Highland Village Winter Springs

In This Community
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Highland Village is a community of single family homes in Winter Springs, Florida, with a range of options priced between $75,000 and $425,000. The smallest Highland Village home in the community is a three bedroom two bathroom residence that is 974 square feet, and the largest of the Highland Village homes has three beds and two baths and is a 3,565 square foot (2,671SF Under Air) residence.

Property management fees in Seminole County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Highland Village are $75. Please check the individual listing pages for the exact homeowners association fees for a particular Highland Village home.

There are four commercial airports that serve Highland Village - Orlando Sanford International (SFB), which is seven miles away; Orlando Executive (ORL), which is eleven miles away; Orlando International (MCO), which is nineteen miles away, and Kissimmee Gateway (ISM), which is 30 miles away from Highland Village.

In addition, there are numerous other communities in Winter Springs to choose from, or you may browse all available Winter Springs Real Estate, including some new construction opportunities. Homes for sale in Highland Village are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Highland Village hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Florida real estate needs.

Highland Village Homes For Sale

355 Highland Village Ct, WINTER SPRINGS
SOLD 12/30/16
$199,900

MLS#MFRO5478007

355 Highland Village Ct
Winter Springs, FL 32708

3

2

2

1,845 SqFt

Pool

0.12 Acres

357 Highland Village Ct , WINTER SPRINGS
SOLD 09/11/15
$164,900

MLS#MFRO5384275

357 Highland Village Ct
Winter Springs, FL 32708

3

2

2

2,010 SqFt

0.11 Acres

305 Kirkcaldy Dr, WINTER SPRINGS
SOLD 10/29/24
$300,000

MLS#MFRO6242136

305 Kirkcaldy Dr
Winter Springs, FL 32708

3

2

1,317 SqFt

0.11 Acres

305 Kirkcaldy Dr, WINTER SPRINGS
SOLD 06/05/12
$75,000

MLS#MFRO5092563

305 Kirkcaldy Dr
Winter Springs, FL 32708

3

2

1,403 SqFt

0.11 Acres

307 Kirkcaldy Dr, WINTER SPRINGS
SOLD 07/15/16
$139,500

MLS#MFRO5443525

307 Kirkcaldy Dr
Winter Springs, FL 32708

3

3

1,580 SqFt

0.11 Acres

307 Kirkcaldy Dr, WINTER SPRINGS
SOLD 05/21/12
$89,500

MLS#MFRO5092942

307 Kirkcaldy Dr
Winter Springs, FL 32708

3

3

1,580 SqFt

0.11 Acres

309 Kirkcaldy Dr, WINTER SPRINGS
SOLD 09/03/25
$300,000

MLS#MFRO6315903

309 Kirkcaldy Dr
Winter Springs, FL 32708

3

2

1,526 SqFt

0.11 Acres

309 Kirkcaldy Dr, WINTER SPRINGS
SOLD 08/25/16
$139,000

MLS#MFRO5456545

309 Kirkcaldy Dr
Winter Springs, FL 32708

3

2

1,526 SqFt

0.11 Acres

317 Kirkcaldy Dr, WINTER SPRINGS
SOLD 05/11/22
$325,000

MLS#MFRO6015876

317 Kirkcaldy Dr
Winter Springs, FL 32708

2

2

2

1,989 SqFt

0.11 Acres

319 Kirkcaldy Dr, WINTER SPRINGS
SOLD 10/24/24
$335,800
$345,800

MLS#MFRO6237246

319 Kirkcaldy Dr
Winter Springs, FL 32708

3

2

1

1,811 SqFt

0.12 Acres

321 Kirkcaldy Dr , WINTER SPRINGS
SOLD 12/18/14
$139,500

MLS#MFRU7712109

321 Kirkcaldy Dr
Winter Springs, FL 32708

2

2

1

1,900 SqFt

0.15 Acres

321 Kirkcaldy Dr, WINTER SPRINGS
SOLD 06/30/17
$179,900

MLS#MFRO5507236

321 Kirkcaldy Dr
Winter Springs, FL 32708

2

2

1

1,900 SqFt

0.15 Acres

308 Macgregor Rd , WINTER SPRINGS
SOLD 12/10/12
$125,000
$12,500,000

MLS#MFRT2529114

308 Macgregor Rd
Winter Springs, FL 32708

3

2

2

1,981 SqFt

0.12 Acres

310 Macgregor Road, WINTER SPRINGS
SOLD 12/01/22
$385,000

MLS#MFRO6068690

310 Macgregor Road
Winter Springs, FL 32708

3

3

2

2,565 SqFt

0.12 Acres

327 Kirkcaldy Dr, WINTER SPRINGS
SOLD 11/22/16
$179,900

MLS#MFRS4836786

327 Kirkcaldy Dr
Winter Springs, FL 32708

2

2

1

1,837 SqFt

0.12 Acres

324 Kirkcaldy Dr , WINTER SPRINGS
SOLD 09/15/15
$164,900

MLS#MFRO5382132

324 Kirkcaldy Dr
Winter Springs, FL 32708

3

2

1,797 SqFt

0.13 Acres

324 Kirkcaldy Dr, WINTER SPRINGS
SOLD 07/25/17
$175,000

MLS#MFRO5519704

324 Kirkcaldy Dr
Winter Springs, FL 32708

3

2

1,797 SqFt

0.13 Acres

326 Kirkcaldy Dr , WINTER SPRINGS
SOLD 07/20/15
$149,900
$175,000

MLS#MFRO5363223

326 Kirkcaldy Dr
Winter Springs, FL 32708

3

2

1,472 SqFt

0.14 Acres

314 Macgregor Rd, WINTER SPRINGS
SOLD 02/13/25
$375,000

MLS#MFRO6265396

314 Macgregor Rd
Winter Springs, FL 32708

3

2

2

2,176 SqFt

0.12 Acres

335 Kirkcaldy Dr , WINTER SPRINGS
SOLD 05/23/14
$95,000

MLS#MFRS4726201

335 Kirkcaldy Dr
Winter Springs, FL 32708

3

2

1,440 SqFt

0.11 Acres

335 Kirkcaldy Dr, WINTER SPRINGS
SOLD 12/20/24
$323,000
$329,800

MLS#MFRO6237825

335 Kirkcaldy Dr
Winter Springs, FL 32708

3

2

1,440 SqFt

0.11 Acres

337 Kirkcaldy Dr , WINTER SPRINGS
SOLD 09/26/14
$117,500
$122,000

MLS#MFRO5304033

337 Kirkcaldy Dr
Winter Springs, FL 32708

2

2

1,042 SqFt

0.11 Acres

337 Kirkcaldy Dr, WINTER SPRINGS
SOLD 06/28/24
$299,000
$300,000

MLS#MFRO6191333

337 Kirkcaldy Dr
Winter Springs, FL 32708

2

2

1,042 SqFt

0.11 Acres

341 Kirkcaldy Dr, WINTER SPRINGS
SOLD 06/12/25
$290,000
$306,000

MLS#MFRO6294275

341 Kirkcaldy Dr
Winter Springs, FL 32708

2

2

974 SqFt

0.15 Acres


We do not have any properties available for sale in Highland Village.
You may also be interested in Highland Village in Deerfield Beach.

What schools are Highland Village homes zoned for?

Where you live in Winter Springs determines which public schools your children may attend, which directly influences home values. Homes in Highland Village are zoned for the following Seminole County school districts, making school zone boundaries a key factor in property desirability and market demand.

Middle

Unknown

High School

Unknown

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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