Highlands Homes

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  $310,500 Open Sat 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,470 Sq Ft

  737 Tanglewood Rd, Winter Springs, FL 32708

  Welcome to your new home! This charming 3-bedroom, 2-bathroom home also features a versatile flex room—perfect as a 4th bedroom or home office. The open layout and vaulted ceilings create a spacious, airy feel throughout, while the inviting sunken living room, complete with a cozy wood-burning fireplace, is perfect for relaxing on cool evenings. The custom-designed kitchen is a true highlight,

  

  Martha Grasty

  RE/MAX ASSURED

  (321) 496-7412

  737 Tanglewood Rd, Winter Springs, FL 32708
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  Explore Highlands

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  /98

  $1,153 - $3,490 per month

  The Avenues at Winter Springs

  1 - 3 Beds

  1 Laurel Oaks Dr, Winter Springs, FL 32708

  The Avenues at Winter Springs offer a tranquil living experience in Winter Springs, FL, blending comfort, convenience, and affordability. Nestled in a serene residential area, residents enjoy peaceful surroundings while remaining conveniently close to Interstate 4 and the vibrant Uptown Altamonte Springs area. With easy access to shopping, dining, and entertainment options, residents can explore

  1 Laurel Oaks Dr, Winter Springs, FL 32708
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  /2

  $325,000 Sold Sep 03, 2025

  • 1,458 Sq Ft
  • $223/SF
  • 25 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1971

  210 Wade St, Winter Springs, FL 32708

  Price Reduction! Welcome to this cozy and functional home in the heart of Winter Springs! A great layout with stainless steel kitchen appliances (all included!) give the space a clean, modern feel. The kitchen features granite countertops and a cozy eat-in dinette—perfect for casual meals or your morning coffee.You'll love the plush new carpeting in the bedrooms, a spacious master suite

  Kimberley Beaudry ORLANDO REGIONAL REALTY

  210 Wade St, Winter Springs, FL 32708
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  /19

  Est $187,728 Not Listed For Sale

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

  40 Sheoah Blvd Unit 25, Winter Springs, FL 32708

  40 Sheoah Blvd Unit 25, Winter Springs, FL 32708
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  /58

  $365,000

  • 3 Beds
  • 2 Baths
  • 1,387 Sq Ft

  45 S Edgemon Ave, Winter Springs, FL 32708

  LOCATION LOCATION LOCATION This charming fully renovated home offers 3-bedroom, 2-bathroom home featuring 1,387 sqft of stylish living space. This property boasts brand-new cabinets, elegant quartz countertops, Brand new stainless steel appliances, cozy fireplace, and sleek laminate flooring throughout. Brand new roof. Enjoy outdoor living at its best with an in-ground pool perfect for

  

  John Gomez

  EXP REALTY LLC

  (321) 385-8619

  45 S Edgemon Ave, Winter Springs, FL 32708
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  /17

  $2,149 per month

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • House for Rent

  762 S Edgemon Ave, Winter Springs, FL 32708

  Take a look at this lovely home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 2 car garage, fenced backyard, back screen porch and approximately 1,008 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user)

  Cathy Behe TAH FLORIDA LLC

  762 S Edgemon Ave, Winter Springs, FL 32708
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  /2

  $255,000 Sold Sep 02, 2025

  • 1,363 Sq Ft
  • $187/SF
  • 2 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1989

  426 Green Spring Cir, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. Tucked away in the desirable Mount Greenwood community of Winter Springs, this end-unit townhome offers comfort, privacy, and a thoughtful layout. Step inside to a welcoming main living area. The kitchen features granite countertops, stainless steel appliances, and a cozy eat-in space, with a breakfast bar that flows seamlessly into the dining room.

  Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

  426 Green Spring Cir, Winter Springs, FL 32708
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  /30

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,674 Sq Ft

  7 N Edgemon Ave Unit 7-9, Winter Springs, FL 32708

  7 N Edgemon Ave Unit 7-9, Winter Springs, FL 32708
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  /36

  $269,900 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,452 Sq Ft

  533 Moree Loop, Winter Springs, FL 32708

  Under contract-accepting backup offers. Tucked away in a peaceful, wooded setting, this 2-bedroom, 2.5-bathroom end-unit townhome offers the ultimate peaceful retreat in Winter Springs. Step through the fenced courtyard and inside to a bright and welcoming foyer that leads to a spacious, sunlit living room with a cozy fireplace overlooking the private backyard. The dining area flows into a

  Brad Young HOMEVEST REALTY

  533 Moree Loop, Winter Springs, FL 32708
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  /31

  $1,100 - $1,600 per month

  Mosswood

  Studio - 2 Beds

  101 Mosswood Cir, Winter Springs, FL 32708

  Welcome to Mosswood Apartments! At Mosswood, you'll find comfortable apartments with washer/dryer connections & extra storage. We're located just north of Orlando in Winter Springs, FL. Come home to our quiet residential setting & lake views that have easy access to I-417 and public transportation. Our single-story, villa-style East Winter Springs apartments feature private entrances and patios

  101 Mosswood Cir, Winter Springs, FL 32708
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  /2

  $331,000 Sold Sep 02, 2025

  • 1,136 Sq Ft
  • $291/SF
  • 3 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1980

  701 Woodlawn Dr, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. Welcome to your exquisitely renovated 4-bedroom, 2-bathroom pool home at 701 Woodlawn Drive, situated in the highly sought-after Wildwood neighborhood of Winter Springs! Fully renovated in July 2025, this residence embodies refined style and turnkey comfort.As you enter, you’re greeted by a bright, open floor plan showcasing stylish shaker-style

  Eric Campbell LPT REALTY, LLC

  701 Woodlawn Dr, Winter Springs, FL 32708
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  /16

  Est $155,506 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 759 Sq Ft

  354 San Rafael St Unit 354, Winter Springs, FL 32708

  354 San Rafael St Unit 354, Winter Springs, FL 32708
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  /36

  $395,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,672 Sq Ft

  678 Wishaw Ln, Winter Springs, FL 32708

  Welcome to your renovated home in the great Winter Springs location! This home features 3 bed/2 bath, ceramic title throughout the entire home. New kitchen with granite countertops and brand-new stainless-steel appliances. A large fireplace in the living room gives the home a cozy environment. Renovated bathrooms with new vanities and granite countertops. The renovation also includes modern

  Alejandro Rodriguez AROD PARTNERS REALTY

  678 Wishaw Ln, Winter Springs, FL 32708
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  /9

  $1,900 per month

  • 4 Beds
  • 2.5 Baths
  • 1,405 Sq Ft
  • House for Rent

  201 Bennett St, Winter Springs, FL 32708

  Four bedroom house in Winter Springs. Close to everything. Nice fenced in back yard.

  Mike Northam NORTHAM REALTY, LLC

  201 Bennett St, Winter Springs, FL 32708
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  /2

  $330,000 Sold Aug 29, 2025

  • 1,680 Sq Ft
  • $196/SF
  • 64 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2008

  479 Harbor Winds Ct, Winter Springs, FL 32708

  Beautiful Townhome in Gated Harbor Winds – Prime Location & Resort-Style Amenities! Don’t miss this opportunity to own a beautifully maintained 3-bedroom, 2.5-bathroom townhome located in the highly desirable gated community of Harbor Winds in Winter Springs. This spacious 1,680 sq. ft. home offers an open, airy floor plan designed for both comfort and functionality. The primary suite is

  Ryan Rogers EXP REALTY LLC

  479 Harbor Winds Ct, Winter Springs, FL 32708
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  /24

  Est $426,713 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  669 Seven Oaks Blvd, Winter Springs, FL 32708

  669 Seven Oaks Blvd, Winter Springs, FL 32708
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  /25

  $399,900

  • 4 Beds
  • 2 Baths
  • 1,983 Sq Ft

  221 Albert St, Winter Springs, FL 32708

  This 4-bedroom, 2-bath home offers 1,983 sq. ft. of living space with an open layout connecting the family room, dining, and kitchen areas. The kitchen features a skylight and a peninsula that opens seamlessly to the family room, while a Florida room connects directly from the kitchen and leads out to the backyard deck with a 12x12 hardtop gazebo that conveys. Both bathrooms also have skylights,

  David Zambrano REDFIN CORPORATION

  221 Albert St, Winter Springs, FL 32708
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  /33

  $1,596 - $1,912 per month

  Seville on the Green

  1 - 3 Beds

  300 Sheoah Blvd, Winter Springs, FL 32708

  Find the life of sophistication and style that awaits you at Seville on the Green. Our Winter Springs community is nestled in the Highland Residential Neighborhood, right off of 434 and 17-92. We are minutes from I-4 and SR-417 and are less than six miles from major shopping and dining. We proudly offer one, two, and three-bedroom apartments with multiple floor plans. Select homes feature

  300 Sheoah Blvd, Winter Springs, FL 32708
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  /2

  $185,000 Sold Aug 28, 2025

  • 1,187 Sq Ft
  • $156/SF
  • 32 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  60 Moree Loop Unit 45, Winter Springs, FL 32708

  Uncover a Hidden Gem in Central Florida! Welcome to this charming FIRST FLOOR, single story, 3-bedroom, 2 bath condo nestled in the Highlands community, renowned for its exceptional recreational offerings. The kitchen boasts light-colored cabinets and in unit washer / dryer. Spacious open-concept living and dining areas seamlessly connect to a large screened patio, perfect for relaxation or

  Matt Merdian MERDIAN REALTY LLC

  60 Moree Loop Unit 45, Winter Springs, FL 32708
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  /2

  Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 2,293 Sq Ft

  660 Macduff Ln, Winter Springs, FL 32708

  660 Macduff Ln, Winter Springs, FL 32708
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  /32

  $345,000

  • 3 Beds
  • 2 Baths
  • 1,336 Sq Ft

  121 N Fairfax Ave, Winter Springs, FL 32708

  Beautiful 3 bedrooms 2 baths home in Winter Springs, Florida. Sit out on your front porch and enjoy the lake/park view. Beautiful, paved driveway can hold 2 cars. Relax in the backyard within big area. This home is minutes from all shopping, Interstate 4 and the 417-toll road. Close to the police station for added security. The back yard has turf grass. Kitchen was remolded new counter and

  Ruben Cabrera AVILA & ASSOCIATES REALTY

  121 N Fairfax Ave, Winter Springs, FL 32708
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  /36

  $3,000 per month

  • 3 Beds
  • 2.5 Baths
  • 1,695 Sq Ft
  • House for Rent

  510 Spoonbill Ct, Winter Springs, FL 32708

  Elevate your lifestyle at Greenspointe!?This sought-after Winter Springs community offers an abundance of amenities designed for relaxation and recreation: a clubhouse with gathering spaces, sparkling pool, tennis courts, parks, playground, beach volleyball, scenic walking trails, picnic pavilions, and open green spaces.Step inside and you’ll immediately notice the beautifully updated kitchen

  Liliana Lamadrid Sierra LA ROSA REALTY CW PROPERTIES L

  510 Spoonbill Ct, Winter Springs, FL 32708
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  /2

  $275,000 Sold Aug 27, 2025

  • 1,461 Sq Ft
  • $188/SF
  • 34 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1972

  609 David St, Winter Springs, FL 32708

  Location Location- 4 bedroom 2 bath - $290,000. Your new home awaits in this charming Winter Springs community. The property features open layout with a dining and kitchen combo. The kitchen is a blank canvas. Bring your tools to customize and potentially increase the property value. Situated in a convenient location, this home provides easy access to local amenities and attractions. Don't

  Steven Koleno BEYCOME OF FLORIDA LLC

  609 David St, Winter Springs, FL 32708
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  /6

  Est $269,529 Not Listed For Sale

  1360 Delaney Dr, Winter Springs, FL 32708

  1360 Delaney Dr, Winter Springs, FL 32708
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  /68

  $349,900

  • 4 Beds
  • 2 Baths
  • 1,604 Sq Ft

  221 N Devon Ave, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. Welcome to a stunning oasis in the heart of Winter Springs, where style meets convenience. This beautifully maintained 4-bedroom, 2-bathroom pool home has been updated to provide a bright and open floor plan, featuring durable laminate and ceramic tile flooring.This home features elegant Level 3 granite countertops in both the kitchen and

  Sara Nicholas, PA CHARLES RUTENBERG REALTY ORLANDO

  221 N Devon Ave, Winter Springs, FL 32708
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  /21

  $1,174 - $1,799 per month

  Moss Park

  1 - 4 Beds

  170 N Gardenridge Ct, Winter Springs, FL 32708

  Experience the many benefits of this Winter Springs apartment community, where we bring affordability, comfort, and convenience to home. Moss Park Apartments is located off Moss Park Road and State Road 434, approximately two miles east of Highway 17-92.Moss Park Apartments is a mixed-income community that offers apartment homes for unrestricted and restricted-income residents. Located

  170 N Gardenridge Ct, Winter Springs, FL 32708
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  /2

  $365,000 Sold Aug 26, 2025

  • 1,576 Sq Ft
  • $232/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1974

  416 S Hawthorn Cir, Winter Springs, FL 32708

  This FULLY RENOVATED home boasts stunning curb appeal and modern upgrades throughout. From the moment you arrive, you'll be delighted by the beautifully landscaped front yard and welcoming entryway. Situated on a large lot with a fully fenced, oversized backyard, featuring a newly resurfaced pool to enjoy on hot Summer days!This home offers a great floorplan with a neutral, light color

  Lisa Demarco Rubel KELLER WILLIAMS ADVANTAGE REALTY

  416 S Hawthorn Cir, Winter Springs, FL 32708
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  /27

  Est $142,495 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 710 Sq Ft

  30 Sheoah Blvd Unit 23, Winter Springs, FL 32708

  30 Sheoah Blvd Unit 23, Winter Springs, FL 32708
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  /45

  $425,000

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

  746 N Gretna Ct, Winter Springs, FL 32708

  Welcome to Your Dream Home in The Highlands of Winter Springs!This beautifully maintained residence offers everything you've been waiting for — and more! Featuring a desirable split-bedroom floor plan, this home boasts upgraded appliances, a brand-new HVAC system, and a bright, inviting family room perfect for gatherings or quiet evenings in.Enjoy Florida living at its best with a

  John Muccigrosso RE/MAX 200 REALTY

  746 N Gretna Ct, Winter Springs, FL 32708
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  /21

  $1,695 per month

  • 2 Beds
  • 1.5 Baths
  • 1,114 Sq Ft
  • Townhouse for Rent

  304 Woodgreen Ln Unit 2, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. Lovely Townhome with new windows in The Vineyards of Mt. Greenwood! Step into this charming, move-in-ready townhome offering an open-concept layout perfect for modern living. The spacious living room flows seamlessly into the bright eat-in kitchen, complete with quality cabinetry and well-maintained appliances—ideal for both everyday meals and

  Brian Lemay ROMAN REALTY GROUP, LLC

  304 Woodgreen Ln Unit 2, Winter Springs, FL 32708
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  /2

  $340,000 Sold Aug 18, 2025

  • 1,204 Sq Ft
  • $282/SF
  • 63 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1979

  620 Fruitwood Ave, Winter Springs, FL 32708

  Tucked away in a PEACEFUL and established Winter Springs neighborhood, this lovingly maintained 3-bedroom, 2-bath home offers the ideal balance of comfort, thoughtful updates, and everyday functionality—all with NO HOA and a welcoming community known for its friendly neighbors. Recent exterior UPGRADES include NEW gutters and landscaping (2024) and a NEW ROOF (2022), offering peace of mind and

  Jennifer Wemert WEMERT GROUP REALTY LLC

  620 Fruitwood Ave, Winter Springs, FL 32708
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  /20

  Est $193,518 Not Listed For Sale

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

  411 Sheoah Blvd Unit 43, Winter Springs, FL 32708

  411 Sheoah Blvd Unit 43, Winter Springs, FL 32708
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  /42

  $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
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  /6

  $1,800 per month

  • 2 Beds
  • 1.5 Baths
  • 896 Sq Ft
  • Townhouse for Rent

  130 Kristi Ann Ct, Winter Springs, FL 32708

  Welcome home to this 2 bed, 1.5 bath townhouse in the heart of Winter Springs. You will be just minutes away from the Winter Springs Town Center, Great Seminole County Schools, Coffee Shops, Premium Gyms, Center Winds Park, and multiple conveniences nearby. The living room and patio offer ample space for relaxation and entertainment. Each bedroom is designed for functionality, with ceiling fans

  130 Kristi Ann Ct, Winter Springs, FL 32708
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  /2

  $359,000 Sold Aug 12, 2025

  • 1,596 Sq Ft
  • $225/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1979

  739 Mimosa Ct, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. This elegant home is nestled in the desirable Foxmoor neighborhood, located in the heart of Winter Springs. It sits in a peaceful cul-de-sac, perfect for those who cherish tranquility and community.Upon entry, you'll be greeted by vaulted ceilings and a light, bright interior with a large living room and dining space. The interior of the

  Robin Cook WEST WING REAL ESTATE COMPANY

  739 Mimosa Ct, Winter Springs, FL 32708
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  /42

  Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 2,500 Sq Ft

  640 Macduff Ln, Winter Springs, FL 32708

  640 Macduff Ln, Winter Springs, FL 32708
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  /23

  $365,000

  • 3 Beds
  • 2 Baths
  • 1,168 Sq Ft

  409 Murphy Rd, Winter Springs, FL 32708

  In the heart of Winter Springs lies your next model home or your next short-term cash-flowing business!! This warm, cozy yet spacious home will make you fall in love from the start and that's not just the homestyle screened in front porch w/ rocking chairs! Step inside & discover a wide-open layout w/ spacious bedrooms, gleaming wood-look flooring, & abundant natural light. The primary suite

  Brandon Ford TOWER TEAM REALTY, LLC

  409 Murphy Rd, Winter Springs, FL 32708
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  /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
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  /2

  $335,000 Sold Aug 12, 2025

  • 1,386 Sq Ft
  • $242/SF
  • 62 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2007

  432 Harbor Winds Ct, Winter Springs, FL 32708

  THE WINTER SPRINGS RETREAT // Welcome to this charming ONE STORY, end-unit in the quaint gated community of Harbor Winds in Winter Springs! ***NEW ROOF PUT ON IN 2023! *** Roof Assessment fully paid off!*** This townhome offers a serene conservation view with the added privacy of no rear neighbors, along with a convenient 2-car garage and a side entry that provides a glimpse of the

  Kristina Mollo ALL REAL ESTATE & INVESTMENTS

  432 Harbor Winds Ct, Winter Springs, FL 32708
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  /4

  Est $193,712 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 945 Sq Ft

  Unlisted Address

  Unlisted Address

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