Amanda Black - Upside Real Estate

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Windermere, FL
Amanda Black - Upside Real Estate

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Realtor + Interior Designer
Windermere Local since 1979

11/03/2026

✨ MOVE-IN READY IN DR. PHILLIPS! ✨

The perfect blend of style, comfort, and location.

Located in Toscana, a gated community with a pool and fitness center, just minutes from Universal Studios, Restaurant Row, and major roadways.

7149 Regina Way | Orlando

📐 2,104 SF | 3 Bedrooms | 2.5 Baths
✨ Beautifully remodeled
💰 Offered at $610,000

09/22/2026

Old Windermere is HOT 🔥
All 7 lots are officially PENDING! Grateful to live and work in this special place — where the oaks are old, the lake is close, and demand speaks for itself. 🏡
Thank you to everyone who reached out — more to come soon. 👀

618 Ridgewood Dr | Windermere

09/15/2026

BRING YOUR BUILDER! 🏡 Opportunities like this don’t come around twice.

7 vacant homesites being offered together for the FIRST TIME ever. Cleared and ready to build your dream home. 🌳

✨ Golf cart friendly streets
✨ Butler Chain of Lakes access
✨ Natural gas + county water
✨ NO HOA
✨ Walk to downtown shops, restaurants & events

Lots approx. 100’ x 167’

💰 Lots 19-22: $650K each
💰 Lot 18: $700K
💰 Lot 29: $750K
💰 Lot 30: $800K

09/11/2026

🏡 RARE OPPORTUNITY IN OLD WINDERMERE 🏡

7 vacant homesites being offered together for the FIRST TIME. Cleared and ready to build your dream home. 🌳

✨ Golf cart friendly streets
✨ Butler Chain of Lakes access
✨ Natural gas + county water
✨ NO HOA
✨ Walk to downtown shops, restaurants & events

Bring your builder — opportunities like this don’t come around twice.

RIDGEWOOD DRIVE | TOWN OF WINDERMERE

💰 Lots 19-22: $650K
💰 Lot 18: $700K
💰 Lot 29: $750K
💰 Lot 30: $800K

DM for details!

08/28/2026

SOLD...Charming home located steps from Lake Bessie. ☀️
This one was truly a pleasure! 🥰

109 E. 12th Avenue | Windermere
4 BD | 3.5 BA | 2,791 SF
SP $1,150,000

08/06/2026

JUST SOLD! Modern pool home with views of John’s Lake ☀️
16437 Good Hearth | Clermont, FL
3 BD | 2.5 BA | 2,724 SF
SP $745,000

07/30/2026

SOLD...Original 1973 ranch in downtown Windermere. Best wishes to one of our favorite neighbors on their new adventure! ☀️

5 BD | 2/1 BA | 2,539 SF | 0.42 Acres

SP $765,000

07/24/2026

SOLD IN 1 DAY - FULL PRICE! 🔥
11407 WILLOW GARDENS DR
Town of Windermere
5 BD | 3 BA | 3,501 SF
SP $1,200,000

06/10/2026

Original 1970’s charmer offered for the first time! Located steps from the brewery, restaurants & shops.

412 Forest Street

5 BD | 2.5 BA | 2,539 SF | $840,000

05/21/2026

Can’t beat this view! ✨🍾
414 E. 5th Ave

Address

Windermere, FL
34786

Telephone

+14076160140

Website

http://www.upsiderealestategroup.com/

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