Vintage homes for sale & real estate in Osceola County, FL

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NEW 31 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Osceola County, FL:
Excellent opportunity in the heart of Kissimmee! This property offers a prime location with convenient access to Downtown Kissimmee, local government offices, shopping, dining, major roadways, and area amenities. Situated on a spacious lot, the property presents excellent potential for an owner-user, investor, or future redevelopment opportunity. Its central location and surrounding mix of residential and commercial uses make this a unique property with multiple possibilities. Buyer and buyer's agent are responsible for verifying zoning, permitted uses, development potential, lot dimensions, and all information with the appropriate governmental authorities. EXCELLENT INVESTMENT AND REDEVELO

$699,000

4 beds3 baths4,156 sq ft

206 S Vernon Ave, Kissimmee, FL 34741

Spacious lot • 0.63 acre lot • Built 1910

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Osceola County, FL:
LIVE, WORK OR INVEST in DOWNTOWN KISSIMMEE — the choice is yours! This 1923 charmer sits on a corner lot in the heart of Kissimmee and is zoned KRB2, offering the flexibility of a residential/business zoning designation that opens the door to a home office, professional use, or a smart investment play. The 2-bedroom, 1-bath home offers 1,048 sq ft with a spacious 18x14 living room, a generous 11x16 kitchen, a dedicated laundry room, and a welcoming foyer. Outside, you'll find a level, landscaped 0.15-acre lot with a carport, plus a shed and workshop for storage or projects. No HOA, no CDD, and Flood Zone X. Enjoy an unbeatable location in city limits, moments from Downtown Kissimmee's

$250,000

2 beds1 bath1,048 sq ft

213 N Clyde Ave, Kissimmee, FL 34741

Zoned krb2 • Carport • Landscaped lot

ABOUT THIS HOME
Vintage Home for sale in Osceola County, FL:
LOCATION, LOCATION, LOCATION! Welcome to 315 Pennsylvania Avenue, ideally situated in the heart of St. Cloud just blocks from the beautiful St. Cloud Lakefront and minutes from Downtown St. Cloud. This charming 2-bedroom, 1-bath home offers approximately 880 square feet of living space and an opportunity to enjoy one of the city's most convenient and desirable locations. One of the standout features of this property is the BIG, OVERSIZED YARD, providing plenty of outdoor space for entertaining, gardening, pets, recreation, or simply relaxing and enjoying the Florida lifestyle. The location is hard to beat! You're just blocks from the St. Cloud Lakefront beach area, where you can enjoy the w

$229,900

2 beds1 bath880 sq ft

315 Pennsylvania Ave, Saint Cloud, FL 34769

Scenic trails • Oversized yard • Downtown st cloud

ABOUT THIS HOME
Vintage Home for sale in Osceola County, FL:
Investors Do not miss this INCOME PRODUCING OPPORTUNITY! This property was originally designed as a 2-bedroom home and has been thoughtfully converted to offer 4 bedrooms, providing additional flexibility for rental income or multi-generational living. TENANTS IN PLACE, offering the potential for immediate income to a new owner, Conveniently located downtown Kissimmee , walking distance of mayor roads, restaurants, court house, library.

$250,000

2 beds1 bath889 sq ft

721 S Clyde Ave S, Kissimmee, FL 34741

9,322 sq ft lot • Built 1952 • Listed 5 days

ABOUT THIS HOME
Vintage Home for sale in Osceola County, FL:
Investor Special – AS-IS Opportunity in Prime Kissimmee Location! This single-family home is being sold * * AS-IS * * due to prior fire damage and presents a full renovation opportunity for investors or buyers looking to customize from the ground up. The property is a complete rehab and is priced accordingly for those ready to bring their vision to life. Located in a highly desirable area of Kissimmee, this home offers convenient access to major highways including US-192, John Young Parkway, and Osceola Parkway, with quick connections to Florida’s Turnpike and I-4. Enjoy close proximity to world-renowned attractions such as Walt Disney World, as well as shopping, dining, and

$180,000

2 beds2 baths520 sq ft

1705 Evergreen St, Kissimmee, FL 34746

Complete rehab • 0.59 acre lot • Built 1960

Property at 1805 Verona St, Kissimmee, FL 34741, 3 beds, 2 baths

$339,900

3 beds2 baths1,396 sq ft

1805 Verona St, Kissimmee, FL 34741

Property at 1024 Vermont Ave, Saint Cloud, FL 34769, 3 beds, 3 baths

$340,000

3 beds3 baths1,583 sq ft

1024 Vermont Ave, Saint Cloud, FL 34769

Property at 802 Massachusetts Ave, Saint Cloud, FL 34769, 3 beds, 2 baths

$290,000

3 beds2 baths1,060 sq ft

802 Massachusetts Ave, Saint Cloud, FL 34769

Property at 406 E Drury Ave, Kissimmee, FL 34744, 3 beds, 2 baths

$395,000

3 beds2 baths1,895 sq ft

406 E Drury Ave, Kissimmee, FL 34744

Property at 1516 Carolina Ave, Saint Cloud, FL 34769, 3 beds, 2 baths

$300,000

3 beds2 baths1,232 sq ft

1516 Carolina Ave, Saint Cloud, FL 34769

Property at 1622 Tarpon Blvd, Saint Cloud, FL 34771, 2 beds, 1 bath

$159,900

2 beds1 bath768 sq ft

1622 Tarpon Blvd, Saint Cloud, FL 34771

Property at 1000 Delaware Ave, Saint Cloud, FL 34769, 3 beds, 2 baths

$315,000

3 beds2 baths1,272 sq ft

1000 Delaware Ave, Saint Cloud, FL 34769

Property at 725 Mabbette St, Kissimmee, FL 34741, 3 beds, 2 baths

$290,000

3 beds2 baths1,488 sq ft

725 Mabbette St, Kissimmee, FL 34741

Property at 524 & 526 Sumner St, Kissimmee, FL 34741, 4 beds, 2 baths

$440,000

4 beds2 baths1,962 sq ft

524 & 526 Sumner St, Kissimmee, FL 34741

Property at Undisclosed address, Kissimmee, FL 34744, 3 beds, 1.5 baths

$229,000

3 beds1.5 baths960 sq ft

Undisclosed address, Kissimmee, FL 34744

Property at 1103 Brack St, Kissimmee, FL 34744, 5 beds, 3 baths

$368,000

5 beds3 baths1,463 sq ft

1103 Brack St, Kissimmee, FL 34744

Property at 2234 James Dr, Saint Cloud, FL 34771, 3 beds, 3 baths

$389,000

3 beds3 baths1,798 sq ft

2234 James Dr, Saint Cloud, FL 34771

Property at 1515 Indiana Ave, Saint Cloud, FL 34769, 4 beds, 2 baths

$274,900

4 beds2 baths1,542 sq ft

1515 Indiana Ave, Saint Cloud, FL 34769

Property at 501 Mirasol Cir #313, Celebration, FL 34747, 2 beds, 2 baths

$495,000

2 beds2 baths1,488 sq ft

501 Mirasol Cir #313, Celebration, FL 34747

Property at 4870 Lake Cecile Dr, Kissimmee, FL 34746, 4 beds, 2 baths

$399,000

4 beds2 baths2,243 sq ft

4870 Lake Cecile Dr, Kissimmee, FL 34746

Property at 1204 Michigan Ave, Saint Cloud, FL 34769, 3 beds, 1.5 baths

$269,000

3 beds1.5 baths1,748 sq ft

1204 Michigan Ave, Saint Cloud, FL 34769

Property at 2358 Old Dixie Hwy, Kissimmee, FL 34744, 2 beds, 1 bath

$190,000

2 beds1 bath1,232 sq ft

2358 Old Dixie Hwy, Kissimmee, FL 34744

Property at 919 Columbia Ave, Saint Cloud, FL 34769, 4 beds, 1 bath

$224,900

4 beds1 bath986 sq ft

919 Columbia Ave, Saint Cloud, FL 34769

Property at 6281 Bass Hwy, Saint Cloud, FL 34771, 2 beds, 1 bath

$195,000

2 beds1 bath863 sq ft

6281 Bass Hwy, Saint Cloud, FL 34771

Property at 2986 Sun Pointe Ct, Kissimmee, FL 34741, 8 beds, 5 baths

$400,000

8 beds5 baths2,196 sq ft

2986 Sun Pointe Ct, Kissimmee, FL 34741

Property at 211 Lakeshore Blvd, Saint Cloud, FL 34769, 4 beds, 3 baths

$454,999

4 beds3 baths3,632 sq ft

211 Lakeshore Blvd, Saint Cloud, FL 34769

Property at 1216 7th St, Saint Cloud, FL 34769, 2 beds, 2 baths

$276,000

2 beds2 baths819 sq ft

1216 7th St, Saint Cloud, FL 34769

Property at 807 Neptune Rd, Kissimmee, FL 34744, 5 beds, 4 baths

$1,549,000

5 beds4 baths3,992 sq ft

807 Neptune Rd, Kissimmee, FL 34744

Property at 310 E Magnolia St, Kissimmee, FL 34744, 4 beds, 2.5 baths

$275,000

4 beds2.5 baths1,312 sq ft

310 E Magnolia St, Kissimmee, FL 34744

Property at 608 Indiana Ave, Saint Cloud, FL 34769, 3 beds, 2 baths

$299,000

3 beds2 baths1,991 sq ft

608 Indiana Ave, Saint Cloud, FL 34769

Property at 718 Alabama Ave, Saint Cloud, FL 34769, 3 beds, 1 bath

$265,000

3 beds1 bath1,256 sq ft

718 Alabama Ave, Saint Cloud, FL 34769

Property at 200 Lake Marian Rd, Kenansville, FL 34739, 1 bed, 1 bath

$110,000

1 bed1 bath710 sq ft

200 Lake Marian Rd, Kenansville, FL 34739

Property at 1515 Mabbette St, Kissimmee, FL 34741, 4 beds, 3 baths

$340,000

4 beds3 baths1,360 sq ft

1515 Mabbette St, Kissimmee, FL 34741

Property at 3430 5th St, Saint Cloud, FL 34769, 3 beds, 2 baths

$279,900

3 beds2 baths1,528 sq ft

3430 5th St, Saint Cloud, FL 34769

Property at 817 Ohio Ave, Saint Cloud, FL 34769, 4 beds, 2 baths

$399,000

4 beds2 baths1,950 sq ft

817 Ohio Ave, Saint Cloud, FL 34769

Property at 9010 Concord Rd, Saint Cloud, FL 34773, 3 beds, 3 baths

$208,000

3 beds3 baths1,428 sq ft

9010 Concord Rd, Saint Cloud, FL 34773

Property at 1417 11th St, Saint Cloud, FL 34769, 2 beds, 1 bath

$239,000

2 beds1 bath788 sq ft

1417 11th St, Saint Cloud, FL 34769

Property at 2615 N Beaumont Ave, Kissimmee, FL 34741, 4 beds, 2 baths

$315,000

4 beds2 baths1,280 sq ft

2615 N Beaumont Ave, Kissimmee, FL 34741

Property at 6370 Bass Hwy, Saint Cloud, FL 34771, 3 beds, 2 baths

$281,000

3 beds2 baths1,175 sq ft

6370 Bass Hwy, Saint Cloud, FL 34771

Property at 515 New York Ave, Saint Cloud, FL 34769, 2 beds, 1 bath

$269,000

2 beds1 bath1,095 sq ft

515 New York Ave, Saint Cloud, FL 34769

Property at 518 Tohopekaliga Ave, Kissimmee, FL 34744, 4 beds, 2 baths

$435,000

4 beds2 baths1,952 sq ft

518 Tohopekaliga Ave, Kissimmee, FL 34744

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Based on information submitted to the MLS GRID as of Sun Oct 04 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in Osceola County

There are currently 65 vintage homes for sale in Osceola County at a median listing price of $400K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Osceola County stay on the market for 104 days and receive 1 offers. This map is refreshed with the newest listings in Osceola County every 15 minutes.

In the past month, 700 homes have been sold in Osceola County. In addition to houses in Osceola County, there were also 725 condos, 1258 townhouses, and 18 multi-family units for sale in Osceola County last month. Find your dream home in Osceola County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Osceola County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Osceola County. If you're looking to sell your home in the Osceola County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Osceola County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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