Neighborhood · Stuart, Florida
Trailside
Rare acreage and estate living near Stuart
3
Homes for sale
$5,995,000
Median list price
$1,101
Avg price / sqft
141
Median days on market
Trailside sits in the quieter, greener reaches of Martin County, where lot sizes stretch out and homes are built to a scale you rarely see closer to the coast. This is estate territory — expansive floor plans, room to breathe, and a pace that feels a world away from downtown Stuart homes for sale yet keeps you within easy reach of them. Neighboring communities like Harbor Estates, St. Lucie Falls, and Sunshine Parkway Manor round out the character of this pocket of Stuart.
The market here is small and top-heavy: just three active listings, with a median list price of $5,995,000 and homes averaging nearly 5,000 square feet. Nothing has closed in the past 12 months, so pricing is set by what sellers are asking rather than recent comps — and at a median 141 days on market, buyers have real time to negotiate. If you're shopping this segment, study the live map closely, because inventory turns over slowly and each home is genuinely distinct.
Trailside is a community in Stuart, Florida.
Quick facts
$2,500,000 – $6.2M price range
4,929 sqft median home
On the market now
Homes for sale in Trailside
$5,995,000
2985 SW Trailside Path, Stuart FL 34997, STUART
7 bd · 7.5 ba · 7,517 sqft
$6,200,000
2541 SW Trailside Path, Stuart FL 34997, STUART
3 bd · 3.5 ba · 4,929 sqft
$2,500,000
2986 SW Trailside Path, Stuart FL 34997, STUART
2 bd · 2 ba · 2,002 sqft
Every active listing inside the Trailside boundary
Open full map search →Find your fit
Browse Trailside
By feature — on the live map
The numbers that matter
The Trailside market
Trailside vs Stuart
Median list price
Price per sqft
Days on market
Live Stellar MLS data — every listing and closed sale inside the Trailside boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Trailside is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Trailside home
≈ $32,909/mo
$5,995,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
49
Median age
51
Median income
$79,929
Median home value
$312,000
Beyond the listings
Living in Trailside
Lifestyles
Top 1% in the U.S.Farm Culture
Do you know where your food comes from? These people do, and they want to share their love for farming and simple living with the community.
Relationships
Top 2% in the U.S.Happily Ever After
Whether it's the stress of wedding planning or looking back on that special day, this population has their eyes and hearts focused on lifelong commitment.
Food & Drink
Top 2% in the U.S.Ingredient Attentive
These folks are conscious about what they eat. They're looking for ingredients that not only taste great, but also have great nutritional benefits.
Hobbies & Interests
Top 3% in the U.S.Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Culture
Top 4% in the U.S.Sites to See
This population finds the most beautiful sites just by looking up. Sunrise, sunset or sometime in between, these people love to marvel at man-made and natural wonders.
Lifestyles
Top 6% in the U.S.Wealth Signaling
Interested in the finer things life has to offer, this population wants to display their lifestyle by discussing luxury products. Often references jewelry, cars, and home features.
Straight answers
Trailside FAQs
Is Trailside a good place to live?+
It's a strong fit if you want space, privacy, and estate-scale homes in the greener part of Martin County. Homes average close to 5,000 square feet, and the area is assigned to South Fork High School and Crystal Lake Elementary. The trade-off is a very small, quiet market rather than a dense, amenity-packed neighborhood.
Is Trailside expensive?+
Yes — this is one of the higher-end pockets near Stuart. The three active listings run from $2,500,000 to $6,200,000, with a median list price of $5,995,000, and every home currently for sale is priced above $1 million.
What do homes cost in Trailside?+
Current listings carry a median price of $5,995,000 and average about $1,101 per square foot across a median home size of 4,929 square feet. Because the homes here are large and individual, price is driven more by acreage and features than by a tight per-foot formula. Comparing to nearby Crystal Lake Elementary School zoned areas can help set expectations.
How is the market in Trailside right now?+
It's a small, slow-moving market with just three active listings and no sales in the past 12 months. The median days on market is 141, which means well-priced patience — on both sides — tends to win. Watch the live map since new inventory is infrequent.
What about HOA fees and property taxes in Trailside?+
HOA data isn't available for the current listings, which is common for large-lot estate areas without a formal community association. Property taxes run a median of about $13,351 per year, reflecting the high assessed values of these homes.
Keep exploring
More Stuart neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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