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Home › Windermere › Latest Listings

Latest Windermere Real Estate Listings

Windermere has always been one of Orlando's hottest real estate markets and sought after addresses. Below are the twenty five newest home listings in Windermere. This list updates every 5 minutes, so make sure to bookmark this page and check back often. You may also create a search and get automatic updates for Windermere or any other area you like. Need help? Just message us.

25 Most Recent Windermere Real Estate Listings

14360 Crest Palm Avenue, Windermere image
14360 Crest Palm Avenue, Windermere $1,270,000

Experience elevated Florida living in this extraordinary 4,585-square-foot estate, ideally positioned in the heart of Windermere and just 2 miles from Magic Kingdom. Buil...

  • 6 Beds
  • 5 Baths
  • Palms/Windermere SubDv.
  • 34786 Zip Code
13322 Bellaria Circle, Windermere image
13322 Bellaria Circle, Windermere $2,795,000

BELLARIA ESTATE. Toll Brothers-built Spanish/Mediterranean estate on a 0.76-acre homesite in Bellaria, Windermere's 64-home, 24-hour guard-gated enclave off Lake Butler R...

  • 5 Beds
  • 7 Baths
  • Bellaria SubDv.
  • 34786 Zip Code
8156 Boat Hook Loop Unit 623, Windermere image
8156 Boat Hook Loop Unit 623, Windermere — 8156 $327,000

Welcome to your new home! This beautifully maintained, newly listed 3-bedroom, 2-bathroom, third-floor condo is located in the highly desirable Lakeside at Lakes of Winde...

  • 3 Beds
  • 2 Baths
  • Lakeside/Lks/Windermere SubDv.
  • 34786 Zip Code
4243 Isabella Circle, Windermere image
4243 Isabella Circle, Windermere $3,290,000

Welcome to an exceptional luxury residence in the prestigious gated community of Casabella in Windermere. Set on a private 0.71-acre homesite, this stunning Toll Brothers...

  • 5 Beds
  • 7 Baths
  • Casabella SubDv.
  • 34786 Zip Code
8142 Tibet Butler Drive, Windermere image
8142 Tibet Butler Drive, Windermere $2,685,000

Expansive golf course and water views abound from this impressive Keene’s Pointe estate residence, located on the 3rd green of the renowned Jack Nicklaus Signature Golf C...

  • 5 Beds
  • 7 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
5373 Isleworth Country Club Drive, Windermere image
5373 Isleworth Country Club Drive, Windermere $7,200,000

Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyon...

  • 5 Beds
  • 6 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
4301 Down Point Lane, Windermere image
4301 Down Point Lane, Windermere $2,950,000

Lakefront estate on Lake Down in the Butler Chain of Lakes with over 150 feet of frontage and no HOA in Sunset Bay. Built in 1983, this 5 bedroom, 4 bath pool home offers...

  • 5 Beds
  • 4 Baths
  • Down Point Sub SubDv.
  • 34786 Zip Code
6243 Andreozzi Lane, Windermere image
6243 Andreozzi Lane, Windermere $720,000

Welcome to this spacious pond-front home in Providence, featuring a private screened pool and peaceful water views. Major updates include the roof, A/C system, and water ...

  • 4 Beds
  • 2 Baths
  • Providence Ph 01 50 03 SubDv.
  • 34786 Zip Code
12417 Cruxbury Drive, Windermere image
12417 Cruxbury Drive, Windermere — 12417 $360,000

Welcome to the peaceful townhome community of The Lakes of Windermere, conveniently nestled just behind Walt Disney World’s Magic Kingdom! Enjoy beautiful green space out...

  • 2 Beds
  • 3 Baths
  • Lakes/Windermere-Lk Reams Twhm SubDv.
  • 34786 Zip Code
515 W 2nd Avenue, Windermere image
515 W 2nd Avenue, Windermere $3,300,000

Experience the extraordinary lifestyle of waterfront living in the heart of historic Windermere. Set on approximately 2/3rd of an acre with an impressive 100 feet of fron...

  • 4 Beds
  • 6 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
9155 Outlook Rock Trail, Windermere image
9155 Outlook Rock Trail, Windermere $795,000

Set against a natural preserve, this Windermere home combines a flexible floor plan, thoughtful upgrades, and a backyard setting that feels removed from the everyday. Nat...

  • 5 Beds
  • 5 Baths
  • Windermere Trls Ph 5b SubDv.
  • 34786 Zip Code
9764 Gotha Road, Windermere image
9764 Gotha Road, Windermere $450,000

Opportunity awaits at 9764 Gotha Road! This 2-bedroom, 1-bathroom home offers 1,216 square feet of living space, a private fenced yard, and NO HOA. Whether you're searchi...

  • 2 Beds
  • 1 Baths
  • Gotha Town SubDv.
  • 34786 Zip Code
5050 Isleworth Country Club Drive, Windermere image
5050 Isleworth Country Club Drive, Windermere $3,189,000

Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course view...

  • 4 Beds
  • 5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
5379 Isleworth Country Club Drive, Windermere image
5379 Isleworth Country Club Drive, Windermere $3,400,000

This luxury estate in Isleworth offers a rare opportunity to remodel or create a custom estate in the highly coveted Isleworth community. Situated directly on the 17th ho...

  • 4 Beds
  • 4 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
14077 Ancilla Boulevard, Windermere image
14077 Ancilla Boulevard, Windermere — 14077 $399,000

Virtually Staged. There is something truly special about coming home to Summerport and this move-in-ready townhome captures that feeling perfectly. From the moment you ar...

  • 3 Beds
  • 3 Baths
  • Summerport Edens Hammock SubDv.
  • 34786 Zip Code
2540 Hempel Cove Ct, Windermere image
2540 Hempel Cove Ct, Windermere $1,399,900

Virtually Staged. Set on just over an acre in Windermere, this updated 5-bedroom, 3-bath pool home offers 3,356 square feet of living space, plus a separate flex/bonus ro...

  • 5 Beds
  • 3 Baths
  • Lake Down Cove SubDv.
  • 34786 Zip Code
13048 Garridan Avenue, Windermere image
13048 Garridan Avenue, Windermere — 13048 $445,000

Beautiful Two-Story Townhome in Windermere Sound!! Welcome to this charming two-story townhome located in the desirable Windermere Sound community. This spacious residenc...

  • 3 Beds
  • 3 Baths
  • Windermere Sound Ph 2 SubDv.
  • 34786 Zip Code
13503 Lake Cawood Drive, Windermere image
13503 Lake Cawood Drive, Windermere $1,500,000

5 Bed 6 bath custom built home in gated community, 1.02 acre lot with private well for all water supply, NO water or sewer bill. Private Basketball court, overside Pool a...

  • 5 Beds
  • 7 Baths
  • Lake Cawood Ests Rep SubDv.
  • 34786 Zip Code
13239 Jervey Street, Windermere image
13239 Jervey Street, Windermere $710,999

*This home can be purchased with NO INCOME VERIFICATION.* Welcome to 13239 Jervey Street, an elegant 4-bedroom, 3.5-bath residence offering 2,745 square feet in the highl...

  • 4 Beds
  • 4 Baths
  • Lake Sawyer South Ph 01 SubDv.
  • 34786 Zip Code
13844 Amelia Pond Drive, Windermere image
13844 Amelia Pond Drive, Windermere $600,000

Fresh interior/exterior paint and HVAC serviced! Residing in Summerport, this delightful home features a practical design with spacious room sizes and a tranquil pond vie...

  • 4 Beds
  • 3 Baths
  • Summerport Phase 1 SubDv.
  • 34786 Zip Code
13325 Lush Lime Alley, Windermere image
13325 Lush Lime Alley, Windermere — 2 $641,681

Under Construction. Enjoy convenient, low-maintenance living in this two-story townhome featuring a private paver courtyard and two-car garage, perfectly located in the h...

  • 3 Beds
  • 3 Baths
  • Lake Cawood Cove SubDv.
  • 34786 Zip Code
5526 Marleon Drive, Windermere image
5526 Marleon Drive, Windermere $2,500,000

A rare opportunity to own one of just 18 custom estate homes in this exclusive Windermere enclave of Lake Davis Reserve. Set on more than half an acre, this impressive fi...

  • 5 Beds
  • 5 Baths
  • Lake Davis Reserve A & B SubDv.
  • 34786 Zip Code
9021 Via Di Canti, Windermere image
9021 Via Di Canti, Windermere — 9021 $550,000

Welcome to this beautifully appointed corner-unit townhome in the highly sought-after area of Windermere, Florida! Ideally located just 15 minutes from Walt Disney World,...

  • 5 Beds
  • 4 Baths
  • Royal Estates SubDv.
  • 34786 Zip Code
12989 Westside Village Loop, Windermere image
12989 Westside Village Loop, Windermere $1,159,000 ▼

Beautifully upgraded 4-bedroom residence featuring a thoughtfully designed floor plan, custom finishes, and exceptional indoor-outdoor living. The main level offers a pr...

  • 4 Beds
  • 4 Baths
  • Westside Village SubDv.
  • 34786 Zip Code
4844 Flint Road, Windermere image
4844 Flint Road, Windermere $529,000

Don’t miss the opportunity to make this beautiful home in the highly sought-after Summerport community your own! Known for its A-rated schools, picturesque surroundings, ...

  • 3 Beds
  • 2 Baths
  • Summerport Ph 05 SubDv.
  • 34786 Zip Code
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Realtor David MyersDavid Myers
Your Windermere Neighborhood Expert
Call/Text: 407.801.3286
Windermere Home Buyers Guide

Windermere Neighborhoods

  • Arlington Bay
  • Ashlin Park
  • Balmoral
  • Bellaria
  • Bella Vita
  • Belmere Village
  • Berkshire Park
  • Butler Ridge
  • Carrington
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  • Lake Butler Estates
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  • Lake Reams Townhomes
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  • Legado
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  • Magnolia Park
  • Manors at Butler Bay
  • Marina Bay Estates
  • Merrick Landing
  • Newbury Park
  • Oasis Cove
  • Oxford Moor
  • Palms at Windermere
  • Peachtree Park
  • Prsrve Lks Windermere
  • Preston Square
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  • Reserve at Belmere
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  • Roberts Landing
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