Single Story homes for sale & real estate in Winter Park Pines, FL

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2819 Scarlet Rd, Winter Park, FL 32792
2819 Scarlet Rd, Winter Park, FL 32792
2819 Scarlet Rd, Winter Park, FL 32792
ABOUT THIS HOME
Single Story Home for sale in Winter Park Pines, FL:
Welcome to Winter Park Pines, a community known for its tree-lined streets, friendly neighbors, and the rare charm of front-door mail delivery! This spacious 2,000+ sq. ft. home presents an incredible opportunity to invest in a neighborhood where property values are soaring. Nestled on a picturesque street, this home boasts fantastic curb appeal and a lush, private backyard oasis—perfect for outdoor gatherings or quiet relaxation. The low-maintenance landscaping ensures you have more time to enjoy your surroundings. Step inside to discover a well-structured layout with tremendous potential. While some updating may be desired, the home offers solid bones and ample space to bring your v

$515,000

3 beds2 baths2,197 sq ft

2819 Scarlet Rd, Winter Park, FL 32792

7,994 sq ft lot • 2 garage spots • Community pool

715 Roughbeard Rd, Winter Park, FL 32792
715 Roughbeard Rd, Winter Park, FL 32792
715 Roughbeard Rd, Winter Park, FL 32792
ABOUT THIS HOME
Single Story Home for sale in Winter Park Pines, FL:
Have you been looking for a home that you can update and make it your own? This home is the perfect opportunity to live in the coveted neighborhood of WINTER PARK PINES. This four bedroom, two bath POOL home is a well-built traditional home waiting for its next owner. The ROOF was replaced in 2024 and the remaining home is waiting for your personal touch. The oversize Florida room has nearly 400 sq ft to transform into additional living area or expand the kitchen, the options are limitless. This quaint home is less than 1 mile from WINTER PARK HIGH SCHOOL, less than 4 miles to PARK AVE AND ROLLINS COLLEGE, as well as under 10 miles from the Orlando Airport. Come take a look today. No offer

$575,000

4 beds2 baths2,250 sq ft

715 Roughbeard Rd, Winter Park, FL 32792

0.25 acre lot • 2 garage spots • Pool

236 N Ranger Blvd, Winter Park, FL 32792
236 N Ranger Blvd, Winter Park, FL 32792
236 N Ranger Blvd, Winter Park, FL 32792
ABOUT THIS HOME
Single Story Home for sale in Winter Park Pines, FL:
One or more photo(s) has been virtually staged. FULLY Renovated – This beautiful quarter acre Medallion Home offers 3 spacious bedrooms and 2 full bathrooms, with a bright open-concept layout and an inviting Florida room that overlooks a private, tree-lined backyard—perfect for family gatherings, peaceful mornings, or relaxed evenings at home. Your home gives you the opportunity to have access to an A-rated school district in a highly sought-after Winter Park community—a community that delivers the feel of an upscale HOA, WITHOUT THE FEES. Here, you can enjoy the convenience of one of the area’s premier 18-hole golf courses, a 2.5-mile scenic nature trail ideal for b

$649,900

3 beds2 baths1,844 sq ft

236 N Ranger Blvd, Winter Park, FL 32792

9,294 sq ft lot • 2 garage spots • Community pool

2817 Prince John Rd, Winter Park, FL 32792
2817 Prince John Rd, Winter Park, FL 32792
2817 Prince John Rd, Winter Park, FL 32792
ABOUT THIS HOME
Single Story Home for sale in Winter Park Pines, FL:
NEW ROOF 2019! GREAT PRICE! SPECTACULAR WINTER PARK HOME COMPLETELY RENOVATED AND UPGRADED INCLUDING A STUNNING KITCHEN! This four bedroom three and a half bath home has been meticulously updated and cared for! It has PORCELAIN WOOD LOOK TILE and WOOD flooring THROUGHOUT and NO CARPET. When you walk in the front door you are greeted by a grand and open design. This one-story home even has an IN LAW SUITE with its own private bathroom. When you walk up to the home you are greeted by the inviting front porch. Once entering the home you will find custom details such as crown molding, stunning countertops that look like artwork and much more! From the kitchen, family room, living room and dinin

$674,900

4 beds3.5 baths2,183 sq ft

2817 Prince John Rd, Winter Park, FL 32792

8,135 sq ft lot • 2 garage spots

2855 Lion Heart Rd, Winter Park, FL 32792
2855 Lion Heart Rd, Winter Park, FL 32792
2855 Lion Heart Rd, Winter Park, FL 32792
ABOUT THIS HOME
Single Story Home for sale in Winter Park Pines, FL:
Welcome to 2855 Lion Heart Dr, Winter Park — a beautifully remodeled home that seamlessly combines modern comfort with an unbeatable location. This move-in ready residence features a brand-new kitchen with smart stainless steel appliances, completely updated bathrooms, new luxury flooring throughout, and an open-concept layout perfect for entertaining. Major upgrades include a new roof (2025) and new water heater. Situated just minutes from Winter Park Pines Golf Course, Cady Way Trail, tennis and pickleball courts, community pool, parks, shopping, and Winter Park Hospital, it’s also conveniently close to Rollins College and Full Sail University. Located on a quiet, tree-lined s

$640,000

3 beds2 baths1,727 sq ft

2855 Lion Heart Rd, Winter Park, FL 32792

8,866 sq ft lot • 2 garage spots • Pool

Property at 2823 Cady Way, Winter Park, FL 32792, 4 beds, 2 baths

$498,000

4 beds2 baths1,688 sq ft

2823 Cady Way, Winter Park, FL 32792

Property at 274 N Ranger Blvd, Winter Park, FL 32792, 3 beds, 2 baths

$580,000

3 beds2 baths1,420 sq ft

274 N Ranger Blvd, Winter Park, FL 32792

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417 Carvell Dr, Winter Park, FL 32792
417 Carvell Dr, Winter Park, FL 32792
417 Carvell Dr, Winter Park, FL 32792
ABOUT THIS HOME
Single Story Home for sale in Winter Park Pines, FL:
Welcome to 417 Carvell Drive—where timeless mid-century modern design meets contemporary comfort. This beautifully updated 4-bedroom, 3-bathroom home sits on a spacious quarter-acre fenced lot in the heart of Winter Park. Thoughtfully designed with a split floor plan, the home features two primary bedrooms, ideal for multi-generational living or guest privacy. One of the suites includes a newly renovated bathroom with elegant modern finishes. The open layout, paired with large windows, fills the home with natural light, creating a warm, inviting atmosphere. The updated kitchen boasts granite countertops, wood cabinetry, and stainless steel appliances, offering both style and functiona

$485,000

4 beds3 baths1,823 sq ft

417 Carvell Dr, Winter Park, FL 32792

0.25 acre lot

194 Scottsdale Sq #194, Winter Park, FL 32792
194 Scottsdale Sq #194, Winter Park, FL 32792
194 Scottsdale Sq #194, Winter Park, FL 32792
ABOUT THIS HOME
Single Story Home for sale in Winter Park Pines, FL:
$1K Closing Cost CREDIT to Buyer if closed before May 30th! Spacious 2-Bedroom Winter Park Condo – Prime Location & Incredible Potential! CONDO FEES PAID THROUGH JUNE FOR THE BUYER! Seller Financing AVAILABLE with $50k down at purchase price of $79,900. Seller will finance the balance! This 2-bedroom, 1.5-bathroom condo offers 1,085 sq. ft. of living space and is an absolute steal with endless potential! Nestled on the second floor, this unit boasts one of the best views in the community—overlooking the sparkling pool right outside the primary bedroom window. Step onto your private balcony and soak in the Florida sunshine! The rental market is thriving in this area,

$64,900

2 beds1.5 baths1,085 sq ft

194 Scottsdale Sq #194, Winter Park, FL 32792

8,509 sq ft lot • $2,800 HOA • Community pool

101 Scottsdale Sq #101, Winter Park, FL 32792
101 Scottsdale Sq #101, Winter Park, FL 32792
101 Scottsdale Sq #101, Winter Park, FL 32792
ABOUT THIS HOME
Single Story Home for sale in Winter Park Pines, FL:
Welcome to this spacious and modern 2 bedroom, 2 bathroom condominium located in Winter Park, FL, just minutes from Full Sail University, Baldwin Park, shopping, and entertainment. This property is the perfect fit for a first-time home buyer or a great rental opportunity for $1600 monthly. Huge Rental Market in this area! Upon entering the unit, you'll be greeted by an open floor plan, with a large living room. The kitchen features newer appliances and a bar top big enough for three . There is plenty of cabinet and counter space, as well as built-in storage. The master bedroom features an ensuite bathroom. The second bedroom is well-sized and adjacent to the second full bathroom. Both bathr

$100,000

2 beds2 baths1,020 sq ft

101 Scottsdale Sq #101, Winter Park, FL 32792

8,617 sq ft lot • $2,683 HOA • Community pool

2936 Antique Oaks Cir #71, Winter Park, FL 32792
2936 Antique Oaks Cir #71, Winter Park, FL 32792
2936 Antique Oaks Cir #71, Winter Park, FL 32792
ABOUT THIS HOME
Single Story Home for sale in Winter Park Pines, FL:
Welcome to this inviting first-floor condo, designed with an open concept floor plan that seamlessly blends comfort and style. The expansive family room provides a generous space for family gatherings and entertaining, with abundant natural light flowing through large windows and a screened-in porch. This condo features two generously sized bedrooms and two full bathrooms, offering ample space and privacy. The master bedroom includes an en-suite bathroom for added convenience and comfort. The well-appointed kitchen is a chef’s delight, boasting granite countertops and stainless steel appliances, including a full-sized refrigerator, stove, oven, and microwave. Additional cabinet space

$195,000

2 beds2 baths1,018 sq ft

2936 Antique Oaks Cir #71, Winter Park, FL 32792

4,228 sq ft lot • $407 HOA • Community pool

110 Scottsdale Sq #110, Winter Park, FL 32792
110 Scottsdale Sq #110, Winter Park, FL 32792
110 Scottsdale Sq #110, Winter Park, FL 32792
ABOUT THIS HOME
Single Story Home for sale in Winter Park Pines, FL:
Attention!!! Just Reduced!!! Charming & Updated Condo in the Heart of Winter Park! Welcome to your perfect retreat in Winter Park, Florida! This beautifully renovated 2-bedroom, 1.5-bathroom condo offers the ideal combination of modern style, comfort, and convenience. Located on the second floor in a peaceful community, this move-in-ready gem is perfect for homeowners and investors alike! Stylishly updated interiors with modern finishes, Bright & airy layout with plenty of natural light, Spacious bedrooms and a well-appointed kitchen, Private balcony—perfect for morning coffee or unwinding after a long day, Resort-style pool—soak up the Florida sunshine, Tennis court

$149,900

2 beds1.5 baths1,085 sq ft

110 Scottsdale Sq #110, Winter Park, FL 32792

8,617 sq ft lot • $2,841 HOA • Community pool

2923 Antique Oaks Cir #39, Winter Park, FL 32792
2923 Antique Oaks Cir #39, Winter Park, FL 32792
2923 Antique Oaks Cir #39, Winter Park, FL 32792
ABOUT THIS HOME
Single Story Home for sale in Winter Park Pines, FL:
Condo in Winter Park, FL Welcome to 2923 Antique Oaks Cir, Unit 39 — a beautifully updated 1,105 sq. ft. first-floor condo offering 2 bedrooms, 2 bathrooms, and modern upgrades throughout. Located in the highly sought-after Winter Park School District, this property combines comfort, style, and convenience. Property Highlights: Size & Layout: Spacious 1,105 square feet with a thoughtfully designed floor plan. Updated Interiors: Recently remodeled with modern finishes, including appliances (convection oven, refrigerator, dishwasher), and washer/dryer in the interior laundry room. Outdoor Living: Relax on your private screened patio, perfect for morning coffee or evening unwindi

$229,900

2 beds2 baths1,105 sq ft

2923 Antique Oaks Cir #39, Winter Park, FL 32792

4,547 sq ft lot • $442 HOA • Community pool

Property at 166 Scottsdale Sq #166, Winter Park, FL 32792, 2 beds, 2 baths

$100,000

2 beds2 baths1,020 sq ft

166 Scottsdale Sq #166, Winter Park, FL 32792

Property at 2935 Antique Oaks Cir #64, Winter Park, FL 32792, 2 beds, 2 baths

$218,000

2 beds2 baths1,018 sq ft

2935 Antique Oaks Cir #64, Winter Park, FL 32792

Property at 2924 Antique Oaks Cir #46, Winter Park, FL 32792, 2 beds, 2 baths

$210,000

2 beds2 baths1,105 sq ft

2924 Antique Oaks Cir #46, Winter Park, FL 32792

Property at 2923 Antique Oaks Cir #37, Winter Park, FL 32792, 2 beds, 2 baths

$216,462

2 beds2 baths1,105 sq ft

2923 Antique Oaks Cir #37, Winter Park, FL 32792

Property at 3038 Antique Oaks Cir #166, Winter Park, FL 32792, 2 beds, 2 baths

$225,000

2 beds2 baths1,018 sq ft

3038 Antique Oaks Cir #166, Winter Park, FL 32792

Property at 2907 Summerfield Rd, Winter Park, FL 32792, 5 beds, 2 baths

$749,000

5 beds2 baths2,532 sq ft

2907 Summerfield Rd, Winter Park, FL 32792

Based on information submitted to the MLS GRID as of Thu May 22 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Single Story Homes for Sale in Winter Park Pines

There are currently 7 single story homes for sale in Winter Park Pines at a median listing price of $625K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winter Park Pines stay on the market for 18 days and receive 3 offers. Popular neighborhoods include Audubon Park, Virginia Heights, Winter Park Downtown Historic District, Windsong, and Baldwin Park. This map is refreshed with the newest listings in Winter Park Pines every 15 minutes.

In the past month, 5 homes have been sold in Winter Park Pines. In addition to houses in Winter Park Pines, there was also 1 condo, 0 townhouses, and 0 multi-family units for sale in Winter Park Pines last month. Find your dream home in Winter Park Pines using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winter Park Pines are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winter Park Pines. If you're looking to sell your home in the Winter Park Pines area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winter Park Pines with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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