Jennifer Kelley's profile photo

Jennifer Kelley

Licensed Real Estate Salesperson
About Jennifer
Jennifer Kelley is a Principal at The Encore Team at Compass, a powerhouse, partner-led collective built on the legacy and success of Around Town Real Estate. With a strong foundation in market performance, hyper-local expertise, and a collaborative approach, the team delivers a level of strategy, creativity, and execution rarely found in traditional real estate.

Guided by her signature philosophy, “Moving you forward, with heart,” Jennifer brings a refined yet deeply personal approach to every client experience. She understands that home is more than a transaction — it’s a meaningful life transition — and she is known for navigating each step with intention, clarity, and care.

A lifelong Fairfield County resident and 25+ year Newtown local, Jennifer offers clients an insider’s perspective on the community she proudly calls home. She and her husband, Patrick, have chosen to raise their children, Reagan and Declan, in the very town that shaped their own lives — a connection that informs both her work and her commitment to her clients.

Prior to real estate, Jennifer built a successful career in finance, equipping her with the analytical expertise and strategic mindset needed to guide clients through complex decisions with confidence. Today, she seamlessly blends that business acumen with a relationship-first approach, ensuring each client feels supported, informed, and empowered.

For those seeking a thoughtful, elevated real estate experience backed by proven results and genuine care, Jennifer delivers — every time.

Jennifer Kelley’s Listings

$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
$939,900 | 41 Charter Ridge Drive, Newtown, CT 06482
1/40
Listed By Compass

$939,900

4
Bedrooms
3,782
Square Feet
1.02
Acres
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
$684,000 | 74 Middle Quarter Road, Woodbury, CT 06798
1/40
Listed By CompassUnder Contract

$684,000

4
Bedrooms
2,874
Square Feet
4.7
Acres
a sign that is sitting on the grass of the house
a front view of a house with a yard
front view of a house with a yard
a view of entryway and hall with wooden floor
a view of an empty room with a window and wooden floor
a view of a livingroom with a fireplace and window
a view of an empty room with wooden floor fireplace and a window
a living room with furniture a flat screen tv and a fireplace
a kitchen with a stove a sink and a refrigerator
a kitchen with stainless steel appliances granite countertop a stove sink and cabinets
a kitchen with stainless steel appliances granite countertop a stove top oven a refrigerator a sink and dishwasher with wooden floor
a view of a balcony
an empty room with windows
an empty room with windows
a bedroom with a bed and a window
a bathroom with a granite countertop sink a mirror and a shower
a bathroom with a sink and a mirror
a view of an empty room with wooden floor
a living room with furniture and a flat screen tv
a view of empty room with wooden floor
a bathroom with a granite countertop sink toilet and shower
a view of hallway with wooden floor
a view of an empty room with a window
an empty room with windows
a view of a bathroom
a utility room with dryer and washer
an aerial view of a house with outdoor space swimming pool
an aerial view of a city with lots of residential buildings
a view of a golf course
a view of a yard with plants
a front view of a house with garden
a picture of a bathroom with a shower
unknown
$625,000 | 20 Brookside Court, Unit 20, Newtown, CT 06470
$625,000 | 20 Brookside Court, Unit 20, Newtown, CT 06470
$625,000 | 20 Brookside Court, Unit 20, Newtown, CT 06470
$625,000 | 20 Brookside Court, Unit 20, Newtown, CT 06470
$625,000 | 20 Brookside Court, Unit 20, Newtown, CT 06470
1/38
Listed By CompassUnder Contract

$625,000

2
Bedrooms
1,716
Square Feet
a front view of a house with a yard and trees
a house view with a garden space
a view of entryway and hall with wooden floor
a living room with furniture and a wooden floor
a living room with furniture fireplace and flat screen tv
a living room with furniture fireplace and flat screen tv
a living room with furniture flat screen tv and a fireplace
a living room with stainless steel appliances furniture and a kitchen view
a dining room with furniture a kitchen view and a chandelier
a living room with stainless steel appliances furniture and a kitchen view
a dining room with furniture a chandelier and wooden floor
a kitchen with a refrigerator sink and microwave
a kitchen with granite countertop a sink stove and cabinets
a view of a dining room with furniture window and outside view
a bedroom with a bed and wooden floor
a bedroom with a bed and a dresser
a bedroom with a bed and a television
a bathroom with a sink and a mirror
a bedroom with a bed and flat screen tv
a bathroom with a sink toilet and shower
a bathroom with a toilet and shower curtain
a room with furniture and a fireplace
a room with furniture a flat screen tv and a stool
a view of a hallway with paintings on the wall
a bedroom with furniture and a window
a room with storage and utility
a living room with furniture a flat screen tv and a table
a bedroom with furniture and stairs
a bathroom with a sink mirror and toilet
a bathroom with a sink a toilet and a mirror
a view of a room with gym equipment
a view of a roof deck with table and chairs and a fire pit
a view of a patio with couches chairs and wooden floor
a view of a house with a backyard and sitting area
a view of a terrace
a view of a terrace with furniture
an aerial view of residential houses with outdoor space and trees
$510,000 | 16 Curtis Avenue, New Fairfield, CT 06812
$510,000 | 16 Curtis Avenue, New Fairfield, CT 06812
$510,000 | 16 Curtis Avenue, New Fairfield, CT 06812
1/40
Listed By CompassUnder Contract - Continue To Show

$510,000

3
Bedrooms
1,414
Square Feet
0.25
Acres

Jennifer Kelley’s Transactions

Past Sales
a front view of a house with garden

$1,614,357

5
Bedrooms
7,919
Square Feet
2.05
Acres
a front view of a house with a yard

$1,450,000

5
Bedrooms
6,000
Square Feet
2.05
Acres
a front view of a house with a yard

$1,225,000

6
Bedrooms
6,074
Square Feet
1.95
Acres
a front view of a house with garden

$1,100,000

3
Bedrooms
2,700
Square Feet
$1,060,000 | 130 Branch Brook Road, Wilton, CT 06897

$1,060,000

5
Bedrooms
6,607
Square Feet
2
Acres
a view of a house with a yard table and chairs

$1,050,000

5
Bedrooms
4,146
Square Feet
4.55
Acres
$1,000,000 | 8 Boulder Creek Road, Newtown, CT 06470

$1,000,000

5
Bedrooms
6,116
Square Feet
2.09
Acres
an aerial view of a house with swimming pool a yard and lake view

$950,000

4
Bedrooms
2,363
Square Feet
0.6
Acres
a front view of house with yard and green space

$950,000

4
Bedrooms
4,006
Square Feet
2.02
Acres
$935,000 | 12 Plumb Creek Road, Trumbull, CT 06611

$935,000

4
Bedrooms
3,899
Square Feet
1
Acres
a front view of a house with a garden and trees

$925,000

4
Bedrooms
3,388
Square Feet
0.6
Acres
a front view of a house with swimming pool and porch

$850,000

4
Bedrooms
3,363
Square Feet
2.02
Acres
$832,000 | 11 Ashwood Lane, Brookfield, CT 06804

$832,000

4
Bedrooms
3,925
Square Feet
1.97
Acres
$825,000 | 27 Yogananda Street, Newtown, CT 06482

$825,000

4
Bedrooms
3,713
Square Feet
2.7
Acres
a front view of a building with trees around

$825,000

3
Bedrooms
3,496
Square Feet
1.03
Acres
$822,000 | 2 Old Farm Hill Road, Newtown, CT 06470

$822,000

5
Bedrooms
3,471
Square Feet
2.3
Acres
$820,000 | 210 Brushy Hill Road, Newtown, CT 06470

$820,000

4
Bedrooms
3,300
Square Feet
2.01
Acres
front view of a house with a yard

$806,000

4
Bedrooms
3,044
Square Feet
1.34
Acres
Past Rentals
$2,900 | 9 Harmony Lane, Monroe, CT 06468

$2,900

3
Bedrooms
2,388
Square Feet
1.1
Acres
a living room with furniture a fireplace and a flat screen tv

$2,000

1
Bedrooms
1,200
Square Feet
1.33
Acres
$2,000 | 40 Cliff Street, Shelton, CT 06484

$2,000

3
Bedrooms
1,219
Square Feet
0.15
Acres
$1,750 | 85 Chestnut Street, Unit G, Bethel, CT 06801

$1,750

1
Bedrooms
764
Square Feet
a front view of a house with a yard

$1,400

1
Bedrooms
859
Square Feet
0.15
Acres