
2258 HILLVIEW STREET, SARASOTA, FL, 34239
Active3 days on marketListed Nov 4, 2026MLS #A4708958
About this home
2258 HILLVIEW STREET
Virtually Staged. Welcome to 2258 Hillview Street, in the coveted Arlington Park neighborhood. At 2,921 square feet of living space, this 4-bedroom, 4.5-bath home pairs a coastal luxury aesthetic with custom craftsmanship and seamless indoor-outdoor living, all just minutes from Downtown Sarasota and the #1 ranked best beach Siesta Key. Custom built in 2021 and meticulously maintained, this home brings an Old Florida charm to new construction. A covered front porch, soft green shingle-style siding, a red front door, a metal roof, and a paver driveway give it a welcoming, timeless look. As you enter, the space greets you with tall ceilings and expansive impact-rated windows that fill the home with natural light. Gorgeous wide-plank hardwood, smooth textured walls and ceilings, and curated designer finishes keep everything clean and polished. The kitchen is a stunner, with custom wood cabinetry, premium stainless appliances, under-cabinet lighting, a pot filler, and an oversized black walnut butcher block island. Built-in window seats with custom cushions and storage below tuck into the kitchen and the living room nook. The main floor primary suite is a private retreat with a designer wallpaper accent wall and tray ceiling, two walk-in closets with custom closet systems, and sliding doors that open to the pool and patio. The spa-inspired bath has a freestanding soaking tub set against mirrored arabesque glass tile, an oversized marble walk-in shower, and a double vanity with additional storage. The iconic banana leaf wallpaper covered hallway leads to the laundry room, which has teal custom cabinetry, a utility sink, built-in hanging rods, and loads of storage. The powder bath is covered floor to ceiling in blue mosaic tile and has easy access to the pool and patio. The shiplap staircase has hardwood treads and a fun leopard print runner leading to a loft with additional living space. Three more bedrooms with custom closets and beautifully finished baths offer plenty of room. Outside, the saltwater pool has a waterfall, and the covered paver lanai is made for dining and lounging. Mature tropical landscaping, an outdoor shower, and irrigation round out the outdoor space, and a soft water treatment system serves the whole home. An oversized driveway leads back to the gated entry for the detached two-car garage. Arlington Park & Aquatic Complex is nearby, with a 50-meter lap pool, tennis and basketball courts, an outdoor fitness area, a half-mile walking trail, and a dog park. Southside Village has restaurants and shops, and Morton’s Gourmet Market and Sarasota Memorial Hospital are close too. Downtown Sarasota, Siesta Key, Lido Key, and St. Armands Circle are all just minutes away, and there are no HOA fees.
Facts & features
The home at a glance
4
Bedrooms
4.5
Bathrooms
2,921
Sqft
0.16 ac
Lot size
2
Garage
2021
Year built
Two
Levels
$719
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$15,655 /mo · 10% down Conventional, 30-yr fixed at 7.5%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:

Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$15,655/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Can I afford this home? → See what you can comfortably afford from your income, debts and savings.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+12.8%
$/sqft vs Sarasota actives
$719 vs $319
Days on market
3 vs 67 typical
Where $719/sqft sits among the 400 Sarasota actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Arlington Park
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Sarasota. See the full Sarasota guide →
Arlington Park — neighborhood snapshot
Population
3,506
Median age
50
Median income
$82,920
Median home value
$428,514
Avg household
2
Households w/ children
307
For the school run
Sarasota County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Sarasota market
$450K → $491K
Sarasota median sold, yr/yr
95.4%
Sale-to-list ratio (12 mo)
187 of 400
Sarasota actives have cut their price
Median sold price, Sarasota, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 242% above the SARASOTA 34239 median. See the full Sarasota market guide →
Paper trail
This home's history
Reality check
What actually sold near 2258 HILLVIEW STREET
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Dec ’25$1,445,000
2283 ARLINGTON STREET · same community
5 bd · 4.5 ba · 2,977 sqft · $485/sqft · 234 DOM
Sold · Jul ’26$949,000
2254 HAWTHORNE STREET · same community
3 bd · 2.5 ba · 2,332 sqft · $407/sqft · 196 DOM
Sold · Nov ’25$550,000
2122 WALDEMERE STREET · same community
4 bd · 2 ba · 1,709 sqft · $322/sqft · 12 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.

Your agent
Tommy Trainer
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 2258 HILLVIEW STREET — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2258 HILLVIEW STREET — before you fall in love.
See it in person
Schedule a tour
Live availability from Tommy's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
2258 HILLVIEW STREET FAQs
What would the monthly payment be for 2258 HILLVIEW STREET?+
With 10% down on a 30-year Conventional loan at 7.5%, the all-in payment lands around $15,655/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 2258 HILLVIEW STREET?+
The most recent tax bill on record (2025) was $17,914. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Sarasota?+
At $2,100,000, this home is listed about 276% above the Sarasota median of $559,000. The market section on this page shows how the area is trending.
Which schools are assigned to 2258 HILLVIEW STREET?+
Alta Vista Elementary School (elementary), Sarasota High School (high), Brookside Middle School (middle) — Sarasota County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$2,100,000 runs 242% above the SARASOTA 34239 median — but at 2,921 sqft it's also 73% larger than the typical Sarasota listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Fresh on the market
Only 3 days on market in a Sarasota market that averages 67 — if it fits, move quickly.
Keep looking
Similar homes nearby
Listing courtesy of PREFERRED SHORE LLC · Jessica Kenney. MLS #A4708958.
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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