After you review the initial setup, please call or email with feedback so that we may provide final refinements to best focus the filtering on exactly what you are looking for.
We will also update you on our “Home Hunter” service, where we find off market properties, not listed or on the internet in specific areas – we’ll talk more about that!
Keith & Yamil 727.460.2687 keithwinn@winnteamrealtors.com yamilwinn@winnteamrealtors.com
Let’s continually adjust the below “Must’s” and “Nice to Have’s” as you learn more about our area and options!
Your Exclusive Search: Two PathsWe Love to help save you time and energy by providing custom, focused searches that will evolve with you as you further refine your “Must’s” and “Nice to Have” lists. We understand that finding the right home is as much about location and lifestyle as it is about the property itself.
Our search strategy is laser-focused on matching your desire for an upgrade with your needs, especially those of Kai (48 lbs. and a certified therapy dog!).
Primary Focus: Condominiums (Most Likely Path)You are looking for a condo that offers a significant upgrade from your current 775 sq. ft. Regatta Beach Club unit.
Property Specs: **2 Bedrooms, 2 Bathrooms, 1,000–1,500 sq. ft.**
Key Consideration: The **48 lb. weight of Kai** will heavily influence which condo buildings we target, as many beachfront and Island Estates buildings have strict weight restrictions (e.g., 20 lbs. or 25 lbs.). We will focus intensely on properties with either no limit or greater than a 50 lb. limit.
Tertiary Focus: Single Family HomesYour interest here is in exploring “what is out there and is anything a low maintenance house that checks our boxes?”
Strategy: First look at condos, then after seeing a few, We will explore listings within **”maintenance-Free”** homes, which typically require less lawn care, landscaping, and exterior upkeep. This allows you to enjoy the benefits of a single-family home (yard for Kai, privacy) without the constant chore of property maintenance.
Target Search Areas| Category | Primary Focus Areas | Secondary/Inland Options |
|---|---|---|
| **Beachfront/Island** | Pinellas Beaches (General) | Island Estates (Clearwater), Clearwater near the Causeway |
| **Coastal/Mainland** | Sand Key (Clearwater), Honeymoon Island Causeway | Dunedin, Safety Harbor |
| **Suburban/Inland** | Palm Harbor, East Lake Woodlands |
**Next Step: Prioritize and Execute**We compiled below a personalized “Hot List” of properties, organized by area and type that meet your criteria. After you review this information, it will be important for us to listen to your feedback so we can further fine tune the searches. As we learn your tastes, we will invest the leg work to reach out to those communities and personally obtain direct confirmation of their dog policies.
Kai's Status: YES - Max 50 lbs.
Size/Sq Ft: Floor plans exist from **950 to 1,500 sq. ft.**.
Current Listings: **High Probability.** Several 2/2 units are actively listed in your range, including a **1,500 sq. ft.** unit for **$499,000** and a **1,150 sq. ft.** unit for **$479,000**.
Note: Located on Island Estates with resort amenities and slips available.
Kai's Status: YES - Max 100 lbs.
Size/Sq Ft: Floor plans generally start **above 1,500 sq. ft.**, up to 2,800 sq. ft.
Current Listings: Units available, but may be slightly larger/higher-end than 1,500 sq. ft. A **1,653 sq. ft.** unit was recently pending for **$669,000**.
Note: One of the few Island Estates condos allowing two large pets, ideal for Kai. Offers a higher-end experience.
Kai's Status: VARIES - Search below covers multiple buildings - Keith & Yamil will call management should a condo be of interest.
Size/Sq Ft: This Price point will return floor plans that are typically **smaller** and **older** to meet the price range (e.g., in buildings like South Beach or Dan's Island).
Current Listings:Listings are typically **2/2 or 1/1** units requiring immediate action. Check the link frequently.
Note: This search provides a broad view of all Sand Key properties under $650k. **Pet policies MUST be confirmed per building by Keith and Yamil.**
While the condo hunt is focused on the very specific, pet-friendly coastal buildings above, when and IF the time is right, next phase will shift to **Single Family Homes** in the **Dunedin, Safety Harbor, Palm Harbor, and East Lake Woodlands** areas. This ensures we cover your "lower maintenance" request and have backup plans that are more flexible for a larger dog.
These properties meet your criteria and are worth considering for in-person tours
These condos offer prime waterfront locations:
These units offer excellent value and unique features:
Hand-picked properties we request your feedback on so we can further fine tune our search
$525,000
1,700 sq ft
Why we picked this: Pet-friendly community, 3 bed/3 bath townhouse, 2-car garage, new roof 2024, walk/bike to beach
⚠️ We'll obtain HOA docs to verify pet weight limits (may have 25-35 lb limit per dog)
$554,000
1,636 sq ft
Why we picked this: Pet-friendly (2 pets up to 100 lbs EACH!), resort amenities, waterfront, seller paying 6 months HOA if closed in January
✓ Kai welcome! Best pet policy in our search
$559,500
1,558 sq ft
Why we picked this: Fully renovated, water views, near Honeymoon Island, 3 bed/2.5 bath townhome, modern design
⚠️ We'll obtain HOA docs to verify pet policy (some sources say 1 pet under 25 lbs, may vary by building)
$599,900
1,755 sq ft
Why we picked this: Waterfront paradise, St. Joseph Sound views, Intracoastal access, near Honeymoon Island, beautifully updated
⚠️ We'll obtain HOA docs to verify pet policy
$499,000
1,249 sq ft
Why we picked this: Steps to Honeymoon Island causeway, waterfront views, reduced $51K, beach-town lifestyle
⚠️ We'll obtain HOA docs to verify pet policy
$675,000
1,458 sq ft
Why we picked this: Pet-friendly (2 pets up to 100 lbs total), 24/7 concierge, waterfront, downtown Clearwater, resort amenities
✓ Kai welcome! (if only dog, or with small 2nd dog under 52 lbs combined)
✓ Best Choices: Sunwatch #501 (2 pets up to 100 lbs EACH - most generous policy!), Waters Edge #312 (2 pets up to 100 lbs total - Kai qualifies as only dog)
⚠️ We'll Verify: For Cutter Cove, Mediterranean Manors, South Paula Point, and Island Towers, Keith and Yamil will obtain HOA documents for your review before making any offer. Some communities have "per dog" limits (e.g., 25 lbs each for 2 dogs = 50 lbs total, which could work for Kai as the only dog). We'll make sure you have complete pet policy details before proceeding.
Sunset Park Summary.
South Tampa is a very special area. There are many families who have owned their homes for generations and an amazing influx of new people from around the world.
The bayshore drive is a unique bayfront 4.5 mile walkway, there is close proximity to downtown Tampa – the sports, plays, restaurants.
There is family fun in South Tampa, yet with greater congestion, smaller parks and an hour to the Gulf Coast beaches.
Our friends and clients that live in South Tampa, gladly accept the trade-offs.
