Highlands Homes

• 

  

  

  /15

  $189,500

  • 2 Beds
  • 2 Baths
  • 972 Sq Ft

  10 Sheoah Blvd Unit 5, Winter Springs, FL 32708

  Prime First-Floor Living in Prestigious Highlands of Winter Springs!Discover the ultimate in convenient living with this exceptional first-floor 2 bedroom, 2 bathroom condo in the highly sought-after Highlands community. Located in top-rated Seminole County School District, this ground-level gem eliminates the hassle of stairs while offering effortless accessibility for residents and

  Matt Merdian MERDIAN REALTY LLC

  10 Sheoah Blvd Unit 5, Winter Springs, FL 32708
• 

  

  

  /20

  $2,300 per month

  • 3 Beds
  • 2 Baths
  • 1,161 Sq Ft
  • House for Rent

  526 Seasons Ct, Winter Springs, FL 32708

  Property Id: 2121780Welcome to this beautifully updated 3-bedroom, 2-bath single-family home in the heart of Winter Springs, FL. Built in 1998 and freshly renovated, this home features brand new luxury vinyl plank flooring, modern kitchen cabinets topped with quartz countertops, a new refrigerator, updated bathroom vanities, and fresh interior and exterior paint.Enjoy a bright,

  526 Seasons Ct, Winter Springs, FL 32708
• 

  

  /2

  $420,000 Sold Jul 30, 2025

  • 1,756 Sq Ft
  • $239/SF
  • 120 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1985

  509 Osprey Ln, Winter Springs, FL 32708

  BRAND NEW TILE ROOF!! The buyer will enjoy lasting value, durability and low maintenance protection for 40+ years! Looking for a home that blends convenience, comfort, and access to a highly rated Seminole County school district? This is the one for you! This beautiful 3-bedroom, 2.5-bathroom home is nestled in the desirable Greenspointe subdivision in The Highlands of Winter Springs. Situated on

  Tricia Daigle CENTURY 21 MCBRIDE REALTY GROUP

  509 Osprey Ln, Winter Springs, FL 32708
• 

  

  

  /54

  Est $275,568 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,069 Sq Ft

  421 Horizon Dr, Winter Springs, FL 32708

  421 Horizon Dr, Winter Springs, FL 32708
• 

  

  

  /53

  $315,000

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

  515 Seasons Ct, Winter Springs, FL 32708

  **One or more photo(s) has been virtually staged**. Welcome to this beautifully remodeled 3-bedroom, 2-bathroom home located in the sought-after area of Winter Springs, known for its top-rated schools.Inside, you’ll find a modern open layout starting with a spacious living room that flows seamlessly to the private patio. To the right, the brand-new kitchen and dining area combo feature

  Olga Carballea Diaz CHARLES RUTENBERG REALTY ORLANDO

  515 Seasons Ct, Winter Springs, FL 32708
• 

  

  /20

  $1,449 per month

  • 2 Beds
  • 1.5 Baths
  • 1,080 Sq Ft
  • Townhouse for Rent

  250 Moree Loop Unit 6, Winter Springs, FL 32708

  Available for move-in 9/17. Close to shopping and restaurants and A+ schools. This townhome has 2 bedrooms and 1.5 bathrooms. This beautiful home has ceramic tile flooring throughout the downstairs with a living room/dining room/kitchen combination and a half bath downstairs. The large kitchen has a breakfast bar and floor-to-ceiling window that offers great morning natural light. Both bedrooms

  Steve Simpson 407 PROPERTIES

  250 Moree Loop Unit 6, Winter Springs, FL 32708
• 

  /2

  $379,900 Sold Jul 28, 2025

  • 1,551 Sq Ft
  • $245/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1990

  302 Cello Cir, Winter Springs, FL 32708

  TERRIFIC HOME LOCATED ON A TREED CORNER LOT JUST WAITING FOR A NEW FAMILY TO CALL IT HOME. FRESHLY PAINTED EXTERIOR AND A NEW ROOF IS IN PROCESS (PERMITS). THE POPULAR FLOOR PLAN IS IDEAL WITH A SEPARATE LIVING AND FAMILY ROOMS, UPDATED KITCHEN AND APPLIANCES, BREAKFAST AREA WITH LARGE PANTRY AND BUILT IN DESK ROUNDING OUT THE HOME IS 3 BEDROOMS AND 2 FULL BATHS. FENCED YARD IS IDEAL FOR PETS.

  Kim Carthen CARTHEN REALTY INC

  302 Cello Cir, Winter Springs, FL 32708
• 

  

  /35

  Est $255,459 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft

  510 Club Dr, Winter Springs, FL 32708

  510 Club Dr, Winter Springs, FL 32708
• 

  

  /82

  $17,000

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft

  417 El Paso Way, Winter Springs, FL 32708

  Lot rent is $1184.11/mo includes Cable w/ 1gig internet, all amenities, Ave water bill is $8-$15/mo

  Ryan Call

  417 El Paso Way, Winter Springs, FL 32708
• 

  

  /25

  $2,145 per month

  • 3 Beds
  • 2 Baths
  • 1,146 Sq Ft
  • House for Rent

  218 Perth Ct, Winter Springs, FL 32708

  Totally Renovated 3BR/2BA Duplex in Winter Springs Quiet Cul-de-Sac!Welcome to this beautifully updated 3-bedroom, 2-bathroom duplex offering 1,146 sq ft of modern living in the highly desirable Winter Springs community. Nestled in a peaceful cul-de-sac, this home blends style, comfort, and convenience.Property Highlights (Unit B):- Completely renovated interior with brand new

  218 Perth Ct, Winter Springs, FL 32708
• 

  /2

  $170,000 Sold Jul 25, 2025

  • 1,187 Sq Ft
  • $143/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  240 Moree Loop Unit 5, Winter Springs, FL 32708

  ?? Welcome Home to 240 Moree Loop, Unit 5 – Casselberry’s Hidden Gem! ??Step into comfort and style in this beautifully maintained 2-bedroom, 2-bath condo perfectly nestled in the heart of Casselberry. Offering a blend of functionality and charm, this spacious unit is ideal whether you’re a first-time buyer, investor, or looking to downsize without compromising on lifestyle.?

  Richard Sherrod Jr EXP REALTY LLC

  240 Moree Loop Unit 5, Winter Springs, FL 32708
• 

  

  /26

  Est $400,143 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,908 Sq Ft

  523 Shane Cir, Winter Springs, FL 32708

  523 Shane Cir, Winter Springs, FL 32708
• 

  

  /27

  $239,499

  • 2 Beds
  • 1.5 Baths
  • 896 Sq Ft

  122 Kristi Ann Ct, Winter Springs, FL 32708

  ***SELLER CONSCESSION UP TO $4000 TOWARDS BUYERS CLOSING COSTS!!*** Stunning fully remodeled townhome featuring top-quality finishes and modern design throughout! Enjoy SEa 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.

  Vered Thacker DALTON WADE INC

  122 Kristi Ann Ct, Winter Springs, FL 32708
• 

  

  /26

  $2,450 per month

  • 3 Beds
  • 2 Baths
  • 1,693 Sq Ft
  • House for Rent

  767 S Edgemon Ave, Winter Springs, FL 32708

  Welcome to the beautiful and peaceful city of Winter Springs. This 3/2 home sits on a large, corner lot with a very spacious fenced-in backyard. Inside, you can enjoy a split floor plan that divides the living room/dining room with a separate family room. A remodeled kitchen features granite countertops, stainless steel appliances, and tile flooring and backsplash. A new and fresh coat of paint

  Peter Dang ALLIANCE RENTAL HOMES

  767 S Edgemon Ave, Winter Springs, FL 32708
• 

  /2

  $230,000 Sold Jul 25, 2025

  • 1,434 Sq Ft
  • $160/SF
  • 78 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1983

  503 Moree Loop, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. WOW!!! Move-In Ready Townhome in Winter Springs – Just \$166.67/SqFt!Experience the perfect combination of charm, comfort, and value in this beautifully maintained 2-bedroom, 2-bathroom townhome, nestled in one of Winter Springs’ most desirable communities. Designed with both style and practicality in mind, this home offers a spacious floor plan

  Javier Paredes PROPERTIES IN TOWN

  503 Moree Loop, Winter Springs, FL 32708
• 

  

  /38

  Est $976,823 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,956 Sq Ft

  150 E Bahama Rd, Winter Springs, FL 32708

  150 E Bahama Rd, Winter Springs, FL 32708
• 

  

  /37

  $525,000

  • 4 Beds
  • 2.5 Baths
  • 2,092 Sq Ft

  431 S Hawthorn Cir, Winter Springs, FL 32708

  **Single-Family Home with Detached ADU & Pool**Tucked away in a quiet cul-de-sac, this over 2,000 sq. ft. home with a detached Accessory Dwelling Unit (ADU) is a rare find in the highly desirable, non-HOA community of North Orlando Terrace! NEWER ROOF (2022), as well as a massive remodel in 2023 that consisted of NEW kitchen, bathrooms, plumbing, electrical panel, interior/exterior paint,

  Elliot Shugan THE SHUGAN GROUP INC

  431 S Hawthorn Cir, Winter Springs, FL 32708
• 

  

  /39

  $2,450 per month

  • 3 Beds
  • 2 Baths
  • 1,401 Sq Ft
  • House for Rent

  302 Bridie Ct, Winter Springs, FL 32708

  3 Bedroom, 2 1/2 Bath Single Family Home For Rent in Winter Springs, FL 32708. Range, Refrigerator, D/W, Disposal, Central Heat and A/C.

  Rick Sein REALSOURCE PROPERTY MANGNT LLC

  302 Bridie Ct, Winter Springs, FL 32708
• 

  /2

  $260,000 Sold Jul 24, 2025

  • 1,334 Sq Ft
  • $195/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  422 S Hawthorn Cir Unit 2, Winter Springs, FL 32708

  Investor special or perfect for buyers looking to add their personal touch! This 3-bedroom, 2-bathroom pool home is a rare find in a well-established, no-HOA neighborhood. Sitting on a lush lot with a tranquil pond and no rear neighbors, it offers privacy and potential. The large pool and covered patio are ideal for creating your own backyard oasis. With solid bones and great location, this home

  Antonio Salinger CALL IT CLOSED INTL REALTY

  422 S Hawthorn Cir Unit 2, Winter Springs, FL 32708
• 

  

  /30

  Est $313,118 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,426 Sq Ft

  711 Lakeside Dr, Winter Springs, FL 32708

  711 Lakeside Dr, Winter Springs, FL 32708
• 

  

  /26

  $245,000

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

  411 Green Spring Cir, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. Lock in lower payments! This home qualifies for a lender-paid 2/1 buydown, giving you interest rates in the high 4’s for the first year and the high 5’s for the second year when financing through the designated lender. Or You Can Make the Home Your Own With a Conventional or FHA RENOVATION LOAN!. Opportunity knocks in the Vineyards of Mount

  Sarita Cabrera WATSON REALTY CORP

  411 Green Spring Cir, Winter Springs, FL 32708
• 

  

  /23

  $1,970 per month

  • 3 Beds
  • 2 Baths
  • 1,098 Sq Ft
  • House for Rent

  135 Cortez Ct, Winter Springs, FL 32708

  Tucked away on a quiet cul-de-sac in the desirable Winter Springs area, this well-maintained home offers comfort, space, and a fantastic location — perfect for families or anyone seeking a peaceful lifestyle close to everything.Features include:Bright and welcoming interior with neutral paint tonesSpacious screened-in porch, ideal for relaxing or entertainingFully fenced backyard

  Vivian Lippi LIPPI REALTY LLC

  135 Cortez Ct, Winter Springs, FL 32708
• 

  /2

  $345,000 Sold Jul 24, 2025

  • 1,609 Sq Ft
  • $214/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  110 S Edgemon Ave, Winter Springs, FL 32708

  **MULTIPLE OFFERS RECEIVED - SUBMIT HIGHEST AND BEST BY TUESDAY AT 3PM** Welcome to this cozy and well-maintained 3-bedroom, 2-bathroom single family home perfectly situated on a spacious corner lot with no HOA! Featuring a large fenced backyard with a deck, shed, and newly added awning, this outdoor space is ideal for entertaining, relaxing, or gardening.Inside, you’ll find the kitchen

  Valentina Calla MAINFRAME REAL ESTATE

  110 S Edgemon Ave, Winter Springs, FL 32708
• 

  

  /31

  Est $282,559 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,089 Sq Ft

  268 San Gabriel St, Winter Springs, FL 32708

  268 San Gabriel St, Winter Springs, FL 32708
• 

  

  /56

  $49,900

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  365 Casa Grande Ct, Winter Springs, FL 32708

  Home has an open feeling-nice layout, nice side screened-in porch with open patio. Beautiful corner lot! Area close to major highways, shopping, doctors, restaurants, police, fire station, etc. Hacienda Village is a Legacy Community, 55+. Base Lot rent is $1025. This Community offers lots of amenities -something to do all of the time. "YOU WON'T BE BORED!"

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  365 Casa Grande Ct, Winter Springs, FL 32708
• 

  

  /13

  $2,500 per month

  • 3 Beds
  • 2.5 Baths
  • 2,010 Sq Ft
  • House for Rent

  633 White Ibis Ct, Winter Springs, FL 32708

  Located in the highly desirable city of Winter Springs, this gorgeous updated one story 3 bedroom, 2 bath home is calling your name! Two car garage! Upon entry, you are greeted with a beautiful living room upgraded foyer lighting, To the left you have your master suite with large master bathroom which includes private water closet, stand-up shower, brand new tub, brand new double vanities with

  Yousong Liu SUNSHINE GROUP USA, INC

  633 White Ibis Ct, Winter Springs, FL 32708
• 

  /2

  $262,000 Sold Jul 24, 2025

  • 1,086 Sq Ft
  • $241/SF
  • 19 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1989

  283 Woodgreen Ln, Winter Springs, FL 32708

  Discover this beautifully updated 2-bedroom, 1.5-bath townhome in the highly sought-after Mount Greenwood community of Winter Springs. This move-in ready unit has over $30K in modern upgrades that include wood laminate flooring throughout, new baseboards, stylishly updated bathrooms featuring a sleek pedestal sink in the half bath, and a fully renovated main bathroom with a new shower/tub combo,

  Zac Hernandez EMPIRE NETWORK REALTY

  283 Woodgreen Ln, Winter Springs, FL 32708
• 

  

  /23

  Est $329,529 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft

  415 Harbor Winds Ct, Winter Springs, FL 32708

  415 Harbor Winds Ct, Winter Springs, FL 32708
• 

  

  /59

  $58,900

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

  209 El Camino Real Cir, Winter Springs, FL 32708

  This home was completely remodeled in 2020. The current owner put in a generator, plus wiring in the outside panel. Gutters 024. Roof coated in 2023, new AC 2020, Hot Water tank in newer. Newer pump for irrigation system, newer vapor barrier, ducts & water proofing in 2024.Kitchen and baths plus flooring updated around 2020. Hacienda Village has been updated with a Pickleball Court, Putt

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  209 El Camino Real Cir, Winter Springs, FL 32708
• 

  

  /31

  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft
  • Townhouse for Rent

  474 Club Dr, Winter Springs, FL 32708

  Lovely 3 bedroom, 2 bathroom townhome located in the peaceful and well-maintained Cypress Club community in Winter Springs, Florida. This home features a split-bedroom layout with two bedrooms and a full bathroom upstairs, complete with a garden tub and separate shower, and one bedroom with a full bathroom downstairs ideal for guests, extended family, or a home office setup. The living and dining

  Oscar Fonseca JEMCO REALTY & PROPERTY MANAGEMENT

  474 Club Dr, Winter Springs, FL 32708
• 

  /2

  $199,900 Sold Jul 22, 2025

  • 1,343 Sq Ft
  • $149/SF
  • 32 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1978

  429 Sheoah Blvd Unit 3, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. BACK TO MARKET: Buyer did not make the Deposit - UNIQUE GEM in sought-after Winter Springs! This beautifully maintained 2-bedroom, 2-bath CORNER UNIT stands out with special upgrades and a flexible layout that can easily CONVERT to a 3-BEDROOM. Nestled on the second floor with NO UPSTAIRS NEIGHBORS, this home offers peace, PRIVACY, and stunning

  Marielle Parra COMPASS FLORIDA LLC

  429 Sheoah Blvd Unit 3, Winter Springs, FL 32708
• 

  

  /22

  Est $319,388 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft

  463 Harbor Winds Ct, Winter Springs, FL 32708

  463 Harbor Winds Ct, Winter Springs, FL 32708
• 

  

  /54

  $69,900

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  294 Casa Grande Dr, Winter Springs, FL 32708

  Home completely remodeled, dry wall and knock down ceilings. Newer appliances, newer windows' siding, newer AC, great sunroom/Florida Room enclosed 12X20. Home backs up to privacy, creek and greenery. Hacienda is a Legacy Community 55+ close to major highways, Disney and the beaches, shopping, doctors, restaurants, etc. Monthly basic rent is $1025.00

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  294 Casa Grande Dr, Winter Springs, FL 32708
• 

  

  /27

  $1,495 per month

  • 2 Beds
  • 2 Baths
  • 972 Sq Ft
  • Condo for Rent

  10 Sheoah Blvd Unit 7, Winter Springs, FL 32708

  Spacious and bright 2 bedroom 2 bathroom condo for rent at The Highlands in Winter Springs. Just repainted throughout entire interior. Large family room with a small dining area. The two bedrooms on a split floor plan. The large master bedroom has sliding doors that lead to patio. The second, smaller, bedroom has its set of sliding doors leading to the screened-in porch and it's own bathroom.

  Rafael Pierluisi ALFANO PROPERTY MANAGEMENT

  10 Sheoah Blvd Unit 7, Winter Springs, FL 32708
• 

  /2

  $335,000 Sold Jul 18, 2025

  • 1,630 Sq Ft
  • $206/SF
  • 3 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1979

  170 N Fairfax Ave, Winter Springs, FL 32708

  Handyman special- Beautiful 5 bedroom 3 bath home in Winter Springs, Florida. With the right owner this home could be paradise. Sit out on your front porch and and enjoy the lake/park view. Beautiful paved driveway can hold 6 cars and front porch is paved. Boat or trailer parking on side of house. Relax in the backyard with in your jacuzzi, Entertain guest with your outdoor bar, bathroom, shower,

  Robert McGrew, PA FLAT FEE REAL ESTATE SERVICES LLC

  170 N Fairfax Ave, Winter Springs, FL 32708
• 

  

  /17

  Est $347,186 Not Listed For Sale

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

  403 Harbor Winds Ct, Winter Springs, FL 32708

  403 Harbor Winds Ct, Winter Springs, FL 32708
• 

  

  /31

  $225,000

  • 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
• 

  

  /16

  $2,100 per month

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • House for Rent

  705 Woodlawn Dr, Winter Springs, FL 32708

  Looking for your dream home? Through our seamless leasing process, this beautifully designed home is move-in ready. Our spacious layout is perfect for comfortable living that you can enjoy with your pets too; we’re proud to be pet friendly. Our homes are built using high-quality, eco-friendly materials with neutral paint colors, updated fixtures, and energy-efficient appliances. Enjoy the

  Nico Silva Vanegas MAIN STREET RENEWAL LLC

  705 Woodlawn Dr, Winter Springs, FL 32708
• 

  /2

  $200,000 Sold Jul 18, 2025

  • 1,008 Sq Ft
  • $198/SF
  • 15 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  315 Panama Cir, Winter Springs, FL 32708

  This delightful 2-bedroom, 2-bathroom single-family home has comfort and charm in a prime Winter Springs location. Built in 1980, the residence provides 1,008 sq ft of living space on a spacious 9,757 sq ft lot. The home features durable cement/concrete construction, a composition roof, and an attached garage. Located in a well-established neighborhood, it has convenient access to top-rated

  Steven Koleno BEYCOME OF FLORIDA LLC

  315 Panama Cir, Winter Springs, FL 32708
• 

  

  /77

  Est $330,777 Not Listed For Sale

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

  447 Harbor Winds Ct, Winter Springs, FL 32708

  447 Harbor Winds Ct, Winter Springs, FL 32708

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