Search Orlando Gated Homes for Sale, $400,000 - $500,000

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Active 3251 Pinewood Ct, KISSIMMEE

$449,900

PLEASANT HILL LAKES UNIT 08

3251 Pinewood Ct, KISSIMMEE

3 Beds 2 Baths 2,404 SqFt Residential Single Family Residence MLS® # O6427499
Active 6376 Shimmering Shores Ln, ST CLOUD

$449,900

▼ $5,000 DEL WEBB SUNBRIDGE

6376 Shimmering Shores Ln, ST CLOUD

2 Beds 2 Baths 1,781 SqFt Residential Single Family Residence MLS® # O6334315
Active 5063 Hatchineha Ct, ST CLOUD

$449,900

▼ $40,100 HANOVER LAKES PH 4

5063 Hatchineha Ct, ST CLOUD

4 Beds 3 Baths 2,580 SqFt Residential Single Family Residence MLS® # O6433284
Active 9181 Oscraft Dr, DAVENPORT

$449,900

BELLAVIVA PH 2

9181 Oscraft Dr, DAVENPORT

4 Beds 2 Baths 1,918 SqFt Residential Single Family Residence MLS® # S5154827
Active 3949 Baja Dr, ST CLOUD

$449,900

▼ $10,000 WHALEYS CREEK PH 1

3949 Baja Dr, ST CLOUD

4 Beds 4 Baths 2,820 SqFt Residential Single Family Residence MLS® # S5156639
Active 3200 Winged Foot Rd, MOUNT DORA

$449,900

▼ $7,600 MOUNT DORA WOLF CREEK RIDGE PH 01

3200 Winged Foot Rd, MOUNT DORA

4 Beds 4 Baths 2,700 SqFt Residential Single Family Residence MLS® # G5111832
Active S 14th St, LEESBURG

$449,900

▼ $30,000

S 14th St, LEESBURG

0 Beds 0 Baths 0 SqFt Land Land MLS® # G5099473
Active 3251 Secret Lake Dr 1214, KISSIMMEE

$449,900

▲ $5,000 AMBAR RESIDENCES

3251 Secret Lake Dr 1214, KISSIMMEE

1 Bed 1 Bath 656 SqFt Residential Condo - Hotel MLS® # O6353437
Active 10294 Merrymeeting Bay Dr, WINTER GARDEN

$449,900

▼ $10,000 WATERLEIGH PH 2C-1

10294 Merrymeeting Bay Dr, WINTER GARDEN

3 Beds 2 Baths 1,689 SqFt Residential Single Family Residence MLS® # O6407798
Active Barn St, KISSIMMEE

$449,900

▼ $146,099 MARYDIA

Barn St, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land Land MLS® # S5143269
Active 146 Bayswater Ln, DAVENPORT

$449,880

VILLAS OF WESTRIDGE PH 5A

146 Bayswater Ln, DAVENPORT

4 Beds 3 Baths 1,596 SqFt Residential Single Family Residence MLS® # O6429749
Active 436 Ocean Course Ave, DAVENPORT

$449,800

STONEYBROOK SOUTH NORTH PRCL PH 1

436 Ocean Course Ave, DAVENPORT

4 Beds 3 Baths 1,914 SqFt Residential Townhouse MLS® # O6356961
Active 3001 Mandolin Dr, KISSIMMEE

$449,777

▼ $10,123 TURNBERRY RESERVE UNIT 1

3001 Mandolin Dr, KISSIMMEE

4 Beds 3 Baths 2,392 SqFt Residential Single Family Residence MLS® # S5139386
Active 4944 Cucumber St, LAKELAND

$449,770

▼ $6,000 HAWTHORNE PHASE 2A-2B

4944 Cucumber St, LAKELAND

3 Beds 3 Baths 2,230 SqFt Residential Single Family Residence MLS® # TB8517662
Active 1495 Skyline Dr, KISSIMMEE

$449,750

▼ $150 HARBOUR OAKS UNIT 1

1495 Skyline Dr, KISSIMMEE

3 Beds 2 Baths 2,094 SqFt Residential Single Family Residence MLS® # S5145209
New
Active 4425 Juliana Lake Dr, AUBURNDALE

$449,665

LAKE JULIANA ESTATES

4425 Juliana Lake Dr, AUBURNDALE

4 Beds 3 Baths 2,200 SqFt Residential Single Family Residence MLS® # L4965026
New
Active 4508 Grandview Glen Dr, AUBURNDALE

$449,665

LAKE JULIANA ESTATES

4508 Grandview Glen Dr, AUBURNDALE

4 Beds 3 Baths 2,200 SqFt Residential Single Family Residence MLS® # L4965023
Active 713 Newell Hill Rd, LEESBURG

$449,500

▼ $5,500 LEESBURG MAJESTIC OAKS LANDING

713 Newell Hill Rd, LEESBURG

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6297419
Active 2765 Carrickton Cir, ORLANDO

$449,500

WYNDHAM LAKES ESTATES

2765 Carrickton Cir, ORLANDO

4 Beds 3 Baths 2,027 SqFt Residential Single Family Residence MLS® # O6409680
Active 2230 W Helen Cir, BARTOW

$449,500

▼ $8,000 LA HACIENDA

2230 W Helen Cir, BARTOW

4 Beds 3 Baths 2,593 SqFt Residential Single Family Residence MLS® # L4961348
Active 4900 Lotta Ct, ST CLOUD

$449,500

HANOVER LAKES PH 3

4900 Lotta Ct, ST CLOUD

3 Beds 2 Baths 1,957 SqFt Residential Single Family Residence MLS® # O6374765
Active 1352 Errol Pkwy, APOPKA

$449,500

▼ $15,500 ERROL ESTATE

1352 Errol Pkwy, APOPKA

3 Beds 2 Baths 2,525 SqFt Residential Single Family Residence MLS® # O6396352
Active 439 Virginia Ave, ST CLOUD

$449,500

▼ $30,000 ST CLOUD 2ND TOWN OF

439 Virginia Ave, ST CLOUD

3 Beds 2 Baths 2,160 SqFt Residential Single Family Residence MLS® # O6399995
Active 9362 Woodcrane Dr, WINTER GARDEN

$449,300

▼ $10,000 WATERMARK PH 1B

9362 Woodcrane Dr, WINTER GARDEN

3 Beds 3 Baths 2,058 SqFt Residential Single Family Residence MLS® # O6417277
New
Active 12333 Via Derna Pl, WINDERMERE

$449,000

CARRINGTON

12333 Via Derna Pl, WINDERMERE

3 Beds 3 Baths 1,919 SqFt Residential Townhouse MLS® # O6441184
Active 279 Brookshire Dr, LAKE WALES

$449,000

BROOKSHIRE

279 Brookshire Dr, LAKE WALES

5 Beds 4 Baths 3,732 SqFt Residential Single Family Residence MLS® # L4964783
Active Jessica Ct, WINTER PARK

$449,000

Jessica Ct, WINTER PARK

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6419256
Active 213 Willow View Dr, DAVENPORT

$449,000

▼ $10,000 WINDWOOD BAY PH 02

213 Willow View Dr, DAVENPORT

4 Beds 4 Baths 2,676 SqFt Residential Single Family Residence MLS® # O6400714
Active 7667 Otterspool St, KISSIMMEE

$449,000

WINDSOR HILLS PH 2

7667 Otterspool St, KISSIMMEE

3 Beds 3 Baths 1,440 SqFt Residential Townhouse MLS® # S5151169
Active 519 Vigo St, DAVENPORT

$449,000

DEL WEBB ORLANDO/RIDGEWOOD LKS-PH 2 VILLAGE 14

519 Vigo St, DAVENPORT

3 Beds 2 Baths 2,320 SqFt Residential Single Family Residence MLS® # S5154864
Active 3828 Sagefield Dr, HARMONY

$449,000

HARMONY CENTRAL PH 1

3828 Sagefield Dr, HARMONY

4 Beds 4 Baths 2,314 SqFt Residential Single Family Residence MLS® # O6365461
Active 3561 Ventura Club Cir, ORLANDO

$449,000

VENTURA CLUB

3561 Ventura Club Cir, ORLANDO

4 Beds 3 Baths 2,074 SqFt Residential Single Family Residence MLS® # O6377549
Active 10548 Flowers Ave, ORLANDO

$449,000

ORLANDO IMPROV CO 02

10548 Flowers Ave, ORLANDO

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6367770
Active 6809 Serpent Hawk Ln, HOWEY IN THE HILLS

$449,000

EAGLETAIL LNDG PH 2

6809 Serpent Hawk Ln, HOWEY IN THE HILLS

5 Beds 3 Baths 2,974 SqFt Residential Single Family Residence MLS® # G5114754
Active 6644 Great Bear Dr, LAKELAND

$449,000

VILLAGES/BRIDGEWATER-VLG 14

6644 Great Bear Dr, LAKELAND

5 Beds 3 Baths 2,490 SqFt Residential Single Family Residence MLS® # O6438493
Active 7430 Bear Claw Rn, ORLANDO

$449,000

CHICKASAW PLACE

7430 Bear Claw Rn, ORLANDO

4 Beds 4 Baths 2,384 SqFt Residential Single Family Residence MLS® # O6385029
Active 1357 Darnaby Way, ORLANDO

$449,000

▼ $10,000 HARBOR LAKES 50 77

1357 Darnaby Way, ORLANDO

4 Beds 4 Baths 2,561 SqFt Residential Single Family Residence MLS® # S5152242
Open House
Active 3202 Tradewinds Tr, ORLANDO

$449,000

▼ $10,900 ISLE CATALINA

3202 Tradewinds Tr, ORLANDO

3 Beds 3 Baths 1,667 SqFt Residential
Tue, Sep 15th, 2026 @ 12:30pm - 2:30pm
Single Family Residence MLS® # O6436772
Active 2639 Candied Apple Alley, KISSIMMEE

$449,000

TOHOQUA PH 7

2639 Candied Apple Alley, KISSIMMEE

3 Beds 3 Baths 1,755 SqFt Residential Townhouse MLS® # O6394670
Active 1877 Summer Serenity Dr, KISSIMMEE

$449,000

▼ $14,000 TOHOQUA PH 4A

1877 Summer Serenity Dr, KISSIMMEE

4 Beds 3 Baths 2,776 SqFt Residential Single Family Residence MLS® # O6354995
Active 542 S Osceola Ave 34, ORLANDO

$449,000

CHEROKEE PLACE CONDO PH 01

542 S Osceola Ave 34, ORLANDO

2 Beds 3 Baths 1,637 SqFt Residential Condominium MLS® # V4948949
Active 1013 Sadie Ridge Rd, CLERMONT

$449,000

▼ $8,500 HIGHLAND RANCH/CANYONS PH 2

1013 Sadie Ridge Rd, CLERMONT

4 Beds 2 Baths 1,846 SqFt Residential Single Family Residence MLS® # G5113221
Active 4258 Twisted Twig Bnd, KISSIMMEE

$449,000

STOREY CREEK

4258 Twisted Twig Bnd, KISSIMMEE

5 Beds 3 Baths 2,388 SqFt Residential Single Family Residence MLS® # S5152122
Active 305 S Rossiter St, MOUNT DORA

$449,000

MOUNT DORA OAKWOOD

305 S Rossiter St, MOUNT DORA

3 Beds 2 Baths 2,072 SqFt Residential Single Family Residence MLS® # V4950661
Active 14014 Scarlet Aster Alley, WINTER GARDEN

$449,000

▼ $6,000 HARVEST/OVATION

14014 Scarlet Aster Alley, WINTER GARDEN

3 Beds 3 Baths 1,808 SqFt Residential Townhouse MLS® # O6418814
Active 3936 Fescue St, CLERMONT

$449,000

▼ $6,000 SAWGRASS BAY PH 3B

3936 Fescue St, CLERMONT

4 Beds 3 Baths 2,240 SqFt Residential Single Family Residence MLS® # O6405477
Active 7327 Millstone St, WINDERMERE

$449,000

▼ $10,000 LAKE BURDEN SOUTH PH I

7327 Millstone St, WINDERMERE

3 Beds 3 Baths 1,531 SqFt Residential Townhouse MLS® # O6397203
Active 608 S Main Ave 35, MINNEOLA

$449,000

▼ $26,000 MINNEOLA OAKS CONDO

608 S Main Ave 35, MINNEOLA

2 Beds 2 Baths 1,674 SqFt Residential Condominium MLS® # G5115322