Highlands Homes

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  /58

  $110,000

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

  152 Columbus Cir, Winter Springs, FL 32708

  3 bedrooms, 2 baths-hardly lived in. Front door entrance with small porch. Very Open for entertaining. Lots of storage inside and outside. Use your imagination for decorating. Location-dead end street. Monthly fee base 41025. Located near major highways and close to shopping, restaurants and more. 55+ Community.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  152 Columbus 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

  $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
• 

  

  

  /16

  Est $173,287 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft

  415 Sheoah Blvd Unit 11, Winter Springs, FL 32708

  415 Sheoah Blvd Unit 11, Winter Springs, FL 32708
• 

  

  

  /34

  $57,900

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  382 La Vista Dr, Winter Springs, FL 32708

  NEWLY RENOVATED- 2 BEDROOM/2 BATH- 1 MONTH FREE LOT RENT!!! Totally Renovated home with new drywall, paint, & baseboards. Bathrooms have been beautifully renovated with new vanities, showers, and fixtures. Flooring and sub flooring has been installed with waterproof vinyl laminate. All new stainless-steel appliances. The A/C is a 3-new A/C mini split installed, 1 in each bedroom and 1 in the

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  382 La Vista 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

  $330,000 Sold Jul 18, 2025

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

  • 3 Beds
  • 2.5 Baths
  • Built 2007

  456 Harbor Winds Ct, Winter Springs, FL 32708

  This spacious townhome in the heart of Winter Springs has been recently upgraded and is move-in ready! Nestled in the serene gated community of Harbor Winds, this property features new appliances, a new AC, new flooring, new interior paint, and a 2023 roof. With 3 bedrooms and 2.5 bathrooms over 1,680 square feet and a backyard bordered by a lush conservation area, there is plenty of space and

  Makena Clark EXIT REALTY PREMIER LEGACY

  456 Harbor Winds Ct, Winter Springs, FL 32708
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  /26

  Est $298,649 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,088 Sq Ft

  227 Albert St, Winter Springs, FL 32708

  227 Albert St, Winter Springs, FL 32708
• 

  

  /27

  $199,900

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

  90 Moree Loop Unit 15, Winter Springs, FL 32708

  Welcome home to this beautifully updated 3-bedroom, 2- bath condo in the heart of Seminole County! This desirable FIRST- floor unit offers privacy with peaceful views - NO rear neighbors. Step inside to find brand new flooring throughout, new granite kitchen countertops, new appliances, new washer & drier and stylishly renovated bathrooms that give a fresh, modern feel. The spacious layout is

  Lynnette Mentlick FLORIDA REALTY INVESTMENTS

  90 Moree Loop Unit 15, 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

  $750,000 Sold Jul 15, 2025

  • 2,852 Sq Ft
  • $263/SF
  • 10 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2016

  672 Seven Oaks Blvd, Winter Springs, FL 32708

  Welcome to the Seven Oaks Community, where this lakefront pool home offers the perfect blend of luxury, comfort, and Florida lifestyle! Nestled on a spacious lot with peaceful views of Boat Lake, this beautifully maintained home is designed for everyday living and creating unforgettable memories. When you arrive, you will be impressed by the mature landscaping and curb appeal. Step inside to find

  Carla Trine MAINFRAME REAL ESTATE

  672 Seven Oaks Blvd, Winter Springs, FL 32708
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  /28

  Est $290,411 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,198 Sq Ft

  304 Wade St, Winter Springs, FL 32708

  304 Wade St, Winter Springs, FL 32708
• 

  

  /21

  $31,999

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

  42 La Vista Dr, Winter Springs, FL 32708

  MOTIVATED SELLER!!! willing to accept offers!! If you've been waiting for the perfect investment in a thriving, active 55+ community, this is it! 42 La Vista Drive offers 2 bedrooms, 2 baths, and a prime location on a quiet street with a babbling creek right behind the home. Big-ticket upgrades are already in place: NEW roof (2025) with 3-year transferable warranty, AC (2023), refrigerator

  Veronica Zerpa Partners Dealership LLC

  42 La Vista Dr, Winter Springs, FL 32708
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  /8

  $1,295 per month

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

  181 Garden Dr, Winter Springs, FL 32708

  181 Garden Dr. Winter Springs - Two story townhouse with two bedroom 1 1/2 bath, all bedrooms upstairs. Large back & Front yard. Minutes away from 17-92 and SR 417.

  Courtney Davis ABSOLUTE REALTY GROUP, LLC

  181 Garden Dr, Winter Springs, FL 32708
• 

  /2

  $282,000 Sold Jul 09, 2025

  • 1,248 Sq Ft
  • $226/SF
  • 12 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1985

  722 Ridgewood Way, Winter Springs, FL 32708

  Welcome home to 722 Ridgewood Way, a delightful townhouse nestled in the heart of Winter Springs, FL in the desirable community of Wildwood.Spanning 1,248 square feet, this detached townhouse lives like a single family home featuring PVC Laminate flooring (that looks like hardwood!) throughout the main living space. Upon entering, you’ll be greeted by soaring ceilings and large picture

  Marcie Gumieny COMPASS FLORIDA LLC

  722 Ridgewood Way, Winter Springs, FL 32708
• 

  

  /19

  Est $337,330 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,219 Sq Ft

  1193 Lake Lucerne Cir, Winter Springs, FL 32708

  1193 Lake Lucerne Cir, Winter Springs, FL 32708
• 

  

  /22

  $64,800

  • 2 Beds
  • 2 Baths

  338 Casa Grande Dr, Winter Springs, FL 32708

  Welcome to your ideal Florida retreat! This beautifully updated 2-bedroom, 2-bath home is nestled in a highly sought-after 55+ community in Winter Springs, just minutes from shopping, dining, and entertainment. Step inside to find luxury plank flooring throughout and a fully remodeled kitchen-perfect for cooking and entertaining. The semi-furnished interior offers both comfort and convenience,

  Gabriel Dumeng AMAZING MOBILE HOMES LLC

  338 Casa Grande Dr, Winter Springs, FL 32708
• 

  

  /16

  $1,795 per month

  • 3 Beds
  • 2 Baths
  • 1,187 Sq Ft
  • House for Rent

  506 San Gabriel Ct, Winter Springs, FL 32708

  Move In Special! Receive $250 OFF your first month of rent if approved and moving in by February 23rd!Welcome home to 506 San Gabriel Court, a charming 3 bedroom, 2 bath home featuring 1,187 square feet of living space. As you enter the home, you are welcomed into the main living area, featuring vaulted ceilings and plenty of natural light through the numerous windows and sliding glass

  Justin Recca INNOVATIVE REALTY, LLC

  506 San Gabriel Ct, Winter Springs, FL 32708
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  /2

  $425,000 Sold Jul 07, 2025

  • 1,617 Sq Ft
  • $263/SF
  • 11 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  316 Dornoch Ct, Winter Springs, FL 32708

  Tucked away on a cul-de-sac along a picturesque, tree-lined street and backed by peaceful conservation, this beautifully remodeled home blends style, comfort, and thoughtful accessibility ... all at an affordable price. Completely updated with high-quality finishes and a designer’s eye, it features soaring knockdown ceilings, abundant natural light, and seamless hard-surface flooring (tile and

  Allison Day RE/MAX TOWN & COUNTRY REALTY

  316 Dornoch Ct, Winter Springs, FL 32708
• 

  

  /26

  Est $267,248 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,434 Sq Ft

  535 Moree Loop, Winter Springs, FL 32708

  535 Moree Loop, Winter Springs, FL 32708
• 

  

  /34

  $310,000

  • 4 Beds
  • 2 Baths
  • 1,322 Sq Ft

  551 Laurel Ct Unit 3, Winter Springs, FL 32708

  Priced well below recent appraisal! Investor special in the sought-after Highlands of Winter Springs! This home is in a desirable community of Winter Springs. Sitting on a large cul-de-sac lot, this property needs some TLC, but offers strong flip or rental potential. Features a split floor plan, open living/dining area, and access to community amenities including pool, tennis, and walking

  Miraya Lane KELLER WILLIAMS ADVANTAGE III

  551 Laurel Ct Unit 3, Winter Springs, FL 32708
• 

  

  /16

  $1,695 per month

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Townhouse for Rent

  208 Perth Ct Unit B, Winter Springs, FL 32708

  Highlights: 2 Car Garage | Spacious Backyard | Serene Patio | Community Pool | Nature Trails | BBQ Area Grills | Tennis Court | Community Playground | Picnic Area |Discover the vibrant charm of Winter Springs, nestled by the serene Lake Jesup and offering upscale living, diverse dining options, and a rich cultural scene. With pristine parks, top-notch schools, and annual festivities like

  Amy Johnston BELMONT REALTY

  208 Perth Ct Unit B, Winter Springs, FL 32708
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  /2

  $289,000 Sold Jul 07, 2025

  • 1,105 Sq Ft
  • $262/SF
  • 120 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1994

  203 San Gabriel St, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available at closing.Welcome to this charming property, where elegance meets simplicity. The home features a neutral color paint scheme that gives it a serene and calming ambiance. A newly painted interior provides a fresh and clean living environment. The highlight of this property is the beautiful patio, perfect for

  Karen Albright OPENDOOR BROKERAGE LLC

  203 San Gabriel St, Winter Springs, FL 32708
• 

  

  /26

  Est $390,598 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,757 Sq Ft

  410 Macgregor Rd, Winter Springs, FL 32708

  410 Macgregor Rd, Winter Springs, FL 32708
• 

  

  /36

  $480,000

  • 3 Beds
  • 2.5 Baths
  • 2,185 Sq Ft

  821 Sheoah Cir, Winter Springs, FL 32708

  Exceptional two-story home in the sought-after Highlands of Winter Springs, a community surrounded by scenic nature trails and lush green spaces. Located within walking distance to top-rated Seminole County schools, with shopping, dining, and major roadways just minutes away. Situated on a premium conservation lot with no rear neighbors, this 3-bedroom, 2.5-bath residence offers nearly 2,200 sq.

  Sean Calegan CFRP REALTY LLC

  821 Sheoah Cir, Winter Springs, FL 32708
• 

  /2

  $388,000 Sold Jul 02, 2025

  • 2,176 Sq Ft
  • $178/SF
  • 270 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2008

  400 Harbor Winds Ct, Winter Springs, FL 32708

  Welcome to this fabulous 2-story, 3 bedroom, 3 full bath, end unit townhouse with attached 2-car garage, in a cul-de-sac, in the exclusive gated community of Harbor Winds. You can enjoy being in a premium unit that backs up to a wooded view for peace and relaxation. Inside, the perfectly upgraded kitchen includes a cozy breakfast nook, granite counters, stainless steel appliances, custom

  Anderson (Luis) Zamora OLYMPUS EXECUTIVE REALTY INC

  400 Harbor Winds Ct, Winter Springs, FL 32708
• 

  

  /33

  Est $143,215 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 710 Sq Ft

  210 Moree Loop Unit 7, Winter Springs, FL 32708

  210 Moree Loop Unit 7, 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
• 

  /2

  $270,000 Sold Jun 30, 2025

  • 1,166 Sq Ft
  • $232/SF
  • 357 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1971

  101 Albert St, Winter Springs, FL 32708

  Just Reduce!!!! Location, location, location!!! Fantastic opportunity to own this Single Family house 3/2 one car garage with fence and storage attached to the property. This property has tile floor throughout the house. NO HOA, NO CDD, Roof was replaced 4 years ago. This property is in an excellent location near a major highway, airport, shopping center and more. If you want to have easy access

  Rosalina Martinez LA ROSA REALTY LLC

  101 Albert St, Winter Springs, FL 32708
• 

  

  /26

  Est $305,788 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,370 Sq Ft

  209 Bennett St, Winter Springs, FL 32708

  209 Bennett St, Winter Springs, FL 32708
• 

  

  /16

  $169,900

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  130 Columbus Cir, Winter Springs, FL 32708

  Looking for your dream home? This stunning 3-bedroom, 2-bathroom property is ready for you! From the moment you arrive, you'll appreciate the curb appeal, with a generous 3-car driveway and a 1-car garage. Step inside and discover an open-concept living space with vaulted ceilings, modern light fixtures, and a walk-in food pantry for all your storage needs. The kitchen is a chef's delight,

  Gabriel Dumeng AMAZING MOBILE HOMES LLC

  130 Columbus Cir, Winter Springs, FL 32708
• 

  /2

  $343,000 Sold Jun 26, 2025

  • 1,284 Sq Ft
  • $267/SF
  • 25 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  50 S Devon Ave, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. Welcome to this fully renovated 3-bedroom, 2-bathroom home located in the heart of Winter Springs! Offering a spacious and functional layout, this beautiful property features a living room, dining room, Florida room, kitchen, and indoor laundry area—all thoughtfully updated for modern living.Enjoy peace of mind with brand-new upgrades,

  Katherine Fernandez De Los Santos LPT REALTY, LLC

  50 S Devon Ave, Winter Springs, FL 32708
• 

  

  /32

  Est $248,640 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 961 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /23

  $339,900

  • 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
• 

  /2

  $215,000 Sold Jun 20, 2025

  • 898 Sq Ft
  • $239/SF
  • 30 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  120 Rhoden Ln, Winter Springs, FL 32708

  Looking to downsize, maybe your first home or investment property? This 2 bedroom, 1 1/2 bath home is the perfect one for you! Two front parking spaces also come with the unit. HVAC 2021 and Roof 2017. TILE FLOORS throughout the downstairs including the half bath. The kitchen features a dining area, breakfast bar and sliding doors to the SCREENED back porch with backyard space. Upstairs you

  Heather Pryor KELLER WILLIAMS ADVANTAGE REALTY

  120 Rhoden Ln, Winter Springs, FL 32708
• 

  

  /24

  Est $332,664 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,268 Sq Ft

  648 Elmwood Dr, Winter Springs, FL 32708

  648 Elmwood Dr, Winter Springs, FL 32708
• 

  

  /23

  $337,500

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  391 Panama Cir, Winter Springs, FL 32708

  Welcome to 391 Panama Circle:This move-in ready 3 bedroom, 2 bath residence features fresh interior paint and brand new carpet and luxury vinyl laminate throughout, offering a clean and inviting atmosphere. Enjoy Florida living on the screened-in porch overlooking a private, fully fenced backyard perfect for relaxing or entertaining. Additional highlights include a spacious 2-car

  Summer Hornburg BELMONT REALTY

  391 Panama Cir, Winter Springs, FL 32708
• 

  /2

  $241,000 Sold Jun 17, 2025

  • 1,069 Sq Ft
  • $225/SF
  • 245 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1997

  409 Horizon Dr, Winter Springs, FL 32708

  Welcome to 409 Horizon Dr, Winter Springs! This 3-bedroom, 2-bathroom home in the desirable SEASONS THE community offers a bright and inviting space with thoughtful updates. Inside, you'll find laminate flooring, a freshly painted interior, and appliances including a washer and dryer, all provided for added convenience. This updated home features quartz countertops, refinished cabinets, new

  Shereen Prewett MARK SPAIN REAL ESTATE

  409 Horizon Dr, Winter Springs, FL 32708
• 

  

  /53

  Est $291,537 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  755 Forest St, Winter Springs, FL 32708

  755 Forest St, Winter Springs, FL 32708
• 

  

  /42

  $295,900

  • 4 Beds
  • 1 Bath
  • 1,120 Sq Ft

  206 Charles St, Winter Springs, FL 32708

  Price Reduced! VIEW WALKTROUGH VIDEO! Charming Bungalow that lives quite large. Discover your dream home nestled in the heart of Winter Springs, on one floor, perfect for all family types. All new neutral FRESH INTERIOR PAINT! Split plan. Great eat in kitchen and floorplan that overlooks the backyard! This enchanting single-family residence boasts four cozy bedrooms, offering a flexible split

  Laurie Cash Cain CHARLES RUTENBERG REALTY ORLANDO

  206 Charles St, Winter Springs, FL 32708

Showing Results 121 - 160, Page 4 of 18