24

Winter Springs, FL Homes for Sale under $300,000

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  • /50

    $234,990

    • 2 Beds
    • 2.5 Baths
    • 1,156 Sq Ft

    611 Casa Park A Ct, Winter Springs, FL 32708

    Welcome to this beautifully updated 2 Bed, 2.5 Bath townhome nestled in the desirable Casa Park Villas community in Winter Springs! Step inside & the open-concept design features a bright and airy living room that seamlessly flows into the dining area and kitchen, creating an inviting space for relaxation and entertaining. The kitchen boasts all SS appliances, including a side-by-side

    Agent Photo

    Jay Patterson

    KELLER WILLIAMS ADVANTAGE REALTY

    (321) 413-8639

    611 Casa Park A Ct, Winter Springs, FL 32708
  • /25

    $254,999

    • 2 Beds
    • 2.5 Baths
    • 1,156 Sq Ft

    602 Casa Park Court F, Winter Springs, FL 32708

    Welcome to Casa Park Villas, where comfort meets convenience right next to Trotwood Park in the heart of Winter Springs. This bright, updated 2-story townhome has been beautifully remodeled with over $30,000 in upgrades and offers relaxing views of the community pool and pond. Custom window treatments with 2 motorized roller shades in the living room & patio slider, plus upgraded rollers in the

    Shari Starner CHARLES RUTENBERG REALTY ORLANDO

    602 Casa Park Court F, Winter Springs, FL 32708
  • /18

    $275,000

    • 3 Beds
    • 2.5 Baths
    • 1,492 Sq Ft

    4126 Hedge Maple Place, Winter Springs, FL 32708

    Don’t Miss This Incredible Opportunity to ASSUME A 2.5% FHA LOAN! Beautiful Townhouse is located in Heritage Commons. This gated community offers a pool, a playground for the little ones to play, a fenced in doggie space for your furry friends and in fabulous school districts. This 3 bedroom, 2.5 bath townhouse has a great open floorplan with kitchen that includes a breakfast bar and is open to

    Jennifer Draper LPT REALTY LLC (DB)

    4126 Hedge Maple Place, Winter Springs, FL 32708
  • /27

    $270,000

    • 2 Beds
    • 1.5 Baths
    • 1,108 Sq Ft

    4522 Brook Hollow Cir, Winter Springs, FL 32708

    **Seller will credit the buyer $5,000 towards the special assessment or closing costs!** Welcome to this charming, move-in ready 2-bedroom, 1.5-bathroom townhome designed for both comfort and convenience. Inside, the main floor boasts inviting common areas, including a spacious kitchen with newly installed recessed lighting and a cozy eat-in nook. A guest half bathroom on the main level adds

    Jaclynn Nielsen THE AGENCY ORLANDO

    4522 Brook Hollow Cir, Winter Springs, FL 32708
  • /6

    $246,000

    • 2 Beds
    • 1.5 Baths
    • 896 Sq Ft

    122 Kristi Ann Ct, Winter Springs, FL 32708

    Stunning fully remodeled townhome featuring top-quality finishes and modern design throughout! Enjoy a bright open floor plan with wide-plank flooring, a chef’s kitchen with quartz countertops, custom cabinetry, and premium stainless appliances. All bathrooms have been beautifully updated with designer fixtures and tile. Recent upgrades include new HVAC, windows, and more. Conveniently located

    Vered Thacker DALTON WADE INC

    122 Kristi Ann Ct, Winter Springs, FL 32708
  • /54

    $235,000

    • 2 Beds
    • 2.5 Baths
    • 1,156 Sq Ft

    608 Casa Park Ct N Unit F, Winter Springs, FL 32708

    Welcome to 608 Casa Park Ct, a charming and well-maintained townhome in the highly sought-after Casa Park Villas community of Winter Springs. This residence offers a functional 2-bedroom, 2.5-bathroom layout designed for comfort and convenience.The main floor features a spacious living and dining area filled with natural light, a well-appointed kitchen with ample cabinetry, and a half bath

    Florentino Beltran KELLER WILLIAMS ADVANTAGE 2 REALTY

    608 Casa Park Ct N Unit F, Winter Springs, FL 32708
  • /25

    $245,000

    • 3 Beds
    • 1.5 Baths
    • 1,130 Sq Ft

    411 Green Spring Cir, Winter Springs, FL 32708

    Opportunity knocks in the Vineyards of Mount Greenwood! This 3-bedroom, 1.5-bath townhome in Winter Springs is full of potential and ready for a buyer with vision. The main floor features a spacious living and dining area, kitchen, convenient half bath, and extra storage under the stairs. Sliding glass doors lead to a covered and screened rear porch with an additional storage closet—ideal for

    Sarita Cabrera WATSON REALTY CORP

    411 Green Spring Cir, Winter Springs, FL 32708
  • /31

    $235,000 Open Sun 12PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 1,400 Sq Ft

    30 Moree Loop Unit 39, Winter Springs, FL 32708

    Fall in love with this 3 bed, 2.5 bath townhome-style condo in one of Winter Springs’ most sought-after communities! Featuring a remodeled kitchen, luxury vinyl plank floors, updated baths with new vanities, new tile shower, and fresh paint, this home is stylish and low-maintenance. Roof replaced in 2021, new fencing, and newer water heater mean peace of mind for years to come!Inside,

    Casey Irwin PARK VIEW REALTY INC

    30 Moree Loop Unit 39, Winter Springs, FL 32708
  • /39

    $299,000

    • 3 Beds
    • 1 Bath
    • 945 Sq Ft

    150 N Cortez Ave, Winter Springs, FL 32708

    PRICE DROP-Move-In Ready! Beautifully Remodeled 3-Bedroom Home with No HOAWelcome to this charming and fully remodeled 3-bedroom, 1-bath home located in the heart of Winter Springs! Centrally situated near top-rated schools, shopping, dining, and just minutes from scenic bike and walking trails, this home offers the perfect blend of convenience and comfort. Enjoy quick access to I-4 and the

    Robert McGrew, PA FLAT FEE REAL ESTATE SERVICES LLC

    150 N Cortez Ave, Winter Springs, FL 32708
  • /60

    $265,000

    • 2 Beds
    • 2.5 Baths
    • 1,156 Sq Ft

    611 Casa Park Ct N Unit G, Winter Springs, FL 32708

    **Prime Location! Exquisite 2-Bed, 2.5-Bath Renovated Townhome** NEW Windows plumbing, flooring, kitchen,bathrooms, stairs, closets, and painted.Step into your dream home! This stunning, fully updated townhome is nestled in a highly sought-after neighborhood, offering the perfect blend of modern elegance and comfort. The chef's kitchen dazzles with gorgeous countertops, sleek new

    William Grim, III RE/MAX ASSURED

    611 Casa Park Ct N Unit G, Winter Springs, FL 32708
  • /50

    $298,990

    • 2 Beds
    • 2 Baths
    • 1,166 Sq Ft

    718 Lakeside Dr, Winter Springs, FL 32708

    Welcome to 718 LAKESIDE Drive in the heart of Winter Springs! This beautifully move in ready 2-bedroom, 2-bath Home perfectly blends style, comfort, and convenience. As you step inside, you are greeted by a BRIGHT OPEN LIVING SPACE with VAULTED CEILINGS, UPDATED FIXTURE, STYLIST NEWER LAMINATE FLOORING, and a COZY FIREPLACE that instantly makes the home feel warm and inviting. The spacious

    Mariana Cisneros PREMIUM PROPERTIES R.E SERVICE

    718 Lakeside Dr, Winter Springs, FL 32708
  • /27

    $250,000

    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft

    498 Club Dr, Winter Springs, FL 32708

    Welcome to Cypress Club, a townhome community located in The Highlands within Winter Springs. Two bedrooms/two bath home is two stories offering split bedrooms. The living room/dining room combo provides high lofty ceilings with celestial windows providing natural sunlight to the home. Sliding glass doors open to a screen enclosed patio to the rear of the property that overlooks Winter Springs

    Joyce Gary PAINE-ANDERSON PROPERTIES, INC

    498 Club Dr, Winter Springs, FL 32708
  • /16

    $299,900

    • 3 Beds
    • 3 Baths
    • 1,697 Sq Ft

    600 Northern Way Unit 901, Winter Springs, FL 32708

    Are you looking for an Affordable Turnkey Property? This Unit makes you feel like you're living in a model home. It has the flexibility to be used for Multi-Generational living as this property has three En-suites with one of the Bedrooms downstairs, perfect for a mother in law suite. The rooms are large and you will see upgrades throughout with granite counters, luxury vinyl flooring, updated

    Ryan Minadie COLDWELL BANKER RESIDENTIAL RE

    600 Northern Way Unit 901, Winter Springs, FL 32708
  • /29

    $275,000

    • 3 Beds
    • 2 Baths
    • 1,101 Sq Ft

    435 Horizon Dr, Winter Springs, FL 32708

    Welcome to this charming 3-bedroom, 2-bath home nestled in the desirable SEASONS THE community! From the moment you step inside, you'll appreciate the bright and airy feel, with tile flooring throughout and all major appliances—including a washer and dryer—already in place for your convenience. With spacious rooms and a smart, functional layout, this home offers a solid foundation and endless

    Megan Hedrick Mark Spain Real Estate

    435 Horizon Dr, Winter Springs, FL 32708
  • /42

    $299,900

    • 4 Beds
    • 1 Bath
    • 1,120 Sq Ft

    206 Charles St, Winter Springs, FL 32708

    Discover your dream home nestled in the heart of Winter Springs, a charming bungalow all on one floor, perfect for all family types. ALl new nuetral FRESH INTERIOR PAINT! Split plan. Great eat in kitchen and floorplan! This enchanting single-family residence boasts four cozy bedrooms, offering a flexible split layout with the fourth bedroom conveniently situated off the kitchen. This versatile

    Laurie Cash Cain CHARLES RUTENBERG REALTY ORLANDO

    206 Charles St, Winter Springs, FL 32708
  • /28

    $295,000

    • 2 Beds
    • 2.5 Baths
    • 1,330 Sq Ft

    4113 Hedge Maple Place Unit 4113, Winter Springs, FL 32708

    If you are looking for a Gated Community with the most desirable location in the community you know you have found it! This home boosts an open floorplan that includes a breakfast bar and open to the family and dining area on the main floor, with high ceilings and lots of natural light. Upgraded appliances, kitchen countertops, and flooring. This floor plan offers two spacious master suites

    Susan Pinnock A+ REALTY PROFESSIONALS, INC

    4113 Hedge Maple Place Unit 4113, Winter Springs, FL 32708
  • /29

    $240,000

    • 3 Beds
    • 1.5 Baths
    • 1,105 Sq Ft

    4443 Brook Hollow Cir Unit 19A, Winter Springs, FL 32708

    Welcome your charming townhome nestled in the heart of Winter Springs in the desirable Deer Run community! Located in a top-rated school district, this well-maintained home offers the perfect blend of comfort, convenience, and peace of mind. Step inside to discover recent upgrades including impact resistant hurricane windows (2022), newer roof (2019), and a beautifully renovated shower. With no

    Amber Burt THE SIMON SIMAAN GROUP

    4443 Brook Hollow Cir Unit 19A, Winter Springs, FL 32708
  • /45

    $284,900

    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft

    424 Club Dr, Winter Springs, FL 32708

    Welcome to this well-maintained 3-bedroom, 2-bath home located in the desirable Cypress Club community of Winter Springs. Nestled in a peaceful neighborhood, this inviting residence offers comfortable living with access to a host of amenities that make every day feel like a getaway.Enjoy spacious living areas, a functional layout, and thoughtful updates throughout. The primary suite

    Lee Sloan KELLER WILLIAMS ADVANTAGE REALTY

    424 Club Dr, Winter Springs, FL 32708
  • /22

    $260,000

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft

    294 San Gabriel St, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. Charming 2-bedroom, 2-bath, Move-In-Ready home featuring an open living and dining area with vaulted ceilings, stylish new laminate flooring, outside storage room, plus the convenience of an inside laundry. With a few finishing touches, this property can truly shine making it a smart investment or a perfect place to call your own. Roof 2018, Water

    Christine Schneider RE/MAX TOWN & COUNTRY REALTY

    294 San Gabriel St, Winter Springs, FL 32708
  • /32

    $248,500

    • 3 Beds
    • 2 Baths
    • 1,187 Sq Ft

    429 Sheoah Blvd Unit 8, Winter Springs, FL 32708

    Discover Your Dream Home! Welcome to this stunning 3-bedroom, 2-bathroom condo, nestled on the serene 2nd floor. Recently updated to enhance your living experience, this residence boasts fresh interior paint and brand-new floor throughout, ensuring a move-in ready condition that invites comfort and style. The spacious living room and dining area merge seamlessly, featuring a charming wet

    Elizabeth Dowell UPZEL REALTY LLC

    429 Sheoah Blvd Unit 8, Winter Springs, FL 32708
  • /46

    $284,900

    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft

    600 Northern Way Unit 502, Winter Springs, FL 32708

    Location! Location! Location! This pristine condo nestled in the heart of Tuscawilla offers an incredible opportunity for low maintenance living in a serene and gated community. Enjoy summer days by the beautiful community pool and relax in the cabana. Across the way you will find access to Trotwood Park, with its picturesque settings ideal for picnics and recreational activities. Featuring a

    Robert Bretz, PA EXP REALTY LLC

    600 Northern Way Unit 502, Winter Springs, FL 32708
  • /32

    $252,500

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

    4530 Brook Hollow Cir, Winter Springs, FL 32708

    Brand New Central A/C replaced on Thursday, 8/21/25 MOTIVATED SELLER... Seller is willing to contribute to buyer(s)closing costs, pre-paid items, 2/1 buy-down, etc, up to $6,000.00 with full price offer and closing. .Move-In Ready, well maintained, 2 bedroom/2.5 bathroom townhome, designed for both comfort and convenience. 2 upstairs bathrooms have been updated with new vanities,

    Debra Rizzuto EDISON REAL ESTATE SERVICES

    4530 Brook Hollow Cir, Winter Springs, FL 32708
  • /3

    $249,000

    • Land
    • 0.29 Acre
    • $858,621 per Acre

    0 434th Unit MFRS5100991, Winter Springs, FL 32708

    Affordable small site on busy SR 434 with 100ft of frontage. This lot is ideal for an Automotive Car Lot or a small retail use. Easy Access to HWY 17-92, 427, 419, 417 and I-4.

    Rose Soto EMPIRE REALTY & MANAGEMENT SERVICES

    0 434th Unit MFRS5100991, Winter Springs, FL 32708
  • /34

    $269,000

    • 3 Beds
    • 2.5 Baths
    • 2,564 Sq Ft

    1754 Lake St, Oviedo, FL 32765

    Here's your chance to secure a rare waterfront property with incredible potential in one of Oviedo's most scenic corridors. Located on Lake Jessup, 1754 Lake Street offers direct lake access, a sizable 2,500+ sq. ft. footprint, and sits on an oversized lot ideal for redevelopment or high-end renovation.The 3-bedroom, 2-bathroom home has sustained hurricane damage/flooding. With a private

    John Chiumento LPT REALTY, LLC

    1754 Lake St, Oviedo, FL 32765

Home Trends in Winter Springs, FL

Housing Trends

Median Sale Price
$420,000
Median Single Family Sale Price
$429,950
Median Townhouse Sale Price
$417,000
Median 2 Bedroom Sale Price
$175,000
Median 1 Bedroom Sale Price
$155,000
Average Price Per Sq Ft
$246
Number of Homes for Sale
150
Last 12 months Home Sales
617
Months of Supply
2.90
Median List Price
$429,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-3%
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