Vintage homes for sale & real estate in 34744, FL

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ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
Excellent single family. Located in Kissimmee near shopping , schools and hospital. 2 bed rooms 1 full bath porch and much more . Priced to sell. Call to make an appointment .

$197,000

2 beds1 bath744 sq ft

1418 Bay St, Kissimmee, FL 34744

Near schools • Near hospital • Single family

FOR SALE BY OWNER

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
HOUSE FOR SALE CUTE & COZY 2 BR / 2 BATH (KISSIMMEE) Why rent an apartment or condo when you can have your own private home. Nice 2/2 in central Kissimmee. Fresh paint, all tile floors. Huge fenced yard. All kitchen appliances provided including washer and dryer. Huge fenced yard. NO HOA! Walking distance to shopping and restaurants. Easy access to major highways 417 / Turnpike / i-4 / Osceola Pkwy / 192 /OBT close to airport, Disney and attractions. Don't miss it will not last! Please call or TEXT if you would like to schedule a showing. * Please be advised that Sellers are both Florida Licensed Real Estate Associates.

$234,900

2 beds2 baths768 sq ft

314 E Fletcher St, Kissimmee, FL 34744

Fenced yard • 6,970 sq ft lot • Built 1957

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
TROPICAL LAKEFRONT OASIS with GUEST COTTAGE on 1.64 acres - No HOA + 2 Large DETACHED GARAGES(3 Bays) and WORKSHOP. Escape to this beautifully updated 4-bedroom, 3-bath single-story home + Cottage situated on a true lakefront lot along the private shores of Fish Lake. The main home features 2,556 sq ft of living space (5,396 sq ft under roof), thoughtfully designed with natural light, soothing colors, and warm finishes throughout. The open-concept layout flows seamlessly for everyday living and entertaining, while the home’s tasteful updates and abundant windows create a serene, welcoming atmosphere. A fully equipped detached guest cottage includes its own kitchen and offers excellent

$749,900

4 beds3 baths2,556 sq ft

2571 Ames Haven Rd, Kissimmee, FL 34744

Lakefront lot • Recent upgrades • Guest cottage

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
Motivated Seller! Welcome home to this charming 3 bedroom, 2 bath, split plan that sits on an oversized, corner lot with a view of a pond in the Kissimmee Lakefront neighborhood! The living room, dining room and family room boast 3/4" hickory wood flooring. The living room windows are from the Kissimmee Train Station per the owner! The family room has a wood burning fireplace. The kitchen has butcher block countertops with smart appliances and a new dishwasher. The master suite is a hotel type suite with a combo bedroom, closet and bath. A tankless hot water heater was installed in 2024. The main house roof, gutters and soffit were replaced in 2024. A security gate and fenced yard

$399,000

3 beds2 baths1,528 sq ft

302 E Drury Ave, Kissimmee, FL 34744

Smart appliances • View of a pond • Corner lot

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
Charming Starter Home on Spacious Lot! Discover this cozy 2-bedroom, 2-bathroom mobile home at 410 Still St, offering 960 sq ft of comfortable living space on a generous 7,013 sq ft lot. Built in 1960, this home presents a unique opportunity for first-time buyers or investors looking to personalize a classic property. Enjoy the open potential of the lot for outdoor activities, gardening, or future expansions.

$299,000

2 beds1.5 baths960 sq ft

410 Still St, Kissimmee, FL 34744

Future expansions • Gardening • Spacious lot

Property at 1137 Shawnee Dr, Kissimmee, FL 34744, 2 beds, 1 bath

$257,000

2 beds1 bath684 sq ft

1137 Shawnee Dr, Kissimmee, FL 34744

Property at 107 Dellwood Dr, Kissimmee, FL 34744, 3 beds, 1.5 baths

$329,999

3 beds1.5 baths1,374 sq ft

107 Dellwood Dr, Kissimmee, FL 34744

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ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
Escape to your own slice of paradise with this beautiful home situated on over half an acre directly on East Lake Toho. This property is perfect for outdoor enthusiasts and anyone looking to unwind. Enjoy the all St. Cloud Lakefront events from your back yard! Fireworks and Festivals, oh my! This charming residence boasts 3 spacious bedrooms and 2 elegantly redesigned bathrooms, combining comfort with modern style. The upgraded kitchen features exquisite stone countertops and stainless steel appliances, ideal for culinary adventures and gatherings. Enjoy seamless indoor outdoor living with brand new French doors off the family room, office, and primary bedroom, flooding the space with natu

$670,700

3 beds2 baths2,252 sq ft

4321 Rummell Rd, Saint Cloud, FL 34769

Over half an acre • Lakefront events • Stone countertops

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
This investor property offers two bedrooms and two bathrooms with 1,119 square feet of interior living space. The kitchen and dining area feature an open-concept layout with wooden cabinetry, and the home includes a dedicated laundry area for added convenience. Situated on a corner lot, the property features a front patio and open space at the rear, providing flexibility for outdoor use or future improvements. A detached one-car garage offers additional storage space. The property is in need of roof, ceiling, and general TLC repairs, presenting an excellent opportunity for renovation.

$184,500

2 beds2 baths1,119 sq ft

1200 Massachusetts Ave, Saint Cloud, FL 34769

Front patio • Corner lot • Open-concept layout

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
Welcome to 1121 Illinois Ave, a renovated and remodeled 5-bedroom, 2-bathroom home located in one of St. Cloud’s most convenient and charming areas. This home offers a well-designed, functional layout where the living room, dining area, and kitchen flow together seamlessly, creating an inviting space for everyday living. The kitchen features stainless steel appliances and ample cabinet storage, making it both practical and efficient. Each of the five bedrooms is generously sized, providing flexibility for a variety of living needs, including guest space, home offices, or multi-purpose rooms. Situated on an oversized corner lot sitting on over 1/4 acre, the fully fenced yard offers ple

$325,000

5 beds2 baths1,379 sq ft

1121 Illinois Ave, Saint Cloud, FL 34769

Oversized corner lot • Functional layout • Fully fenced yard

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
The one you have been waiting for. Located in downtown Saint cloud, one of central Floridas fastest growing communities, just minutes from world renowned lakes, Lake Nona, Orlando Airport, and a short drive to Disney and Universal this multi-unit property is bursting with value. Situated on over a 1/3rd acre corner lot, this property features two seperate units with separate addresses and utilities. The main residence is an updated 3/2, the ADU is a 1/1 also updated. Through the front door of the main residence, an open and airy floor plan greets you bursting with natural light onto the refinished wood floors. To the left, a huge living room is perfect for family gatherings. To the right th

$519,900

4 beds3 baths2,288 sq ft

1020 Wisconsin Ave, Saint Cloud, FL 34769

Two separate units • Large living room • Updated kitchen

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
Welcome to 2331 W Oak St in the heart of Kissimmee! This charming 3-bedroom, 1-bath home plus a separate 1/1 unit offers fantastic flexibility—perfect for extended family, guests, or potential rental income. Enjoy peace of mind with impact windows, a 2020 roof, and a whole-home water softener. The updated kitchen features modern finishes and a bright, functional layout. Outside, the property boasts a spacious backyard and covered areas ideal for gatherings, cookouts, and outdoor entertainment. Located just minutes from world-famous Disney parks, major roads, shopping, dining, and all that Central Florida has. Don’t miss this versatile and move-in ready opportunity!

$334,900

4 beds2 baths1,335 sq ft

2331 W Oak St, Kissimmee, FL 34741

Covered areas • Spacious backyard • 2020 roof

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
WELCOME HOME—WHERE CHARACTER, SUNLIGHT, AND USABILITY COME TOGETHER IN THE HEART OF KISSIMMEE! This charming 2-BEDROOM, 1-BATHROOM HOME offers a warm and inviting atmosphere from the moment you step inside. The ORIGINAL WOOD FLOORS add timeless appeal, while the UPDATED WALK-IN SHOWER brings a modern touch to the bathroom. Need a little extra space? You’ll love the ADDITIONAL ROOM, perfect for use as a DEN, STUDY, HOBBY ROOM, OR EVEN A THIRD BEDROOM—flexibility that adapts to your lifestyle. One of the standout features of this home is the bright and airy FLORIDA ROOM, drenched in natural light and ideal for relaxing, entertaining, or enjoying morning coffee. Step outside

$270,000

2 beds1 bath1,104 sq ft

903 N Forrest Ave, Kissimmee, FL 34741

Rv parking • Additional room • Florida room

Property at 704 Mississippi Ave, Saint Cloud, FL 34769, 1 bed, 1 bath

$239,000

1 bed1 bath843 sq ft

704 Mississippi Ave, Saint Cloud, FL 34769

Property at 1010 Mississippi Ave, Saint Cloud, FL 34769, 2 beds, 2 baths

$349,999

2 beds2 baths1,124 sq ft

1010 Mississippi Ave, Saint Cloud, FL 34769

Property at 305 E Miami Ter, Kissimmee, FL 34741, 2 beds, 2 baths

$220,990

2 beds2 baths970 sq ft

305 E Miami Ter, Kissimmee, FL 34741

Property at 1200 Connecticut Ave, Saint Cloud, FL 34769, 3 beds, 1.5 baths

$279,900

3 beds1.5 baths1,821 sq ft

1200 Connecticut Ave, Saint Cloud, FL 34769

Property at 420 Jacks Memorial Rd, Saint Cloud, FL 34769, 4 beds, 3 baths

$499,900

4 beds3 baths2,502 sq ft

420 Jacks Memorial Rd, Saint Cloud, FL 34769

Property at 2515 N Beaumont Ave, Kissimmee, FL 34741, 3 beds, 1 bath

$269,900

3 beds1 bath984 sq ft

2515 N Beaumont Ave, Kissimmee, FL 34741

Property at 1317 W Emmett St, Kissimmee, FL 34741, 2 beds, 2 baths

$315,000

2 beds2 baths825 sq ft

1317 W Emmett St, Kissimmee, FL 34741

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

$600,000

4 beds2 baths1,950 sq ft

817 Ohio Ave, Saint Cloud, FL 34769

Property at 1705 Delaware Ave, Saint Cloud, FL 34769, 1 bed, 1 bath

$240,000

1 bed1 bath700 sq ft

1705 Delaware Ave, Saint Cloud, FL 34769

Property at 22 S Clyde Ave, Kissimmee, FL 34741, 9 beds, 6 baths

$1,100,000

9 beds6 baths4,685 sq ft

22 S Clyde Ave, Kissimmee, FL 34741

Property at 1905 Emmett St, Kissimmee, FL 34741, 2 beds, 1 bath

$299,000

2 beds1 bath1,124 sq ft

1905 Emmett St, Kissimmee, FL 34741

Property at 658 Hudson St, Kissimmee, FL 34741, 3 beds, 1 bath

$279,000

3 beds1 bath1,176 sq ft

658 Hudson St, Kissimmee, FL 34741

Property at 1614 Verona St, Kissimmee, FL 34741, 3 beds, 1 bath

$270,000

3 beds1 bath1,086 sq ft

1614 Verona St, Kissimmee, FL 34741

Property at 1416 Ohio Ave, Saint Cloud, FL 34769, 3 beds, 2 baths

$359,000

3 beds2 baths1,492 sq ft

1416 Ohio Ave, Saint Cloud, FL 34769

Based on information submitted to the MLS GRID as of Sun Jan 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 34744

There are currently 7 vintage homes for sale in 34744 at a median listing price of $427K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 34744 stay on the market for 97 days and receive 4 offers. This map is refreshed with the newest listings in 34744 every 15 minutes.

In the past month, 64 homes have been sold in 34744. In addition to houses in 34744, there were also 5 condos, 53 townhouses, and 1 multi-family unit for sale in 34744 last month. Find your dream home in 34744 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 34744 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 34744. If you're looking to sell your home in the 34744 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 34744 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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