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Casselberry, FL Homes for Sale under $400,000

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  • /20

    $329,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    371 Pinesong Dr, Casselberry, FL 32707

    Welcome to this charming, move-in ready townhome in the highly desirable Pine Tree Village community of Deer Run. Filled with natural light, this bright and inviting home offers a warm, open living space perfect for both everyday living and entertaining. This townhome has no shared walls and lives like a single family home. The kitchen and bathrooms have been beautifully updated with granite

    Agent Photo

    Brett Winters

    OLDE TOWN BROKERS INC

    (321) 386-1788

    371 Pinesong Dr, Casselberry, FL 32707
  • /17

    $334,900

    • 2 Beds
    • 2 Baths
    • 1,411 Sq Ft

    3635 S Saint Lucie Dr, Casselberry, FL 32707

    LOCATION is everything. Enjoy a freshly painted, newly carpeted, 2 bedroom, 2 bath, charming home close to all amenities. Enjoy the privacy of the large sized fully fenced backyard, perfect for pets and has the potential for a future pool/spa. Feel carefree with low maintenance, vaulted ceilings and enjoy everyday living with a large family room and fireplace. The family room opens to the kitchen

    Agent Photo

    Barron Becker

    PROPERTY MANAGEMENT USA LLC

    (321) 252-6326

    3635 S Saint Lucie Dr, Casselberry, FL 32707
  • /29

    $385,999

    • 4 Beds
    • 2.5 Baths
    • 1,982 Sq Ft

    155 Fallwood St, Casselberry, FL 32730

    Welcome home to this beautifully maintained townhome tucked away in a charming, quiet community with a warm, family-friendly atmosphere. Thoughtfully updated, this home features a brand-new roof, exterior repaint, hot water heater, A/C unit improvements, and multiple upgrades completed within the past two years, offering added value and peace of mind. Also, HOA is in the process of upgrading the

    Brian McKinney ALL FLORIDA REALTY GROUP

    155 Fallwood St, Casselberry, FL 32730
  • /37

    $385,000

    • 4 Beds
    • 3.5 Baths
    • 2,210 Sq Ft

    1828 Grand Rue Dr, Casselberry, FL 32707

    BEAUTIFUL and SPACIOUS townhouse with over 2100-sqft. No worries about any exterior headache - as the roof is even covered by the HOA! Freshly repainted and balcony updates being done as well! Upon entry to the first floor, you will find new tile, and the first floor ensuite bedroom, perfect for guests or as a 2nd master bedroom! Heading up the stairs, you will find a spacious floor plan, with

    Husain Jaffer CHARLES RUTENBERG REALTY ORLANDO

    1828 Grand Rue Dr, Casselberry, FL 32707
  • /23

    $310,000

    • 3 Beds
    • 2.5 Baths
    • 1,333 Sq Ft

    1934 Fenwick Way, Casselberry, FL 32707

    Step into this immaculate 2-story townhome, perfectly maintained and in the best possible condition. Located in a desirable, friendly neighborhood, this home offers both comfort and convenience. With spacious living areas, modern finishes, and a well-thought-out layout, it’s move-in ready for its next owner. Enjoy the peace of mind that comes with a property that has been cared for to

    Ismenia Cam GOLDEN KEY HOMES REALTY INC

    1934 Fenwick Way, Casselberry, FL 32707
  • /28

    $345,900

    • 2 Beds
    • 1.5 Baths
    • 924 Sq Ft

    82 Concord Dr, Casselberry, FL 32707

    Welcome to 82 Concord Drive in Castleberry, Florida—a rare opportunity offering charm, space, and exceptional investment potential. Situated on a generous 0.36-acre fully fenced lot, this 2-bedroom, 1.5-bath home provides both privacy and flexibility in a highly desirable location. Inside, the home features a cozy and inviting layout, perfect for comfortable living or a potential office space.

    Michael Hayman KELLER WILLIAMS WINTER PARK

    82 Concord Dr, Casselberry, FL 32707
  • /33

    $320,000 Open Sun 12PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,719 Sq Ft

    2401 Antilles Dr, Winter Park, FL 32792

    Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. The home has newer A/C, high impact windows and the home has been re-piped for your peace of mind. This is a

    George Freelove KELLER WILLIAMS REALTY AT THE PARKS

    2401 Antilles Dr, Winter Park, FL 32792
  • /39

    $339,900

    • 4 Beds
    • 2 Baths
    • 1,556 Sq Ft

    526 E Foothill Way, Casselberry, FL 32707

    Situated on a peaceful, tree-lined street with mature landscaping and a generously sized backyard, this four-bedroom, two-bathroom home offers space and versatility, including two additional bonus or flex rooms that can easily adapt to your lifestyle needs. The home features a functional floor plan with great bones and an abundance of natural light that flows throughout, creating a warm and

    David Berlant KELLER WILLIAMS REALTY AT THE PARKS

    526 E Foothill Way, Casselberry, FL 32707
  • /25

    $340,000

    • 3 Beds
    • 2 Baths
    • 1,257 Sq Ft

    2300 Lake Rd, Casselberry, FL 32730

    Welcome to 2300 Lake Rd in Fern Park—a charming 3-bedroom, 2-bath pool home built with solid block construction, perfectly positioned on a corner lot with a fully fenced backyard, offering both privacy and long-term durability. This home doesn’t just offer character—it offers peace of mind with major updates already done, including a roof and HVAC just 5 years old and updated windows, helping

    Michelle Forbes MARK SPAIN REAL ESTATE

    2300 Lake Rd, Casselberry, FL 32730
  • /32

    $349,950

    • 2 Beds
    • 2 Baths
    • 1,398 Sq Ft

    4192 Buglers Rest Place, Casselberry, FL 32707

    Welcome home to 4192 Buglers Rest Place an adorable 2-bedroom 2-bathroom split plan home nestled in the desirable community of Deer Run. The open floor plan is light and bright perfect for entertaining with an updated kitchen boasting granite counter tops, a decorative back splash, and stainless-steel appliances. It adjoins the great room and wonderful eat in dining area that opens onto the

    Lisa Edwards KELLER WILLIAMS ADVANTAGE REALTY

    4192 Buglers Rest Place, Casselberry, FL 32707
  • /37

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,397 Sq Ft

    3374 Hamlet Loop, Winter Park, FL 32792

    This well-maintained 3 bedroom, 2.5 bath home is located in the quaint, charming city of Winter Park. Step inside to a split-bedroom floor plan featuring a spacious living and dining area with high ceilings and beautiful natural lighting. The kitchen is equipped with ample cabinetry in excellent condition, spacious countertops with breakfast bar seating, and a large pantry. The primary bedroom

    Thomas Weclew THE REALTY MEDICS

    3374 Hamlet Loop, Winter Park, FL 32792
  • /27

    $400,000

    • 4 Beds
    • 2 Baths
    • 1,966 Sq Ft

    254 Oak Park Place, Casselberry, FL 32707

    Located in the desirable South Division of Sunset Oaks, Seminole County, this charming single-family home offers 4 spacious bedrooms and 3 modern bathrooms. The property features a lovely backyard, perfect for outdoor gatherings or quiet relaxation. Nestled in a family-friendly neighborhood, this home provides both comfort and convenience, making it an ideal choice for your next chapter.

    Richard Roberts ROBERTS & ROBERTS REALTY INC

    254 Oak Park Place, Casselberry, FL 32707
  • /39

    $355,000

    • 2 Beds
    • 2.5 Baths
    • 1,550 Sq Ft

    2648 Galliano Cir, Winter Park, FL 32792

    Welcome to Winter Park two-story townhome located in the private, gated community of Vistas at Lake Howell. This 2 bedroom, 2.5 bathroom home offers approximately 1,550 sq ft of living space. The kitchen features stainless steel appliances, including dishwasher, range, refrigerator, and microwave. The living and dining room combination provides an open and functional layout. All bedrooms are

    Elizabeth Santiago ALLEGIANT MANAGEMENT GROUP INC

    2648 Galliano Cir, Winter Park, FL 32792
  • /25

    $344,900

    • 3 Beds
    • 2 Baths
    • 1,287 Sq Ft

    800 Diane Cir, Casselberry, FL 32707

    Welcome to 800 Diane Dr. — a beautifully updated corner-lot home perfect for families and first-time buyers. This warm and inviting property features a brand-new kitchen with modern finishes, new flooring throughout, and updated windows that fill the home with natural light. Three majestic live oak trees frame the property, adding timeless beauty, shade, and curb appeal. The open layout provides

    Michael Mullvain WESTIN REALTY GROUP

    800 Diane Cir, Casselberry, FL 32707
  • /21

    $330,000

    • 3 Beds
    • 3 Baths
    • 1,793 Sq Ft

    442 Meadowood Blvd, Casselberry, FL 32730

    Welcome to this beautifully renovated townhome, privately tucked away at the back of the highly desirable Lake of the Woods community. Offering 1,793 square feet of well-designed living space, this 3-bedroom, 3-bath townhome includes a first-floor bonus room ideal for a home office or workout space. Upstairs, two spacious bedrooms each feature en-suite bathrooms and walk-in closets, creating dual

    Vinny Lay COMPASS FLORIDA LLC

    442 Meadowood Blvd, Casselberry, FL 32730
  • /47

    $360,000

    • 3 Beds
    • 2.5 Baths
    • 1,682 Sq Ft

    1552 Florentino Ln, Winter Park, FL 32792

    BACK ON THE MARKET, BUYERS FINANCING FELL THROUGH! Welcome to this beautifully upgraded corner townhome located in the desirable gated community of VISTAS AT LAKE HOWELL in Winter Park, Seminole County. This spacious residence offers 1,682 sq ft under air (2,861 sq ft total), built in 2004, with 3 bedrooms and 2.5 baths, and is perfectly positioned on a corner lot for added privacy and natural

    Nohora Gomez COLDWELL BANKER REALTY

    1552 Florentino Ln, Winter Park, FL 32792
  • /50

    $349,990

    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    230 S Embrey, Casselberry, FL 32707

    Discover the perfect balance of peace and convenience in this well-kept 3 bedrooms, 2 full baths, renovated kitchen adjacent to open living room (facing east) and an unfinished additional room. That room has access to the street and screened porch. Outside the screened porch is a brick paved patio, an unfinished garage/shed, a deck facing east to west and a backyard all fenced in. Only recent

    Shannon Cruz Acosta CITARELLI REALTY GROUP LLC

    230 S Embrey, Casselberry, FL 32707
  • /38

    $330,000 Open Sat 2PM - 4PM

    • 3 Beds
    • 2.5 Baths
    • 2,012 Sq Ft

    1517 N Carolwood Blvd, Casselberry, FL 32730

    UPDATED AND BACK ON THE MARKET!! Welcome to your new home in the highly sought-after Lake of the Woods community! This beautifully updated 3-bedroom, 2.5-bath townhome spans over 2,000 sq/ft of open-concept living, offering the perfect blend of style, comfort, and space. Recently updated, the second floor boasts brand-new flooring and fresh paint, giving the space a modern, polished look. A

    Bob Broughton BROUGHTON REALTY GROUP

    1517 N Carolwood Blvd, Casselberry, FL 32730
  • /38

    $389,900

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft

    70 S Winter Park Dr, Casselberry, FL 32707

    Discover this beautifully updated home in the heart of Casselberry, FL. This 3-bedroom, 2-bath residence features spacious open-concept living areas designed for both comfort and entertaining. The modern kitchen showcases quartz countertops, updated appliances, and an oversized island, flowing effortlessly into the main living space and anchored by a charming wood-burning fireplace that creates a

    Steven Koleno BEYCOME OF FLORIDA LLC

    70 S Winter Park Dr, Casselberry, FL 32707
  • /33

    $369,500

    • 3 Beds
    • 2 Baths
    • 1,694 Sq Ft

    523 Sundown Trail, Casselberry, FL 32707

    One or more photo(s) has been virtually staged. Great Opportunity, Just reduced in price. Looking for a quiet, peaceful neighborhood with plenty of space to relax, this may be your next home! Located in Casselberry, this Wil O’ Wik home offers a large 80X125 lot with room for a pool in the rear yard. No Rear Neighbors, this home backs up to Gee Creek and a wooded tree line for extra privacy! The

    Chris Brown RE/MAX TOWN & COUNTRY REALTY

    523 Sundown Trail, Casselberry, FL 32707
  • /19

    $311,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    250 Raintree Dr Unit 24, Casselberry, FL 32707

    Fantastic move in ready Townhouse. Very spacious living areas. Large Master Bedroom with walk in closet. Tile throughout the living areas . Clean maintained carpet in the bedrooms. Covered patio porch. Located in a Deer Run right off Red Bug and right down the road from Red Bug Lake Park. Fantastic family neighborhood and school zones.

    TJ Tuzzeo KONA REALTY SERVICES LLC

    250 Raintree Dr Unit 24, Casselberry, FL 32707
  • /54

    $397,000

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft

    2532 Dakota Trail, Casselberry, FL 32730

    Welcome to the one you’ve been waiting for in desirable Fern Park, Florida. This beautifully maintained 3 bedroom, 2 bathroom one story home with a 2 car garage offers 1,670 heated square feet of thoughtfully designed living space and has been tastefully remodeled over the years. With a new roof installed in 2019 and a solar panel system that will be fully paid off at closing by the seller, this

    Ronald Ziolkowski RE/MAX PRIME PROPERTIES

    2532 Dakota Trail, Casselberry, FL 32730
  • /29

    $315,000

    • 3 Beds
    • 3.5 Baths
    • 1,652 Sq Ft

    1515 Winter Green Blvd, Winter Park, FL 32792

    Offering the comfort and feel of a single-family home with the convenience of townhome living, this beautifully maintained two-story residence features 3 bedrooms, 2.5 baths, and a private courtyard conveniently located in Winter Park. Sliding glass doors throughout the home fill the interior with natural light and create a seamless connection to your private outdoor courtyard. Inside, the

    Jill Healey KELLER WILLIAMS WINTER PARK

    1515 Winter Green Blvd, Winter Park, FL 32792
  • /15

    $319,900

    • 3 Beds
    • 3 Baths
    • 1,803 Sq Ft

    2487 Harbour Way, Winter Park, FL 32792

    Unmissable opportunity in Winter Park! Beautiful house for sale with 3 bedrooms and 3 bathrooms, perfect for those seeking comfort, convenience and quality of life. Located in one of the most sought-after areas of Winter Park, with an excellent location, close to schools, shops, restaurants, parks and much more! The community offers a complete infrastructure with a swimming pool, playground,

    Marcus Freire de Araujo WRA BUSINESS & REAL ESTATE

    2487 Harbour Way, Winter Park, FL 32792
  • /22

    $358,500

    • 3 Beds
    • 2.5 Baths
    • 1,609 Sq Ft

    984 Legacy Winds Way, Casselberry, FL 32707

    Short Sale. GREAT OPPORTUNITY! Located in desirable Legacy Winds, this townhome offers the perfect blend of modern design, comfort, and convenience. Featuring 3 bedrooms and 2.5 baths, this TH welcomes you with an open and airy floor plan designed for everyday living and easy entertaining. The open kitchen is the heart of the home, complete with stainless steel appliances, a spacious center

    Doug Woehr COLDWELL BANKER REALTY

    984 Legacy Winds Way, Casselberry, FL 32707
  • /40

    $362,000

    • 4 Beds
    • 2 Baths
    • 1,641 Sq Ft

    1231 Avalon Blvd, Casselberry, FL 32707

    One or more photo(s) has been virtually staged. **Improved Pricing...Step into the welcoming, well-established community of Casselberry, where this delightful single-family residence is poised for its next chapter. Located in one of Seminole County's most desirable suburbs, this 4 bedroom/2 bath home offers a blend of tranquil suburban living and exceptional Central Florida convenience. This

    Giovanna D'Alessandro RP INVESTMENT REALTY LLC

    1231 Avalon Blvd, Casselberry, FL 32707
  • /60

    $380,000

    • 4 Beds
    • 3 Baths
    • 2,083 Sq Ft

    1375 Lake Dr, Casselberry, FL 32707

    Welcome to 1375 Lake Drive in Casselberry, a beautifully fully remodeled 4-bedroom, 3-bathroom, plus a office home that is truly move-in ready from top to bottom. Thoughtfully updated with modern finishes and a functional layout, this home offers the perfect opportunity for first-time buyers or anyone looking for a stylish, turnkey property. Perfect for a growing family with a specific budget in

    Abby Greenberg COMPASS FLORIDA LLC

    1375 Lake Dr, Casselberry, FL 32707
  • /61

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,853 Sq Ft

    244 Overbrook Dr, Casselberry, FL 32707

    Luxury Custom Home on Over Half an Acre – Golf Course Frontage Living at Its Finest. Experience elegance, privacy, and breathtaking views in this stunning custom-built home perfectly positioned on over 1⁄2 acre of prime golf course frontage.Wake up each morning to sweeping fairway views and enjoy peaceful evenings under the stars from your expansive backyard oasis. Designed with both luxury

    Nathaniel Zinno ASSURED PROPERTY MANAGEMENT

    244 Overbrook Dr, Casselberry, FL 32707
  • /24

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,914 Sq Ft

    420 Harbor Winds Ct, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. This stunning 3-bedroom, 2.5-bathroom townhouse offers the perfect blend of modern luxury and serene living, complete with a two-car garage and an unbeatable location. Step inside to a home that feels brand new, featuring a freshly repainted interior and an open, airy layout designed for both comfort and style. The heart of the home is a

    Robert Arnold SAND DOLLAR REALTY GROUP INC

    420 Harbor Winds Ct, Winter Springs, FL 32708
  • /41

    $360,900

    • 3 Beds
    • 2.5 Baths
    • 1,914 Sq Ft

    451 Harbor Winds Ct, Winter Springs, FL 32708

    Well maintained! Move-in Ready! Fabulous 2-story, 3 bedroom, 2 full bath and a half bath townhouse with attached 2-car garage in the exclusive gated community of Harbor Winds. Upgrades include: New Roof (2023); New Gutters (2023); New A/C System (2023); New Water Heater (2023); New Stainless Steel Appliances (2023) to include Refrigerator, Range, Dish Washer and Microwave. Inside, the perfectly

    Anderson (Luis) Zamora OLYMPUS EXECUTIVE REALTY INC

    451 Harbor Winds Ct, Winter Springs, FL 32708
  • /26

    $389,000

    • 4 Beds
    • 2 Baths
    • 1,571 Sq Ft

    2632 Talbot Rd, Fern Park, FL 32730

    Enjoy Florida’s natural beauty in this updated classic Florida home, perfectly situated on a quiet residential block yet close to abundant shopping, dining, and community amenities. This spacious four-bedroom property offers generous common areas ideal for entertaining, along with a beautifully refreshed interior featuring new cabinets and quartz countertops in both the kitchen and bathrooms. The

    Ryan Langley FLORIDA REALTY INVESTMENTS

    2632 Talbot Rd, Fern Park, FL 32730
  • /21

    $335,000

    • 2 Beds
    • 2 Baths
    • 1,177 Sq Ft

    2344 Sierra Ln, Maitland, FL 32751

    Price improved! CONDO WITH PRIVATE GARAGE - JUST REPLUMBED WITH WARRANTY! Discover the perfect blend of comfort, elegance, and convenience in this beautifully updated 2-bedroom, 2-bath condominium in the highly sought-after Sierra Condominiums of Maitland. This move-in ready condo welcomes you with a screened front porch and an inviting living room with a wood-burning fireplace with an electric

    Kathy McDonald WATSON REALTY CORP

    2344 Sierra Ln, Maitland, FL 32751
  • /21

    $302,900

    • 2 Beds
    • 1.5 Baths
    • 1,148 Sq Ft

    605 Plum Ln, Altamonte Springs, FL 32701

    Price Reduction !!!....This comfortable 3 bedroom, 1.5 bathroom, single-family home is in move-in ready condition with a lot of potential and is in a quiet, serene area! It has cozy living dining room areas open to each other with nice access to the kitchen, leading to a covered screen patio. It boasts a huge backyard just waiting for planting fruit trees and flowers! It is within close proximity

    Michael Harrison ISLAND REALTORS, INC.

    605 Plum Ln, Altamonte Springs, FL 32701
  • /28

    $335,000

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    471 Harbor Winds Ct, Winter Springs, FL 32708

    Experience the perfect blend of location and low-maintenance living at 471 Harbor Winds Court. Located in a secure, gated Winter Springs community, this move-in ready home offers ultimate peace of mind with a NEW ROOF (2024). The functional interior features a rare and highly desired Large Primary Suite on the Main Floor, complete with dual closets for abundant storage. The open, inviting layout

    Terrica Francois KELLER WILLIAMS ADVANTAGE III

    471 Harbor Winds Ct, Winter Springs, FL 32708

Home Trends in Casselberry, FL

Housing Trends

Median Sale Price
$353,500
Median Single Family Sale Price
$375,000
Median Townhouse Sale Price
$282,500
Median 2 Bedroom Sale Price
$179,950
Median 1 Bedroom Sale Price
$143,000
Average Price Per Sq Ft
$222
Number of Homes for Sale
76
Last 12 months Home Sales
464
Months of Supply
2.00
Median List Price
$369,900
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-1%
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