Upside Boca Raton
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5500 N Military Trl, Boca Raton, FL 33496
For more information about senior living options: (844) 490-3973
At Upside Boca Raton, monthly costs for living accommodations reflect a premium positioning within the market when compared to both Palm Beach County and the broader state of Florida. For example, a semi-private room is priced at $3,759, slightly above the county's average of $3,592 and significantly higher than the state average of $3,009. The trend continues with private rooms costing $4,510 at Upside Boca Raton versus $4,444 in Palm Beach County and $3,699 statewide. Studio apartments are available for $4,886 - again surpassing both local and state averages - and 1-bedroom units escalate to $6,000 compared to $4,362 in the county and $3,864 across Florida. Finally, 2-bedroom options at Upside reach $7,250 while remaining competitive yet elevated against the county's price of $5,359 and a state average of $4,711. These figures indicate that Upside Boca Raton provides an upscale living experience well above other regional offerings.
| Floor plans | Upside Boca Raton | Palm Beach County | Florida |
|---|---|---|---|
| Semi-Private | $3,759 | $3,592 | $3,009 |
| Private | $4,510 | $4,444 | $3,699 |
| Studio | $4,886 | $4,274 | $3,823 |
| 1 Bedroom | $6,000 | $4,362 | $3,864 |
| 2 Bedrooms | $7,250 | $5,359 | $4,711 |
Upside Boca Raton is best suited for active seniors who want a luxury, resort-like living environment with ready access to caregiving support through Upside+. It’s a place where independence is foregrounded, but with the comfort of 7-day-a-week certified care available through Upside+. Reviewers consistently describe a community that feels like a refined, friendly neighborhood rather than a medical facility, anchored by a walkable location near Fresh Market, restaurants, and shopping. The property itself is praised for its beauty, well-maintained grounds, and a social calendar that makes it easy to plug into activities. For older adults who prize high-end amenities, a strong sense of security, and real opportunities to socialize without the rigidity of a traditional senior-living campus, Upside Boca Raton checks the right boxes.
That said, potential residents should consider alternatives if heavy, round-the-clock medical supervision or memory-care-level support is needed on a daily basis. The Upside model emphasizes independence with optional care, not a full-service skilled-nursing or memory-care environment. Families evaluating options for a family member with advanced dementia, substantial mobility limitations, or complex medical regimens may find traditional assisted living or a memory-care facility more appropriate. Additionally, those who are especially cost-conscious or who demand absolute reliability in every appliance and service may want to compare with other luxury rentals or with communities that offer stricter, more predictable maintenance and pricing structures.
The strongest positives here are the people and the culture. Across dozens of accounts, the staff stands out as the defining feature: friendly front-desk teams, responsive maintenance crews, and managers who genuinely seem invested in residents’ well-being. Residents repeatedly highlight individuals like Steven, Josh, Giselle, Kayla, and Julio for going above and beyond, whether guiding a move-in, solving a maintenance problem in minutes, or simply greeting every day with a genuine smile. The sense of community, paired with well-thought-out spaces, from pool and wellness areas to social rooms and outdoor amenity clusters, creates a living experience that feels less like a building and more like a thoughtfully curated neighborhood. The dog-friendly policy and the ease of daily life, shopper-friendly walkability, plentiful parking, and even extras like EV chargers and complimentary coffee, add real practical value.
The flip side is that several reviews flag affordability and occasional operational hiccups as meaningful caveats. The price point is consistently described as high, with residents accepting the premium in exchange for luxury amenities and a polished environment; however, some reviews point to policy shifts and charges that can feel onerous, such as rumored or implemented costs for common-area electricity and for running vacant units. Maintenance and turn-key reliability also surface as recurring themes: blinds that don’t stay up, washers and dryers that misbehave, and certain repair timelines that test patience. Communication gaps during the move-in process and occasional delays in handling packages or access issues have left some residents frustrated. These are real frictions that can erode the perceived value unless kept in tight check by proactive management.
Still, the way the pros line up against these cons often tilts decisively in favor of Upside Boca Raton for many families. The luxury aesthetic, immediate access to on-site care, and a community that feels cohesive and caring deliver a compelling value proposition for someone weighing the trade-off between independent living and assisted care. When management and on-site teams are consistently accessible, the anxiety around relocating a parent or aging relative can be significantly lowered. The social fabric, events, casual social spaces, and a culture of recognizing residents, adds qualitative benefits that are hard to quantify but hard to replace. For families who want their loved one to enjoy a high-quality, maintenance-light lifestyle with a safety net of caregiving options, the positives are robust enough to outweigh the occasional service gluts or price concerns.
Bottom line: Upside Boca Raton represents a premium, thoughtfully managed option for seniors who prize independence, social engagement, and hotel-like amenities with the reassurance that care can scale up when needed. It is less well suited for those who require constant clinical oversight, who are highly price-sensitive, or who insist on perfect, error-free operations without any maintenance lag. The most effective approach is a candid, head-to-head comparison with other luxury rentals and with traditional assisted living options, focusing on two questions: can Upside+ reliably supplement daily needs without eroding independence, and can the on-site team deliver consistent, transparent service at a rate that matches the investment? Tour with the trusted frontline team, Steven, Josh, Giselle, Kayla, and the maintenance crew, and press for specifics on move-in timelines, washer-dryer reliability, mail-key provisioning, and the exact terms of any shared-utility charges. If those align, Upside Boca Raton is a compelling choice that can deliver the “best of both worlds”, a refined living environment with meaningful support when necessary.
Upside Boca Raton is a luxurious assisted living community located in the vibrant city of Boca Raton, FL. Our community offers a wide range of amenities and care services to ensure that residents enjoy a comfortable and fulfilling lifestyle.
Our spacious apartments are equipped with air-conditioning and offer beautiful garden views. Ground floor units and handicap accessibility are available for those with mobility needs. Each apartment features a private bathroom and some even include full kitchens or kitchenettes for those who prefer to prepare their own meals.
Residents can take advantage of our indoor and outdoor common areas, where they can socialize with fellow residents or relax in the sunshine. Our swimming pool and hot tub provide opportunities for exercise and relaxation. Additionally, we offer devotional services off-site to meet the spiritual needs of our residents.
At Upside Boca Raton, we prioritize the well-being of our residents by providing high acuity care, incontinence care, and medication management services. Our dedicated staff members are trained to provide personalized assistance based on individual needs.
Dining at Upside Boca Raton is truly a culinary experience. Our professional chef prepares delicious meals using fresh ingredients, catering to various dietary preferences including gluten-free, kosher, low/no sodium, vegan, vegetarian, organic, and no sugar options. Guests are welcome to join residents for meals or room service is available upon request.
We understand the importance of staying active and engaged in life. That's why we offer a variety of activities such as BBQs or picnics, devotional activities offsite, happy hour gatherings, holiday parties, intergenerational programs, and live musical performances.
Upside Boca Raton is conveniently located near numerous cafes, parks, pharmacies, physicians' offices, restaurants, places of worship, theaters, and hospitals. Residents have easy access to various amenities that enhance their quality of life.
Come experience the comfort and luxury at Upside Boca Raton where each resident receives exceptional care in a beautiful and friendly environment.
This part of Boca Raton, Florida, offers a variety of amenities that cater to senior living. The proximity to parks such as Boca Tierra Park and South County Regional Park provides opportunities for outdoor recreation and social activities. There are several pharmacies nearby for convenience in accessing medications and healthcare needs. Places of worship like Congregation B'nai Israel and B'nai Torah Congregation offer spiritual support within the community. A range of dining options, including City Fish Market and Casa Tequila, provide diverse culinary experiences. The theaters at Regal Shadowood and Cinemark Premier offer entertainment options, while numerous physicians' offices and hospitals ensure access to quality healthcare services. Cafes like The Seed and Starbucks provide relaxed settings for socializing or enjoying a cup of coffee. Overall, this area of Boca Raton offers a well-rounded lifestyle suitable for seniors looking for a vibrant and convenient living environment.
At Upside Boca Raton, monthly costs for living accommodations reflect a premium positioning within the market when compared to both Palm Beach County and the broader state of Florida. For example, a semi-private room is priced at $3,759, slightly above the county's average of $3,592 and significantly higher than the state average of $3,009. The trend continues with private rooms costing $4,510 at Upside Boca Raton versus $4,444 in Palm Beach County and $3,699 statewide. Studio apartments are available for $4,886 - again surpassing both local and state averages - and 1-bedroom units escalate to $6,000 compared to $4,362 in the county and $3,864 across Florida. Finally, 2-bedroom options at Upside reach $7,250 while remaining competitive yet elevated against the county's price of $5,359 and a state average of $4,711. These figures indicate that Upside Boca Raton provides an upscale living experience well above other regional offerings.
Upside Boca Raton is located at 5500 N Military Trl, Boca Raton, FL 33496 in Palm Beach County, Florida
Upside Boca Raton on seniors.fyi includes 22 photos including images showing palm trees, interior, landscaping, kitchen, swimming pool, outdoor, bathroom, building, and more.
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