Gated Communities in Leesburg, FL

By Jon Brooks, Co-Founder, Momentum Realty · Updated June 16, 2026

Looking for gated communities in Leesburg, FL? Momentum tracks 62 Leesburg communities with evidence of gated community living, each with MLS-derived pricing and market pace below — plus the local questions worth asking before you buy, and a direct line to an agent who works these communities.

Leesburg gated communities at a glance

The communities, by recent sales activity

Communities are listed by recent closing volume in Momentum’s MLS data. Figures are aggregates, change over time, and are deemed reliable but not guaranteed.

Every other tracked gated communities in Leesburg

• PLANTATION AT LEESBURG HERON RUN
• PLANTATION AT LEESBURG SABLE RIDGE VILLAGE L
• ROYAL HLNDS PH I-D
• PLANTATION AT LEESBURG RIVERSIDE VILLAGE LT
• PLANTATION AT LEESBURG MAGNOLIA POINT
• LEESBURG ROYAL OAK ESTATES SUB
• PLANTATION AT LEESBURG LONG MEADOW VILLAGE
• PLANTATION AT LEESBURG CHANTICLEER VILLAGE L
• PLANTATION AT LEESBURG ROSEDOWN VILLAGE LT
• PLANTATION AT LEESBURG OAK TREE VILLAGE
• PLANTATION/LEESBURG GLEN EAGLE
• LEESBURG THE PULP MILL SUB
• Legacy of Leesburg
• LEESBURG MAJESTIC OAKS SHORES
• PLANTATION AT LEESBURG GLEN EAGLE VILLAG
• LEGACY/LEESBURG UN #7
• PLANTATION/LEESBURG TARA VIEW
• PLANTATION AT LEESBURG HIDDEN OAK VILLAGE
• PLANTATION AT LEESBURG RIVERWALK VLG THE
• PLANTATION/LEESBURG GLENDALE V
• PLANTATION/LEESBURG ARBORDALE
• PLANTATION AT LEESBURG BELLE TERRE VILLAGE L
• PLANTATION AT LEESBURG RIVERWALK
• PLANTATION/LEESBURG
• PLANTATION/LEESBURG BELLE GROVE
• THE PLANTATION AT LEESBURG RIVERWALK VILLAGE
• PLANTATION/LEESBURG LAUREL VLY
• PLANTATION AT LEESBURG THE
• HAWTHORNE RESIDENTS COOPERATIV
• ROYAL OAK ESTATES 3RD ADD
• THE PLANTATION OF LEESBURG MAGNOLIA POINT
• PLANTATION @ LEESBURG HERON RUN
• HAWTHORNE AT LEESBURG
• SAGO PALM AT HAWTHORNE A COOPERATIVE
• THE PLANTATION AT LEESBURG to SAWGRASS VILLAGE
• HAWTHORNE AT LEESBURG A COOPERATIVE UNIT
• PLANTATION AT LEESBURG SUMMERBROOKE VILLAGE

What gates change about ownership

Controlled access typically comes with a manned gate, a transponder system, or both — funded through HOA dues. Expect guest-access procedures, delivery and contractor rules, and in some communities rental restrictions. Review the HOA budget for how the gate and any roving patrol are funded, and whether roads are private (the HOA maintains them — another line in the dues) or public.

Due diligence before you buy behind a gate

Request the HOA documents early: budget, reserves, rules, and the last two years of meeting minutes. Private roads, gates and common areas are owner-funded, so thin reserves become special assessments. Our buyer closing costs calculator helps you model dues and assessments into the real monthly cost.

What it costs to own here

At Lake County’s typical combined millage of 16.65 mills, a purchase at $299,000 (the median across these Leesburg gated communities) generates roughly $4,977 a year in property tax before exemptions — about $415 a month. Florida resets the assessed value to roughly your purchase price, so the seller’s current bill is not a preview of yours; a homesteaded owner then gets the $25,000–$50,000 exemption and the 3% Save Our Homes cap going forward. Citizens Property Insurance policies in Lake County average about $1,756 a year ($146 a month) — private-market quotes vary with roof age and wind mitigation, so price coverage before your inspection window closes. All-in, our county model puts the typical monthly cost of ownership in Lake County near $2,182 (principal and interest on the typical home, tax, and insurance).

Run your exact numbers: the property tax after purchase calculator uses Lake County’s verified millage, and the buyer closing costs calculator builds the full cash-to-close.

Demand and supply in Lake County right now

In the most recent IRS migration data (2022-2023), Lake County gained a net 12,855 people to relocation, with the largest inbound flows from NY, CA, NJ. Households moving IN reported average incomes of $80,711 versus $59,346 for those leaving — the income mix of demand, straight from tax filings. Population is up about 18.9% over the recent multi-year window. On the supply side, builders pulled 5,342 residential permits in Lake County in 2025 (3,999 single-family), up 7.1% year over year — against 6,316 at the 2023 peak. Permits are tomorrow’s inventory: a shrinking pipeline supports prices, a swelling one hands buyers leverage. Our valuation model reads the county as overvalued by about 5.9% versus its income-and-rent fundamentals.

Live inventory, refreshed nightly from the MLS.

Live gated-community listings in Leesburg

205 active listings carry the flag today (35% of Leesburg inventory), median asking $249,900, $157/sq ft, median 75 days on market. Photo cards link to the listing; refreshed nightly.

Newest gated community homes in Leesburg

$270,000 New

3 bd · 2 ba · 1,710 sq ft · built 1995

4529 Peach Tree Street, 34748

Plantation At Leesburg Glen Eagle Village

Listing courtesy of COLDWELL BANKER VANGUARD EDGE

$239,900 New

2 bd · 2 ba · 2,061 sq ft · built 2001

103 Orchid Way, 34748

Hawthorne At Leesburg A Coop

Listing courtesy of BLACK TIE REAL ESTATE PROFESSIONALS, INC.

$239,000 New

2 bd · 2 ba · 1,828 sq ft · built 1974

207 Hawthorne Boulevard, 34748

Hawthorne At Leesburg A Coop

Listing courtesy of HAWTHORNE RESIDENTS COOPERATIVE ASSOCIATION INC.

$90,000 New

2 bd · 2 ba · 864 sq ft · built 1974

428 Palo Verde Drive, 34748

Hawthorne At Leesburg A Coop

Listing courtesy of BLACK TIE REAL ESTATE PROFESSIONALS, INC.

$465,000 New

3 bd · 2.5 ba · 2,816 sq ft · built 2003

4632 Nottoway, 34748

Plantation At Leesburg Nottoway Village

Listing courtesy of CENTURY 21 MYERS ROSE REALTY

$415,000 New

3 bd · 2.5 ba · 2,684 sq ft · built 2003

24511 Bocage Way, 34748

Plantation At Leesburg Nottoway Village

Listing courtesy of CENTURY 21 MYERS ROSE REALTY

$360,000 New

3 bd · 2.5 ba · 2,377 sq ft · built 1994

26245 Newcombe Circle, 34748

Highland Lakes

Listing courtesy of GLOVEN REALTY

$330,000 New

3 bd · 2.5 ba · 2,512 sq ft · built 2000

25243 River Crest Drive, 34748

Plantation At Leesburg River Crest

Listing courtesy of RE/MAX PREMIER REALTY

$289,000 New

3 bd · 2 ba · 1,477 sq ft · built 2006

27111 Nostalgia Drive, 34748

legacy/leesburg

Listing courtesy of HOGAN REALTY GROUP INC

$279,000 New

3 bd · 2 ba · 2,017 sq ft · built 1994

26744 Racquet Circle, 34748

Highland Lakes

Listing courtesy of FLORIDA PLUS REALTY, LLC

$260,000 New

2 bd · 2 ba · 1,847 sq ft · built 2001

5024 Long Meadow Drive, 34748

Plantation At Leesburg Long Meadow Village

Listing courtesy of RE/MAX PREMIER REALTY

$259,900 New

3 bd · 2 ba · 1,538 sq ft · built 1998

815 Grand Vista Trail, 34748

Listing courtesy of CARLINO REAL ESTATE GROUP INC

$199,999 New

3 bd · 2 ba · 1,250 sq ft · built 2001

2947 Tangerine Court, 34748

Leesburg Royal Oak Estates

Listing courtesy of LPT REALTY, LLC

$199,950 New

2 bd · 2 ba · 952 sq ft · built 1992

25110 Bellevue, 34748

Plantation At Leesburg

Listing courtesy of FLORIDA PLUS REALTY, LLC

$180,000 New

2 bd · 2 ba · 1,120 sq ft · built 1989

25606 Belle Alliance Drive, 34748

Listing courtesy of CENTURY 21 MYERS ROSE REALTY

$175,000 New

2 bd · 2.5 ba · 1,288 sq ft · built 1990

2920 Pecan Avenue, 34748

Leesburg Royal Oak Estates

Listing courtesy of WRA BUSINESS & REAL ESTATE

$129,000 New

2 bd · 2 ba · 1,232 sq ft · built 1978

186 Hibiscus Way, 34748

Listing courtesy of HAWTHORNE RESIDENTS COOPERATIVE ASSOCIATION INC.

$125,000 New

2 bd · 2 ba · 1,100 sq ft · built 1980

151 Hibiscus Way, 34748

Hawthorne At Leesburg A Coop

Listing courtesy of HAWTHORNE RESIDENTS COOPERATIVE ASSOCIATION INC.

$119,500 New

1 bd · 1 ba · 560 sq ft · built 1987

639 NE Cottage Park Lane, 34748

Pennbrooke

Listing courtesy of PICKET FENCE REALTY LLC

$119,000 New

2 bd · 2 ba · 984 sq ft · built 1979

146 Hibiscus Way, 34748

Hawthorne At Leesburg A Coop

Listing courtesy of HAWTHORNE RESIDENTS COOPERATIVE ASSOCIATION INC.

$99,000 New

2 bd · 2 ba · 1,056 sq ft · built 1975

106 Jasmine Trail, 34748

Hawthorne At Leesburg A Coop

Listing courtesy of HAWTHORNE RESIDENTS COOPERATIVE ASSOCIATION INC.

$89,900 New

2 bd · 2 ba · 960 sq ft · built 1977

203 Aspen Circle, 34748

Listing courtesy of BLACK TIE REAL ESTATE PROFESSIONALS, INC.

$415,000 New

3 bd · 2 ba · 2,126 sq ft · built 2003

5524 Belle Terre Drive, 34748

Plantation At Leesburg Belle Terre Village L

Listing courtesy of FLORIDA PLUS REALTY, LLC

$350,000 New

3 bd · 2.5 ba · 2,555 sq ft · built 1998

3851 Manor Oaks Court, 34748

Plantation At Leesburg River Crest

Listing courtesy of CENTURY 21 MYERS ROSE REALTY

$336,000 New

3 bd · 2 ba · 1,761 sq ft · built 1994

25121 Meriweather Road, 34748

Plantation At Leesburg Tara View

Listing courtesy of COLDWELL BANKER VANGUARD EDGE REALTY

$310,000 New

3 bd · 2 ba · 1,655 sq ft · built 2017

5322 Pond Crossing Place, 34748

Legacy Leesburg

Listing courtesy of FLORIDA PLUS REALTY, LLC

$299,999 New

3 bd · 2 ba · 1,765 sq ft · built 2007

27336 Pine Straw Road, 34748

Listing courtesy of DOUBLE MM DEVELOPMENT, LLC

$119,000 New

2 bd · 2 ba · 1,200 sq ft · built 1977

104 Caladium Street, 34748

Hawthorne At Leesburg A Coop

Listing courtesy of EXIT REALTY TRI-COUNTY

$294,900 New

3 bd · 2 ba · 1,652 sq ft · built 1996

25735 Glen Eagle Drive, 34748

Plantation At Leesburg Oak Tree Village

Listing courtesy of MAXLIFE REALTY LLC

$225,000 New

2 bd · 2 ba · 1,350 sq ft · built 1991

5536 Rosewall Circle, 34748

Highland Lakes

Listing courtesy of EXP REALTY LLC

The most expensive gated community homes in Leesburg

Gated Community Homes by price

Leesburg gated community homes by community

Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale. The 60 communities with the most gated community homes listed are tabled; the rest follow.

Also with gated community homes for sale

• Plantation At Leesburg River Crest Unit 02 (1)
• Pennbrooke Ph Q Sub (1)
• Plantation At Leesburg Rosedown Village Lt (1)
• Arlington Ridge Ph 1-B (1)
• Plantation/Leesburg Arbordale (1)
• Legacy Of Leesburg, Unit 06 (1)
• Legacy Of Leesburg Unit 03 Lt 259 (1)
• Legacy Leesburg Unit 02 Lt 163 (1)
• Legacy Leesburg Unit 06 (1)
• Highland Lakes Ph 2-C (1)
• Plantation/Leesburg Tara View (1)
• Leesburg Legacy Leesburg Unit 06 (1)
• The Plantation At Leesburg – Sawgrass Village (1)
• Plantation At Leesburg Oak Tree Village (1)
• Plantation At Leesburg Brampton Village Lt (1)
• The Plantation At Leesburg Riverwalk Village (1)
• Legacy/Leesburg Un 05 (1)
• Pennbrooke Ph 02R Lt R23 (1)
• Legacy/Leesburg Un 05 (1)
• Pennbrooke Ph Ie Sub (1)
• Plantation At Leesburg Hidden Oak Village Tr A (1)
• Windsong/Leesburg Ph 2 (1)
• Pennbrooke (1)
• Plantation At Leesburg Sawgrass Village (1)
• Pennbrooke Ph 02P Lt P1 Being In 18-19-24 (1)
• Legacy Of Leesburg Unit 02 Lt 163 (1)
• Pennbrooke Ph M Sub (1)
• Pennbrooke Phase 1K, Unit Iii (1)
• The Plantation Of Leesburg Magnolia Point (1)
• Plantation At Leesburg Long Meadow Village (1)
• Pennbrooke Ph 01K Unit 03 (1)
• Sago Palm At Hawthorne A Cooperative (1)
• Plantation/Leesburg Belle Grove (1)
• Highland Lakes Ph 01A (1)
• Plantation/Leesburg Laurel Vly (1)
• Pennbrooke Ph 01H (1)
• Plantation @ Leesburg Heron Run (1)
• Arlington Ridge Ph 01-C (1)
• Royal Oak Estates 3Rd Add (1)
• The Plantation At Leesburg (1)
• Leesburg Coach Houses At Leesbug Condo (1)
• Hawthorne At Leesburg A Cooperative (1)
• Pennbrooke Ph 01A (1)
• Hawthorne Residents Cooperativ (1)
• Hawthorne At Leesburg A Cooperative Unit (1)

Explore more of Leesburg

• Gated Communities in Lake County
• Golf Course Communities in Leesburg
• New Construction Communities in Leesburg
• Find the best agent in Leesburg
• Best neighborhoods in Leesburg

Run the numbers in Lake County

• Find the best agent in Lake County
• Get a cash offer in Lake County
• Lake County housing scorecard
• What would selling net you
• Buyer closing costs calculator

Common questions

Community classifications are compiled from MLS-reported amenities, verified amenity records and MLS build-year data, as of 2026-06-16; they are informational, change over time, and are deemed reliable but not guaranteed — verify details with each association. Not an offer of housing to any protected class to the exclusion of others. Equal Housing Opportunity.