Vintage homes for sale & real estate in Maitland, FL

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ABOUT THIS HOME
Vintage Home for sale in Maitland, FL:
Welcome to this Maitland 3-bedroom, 2-bath pool home offering incredible potential on a desirable corner lot. Featuring hardwood floors, a metal roof, and a pool and spa, this property is perfect for buyers looking to renovate or investors seeking a value-add opportunity. The fully fenced yard, along with a front and back sprinkler system, provides both convenience and privacy. While the home needs some TLC, the spacious lot and solid features create a fantastic foundation for updates and personalization. Located in a sought-after area close to shopping, dining, parks, Lake Orienta Elementary school and major roadways, this property is ready to be transformed into your ideal retreat or next

$380,000

3 beds2 baths1,285 sq ft

633 Magnolia Dr, Maitland, FL 32751

Metal roof • Close to dining • Pool and spa

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Maitland, FL:
Step into timeless style with this completely updated mid-century modern home tucked away on a quiet Maitland cul-de-sac. This 3-bedroom, 2-bath residence offers 1,521 sq ft of thoughtfully designed living space featuring refinished terrazzo floors, brand-new windows, and abundant natural light. The modern kitchen shines with new cabinets, stone countertops, and stainless-steel appliances, while both bathrooms have been beautifully remodeled with contemporary finishes. Fresh interior and exterior paint, new lighting and ceiling fans throughout, and lush new landscaping make this home truly move-in ready. Enjoy the best of Central Florida living—just steps from Maitland’s shops a

$429,900

3 beds2 baths1,521 sq ft

6 Barnard Ct, Maitland, FL 32751

Stone countertops • Brand-new windows • New cabinets

ABOUT THIS HOME
Vintage Home for sale in Maitland, FL:
One or more photo(s) has been virtually staged. Experience classic Maitland charm with modern comfort in this beautifully updated 4-bed, 3-bath home just steps from Maitland City Center, Lake Sybelia, and top-rated schools. Surrounded by million-dollar homes, this property offers prime location near Winter Park, Rollins College, UCF, and leading medical centers. Enjoy nearby dining, trails, and lakes for kayaking or paddleboarding. Featuring a lighted pool, upgraded kitchen, double-pane windows, and two primary suites, this home blends style, convenience, and investment value. ? A rare Maitland gem— Roof 2024-New AC unit. schedule your private tour today!

$810,000

4 beds3 baths2,116 sq ft

245 W George Ave, Maitland, FL 32751

Updated kitchen • Lighted pool • Two primary suites

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Maitland, FL:
Welcome to your dream home located in the heart of Maitland, FL. This stunning 4-bedroom, 3-bathroom residence is a perfect blend of modern comfort and timeless elegance. Total Living Area 2760 Sq Ft. As you step inside, you'll be greeted by an inviting foyer that leads to a spacious open-concept living area, featuring high ceilings and abundant natural light. The gourmet kitchen boasts quartz countertops, new appliances, and ample cabinet space, ideal for culinary enthusiasts. The adjoining dining area is perfect for entertaining guests or enjoying family meals. The master suite is a true retreat with a walk-in closet and an en-suite bathroom featuring a luxurious soaking tub, dual vanitie

$719,900

4 beds3 baths2,676 sq ft

1511 E Horatio Ave, Maitland, FL 32751

Quartz countertops • Walk-in closet • Soaking tub

3D & VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Maitland, FL:
Canal Front Oasis on the Winter Park Chain of Lakes! Welcome to 1016 Howell Branch Road, where every day feels like a getaway. This beautifully reimagined 4-bedroom, 3-bath residence offers 3,142 square feet of inspired living space set amid lush, tropical landscaping — all within the best of Winter Park and Maitland. * The canal allows for full Lake Maitland and Winter Park Chain of Lakes access by powerboat. (Current owners have a 19' outboard they use to pull tubes, ski, wakeboard, quick trips to dog island and entertaining via scenic tours through the Winter Park Chain of Lakes. ) Originally built in 1959 and completely renovated in 2022, this two-story retreat combines rusti

$1,836,000

4 beds3 baths3,142 sq ft

1016 Howell Branch Rd, Winter Park, FL 32789

Canal front oasis • New boathouse • Outdoor living area

Property at 1655 Sunnyside Dr, Maitland, FL 32751, 3 beds, 2 baths

$725,000

3 beds2 baths1,418 sq ft

1655 Sunnyside Dr, Maitland, FL 32751

Property at 515 W Faith Ter, Maitland, FL 32751, 3 beds, 2 baths

$515,000

3 beds2 baths2,205 sq ft

515 W Faith Ter, Maitland, FL 32751

Property at 1231 Sidcup Rd, Maitland, FL 32751, 3 beds, 2 baths

$545,000

3 beds2 baths1,798 sq ft

1231 Sidcup Rd, Maitland, FL 32751

Property at 814 N Thistle Ln, Maitland, FL 32751, 4 beds, 2 baths

$699,000

4 beds2 baths2,136 sq ft

814 N Thistle Ln, Maitland, FL 32751

Property at 505 Lake Shore Dr, Maitland, FL 32751, 4 beds, 2 baths

$579,990

4 beds2 baths2,317 sq ft

505 Lake Shore Dr, Maitland, FL 32751

Property at 249 Spartan Dr, Maitland, FL 32751, 4 beds, 2 baths

$345,000

4 beds2 baths1,579 sq ft

249 Spartan Dr, Maitland, FL 32751

Property at 1518 Oranole Rd, Maitland, FL 32751, 3 beds, 1 bath

$449,900

3 beds1 bath1,848 sq ft

1518 Oranole Rd, Maitland, FL 32751

Property at 140 E Faith Ter, Maitland, FL 32751, 4 beds, 3 baths

$525,000

4 beds3 baths2,748 sq ft

140 E Faith Ter, Maitland, FL 32751

Property at 1695 E Horatio Ave, Maitland, FL 32751, 4 beds, 2.5 baths

$529,000

4 beds2.5 baths1,939 sq ft

1695 E Horatio Ave, Maitland, FL 32751

Property at 502 Oak Ln, Maitland, FL 32751, 3 beds, 3.5 baths

$658,800

3 beds3.5 baths1,966 sq ft

502 Oak Ln, Maitland, FL 32751

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NEW 7 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Maitland, FL:
Firs time buyer!! If you are looking for a place to call home this property is an absolute must see!! Free from restrictions no HOA. You can enjoy your home without any constraint. Don't miss the opportunity this is also suitable for investor. No FHA please.

$180,000

3 beds1 bath849 sq ft

5228 Andrus Ave, Orlando, FL 32810

No hoa • 9,795 sq ft lot • Built 1946

ABOUT THIS HOME
Vintage Home for sale in Maitland, FL:
NEWLY REMODELLED HOME WITH NEW A/C, UPGRADED KITCHEN, FLOORING AND ALL INTERIORS!! MUST SEE FOR MORE IMPROVEMENTS MADE, COME AND LIVE IN A BEAUTIFUL COMMUNITY IT CAN BE YOUR PRIMARY HOME OR INVESTMENT!! AGENT AND BUYER MUST VERIFY THE CORRECT ROOM DIMENSION.

$347,900

3 beds2 baths998 sq ft

5242 Andrus Ave, Orlando, FL 32810

Upgraded kitchen • New a/c • 9,208 sq ft lot

3D & VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Maitland, FL:
One or more photo(s) has been virtually staged. This beautiful two-story residence is located in the highly desired Temple Heights neighborhood in the heart of Winter Park. Situated on an expansive double lot, this well-maintained home offers over 3,900 sq ft of heated living space and features 5 bedrooms and 4 bathrooms in the main home, plus a large separate pool home/In-Law Suite complete with its own bathroom and kitchenette. The home features original hardwood and vinyl flooring throughout, high vaulted ceilings, and an open floor plan designed for both comfort and entertaining. The family room and kitchen overlook the covered lanai, oversized pool, and spacious, private backyard. Fren

$2,490,000

5 beds4 baths3,948 sq ft

1205 Mayfield Ave, Winter Park, FL 32789

In-law suite • Open floor plan • Double lot

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Maitland, FL:
This 3-bedroom 2-bath lakefront pool home with a 2-car side-entry garage on over 1/2 acre is perfectly located just a short hop from I-4, the 414, 434 and 441 combining the perfect blend of usefulness and location. Inside, the kitchen includes all appliances and sits adjacent to the dining and living areas. The main living area overlooks the inground swimming pool and Lake Eve. The 14’ X 11’ primary bedroom includes an updated ensuite bath with walk-in shower. Additional features include a huge storage area that is perfect for a home-based business or upgrading into a 4th bedroom or additional living space and an indoor laundry room with washer and dryer. Significant updates inc

$280,000

3 beds2 baths1,788 sq ft

8101 Lake Eve Dr, Orlando, FL 32810

Huge storage area • 2019 roof • Updated ensuite bath

ABOUT THIS HOME
Vintage Home for sale in Maitland, FL:
Stunning 4-bedroom, renovated pool home with new Architectural shingle roof (2023) on a generous . 40 acre lot in the highly coveted Winter Park Vias with bright open living areas, high ceilings, hardwood oak floors, two fireplaces, and a chef’s kitchen offering premium appliances including SubZero Refrigeration and Viking 6-Burner Gas Cooktop. The private backyard features a large pool, covered lanai with built-in outdoor grill w/ prep space, and lush landscaping that creates a safe green space for kids and a low-maintenance oasis for empty nesters. The main floor features a large secluded primary suite and separate full suite guest bedroom plus a gorgeous study/library with built-in

$2,345,000

4 beds3.5 baths3,986 sq ft

2299 Via Tuscany, Winter Park, FL 32789

Large pool • Premium appliances • Covered lanai

ABOUT THIS HOME
Vintage Home for sale in Maitland, FL:
Discover this spacious 4-bedroom, 2-bath single-family home perfectly situated on a large corner lot in the heart of Orlando! This property offers both comfort and versatility, featuring an expansive detached warehouse with full water and electricity, ideal for personal use, storage, or potential business operations (subject to county approval). The home boasts a functional layout with ample natural light, a large kitchen with plenty of cabinet space, and comfortable living and dining areas—perfect for family gatherings and everyday living. The generous corner lot provides privacy, additional parking, and room to expand or customize outdoor spaces. The oversized warehouse is a rare fi

$359,900

4 beds2 baths1,211 sq ft

3902 Castell Dr, Orlando, FL 32810

Ample natural light • Large corner lot • Existing utilities

Property at 259 Blossom Ln, Winter Park, FL 32789, 3 beds, 2 baths

$499,000

3 beds2 baths1,354 sq ft

259 Blossom Ln, Winter Park, FL 32789

Property at 121 Stefanik Rd, Winter Park, FL 32792, 3 beds, 2 baths

$337,500

3 beds2 baths1,392 sq ft

121 Stefanik Rd, Winter Park, FL 32792

Property at 1007 Early Ave, Winter Park, FL 32789, 3 beds, 2 baths

$425,000

3 beds2 baths1,721 sq ft

1007 Early Ave, Winter Park, FL 32789

Property at 2208 Mosher Dr, Orlando, FL 32810, 3 beds, 2 baths

$319,900

3 beds2 baths1,080 sq ft

2208 Mosher Dr, Orlando, FL 32810

Property at 1923 Linden Rd, Winter Park, FL 32792, 4 beds, 3 baths

$515,000

4 beds3 baths2,117 sq ft

1923 Linden Rd, Winter Park, FL 32792

Property at 1816 Ivy Ln, Winter Park, FL 32792, 4 beds, 2 baths

$435,500

4 beds2 baths1,725 sq ft

1816 Ivy Ln, Winter Park, FL 32792

Property at 481 Hibiscus Rd, Casselberry, FL 32707, 3 beds, 1 bath

$299,000

3 beds1 bath1,112 sq ft

481 Hibiscus Rd, Casselberry, FL 32707

Property at 612 Acapulca Way, Altamonte Springs, FL 32714, 3 beds, 2 baths

$280,000

3 beds2 baths1,069 sq ft

612 Acapulca Way, Altamonte Springs, FL 32714

Property at 2211 Beatrice Dr, Orlando, FL 32810, 4 beds, 2 baths

$390,000

4 beds2 baths1,594 sq ft

2211 Beatrice Dr, Orlando, FL 32810

Property at 216 Obrien Rd, Fern Park, FL 32730, 4 beds, 2 baths

$335,000

4 beds2 baths1,432 sq ft

216 Obrien Rd, Fern Park, FL 32730

Property at 1920 Carrigan Ave, Winter Park, FL 32792, 3 beds, 2 baths

$315,000

3 beds2 baths1,242 sq ft

1920 Carrigan Ave, Winter Park, FL 32792

Property at 825 Palmer Ave, Winter Park, FL 32789, 3 beds, 3 baths

$1,799,000

3 beds3 baths3,297 sq ft

825 Palmer Ave, Winter Park, FL 32789

Property at 3809 Needles Dr, Orlando, FL 32810, 3 beds, 3 baths

$375,000

3 beds3 baths1,653 sq ft

3809 Needles Dr, Orlando, FL 32810

Property at 7818 Plantation Dr, Orlando, FL 32810, 4 beds, 3 baths

$499,000

4 beds3 baths1,675 sq ft

7818 Plantation Dr, Orlando, FL 32810

Based on information submitted to the MLS GRID as of Sat Nov 29 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 Maitland

There are currently 15 vintage homes for sale in Maitland at a median listing price of $437K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Maitland stay on the market for 64 days and receive 3 offers. Popular neighborhoods include Spring Valley, Kingswood Manor, and Downtown Maitland. This map is refreshed with the newest listings in Maitland every 15 minutes.

In the past month, 26 homes have been sold in Maitland. In addition to houses in Maitland, there were also 44 condos, 9 townhouses, and 1 multi-family unit for sale in Maitland last month. Find your dream home in Maitland 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 Maitland are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Maitland. Our Maitland real estate stats and trends will give you more information about home buying and selling trends in Maitland. If you're looking to sell your home in the Maitland area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Maitland with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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