Vintage homes for sale & real estate in Casselberry, FL

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LISTED BY REDFIN3D & VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Casselberry, FL:
Step into a truly unique property in Casselberry, FL, a 9-bedroom, 5-bathroom home with 3,460 square feet of flexible living space designed to suit almost any vision. Whether you’re looking to create a standout single-family residence, a multi-family rental, assisted living facility or an innovative investment opportunity, this home delivers unmatched potential. The layout is exceptional, featuring multiple shared spaces such as a chef-ready kitchen with stainless steel appliances, center island, and a large 15 foot pantry, a dining area, and a dedicated workout space. Each room offers privacy while contributing to the home’s communal flow, making it perfect for residents, guest

$649,000

9 beds5 baths3,460 sq ft

395 Piney Ridge Rd, Casselberry, FL 32707

Covered patio • Large pantry • Chef ready kitchen

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Casselberry, FL:
One or more photo(s) has been virtually staged. Seller may consider seller contribution! Come see this beautiful renovated home offering the perfect blend of comfort and style. Nestled in a neighborhood with no HOA! This 4 bedroom and 2 bathroom move-in ready home boasts a bright and open floor plan with spacious living areas, an updated kitchen featuring modern finishes, and a private backyard perfect for entertaining or relaxing after a long day. This home was completely painted inside and out. It has a 2025 ROOF, 2023 AC and 2021 electrical panels. The big ticket items have been taken cared of. Conveniently located near shopping, dining, and major highways. It is home business friendly c

$335,000

4 beds2 baths1,432 sq ft

216 Obrien Rd, Fern Park, FL 32730

Renovated home • Private backyard • Updated kitchen

ABOUT THIS HOME
Vintage Home for sale in Casselberry, FL:
RARE PURCHASE/RENT-TO-OWN OPPORTUNITY WITH SPECIAL OFFICE/RESIDENTIAL ZONING! (Grandfathered-In) Imagine having the convenience of living and working in the same location. This move-in ready completely renovated LAKEFRONT POOL property has so much flexibility. Special grandfathered-in zoning provides endless opportunities, featuring 3 rooms and 2 full bathrooms that could actually be split into 2 separate rentable spaces. This allows you to reside on half of the property and lock-off the other half (with separate entrance) to be utilized for business purposes, such as a LAW/ CPA OFFICE, or the newly added Medical use. With so much to love, this property won't last long so book your tour

$375,000

3 beds2 baths1,644 sq ft

1260 Seminola Blvd, Casselberry, FL 32707

Separate entrance • Lakefront pool • 0.32 acre lot

ABOUT THIS HOME
Vintage Home for sale in Casselberry, FL:
A true garden home in Casselberry Garden District for you to unpack your green thumb and grow your equity. This move-in ready home is an excellent first home or rental investment property, serving 3 Bedrooms, 1 bathroom, an inside utility room for laundry and storage, and one covered carport space. This corner lot features foliage and mature landscaping, raised beds for you to claim already producing herbs, melons, peppers and fruiting citrus trees. The home was renovated in 2018 including the bathroom and kitchen, flooring, appliances, and Roof. HVAC is 2022, and a brand new (2025) electrical panel was just installed for buyers peace of mind. Location is privy to Seminole county schools, n

$299,000

3 beds1 bath1,112 sq ft

481 Hibiscus Rd, Casselberry, FL 32707

Raised beds • Inside utility room • Mature landscaping

ABOUT THIS HOME
Vintage Home for sale in Casselberry, FL:
* * * * * Seller motivated - all offers considered * * * * * * * * * * A must see before buying anything ELSE * * * * * * 4BR/2BA 1600 sq ft Charming home and Separate In-Law Suite 1BR/1BA 400 sq ft. . This is in addition to the square footage listed on the property appraiser modern updates with new roof near downtown Orlando and close to everything. Nestled in a prime location just minutes from downtown Orlando and renowned theme parks. Not to mention close to shopping, dining and entertainment with residential feel. This home features a variety of living capabilities, main house has 4 bedrooms, bonus room with office area with two full baths. Plus a separate in-law

$479,990

4 beds3 baths1,606 sq ft

110 E Lauren Ct, Fern Park, FL 32730

In-law suite • Full kitchen • Boat access

Property at 101 E Lauren Ct, Fern Park, FL 32730, 4 beds, 2 baths

$420,000

4 beds2 baths2,040 sq ft

101 E Lauren Ct, Fern Park, FL 32730

Property at 417 Rain Lily Cv, Casselberry, FL 32707

$1,450,000

— beds— baths— sq ft

417 Rain Lily Cv, Casselberry, FL 32707

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ABOUT THIS HOME
Vintage Home for sale in Casselberry, FL:
Discover your new downtown Winter Park ground-floor pied-à-terre. Two blocks from Park Avenue, the 1960s mid-century modern Whispering Waters Condominiums are a Winter Park landmark. Your remodeled end-unit studio features an updated open kitchen with plentiful wood cabinets, ceramic tile flooring throughout, new dual-pane windows, a stylish updated bathroom with a step-in shower, and wood built-ins in the living room. Open to the living room is a sleeping alcove that accommodates a queen-size bed. An additional 9’ by 6’ enclosed room could be used as a bedroom, an office, or a lounging space. With easy access from your new pad to both Interlachen Avenue and Morse Bouleva

$329,000

1 bed1 bath570 sq ft

311 E Morse Blvd Unit 6-3, Winter Park, FL 32789

Updated open kitchen • Remodeled end unit • Updated bathroom

3D & VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Casselberry, 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

ABOUT THIS HOME
Vintage Home for sale in Casselberry, FL:
The house is located in great location and features 3 bedrooms, 2 bathrooms. It sits on a corner lot and offers high ceilings throughout.

$440,000

3 beds2 baths1,355 sq ft

1909 Edwin Blvd, Winter Park, FL 32792

High ceilings • Corner lot • 0.23 acre lot

ABOUT THIS HOME
Vintage Home for sale in Casselberry, 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 Casselberry, 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

ABOUT THIS HOME
Vintage Home for sale in Casselberry, FL:
Newly updated 2 Bedrooms and 1 Bathroom conveniently located in Winter Park/Orlando next to all of shops and restaurants. With private lake access to launch and dock your watercraft within the community for boating and fishing. Walk to Trader Joes next door and Winter Park Village to enjoy great number of restaurants, movie theater, retail shops and grocery stores.

$235,000

2 beds1 bath768 sq ft

151 N Orlando Ave #226, Winter Park, FL 32789

Corner unit • Private lake access • $483 HOA

Property at 245 W George Ave, Maitland, FL 32751, 4 beds, 3 baths

$810,000

4 beds3 baths2,116 sq ft

245 W George Ave, Maitland, FL 32751

Property at 742 E Church Ave #744, Longwood, FL 32750, 4 beds, 2 baths

$475,000

4 beds2 baths1,275 sq ft

742 E Church Ave #744, Longwood, FL 32750

Property at 2299 Via Tuscany, Winter Park, FL 32789, 4 beds, 3.5 baths

$2,345,000

4 beds3.5 baths3,986 sq ft

2299 Via Tuscany, Winter Park, FL 32789

Property at 516 Henkel Cir, Winter Park, FL 32789, 5 beds, 6 baths

$3,599,000

5 beds6 baths4,143 sq ft

516 Henkel Cir, Winter Park, FL 32789

Property at 150 N Edgemon Ave, Winter Springs, FL 32708, 3 beds, 1 bath

$315,000

3 beds1 bath1,008 sq ft

150 N Edgemon Ave, Winter Springs, FL 32708

Property at 31 S Edgemon Ave, Winter Springs, FL 32708, 4 beds, 3 baths

$348,000

4 beds3 baths1,270 sq ft

31 S Edgemon Ave, Winter Springs, FL 32708

Property at 1822 Greenwich Ave, Winter Park, FL 32789, 3 beds, 2 baths

$1,199,900

3 beds2 baths1,627 sq ft

1822 Greenwich Ave, Winter Park, FL 32789

Property at 1246 S Oleander St, Longwood, FL 32750, 3 beds, 2 baths

$339,900

3 beds2 baths1,160 sq ft

1246 S Oleander St, Longwood, FL 32750

Property at 272 W Warren Ave, Longwood, FL 32750, 4 beds, 1 bath

$410,000

4 beds1 bath1,386 sq ft

272 W Warren Ave, Longwood, FL 32750

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 1016 Howell Branch Rd, Winter Park, FL 32789, 4 beds, 3 baths

$1,836,000

4 beds3 baths3,142 sq ft

1016 Howell Branch Rd, Winter Park, FL 32789

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 457 E New England Ave, Winter Park, FL 32789, 5 beds, 4.5 baths

$3,100,000

5 beds4.5 baths3,847 sq ft

457 E New England Ave, Winter Park, FL 32789

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

Based on information submitted to the MLS GRID as of Sun Nov 30 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 Casselberry

There are currently 7 vintage homes for sale in Casselberry at a median listing price of $322K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Casselberry stay on the market for 76 days and receive 1 offers. Popular neighborhoods include Indian Hills, Lake of the Woods Townhouse, Deer Run, Seminole Heights, and North Orlando. This map is refreshed with the newest listings in Casselberry every 15 minutes.

In the past month, 29 homes have been sold in Casselberry. In addition to houses in Casselberry, there were also 29 condos, 17 townhouses, and 1 multi-family unit for sale in Casselberry last month. Casselberry is a minimally walkable city in Florida with a Walk Score of 33. Casselberry is home to approximately 26,171 people and 8,537 jobs. Find your dream home in Casselberry 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 Casselberry are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Casselberry. Our Casselberry real estate stats and trends will give you more information about home buying and selling trends in Casselberry. If you're looking to sell your home in the Casselberry area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Casselberry with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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