Vintage homes for sale & real estate in 34744, FL

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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:
$20k Price Reduction!!! Welcome to this charming Kissimmee home! Freshly painted and move-in ready, this property features a practical and cozy layout, with an additional room that includes its own bath — perfect for guests, a home office, or a private retreat. Recent updates include a new roof (2022), updated plumbing, and A/C maintenance completed in 2025, ensuring peace of mind for years to come. Step outside to a spacious backyard where you’ll find a tiny home ready to rent—perfect for generating extra income thanks to the property’s no HOA location. The outdoor space also offers plenty of room for gatherings, gardening, or simply enjoying Florida’s sunshi

$257,000

2 beds1 bath684 sq ft

1137 Shawnee Dr, Kissimmee, FL 34744

No hoa location • Spacious backyard • Additional room

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

$849,000

4 beds3 baths2,556 sq ft

2571 Ames Haven Rd, Kissimmee, FL 34744

Lakefront lot • Recent upgrades • Guest cottage

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
Welcome to 107 Dellwood! This Pool home offers 3 bedrooms, 1.5 baths, plus two versatile bonus rooms that can be used as additional bedrooms, a home office, or a gym. The spacious layout provides endless possibilities—ideal for a growing household or an investor looking to rent out individual rooms. The backyard is perfect for entertaining, complete with a pool for those warm summer days. Don’t miss the opportunity to own this flexible and functional property!

$329,999

3 beds1.5 baths1,374 sq ft

107 Dellwood Dr, Kissimmee, FL 34744

Bonus rooms • Pool home • 0.24 acre 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.

$325,000

2 beds1.5 baths960 sq ft

410 Still St, Kissimmee, FL 34744

Future expansions • Gardening • Spacious lot

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ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
Discover this move-in-ready and beautifully renovated 2-bedroom, 2-bath bungalow situated on an oversized lot in the heart of St. Cloud. Completely updated in 2017, this home offers comfort, functionality, and impressive outdoor amenities ideal for everyday living or accommodating recreational vehicles and storage needs. Inside, you’ll find a well-appointed kitchen with granite countertops, name-brand stainless steel appliances, and attractive finishes throughout. Each bedroom features its own private bathroom, providing convenience and privacy. The home also includes a spacious bonus room, perfect for an office, hobby room, fitness space, or additional living area. Custom details&mda

$349,999

2 beds2 baths1,124 sq ft

1010 Mississippi Ave, Saint Cloud, FL 34769

Spacious bonus room • Dedicated workshop • Private bathroom

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
GREAT INVESTMENT OPPORTUNITY This house is tenant-occupied under a month-to-month agreement. The main home features 2 bedrooms and 1 bathroom. At the back of the property, there is a 1-bedroom, 1-bathroom suite that has been FULLY REMODELED. Buyer is responsible for conducting their own due diligence regarding square footage, lot size, room dimensions, and taxes.

$220,990

2 beds2 baths970 sq ft

305 E Miami Ter, Kissimmee, FL 34741

9,365 sq ft lot • Built 1960 • Listed 4 days

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
Discover the potential in this long-time family home, offering 3 comfortable bedrooms, 1 bath, a spacious utility room, and the freedom of no HOA. With many major mechanicals already updated, a new A/C 2.5-ton unit installed in 4/2024, a second electrical panel replaced in 2022, a complete roof in 2017, new beams and a re-roof over bedroom #3 in 8/2025, and a full sewer repipe from the home to the main in 10/2022, the heavy lifting has been done for you. Additional updates include a brand-new stove, new windows, a newly redone shower, refreshed landscaping, and exterior paint in 2024. The backyard is also fully fenced and has a large storage shed. Filled with years of memories and ready for

$240,000

3 beds1 bath1,224 sq ft

1819 Verona St, Kissimmee, FL 34741

New beams • Full sewer repipe • Complete roof

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
Attention all entrepreneurs and commercial business owners, you will NOT want to miss this great opportunity! This building is minutes away from the heart of St Cloud's thriving downtown district. LOCATION LOCATION LOCATION. .. DENTAL - MEDICAL - RESTAURANT - RETAIL - PROFESSIONAL OFFICE - CHILD CARE - REPAIR SHOP endless opportunities. Large adjacent lot provides ample opportunity to grow your business. One block off 192, close to restaurants, banks, hospitals, lake shore, night life, and lots of space for parking. Act now and purchase or lease with an option to purcahse a premier location in Osceola's best kept secret - St Cloud's State Streets. Property can be occupied as a residence whi

$279,900

3 beds1.5 baths1,821 sq ft

1200 Connecticut Ave, Saint Cloud, FL 34769

Large adjacent lot • One block off 192 • Close to restaurants

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
One or more photo(s) has been virtually staged. Discover the perfect blend of space, privacy, and flexibility in this beautifully expanded one-story home on 1.18 acres in St. Cloud. Originally built in 1925 and thoughtfully modernized, this property now offers nearly 2,500 sq ft of living area, including a permitted 858 sq ft addition (2008) with a spacious living room, dining room, two additional bedrooms, and two bathrooms. The home features 4 bedrooms, 3 full baths, a metal + gable roof, and a 2009 upgraded 2.5-ton HVAC system. A large 12×33 insulated screen room (2009) provides extra outdoor living space overlooking the peaceful acreage. The home’s layout includes a flexible

$499,900

4 beds3 baths2,502 sq ft

420 Jacks Memorial Rd, Saint Cloud, FL 34769

1.18 acres • One story home • Permitted addition

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 34744, FL:
Just one block from the beautiful St. Cloud Lakefront, this charming 2-bedroom, 1.5-bath home sits on a spacious quarter-acre corner lot, offering the perfect mix of character, comfort, and classic Florida living. Step inside to find original hardwood floors that flow through the living and bedroom areas, adding warmth and timeless appeal. The kitchen features updated cabinetry and matching appliances, blending modern convenience with inviting style. Enjoy peaceful mornings on the front porch as the sun rises over the lake, or relax in the screen-enclosed Florida room while taking in serene evening breezes. The large, fenced backyard is shaded by majestic oak trees—perfect for a hammo

$315,000

2 beds1.5 baths1,338 sq ft

200 Virginia Ave, Saint Cloud, FL 34769

Majestic oak trees • Updated cabinetry • Large shed

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

$250,000

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

Property at 1507-1509 Kentucky Ave, Saint Cloud, FL 34769, 2 beds, 2 baths

$339,900

2 beds2 baths1,596 sq ft

1507-1509 Kentucky Ave, Saint Cloud, FL 34769

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

$345,000

3 beds2 baths1,604 sq ft

608 Indiana Ave, Saint Cloud, FL 34769

Property at 812 Bryan St, Kissimmee, FL 34741, 2 beds, 2 baths

$350,000

2 beds2 baths1,070 sq ft

812 Bryan St, Kissimmee, FL 34741

Property at 433 Pennsylvania Ave, Saint Cloud, FL 34769, 2 beds, 1 bath

$170,000

2 beds1 bath940 sq ft

433 Pennsylvania Ave, Saint Cloud, FL 34769

Property at 1418 Massachussetts Ave, Saint Cloud, FL 34769, 2 beds, 2 baths

$239,000

2 beds2 baths806 sq ft

1418 Massachussetts Ave, Saint Cloud, FL 34769

Based on information submitted to the MLS GRID as of Thu Nov 27 2025. 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 5 vintage homes for sale in 34744 at a median listing price of $423K. 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 79 days and receive 4 offers. This map is refreshed with the newest listings in 34744 every 15 minutes.

In the past month, 70 homes have been sold in 34744. In addition to houses in 34744, there was also 1 condo, 60 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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