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102 SETTLERS CIRCLE, WINCHESTER, VA, 22602

$499,900

3 beds
2 full baths
1 half baths
2,268 sq. ft

102 SETTLERS CIRCLE, WINCHESTER, VA, 22602
$499,900 Active JUST LISTED

Beds 3
Baths 2.5
Sq. ft 2,268

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Active JUST LISTED

This classic Colonial home, ideally situated in a desirable Winchester neighborhood, offers 3 spacious bedrooms and 2.5 baths. Rich in charm, this home boasts a traditional layout with over 3300 sq feet on 3 levels. There is a Bonus room that would be perfect for use as a 4th bedroom, home office, or guest space. Improvements include a Brand new architectural shingle roof, newer water heater, and a well maintained dually zoned HVAC system with a new condenser unit. You will LOVE the Gleaming wood floors throughout the main level! Bathrooms are updated with luxury vinyl plank and tile flooring. The Kitchen is elegant with vintage style cabinetry, granite countertops, gas stove cooking, a roomy pantry, and an island, all overlooking the large landscaped backyard. A great place to entertain, the rear outdoor space has a stunning patio with a cozy pergola, relaxing water fountains, and a warm fire pit area to gather around. Not to mention the Fully fenced rear has lots of majestic trees for a feeling of privacy and peace. The Unnfinished basement has a rough-in and it's just waiting for your dream project! This location has effortless access to vibrant downtown, with a variety of restaurants, entertainment, and cultural attractions! Ideal location for commuters! A Must See Schedule a Showing Today!

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Property Features

Year Built:
1996

Days on Market:
2

Listing ID:
VAFV2042324

Bathrooms:
2 full , 1 half

List Date:
June 12, 2026

Property Type:
Single Family Residential

Architecture Style:
Colonial

Subdivision:
PIONEER HEIGHTS

County:
FREDERICK

Appliances:

Total Taxes:
$1,847

Courtesy of ERA Oakcrest Realty, Inc.

This content was last updated on June 13, 2026 16:53

Name	Type	Level	Grades	Address
Millbrook High School	Public	High	9-12	251 First Woods Dr, Winchester, VA 22603
District: Frederick County Public Schools Grade Span: 9 - 12 Admission: Public Address: 251 First Woods Dr, Winchester, VA 22603 Phone: 540-545-2800 Website: http://www.frederickcountyschoolsva.net/ Teachers: 99 Students: 1550 Ratio: 16:1 Students/Teacher Gender: 50% Male / 50% Female Lunch: 42% Free / 5% Reduced Student/Teacher ratio Enrollment
James Wood Middle School	Public	Middle	6-8	1313 Amherst St, Winchester, VA 22601
District: Frederick County Public Schools Grade Span: 6 - 8 Admission: Public Address: 1313 Amherst St, Winchester, VA 22601 Phone: 540-667-7500 Website: http://www.frederickcountyschoolsva.net/ Teachers: 69 Students: 873 Ratio: 13:1 Students/Teacher Gender: 52% Male / 48% Female Lunch: 70% Free Student/Teacher ratio Enrollment
Redbud Run Elementary School	Public	Primary	PK-5	250 First Woods Dr, Winchester, VA 22603
District: Frederick County Public Schools Grade Span: PK - 5 Admission: Public Address: 250 First Woods Dr, Winchester, VA 22603 Phone: 540-678-1868 Website: http://www.frederickcountyschoolsva.net/ Teachers: 44 Students: 614 Ratio: 14:1 Students/Teacher Gender: 52% Male / 48% Female Lunch: 73% Free Student/Teacher ratio Enrollment

Name	Type	Level	Grades	Address
Grafton Integrated Health Network - Winchester	Private	Combined Elementary/Secondary	2-12	120 Bellview Ave, Winchester, VA 22601
Grade Span: 2 - 12 Admission: Private Address: 120 Bellview Ave, Winchester, VA 22601 Phone: 540-542-0200 Teachers: 11 Students: 71 Ratio: 6:1 Students/Teacher Gender: 86% Male / 14% Female Student/Teacher ratio Enrollment
Grafton-Ruth Birch Campus	Private	Combined Elementary/Secondary	2-12	120 Bellview Ave, Winchester, VA 22601
Grade Span: 2 - 12 Admission: Private Address: 120 Bellview Ave, Winchester, VA 22601 Phone: 540-542-0200 Teachers: 11 Students: 71 Ratio: 6:1 Students/Teacher Gender: 86% Male / 14% Female Student/Teacher ratio Enrollment
Lighthouse Baptist Academy	Private	Combined Elementary/Secondary	PK-12	2581 Northwestern Pike, Winchester, VA 22603
Grade Span: PK - 12 Admission: Private Address: 2581 Northwestern Pike, Winchester, VA 22603 Phone: 540-662-5590 Teachers: 9 Students: 97 Ratio: 11:1 Students/Teacher Gender: 48% Male / 52% Female Student/Teacher ratio Enrollment
Mountain View Christian Academy	Private	Combined Elementary/Secondary	KG-12	153 Narrow Ln, Winchester, VA 22602
Grade Span: KG - 12 Admission: Private Address: 153 Narrow Ln, Winchester, VA 22602 Phone: 540-868-1231 Website: http://www.ccmv.com/ Teachers: 20 Students: 184 Ratio: 9:1 Students/Teacher Gender: 51% Male / 49% Female Student/Teacher ratio Enrollment
Sacred Heart Academy	Private	Elementary	PK-8	110 Keating Dr, Winchester, VA 22601
Grade Span: PK - 8 Admission: Private Address: 110 Keating Dr, Winchester, VA 22601 Phone: 732-261-7103 Website: http://www.sacredheartva.org/ Teachers: 24 Students: 246 Ratio: 10:1 Students/Teacher Gender: 48% Male / 52% Female Student/Teacher ratio Enrollment
The Independent School of Winchester Inc	Private	Combined Elementary/Secondary	KG-12	769 Round Hill Rd, Winchester, VA 22602
Grade Span: KG - 12 Admission: Private Address: 769 Round Hill Rd, Winchester, VA 22602 Phone: 540-877-5552 Teachers: 10 Students: 52 Ratio: 5:1 Students/Teacher Gender: 48% Male / 52% Female Student/Teacher ratio Enrollment
The School at Sharon's	Private	Elementary	PK-KG	1855 Senseny Rd, Winchester, VA 22602
Grade Span: PK - KG Admission: Private Address: 1855 Senseny Rd, Winchester, VA 22602 Phone: 540-667-6200 Teachers: 1 Students: 6 Ratio: 6:1 Students/Teacher Gender: 100% Male Student/Teacher ratio Enrollment
Winchester Montessori School	Private	Elementary	KG-5	1090 W Parkins Mill Rd, Winchester, VA 22602
Grade Span: KG - 5 Admission: Private Address: 1090 W Parkins Mill Rd, Winchester, VA 22602 Phone: 540-667-1184 Website: http://www.winchestermontessori.com/ Teachers: 3 Students: 24 Ratio: 8:1 Students/Teacher Gender: 46% Male / 54% Female Student/Teacher ratio Enrollment

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102 SETTLERS CIRCLE, WINCHESTER, VA, 22602

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102 SETTLERS CIRCLE, WINCHESTER, VA, 22602
$499,900 Active JUST LISTED

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Student/Teacher ratio

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Student/Teacher ratio

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Student/Teacher ratio

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Student/Teacher ratio

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Student/Teacher ratio

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Student/Teacher ratio

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Student/Teacher ratio

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Student/Teacher ratio

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Student/Teacher ratio

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Student/Teacher ratio

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Buying a Home

Selling a Home

Relocating with New Millennium

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Careers at New Millennium

102 SETTLERS CIRCLE, WINCHESTER, VA, 22602

$499,900

102 SETTLERS CIRCLE, WINCHESTER, VA, 22602$499,900 Active JUST LISTED

Request More Information

Schools

Student/Teacher ratio

Enrollment

Student/Teacher ratio

Enrollment

Student/Teacher ratio

Enrollment

Student/Teacher ratio

Enrollment

Student/Teacher ratio

Enrollment

Student/Teacher ratio

Enrollment

Student/Teacher ratio

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Student/Teacher ratio

Enrollment

Student/Teacher ratio

Enrollment

Student/Teacher ratio

Enrollment

Student/Teacher ratio

Enrollment

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102 SETTLERS CIRCLE, WINCHESTER, VA, 22602
$499,900 Active JUST LISTED