suburban as its vibe may be, Upper East Side doesn’t disappoint when it comes to play options. Miami Ironside’s multidisciplinary urban center is the hub of creative activity with plenty of trendy special events. Find 67 showrooms, studios and offices - from interior designers to boutique retailers, art galleries and other creative services - nestled in a green environment, accented by public displays of art, restaurants and cafés.**

**The Morningside Park is a local favorite. Walk through the rich greenery, go kayaking, or simply sail off into the horizon. This six-block-long waterfront park also features three tennis courts, two basketball courts, a baseball field, a public pool, barbecue/picnic spots, tot lot and dog-friendly areas for complete family fun.**

**There’s also the kid-friendly Legion Memorial Park. Another waterfront park, Legion has its own recreation center and hosts the Upper East Side Farmers’ Market. So, you can walk or bike through scenic trails, rent a boat, play basketball or take a dance class at this multipurpose facility. Frequent girl scouts programs, after-school camps, fun playgrounds, a picnic area, soccer field, tennis court and more make it a great family-friendly recreation spot.**

**Boundaries**
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**Upper East Side is roughly bound by NE 87th Street, NE 4th Ct., Biscayne Blvd, I-95 and the Bay. Its neighbors are Miami Shores, Little Haiti, El Portal, Wynwood, Design District, Edgewater, North Bay Village and Miami Beach across the John F. Kennedy Causeway.**

**Getting Around**
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**Miami Shores Country Club – 10 minutes by car**

**The Shops at Midtown Miami – 10 minutes by car**

**Design District - 10 minutes by car**

**Wynwood Walls – 12 minutes by car**

**North Beach – 15 minutes by car**

**AmericanAirlines Arena (Downtown) – 20 minutes by car/ 25 minutes by public transit**

**South Beach (Ocean Drive) – 20 minutes by car**

**Douglas Garden Hospital and Miami Children’s Hospital Midtown – 10 minutes away by car**

**Miami International Airport - 20-minute car ride/ 1 hour 15 minutes public transit**

**Biscayne Boulevard, I-95 Expressway and John F. Kennedy Causeway – Quick access**

**Public Transit Options – Upper East Side features ample bus stations, a local trolley system and many private jitney services. Clearly marked bike lanes and ample sidewalks make it easy to navigate on bike and foot.**

**A Brief History of Upper East Side and Where It’s Headed**
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**Most of today’s thriving Upper East Side started off as humble pineapple plantations. Home to some of Miami’s oldest neighborhoods and flaunting the most intact historic architecture, each sub-neighborhood has its own story to tell.**

**The Bayside Historic District (essentially between NE 72nd Street and NE 67th Street) was once part of Lemon City. It is home to one of the oldest communities of Northeast Miami, and still stands surprisingly intact. It was once the choice of residence for many prominent residents who helped develop businesses in Lemon City and the rest of Miami. Development mostly took place here during the early 1900s and went well into the mid-1940s. The most beautiful aspect of this neighborhood is that it still retains most of the architectural styles pertaining to that era. Even today, you can get to see an array of homes and bungalows flaunting Frame Vernacular, Mediterranean Revival, Art Deco, Mission Revival, Streamline Moderne, Florida Ranch and Masonry Vernacular styles in this historic sub-neighborhood.**

**Next comes the popular Morningside. This prominent sub-neighborhood occupies most of southern Upper East Side, from NE 50th Terrace to NE 60th Street. It started off as Bay Shore in the 1920s. Going through ups and downs in tandem with major Miami neighborhoods, it flourished in the mid-20th century and went through a dip during the 60s and 70s. Developed primarily from 1922 to 1941, Morningside is still one of Miami’s best planned subdivisions, complete with tree-lined boulevards. Reminiscent of trends prevalent at the time, Morningside features a concentration of Art Deco, Mediterranean and vernacular style houses, making it the perfect example of a boom-era suburb.**

**The Belle Meade sub-neighborhood saw major construction during the 1940s and 50s and boasts of Mediterranean-style architecture. The area along Biscayne Boulevard, mostly between 50th and 77th street, has been designated as the MiMo (Miami Modern) Historic District. Post the 1980s, this entire area fell to urban decay with an increase in crime, drug pedaling and prostitution. However, preservation efforts started in the early 2000s, rescuing this historic sub-neighborhood with a new lease of life.**

**In a nutshell, all of Upper Eastside, or Northeast as it’s called, saw a residential development boom during the 1920s, with the 50s bringing in funky hotels and modern shopping plazas. It again went through a revival process this past decade, adding new, high-profile residential projects and new independent retailers. This comeback can be traced back to the early 2000s, with a handful of restaurants making it into the neighborhood, followed by businesses now settled along the commercial corridor on Biscayne Boulevard. Additionally, the last real estate boom cycle put Upper East Side back on the map.**

**Today, this historic neighborhood is attracting young professionals and creative types such as photographers, artists, writers, journalists, antique dealers, gallery owners and such. It provides the best of both worlds at a reasonable price point – a suburban haven removed from the city center, yet close to the lifestyle destinations of Miami. A lot of the old buildings and structures remain here, but have been given a facelift to keep up with the times. Residents and civic authorities work hard to retain the original essence and architecture of Upper East Side, while making it a convenient place to live for the modern-day individual and family.**

SepNEWFUB NIakanNEWFUB

This is Sep's description added on Strapi

Stephanie Bienstock

A true Miami Beach native, Stephanie was inspired at the tender age of 16 to become involved in the transformation of the city. Her ability to get along with everyone and instantly put people at ease made her a perfect fit for real estate. Starting as an assistant to a number of top-line producers of the time, she obtained her license at 19 years old. And, there’s been no looking back ever since.


Stephanie continued working for some of the top real estate minds of the city and gained experience working with affluent clients. This led her to finally begin selling real estate independently in the early 2000s. Since then, her exclusive focus has been luxury waterfront properties, and she has participated in the sale of over $350,000,000 in sales. A feat that has helped many discerning clients find their picture-perfect property on the water.


Stephanie is often described as an open, easy going and genuine person. Being a perfectionist, she loves being organized and well-prepared. This comes in handy for her clients, as she not only brings a sense of structure to their entire experience but also helps put things into perspective for others, giving them the clarity they need to make good decisions.


Besides striving to excel at everything she does, Stephanie loves exercising and a good cup of coffee. She’s a dedicated mom of two and wife of one who really takes enjoyment in spending time with them. Not many know that this perfectionist has ninja-fast reflexes and also packs a mean punch. So spar with her at your own risk.

Yurii Kryzhanovskyi

Thank you for visiting my profile. My name is Yuriy Kryzhanovskyi, Managing Broker of Blackbook Properties and a real estate sales top producer in the Miami area for the past 15 years.
I pride myself on keeping the buying and selling process simple and fun, being a knowledgeable guide for my clients, and negotiating to get my clients what they want at a fair price.

Michael Castner

Thank you for visiting my profile. My name is Taras Chaban, Managing Broker of Blackbook Properties and a real estate sales top producer in the Miami area for the past 15 years.
I pride myself on keeping the buying and selling process simple and fun, being a knowledgeable guide for my clients, and negotiating to get my clients what they want at a fair price.

Eric Lieberbaum

Born and raised on Miami Beach, Eric's deep-rooted connection to the city gives him an unmatched understanding of its diverse neighborhoods, unique architecture, and vibrant lifestyle.

A graduate of Florida State University with a BS in Marketing, Eric brings a strategic and creative approach to real estate. His passion for the industry stems from a lifelong fascination with Miami's ever-evolving landscape, fueled by his love for exploring new developments and experiencing the city's dynamic social scene.

Clients appreciate Eric's adaptable nature, unwavering determination, and infectious sense of humor. His empathetic approach and natural ability to connect with people make the real estate journey enjoyable and stress-free.

Eric's ideal clients share his zest for life and appreciate his ability to balance professionalism with a genuine, friendly demeanor. Whether you're searching for properties in Brickell, the Design District, or Miami Beach, Eric's local expertise and personalized service will ensure you find the perfect place to match your lifestyle and aspirations.

When Eric isn't helping clients achieve their real estate dreams, you can find him exploring Miami's culinary scene, enjoying the beach, or staying active with fitness classes. His love for Miami's proximity to the ocean reflects his own energetic spirit and unwavering passion for the city he calls home.

Sep Niakan

Richard Ostertag is a dedicated real estate professional with a passion for numbers, strategy, and helping his clients achieve financial success through real estate. Originally from Slovakia, Richard's journey has taken him across the globe, enriching his perspective and fueling his drive to achieve his dreams.

With a Bachelor's degree in Economics and Management from the University of Economics in Prague, Richard brings a sharp analytical mind and a deep understanding of the financial intricacies involved in real estate investing, with a specialized focus on short-term rentals and income generating properties. His experience living and working in various countries has instilled in him a global outlook and an appreciation for diverse cultures.

As a real estate investor himself—he recently closed on his 9th property—Richard's clients value his first-hand experience, in-depth understanding of real estate financials and projections, transparency, dedication, and unwavering commitment to finding the investment that matches their specific investment and personal goals. His friendly and easy-going nature makes him approachable and fosters a collaborative environment where clients feel heard and understood, and also know they are very capable hands.

Beyond real estate, Richard enjoys a healthy and active lifestyle, indulging in morning walks, weightlifting, yoga, and meditation. He's also passionate about travel, cooking, and expressing his creativity through interior design. 

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