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  1. Home
  2. /Sarasota, FL
  3. /8 - 4442 HIGHLAND PARK
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$375,000est. $1,896 MortgageInfo icon
Listed: $ 400,000 (Sold on: Feb 26, 2026) Days on Market:113

8- 4442 HIGHLAND PARK, SARASOTA, FL 34235

BEDS

beds

3

BATHS

baths

3

PARKING

parking

-

SQFT

sqft
2120

Description

Step inside this freestanding villa and instantly feel at home. With over 2,100 square feet of living space, cathedral ceilings, and a spacious great room featuring a wood-burning fireplace and built-in wet bar, this residence blends comfort, character, and the charm of The Meadows lifestyle. The flexible three-bedroom layout includes a room with double doors currently used as a den—ideal for a home office or cozy reading retreat. Freshly painted and featuring new carpet in the bedrooms, the home feels bright and inviting, while allowing the next owner the opportunity to personalize a few updates to their own taste. An enclosed sun porch offers a front-row view of the golf course, perfect for morning coffee or evening sunsets. The courtyard-style entry and attached two-car garage provide easy access and a sense of privacy, while the large primary suite offers a peaceful haven with generous space and a tranquil view. Highland Park is an intimate enclave of just 20 villas, offering a community pool and panoramic views of gardens and golf course greens. The Meadows features miles of walking and biking trails, an active community center, and a full social calendar—all within minutes of Nathan Benderson Park, local shopping, dining, and a short drive to downtown Sarasota and the beaches. 4442 Highland Park is more than a home—it’s an invitation to live surrounded by beauty, convenience, and a welcoming community.

Description

Step inside this freestanding villa and instantly feel at home. With over 2,100 square feet of living space, cathedral ceilings, and a spacious great room featuring a wood-burning fireplace and built-in wet bar, this residence blends comfort, character, and the charm of The Meadows lifestyle. The flexible three-bedroom layout includes a room with double doors currently used as a den—ideal for a home office or cozy reading retreat. Freshly painted and featuring new carpet in the bedrooms, the home feels bright and inviting, while allowing the next owner the opportunity to personalize a few updates to their own taste. An enclosed sun porch offers a front-row view of the golf course, perfect for morning coffee or evening sunsets. The courtyard-style entry and attached two-car garage provide easy access and a sense of privacy, while the large primary suite offers a peaceful haven with generous space and a tranquil view. Highland Park is an intimate enclave of just 20 villas, offering a community pool and panoramic views of gardens and golf course greens. The Meadows features miles of walking and biking trails, an active community center, and a full social calendar—all within minutes of Nathan Benderson Park, local shopping, dining, and a short drive to downtown Sarasota and the beaches. 4442 Highland Park is more than a home—it’s an invitation to live surrounded by beauty, convenience, and a welcoming community.
listing image
8 -
$375,000
est. $1,896.2 MortgageInfo icon
Listed: $ 400,000 (Sold on: Feb 26, 2026)
Days on Market:113

8 -

4442 HIGHLAND PARK #8, SARASOTA, FL 34235

BEDS

3

BATHS

3

PARKING

-

SQFT

2,120

Description

Step inside this freestanding villa and instantly feel at home. With over 2,100 square feet of living space, cathedral ceilings, and a spacious great room featuring a wood-burning fireplace and built-in wet bar, this residence blends comfort, character, and the charm of The Meadows lifestyle. The flexible three-bedroom layout includes a room with double doors currently used as a den—ideal for a home office or cozy reading retreat. Freshly painted and featuring new carpet in the bedrooms, the home feels bright and inviting, while allowing the next owner the opportunity to personalize a few updates to their own taste. An enclosed sun porch offers a front-row view of the golf course, perfect for morning coffee or evening sunsets. The courtyard-style entry and attached two-car garage provide easy access and a sense of privacy, while the large primary suite offers a peaceful haven with generous space and a tranquil view. Highland Park is an intimate enclave of just 20 villas, offering a community pool and panoramic views of gardens and golf course greens. The Meadows features miles of walking and biking trails, an active community center, and a full social calendar—all within minutes of Nathan Benderson Park, local shopping, dining, and a short drive to downtown Sarasota and the beaches. 4442 Highland Park is more than a home—it’s an invitation to live surrounded by beauty, convenience, and a welcoming community.

Description

Step inside this freestanding villa and instantly feel at home. With over 2,100 square feet of living space, cathedral ceilings, and a spacious great room featuring a wood-burning fireplace and built-in wet bar, this residence blends comfort, character, and the charm of The Meadows lifestyle. The flexible three-bedroom layout includes a room with double doors currently used as a den—ideal for a home office or cozy reading retreat. Freshly painted and featuring new carpet in the bedrooms, the home feels bright and inviting, while allowing the next owner the opportunity to personalize a few updates to their own taste. An enclosed sun porch offers a front-row view of the golf course, perfect for morning coffee or evening sunsets. The courtyard-style entry and attached two-car garage provide easy access and a sense of privacy, while the large primary suite offers a peaceful haven with generous space and a tranquil view. Highland Park is an intimate enclave of just 20 villas, offering a community pool and panoramic views of gardens and golf course greens. The Meadows features miles of walking and biking trails, an active community center, and a full social calendar—all within minutes of Nathan Benderson Park, local shopping, dining, and a short drive to downtown Sarasota and the beaches. 4442 Highland Park is more than a home—it’s an invitation to live surrounded by beauty, convenience, and a welcoming community.

Glen Gardens Estate Market Stats Last 12 months

LOCKER
Contact Us for Info

POSSESSION
Contact Us for Info
HOA FEESinfo
$2,049 /Annually

OUTDOOR SPACE
Courtyard
TAXES
$3,127 (2025)

BUILDING AGE
38 Years
BASEMENT FEATURE
Contact Us for Info

PRICE PER SQFTinfo
$177

Market Stats

HOA FEESinfo
$2,049 /Annually

OUTDOOR SPACE
Courtyard
TAXES
$3,127 (2025)

BUILDING AGE
38 Years
BASEMENT FEATURE
Contact Us for Info

PRICE PER SQFTinfo
$177

Amenities

Parking
Parking
-
Locker
Locker
Concierge
Concierge
-
Elevator(s)
Elevator(s)
-
Central AC
Central AC
Check Icon
Pool
Pool
Check Icon
Fitness Center
Fitness Center
-
Visitors Parking
Visitors Parking
-

Amenities

Unit
Parking GarageParking Garage
Building

Policies

Pet Allowed
Check
Pet Allowed Info icon
Check Icon
BBQ Permitted
BBQ Permitted
Sublet Allowed
Sublet Allowed
Short-term Rental Allowed
Short-term Rental Allowed

Unit Price History

DateMLSStatusPrice
Feb 2026MLS#: A4670881Closed$320,000

Unit Price History

$320,000

Closed

Feb 2026MLS#: A4670881

Monthly Payment Calculator

$4,262 / Monthly

All calculations are estimates and provided by HelloCondo.com
for informational purposes only. Actual amounts may vary.

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$4,262
Est.
Listing Price
Down Payment
Interest Rate
Terms
Listing Price
Down Payment
Interest Rate
Terms

Monthly Payment Calculator

$4,262
Est.
Listing Price
Down Payment
Interest Rate
Terms
Listing Price
Down Payment
Interest Rate
Terms
$4,262 / Monthly

All calculations are estimates and provided by HelloCondo.com for informational purposes only. Actual amounts may vary.

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Monthly Mortgage: $1,896
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The Neighborhood: SARASOTA, FL

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  1. Home
  2. /Sarasota, FL
  3. /8 - 4442 HIGHLAND PARK
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