Leesburg, FL Homes

/56
$570,000
- 4 Beds
- 2 Baths
- 3,136 Sq Ft
27222 Nostalgia Dr, Leesburg, FL 34748

Model-perfect Stirling with a brand-new pool and birdcage overlooking serene water and conservation views on a private cul-de-sac lot! This 4-bedroom, 2-bath residence boasts a 2019 roof, 2021 HVAC system and a coveted 3-car garage. Inside, the open floorplan features a large great room, formal dining and a private office which could also be used as a 4th bedroom. Enjoy volume ceilings, crown

Angela Phillips

VANGIE BERRY SIGNATURE REALTY

(352) 441-3762

27222 Nostalgia Dr, Leesburg, FL 34748
/2
$1,189 per month
- 1 Bed
- 1 Bath
- 629 Sq Ft
- Apartment for Rent
1185 Bentley Rd Unit 3, Leesburg, FL 34748

Free application Income requirement is 2.5 times the rent. No evictions within the last 5 years. Credit and Background check will be performed on all applicants. $15 for trash added to monthly invoice. Renters liability insurance required, or can be obtained through landlord at $13.50 per month. If there are pets: Non refundable pet deposit $300 per pet. Re-occurring pet fee $25 per month per

Elizabeth Defalco EXP REALTY LLC

1185 Bentley Rd Unit 3, Leesburg, FL 34748
/2
$299,999 Sold Mar 28, 2025

27004 Nature View St, Leesburg, FL 34748
- 3 Beds
- 2 Baths
- 1,488 Sq Ft
- Built 2003
Last Sold Summary
- 3% Below List Price
- $202/SF
- 3 Days On Market
Current Estimated Value $295,963

Last Listing Agent Mo McLay DOUBLE MM DEVELOPMENT, LLC

27004 Nature View St, Leesburg, FL 34748

/100
Not Listed For Sale

5248 Tigers Tail, Leesburg, FL 34748
- 2 Beds
- 2 Baths
- 1,144 Sq Ft
- Built 1987
5248 Tigers Tail, Leesburg, FL 34748

Last Sold Summary
- $175/SF
- 74 Days On Market
Last Sold Price $200,000

Last Listing Agent Marty Bouhall CARLINO REAL ESTATE GROUP INC

/43
$329,247
- 3 Beds
- 2 Baths
- 2,111 Sq Ft
33409 Pennbrooke Pkwy, Leesburg, FL 34748

OFFERED FURNISHED!! PLUS - BRAND NEW STAINLEES STEEL KITCHEN APPLIANCES! EXPECTED THE UNEXPECTED! 3/2 HOME PLUS OVERSIZED BONUS ROOM...... NOT TO MENTION GOLF CART GARAGE AND STUNNING GOLF VIEWS!!! THIS IS A MUST SEE! THIS IS A HIDDEN GEM OF A COMMUNITY!!! Pennbrooke is located just 10 minutes south of The Villages and only 50 minutes from Orlando. The Pennbrooke Fairways golf course offers

Your 24/7 Team

MAXREV LLC

(352) 290-6286

33409 Pennbrooke Pkwy, Leesburg, FL 34748
/2
$1,189 per month
- 1 Bed
- 1 Bath
- 629 Sq Ft
- Apartment for Rent
1197 Bentley Rd Unit 1, Leesburg, FL 34748

Free application Income requirement is 2.5 times the rent. No evictions within the last 5 years. Credit and Background check will be performed on all applicants. $15 for trash added to monthly invoice. Renters liability insurance required, or can be obtained through landlord at $13.50 per month. If there are pets: Non refundable pet deposit $300 per pet. Re-occurring pet fee $25 per month per

Elizabeth Defalco EXP REALTY LLC

1197 Bentley Rd Unit 1, Leesburg, FL 34748
/2
$318,247 Sold Jul 23, 2025

509 Grand Vista Trail, Leesburg, FL 34748
- 3 Beds
- 2 Baths
- 1,872 Sq Ft
- Built 2001
Last Sold Summary
- 3% Below List Price
- $170/SF
- 110 Days On Market
Current Estimated Value $314,551

Last Listing Agent Your 24/7 Team MAXREV LLC

509 Grand Vista Trail, Leesburg, FL 34748

/14
Not Listed For Sale

37524 Quail Ridge Cir, Leesburg, FL 34788
- 3 Beds
- 2 Baths
- 1,186 Sq Ft
- Built 2005
37524 Quail Ridge Cir, Leesburg, FL 34788

Last Sold Summary
- $152/SF
- 25 Days On Market
Last Sold Price $179,900

Last Listing Agent Yvonne Vance CHARLES RUTENBERG REALTY ORLANDO

/37
$224,247
- 3 Beds
- 2 Baths
- 1,620 Sq Ft
752 Old Oaks Ln, Leesburg, FL 34748

FRESHLY PAINTED 2 BEDROOM/2 BATH HOME WITH A 3RD ROOM FOR OFFICE OR DEN WITH NO CLOSET. This 2 car garage home has a new roof in 2019 and a new heat pump in 2024Pennbrooke Fairways, a 55+ Community! This hidden gem of a community is located just 5 minutes south of The Villages, less than an hour to Orlando, Tampa and Daytona Beach within 90 minutes... just a perfect location for day trips!

Your 24/7 Team

MAXREV LLC

(352) 587-9995

752 Old Oaks Ln, Leesburg, FL 34748
/2
$929 per month
- 1 Bath
- 288 Sq Ft
- Apartment for Rent
420 Mills St Unit 18, Leesburg, FL 34748

Free application. Income requirement is 2.5 times the rent. No evictions within the last 5 years. Background check will be performed on all applicants. $12 monthly for trash, $25 monthly for water/sewer, added to monthly invoice. Renters liability insurance required, or can be obtained through landlord at $13.50 per month. If there are pets: Non refundable pet deposit $300 per pet. Re-occurring

Elizabeth Defalco EXP REALTY LLC

420 Mills St Unit 18, Leesburg, FL 34748
/2
$98,000 Sold Mar 14, 2025

34939 Learn Rd, Leesburg, FL 34788
- 2 Beds
- 1.5 Baths
- 1,116 Sq Ft
- Built 1971
Last Sold Summary
- 36% Below List Price
- $88/SF
- 429 Days On Market
Last Listing Agent Annette Krupnicka HIGHLIGHT REALTY CORP/LW

34939 Learn Rd, Leesburg, FL 34788

/25
Not Listed For Sale

25319 La Grange Ct, Leesburg, FL 34748
- 2 Beds
- 2 Baths
- 1,224 Sq Ft
- Built 1990
25319 La Grange Ct, Leesburg, FL 34748

Last Sold Summary
- $125/SF
- 97 Days On Market
Last Sold Price $153,000

Last Listing Agent Cary Fier CENTURY 21 MYERS REALTY

/18
$185,000
- 2 Beds
- 2 Baths
- 1,250 Sq Ft
1129 Apple Terrace, Leesburg, FL 34748

One or more photo(s) has been virtually staged. Quiet peaceful gated community in west Leesburg with easy access to I-75, Florida Turnpike and locally to The Villages, Clermont, Eustis, Groveland, Fruitland Park, Lady Lake, Mascotte, Mount Dora, Tavares and Wildwood. This neighborhood with its man-made lakes, creates a serene backdrop for both two story townhouses and one story villas that share

Deborah Elliott

CHARLES RUTENBERG REALTY ORLANDO

(352) 292-0539

1129 Apple Terrace, Leesburg, FL 34748
/2
$1,029 per month
- 1 Bed
- 1 Bath
- 576 Sq Ft
- Apartment for Rent
420 Mills St Unit 48, Leesburg, FL 34748

Application fee is free. Income requirement is 2.5 times the rent. No evictions within the last 5 years. Background check will be performed on all applicants. $12 monthly for trash, $25 monthly for water/sewer, added to monthly invoice. Renters liability insurance required, or can be obtained through landlord at $13.50 per month. If there are pets: Non refundable pet deposit $300 per pet.

Elizabeth Defalco EXP REALTY LLC

420 Mills St Unit 48, Leesburg, FL 34748
/2
$257,000 Sold Apr 10, 2025

32619 Oak Park Dr, Leesburg, FL 34748
- 2 Beds
- 2 Baths
- 1,631 Sq Ft
- Built 1994
Last Sold Summary
- 3% Below List Price
- $158/SF
- 85 Days On Market
Current Estimated Value $260,098

Last Listing Agent Your 24/7 Team MAXREV LLC

32619 Oak Park Dr, Leesburg, FL 34748

/16
Not Listed For Sale

229 Crestrun Loop, Leesburg, FL 34748
- 4 Beds
- 3 Baths
- 2,102 Sq Ft
- Built 2013
229 Crestrun Loop, Leesburg, FL 34748

Last Sold Summary
- 4% Below List Price
- $204/SF
- 2 Days On Market
Last Sold Price $429,000

Last Listing Agent Jerry Galbreath HAWTHORNE RESIDENTS COOPERATIVE ASSOCIATION INC.

/26
$80,000 Open House 3/28
- 2 Beds
- 2 Baths
4616 Skyline Dr, Leesburg, FL 34748

COMMUNITY: Sought after community which sits on the Harris Chain of Lakes with private boat ramp. Conveniently located to shopping, dining and to the up and coming down town Leesburg. Also within an hours drive to Disney and a couple hour drive to several beaches and fresh water springs. The community has a pool, clubhouse and walking path to the water. Lifestyle Fee is $391 per month. Must pass

Lisa Skutt

Down Home Realty

(352) 703-5139

4616 Skyline Dr, Leesburg, FL 34748
/2
$3,300 per month
- 3 Beds
- 2 Baths
- 1,827 Sq Ft
- House for Rent
26209 Glen Eagle Dr, Leesburg, FL 34748

Beautiful home for rent on monthly basis. January - March, 2026 is unavailable.

Dawn Brooks CENTURY 21 MYERS REALTY

26209 Glen Eagle Dr, Leesburg, FL 34748
/2
$400,000 Sold Sep 18, 2025

2617 Hollow Ln, Leesburg, FL 34748
- 6 Beds
- 4 Baths
- 2,262 Sq Ft
- Built 1999
Last Sold Summary
- 4% Below List Price
- $177/SF
- 124 Days On Market
Current Estimated Value $397,746

Last Listing Agent Hanh Dinh COMPASS FLORIDA LLC

2617 Hollow Ln, Leesburg, FL 34748

/2
Est $351,572 Not Listed For Sale

100 N 14th St, Leesburg, FL 34748
- Built 1972
100 N 14th St, Leesburg, FL 34748

Last Sold Summary
- 41% Above List Price
- $132/SF
- 1,971 Days On Market
Last Sold Price $249,900

Last Listing Agent Jeffrey Carlino CARLINO COMMERCIAL GROUP, INC.

/61
$1,695,000
- 4 Beds
- 3.5 Baths
- 3,745 Sq Ft
424 Bedminster Way, The Villages, FL 34762

Discover your dream pool home in the Enclave Village of Dabney, featuring a stunning 4-bedroom plus a den, 3.5-bath Kings Bay Premier home. Designed for both elegant entertaining and everyday comfort, this residence showcases refined finishes, thoughtful upgrades, and a highly functional layout. Enjoy easy golf cart access to both Sawgrass and Brownwood from this ideally located home.This

Karen Kamperman

KELLER WILLIAMS CORNERSTONE RE

(352) 722-2316

424 Bedminster Way, The Villages, FL 34762
/2
$3,000 per month
- 3 Beds
- 2 Baths
- 1,761 Sq Ft
- House for Rent
25121 Meriweather Rd, Leesburg, FL 34748

Beautiful turnkey furnished monthly rental available in the desirable Plantation at Leesburg. Three bedrooms, two baths, screened lanai.

Dawn Brooks CENTURY 21 MYERS REALTY

25121 Meriweather Rd, Leesburg, FL 34748
/2
$122,300 Sold Apr 29, 2025

1223 Tuskegee St, Leesburg, FL 34748
- 3 Beds
- 1 Bath
- 1,263 Sq Ft
- Built 1971
Last Sold Summary
- 29% Below List Price
- $97/SF
- 167 Days On Market
Current Estimated Value $158,412

Last Listing Agent Bill Vaught (REO Vaught Realty LLC VAUGHT REALTY

1223 Tuskegee St, Leesburg, FL 34748

/25
Not Listed For Sale

34447 Oak Ave, Leesburg, FL 34788
- 2 Beds
- 1 Bath
- 672 Sq Ft
- Built 1975
34447 Oak Ave, Leesburg, FL 34788

Last Sold Summary
- $112/SF
- 1 Day On Market
Last Sold Price $75,000

Last Listing Agent Tammy King, PA ERA GRIZZARD REAL ESTATE

/35
$349,997
- 3 Beds
- 2 Baths
- 1,694 Sq Ft
21821 King John St, Leesburg, FL 34748

Better than new! This meticulously renovated 3BR/2BA home offers modern elegance in an exclusive 24/7 guard-gated enclave. Situated on a spacious corner lot, this property boasts a total transformation: Freshly Painted–Crisp new palette inside and out. Gourmet Kitchen–New cabinets, quartz countertops, and sleek new appliances. Modern Flooring–Durable and stylish new floors throughout. Open

Kristi Matthew

CENTURY 21 CARIOTI

(352) 744-8212

21821 King John St, Leesburg, FL 34748
/2
$1,029 per month
- 1 Bed
- 1 Bath
- 576 Sq Ft
- Apartment for Rent
420 Mills St Unit 6, Leesburg, FL 34748

Application fee is free. Income requirement is 2.5 times the rent. No evictions within the last 5 years. Background check will be performed on all applicants. $12 monthly for trash, $25 monthly for water/sewer, added to monthly invoice. Renters liability insurance required, or can be obtained through landlord at $13.50 per month. If there are pets: Non refundable pet deposit $300 per pet.

Elizabeth Defalco EXP REALTY LLC

420 Mills St Unit 6, Leesburg, FL 34748
/2
$260,000 Sold Apr 08, 2025

11032 Moore St, Leesburg, FL 34788
- 3 Beds
- 2 Baths
- 1,416 Sq Ft
- Built 1994
Last Sold Summary
- 5% Below List Price
- $184/SF
- 22 Days On Market
Current Estimated Value $256,155

Last Listing Agent Brandon Shrout DOWN HOME REALTY, LLLP

11032 Moore St, Leesburg, FL 34788

/38
Not Listed For Sale

35140 Forest Lake Rd, Leesburg, FL 34788
- 3 Beds
- 2 Baths
- 1,404 Sq Ft
- Built 1994
35140 Forest Lake Rd, Leesburg, FL 34788

Last Sold Summary
- $167/SF
- 94 Days On Market
Last Sold Price $235,000

Last Listing Agent Barbara Breuer FIERCE REALTY

/25
$34,900
- 2 Beds
- 1.5 Baths
- 816 Sq Ft
1208 Lee St Unit 133, Leesburg, FL 34748

Bring your fishing pole and boat to your new home with the Harris Chain of Lakes just steps away! This community, Lakeshore Cobblestone, offers you an unmatched lakefront park, fishing pier, and marina with a partial lake view from your Florida Room! One step inside, and you will immediately appreciate the stylish updates and features of this home. The front 10 x 24 Florida room adds square

John Stiller

Right Realty Connection INC

(352) 722-5870

1208 Lee St Unit 133, Leesburg, FL 34748
/2
$929 per month
- 1 Bath
- 288 Sq Ft
- Apartment for Rent
420 Mills St Unit 11, Leesburg, FL 34748

Application fee is free. Income requirement is 2.5 times the rent. No evictions within the last 5 years. Background check will be performed on all applicants. $12 monthly for trash, $25 monthly for water/sewer, added to monthly invoice. Renters liability insurance required, or can be obtained through landlord at $13.50 per month. If there are pets: Non refundable pet deposit $300 per pet.

Elizabeth Defalco EXP REALTY LLC

420 Mills St Unit 11, Leesburg, FL 34748
/2
$80,000 Sold Apr 29, 2025

101 Poinsettia Cove, Leesburg, FL 34748
- 2 Beds
- 2 Baths
- 1,486 Sq Ft
- Built 1977
Last Sold Summary
- $54/SF
- 20 Days On Market
Current Estimated Value $81,253

Last Listing Agent Maria Crisostomo HAWTHORNE RESIDENTS COOPERATIVE ASSOCIATION INC.

101 Poinsettia Cove, Leesburg, FL 34748

/32
Not Listed For Sale

27815 N Pelican Isle Dr, Leesburg, FL 34748
- 2 Beds
- 2 Baths
- 1,344 Sq Ft
- Built 1984
27815 N Pelican Isle Dr, Leesburg, FL 34748

Last Sold Summary
- $147/SF
- 106 Days On Market
Last Sold Price $197,500

Last Listing Agent Bill Beckett, II JEMINI REALTY CORP

/19
$94,900
- 1 Bed
- 1 Bath
- 490 Sq Ft
615 NE Cottage Park Ln, Leesburg, FL 34748

Adorable one bedroom, open kitchen to living Room, Manufactured Home in the Gated Community Pennbrooke Fairways! Subflooring has been replaced in main living area and kitchen. New laminate floors throughout. HVAC in 2021, Newer Hot water heater. Large enclosed lanai on side with storage area and laundry. Rear private Lanai with privacy fence behind the home. Very clean inside and out. HOA

Scott Hutchinson

SUNBURST PROPERTIES

(352) 724-1663

615 NE Cottage Park Ln, Leesburg, FL 34748
/2
$1,029 per month
- 1 Bed
- 1 Bath
- 576 Sq Ft
- Apartment for Rent
420 Mills St Unit 35, Leesburg, FL 34748

Application fee is free. Income requirement is 2.5 times the rent. No evictions within the last 5 years. Background check will be performed on all applicants. $12 monthly for trash, $25 monthly for water/sewer, added to monthly invoice. Renters liability insurance required, or can be obtained through landlord at $13.50 per month. If there are pets: Non refundable pet deposit $300 per pet.

Elizabeth Defalco EXP REALTY LLC

420 Mills St Unit 35, Leesburg, FL 34748
/2
$390,000 Sold May 02, 2025

10230 Barrington Ct, Leesburg, FL 34788
- 3 Beds
- 2 Baths
- 2,286 Sq Ft
- Built 1998
Last Sold Summary
- 2% Below List Price
- $171/SF
- 43 Days On Market
Current Estimated Value $388,606

Last Listing Agent Cynthia Wheeler ERA GRIZZARD REAL ESTATE

10230 Barrington Ct, Leesburg, FL 34788

/53
Not Listed For Sale

24813 Pine Hill, Leesburg, FL 34748
- 2 Beds
- 2 Baths
- 1,944 Sq Ft
- Built 1987
24813 Pine Hill, Leesburg, FL 34748

Last Sold Summary
- $115/SF
- 58 Days On Market
Last Sold Price $223,000

Last Listing Agent Adriana Skoloda RE/MAX

/28
$152,900
- 2 Beds
- 2 Baths
- 1,072 Sq Ft
12033 Lake Pines Rd, Leesburg, FL 34788

Opportunity Awaits for the Harris Chain of Lakes! Welcome to 12033 Lake Pines Rd, Leesburg, FL, a charming 2-bedroom, 2-bath manufactured home offering direct canal-front access to Lake Eustis and the renowned Harris Chain of Lakes—one of Central Florida’s most desirable boating and waterfront lifestyles. This 1970 (single-wide) manufactured home is perfectly positioned on a navigable canal,

Robin Costoplos

LAKE PROPERTY STARS

(352) 290-5935

12033 Lake Pines Rd, Leesburg, FL 34788
/2
$929 per month
- 1 Bath
- 288 Sq Ft
- Apartment for Rent
420 Mills St Unit 14, Leesburg, FL 34748

Application fee is free. Income requirement is 2.5 times the rent. No evictions within the last 5 years. Background check will be performed on all applicants. $12 monthly for trash, $25 monthly for water/sewer, added to monthly invoice. Renters liability insurance required, or can be obtained through landlord at $13.50 per month. If there are pets: Non refundable pet deposit $300 per pet.

Elizabeth Defalco EXP REALTY LLC

420 Mills St Unit 14, Leesburg, FL 34748
/2
$204,900 Sold Sep 30, 2025

25331 Hibiscus St, Leesburg, FL 34748
- 2 Beds
- 2 Baths
- 1,413 Sq Ft
- Built 1993
Last Sold Summary
- 25% Below List Price
- $145/SF
- 699 Days On Market
Current Estimated Value $210,965

Last Listing Agent Cary Fier CENTURY 21 MYERS REALTY

25331 Hibiscus St, Leesburg, FL 34748

/31
Not Listed For Sale

34336 Island Dr, Leesburg, FL 34788
- 2 Beds
- 2 Baths
- 1,416 Sq Ft
- Built 1972
34336 Island Dr, Leesburg, FL 34788

Last Sold Summary
- $335/SF
- 30 Days On Market
Last Sold Price $475,000

Last Listing Agent RE Cheryl Christ SONNE REAL ESTATE INC

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